DE10017651A1 - Di- and polyisocyanates blocked with pyrazoles disubstituted in the 3,4-position and their use - Google Patents
Di- and polyisocyanates blocked with pyrazoles disubstituted in the 3,4-position and their useInfo
- Publication number
- DE10017651A1 DE10017651A1 DE2000117651 DE10017651A DE10017651A1 DE 10017651 A1 DE10017651 A1 DE 10017651A1 DE 2000117651 DE2000117651 DE 2000117651 DE 10017651 A DE10017651 A DE 10017651A DE 10017651 A1 DE10017651 A1 DE 10017651A1
- Authority
- DE
- Germany
- Prior art keywords
- blocked
- groups
- polyisocyanates
- unsubstituted alkyl
- cycloalkylaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 46
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 46
- 150000003217 pyrazoles Chemical class 0.000 title claims description 22
- 238000000576 coating method Methods 0.000 claims abstract description 47
- 239000011248 coating agent Substances 0.000 claims abstract description 39
- 239000000463 material Substances 0.000 claims abstract description 32
- 230000005855 radiation Effects 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 13
- 239000013466 adhesive and sealant Substances 0.000 claims description 12
- 125000005442 diisocyanate group Chemical group 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000002981 blocking agent Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- VQTVFIMEENGCJA-UHFFFAOYSA-N 3,4-dimethyl-1H-pyrazole Chemical group CC=1C=NNC=1C VQTVFIMEENGCJA-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000003156 secondary amide group Chemical group 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 125000003142 tertiary amide group Chemical group 0.000 claims description 2
- 238000001029 thermal curing Methods 0.000 claims description 2
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- -1 3,4-disubstituted pyrazoles Chemical class 0.000 abstract description 38
- 239000000853 adhesive Substances 0.000 abstract description 4
- 230000001070 adhesive effect Effects 0.000 abstract description 4
- 239000003566 sealing material Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 description 13
- 239000003431 cross linking reagent Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000012790 adhesive layer Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000010422 painting Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000006855 networking Effects 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- WVWYODXLKONLEM-UHFFFAOYSA-N 1,2-diisocyanatobutane Chemical compound O=C=NC(CC)CN=C=O WVWYODXLKONLEM-UHFFFAOYSA-N 0.000 description 1
- FCNOUKVBZHFTGZ-UHFFFAOYSA-N 1,2-diisocyanatocyclobutane Chemical compound O=C=NC1CCC1N=C=O FCNOUKVBZHFTGZ-UHFFFAOYSA-N 0.000 description 1
- ODKSRULWLOLNJQ-UHFFFAOYSA-N 1,2-diisocyanatocyclohexane Chemical compound O=C=NC1CCCCC1N=C=O ODKSRULWLOLNJQ-UHFFFAOYSA-N 0.000 description 1
- WOZKRVDYLALSEF-UHFFFAOYSA-N 1,2-diisocyanatocyclopentane Chemical compound O=C=NC1CCCC1N=C=O WOZKRVDYLALSEF-UHFFFAOYSA-N 0.000 description 1
- IZAKKEAUPDMLQY-UHFFFAOYSA-N 1,3-bis(2-isocyanatoethyl)cyclohexane Chemical compound O=C=NCCC1CCCC(CCN=C=O)C1 IZAKKEAUPDMLQY-UHFFFAOYSA-N 0.000 description 1
- FADTWTSAFSHQKZ-UHFFFAOYSA-N 1,3-bis(3-isocyanatopropyl)cyclohexane Chemical compound O=C=NCCCC1CCCC(CCCN=C=O)C1 FADTWTSAFSHQKZ-UHFFFAOYSA-N 0.000 description 1
- AWKXSTZEJQKUEG-UHFFFAOYSA-N 1,3-bis(4-isocyanatobutyl)cyclohexane Chemical compound O=C=NCCCCC1CCCC(CCCCN=C=O)C1 AWKXSTZEJQKUEG-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- MYXZTICARLPUED-UHFFFAOYSA-N 1,3-diisocyanatocyclobutane Chemical compound O=C=NC1CC(N=C=O)C1 MYXZTICARLPUED-UHFFFAOYSA-N 0.000 description 1
- GNQKHBSIBXSFFD-UHFFFAOYSA-N 1,3-diisocyanatocyclohexane Chemical compound O=C=NC1CCCC(N=C=O)C1 GNQKHBSIBXSFFD-UHFFFAOYSA-N 0.000 description 1
- HJXDYZHSBKUFMA-UHFFFAOYSA-N 1,3-diisocyanatocyclopentane Chemical compound O=C=NC1CCC(N=C=O)C1 HJXDYZHSBKUFMA-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- UTFSEWQOIIZLRH-UHFFFAOYSA-N 1,7-diisocyanatoheptane Chemical compound O=C=NCCCCCCCN=C=O UTFSEWQOIIZLRH-UHFFFAOYSA-N 0.000 description 1
- KANVKUMQZXAJGG-UHFFFAOYSA-N 1-isocyanato-2-(3-isocyanatopropyl)cyclohexane Chemical compound O=C=NCCCC1CCCCC1N=C=O KANVKUMQZXAJGG-UHFFFAOYSA-N 0.000 description 1
- UBUVRJGTZLFDTB-UHFFFAOYSA-N 1-isocyanato-2-(4-isocyanatobutyl)cyclohexane Chemical compound O=C=NCCCCC1CCCCC1N=C=O UBUVRJGTZLFDTB-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- MRPZLXMWCIWOGP-UHFFFAOYSA-N 2,3-dimethyl-n-phenylaniline Chemical group CC1=CC=CC(NC=2C=CC=CC=2)=C1C MRPZLXMWCIWOGP-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- AFTBJQDQENGCPC-UHFFFAOYSA-N 2,5-ditert-butyl-4-methylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C=C1C(C)(C)C AFTBJQDQENGCPC-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- ABROBCBIIWHVNS-UHFFFAOYSA-N 2-Ethylbenzenethiol Chemical compound CCC1=CC=CC=C1S ABROBCBIIWHVNS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- ALQRZHOESQKZCO-UHFFFAOYSA-N 2-butoxyethanol;2-propoxyethanol Chemical compound CCCOCCO.CCCCOCCO ALQRZHOESQKZCO-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- QAPHHRYGSJGRMW-UHFFFAOYSA-N 2-methyl-n-phenylmethoxyprop-2-enamide Chemical compound CC(=C)C(=O)NOCC1=CC=CC=C1 QAPHHRYGSJGRMW-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- IOOWDXMXZBYKLR-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole-4-carboxylic acid Chemical compound CC1=NNC(C)=C1C(O)=O IOOWDXMXZBYKLR-UHFFFAOYSA-N 0.000 description 1
- AMUBKBXGFDIMDJ-UHFFFAOYSA-N 3-heptyl-1,2-bis(9-isocyanatononyl)-4-pentylcyclohexane Chemical compound CCCCCCCC1C(CCCCC)CCC(CCCCCCCCCN=C=O)C1CCCCCCCCCN=C=O AMUBKBXGFDIMDJ-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- RISOHYOEPYWKOB-UHFFFAOYSA-N 4-bromo-3,5-dimethyl-1h-pyrazole Chemical compound CC1=NNC(C)=C1Br RISOHYOEPYWKOB-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
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- DHKSNCURAWLWTR-UHFFFAOYSA-N 5-isocyanato-1-(3-isocyanatopropyl)-1,3,3-trimethylcyclohexane Chemical compound CC1(C)CC(N=C=O)CC(C)(CCCN=C=O)C1 DHKSNCURAWLWTR-UHFFFAOYSA-N 0.000 description 1
- FQIIRMHXQFYLCA-UHFFFAOYSA-N 5-isocyanato-1-(4-isocyanatobutyl)-1,3,3-trimethylcyclohexane Chemical compound CC1(C)CC(N=C=O)CC(C)(CCCCN=C=O)C1 FQIIRMHXQFYLCA-UHFFFAOYSA-N 0.000 description 1
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
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- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- JTDWCIXOEPQECG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCCCC(C)(C)C JTDWCIXOEPQECG-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- RLPXAKVDWHODPX-UHFFFAOYSA-N cyclohexane;ethene Chemical compound C=C.C1CCCCC1 RLPXAKVDWHODPX-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- SOOARYARZPXNAL-UHFFFAOYSA-N methyl-thiophenol Natural products CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 description 1
- YULMNMJFAZWLLN-UHFFFAOYSA-N methylenecyclohexane Chemical compound C=C1CCCCC1 YULMNMJFAZWLLN-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- SKHDXTZKLIHWBC-UHFFFAOYSA-N n-(1-chlorohexan-2-ylidene)hydroxylamine Chemical class CCCCC(CCl)=NO SKHDXTZKLIHWBC-UHFFFAOYSA-N 0.000 description 1
- UCFRVQXGPJMWPG-UHFFFAOYSA-N n-(2,6-dimethylheptan-4-ylidene)hydroxylamine Chemical compound CC(C)CC(=NO)CC(C)C UCFRVQXGPJMWPG-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical group OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XVNKRRXASPPECQ-UHFFFAOYSA-N phenyl n-phenylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CC=C1 XVNKRRXASPPECQ-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Chemical group 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 125000001749 primary amide group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft neue, mit in 3,4-Stellung disubstituierten Pyrazolen blockierte Di- und Polyisocyanate. Außerdem betrifft die vorliegende Erfindung die Verwendung der neuen, mit in 3,4-Stellung disubstituierten Pyrazolen blockierten Di- und Polyisocyanate zur Herstellung von thermisch oder thermisch und mit aktinischer Strahlung härtbaren Beschichtungsstoffen, Klebstoffen und Dichtungsmassen.The present invention relates to new pyrazoles disubstituted in the 3,4-position blocked di- and polyisocyanates. The present invention also relates to Use of the new di- and blocked with pyrazoles disubstituted in the 3,4-position Polyisocyanates for the production of thermal or thermal and with actinic Radiation-curable coating materials, adhesives and sealants.
Di- und Polyisocyanate, die mit Pyrazolen blockiert sind, die in 3-Stellung monosubstituiert, in 3,5-Stellung disubstituiert oder in 3,4,5-Stellung trisubstituiert sind, sind aus der europäischen Patentschrift EP 0 159 117 B1 bekannt. Expressis verbis werden 3-Methyl-, 3,5-Dimethyl-, 3-Methyl-5-phenyl-, 4-Benzyl-3,5-dimethyl-, 4-Nitro-3,5- dimethyl- und 4-Brom-3,5-dimethyl-pyrazol und 3,5-Dimethylpyrazol-4-carboxylat oder - carboxanilid genannt. Die blockierten Di- und Polyisocyanate werden für die Herstellung von Beschichtungsstoffen, insbesondere von Elektrotauchlacken, verwendet.Di- and polyisocyanates blocked with pyrazoles in the 3-position are monosubstituted, disubstituted in the 3,5 position or trisubstituted in the 3,4,5 position, are known from European patent EP 0 159 117 B1. Expressis become verbis 3-methyl, 3,5-dimethyl, 3-methyl-5-phenyl, 4-benzyl-3,5-dimethyl, 4-nitro-3,5- dimethyl- and 4-bromo-3,5-dimethyl-pyrazole and 3,5-dimethylpyrazole-4-carboxylate or - called carboxanilide. The blocked di- and polyisocyanates are used in the manufacture of coating materials, in particular electro-dipping paints, used.
Aus der deutschen Patentanmeldung DE 44 41 418 A1 ist ein Verfahren zur Herstellung von 3,5-Dimethylpyrazol-blockierten Poylisocyanten bekannt, bei dem das bei der Herstellung von 3,5-Dimethylpyrazol anfallende wasserfreie Reaktionsgemisch direkt für die Blockierung verwendet wird.From the German patent application DE 44 41 418 A1 is a process for the production of 3,5-Dimethylpyrazol-blocked Poylisocyanten known in which the Production of 3,5-dimethylpyrazole resulting anhydrous reaction mixture directly for the blocking is used.
Die bekannten, mit den vorstehend beschriebenen Pyrazolderivaten blockierten Di- und Polyisocyanate haben den Vorteil, daß sie bei vergleichsweise niedrigen Temperaturen deblockieren und mit isocyanatreaktiven funktionellen Gruppen reagieren, so daß entsprechende Beschichtungsstoffe, Klebstoffe und Dichtungsmassen bei Temperaturen unterhalb 160°C thermisch vernetzen.The known di- and blocked with the pyrazole derivatives described above Polyisocyanates have the advantage that they operate at comparatively low temperatures deblock and react with isocyanate-reactive functional groups, so that corresponding coating materials, adhesives and sealants at temperatures Cross-link thermally below 160 ° C.
Wegen der Vorteilhaftigkeit der Pyrazolblockierung von Di- und Polyisocyanaten ist es aber in hohem Maße wünschenswert, möglichst viele unterschiedlich substituierte Pyrazolderivate zur Verfügung zu haben, um das Eigenschaftsprofil der blockierten Polyisocanate und der hiermit hergestellten Beschichtungsstoffe, Klebstoffe und Dichtungsmassen und letztlich der entsprechenden Beschichtungen, Klebschichten und Dichtungen breit zu variieren und den Erfordernisssen des Einzelfalls gezielt anzupassen. Because of the advantage of pyrazole blocking of di- and polyisocyanates, it is but highly desirable, as many differently substituted ones as possible Pyrazole derivatives available to have the property profile of the blocked Polyisocanate and the coating materials, adhesives and Sealing compounds and ultimately the corresponding coatings, adhesive layers and Varying the seals widely and adapting them to the requirements of the individual case.
Aufgabe der vorliegenden Erfindung ist es, neue, mit substituierten Pyrazolen blockierte Di- und Polyisocyanate bereitzustellen, die das vorteilhafte Eigenschaftsprofil der bisher bekannten blockierten Di- und Polyisocyanate aufweisen, wenn nicht gar dieses übertreffen und die die Herstellung neuer vorteilhafter Beschichtungsstoffe, Klebstoffe und Dichtungsmassen sowie neuer Beschichtungen, Klebschichten und Dichtungen gestatten.The object of the present invention is to create new, blocked with substituted pyrazoles To provide di- and polyisocyanates that have the advantageous property profile of the previous known blocked di- and polyisocyanates, if not this surpass and which the production of new advantageous coating materials, adhesives and Allow sealing compounds as well as new coatings, adhesive layers and seals.
Demgemäß wurden die neuen, mit in 3,4-Stellung disubstituierten Pyrazolen blockierten Di- und Polyisocyanate gefunden, die im folgenden als "erfindungsgemäße blockierte Di- und Polyisocyanate" bezeichnet werden.Accordingly, the new pyrazoles blocked with 3,4-disubstituted were blocked Found di- and polyisocyanates, which are hereinafter referred to as "blocked di- and polyisocyanates ".
Außerdem wurden die neuen Beschichtungsstoffe, Klebstoffe und Dichtungsmassen gefunden, die die erfindungsgemäßen blockierten Di- und Polyisocyanate enhalten und die im folgenden als "erfindungsgemäße Beschichtungsstoffe, Klebstoffe und Dichtungsmassen" bezeichnet werden.In addition, the new coating materials, adhesives and sealants found which contain the blocked di- and polyisocyanates according to the invention and which hereinafter referred to as "coating materials, adhesives and Sealants "are referred to.
Des weiteren wurden die neuen Beschichtungen, Klebschichten und Dichtungen gefunden, die mit Hilfe der erfindungsgemäßen Beschichtungsstoffe, Klebstoffe und Dichtungsmassen erhalten werden und die im folgenden als "erfindungsgemäße Beschichtungen, Klebschichten und Dichtungen" bezeichnet werden.Furthermore, the new coatings, adhesive layers and seals were found, with the help of the coating materials, adhesives and Sealants are obtained and the following as "inventive Coatings, adhesive layers and seals "are referred to.
Weitere erfindungsgemäße Gegenstände gehen aus der Beschreibung hervor.Further objects according to the invention are evident from the description.
Die erfindungsgemäß zu verwendenden, in 3,4-Stellung disubstituierten Pyrazole werden im folgenden der Kürze halber als "erfindungsgemäß zu verwendende Pyrazole" bezeichnet.The pyrazoles disubstituted in the 3,4-position to be used according to the invention are in the following, for brevity, as "pyrazoles to be used according to the invention" designated.
Die erfindungsgemäß zu verwendenden Pyrazole sind disubstituiert. Hierbei kann ein solches Pyrazol zwei gleiche oder zwei von einander verschiedene Substituenten tragen. Welche Variante im Einzelfall gewählt wird, richtet sich zum einen nach der Zugänglichkeit der Ausgangsprodukte, der Ausbeute bei der Herstellung und dem für die Anwendung erforderlichen Eignschaftsprofil. The pyrazoles to be used according to the invention are disubstituted. Here, a such pyrazole carry two identical or two different substituents. Which variant is chosen in the individual case depends on the one hand on the Accessibility of the starting products, the yield in the production and that for the Application required property profile.
Als Substituenten kommen grundsätzlich alle Atome, ausgenommen Wasserstoffatome, elektronenziehende oder elektronenschiebende Gruppen und organischen Reste, inklusive elementorganischen Reste, in Betracht, sofern sie nicht selbst unter den Bedingungen der Herstellung der erfindungsgemäßen Di- und Polyisocyanate und/oder der thermischen Härtung mit Isocyanaten reagieren und so die gewünschte Blockierungsreaktion und/oder die thermische Vernetzung stören oder ganz verhindern. Vorzugsweise erhöhen die Substituenten nicht die Deblockierungstemperatur.Basically, all atoms come apart from hydrogen atoms, electron-withdrawing or electron-donating groups and organic residues, inclusive elemental organic residues, if they are not themselves under the conditions of Production of the di- and polyisocyanates according to the invention and / or the thermal ones React curing with isocyanates and thus the desired blocking reaction and / or disrupt or completely prevent thermal networking. Preferably increase the Substituents not the deblocking temperature.
Beispiele geeigneter Atome sind Halogenatome, insbesondere Fluor, Chlor und Brom.Examples of suitable atoms are halogen atoms, in particular fluorine, chlorine and bromine.
Beispiele elektronenziehender oder elektronenschiebender Gruppen sind Nitro- oder Nitrilgruppen; Carbonsäure-, Sulfonsäure- oder Phosphonsäuregruppen; Carboxylat-, Sulfonat- oder Phosphonatgruppen; Carbonsäure-, Sulfonsäure- oder Phosphonsäureester, die die nachstehend beschriebenen substituierten und unsubstituierten Alkyl-, Cycloalkyl-, Alkylcycloalkyl-, Cycloalkylalkyl-, Aryl-, Alkylaryl-, Cycloalkylaryl- Arylalkyl- oder Arylcycloalkylreste enthalten; primäre, sekundäre, oder tertiäre Amidgruppen oder quaternäre Ammoniumgruppen, die die nachstehend beschriebenen substituierten und unsubstituierten Alkyl-, Cycloalkyl-, Alkylcycloalkyl-, Cycloalkylalkyl-, Aryl-, Alkylaryl-, Cycloalkylaryl-, Arylalkyl- oder Arylcycloalkylreste enthalten; sowie Harnstoffgruppen.Examples of electron-withdrawing or electron-donating groups are nitro or Nitrile groups; Carboxylic acid, sulfonic acid or phosphonic acid groups; Carboxylate, Sulfonate or phosphonate groups; Carboxylic acid, sulfonic acid or phosphonic acid esters, the substituted and unsubstituted alkyl, cycloalkyl, Alkylcycloalkyl, cycloalkylalkyl, aryl, alkylaryl, cycloalkylaryl, arylalkyl or Contain arylcycloalkyl radicals; primary, secondary, or tertiary amide groups or quaternary ammonium groups which are substituted and described below unsubstituted alkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, alkylaryl, Contain cycloalkylaryl, arylalkyl or arylcycloalkyl radicals; as well as urea groups.
Beispiele geeigneter organischer Reste sind substituierte und unsubstituierte Alkyl-, Cycloalkyl-, Alkylcycloalkyl-, Cycloalkylalkyl-, Aryl-, Alkylaryl-, Cycloalkylaryl-, Arylalkyl- oder Arylcycloalkylreste.Examples of suitable organic radicals are substituted and unsubstituted alkyl, Cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, alkylaryl, cycloalkylaryl, Arylalkyl or arylcycloalkyl radicals.
Beispiele geeigneter Alkylreste sind Methyl, Ethyl, Propyl, Isopropyl, n-Butyl, iso-Butyl, tert.-Butyl, Amyl, Hexyl oder 2-Ethylhexyl.Examples of suitable alkyl radicals are methyl, ethyl, propyl, isopropyl, n-butyl, iso-butyl, tert-butyl, amyl, hexyl or 2-ethylhexyl.
Beispiele geeigneter Cycloalkylreste sind Cyclobutyl, Cyclopentyl oder Cyclohexyl.Examples of suitable cycloalkyl radicals are cyclobutyl, cyclopentyl or cyclohexyl.
Beispiele geeigneter Alkylcycloalkylreste sind Methylencyclohexan, Ethylencyclohexan oder Propan-1,3-diyl-cyclohexan.Examples of suitable alkylcycloalkyl radicals are methylene cyclohexane and ethylene cyclohexane or propane-1,3-diyl-cyclohexane.
Beispiele geeigneter Cycloalkylalkylreste sind 2-, 3- oder 4-Methyl-, -Ethyl-, -Propyl- oder -Butylcyclohex-1-yl. Examples of suitable cycloalkylalkyl radicals are 2-, 3- or 4-methyl, ethyl, propyl or -Butylcyclohex-1-yl.
Beispiele geeigneter Arylreste sind Phenyl, Naphthyl oder Biphenylyl, vorzugsweise Phenyl und Naphthyl und insbesondere Phenyl.Examples of suitable aryl radicals are phenyl, naphthyl or biphenylyl, preferably Phenyl and naphthyl and especially phenyl.
Beispiele geeigneter Alkylarylreste sind Benzyl oder Ethylen- oder Propan-1,3-diyl benzol.Examples of suitable alkylaryl radicals are benzyl or ethylene or propane-1,3-diyl benzene.
Beispiele geeigneter Cycloalkylarylreste sind 2-, 3-, oder 4-Phenylcyclohex-1-yl.Examples of suitable cycloalkylaryl radicals are 2-, 3-, or 4-phenylcyclohex-1-yl.
Beispiele geeigneter Arylalkylreste sind 2-, 3- oder 4-Methyl-, -Ethyl-, -Propyl- oder - Butylphen-1-yl.Examples of suitable arylalkyl radicals are 2-, 3- or 4-methyl-, -ethyl-, -propyl- or - Butylphen-1-yl.
Beispiele geeigneter Arylcycloalkylreste sind 2-, 3- oder 4-Cyclohexylphen-1-yl.Examples of suitable arylcycloalkyl radicals are 2-, 3- or 4-cyclohexylphen-1-yl.
Die vorstehend genannten Alkyl-, Cycloalkyl-, Alkylcycloalkyl-, Cycloalkylalkyl-, Aryl-, Alkylaryl-, Cycloalkylaryl-, Arylalkyl- und Arylcycloalkylreste können mit den vorstehend genannten Atomen und elektronenschiebenden oder elektronenziehenden Gruppen, insbesondere mit Chlor- und/oder Fluoratomen, und/oder mit den nachstehend beschriebenen elementorganischen Resten partiell oder vollständig substituiert sein.The aforementioned alkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, Alkylaryl, cycloalkylaryl, arylalkyl and arylcycloalkyl radicals can be with the above mentioned atoms and electron-donating or electron-withdrawing groups, in particular with chlorine and / or fluorine atoms, and / or with the following described elemental organic radicals can be partially or completely substituted.
Beispiele geeigneter elementorganischer Reste sind Aryloxy-, Alkyloxy- und Cycloalkyloxyreste, insbesondere Phenoxy-, Naphthoxy-, Methoxy-, Ethoxy-, Propoxy-, Butyloxy- oder Cyclohexyloxyreste; Polyetherreste wie Di-, TH-, Tetra- oder Pentaethylen- oder -propylenglykolreste; Arylthio-, Alkylthio- und Cycloalkylthioreste, insbesondere Phenylthio-, Naphthylthio-, Methylthio-, Ethylthio-, Propylthio-, Butylthio- oder Cyclohexylthioreste; Silylreste, die die vorstehend beschriebenen substituierten und unsubstituierten Alkyl-, Cycloalkyl-, Alkylcycloalkyl-, Cycloalkylalkyl-, Aryl-, Alkylaryl-, Cycloalkylaryl-, Arylalkyl- oder Arylcycloalkylreste und/oder Aryloxy-, Alkyloxy- und Cycloalkyloxyreste enthalten; wie Trimethyl-, Tripropyl-, Triethyl-, Dimethylethyl-, Diethylmethyl-, Trimethoxy, Dimethoxyethyl-, Triethoxy-, Tripropoxy- oder Propoxydimethylsilylreste; oder tertiäre Sulfoniumgruppen, die die vorstehend beschriebenen substituierten und unsubstituierten Alkyl-, Cycloalkyl-, Alkylcycloalkyl-, Cycloalkylalkyl-, Aryl-, Alkylaryl-, Cycloalkylaryl-, Arylalkyl- oder Arylcycloalkylreste enthalten. Examples of suitable elemental organic radicals are aryloxy, alkyloxy and Cycloalkyloxy radicals, in particular phenoxy, naphthoxy, methoxy, ethoxy, propoxy, Butyloxy or cyclohexyloxy radicals; Polyether residues such as di, TH, tetra or Pentaethylene or propylene glycol residues; Arylthio, alkylthio and cycloalkylthio radicals, especially phenylthio, naphthylthio, methylthio, ethylthio, propylthio, butylthio or cyclohexylthio residues; Silyl radicals that are substituted and described above unsubstituted alkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, alkylaryl, Cycloalkylaryl, arylalkyl or arylcycloalkyl radicals and / or aryloxy, alkyloxy and Contain cycloalkyloxy radicals; such as trimethyl, tripropyl, triethyl, dimethylethyl, Diethylmethyl, trimethoxy, dimethoxyethyl, triethoxy, tripropoxy or Propoxydimethylsilyl residues; or tertiary sulfonium groups which meet the above Substituted and unsubstituted alkyl, cycloalkyl, alkylcycloalkyl, Cycloalkylalkyl, aryl, alkylaryl, cycloalkylaryl, arylalkyl or arylcycloalkyl radicals contain.
Bevorzugte Substituenten sind unsubstituierte Alkyl-, Cycloalkyl-, Alkylcycloalkyl-, Cycloalkylalkyl-, Aryl-, Alkylaryl-, Cycloalkylaryl-, Arylalkyl- oder ArylcycloalkylrestePreferred substituents are unsubstituted alkyl, cycloalkyl, alkylcycloalkyl, Cycloalkylalkyl, aryl, alkylaryl, cycloalkylaryl, arylalkyl or arylcycloalkyl radicals
Besonders bevorzugte Substituenten sind unsubstituierte Alkylreste, insbesondere die niedrigen Alkyreste wie Methyl, Ethyl, Propyl, Isopropyl, n-Butyl, iso-Butyl, tert.-Butyl. Von diesen bieten die Methylreste wiederum die meisten Vorteile und werden deshalb ganz besonders bevorzugt verwendet.Particularly preferred substituents are unsubstituted alkyl radicals, especially those lower alkyl radicals such as methyl, ethyl, propyl, isopropyl, n-butyl, iso-butyl, tert-butyl. Of these, the methyl residues in turn offer the most advantages and are therefore used very particularly preferably.
Demgemäß handelt es sich bei dem erfindungsgemäß ganz besonders bevorzugt verwendeten Pyrazol um 3,4-Dimethylpyrazol.Accordingly, it is particularly preferred according to the invention used pyrazole around 3,4-dimethylpyrazole.
Die erfindungsgemäß zu verwendenden Pyrazole, insbesondere 3,4-Dimethylpyrazol, sind bekannte Verbindungen und können nach den üblichen und bekannten Methoden der Herstellung substituierter Pyrazole beispielsweise aus geeigneten 1,3- Dicarbonylverbindungen und Hydrazin synthetisiert werden.The pyrazoles to be used according to the invention, in particular 3,4-dimethylpyrazole, are known compounds and can by the usual and known methods of Production of substituted pyrazoles, for example from suitable 1,3- Dicarbonyl compounds and hydrazine can be synthesized.
Als zu blockierende Diisocyanate und Polyisocyanate kommen praktisch alle üblichen und bekannten aromatischen, aliphatischen und cycloaliphatischen Di- und Polyisocyanate, in Betracht. Insbesondere kommen die Diisocyanate und Polyisocyanate in Betracht, die von der Fachwelt als Lackpolyisocyanate bezeichnet werden.The diisocyanates and polyisocyanates to be blocked are practically all customary and known aromatic, aliphatic and cycloaliphatic di- and polyisocyanates, in Consideration. In particular, the diisocyanates and polyisocyanates come into consideration referred to in the art as paint polyisocyanates.
Beispiele geeigneter zu blockierender aromatischer Diisocyanate sind Toluylendiisocyanat, Xylylendiisocyanat, Bisphenylendiisocyanat, Naphthylendiisocyanat oder Diphenylmethandiisocyanat.Examples of suitable aromatic diisocyanates to be blocked are tolylene diisocyanate, Xylylene diisocyanate, bisphenylene diisocyanate, naphthylene diisocyanate or Diphenylmethane diisocyanate.
Beispiele geeigneter zu blockierender acyclischer aliphatischer Diisocyanate sind Tri methylendiisocyanat, Tetramethylendiisocyanat, Pentamethylendiisocyanat, Hexamethylendiisocyanat, Ethylethylendiisocyanat, Trimethylhexandiisocyanat, Heptamethylendiisocyanat, 4-Isocyanatomethyl-1,8-octamethylen-diisocyanat, oder Diisocyanate, abgeleitet von Dimerfettsäuren, wie sie unter der Handelsbezeichnung DDI 1410 von der Firma Henkel vertrieben und in den Patentschriften WO 97/49745 und WO 97/49747 beschrieben werden, insbesondere 2-Heptyl-3,4-bis(9-isocyanatononyl)-1- pentyl-cyclohexan, oder 1,2-, 1,4- oder 1,3-Bis(isocyanatomethyl)cyclohexan, 1,2-, 1,4- oder 1,3-Bis(2-isocyanatoeth-1-yl)cyclohexan, 1,3-Bis(3-isocyanatoprop-1-yl)cyclohexan oder 1,2-, 1,4- oder 1,3-Bis(4-isocyanatobut-1-yl)cyclohexan.Examples of suitable acyclic aliphatic diisocyanates to be blocked are tri methylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, Hexamethylene diisocyanate, ethylethylene diisocyanate, trimethylhexane diisocyanate, Heptamethylene diisocyanate, 4-isocyanatomethyl-1,8-octamethylene diisocyanate, or Diisocyanates derived from dimer fatty acids, such as those under the trade name DDI 1410 sold by the Henkel company and in the patents WO 97/49745 and WO 97/49747 be described, in particular 2-heptyl-3,4-bis (9-isocyanatononyl) -1- pentyl-cyclohexane, or 1,2-, 1,4- or 1,3-bis (isocyanatomethyl) cyclohexane, 1,2-, 1,4- or 1,3-bis (2-isocyanatoeth-1-yl) cyclohexane, 1,3-bis (3-isocyanatoprop-1-yl) cyclohexane or 1,2-, 1,4- or 1,3-bis (4-isocyanatobut-1-yl) cyclohexane.
Beispiele geeigneter cycloaliphatischer Diisocyanate sind Isophorondiisocyanat (= 5- Isocyanato-1-isocyanatomethyl-1,3,3-trimethyl-cyclohexan), 5-Isocyanato-1-(2- isocyanatoeth-1-yl)-1,3,3-trimethyl-cyclohexan, 5-Isocyanato-1-(3-isocyanatoprop-1-yl)- 1,3,3-trimethyl-cyclohexan, 5-Isocyanato-(4-isocyanatobut-1-yl)-1,3,3-trimethyl- cyclohexan, 1-Isocyanato-2-(3-isocyanatoprop-1-yl)-cyclohexan, 1-Isocyanato-2-(3- isocyanatoeth-1-yl)cyclohexan, 1-Isocyanato-2-(4-isocyanatobut-1-yl)-cyclohexan, 1,2- Diisocyanatocyclobutan, 1,3-Diisocyanatocyclobutan, 1,2-Diisocyanatocyclopentan, 1,3- Diisocyanatocyclopentan, 1,2-Diisocyanatocyclohexan, 1,3-Diisocyanatocyclohexan, 1,4- Diisocyanatocyclohexan Dicyclohexylmethan-2,4'-diisocyanat oder Dicyclohexylmethan- 4,4'-diisocyanat, insbesondere Isophorondiisocyanat.Examples of suitable cycloaliphatic diisocyanates are isophorone diisocyanate (= 5- Isocyanato-1-isocyanatomethyl-1,3,3-trimethyl-cyclohexane), 5-isocyanato-1- (2- isocyanatoeth-1-yl) -1,3,3-trimethyl-cyclohexane, 5-isocyanato-1- (3-isocyanatoprop-1-yl) - 1,3,3-trimethyl-cyclohexane, 5-isocyanato- (4-isocyanatobut-1-yl) -1,3,3-trimethyl- cyclohexane, 1-isocyanato-2- (3-isocyanatoprop-1-yl) cyclohexane, 1-isocyanato-2- (3- isocyanatoeth-1-yl) cyclohexane, 1-isocyanato-2- (4-isocyanatobut-1-yl) cyclohexane, 1,2- Diisocyanatocyclobutane, 1,3-diisocyanatocyclobutane, 1,2-diisocyanatocyclopentane, 1,3- Diisocyanatocyclopentane, 1,2-diisocyanatocyclohexane, 1,3-diisocyanatocyclohexane, 1,4- Diisocyanatocyclohexane, dicyclohexylmethane-2,4'-diisocyanate or dicyclohexylmethane 4,4'-diisocyanate, especially isophorone diisocyanate.
Beispiele geeigneter zu blockierender Polyisocyanate sind isocyanatgruppenhaltige Polyurethanpräpolymere, die durch Reaktion von Polyolen mit einem Überschuß der vorstehend beschriebenen aromatischen, aliphatischen und cycloaliphatischen, vorzugsweise aliphatischen und cycloaliphatischen, Diisocyanaten hergestellt werden können und bevorzugt niederviskos sind. Im Rahmen der vorliegenden Erfindung bezeichnet der Begriff "cycloaliphatisches Diisocyanat" ein Diisocyanat, worin mindestens eine Isocyanatgruppe an einen cycloaliphatischen Rest gebunden ist.Examples of suitable polyisocyanates to be blocked are those containing isocyanate groups Polyurethane prepolymers obtained by reacting polyols with an excess of aromatic, aliphatic and cycloaliphatic, described above, preferably aliphatic and cycloaliphatic, diisocyanates can and are preferably low viscosity. Within the scope of the present invention the term "cycloaliphatic diisocyanate" denotes a diisocyanate in which at least one isocyanate group is attached to a cycloaliphatic radical.
Es können auch Isocyanurat-, Biuret-, Allophanat-, Iminooxadiazindion-, Urethan-, Harnstoff-, Carbodiimid und/oder Uretdiongruppen aufweisende Polyisocyanate verwendet werden, die in üblicher und bekannter Weise aus den vorstehend beschriebenen Diisocyanaten hergestellt werden. Beispiele geeigneter Herstellungsverfahren und Polyisocyanate sind beispielsweise aus den Patentschriften und Patentanmeldungen CA 2,163,591 A1, US 4,419,513 A1, US 4,454,317 A1, EP 0 646 608 A1, US 4,801,675 A1, EP 0 183 976 A1, DE 40 15 155 A1, EP 0 303 150 A1, EP 0 496 208 A1, EP 0 524 500 A1, EP 0 566 037 A1, US 5,258,482 A1, US 5,290,902 A1, EP 0 649 806 A1, DE 42 29 183 A1 oder EP 0 531 820 A1 bekannt.Isocyanurate, biuret, allophanate, iminooxadiazinedione, urethane, Polyisocyanates containing urea, carbodiimide and / or uretdione groups are used be, which in a conventional and known manner from those described above Diisocyanates are produced. Examples of suitable manufacturing processes and Polyisocyanates are known, for example, from the patents and patent applications CA 2,163,591 A1, US 4,419,513 A1, US 4,454,317 A1, EP 0 646 608 A1, US 4,801,675 A1, EP 0 183 976 A1, DE 40 15 155 A1, EP 0 303 150 A1, EP 0 496 208 A1, EP 0 524 500 A1, EP 0 566 037 A1, US 5,258,482 A1, US 5,290,902 A1, EP 0 649 806 A1, DE 42 29 183 A1 or EP 0 531 820 A1.
Außerdem kommen noch niedermolekulare, oligomere und polymere Verbindungen in Betracht, die Isocyanatgruppen und Gruppen enthalten, die mit aktinischer Strahlung, insbesondere UV-Licht oder Elektronenstrahlung aktiviert werden. Beispiele geeigneter Verbindungen dieser Art sind die in der europäischen Patentanmeldung EP 0 928 800 A1 beschriebenen Urethan(meth)acrylate, die (Meth)Acrylatgruppen und freie Isocyanatgruppen aufweisen.In addition, low molecular weight, oligomeric and polymeric compounds also come in Consider that contain isocyanate groups and groups that are exposed to actinic radiation, in particular UV light or electron radiation can be activated. Examples of more suitable Compounds of this type are those in European patent application EP 0 928 800 A1 described urethane (meth) acrylates, the (meth) acrylate groups and free Have isocyanate groups.
Im Rahmen der vorliegenden Erfindung werden hier und im folgenden unter Oligomeren Harze verstanden, die mindestens 2 bis 15 Monomereinheiten in ihrem Molekül enthalten. Im Rahmen der vorliegenden Erfindung werden unter Polymeren Harze verstanden, die mindestens 10 Monomereinheiten in ihrem Molekül enthalten. Ergänzend wird zu diesen Begriffen auf Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, "Oligomere", Seite 425, verwiesen.In the context of the present invention, here and below, among oligomers Resins understood that contain at least 2 to 15 monomer units in their molecule. In the context of the present invention, polymers are understood to be resins which contain at least 10 monomer units in their molecule. Complementary to these Terms in Römpp Lexicon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, "Oligomers", page 425.
Erfindungsgemäß werden die vorstehend beschriebenen Di- und Polyisocyanate partiell oder vollständig mit den erfindungsgemäß zu verwendenden Pyrazolen blockiert.According to the invention, the di- and polyisocyanates described above are partial or completely blocked with the pyrazoles to be used according to the invention.
Die partielle Blockierung mit den erfindungsgemäß zu verwendenden Pyrazolen wird angewandt, wenn die Di- und Polyisocyanate noch mit weiteren geeigneten Blockierungsmitteln blockiert werden sollen, um besondere technische Effekte bei der Deblockierung und Vernetzung zu realisieren.The partial blocking with the pyrazoles to be used according to the invention becomes applied if the di- and polyisocyanates with other suitable Blocking agents should be blocked in order to achieve special technical effects Realizing deblocking and networking.
Beispiele geeigneter üblicher und bekannter Blockierungsmittel sind die aus der US-
Patentschrift US-A-4,444,954 bekannten:
Examples of suitable customary and known blocking agents are those known from US Pat. No. 4,444,954:
- a) Phenole wie Phenol, Cresol, Xylenol, Nitrophenol, Chlorophenol, Ethylphenol, t- Butylphenol, Hydroxybenzoesäure, Ester dieser Säure oder 2,5-di-tert.-Butyl-4- hydroxytoluol;a) phenols such as phenol, cresol, xylenol, nitrophenol, chlorophenol, ethylphenol, t- Butylphenol, hydroxybenzoic acid, esters of this acid or 2,5-di-tert-butyl-4- hydroxytoluene;
- b) Lactame, wie ε-Caprolactam, δ-Valerolactam, γ-Butyrolactam oder β- Propiolactam;b) lactams, such as ε-caprolactam, δ-valerolactam, γ-butyrolactam or β- Propiolactam;
- c) aktive methylenische Verbindungen, wie Diethylmalonat, Dimethylmalonat, Acetessigsäureethyl- oder -methylester oder Acetylaceton; c) active methylenic compounds, such as diethyl malonate, dimethyl malonate, Ethyl or methyl acetoacetate or acetylacetone;
- d) Alkohole wie Methanol, Ethanol, n-Propanol, Isopropanol, n-Butanol, Isobutanol, t-Butanol, n-Amylalkohol, t-Amylalkohol, Laurylalkohol, Ethylenglykolmonomethylether, Ethylenglykolmonoethylether, Ethylenglykolmonopropylether Ethylenglykolmonobutylether, Diethylenglykolmonomethylether, Diethylenglykolmonoethylether, Propylenglykolmonomethylether; Methoxymethanol, Glykolsäure, Glykolsäureester, Milchsäure, Milchsäureester, Methylolharnstoff, Methylolmelamin, Diacetonalkohol, Ethylenchlorohydrin, Ethylenbromhydrin, 1,3- Dichloro-2-propanol, 1,4-Cyclohexyldimethanol oder Acetocyanhydrin;d) alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, n-amyl alcohol, t-amyl alcohol, lauryl alcohol, Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, Ethylene glycol monopropyl ether ethylene glycol monobutyl ether, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Propylene glycol monomethyl ether; Methoxymethanol, glycolic acid, Glycolic acid esters, lactic acid, lactic acid esters, methylol urea, Methylolmelamine, diacetone alcohol, ethylene chlorohydrin, ethylene bromohydrin, 1,3- Dichloro-2-propanol, 1,4-cyclohexyldimethanol or acetocyanhydrin;
- e) Mercaptane wie Butylmercaptan, Hexylmercaptan, t-Butylmercaptan, t- Dodecylmercaptan, 2-Mercaptobenzothiazol, Thiophenol, Methylthiophenol oder Ethylthiophenol;e) mercaptans such as butyl mercaptan, hexyl mercaptan, t-butyl mercaptan, t- Dodecyl mercaptan, 2-mercaptobenzothiazole, thiophenol, methylthiophenol or Ethylthiophenol;
- f) Säureamide wie Acetoanilid, Acetoanisidinamid, Acrylamid, Methacrylamid, Essigsäureamid, Stearinsäureamid oder Benzamid;f) acid amides such as acetoanilide, acetoanisidinamide, acrylamide, methacrylamide, Acetic acid amide, stearic acid amide or benzamide;
- g) Imide wie Succinimid, Phthalimid oder Maleimid;g) imides such as succinimide, phthalimide or maleimide;
- h) Amine wie Diphenylamin, Phenylnaphthylamin, Xylidin, N-Phenylxylidin, Carbazol, Anilin, Naphthylamin, Butylamin, Dibutylamin oder Butylphenylamin;h) amines such as diphenylamine, phenylnaphthylamine, xylidine, N-phenylxylidine, Carbazole, aniline, naphthylamine, butylamine, dibutylamine or butylphenylamine;
- i) Imidazole wie Imidazol oder 2-Ethylimidazol;i) imidazoles such as imidazole or 2-ethylimidazole;
- j) Harnstoffe wie Harnstoff, Thioharnstoff, Ethylenharnstoff, Ethylenthioharnstoff oder I,3-Diphenylharnstoff;j) ureas such as urea, thiourea, ethylene urea, ethylene thiourea or 1,3-diphenylurea;
- k) Carbamate wie N-Phenylcarbamidsäurephenylester oder 2-Oxazolidon;k) carbamates such as phenyl N-phenylcarbamate or 2-oxazolidone;
- l) Imine wie Ethylenimin;l) imines such as ethyleneimine;
- m) Oxime wie Acetonoxim, Formaldoxim, Acetaldoxim, Acetoxim, Methylethylketoxim, Diisobutylketoxim, Diacetylmonoxim, Benzophenonoxim oder Chlorohexanonoxime; m) oximes such as acetone oxime, formal doxime, acetaldoxime, acetoxime, Methyl ethyl ketoxime, diisobutyl ketoxime, diacetyl monoxime, benzophenone oxime or chlorohexanone oximes;
- n) Salze der schwefeligen Säure wie Natriumbisulfit oder Kaliumbisulfit;n) salts of sulfurous acid such as sodium bisulfite or potassium bisulfite;
- o) Hydroxamsäureester wie Benzylmethacrylohydroxamat (BMH) oder Allylmethacrylohydroxamat; odero) hydroxamic acid esters such as benzyl methacrylohydroxamate (BMH) or Allyl methacrylohydroxamate; or
- p) substituierte Pyrazole wie 3,5-Dimethylpyrazol, Imidazole oder Triazole.p) substituted pyrazoles such as 3,5-dimethylpyrazole, imidazoles or triazoles.
Diese üblichen und bekannten Blockierungsmittel werden indes nur in untergeordneten Mengen angewandt. Dies bedeutet, daß die für die Anwendung in den erfindungsgemäßen Beschichtungsstoffen, Klebstoffen und Dichtungsmassen wesentlichen anwendungstechnischen Eigenschaften wie die Einbrenntemperatur in der Hauptsache von den erfindungsgemäß zu verwendenden Pyrazolen bestimmt wird.However, these customary and known blocking agents are only used in subordinate ones Amounts applied. This means that for use in the invention Coating materials, adhesives and sealants essential application properties such as the baking temperature in the main of the pyrazoles to be used according to the invention is determined.
Außerdem wird die partielle Blockierung mit den erfindungsgemäß zu verwendenden Pyrazolen angewandt, wenn die betreffenden partiell blockierten Di- und Polyisocyanate in thermisch oder thermisch und mit aktinischer Strahlung härtbare Bindemittel eingebaut werden sollen. Zweckmäßigerweise erfolgt dies über die Reaktion von in den Bindemitteln vorhandenen isocyanatreaktiven funktionellen Gruppen, wie primäre Aminogruppen, Hydroxylgruppen und/oder Thiolgruppen, insbesondere Hydroxylgruppen, mit den freien Isocyananatgruppen. Durch den Einbau erhalten die Bindemittel selbstvernetzende Eigenschaften.In addition, the partial blocking with those to be used according to the invention Pyrazoles applied when the partially blocked di- and polyisocyanates in question Binder that is curable thermally or thermally and with actinic radiation should be. This is expediently carried out via the reaction of in the binders existing isocyanate-reactive functional groups, such as primary amino groups, Hydroxyl groups and / or thiol groups, especially hydroxyl groups, with the free Isocyananate groups. By installing the binders get self-crosslinking Characteristics.
Im Rahmen der vorliegenden Erfindung bezeichnet der Begriff "selbstvernetzend" die Eigenschaft eines Bindemittels (zu den Begriff vgl. Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, "Bindemittel", Seiten 73 und 74) mit sich selbst Vernetzungsreaktionen einzugehen. Voraussetzung hierfür ist, das in den Bindemitteln bereits beide Arten von komplementären reaktiven funktionellen Gruppen, hier die in erfindungsgemäßer Weise blockierten Isocyanatgruppen und die isocyanatreaktiven Gruppen, enthalten sind, die für eine Vernetzung notwendig sind.In the context of the present invention, the term “self-crosslinking” denotes the Property of a binder (for the term see Römpp Lexikon Lacke and Printing inks, Georg Thieme Verlag, Stuttgart, New York, 1998, "Binders", pages 73 and 74) engage in cross-linking reactions with themselves. The prerequisite for this is that Both types of complementary reactive functional already in the binders Groups, here the isocyanate groups blocked in the manner according to the invention and the Isocyanate-reactive groups are included, which are necessary for crosslinking.
Als fremdvernetzend werden dagegen solche Beschichtungsstoffe, Klebstoffe und Dichtungsmassen bezeichnet, worin die eine Art der komplementären reaktiven funktionellen Gruppen, hier die isocyanatreaktiven, in dem Bindemittel, und die andere Art in einem Härter oder Vernetzungsmittel, hier dem erfindungsgemäßen blockierten Polyisocyanat, vorliegen. Ergänzend wird hier zur auf Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, "Härtung", Seiten 274 bis 276, insbesondere Seite 275, unten, verwiesen.Such coating materials, adhesives and Sealants referred to, wherein the one type of complementary reactive functional groups, here the isocyanate-reactive, in the binder, and the other type in a hardener or crosslinking agent, here the blocked according to the invention Polyisocyanate. In addition, here on the Römpp Lexicon Lacke and Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, "Hardening", pages 274 to 276, especially page 275, below.
Außerdem wird die partielle Blockierung mit den erfindungsgemäß zu verwendenden Pyrazolen angewandt, wenn die betreffenden partiell blockierten Di- und Polyisocyanate als Vernetzungsmittel in Zwei- oder Mehrkomponentensystemen angewandt werden sollen. Bei erfindungsgemäßen Beschichtungsmitteln, Klebstoffen und Dichtungsmassen dieser Art werden die Vernetzungsmittel aufgrund ihrer hohen Reaktivität bis zur Anwendung getrennt von den übrigen Bestandteilen gelagert und erst kurz vor der Anwendung mit diesen vermischt.In addition, the partial blocking with those to be used according to the invention Pyrazoles applied when the partially blocked di- and polyisocyanates in question can be used as crosslinking agents in two- or multi-component systems should. In the case of coating compositions, adhesives and sealants according to the invention this type of crosslinking agents are due to their high reactivity up to Application stored separately from the other ingredients and only shortly before Application mixed with these.
Vorzugsweise werden die Di- und Polyisocyanate vollständig mit den erfindungsgemäß zu verwendenden Pyrazolen blockiert.The di- and polyisocyanates are preferably added completely with those according to the invention using pyrazoles blocked.
Methodisch gesehen weist die erfindungsgemäße Blockierung keine Besonderheiten auf, sondern erfolgt durch stöchiometrische Umsetzung der zu blockierenden Di- und Polyisocyanate mit den erfindungsgemäß zu verwendenden Pyrazolen in der Schmelze oder in mindestens einem gegenüber Isocyanaten im wesentlichen inerten organischen Lösemittel vorzugsweise unter einer Schutzgasatmosphäre und in Gegenwart eines geeigneten Katalysators, wie es beispielsweise in der europäischen Patentschrift EP 0 159 117 B1 oder der deutschen Patentanmeldung DE 44 41 418 A1 für 3,5-Dimethylpyrazol beschrieben wird.From a methodological point of view, the blocking according to the invention has no special features, but is done by stoichiometric implementation of the di and to be blocked Polyisocyanates with the pyrazoles to be used according to the invention in the melt or in at least one organic which is essentially inert to isocyanates Solvent preferably under a protective gas atmosphere and in the presence of a suitable catalyst, as described, for example, in European Patent EP 0 159 117 B1 or the German patent application DE 44 41 418 A1 for 3,5-dimethylpyrazole is described.
Aufgrund ihrer besonderen vorteilhaften anwendungstechnischen Eigenschaften kommen die erfindungsgemäßen blockierten Di- und Polyisocyanate für alle Verwendungszwecke in Betracht, bei denen blockierte Di- und Polyisocyanate üblicherweise eingesetzt werden. Vorzugsweise werden sie als Vernetzungsmittel in den erfindungsgemäßen thermisch oder so thermisch und mit aktinischer Strahlung härtbaren Beschichtungsstoffen, Klebstoffen und Dichtungsmassen verwendet. Besonders bevorzugt werden sie in den erfindungsgemäßen Beschichtungsstoffen verwendet. Due to their special advantageous application properties the blocked di- and polyisocyanates according to the invention for all purposes into consideration, in which blocked di- and polyisocyanates are usually used. They are preferably used as crosslinking agents in the thermal or coating materials, adhesives and curable thermally with actinic radiation Sealants used. They are particularly preferred in the inventive Coating materials used.
Das nachstehend für die erfindungsgemäßen Beschichtungsstoffe Gesagte gilt für die erfindungsgemäßen Klebstoffe und Dichtungsmassen sinngemäß.The statements made below for the coating materials of the invention apply to the adhesives and sealants according to the invention analogously.
Der Gehalt der erfindungsgemäßen Beschichtungsstoffe an den erfindungsgemäßen Di- und Polyisocyanaten kann außerordentlich breit variieren. Da die erfindungsgemäßen Di- und Polyisocyanate die herkömmlichen blockierten Di- und Polyisocyanate in der Funktion der Vernetzungsmittel für thermisch und thermisch und mit aktinischer Strahlung härtbare Beschichtungsstoffen in vollem Umfang ersetzen können, können sie in den üblichen, vom Stand der Technik her bekannten Mengen angewandt werden. Indes können sie aufgrund ihrer vorteilhaften anwendungstechnischen Eigenschaften in vielen Fällen in geringeren Mengen eingesetzt werden.The content of the coating materials of the invention in the di- and polyisocyanates can vary widely. Since the di- and polyisocyanates function the conventional blocked di- and polyisocyanates the crosslinking agent for thermally and thermally curable with actinic radiation Can completely replace coating materials, they can in the usual, from Known amounts of prior art are used. However, they can their advantageous application properties in many cases in less Amounts are used.
Die erfindungsgemäßen Beschichtungsstoffe enthalten übliche und bekannte Bindemittel wie sie beispielsweise in Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, unter dem Stichwort "Bindemittel", Seiten 73 und 74, beschrieben werden. Gut geeignete Bindemittel sind statistisch, alternierend und/oder blockartig aufgebaute lineare und/oder verzweigte und/oder kammartig aufgebaute (Co)Polymerisate von ethylenisch ungesättigten Monomeren, oder Polyadditionsharze und/oder Polykondensationsharze wie sie in Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, Seite 457: "Polyaddition" und "Polyadditionsharze (Polyaddukte)", Seiten 463 und 464: "Polykondensate", "Polykondensation" und "Polykondensationsharze", beschrieben werden. Die Bindemittel enthalten die vorstehend beschriebenen isocyanatreaktiven funktionellen Gruppen. Darüber hinaus können sie weitere reaktive funktionelle Gruppen enthalten, die mit den komplementären reaktiven funktionellen Gruppen der gegebenenfalls vorhandenen üblichen und bekannten Vernetzungsmittel thermisch initiierte Vernetzungsreaktionen eingehen können. Ferner können sie Gruppen enthalten, die mit aktinischer Strahlung aktivierbar sind, wie Acrylatgruppen.The coating materials of the invention contain customary and known binders such as those in Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, Stuttgart, New York, 1998, under the keyword "binder", pages 73 and 74, to be discribed. Well-suited binders are statistical, alternating and / or linear and / or branched and / or comb-like structures (Co) polymers of ethylenically unsaturated monomers, or polyaddition resins and / or polycondensation resins as used in Römpp Lexikon lacquers and printing inks, Georg Thieme Verlag, Stuttgart, New York, 1998, page 457: "Polyaddition" and "Polyaddition Resins (Polyadducts)", pages 463 and 464: "Polycondensates", "Polycondensation" and "polycondensation resins" are described. The binders contain the isocyanate-reactive functional groups described above. About that In addition, they can contain other reactive functional groups that correspond to the complementary reactive functional groups of the optionally present usual and known crosslinking agents thermally initiated crosslinking reactions can enter into. They can also contain groups that are exposed to actinic radiation can be activated, such as acrylate groups.
Desweiteren können sie noch übliche und bekannte Vernetzungsmittel in untergeordneten Mengen enthalten, was bedeutet, daß die erfindungsgemäßen blockierten Di- und Polyisocyanate nach wie vor die Härtungseigenschaften der Beschichtungsstoffe in der Hauptsache bestimmen. Furthermore, you can still use conventional and known crosslinking agents in subordinate Contain amounts, which means that the blocked di- and Polyisocyanates still have the curing properties of the coating materials in the The main thing is to determine.
Beispiele geeigneter Vernetzungsmittel sind Aminoplastharze, wie sie beispielsweise in Römpp Lexikon Lacke und Druckfarben, Georg Thieme Verlag, 1998, Seite 29, "Aminoharze", dem Lehrbuch "Lackadditive" von Johan Bieleman, Wiley-VCH, Weinheim, New York, 1998, Seiten 242 ff., dem Buch "Paints, Coatings and Solvents", second completely revised edition, Edit. D. Stoye und W. Freitag, Wiley-VCH, Weinheim, New York, 1998, Seiten 80 ff., den Patentschriften US 4 710 542 A1 oder EP-B-0 245 700 A1 sowie in dem Artikel von B. Singh und Mitarbeiter "Carbamylmethylated Melamines, Novel Crosslinkers for the Coatings Industry", in Advanced Organic Coatings Science and Technology Series, 1991, Band 13, Seiten 193 bis 207, beschrieben werden, Carboxylgruppen enthaltende Verbindungen oder Harze, wie sie beispielsweise in der Patentschrift DE 196 52 813 A1 beschrieben werden, Epoxidgruppen enthaltende Verbindungen oder Harze, wie sie beispielsweise in den Patentschriften EP 0 299 420 A1, DE 22 14 650 B1, DE 27 49 576 B1, US 4,091,048 A1 oder US 3,781,379 A1 beschrieben werden, blockierte Polyisocyanate, wie sie beispielsweise in den Patentschriften US 4,444,954 A1, DE 196 17 086 A1, DE 196 31 269 A1, EP 0 004 571 A1 oder EP 0 582 051 A1 beschrieben werden, und/oder Tris(alkoxycarbonylamino)- triazine, wie sie in den Patentschriften US 4,939,213 A1, US 5,084,541 A1, US 5,288,865 A1 oder EP 0 604 922 A1 beschrieben werden.Examples of suitable crosslinking agents are aminoplast resins, as described, for example, in Römpp Lexicon Lacke und Druckfarben, Georg Thieme Verlag, 1998, page 29, "Aminoharze", the textbook "Lackadditive" by Johan Bieleman, Wiley-VCH, Weinheim, New York, 1998, pages 242 ff., The book "Paints, Coatings and Solvents", second completely revised edition, edit. D. Stoye and W. Freitag, Wiley-VCH, Weinheim, New York, 1998, pages 80 ff., The patents US 4,710,542 A1 or EP-B-0 245 700 A1 as well as in the article by B. Singh and co-workers "Carbamylmethylated Melamines, Novel Crosslinkers for the Coatings Industry ", in Advanced Organic Coatings Science and Technology Series, 1991, Volume 13, pages 193 to 207. Compounds or resins containing carboxyl groups, as described, for example, in US Pat Patent specification DE 196 52 813 A1 are described, containing epoxy groups Compounds or resins as described, for example, in the patents EP 0 299 420 A1, DE 22 14 650 B1, DE 27 49 576 B1, US 4,091,048 A1 or US 3,781,379 A1 Blocked polyisocyanates, such as those described in the Patents US 4,444,954 A1, DE 196 17 086 A1, DE 196 31 269 A1, EP 0 004 571 A1 or EP 0 582 051 A1, and / or tris (alkoxycarbonylamino) - triazines as described in the patents US 4,939,213 A1, US 5,084,541 A1, US 5,288,865 A1 or EP 0 604 922 A1.
Desweiteren können die erfindungsgemäßen Beschichtungsmittel mindestens einen Zusatzstoff enthalten.Furthermore, the coating compositions of the invention can have at least one Additive included.
Beispiele geeigneter Zusatzstoffe sind organische und anorganische farb- und/oder effektgebende Pigmente, organische und anorganische Füllstoffe, thermisch härtbare Reaktiverdünner oder mit aktinischer Strahlung härtbare Reaktivverdünner (vgl. Römpp Lexikon Lacke und Druckfarben, Stuttgart, New York, 1998, Seiten 491), niedrig siedende organische Lösemittel und/oder hochsiedende organische Lösemittel ("lange Lösemittel"), mit aktinischer Strahlung härtbare Bindemittel, UV-Absorber, Lichtschutzmittel, Radikalfänger, thermolabile radikalische Initiatoren, Photoinitiatoren, Katalysatoren für die Vernetzung, Entlüftungsmittel, Silpadditive, Polymerisationsinhibitoren, Entschäumer, Emulgatoren, Netzmittel, Haftvermittler, Verlaufmittel, filmbildende Hilfsmittel, rheologiesteuernde Additive oder Flammschutzmittel. Weitere Beispiele geeigneter Lackadditive werden in dem Lehrbuch "Lackadditive" von Johan Bieleman, Wiley-VCH, Weinheim, New York, 1998, beschrieben.Examples of suitable additives are organic and inorganic color and / or effect pigments, organic and inorganic fillers, thermally curable Reactive diluents or reactive diluents curable with actinic radiation (cf.Römpp Lexicon Lacke und Druckfarben, Stuttgart, New York, 1998, pages 491), low boiling organic solvents and / or high boiling organic solvents ("long Solvents "), binders curable with actinic radiation, UV absorbers, Light stabilizers, radical scavengers, thermolabile free radical initiators, photoinitiators, Crosslinking catalysts, deaerating agents, silane additives, Polymerization inhibitors, defoamers, emulsifiers, wetting agents, adhesion promoters, Leveling agents, film-forming aids, rheology-controlling additives or Flame retardant. Further examples of suitable paint additives are given in the textbook "Lackadditive" by Johan Bieleman, Wiley-VCH, Weinheim, New York, 1998, described.
Die erfindungsgemäßen Beschichtungsstoffe können Einkomponentensysteme sein.The coating materials of the invention can be one-component systems.
Im Rahmen der vorliegenden Erfindung ist unter einem Einkomponenten(1K)-System ein thermisch oder thermisch und mit aktinischer Strahlung härtender Beschichtungsstoff zu verstehen, bei dem das Bindemittel und das Vernetzungsmittel nebeneinander, d. h. in einer Komponente, vorliegen. Voraussetzung hierfür ist, daß die beiden Bestandteile erst bei höheren Temperaturen und/oder bei Bestrahlen mit aktinischer Strahlung miteinander vernetzen.In the context of the present invention is a one-component (1K) system coating material that cures thermally or thermally and with actinic radiation understand, in which the binder and the crosslinking agent side by side, d. H. in a Component. The prerequisite for this is that the two components only at higher temperatures and / or when irradiated with actinic radiation network.
Der Beschichtungsstoff kann des weiteren, wie vorstehend bereits ausgeführt, auch ein Zweikomponenten(2K)- oder Mehrkomponentenystem sein.As already explained above, the coating material can also be a Be a two-component (2K) or multi-component system.
Des weiteren können die erfindungsgemäßen Beschichtungsstoffe im wesentlichen frei von Wasser und/oder organischen Lösemitteln und pulverförmig oder flüssig sein (100%- Systeme). Im Rahmen der vorliegenden Erfindung bedeutet "im wesentlichen frei", daß der Gehalt an Wasser und/oder organischen Lösemitteln unter 5,0, vorzugsweise unter 3,0, bevorzugt unter 2,0, besonders bevorzugt unter 1,0, ganz besonders bevorzugt unter 0,5 Gew.-% und insbesondere unterhalb der gaschromatographischen Nachweisgrenze liegt. In dieser Form können sie beispielsweise als Pulverfüller, Pulverbasislacke, Pulverklarlacke oder flüssige Klarlacke verwendet werden.Furthermore, the coating materials of the invention can be essentially free of Water and / or organic solvents and powder or liquid (100% - Systems). In the context of the present invention, "essentially free" means that the content of water and / or organic solvents below 5.0, preferably below 3.0, preferably below 2.0, particularly preferably below 1.0, very particularly preferably below 0.5% by weight and in particular lies below the gas chromatographic detection limit. In You can use this form, for example, as a powder filler, powder basecoat, powder clearcoat or liquid clear coats can be used.
Es kann sich indes auch um einen auf Wasser basierenden Beschichtungsstoff, insbesondere einen Elektrotauchlack, einen Wasserfüller, einen Wasserbasislack, einen Wasserklarlack oder eine wäßrige Pulverlackdispersion (Pulverslurry-Klarlack oder Pulverslurry-Basislack), handeln.However, it can also be a water-based coating material, in particular an electrocoat, a water filler, a waterborne basecoat, a Water clearcoat or an aqueous powder coating dispersion (powder slurry clearcoat or Powder slurry basecoat).
Nicht zuletzt kann es sich auch um einen konventionellen, d. h. um einen auf organischen Lösemitteln basierenden Beschichtungsstoff handeln, beispielsweise einen konventionellen Füller, Basislack oder Klarlack. Last but not least, it can also be a conventional, i.e. H. around one on organic Solvent-based coating material, for example a conventional one Filler, basecoat or clearcoat.
Die Herstellung der erfindungsgemäßen Beschichtungsstoffe weist keine Besonderheiten auf, sondern erfolgt in üblicher und bekannter Weise durch Vermischen der vorstehend beschriebenen Bestandteile in geeigneten Mischaggregaten wie Rührkessel, Dissolver, Rührwerksmühlen, statischen Mischern, Zahnkranz-Dispergatoren oder Extruder nach den für die Herstellung der jeweiligen Beschichtungsstoffe geeigneten Verfahren.The production of the coating materials according to the invention has no special features on, but is done in a conventional and known manner by mixing the above described components in suitable mixing units such as stirred kettles, dissolvers, Agitator mills, static mixers, gear rim dispersers or extruders according to the processes suitable for the production of the respective coating materials.
Die Applikation der erfindungsgemäßen Beschichtungsstoffe kann durch alle üblichen Applikationsmethoden, wie z. B. Elektrotauchlackierung, Spritzen, Rakeln, Streichen, Gießen, Tauchen, Tränken, Träufeln oder Walzen erfolgen. Dabei kann das zu beschichtende Substrat als solches ruhen, wobei die Applikationseinrichtung oder -anlage bewegt wird. Indes kann auch das zu beschichtende Substrat, insbesondere ein Coil, bewegt werden, wobei die Applikationsanlage relativ zum Substrat ruht oder in geeigneter Weise bewegt wird.The application of the coating materials according to the invention can be carried out by all customary methods Application methods, such as. B. electrocoating, spraying, knife coating, painting, Pouring, dipping, watering, trickling or rolling. This can be too resting substrate as such, the application device or system is moved. However, the substrate to be coated, in particular a coil, are moved, the application system being at rest relative to the substrate or in a more suitable manner Way is moved.
Die thermische Härtung der applizierten erfindungsgemäßen Beschichtungsstoffe weist ebenfalls keine methodischen Besonderheiten auf, sondern erfolgt in üblicher und bekannter Weise durch Erhitzen mit Infrarot- oder naher Infrarotstrahlung oder mit Heißluftgebläsen, gegebenenfalls unterstützt durch die Bestrahlung mit aktinischer Strahlung, wenn die erfindungsgemäßen Beschichtungsstoffe entsprechende Bestandteile enthalten.The thermal curing of the applied coating materials according to the invention has likewise no methodological particularities, but takes place in the usual and known manner by heating with infrared or near infrared radiation or with Hot air blowers, if necessary supported by irradiation with actinic Radiation if the coating materials according to the invention have corresponding constituents contain.
Hier tritt der besondere Vorteil der erfindungsgemäßen Beschichtungsstoffe besonders offen zu Tage, nämlich daß die thermische Vernetzung bereits bei Temperaturen unterhalb 160, vorzugsweise 150 und insbesondere 140°C vollständig abläuft, was die Beschichtung von vergleichsweise hitzempfindlichen Substraten gestattet.This is where the particular advantage of the coating materials according to the invention occurs open to the day, namely that the thermal crosslinking already at temperatures below 160, preferably 150 and in particular 140 ° C completely, what the coating of comparatively heat sensitive substrates.
Die erfindungsgemäßen Basislacke und/oder Klarlacke und sind hervorragend für die Herstellung farb- und/oder effektgebender Mehrschichtlackierungen nach dem Naß-in- naß-Verfahren geeignet, bei dem eine Basislackschicht appliziert, getrocknet und mit einer Klarlackschicht überschichtet wird, wonach Basislackschicht um Klarlackschicht gemeinsam gehärtet werden. Bekanntermaßen wird dieses Verfahren bei der Kraftfahrzeugersflackierung und -reparaturlackierung mit Vorteil angewandt. The basecoats and / or clearcoats of the invention are excellent for Production of color and / or effect multi-layer coatings after wet-in suitable wet method, in which a basecoat is applied, dried and coated with a Clear coat is overlaid, after which basecoat layer after clear coat be hardened together. As is known, this method is used by Automotive paintwork and refinish applied with advantage.
Darüber hinaus kommen aber die erfindungsgemäßen Beschichtungsstoffe wegen ihrer besonders vorteilhaften Eigenschaften auch für die Beschichtung von Bauwerken im Innen- und Außenbereich, für die Lackierung von Möbeln, Fenstern oder Türen und die industrielle Lackierung, inklusive Coil Coating, Container Coating und die Imprägnierung oder Beschichtung elektrotechnischer Bauteile, in Betracht. Im Rahmen der industriellen Lackierungen eignen sie sich für die Lackierung praktisch aller Teile für den privaten oder industriellen Gebrauch wie Radiatoren, Haushaltsgeräte, Kleinteile aus Metall wie Schrauben und Muttern, Radkappen, Felgen, Emballagen oder elektrotechnische Bauteile wie Motorwicklungen oder Transformatorwicklungen.In addition, however, the coating materials of the invention come because of their particularly advantageous properties also for the coating of buildings in the Indoor and outdoor use, for painting furniture, windows or doors and the industrial painting, including coil coating, container coating and impregnation or coating of electrical components. As part of the industrial Paintings are suitable for painting practically all parts for private or industrial use such as radiators, household appliances, small metal parts such as Screws and nuts, hubcaps, rims, packaging or electrical components such as motor windings or transformer windings.
Die erfindungsgemäßen Klebstoffe und Dichtungsmassen eignen sich hervorragend für die Herstellung von Klebschichten und Dichtungen, die auch unter klimatisch extremen und/oder rasch wechselnden klimatischen Bedingungen auf Dauer von besonders hoher Klebkraft und Dichtungsvermögen sind.The adhesives and sealants according to the invention are ideal for Manufacture of adhesive layers and seals, even under climatically extreme and / or rapidly changing climatic conditions in the long term of particularly high Adhesion and sealing ability are.
Demzufolge weisen die auf den vorstehend aufgeführten technologischen Gebieten üblicherweise angewandten grundierten oder ungrundierten Substrate, die mit mindestens einer erfindungsgemäßen Beschichtung beschichtet, mit mindestens einer erfindungsgemäßen Klebschicht verklebt und/oder mit mindestens einer erfindungsgemäßen Dichtung abgedichtet sind, bei einem besonders vorteilhaften anwendungstechnischen Eigenschaftsprofil eine besonders lange Gebrauchsdauer auf, was sie wirtschaftlich besonders attraktiv macht.Accordingly, they point to the technological areas listed above Usually used primed or unprimed substrates with at least a coating according to the invention coated with at least one adhesive layer according to the invention glued and / or with at least one Seal according to the invention are sealed in a particularly advantageous application-technical property profile a particularly long service life on what makes them particularly attractive economically.
Claims (10)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2000117651 DE10017651A1 (en) | 2000-04-08 | 2000-04-08 | Di- and polyisocyanates blocked with pyrazoles disubstituted in the 3,4-position and their use |
| AU2001254720A AU2001254720A1 (en) | 2000-04-08 | 2001-03-21 | Di- and polyisocyanates blocked by 3,4-disubstituted pyrazoles, and the use thereof |
| PCT/EP2001/003240 WO2001077201A1 (en) | 2000-04-08 | 2001-03-21 | Di- and polyisocyanates blocked by 3,4-disubstituted pyrazoles, and the use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2000117651 DE10017651A1 (en) | 2000-04-08 | 2000-04-08 | Di- and polyisocyanates blocked with pyrazoles disubstituted in the 3,4-position and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10017651A1 true DE10017651A1 (en) | 2001-10-18 |
Family
ID=7638141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2000117651 Withdrawn DE10017651A1 (en) | 2000-04-08 | 2000-04-08 | Di- and polyisocyanates blocked with pyrazoles disubstituted in the 3,4-position and their use |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU2001254720A1 (en) |
| DE (1) | DE10017651A1 (en) |
| WO (1) | WO2001077201A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7354458B2 (en) | 2002-03-15 | 2008-04-08 | Rudolf Gmbh & Co., Kg, Chemische Fabrik | Preparations based on water and/or organic solvents and their use as a finish on flat materials |
| DE102007020790A1 (en) | 2007-05-03 | 2008-11-06 | Rudolf Gmbh & Co. Kg Chemische Fabrik | Fluorocarbon polymer-free preparations based on water and / or organic solvents and their use as a finish on fabrics |
| US8231802B2 (en) | 2003-06-03 | 2012-07-31 | Rudolf Gmbh | Preparations for making planar structures oil-repellent and water-repellent, and use thereof |
| WO2016173805A1 (en) | 2015-04-30 | 2016-11-03 | Bernhard Sandner | Hydrophobizing compound and fluorocarbon polymer-free preparations based on water and/or organic solvents, the use thereof as a finish on sheet materials, and substrates obtained thereby |
| DE102016212443A1 (en) | 2016-07-07 | 2018-01-11 | Rudolf Gmbh | Preparations as water repellents |
| EP4050058A1 (en) | 2021-02-26 | 2022-08-31 | Rudolf GmbH | Hydrophobing agent with permanent effect |
| WO2025172516A1 (en) | 2024-02-16 | 2025-08-21 | Rudolf Gmbh | Compositions for treating surfaces |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160197375A1 (en) * | 2013-08-05 | 2016-07-07 | Empire Technology Development Llc | Gel electrolyte composition for rechargeable batteries |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0500495A2 (en) * | 1991-02-21 | 1992-08-26 | Ciba-Geigy Ag | Thermosetting composition |
| EP0159117B1 (en) * | 1984-02-29 | 1993-01-27 | The Baxenden Chemical Company Limited | Blocked isocyanates |
| WO1995006674A1 (en) * | 1993-09-03 | 1995-03-09 | Olin Corporation | Isocyanate-crosslinked coatings having reduced yellowing |
| DE19822631A1 (en) * | 1998-05-20 | 1999-11-25 | Basf Coatings Ag | Coating agents containing blocked polyurethane prepolymers and their use |
| DE19831656A1 (en) * | 1998-07-15 | 2000-01-20 | Basf Ag | Process for the preparation of pyrazoles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2717178B1 (en) * | 1994-03-14 | 1997-01-31 | Hoechst France | Acrylate-styrene resins crosslinked by a blocked polyisocyanate, preparation and applications as paint and / or varnish. |
-
2000
- 2000-04-08 DE DE2000117651 patent/DE10017651A1/en not_active Withdrawn
-
2001
- 2001-03-21 WO PCT/EP2001/003240 patent/WO2001077201A1/en not_active Ceased
- 2001-03-21 AU AU2001254720A patent/AU2001254720A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0159117B1 (en) * | 1984-02-29 | 1993-01-27 | The Baxenden Chemical Company Limited | Blocked isocyanates |
| EP0500495A2 (en) * | 1991-02-21 | 1992-08-26 | Ciba-Geigy Ag | Thermosetting composition |
| WO1995006674A1 (en) * | 1993-09-03 | 1995-03-09 | Olin Corporation | Isocyanate-crosslinked coatings having reduced yellowing |
| DE19822631A1 (en) * | 1998-05-20 | 1999-11-25 | Basf Coatings Ag | Coating agents containing blocked polyurethane prepolymers and their use |
| DE19831656A1 (en) * | 1998-07-15 | 2000-01-20 | Basf Ag | Process for the preparation of pyrazoles |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7354458B2 (en) | 2002-03-15 | 2008-04-08 | Rudolf Gmbh & Co., Kg, Chemische Fabrik | Preparations based on water and/or organic solvents and their use as a finish on flat materials |
| US8231802B2 (en) | 2003-06-03 | 2012-07-31 | Rudolf Gmbh | Preparations for making planar structures oil-repellent and water-repellent, and use thereof |
| DE102007020790A1 (en) | 2007-05-03 | 2008-11-06 | Rudolf Gmbh & Co. Kg Chemische Fabrik | Fluorocarbon polymer-free preparations based on water and / or organic solvents and their use as a finish on fabrics |
| US8703894B2 (en) | 2007-05-03 | 2014-04-22 | Rudolf Gmbh & Co. Kg Chemische Fabrik | Fluorocarbon polymer-free preparations based on water and/or organic solvents and the use thereof as a finish on flat materials |
| WO2016173805A1 (en) | 2015-04-30 | 2016-11-03 | Bernhard Sandner | Hydrophobizing compound and fluorocarbon polymer-free preparations based on water and/or organic solvents, the use thereof as a finish on sheet materials, and substrates obtained thereby |
| DE102016212443A1 (en) | 2016-07-07 | 2018-01-11 | Rudolf Gmbh | Preparations as water repellents |
| WO2018007549A1 (en) | 2016-07-07 | 2018-01-11 | Rudolf Gmbh | Preparation as water repelling agents |
| US10822500B2 (en) | 2016-07-07 | 2020-11-03 | Rudolf Gmbh | Preparations as hydrophobing agents |
| EP4050058A1 (en) | 2021-02-26 | 2022-08-31 | Rudolf GmbH | Hydrophobing agent with permanent effect |
| WO2022180142A1 (en) | 2021-02-26 | 2022-09-01 | Rudolf Gmbh | Hydrophobizing agent having a permanent effect |
| WO2025172516A1 (en) | 2024-02-16 | 2025-08-21 | Rudolf Gmbh | Compositions for treating surfaces |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001254720A1 (en) | 2001-10-23 |
| WO2001077201A1 (en) | 2001-10-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8130 | Withdrawal |