WO1996014363B1 - Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition - Google Patents
Cationic resin and capped polyisocyanate curing agent suitable for use in electrodepositionInfo
- Publication number
- WO1996014363B1 WO1996014363B1 PCT/US1995/012993 US9512993W WO9614363B1 WO 1996014363 B1 WO1996014363 B1 WO 1996014363B1 US 9512993 W US9512993 W US 9512993W WO 9614363 B1 WO9614363 B1 WO 9614363B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- groups
- phenolic hydroxyl
- composition
- beta
- Prior art date
Links
- 229920005989 resin Polymers 0.000 title claims abstract 16
- 239000011347 resin Substances 0.000 title claims abstract 16
- 125000002091 cationic group Chemical group 0.000 title claims abstract 7
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract 6
- 239000005056 polyisocyanate Substances 0.000 title claims abstract 6
- 239000003795 chemical substances by application Substances 0.000 title claims abstract 3
- 238000004070 electrodeposition Methods 0.000 title claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract 18
- 125000004185 ester group Chemical group 0.000 claims abstract 11
- 239000007787 solid Substances 0.000 claims abstract 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract 5
- 229920000647 polyepoxide Polymers 0.000 claims abstract 4
- 239000000758 substrate Substances 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 12
- 239000000463 material Substances 0.000 claims 6
- 239000004593 Epoxy Substances 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000007142 ring opening reaction Methods 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 abstract 2
- 239000010959 steel Substances 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
Abstract
An electrodepositable composition is provided comprising: (A) a non-gelled cationic resin which is derived from a polyepoxide and which contains in the resin molecule cationic salt groups and active hydrogen groups selected from aliphatic hydroxyl and primary and secondary amino; and present as a separate component; (B) a fully capped polyisocyanate curing agent containing substantially no free isocyanate groups. The electrodepositable composition contains from about 0.02 to 1.0 milliequivalents phenolic hydroxyl groups per gram of resin solids, and from about 0.1 to 2.0 milliequivalents beta-hydroxy ester groups per gram of resin solids. The composition provides excellent corrosion resistance when electrodeposited over steel substrates, and does not require lead in the formulation nor the use of a conventional chrome rinse for the steel substrate pretreatment before electrodeposition.
Claims
- 45 -
AMENDED CLAIMS
[received by the International Bureau on 15 May 1996 (15.05.96) ; new claims 36-46 added; remaining claims unchanged (4 pages)]
36. The composition of claim l or the method of claim 19 in which the electrodepositable composition further comprises a separate component (C) and a separate component (D) and the phenolic hydroxyl groups are present in one and the beta- hydroxy ester groups are present in the other; and (C) and (D) are different from (A) and (B) and from one another.
37. The composition of claim 1 or the method of claim 19 wherein the phenolic hydroxyl groups are present as unreacted phenolic hydroxyl groups in component (A) through reaction of polyhydric phenol with polyepoxide in chain extension with polyhydroxyl group-containing material where the polyhydric phenol is in a stoichiometric excess.
38. The method of claim 19, wherein the beta-hydroxy ester groups are present in component (A) through ring opening reaction of the 1,2-epoxide groups of the polyepoxide with a material having at least one carboxylic acid group.
39. The composition of Claim l or the method of claim 19 in which the phenolic hydroxyl groups are free unreacted phenolic hydroxyl groups in the electrodepositable composition.
40. The composition of Claim 1 or the method of claim 19 wherein the phenolic hydroxyl groups are present as free unreacted phenolic hydroxyl groups in component (B) by capping the isocyanate groups of the polyisocyanate with materials selected from the group consisting of: i) materials having an aliphatic and phenolic hydroxyl group, and ii) a hydroxyl functional epoxide which is further reacted with a stoichiometric excess of a polyhydric phenol.
41. The composition of Claim 1 or the method of claim 19, wherein the beta-hydroxy ester groups are present in component (B) through reaction of isocyanate groups of the polyisocyanate with a hydroxyl
AMENDED SHEET {ARTICLE 19)
46
group of a hydroxyl grou -containing carboxylic acid and reacting the acid group of the reacted hydroxyl group-containing carboxylic acid with an epoxy functional material to have ring opening of the 1,2- epoxide group of the epoxy functional material to form the beta- hydroxy ester groups.
42. The composition of Claim 10 or the method of claim 36 wherein the electrodepositable composition has present on a percent by weight basis of the weight of resin solids an amount of component (A) from 15 to 85, of component (B) from 15 to 85, of component (C) up to 30, and of component (D) up to 30.
43. The composition of Claim 1 or the method of claim 19 wherein in the electrodepositable composition the polyisocyanate is present in component (B) in an amount to provide 0.1 to about 1.2 capped isocyanate groups for each active hydrogen in the resin of component (A) , and component (A) has an equivalent ratio of reactants of epoxy to polyhydroxyl of from about 1.00:0.75 to 1.00:2.00 and has about 0.1 to 3.0 milliequivalent of cationic salt group per gram of resin solids.
44. A method of electrocoating an electroconductive substrate which serves as a cathode in an electrical circuit comprising said cathode and an anode immersed in an aqueous electrodepositable composition containing a cationic water dispersible resin, said method comprising passing an electric current between the anode and the cathode to cause the electrodepositable composition to deposit on the cathode as a substantially continuous film, and heating the electrodeposited film at an elevated temperature to cure the film, wherein the electrodepositable composition comprises:
(A) a cationic resin which is derived from a polyepoxide and which contains in the resin cationic salt groups and active hydrogen groups selected from aliphatic hydroxyl... primary amino, and secondary amino,- and
- 47 -
present as a separate component
(B) a fully capped polyisocyanate curing agent containing substantially no free isocyanate groups; as separate from components (A) and (B) (C) a component selected from the group consisting of a component having phenolic hydroxyl groups to provide to said electrodepositable composition from about 0.02 to 1.0 milliequivalents phenolic hydroxyl groups calculated as
per gram of resin solids, and a component having beta-hydroxy ester groups to provide said electrodepositable composition from about 0.1 to 2.0 milliequivalents of beta-hydroxy ester groups calculated as
— CH— CH — O — C—
2 Formula 2
per gram of resin solids and a component having both the phenolic hydroxyl groups and the beta-hydroxy ester groups to provide said electrodepositable composition from about 0.02 to 1.0 milli¬ equivalents of phenolic hydroxyl groups as calculated from Formula (1) and about 0.1 to 2.0 milliequivalents of beta-hydroxy ester groups as calculated from Formula (2) , said electrodepositable composition being characterized as containing both from about 0.02 to 1.0 milliequivalents phenolic hydroxyl groups as calculated from Formula (1) per gram of resin solids, and from about 0.1 to 2.0 milliequivalents beta-hydroxy ester groups as calculated from Formula (2) per gram of resin solids.
45. The method of claim 44 in which the electrodepositable composition further comprises in addition to component (C) a separate
48
component (D) and the phenolic hydroxyl groups are present in one and the beta-hydroxy ester groups are present in the other; and (C) and (D) are different from (A) and (B) and from one another.
46. The method of claim 45 wherein the electrodepositable composition has present on a percent by weight basis of the weight of resin solids an amount of component (A) from 15 to 85, of component (B) from 15 to 85, of component (C) up to 30, and of component <D) up to 30.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95938194A EP0789732B1 (en) | 1994-11-04 | 1995-10-17 | Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition |
| KR1019970702963A KR100211079B1 (en) | 1994-11-04 | 1995-10-17 | Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition |
| CA002204434A CA2204434C (en) | 1994-11-04 | 1995-10-17 | Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition |
| AU38918/95A AU691046B2 (en) | 1994-11-04 | 1995-10-17 | Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition |
| JP08515310A JP3110047B2 (en) | 1994-11-04 | 1995-10-17 | Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition |
| DE69510951T DE69510951T2 (en) | 1994-11-04 | 1995-10-17 | CATIONIC RESIN AND CAPPED POLYISOCYANATE AS A CROSS-LINKING AGENT SUITABLE FOR USE IN ELECTRIC DIP COATING |
| MXPA/A/1997/003240A MXPA97003240A (en) | 1994-11-04 | 1997-05-02 | Cationic resin and cured polyisocianate curing agent suitable for employment in electrodeposic |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/334,712 US5582704A (en) | 1994-11-04 | 1994-11-04 | Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition |
| US08/334,712 | 1994-11-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996014363A1 WO1996014363A1 (en) | 1996-05-17 |
| WO1996014363B1 true WO1996014363B1 (en) | 1996-08-01 |
Family
ID=23308478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1995/012993 WO1996014363A1 (en) | 1994-11-04 | 1995-10-17 | Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US5582704A (en) |
| EP (1) | EP0789732B1 (en) |
| JP (2) | JP3110047B2 (en) |
| KR (1) | KR100211079B1 (en) |
| CN (1) | CN1128849C (en) |
| AT (1) | ATE182353T1 (en) |
| AU (1) | AU691046B2 (en) |
| CA (1) | CA2204434C (en) |
| DE (1) | DE69510951T2 (en) |
| ES (1) | ES2136884T3 (en) |
| MY (1) | MY113409A (en) |
| TR (1) | TR199501366A2 (en) |
| TW (1) | TW339352B (en) |
| WO (1) | WO1996014363A1 (en) |
| ZA (1) | ZA958960B (en) |
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| US5074979B1 (en) * | 1990-06-20 | 1995-02-28 | Ppg Industries Inc | Cationic resin containing blocked isocyanate groups suitable for use in electrodeposition |
| US5096556A (en) * | 1990-06-25 | 1992-03-17 | Ppg Industries, Inc. | Cationic microgels and their use in electrodeposition |
| US5416137A (en) * | 1994-06-01 | 1995-05-16 | E. I. Du Pont De Nemours And Company | Cathodic electrocoating compositions having improved throw power, containing multifunctional phenols |
-
1994
- 1994-11-04 US US08/334,712 patent/US5582704A/en not_active Expired - Fee Related
-
1995
- 1995-10-17 DE DE69510951T patent/DE69510951T2/en not_active Expired - Fee Related
- 1995-10-17 AU AU38918/95A patent/AU691046B2/en not_active Ceased
- 1995-10-17 JP JP08515310A patent/JP3110047B2/en not_active Expired - Fee Related
- 1995-10-17 ES ES95938194T patent/ES2136884T3/en not_active Expired - Lifetime
- 1995-10-17 CA CA002204434A patent/CA2204434C/en not_active Expired - Fee Related
- 1995-10-17 WO PCT/US1995/012993 patent/WO1996014363A1/en active IP Right Grant
- 1995-10-17 CN CN95196522A patent/CN1128849C/en not_active Expired - Fee Related
- 1995-10-17 EP EP95938194A patent/EP0789732B1/en not_active Expired - Lifetime
- 1995-10-17 KR KR1019970702963A patent/KR100211079B1/en not_active Expired - Fee Related
- 1995-10-17 AT AT95938194T patent/ATE182353T1/en not_active IP Right Cessation
- 1995-10-23 ZA ZA958960A patent/ZA958960B/en unknown
- 1995-11-02 MY MYPI95003307A patent/MY113409A/en unknown
- 1995-11-03 TR TR95/01366A patent/TR199501366A2/en unknown
- 1995-11-16 TW TW084112163A patent/TW339352B/en active
-
1996
- 1996-10-01 US US08/724,343 patent/US5760107A/en not_active Expired - Lifetime
-
2000
- 2000-06-05 JP JP2000168305A patent/JP2001026744A/en active Pending
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