CA1238742A - Enduits aqueux et methode de production - Google Patents

Enduits aqueux et methode de production

Info

Publication number: CA1238742A
Authority: CA; Canada
Prior art keywords: groups; polymer; epoxy; epoxy resin; addition polymer
Prior art date: 1982-12-30
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

Application number

CA000443024A

Other languages

English (en)

Inventor

Shaw C. Chu

Arthur T. Spencer

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.)

Valspar Corp

Original Assignee

Valspar Corp

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.)

1982-12-30

Filing date

1983-12-12

Publication date

1988-06-28

1982-12-30 Priority claimed from US06/454,818 external-priority patent/US4446258A/en

1982-12-30 Priority claimed from US06/454,771 external-priority patent/US4476262A/en

1983-12-12 Application filed by Valspar Corp filed Critical Valspar Corp

1988-06-28 Application granted granted Critical

1988-06-28 Publication of CA1238742A publication Critical patent/CA1238742A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 15
239000008199 coating composition Substances 0.000 title claims abstract description 12
229920000642 polymer Polymers 0.000 claims abstract description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 47
239000003822 epoxy resin Substances 0.000 claims abstract description 44
229920000647 polyepoxide Polymers 0.000 claims abstract description 44
239000000203 mixture Substances 0.000 claims abstract description 38
238000006243 chemical reaction Methods 0.000 claims abstract description 34
229920000831 ionic polymer Polymers 0.000 claims abstract description 25
239000006185 dispersion Substances 0.000 claims abstract description 24
238000011065 in-situ storage Methods 0.000 claims abstract description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 43
239000000178 monomer Substances 0.000 claims description 37
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 34
150000001412 amines Chemical class 0.000 claims description 20
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical group CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 15
229960002887 deanol Drugs 0.000 claims description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
150000003512 tertiary amines Chemical class 0.000 claims description 12
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 11
229920001577 copolymer Polymers 0.000 claims description 9
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
230000003472 neutralizing effect Effects 0.000 claims description 8
125000004185 ester group Chemical group 0.000 claims description 7
238000006116 polymerization reaction Methods 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 6
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 claims description 3
238000012644 addition polymerization Methods 0.000 claims description 2
229920003145 methacrylic acid copolymer Polymers 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 18
239000004593 Epoxy Substances 0.000 abstract description 17
229920005989 resin Polymers 0.000 abstract description 11
239000011347 resin Substances 0.000 abstract description 11
238000000576 coating method Methods 0.000 abstract description 8
239000004094 surface-active agent Substances 0.000 abstract description 5
RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 16
125000003700 epoxy group Chemical group 0.000 description 15
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
239000007787 solid Substances 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 10
238000005886 esterification reaction Methods 0.000 description 9
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 8
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 8
239000003054 catalyst Substances 0.000 description 8
239000008367 deionised water Substances 0.000 description 8
229910021641 deionized water Inorganic materials 0.000 description 8
230000032050 esterification Effects 0.000 description 8
KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 8
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 8
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
-1 hydroxy ester Chemical class 0.000 description 7
239000000243 solution Substances 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000002245 particle Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
239000004342 Benzoyl peroxide Substances 0.000 description 4
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
229930185605 Bisphenol Natural products 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
235000019400 benzoyl peroxide Nutrition 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
238000006386 neutralization reaction Methods 0.000 description 4
229920000058 polyacrylate Polymers 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
125000001453 quaternary ammonium group Chemical group 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000005028 tinplate Substances 0.000 description 4
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
229920003270 Cymel® Polymers 0.000 description 3
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229920006243 acrylic copolymer Polymers 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
229920000570 polyether Polymers 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
239000007921 spray Substances 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000009928 pasteurization Methods 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
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
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 0.000 description 1
UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
TUZBYYLVVXPEMA-UHFFFAOYSA-N butyl prop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CCCCOC(=O)C=C TUZBYYLVVXPEMA-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
239000012972 dimethylethanolamine Substances 0.000 description 1
239000004815 dispersion polymer Substances 0.000 description 1
238000004090 dissolution Methods 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
239000012467 final product Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007974 melamines Chemical class 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
XZXYVKWNNYKLGA-UHFFFAOYSA-N n-(2-methylpropoxy)prop-2-enamide Chemical compound CC(C)CONC(=O)C=C XZXYVKWNNYKLGA-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
235000014214 soft drink Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Epoxy Resins (AREA)

CA000443024A 1982-12-30 1983-12-12 Enduits aqueux et methode de production Expired CA1238742A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US454,818		1982-12-30
US06/454,818 US4446258A (en)	1982-12-30	1982-12-30	Aqueous coating comprising dispersible epoxy resin-acid polymer ester and diluent polymer, and method of preparation
US454,771		1982-12-30
US06/454,771 US4476262A (en)	1982-12-30	1982-12-30	Aqueous coatings comprising ionic polymer ester and diluent polymer with reduced monomer residue and method of preparation

Publications (1)

Publication Number	Publication Date
CA1238742A true CA1238742A (fr)	1988-06-28

Family

ID=27037601

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000443024A Expired CA1238742A (fr)	1982-12-30	1983-12-12	Enduits aqueux et methode de production

Country Status (1)

Country	Link
CA (1)	CA1238742A (fr)

1983
- 1983-12-12 CA CA000443024A patent/CA1238742A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-06-28	MKEX	Expiry

Publication	Publication Date	Title
US4446258A (en)	1984-05-01	Aqueous coating comprising dispersible epoxy resin-acid polymer ester and diluent polymer, and method of preparation
US4476262A (en)	1984-10-09	Aqueous coatings comprising ionic polymer ester and diluent polymer with reduced monomer residue and method of preparation
CA1166780A (fr)	1984-05-01	Compositions aux polymeres, et methode de production connexe
CA1218783A (fr)	1987-03-03	Preparation de revetements aqueux renfermant un polymere carboxyle dispersable, obtenu a partir d'une resine epoxyde
US5296525A (en)	1994-03-22	Aqueous coating compositions
US4443568A (en)	1984-04-17	Polymerization process and product
US5157078A (en)	1992-10-20	Glycidyl-epoxy-acrylic copolymers
US5212241A (en)	1993-05-18	Glycidyl-epoxy-acrylic copolymers
JPH072929B2 (ja)	1995-01-18	水性被覆組成物
US4482671A (en)	1984-11-13	Base for a graft polymer, novel graft polymer compositions, solvent and water-reducible coatings incorporating the novel graft polymers, and processes for making them
EP0006336B1 (fr)	1982-08-11	Composition d'enduction sous forme d'émulsion aqueuse à base de mélanges auto-émulsifiables estérifiés de polyépoxydes et de copolymères
US5733970A (en)	1998-03-31	Aqueous dispersed, epoxy crosslinked maleated oil microgel polymers for protective coatings
EP0116225B1 (fr)	1989-05-03	Compositions de revêtement aqueuses et procédé pour leur préparation
US5877239A (en)	1999-03-02	Aqueous microgel from carboxyl latex polymer, acrylic-epoxy and diepoxide
US5508325A (en)	1996-04-16	Aqueous dispersed, acrylic grafted epoxy microgel protective coatings
US6034157A (en)	2000-03-07	Process for producing a coating composition
US5532297A (en)	1996-07-02	Divinyl benzene modified, aqueous dispersed, acrylic graft coatings
US5576360A (en)	1996-11-19	Low voc, aqueous dispersed, epoxy crosslinked polyester acrylic coatings
US4501831A (en)	1985-02-26	Aqueous coating compositions and process for their preparation from epoxy acidic acrylic polymer and polyfunctional amine
WO1981001853A1 (fr)	1981-07-09	Copolymeres d'esters epoxy solubles dans l'eau utilises a l'interieur d'une boite
CA1238742A (fr)	1988-06-28	Enduits aqueux et methode de production
EP0979249B1 (fr)	2003-07-30	Procede de production d'une composition de revetement
CA2037581A1 (fr)	1991-09-07	Dispersions aqueuses de polymeres hybrides; compositions de revetement a base de ces dispersions
JPH04122766A (ja)	1992-04-23	水性樹脂組成物