CA2155609A1 - Produit d'addition polyamine-epoxyde dispersable dans l'eau; composition de revetement a base d'epoxyde - Google Patents

Produit d'addition polyamine-epoxyde dispersable dans l'eau; composition de revetement a base d'epoxyde

Info

Publication number: CA2155609A1
Authority: CA; Canada
Prior art keywords: polyamine; epoxy; epoxy adduct; resin; water
Prior art date: 1992-06-03
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.): Abandoned

Application number

CA002155609A

Other languages

English (en)

Inventor

Stuart Paul Darwen

David Arthur Cornforth

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.)

Air Products and Chemicals Inc

Original Assignee

Air Products and Chemicals Inc

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.)

1992-06-03

Filing date

1993-05-26

Publication date

1993-12-04

1992-06-03 Priority claimed from US07/893,151 external-priority patent/US5246984A/en

1993-05-26 Application filed by Air Products and Chemicals Inc filed Critical Air Products and Chemicals Inc

1993-12-04 Publication of CA2155609A1 publication Critical patent/CA2155609A1/fr

Status Abandoned legal-status Critical Current

Links

239000004593 Epoxy Substances 0.000 title claims abstract description 80
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 74
239000008199 coating composition Substances 0.000 title claims abstract description 17
229920006334 epoxy coating Polymers 0.000 title abstract description 7
229920000647 polyepoxide Polymers 0.000 claims abstract description 69
229920005989 resin Polymers 0.000 claims abstract description 59
239000011347 resin Substances 0.000 claims abstract description 59
229920000768 polyamine Polymers 0.000 claims abstract description 52
239000000203 mixture Substances 0.000 claims abstract description 48
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
238000006243 chemical reaction Methods 0.000 claims abstract description 16
150000002118 epoxides Chemical class 0.000 claims abstract description 12
125000003118 aryl group Chemical group 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 23
125000003277 amino group Chemical group 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 8
150000003839 salts Chemical class 0.000 abstract description 6
239000006185 dispersion Substances 0.000 abstract description 5
125000001931 aliphatic group Chemical group 0.000 description 23
239000007787 solid Substances 0.000 description 20
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 19
-1 aliphatic polyol Chemical class 0.000 description 15
239000003822 epoxy resin Substances 0.000 description 14
229920005862 polyol Polymers 0.000 description 14
150000003077 polyols Chemical class 0.000 description 9
238000000576 coating method Methods 0.000 description 8
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 8
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 7
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 5
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000758 substrate Substances 0.000 description 5
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000004721 Polyphenylene oxide Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
229920001281 polyalkylene Polymers 0.000 description 3
229920000570 polyether Polymers 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000005292 vacuum distillation Methods 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
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
GQWWGRUJOCIUKI-UHFFFAOYSA-N 2-[3-(2-methyl-1-oxopyrrolo[1,2-a]pyrazin-3-yl)propyl]guanidine Chemical compound O=C1N(C)C(CCCN=C(N)N)=CN2C=CC=C21 GQWWGRUJOCIUKI-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 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
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003973 paint Substances 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
239000000049 pigment Substances 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 description 1
UWXFTQSKZMNLSA-UHFFFAOYSA-N 2,4,4-trimethylpentanoic acid Chemical compound OC(=O)C(C)CC(C)(C)C UWXFTQSKZMNLSA-UHFFFAOYSA-N 0.000 description 1
VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
ZIAYVOSJNZNSQK-UHFFFAOYSA-N 3-methoxy-n-(3-methoxypropyl)propan-1-amine Chemical compound COCCCNCCCOC ZIAYVOSJNZNSQK-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
241001163743 Perlodes Species 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000010420 art technique Methods 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
GHAUROKXNSHBAG-UHFFFAOYSA-N cyclopentane-1,1-diamine Chemical compound NC1(N)CCCC1 GHAUROKXNSHBAG-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000012827 research and development Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
238000009938 salting Methods 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Epoxy Resins (AREA)
Paints Or Removers (AREA)

CA002155609A 1992-06-03 1993-05-26 Produit d'addition polyamine-epoxyde dispersable dans l'eau; composition de revetement a base d'epoxyde Abandoned CA2155609A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US07/893,151 US5246984A (en)	1992-06-03	1992-06-03	Water dispersible polyamine-epoxy adduct and epoxy coating composition
US07/893151		1992-06-03
CA002097028A CA2097028A1 (fr)	1992-06-03	1993-05-26	Composition de revetement epoxydique avec produit d'addition polyamine-epoxy dispersable dans l'eau

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002097028A Division CA2097028A1 (fr)	1992-06-03	1993-05-26	Composition de revetement epoxydique avec produit d'addition polyamine-epoxy dispersable dans l'eau

Publications (1)

Publication Number	Publication Date
CA2155609A1 true CA2155609A1 (fr)	1993-12-04

Family

ID=25676218

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002155609A Abandoned CA2155609A1 (fr)	1992-06-03	1993-05-26	Produit d'addition polyamine-epoxyde dispersable dans l'eau; composition de revetement a base d'epoxyde

Country Status (1)

Country	Link
CA (1)	CA2155609A1 (fr)

1993
- 1993-05-26 CA CA002155609A patent/CA2155609A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1995-09-14	EEER	Examination request
1999-05-26	FZDE	Discontinued
2023-05-26	FZDE	Discontinued	Effective date: 19990526

Publication	Publication Date	Title
US5350784A (en)	1994-09-27	Water dispersible polyamine-epoxy adduct and epoxy coating composition
US5489630A (en)	1996-02-06	Self-emulsifying epoxy curing agent
CA2055796C (fr)	1996-07-30	Agent de reticulation de resine epoxyde dispersable dans l'eau
US5310770A (en)	1994-05-10	Water reducible epoxy-amine adducts based on the diglycidyl ether of cyclohexane dimethanol
CA2309699C (fr)	2009-04-28	Agents de durcissement compatibles avec l'eau pour resines epoxydes
US5847027A (en)	1998-12-08	Hardeners for elastic epoxy resin systems
US7358312B2 (en)	2008-04-15	Epoxy resin curing agent of epoxy resin-liquid amine adduct and polyamidoamine
EP2961784A1 (fr)	2016-01-06	Composition et procédé de fabrication de durcisseur époxy aqueux pour utilisation dans des composés autolissants époxy à deux composants ayant des caractéristiques de longue vie en pot, durcissement rapide et faible retrait
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DK2545121T3 (en)	2016-11-28	STORAGE-STABLE WATER-BASED EPOXY-AMINE HARDWARE SYSTEMS
CA1064892A (fr)	1979-10-23	Produit de cure pour resines epoxydiques
EP0786481B1 (fr)	2002-04-03	Accélérateurs réactifs pour des résines époxydes durcies par des amines
US5798398A (en)	1998-08-25	Epoxy curing agent comprising a metaxylylenediamine-epichlorohydrin adduct
EP4288477B1 (fr)	2024-11-13	Agents de durcissement époxy et leurs utilisations
CA2155609A1 (fr)	1993-12-04	Produit d'addition polyamine-epoxyde dispersable dans l'eau; composition de revetement a base d'epoxyde
US20070066789A1 (en)	2007-03-22	Hardeners for coating compositions (I)
JP2001122947A (ja)	2001-05-08	エポキシ樹脂用硬化促進剤及びそれを用いてなるエポキシ樹脂組成物
JPH0748434A (ja)	1995-02-21	水性ポリエポキシド樹脂組成物
JPH05155983A (ja)	1993-06-22	エポキシ樹脂組成物及びその硬化物
JPH10139861A (ja)	1998-05-26	水性エポキシド樹脂組成物
JPH10101774A (ja)	1998-04-21	水性エポキシド樹脂組成物