Tin catalysts for hydrolysis of latent amine curing agents

• US 5,206,200 A
• Filed: 04/22/1991
• Issued: 04/27/1993
• Est. Priority Date: 04/22/1991
• Status: Expired due to Fees

• Current Assignee: University Of Southern Mississippi Research Foundation
• Original Assignee: W R Grace & Company - CONN (WR Grace & Company)
• Inventors: Carney, Euegene E., Bush, Richard W.
• Primary Examiner(s): Garvin, Patrick P.
• Assistant Examiner(s): PEEBLES, BRENT
• Application Number:
  US07/689,385
• Time in Patent Office: 736 Days
• Field of Search: 502/167, 502/170
• US Class Current: 502/167
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/244 tin salts of carboxylic acids
• CPC Class Codes: C08G 18/3253 being in latent form
• CPC Class Codes: C08G 18/3256 Reaction products of polyamines with aldehydes or ketones
• CPC Class Codes: C08G 59/4014 Nitrogen containing compounds
• CPC Class Codes: C08G 59/685 Carboxylates
• CPC Class Codes: C08G 59/70 Chelates

Abstract

A tin catalyst constituting an organotin compound modified with an amine is used to catalyze the hydrolysis of latent amine curing agents in amine-curable polymeric compositions. The tin catalyst is formed from the reaction product of a stannous alkanoate and an amine, optionally in the form of an adduct with water. A preferred catalyst is the reaction product of stannous octoate and ethylenediamine.

Claims

1. A composition comprising a latent amine curing agent and a catalyst for the moisture-induced hydrolysis of the agent, said catalyst comprising an amine-modified organotin compound formed from the reaction of a stannous alkanoate having from 2 to 20 carbon atoms and an amine-containing compound.

2. A composition according to claim 1, wherein the ratio of moles of stannous alkanoate to equivalents of amino groups in the amine-containing compound is from about 1:

8 to about 8;

1.

3. A composition according to claim 1, wherein the stannous alkanoate is stannous octoate.

4. A composition according to claim 1, wherein the amine-containing compound is a mono- or polyfunctional amine selected from the group consisting of ethylenediamine, triethylenetetraamine, diethylenetriamene, epoxy adducts of triethylenetetraamine, epoxy adducts of ethylenediamine, epoxy adducts of diethylenetriamine, 1,3-diaminopropane, 1,4-diaminobutane, hexanediamine, 4,9-dioxadodecane-1,12-diamine, 4,4'"'"'-diaminodicyclohexylmethane, 9-aminomethylstearylamine, polybutandiene diamine, m-phenylenediamine, tris(aminoethyl)amine, 2-methylpentamethylenediamine, bisaminopropylpiperazine, diethylenetriamine, 3-(diethylamino)propylamine, piperazine, butylamine, dimethylaminoethanol, dodecylamine, triethylamine, amineterminated polybutadiene, and mixtures thereof.

5. A composition according to claim 4, wherein the amine is ethylenediamine.

6. A composition according to claim 1, wherein the latent amine curing agent is a ketimine.

7. A composition according to claim 1, wherein the latent amine curing agent is an aldimine.

8. A composition according to claim 1, wherein the latent amine curing agent is an enamine.

9. A composition according to claim 1, wherein the latent amine curing agent is an oxazolidine.