CA1119331A - Substance de revetement portee dans l'eau, thermodurcissable, a base de resine de type azote, contenant des groupements epoxydes et amino - Google Patents

Substance de revetement portee dans l'eau, thermodurcissable, a base de resine de type azote, contenant des groupements epoxydes et amino

Info

Publication number: CA1119331A
Authority: CA; Canada
Prior art keywords: amine; composition; weight; epoxy; dimethyl
Prior art date: 1978-02-08
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

CA000296642A

Other languages

English (en)

Inventor

Eugene G. Sommerfeld

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.)

1978-02-08

Filing date

1978-02-08

Publication date

1982-03-02

1978-02-08 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1978-02-08 Priority to CA000296642A priority Critical patent/CA1119331A/fr

1982-03-02 Application granted granted Critical

1982-03-02 Publication of CA1119331A publication Critical patent/CA1119331A/fr

Status Expired legal-status Critical Current

Links

239000004593 Epoxy Substances 0.000 title claims abstract description 62
239000008199 coating composition Substances 0.000 title claims abstract description 47
125000003700 epoxy group Chemical group 0.000 title claims abstract description 18
229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title abstract description 36
239000011347 resin Substances 0.000 title abstract description 28
229920005989 resin Polymers 0.000 title abstract description 28
229910052757 nitrogen Inorganic materials 0.000 title abstract description 18
125000003277 amino group Chemical group 0.000 title 1
239000000203 mixture Substances 0.000 claims abstract description 87
229920000642 polymer Polymers 0.000 claims abstract description 62
150000003512 tertiary amines Chemical class 0.000 claims abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
-1 dimethyl 3-hydroxy-1-propyl Chemical group 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 18
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
239000007788 liquid Substances 0.000 claims description 16
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 12
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 12
229960002887 deanol Drugs 0.000 claims description 12
239000012972 dimethylethanolamine Substances 0.000 claims description 12
239000000178 monomer Substances 0.000 claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 9
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 8
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 8
HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
239000003377 acid catalyst Substances 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 7
229940031098 ethanolamine Drugs 0.000 claims description 7
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 6
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 5
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 5
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 5
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 5
239000004793 Polystyrene Substances 0.000 claims description 5
229940063557 methacrylate Drugs 0.000 claims description 5
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 5
ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims description 5
GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 5
229920002223 polystyrene Polymers 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
238000005227 gel permeation chromatography Methods 0.000 claims description 4
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 3
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000005690 diesters Chemical class 0.000 claims description 2
235000020354 squash Nutrition 0.000 claims 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 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 2
YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 claims 2
OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims 2
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 2
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims 2
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
238000000576 coating method Methods 0.000 abstract description 38
239000006185 dispersion Substances 0.000 abstract description 11
238000004070 electrodeposition Methods 0.000 abstract description 9
239000000758 substrate Substances 0.000 abstract description 9
229910052751 metal Inorganic materials 0.000 abstract description 7
239000002184 metal Substances 0.000 abstract description 7
235000013361 beverage Nutrition 0.000 abstract description 6
235000013305 food Nutrition 0.000 abstract description 4
238000005260 corrosion Methods 0.000 abstract description 3
230000007797 corrosion Effects 0.000 abstract description 3
230000003301 hydrolyzing effect Effects 0.000 abstract 1
238000003754 machining Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 33
239000011248 coating agent Substances 0.000 description 31
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 18
239000000047 product Substances 0.000 description 13
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
125000001453 quaternary ammonium group Chemical group 0.000 description 12
239000007787 solid Substances 0.000 description 12
150000001412 amines Chemical class 0.000 description 11
238000000034 method Methods 0.000 description 11
235000011114 ammonium hydroxide Nutrition 0.000 description 10
150000007974 melamines Chemical class 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000003431 cross linking reagent Substances 0.000 description 9
229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 9
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 9
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
239000003822 epoxy resin Substances 0.000 description 8
229920000647 polyepoxide Polymers 0.000 description 8
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 description 7
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
229910052782 aluminium Inorganic materials 0.000 description 6
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
239000007921 spray Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229920000877 Melamine resin Polymers 0.000 description 5
229920003265 Resimene® Polymers 0.000 description 5
238000009835 boiling Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
125000002768 hydroxyalkyl group Chemical group 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
235000013405 beer Nutrition 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
125000005395 methacrylic acid group Chemical group 0.000 description 4
229920003986 novolac Polymers 0.000 description 4
BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
229910000831 Steel Inorganic materials 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
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 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000010959 steel Substances 0.000 description 3
239000005029 tin-free steel Substances 0.000 description 3
150000003672 ureas Chemical class 0.000 description 3
238000009736 wetting Methods 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-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
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229920003180 amino resin Polymers 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000000903 blocking effect Effects 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
238000005266 casting Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000005336 cracking Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012632 extractable Substances 0.000 description 2
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000002829 nitrogen Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000009928 pasteurization Methods 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
239000005028 tinplate Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
229940058015 1,3-butylene glycol Drugs 0.000 description 1
DYUUGILMVYJEHY-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-4,4,5,5-tetramethyl-3-oxido-2-phenylimidazol-3-ium Chemical compound CC1(C)C(C)(C)N([O])C(C=2C=CC=CC=2)=[N+]1[O-] DYUUGILMVYJEHY-UHFFFAOYSA-N 0.000 description 1
WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
JJRUAPNVLBABCN-UHFFFAOYSA-N 2-(ethenoxymethyl)oxirane Chemical compound C=COCC1CO1 JJRUAPNVLBABCN-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
206010001497 Agitation Diseases 0.000 description 1
102100022618 COMM domain-containing protein 6 Human genes 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
229920013683 Celanese Polymers 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
241000543381 Cliftonia monophylla Species 0.000 description 1
241000518994 Conta Species 0.000 description 1
241000006460 Cyana Species 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
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101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
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241001527806 Iti Species 0.000 description 1
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101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
241001163743 Perlodes Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
238000005452 bending Methods 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
235000019437 butane-1,3-diol Nutrition 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
230000032798 delamination Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000003599 detergent Substances 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000504 effect on taste Effects 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000001879 gelation Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000000383 hazardous chemical Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229920001480 hydrophilic copolymer Polymers 0.000 description 1
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
239000003999 initiator Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000035515 penetration Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003348 petrochemical agent Substances 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003242 quaternary ammonium salts Chemical group 0.000 description 1
238000007761 roller coating Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000013589 supplement Substances 0.000 description 1
HLCHESOMJVGDSJ-UHFFFAOYSA-N thiq Chemical compound C1=CC(Cl)=CC=C1CC(C(=O)N1CCC(CN2N=CN=C2)(CC1)C1CCCCC1)NC(=O)C1NCC2=CC=CC=C2C1 HLCHESOMJVGDSJ-UHFFFAOYSA-N 0.000 description 1
UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
229920001567 vinyl ester resin Polymers 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

Landscapes

Paints Or Removers (AREA)

CA000296642A 1978-02-08 1978-02-08 Substance de revetement portee dans l'eau, thermodurcissable, a base de resine de type azote, contenant des groupements epoxydes et amino Expired CA1119331A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000296642A CA1119331A (fr)	1978-02-08	1978-02-08	Substance de revetement portee dans l'eau, thermodurcissable, a base de resine de type azote, contenant des groupements epoxydes et amino

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000296642A CA1119331A (fr)	1978-02-08	1978-02-08	Substance de revetement portee dans l'eau, thermodurcissable, a base de resine de type azote, contenant des groupements epoxydes et amino

Publications (1)

Publication Number	Publication Date
CA1119331A true CA1119331A (fr)	1982-03-02

Family

ID=4110738

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000296642A Expired CA1119331A (fr)	1978-02-08	1978-02-08	Substance de revetement portee dans l'eau, thermodurcissable, a base de resine de type azote, contenant des groupements epoxydes et amino

Country Status (1)

Country	Link
CA (1)	CA1119331A (fr)

1978
- 1978-02-08 CA CA000296642A patent/CA1119331A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-03-02	MKEX	Expiry

Publication	Publication Date	Title
US4076676A (en)	1978-02-28	Aqueous coating composition from aminoplast and reaction product of tertiary amine and polymer containing terminal epoxy groups
US4247439A (en)	1981-01-27	Water-borne coating composition made from epoxy resin, polymeric acid and tertiary amine
US4302373A (en)	1981-11-24	Water-borne coating composition made from modified epoxy resin, polymeric acid and tertiary amine
US4423165A (en)	1983-12-27	Water-borne coating composition made from epoxy resin, first polymeric acid, tertiary amine and second polymeric acid
US4076675A (en)	1978-02-28	Aqueous coating composition from aminoplast and reaction product of tertiary amine and polymer containing randomly distributed epoxy groups
CA1165484A (fr)	1984-04-10	Suspensions aqueuses stables de resines en melange
US4018848A (en)	1977-04-19	High solids can coating compositions based on epoxy resin, crosslinking agent, flexibilizing polyol, co-reactive acid catalyst, and surface modifier
US4943359A (en)	1990-07-24	Process for applying an aqueous, heat-curable coating to cans
EP0428316B1 (fr)	1994-04-27	Compositions de revêtement aqueuses à base d'une résine époxyde et d'une résine acrylique
US4303488A (en)	1981-12-01	Electrocoating with water-borne coating composition made from epoxy resin, polymeric acid and tertiary amine
US4136075A (en)	1979-01-23	Acrylic copolymer coatings
CA1104297A (fr)	1981-06-30	Produits d'addition d'aldehydes pour resines epoxydes et enduits pour boites de conserves
JPS625950B2 (fr)	1987-02-07
US3716402A (en)	1973-02-13	Film forming compositons from polycarboxylic acids and adducts of polyepoxides and amines
US4789707A (en)	1988-12-06	Coating resin composition with high number of imino groups
US4740566A (en)	1988-04-26	High gloss color keyed guide coat
US4174333A (en)	1979-11-13	Carboxylated amide polymers and coating compositions containing same
EP0195660A2 (fr)	1986-09-24	Compositions de revêtement à haute teneur en matières solides
US4423168A (en)	1983-12-27	Resinous compositions curable through a transesterification curing mechanism
CA1100663A (fr)	1981-05-05	Liants a deposer par voie cathodique
EP0000086B1 (fr)	1982-04-14	Liants résineux contenant des groupes amino et leur procédé de préparation
JP2799401B2 (ja)	1998-09-17	塗料用エポキシ樹脂組成物
US4283428A (en)	1981-08-11	Beverage containers coated with a water-based liner
CA1099044A (fr)	1981-04-07	Traduction non-disponible
US4605476A (en)	1986-08-12	Resinous blends of epoxy and acrylic resins and the use thereof in electrodeposition