CA1280842C - Self-crosslinkable electrocoat resins prepared by room temperature reactions of epoxy resins and polyamines containing primary and tertiary amine groups - Google Patents

Self-crosslinkable electrocoat resins prepared by room temperature reactions of epoxy resins and polyamines containing primary and tertiary amine groups

Info

Publication number: CA1280842C
Authority: CA; Canada
Prior art keywords: coating composition; composition according; electrodepositable coating; epoxide; amine
Prior art date: 1983-10-31
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

CA000465974A

Other languages

English (en)

French (fr)

Inventor

Robert A. Swider

Martha E. Horsch

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.)

Ford Motor Company of Canada Ltd

Ford Motor Co

Original Assignee

Ford Motor Company of Canada Ltd

Ford Motor 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.)

1983-10-31

Filing date

1984-10-19

Publication date

1991-02-26

1983-10-31 Priority claimed from US06/563,422 external-priority patent/US4515911A/en

1984-10-19 Application filed by Ford Motor Company of Canada Ltd, Ford Motor Co filed Critical Ford Motor Company of Canada Ltd

1991-02-26 Application granted granted Critical

1991-02-26 Publication of CA1280842C publication Critical patent/CA1280842C/en

2008-02-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 81
239000011347 resin Substances 0.000 title claims abstract description 81
229920000768 polyamine Polymers 0.000 title claims abstract description 43
229920000647 polyepoxide Polymers 0.000 title claims abstract description 31
239000003822 epoxy resin Substances 0.000 title claims abstract description 25
125000002924 primary amino group Chemical class [H]N([H])* 0.000 title claims abstract 8
125000001302 tertiary amino group Chemical group 0.000 title claims abstract 5
238000006243 chemical reaction Methods 0.000 title description 19
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 title description 9
239000008199 coating composition Substances 0.000 claims abstract description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
150000001412 amines Chemical class 0.000 claims abstract description 24
125000003277 amino group Chemical group 0.000 claims abstract description 24
239000002253 acid Substances 0.000 claims abstract description 20
239000006185 dispersion Substances 0.000 claims abstract description 7
150000002118 epoxides Chemical class 0.000 claims abstract 16
239000000203 mixture Substances 0.000 claims description 35
239000011541 reaction mixture Substances 0.000 claims description 22
239000000376 reactant Substances 0.000 claims description 17
239000003431 cross linking reagent Substances 0.000 claims description 15
-1 Cellosolve ether compounds Chemical class 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims 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 claims description 7
238000000034 method Methods 0.000 claims description 6
150000002170 ethers Chemical class 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 4
229920001568 phenolic resin Polymers 0.000 claims description 4
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
230000003472 neutralizing effect Effects 0.000 claims description 3
125000005498 phthalate group Chemical class 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
150000002763 monocarboxylic acids Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims 2
238000000576 coating method Methods 0.000 abstract description 30
239000011248 coating agent Substances 0.000 abstract description 18
238000005260 corrosion Methods 0.000 abstract description 10
230000007797 corrosion Effects 0.000 abstract description 10
239000000758 substrate Substances 0.000 abstract description 6
239000002184 metal Substances 0.000 abstract description 3
229910052751 metal Inorganic materials 0.000 abstract description 3
150000002924 oxiranes Chemical group 0.000 description 27
239000000126 substance Substances 0.000 description 17
229910000831 Steel Inorganic materials 0.000 description 10
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
239000010959 steel Substances 0.000 description 10
239000003973 paint Substances 0.000 description 9
239000002987 primer (paints) Substances 0.000 description 9
150000003512 tertiary amines Chemical group 0.000 description 9
238000004132 cross linking Methods 0.000 description 8
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical class CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
150000003141 primary amines Chemical class 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
238000012360 testing method Methods 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
239000011701 zinc Substances 0.000 description 6
UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 5
239000004593 Epoxy Substances 0.000 description 5
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 5
239000006229 carbon black Substances 0.000 description 5
239000008367 deionised water Substances 0.000 description 5
229910021641 deionized water Inorganic materials 0.000 description 5
239000004310 lactic acid Substances 0.000 description 5
235000014655 lactic acid Nutrition 0.000 description 5
239000007921 spray Substances 0.000 description 5
229910001220 stainless steel Inorganic materials 0.000 description 5
239000010935 stainless steel Substances 0.000 description 5
239000003760 tallow Substances 0.000 description 5
229920003180 amino resin Polymers 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000000463 material Substances 0.000 description 4
229920001187 thermosetting polymer Polymers 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
239000004971 Cross linker Substances 0.000 description 3
102100020740 Dolichol phosphate-mannose biosynthesis regulatory protein Human genes 0.000 description 3
101000932183 Homo sapiens Dolichol phosphate-mannose biosynthesis regulatory protein Proteins 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002091 cationic group Chemical group 0.000 description 3
238000004070 electrodeposition Methods 0.000 description 3
239000000049 pigment Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229940105325 3-dimethylaminopropylamine Drugs 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 2
229910000165 zinc phosphate Inorganic materials 0.000 description 2
BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
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 1
AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920003319 Araldite® Polymers 0.000 description 1
241000905957 Channa melasoma Species 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920002396 Polyurea Polymers 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
150000001408 amides Chemical group 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
NUUPJBRGQCEZSI-UHFFFAOYSA-N cyclopentane-1,3-diol Chemical compound OC1CCC(O)C1 NUUPJBRGQCEZSI-UHFFFAOYSA-N 0.000 description 1
229960002380 dibutyl phthalate Drugs 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
238000009533 lab test Methods 0.000 description 1
229940043265 methyl isobutyl ketone Drugs 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
JILXUIANNUALRZ-UHFFFAOYSA-N n',n'-diethylbutane-1,4-diamine Chemical compound CCN(CC)CCCCN JILXUIANNUALRZ-UHFFFAOYSA-N 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920003226 polyurethane urea Polymers 0.000 description 1
AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003335 secondary amines Chemical group 0.000 description 1
238000010998 test method Methods 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
239000008096 xylene Substances 0.000 description 1

Landscapes

Paints Or Removers (AREA)

CA000465974A 1983-10-31 1984-10-19 Self-crosslinkable electrocoat resins prepared by room temperature reactions of epoxy resins and polyamines containing primary and tertiary amine groups Expired - Lifetime CA1280842C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US563,422		1983-10-31
US06/563,422 US4515911A (en)	1983-10-31	1983-10-31	Self-crosslinkable electrocoat resins prepared by room temperature reactions by epoxy resins and polyamines containing primary and tertiary amine groups

Publications (1)

Publication Number	Publication Date
CA1280842C true CA1280842C (en)	1991-02-26

Family

ID=24250432

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000465974A Expired - Lifetime CA1280842C (en)	1983-10-31	1984-10-19	Self-crosslinkable electrocoat resins prepared by room temperature reactions of epoxy resins and polyamines containing primary and tertiary amine groups

Country Status (6)

Country	Link
CA (1)	CA1280842C (it)
ES (1)	ES8603595A1 (it)
IT (1)	IT1178181B (it)
NZ (1)	NZ210034A (it)
PT (1)	PT79412B (it)
ZA (1)	ZA847802B (it)

1984
- 1984-10-04 ZA ZA847802A patent/ZA847802B/xx unknown
- 1984-10-19 CA CA000465974A patent/CA1280842C/en not_active Expired - Lifetime
- 1984-10-26 PT PT79412A patent/PT79412B/pt not_active IP Right Cessation
- 1984-10-26 ES ES537084A patent/ES8603595A1/es not_active Expired
- 1984-10-30 NZ NZ210034A patent/NZ210034A/en unknown
- 1984-10-30 IT IT49089/84A patent/IT1178181B/it active

Also Published As

Publication number	Publication date
PT79412B (en)	1986-09-15
ES537084A0 (es)	1985-12-16
PT79412A (en)	1984-11-01
IT1178181B (it)	1987-09-09
ZA847802B (en)	1985-05-29
IT8449089A1 (it)	1986-04-30
IT8449089A0 (it)	1984-10-30
ES8603595A1 (es)	1985-12-16
NZ210034A (en)	1988-01-08

Legal Events

Date	Code	Title	Description
1993-08-31	MKLA	Lapsed

Publication	Publication Date	Title
KR930002457B1 (ko)	1993-04-02	우레탄 폴리올을 사용하는 에폭시 수지의 개선
US4588783A (en)	1986-05-13	Amide-containing polyhydroxyethyl carbamates
US4515911A (en)	1985-05-07	Self-crosslinkable electrocoat resins prepared by room temperature reactions by epoxy resins and polyamines containing primary and tertiary amine groups
EP0494895A1 (en)	1992-07-22	Electrodeposition coatings containing blocked tetramethylxylene diisocyanate crosslinker
US5070149A (en)	1991-12-03	Cationic resin composition with reduced emissions during baking
US4536558A (en)	1985-08-20	Chain extended epoxy-ester polymeric compositions for cationic electrodeposition
US5225461A (en)	1993-07-06	Amino group-containing, lactone-modified epoxy resin with polyisocyanate
JPH01501069A (ja)	1989-04-13	陽イオン性エポキシ樹脂をベースとする組成物の被覆方法
US5472998A (en)	1995-12-05	Polymeric additive for cathodic electrocoating compositions for improved throw power
CA2088262C (en)	2002-04-09	Amide diol extended cathodic electrodeposition resins
JP2659062B2 (ja)	1997-09-30	被覆用樹脂組成物
AU565348B2 (en)	1987-09-10	Self-crosslinkable electrocoat resins prepared by room temperature reactions of epoxy resins and polyamines containing primary and tertiary amine groups
EP0162837B1 (en)	1991-12-11	Self-crosslinkable electrocoat resins prepared by room temperature reactions of epoxy resins and fatty amidopolyamines
CA1280842C (en)	1991-02-26	Self-crosslinkable electrocoat resins prepared by room temperature reactions of epoxy resins and polyamines containing primary and tertiary amine groups
US4568710A (en)	1986-02-04	Self-crosslinkable electrocoat resins prepared by room temperature reactions of epoxy resins and fatty amidopolyamines
US5126413A (en)	1992-06-30	Addition product of lactone-modified epoxy resin with polyphenol and amino compounds
US5371120A (en)	1994-12-06	Crosslinked microgel for cathodic electrocoating compositions
US5416137A (en)	1995-05-16	Cathodic electrocoating compositions having improved throw power, containing multifunctional phenols
US5382607A (en)	1995-01-17	Cathodic electrodeposition coatings containing zinc hydroxyphosphite pigment
US5057558A (en)	1991-10-15	Polyol extended cathodic electrodeposition resins
CA2088259A1 (en)	1992-02-07	Method of incorporating polyamine into a cationic resin
CA2001700A1 (en)	1990-05-23	Urethane diol extended cathodic electrodeposition resins
JP2001354910A (ja)	2001-12-25	カチオン電着塗料組成物