NL1007186C2 - ß-hydroxyalkylamide groepen bevattend condensatiepolymeer. - Google Patents
ß-hydroxyalkylamide groepen bevattend condensatiepolymeer. Download PDFInfo
- Publication number
- NL1007186C2 NL1007186C2 NL1007186A NL1007186A NL1007186C2 NL 1007186 C2 NL1007186 C2 NL 1007186C2 NL 1007186 A NL1007186 A NL 1007186A NL 1007186 A NL1007186 A NL 1007186A NL 1007186 C2 NL1007186 C2 NL 1007186C2
- Authority
- NL
- Netherlands
- Prior art keywords
- polymer
- aryl
- cyclo
- alkyl
- acid
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 116
- 238000009833 condensation Methods 0.000 title claims description 6
- 230000005494 condensation Effects 0.000 title claims description 6
- -1 cyclic anhydride Chemical class 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 239000003973 paint Substances 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 9
- 239000000843 powder Substances 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 35
- 238000000576 coating method Methods 0.000 claims description 30
- 239000004971 Cross linker Substances 0.000 claims description 23
- 239000011248 coating agent Substances 0.000 claims description 16
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 15
- 239000011230 binding agent Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000001735 carboxylic acids Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 229940102253 isopropanolamine Drugs 0.000 claims description 4
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 9
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract description 4
- 125000003368 amide group Chemical group 0.000 abstract description 2
- 125000004185 ester group Chemical group 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 14
- 150000008064 anhydrides Chemical class 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 9
- 229940043276 diisopropanolamine Drugs 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 229920000058 polyacrylate Polymers 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920000180 alkyd Polymers 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 4
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013256 coordination polymer Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000005516 engineering process Methods 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000007872 degassing Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- RDMHXWZYVFGYSF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese Chemical compound [Mn].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RDMHXWZYVFGYSF-LNTINUHCSA-N 0.000 description 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- PFJZOBRGDTYDQC-UHFFFAOYSA-N 1,4-diisocyanato-4-methylpentane Chemical compound O=C=NC(C)(C)CCCN=C=O PFJZOBRGDTYDQC-UHFFFAOYSA-N 0.000 description 1
- XXPLPVREXQZANT-UHFFFAOYSA-N 1,5-diisocyanato-2,2,5-trimethylhexane Chemical compound O=C=NCC(C)(C)CCC(C)(C)N=C=O XXPLPVREXQZANT-UHFFFAOYSA-N 0.000 description 1
- AQXHKHLEOAFNAT-UHFFFAOYSA-N 1,6-diisocyanato-6-methylheptane Chemical compound O=C=NC(C)(C)CCCCCN=C=O AQXHKHLEOAFNAT-UHFFFAOYSA-N 0.000 description 1
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 1
- NODVXIDWDAUDNH-UHFFFAOYSA-N 1,7-diisocyanato-3,7-dimethyloctane Chemical compound O=C=NCCC(C)CCCC(C)(C)N=C=O NODVXIDWDAUDNH-UHFFFAOYSA-N 0.000 description 1
- ZRRREUMHJJXGRJ-UHFFFAOYSA-N 1-ethyl-3-isocyanato-1-(isocyanatomethyl)-2,3-dimethylcyclopentane Chemical compound O=C=NCC1(CC)CCC(C)(N=C=O)C1C ZRRREUMHJJXGRJ-UHFFFAOYSA-N 0.000 description 1
- HZJYQUSBJDFKCF-UHFFFAOYSA-N 1-isocyanato-3-(2-isocyanatoethyl)-1,2,2-trimethylcyclopentane Chemical compound CC1(C)C(CCN=C=O)CCC1(C)N=C=O HZJYQUSBJDFKCF-UHFFFAOYSA-N 0.000 description 1
- KLGXHWHLMXVVSL-UHFFFAOYSA-N 1-isocyanato-3-(isocyanatomethyl)-1,3-dimethylcyclohexane Chemical compound O=C=NCC1(C)CCCC(C)(N=C=O)C1 KLGXHWHLMXVVSL-UHFFFAOYSA-N 0.000 description 1
- YWOJSGMFQMEFSA-UHFFFAOYSA-N 1-isocyanato-4-(isocyanatomethyl)-1,4-dimethylcyclohexane Chemical compound O=C=NCC1(C)CCC(C)(N=C=O)CC1 YWOJSGMFQMEFSA-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- AJKXDPSHWRTFOZ-UHFFFAOYSA-N 2-ethylhexane-1,6-diol Chemical compound CCC(CO)CCCCO AJKXDPSHWRTFOZ-UHFFFAOYSA-N 0.000 description 1
- OFYFURKXMHQOGG-UHFFFAOYSA-J 2-ethylhexanoate;zirconium(4+) Chemical compound [Zr+4].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O OFYFURKXMHQOGG-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
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- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24058—Structurally defined web or sheet [e.g., overall dimension, etc.] including grain, strips, or filamentary elements in respective layers or components in angular relation
- Y10T428/24074—Strand or strand-portions
- Y10T428/24091—Strand or strand-portions with additional layer[s]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
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)
- Polyamides (AREA)
- Polyesters Or Polycarbonates (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1007186A NL1007186C2 (nl) | 1997-10-01 | 1997-10-01 | ß-hydroxyalkylamide groepen bevattend condensatiepolymeer. |
| JP2000513892A JP3643032B2 (ja) | 1997-10-01 | 1998-09-22 | ヒドロキシアルキルアミド基を含む縮合ポリマー |
| EP98944344A EP1036106B1 (fr) | 1997-10-01 | 1998-09-22 | Polymere de condensation contenant des groupes hydroxylalkylamides |
| AT98944344T ATE247143T1 (de) | 1997-10-01 | 1998-09-22 | Hydroxyalkylamidgruppen enthaltendes kondensationspolymer |
| DE69817216T DE69817216T2 (de) | 1997-10-01 | 1998-09-22 | Hydroxyalkylamidgruppen enthaltendes kondensationspolymer |
| CA002305364A CA2305364C (fr) | 1997-10-01 | 1998-09-22 | Polymere de condensation contenant des groupes hydroxylalkylamides |
| ES98944344T ES2205543T3 (es) | 1997-10-01 | 1998-09-22 | Polimero de condensacion que contiene grupos hidroxialquilamida. |
| KR20007003495A KR100524455B1 (ko) | 1997-10-01 | 1998-09-22 | 히드록시알킬아미드기를 함유하는 축합중합체 |
| IL13539698A IL135396A (en) | 1997-10-01 | 1998-09-22 | Condensation polymer containing hydroxyalkylamide groups |
| AU91902/98A AU746623B2 (en) | 1997-10-01 | 1998-09-22 | Condensation polymer containing hydroxyalkylamide groups |
| PCT/NL1998/000546 WO1999016810A1 (fr) | 1997-10-01 | 1998-09-22 | Polymere de condensation contenant des groupes hydroxylalkylamides |
| CNB988116545A CN1158334C (zh) | 1997-10-01 | 1998-09-22 | 含羟烷基酰胺基的缩聚物 |
| TW087116006A TW588069B (en) | 1997-10-01 | 1998-09-25 | Condensation polymer containing hydroxylalkylamide groups |
| MYPI98004472A MY125719A (en) | 1997-10-01 | 1998-09-29 | Condensation polymer containing hydroxyalkylamide groups |
| US09/534,326 US6392006B1 (en) | 1997-10-01 | 2000-03-24 | Condensation polymer containing hydroxyalkylamide groups |
| US09/941,793 US6387496B1 (en) | 1997-10-01 | 2001-08-30 | Condensation polymer containing hydroxyalkylamide groups |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1007186A NL1007186C2 (nl) | 1997-10-01 | 1997-10-01 | ß-hydroxyalkylamide groepen bevattend condensatiepolymeer. |
| NL1007186 | 1997-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL1007186C2 true NL1007186C2 (nl) | 1999-04-07 |
Family
ID=19765776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1007186A NL1007186C2 (nl) | 1997-10-01 | 1997-10-01 | ß-hydroxyalkylamide groepen bevattend condensatiepolymeer. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US6392006B1 (fr) |
| EP (1) | EP1036106B1 (fr) |
| JP (1) | JP3643032B2 (fr) |
| KR (1) | KR100524455B1 (fr) |
| CN (1) | CN1158334C (fr) |
| AT (1) | ATE247143T1 (fr) |
| AU (1) | AU746623B2 (fr) |
| CA (1) | CA2305364C (fr) |
| DE (1) | DE69817216T2 (fr) |
| ES (1) | ES2205543T3 (fr) |
| IL (1) | IL135396A (fr) |
| MY (1) | MY125719A (fr) |
| NL (1) | NL1007186C2 (fr) |
| TW (1) | TW588069B (fr) |
| WO (1) | WO1999016810A1 (fr) |
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| EP1081176A1 (fr) * | 1999-08-31 | 2001-03-07 | Dsm N.V. | Procédé de préparation d'un polymère de condensation |
| DE10004136C2 (de) | 2000-01-31 | 2001-11-29 | Ems Chemie Ag | Wärmehärtbare Beschichtungsmassen |
| EP1127931A1 (fr) | 2000-02-24 | 2001-08-29 | Dsm N.V. | Procédé pour la préparation d'un liant de peinture thermodurcissable |
| ATE377642T1 (de) | 2000-04-07 | 2007-11-15 | Shell Int Research | Verfahren zur hemmung von verstopfung von röhren durch gashydraten |
| EP1149854A1 (fr) * | 2000-04-25 | 2001-10-31 | Dsm N.V. | Composition de toner |
| EP1170265A1 (fr) * | 2000-07-04 | 2002-01-09 | Rockwool International A/S | Liant pour produits en laine minérale |
| NL1016845C2 (nl) * | 2000-12-11 | 2002-06-28 | Topchim N V | Papierbekledingssamenstelling. |
| ATE397650T1 (de) | 2001-06-14 | 2008-06-15 | Shell Int Research | Verfahren zum solubilisieren von asphaltenen in einem kohlenwasserstoffgemisch |
| AU2002321808A1 (en) * | 2001-08-08 | 2003-02-24 | B.J.M. Laboratories Ltd. | Dental compositions |
| NL1020682C2 (nl) * | 2002-05-27 | 2003-11-28 | Oce Tech Bv | Smeltbare inktsamenstelling. |
| EP1388574A1 (fr) * | 2002-08-05 | 2004-02-11 | DSM IP Assets B.V. | Composition de peinture en poudre |
| WO2003099943A1 (fr) * | 2002-05-27 | 2003-12-04 | Dsm Ip Assets B.V. | Composition de peinture pulverulente |
| EA012871B1 (ru) * | 2002-05-31 | 2009-12-30 | Грейс Гмбх Унд Ко. Кг | Матирующее вещество для порошкового покрытия, включающее сложный эфирамидный продукт конденсации |
| EP1382643A1 (fr) * | 2002-06-07 | 2004-01-21 | DSM IP Assets B.V. | Film barrière en couche à base de polyesteramide et son utilisation |
| CA2497366A1 (fr) | 2002-09-03 | 2004-03-18 | Shell Canada Limited | Procede et compositions empechant la formation d'hydrates d'hydrocarbures |
| US7933655B2 (en) * | 2002-10-31 | 2011-04-26 | Medtronic, Inc. | Neurostimulation therapy manipulation |
| EP1424362A1 (fr) * | 2002-11-27 | 2004-06-02 | DSM IP Assets B.V. | Procédé de préparation d'une composition |
| US20050288450A1 (en) * | 2003-05-23 | 2005-12-29 | Tim Fletcher | Coating matting agent comprising amide condensation product |
| AU2005226922B2 (en) | 2004-03-25 | 2010-03-04 | Dsm Ip Assets B.V. | UV absorbing chromophores covalently bonded to hyperbranched polymers |
| DE102004039102A1 (de) * | 2004-08-11 | 2006-02-23 | Basf Ag | Verfahren zur Herstellung von hochverzweigten Polyesteramiden |
| CN101065466B (zh) | 2004-11-24 | 2013-02-13 | 国际壳牌研究有限公司 | 改进含有蜡和其它烃的混合物的流动性的方法 |
| CA2598184A1 (fr) | 2005-02-21 | 2006-08-24 | Basf Aktiengesellschaft | Composition d'agents actifs |
| US20070043142A1 (en) * | 2005-08-19 | 2007-02-22 | Hanna Dodiuk-Kenig | Dental compositions based on nanofiber reinforcement |
| DE102005045150A1 (de) * | 2005-09-22 | 2007-04-05 | Basf Coatings Ag | Verwendung von Phosphonsäurediestern und Diphosphonsäurediestern sowie thermisch härtbare Gemische, enthaltend Phosphonsäurediester und Diphosphonsäurediester |
| DE102005045228A1 (de) | 2005-09-22 | 2007-04-05 | Basf Coatings Ag | Verwendung von Phosphonsäurediestern und Diphosphonsäurediestern sowie silangruppenhaltige, härtbare Gemische, enthaltend Phosphonsäurediester und Diphosphonsäurediester |
| WO2007134614A1 (fr) * | 2006-05-18 | 2007-11-29 | Henkel Ag & Co. Kgaa | Lessive protégeant les couleurs |
| DE102006024823A1 (de) | 2006-05-29 | 2007-12-06 | Basf Coatings Ag | Verwendung von härtbaren Gemischen, enthaltend silangruppenhaltige Verbindungen sowie Phosphonsäurediester oder Diphosphonsäurediester, als Haftvermittler |
| WO2007144189A2 (fr) * | 2006-06-16 | 2007-12-21 | Dsm Ip Assets B.V. | Compositions à base de polycondensats hyper-ramifiés et nouveaux polycondensats hyper-ramifiés |
| EP2029693B1 (fr) * | 2006-06-20 | 2011-07-27 | M-I Llc | Matériaux polymériques hautement ramifiés en tant que tensioactifs pour boues à base d'huile |
| WO2008068180A1 (fr) * | 2006-12-07 | 2008-06-12 | Basf Se | Mélange liant contenant des polymères hyperramifiés ou des résines aminoplastes contenant des polymères hyperramifiés |
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| DE102007014720A1 (de) | 2007-03-23 | 2008-09-25 | Basf Coatings Japan Ltd., Yokohama | Phosphonat-haltiges Zweikomponenten-Lacksystem, dessen Herstellung und Verwendung |
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| WO2009074430A1 (fr) * | 2007-12-12 | 2009-06-18 | Unilever Nv | Composition de détergent pour lessive |
| US8293831B2 (en) * | 2008-10-30 | 2012-10-23 | E I Du Pont De Nemours And Company | Thermoplastic composition including thermally conductive filler and hyperbranched polyesteramide |
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| WO2010107503A1 (fr) | 2009-03-19 | 2010-09-23 | Millipore Corporation | Élimination de micro-organismes dans des échantillons de fluide en utilisant des milieux de filtration à nanofibres |
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| DE102009029060A1 (de) | 2009-09-01 | 2011-03-03 | Henkel Ag & Co. Kgaa | Mittel zur Behandlung harter Oberflächen |
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| EP2509575B1 (fr) | 2009-12-09 | 2014-08-27 | DSM IP Assets B.V. | Nouveaux composés |
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| WO2011070071A2 (fr) | 2009-12-09 | 2011-06-16 | Dsm Ip Assets B.V. | Nouveau composé |
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| US10174156B2 (en) | 2009-12-18 | 2019-01-08 | Basf Se | Hyperbranched polyester with a hydrophobic nucleus for solubilizing poorly soluble active substances |
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| EP2607434A1 (fr) | 2011-12-20 | 2013-06-26 | Akzo Nobel Coatings International B.V. | Séchoir pour composition de revêtement auto-oxydable |
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| CN104011185B (zh) | 2011-12-20 | 2017-11-21 | 国际壳牌研究有限公司 | 抑制气体水合物堵塞管道的方法 |
| BR112014013953B1 (pt) | 2011-12-20 | 2020-02-04 | Shell Int Research | método para inibir o entupimento de um conduto |
| EP2607435A1 (fr) | 2011-12-20 | 2013-06-26 | Akzo Nobel Coatings International B.V. | Sèche-linge pour composition de revêtement auto-oxydable |
| EP2873410B1 (fr) * | 2012-07-10 | 2022-05-04 | Tokuyama Dental Corporation | Composition d'adhésif dentaire |
| JP6203266B2 (ja) | 2012-09-20 | 2017-09-27 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 超分岐リン酸エステル |
| US9921205B2 (en) | 2012-11-13 | 2018-03-20 | Chevron U.S.A. Inc. | Method for determining the effectiveness of asphaltene dispersant additives for inhibiting or preventing asphaltene precipitation in a hydrocarbon-containing material subjected to elevated temperature and presssure conditions |
| JP6454905B2 (ja) | 2013-06-20 | 2019-01-23 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | ハイパーブランチポリマー |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3709858A (en) * | 1971-06-10 | 1973-01-09 | Eastman Kodak Co | Polyesteramide coating compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3652501A (en) | 1970-05-28 | 1972-03-28 | Eastman Kodak Co | Water soluble alkyd resins |
| BE1006097A3 (nl) * | 1992-07-29 | 1994-05-10 | Dsm Nv | Poederverf op basis van een polymeer met vrije carbonzuurgroepen als bindmiddel en een beta-hydroxyalkylamidegroepen bevattende verbinding als crosslinker. |
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1997
- 1997-10-01 NL NL1007186A patent/NL1007186C2/nl not_active IP Right Cessation
-
1998
- 1998-09-22 WO PCT/NL1998/000546 patent/WO1999016810A1/fr not_active Ceased
- 1998-09-22 AU AU91902/98A patent/AU746623B2/en not_active Ceased
- 1998-09-22 CN CNB988116545A patent/CN1158334C/zh not_active Expired - Fee Related
- 1998-09-22 JP JP2000513892A patent/JP3643032B2/ja not_active Expired - Fee Related
- 1998-09-22 IL IL13539698A patent/IL135396A/xx not_active IP Right Cessation
- 1998-09-22 CA CA002305364A patent/CA2305364C/fr not_active Expired - Fee Related
- 1998-09-22 EP EP98944344A patent/EP1036106B1/fr not_active Expired - Lifetime
- 1998-09-22 ES ES98944344T patent/ES2205543T3/es not_active Expired - Lifetime
- 1998-09-22 DE DE69817216T patent/DE69817216T2/de not_active Expired - Lifetime
- 1998-09-22 AT AT98944344T patent/ATE247143T1/de active
- 1998-09-22 KR KR20007003495A patent/KR100524455B1/ko not_active Expired - Fee Related
- 1998-09-25 TW TW087116006A patent/TW588069B/zh not_active IP Right Cessation
- 1998-09-29 MY MYPI98004472A patent/MY125719A/en unknown
-
2000
- 2000-03-24 US US09/534,326 patent/US6392006B1/en not_active Expired - Lifetime
-
2001
- 2001-08-30 US US09/941,793 patent/US6387496B1/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709858A (en) * | 1971-06-10 | 1973-01-09 | Eastman Kodak Co | Polyesteramide coating compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| MY125719A (en) | 2006-08-30 |
| US20020055609A1 (en) | 2002-05-09 |
| DE69817216T2 (de) | 2004-06-09 |
| CA2305364A1 (fr) | 1999-04-08 |
| TW588069B (en) | 2004-05-21 |
| US6392006B1 (en) | 2002-05-21 |
| ES2205543T3 (es) | 2004-05-01 |
| US6387496B1 (en) | 2002-05-14 |
| AU9190298A (en) | 1999-04-23 |
| JP2001518539A (ja) | 2001-10-16 |
| EP1036106A1 (fr) | 2000-09-20 |
| WO1999016810A1 (fr) | 1999-04-08 |
| EP1036106B1 (fr) | 2003-08-13 |
| KR100524455B1 (ko) | 2005-10-26 |
| JP3643032B2 (ja) | 2005-04-27 |
| IL135396A (en) | 2005-07-25 |
| IL135396A0 (en) | 2001-05-20 |
| CA2305364C (fr) | 2004-06-29 |
| DE69817216D1 (de) | 2003-09-18 |
| ATE247143T1 (de) | 2003-08-15 |
| CN1281478A (zh) | 2001-01-24 |
| KR20010030837A (ko) | 2001-04-16 |
| AU746623B2 (en) | 2002-05-02 |
| CN1158334C (zh) | 2004-07-21 |
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