Hardening agent for aqueous epoxy resin compositions

• US 4,197,389 A
• Filed: 07/12/1978
• Issued: 04/08/1980
• Est. Priority Date: 07/18/1977
• Status: Expired due to Term

• Current Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Original Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Inventors: Becker, Wilhelm, Karasmann, Horst
• Primary Examiner(s): Nielsen, Earl A.
• Application Number:
  US05/924,050
• Time in Patent Office: 636 Days
• Field of Search: 260/29.2 EP, 260/830 TW, 260/573, 260/584 B, 528/103, 528/135, 528/111, 528/393, 528/407, 252/182
• US Class Current: 523/420
• CPC Class Codes: C08G 59/184 with amines
• CPC Class Codes: Y10T 428/31511 Of epoxy ether
• CPC Class Codes: Y10T 428/31525 Next to glass or quartz
• CPC Class Codes: Y10T 428/31529 Next to metal

Abstract

A hardening agent for an aqueous epoxy resin composition comprising a reaction product of (a) at least one polyepoxide compound, (b) at least one polyalkylene polyether polyol and (c) at least one compound selected from the group consisting of aliphatic, cycloaliphatic and heterocyclic polyamine and wherein component (c) additionally may be reacted with (d) an unsaturated compound before or after the reaction with the adduct of components (a) and (b), process for preparing said hardening agent and hardenable film forming coating compositions comprising as essential ingredients said hardening agent, at least one polyfunctional epoxy compound (a) and water.

Claims

1. A hardening agent for an aqueous epoxy resin composition comprising a reaction product of an adduct, obtained in a first reaction step, of (a) at least one polyepoxide compound and (b) at least one polyalkylene polyether polyol, with (c) at least one compound selected from the group consisting of aliphatic, cycloaliphatic and heterocyclic polyamine.

2. A hardening agent as claimed in claim 1 wherein (a) is at least one water-insoluble polyepoxide compound and (b) is at least one water-soluble polyalkylene polyether polyol.

3. A hardening agent as claimed in claim 1 comprising a reaction product obtained from 20 to 80% by weight of an adduct derived from (a) 2 to 4 equivalents of at least one polyepoxide compound and (b) 0.2 to 1.5 equivalents of at least one polyalkylene polyether polyol by reaction with 80 to 20% by weight of component (c) comprising at least one polyamine, the quantity of amine used being in 2 to 10 times excess, relative to the reacting epoxide groups and hydrogen atoms bonded to the nitrogen.

4. A hardening agent as claimed in claim 1 wherein additionally (d) an unsaturated compound is reacted by addition with the component (c) before or after the reaction with the adduct of components (a) and (b).

5. A hardening agent as claimed in claim 4 whereby for each hydrogen atom bonded to the nitrogen of component (c), this component is reacted by addition before or after the reaction with the adduct of components (a) and (b) with up to 0.5 equivalents of an unsaturated compound (d) of the formula HC(R₁)═

C(R₂)--X wherein R₁ is selected from the group consisting of H, --CH₃ and --C₂ H₅, R₂ is selected from the group consisting of H and --CH₃ and X is selected from the group consisting of --CN, --COOH, --COOCH₃, --COOC₂ H₅, --COOC₃ H₇, --COOC₄ H₉, --CONH₂.

10. Hardenable film forming coating compositions comprising as essential ingredients a hardening agent as claimed in claim 1, at least one compound having more than one epoxy group and water.

6. A process for the preparation of a hardening agent for aqueous epoxy resin compositions wherein in a first step an adduct consisting of (a) at least one polyepoxide compound and (b) at least one polyalkylene polyether polyol with an average molecular weight of from 200 to 10 000 is prepared in the presence of a BF₃ -amine complex as a catalyst and subsequently reacted with (c) at least one compound selected from the group consisting of aliphatic, cycloaliphatic and heterocyclic polyamine.

7. A process as claimed in claim 6 wherein the reaction product of components (a), (b) and (c) is further reacted with (d) an unsaturated compound of formula HC(R₁)═

C(R₂)--X, wherein R₁, R₂ and X are as defined above at a temperature of from 20°

to 70°

C.

8. A process as claimed in claim 6, wherein component (c) is additionally first reacted at temperatures of from 20°

to 70°

C. with (d) an unsaturated compound of formula HC(R₁)═

C(R₂)--X wherein R₁, R₂ and X are as defined above and further reacted with the adduct of components (a) and (b).

9. A process as claimed in claim 6 wherein (a) 2 to 4 equivalents of at least one polyepoxide compound and (b) 0.2 to 1.5 equivalents of at least one polyalkylene polyether polyol is reacted in a first step in the presence of a BF₃ -amine complex as catalyst at a temperature of 20°

to 200°

C. and a further reacted with component (c) at least one polyamine wherein the quantity of amine used being in 2 to 10 times excess, relative to the reacting epoxyde groups and hydrogen atoms bonded to the nitrogen at a temperature of 20°

to 100°

C.