CA1300774C - Copolymeres greffes de polyester, compositions de revetement souples comportant ceux-ci et macromeres de polyester ramifies utilises pour leur preparation - Google Patents

Copolymeres greffes de polyester, compositions de revetement souples comportant ceux-ci et macromeres de polyester ramifies utilises pour leur preparation

Info

Publication number: CA1300774C
Authority: CA; Canada
Prior art keywords: hydroxy; hydroxy functional; graft copolymer; functional polyester; polyester graft
Prior art date: 1988-11-01
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.): Expired - Lifetime

Application number

CA000581894A

Other languages

English (en)

Inventor

Rose Ann Ryntz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1988-11-01

Filing date

1988-11-01

Publication date

1992-05-12

1988-11-01 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1988-11-01 Priority to CA000581894A priority Critical patent/CA1300774C/fr

1992-05-12 Application granted granted Critical

1992-05-12 Publication of CA1300774C publication Critical patent/CA1300774C/fr

2009-05-12 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920000728 polyester Polymers 0.000 title claims abstract description 74
229920000578 graft copolymer Polymers 0.000 title claims abstract description 35
239000008199 coating composition Substances 0.000 title claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 91
-1 silane compound Chemical class 0.000 claims abstract description 47
239000000178 monomer Substances 0.000 claims abstract description 31
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 20
125000000962 organic group Chemical group 0.000 claims abstract description 16
229910000077 silane Inorganic materials 0.000 claims abstract description 15
229920001577 copolymer Polymers 0.000 claims abstract description 13
239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 11
239000007795 chemical reaction product Substances 0.000 claims abstract description 11
229910052751 metal Inorganic materials 0.000 claims abstract description 10
239000002184 metal Substances 0.000 claims abstract description 10
239000000126 substance Substances 0.000 claims abstract description 10
229920003023 plastic Polymers 0.000 claims abstract description 9
239000004033 plastic Substances 0.000 claims abstract description 9
239000000758 substrate Substances 0.000 claims abstract description 7
229920001187 thermosetting polymer Polymers 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 62
229920005862 polyol Polymers 0.000 claims description 29
150000003077 polyols Chemical class 0.000 claims description 29
150000002009 diols Chemical class 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 20
125000005442 diisocyanate group Chemical group 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 15
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 12
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 11
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 7
150000008064 anhydrides Chemical class 0.000 claims description 6
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 claims description 3
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
125000002015 acyclic group Chemical group 0.000 claims description 3
150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
229920001610 polycaprolactone Polymers 0.000 claims description 3
239000004632 polycaprolactone Substances 0.000 claims description 3
239000000047 product Substances 0.000 claims description 3
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
238000010526 radical polymerization reaction Methods 0.000 claims description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 4
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 4
229920006395 saturated elastomer Polymers 0.000 claims 3
LUYHWJKHJNFYGV-UHFFFAOYSA-N 1,2-diisocyanato-3-phenylbenzene Chemical compound O=C=NC1=CC=CC(C=2C=CC=CC=2)=C1N=C=O LUYHWJKHJNFYGV-UHFFFAOYSA-N 0.000 claims 2
WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 claims 2
239000005058 Isophorone diisocyanate Substances 0.000 claims 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
235000011037 adipic acid Nutrition 0.000 claims 2
239000001361 adipic acid Substances 0.000 claims 2
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 2
150000002118 epoxides Chemical class 0.000 claims 2
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims 2
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims 2
UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims 1
MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 claims 1
BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical group OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 claims 1
IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 claims 1
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims 1
XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 1
229910018557 Si O Inorganic materials 0.000 claims 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims 1
125000005250 alkyl acrylate group Chemical group 0.000 claims 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
125000005647 linker group Chemical group 0.000 claims 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims 1
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims 1
238000000576 coating method Methods 0.000 abstract description 32
239000011248 coating agent Substances 0.000 abstract description 28
239000003431 cross linking reagent Substances 0.000 abstract description 12
239000000376 reactant Substances 0.000 abstract description 10
150000002500 ions Chemical class 0.000 description 52
229920005989 resin Polymers 0.000 description 38
239000011347 resin Substances 0.000 description 38
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 24
239000003795 chemical substances by application Substances 0.000 description 22
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
229920003270 Cymel® Polymers 0.000 description 11
229920000877 Melamine resin Polymers 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
229920001228 polyisocyanate Polymers 0.000 description 11
239000005056 polyisocyanate Substances 0.000 description 11
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
239000000463 material Substances 0.000 description 10
239000008096 xylene Substances 0.000 description 10
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 9
239000006096 absorbing agent Substances 0.000 description 9
238000000034 method Methods 0.000 description 9
229920002554 vinyl polymer Polymers 0.000 description 9
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 8
238000004132 cross linking Methods 0.000 description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
239000007787 solid Substances 0.000 description 7
150000004072 triols Chemical class 0.000 description 7
239000004971 Cross linker Substances 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000007974 melamines Chemical class 0.000 description 6
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
239000000654 additive Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
239000003607 modifier Substances 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229940056960 melamin Drugs 0.000 description 4
239000000049 pigment Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 3
239000000243 solution Substances 0.000 description 3
DSCFFEYYQKSRSV-UHFFFAOYSA-N 1L-O1-methyl-muco-inositol Natural products COC1C(O)C(O)C(O)C(O)C1O DSCFFEYYQKSRSV-UHFFFAOYSA-N 0.000 description 2
LHOKCCUPZYSAJG-UHFFFAOYSA-N 6-oxohexyl acetate Chemical compound CC(=O)OCCCCCC=O LHOKCCUPZYSAJG-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000791420 Plica Species 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
239000012964 benzotriazole Substances 0.000 description 2
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
229940043232 butyl acetate Drugs 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000004927 clay Substances 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
239000000539 dimer Substances 0.000 description 2
NICWAKGKDIAMOD-UHFFFAOYSA-N ethyl 3,3-bis(2-methylbutan-2-ylperoxy)butanoate Chemical compound CCOC(=O)CC(C)(OOC(C)(C)CC)OOC(C)(C)CC NICWAKGKDIAMOD-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
125000005395 methacrylic acid group Chemical class 0.000 description 2
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000005507 spraying Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BHPAHQHRTQUACM-UHFFFAOYSA-N (4-hydroxy-4-methylpentan-2-yl) 2-methylprop-2-enoate Chemical compound CC(O)(C)CC(C)OC(=O)C(C)=C BHPAHQHRTQUACM-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
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
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241001441571 Hiodontidae Species 0.000 description 1
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150000002334 glycols Chemical class 0.000 description 1
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WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
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150000002513 isocyanates Chemical class 0.000 description 1
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230000007775 late Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011572 manganese Substances 0.000 description 1
SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
210000004940 nucleus Anatomy 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000003973 paint Substances 0.000 description 1
229940059574 pentaerithrityl Drugs 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
229920005906 polyester polyol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
235000020079 raki Nutrition 0.000 description 1
230000035939 shock Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
239000010936 titanium Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
230000002087 whitening effect Effects 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)
Paints Or Removers (AREA)

CA000581894A 1988-11-01 1988-11-01 Copolymeres greffes de polyester, compositions de revetement souples comportant ceux-ci et macromeres de polyester ramifies utilises pour leur preparation Expired - Lifetime CA1300774C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000581894A CA1300774C (fr)	1988-11-01	1988-11-01	Copolymeres greffes de polyester, compositions de revetement souples comportant ceux-ci et macromeres de polyester ramifies utilises pour leur preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000581894A CA1300774C (fr)	1988-11-01	1988-11-01	Copolymeres greffes de polyester, compositions de revetement souples comportant ceux-ci et macromeres de polyester ramifies utilises pour leur preparation

Publications (1)

Publication Number	Publication Date
CA1300774C true CA1300774C (fr)	1992-05-12

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CA000581894A Expired - Lifetime CA1300774C (fr)	1988-11-01	1988-11-01	Copolymeres greffes de polyester, compositions de revetement souples comportant ceux-ci et macromeres de polyester ramifies utilises pour leur preparation

Country Status (1)

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CA (1)	CA1300774C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117511387A (zh) *	2023-11-22	2024-02-06	江苏众立生包装科技有限公司	含有聚（氨酯-丙烯酸酯）的印刷光油的制备方法

1988
- 1988-11-01 CA CA000581894A patent/CA1300774C/fr not_active Expired - Lifetime

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117511387A (zh) *	2023-11-22	2024-02-06	江苏众立生包装科技有限公司	含有聚（氨酯-丙烯酸酯）的印刷光油的制备方法
CN117511387B (zh) *	2023-11-22	2024-04-30	江苏众立生包装科技有限公司	含有聚（氨酯-丙烯酸酯）的印刷光油的制备方法

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US4243705A (en)	1981-01-06	Process for coating high solids coating compositions
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US4888399A (en)	1989-12-19	Polyester graft copolymers, flexible coating compositions comprising same and branched polyester macromers for preparing same II
US6015864A (en)	2000-01-18	Thermosetting powder coating composition
US4727099A (en)	1988-02-23	Coating composition containing a reactive urethane component, a hydroxyl containing acrylic polymer having pendent ester groups and a metallic alkylate catalyst

Legal Events

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1998-05-12	MKLA	Lapsed