Method for producing an aminimide

Patent metadata

Field	Value
Publication number	US-10351661-B2
Application number	US-201514964748-A
Country	US
Kind code	B2
Filing date	Dec 10, 2015
Priority date	Dec 10, 2015
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

Disclosed herein are methods of preparing an aminimide. An epoxy compound is reacted with a hydrazine compound comprising a trivalent nitrogen, and an anhydride functional material or a cyclic compound containing a carbonyl group and at least one heteroatom alpha to the carbonyl group at a temperature greater than 20° C. to form the aminimide. At least one of the epoxy compound and the anhydride functional material or the cyclic compound is polymeric.

First claim

We claim:

1. A method of preparing an aminimide comprising:
reacting an (a) epoxy compound, a (b) hydrazine compound comprising a trivalent nitrogen, and a (d) cyclic compound containing a carbonyl group and at least one heteroatom of nitrogen or sulfur alpha to the carbonyl group, or a first heteroatom alpha to the carbonyl group that is oxygen and a second heteroatom alpha to the carbonyl group that is oxygen, nitrogen or sulfur, at a temperature greater than 20° C. to form the aminimide, wherein at least one of the (a) epoxy compound and the (d) cyclic compound is polymeric, wherein the aminimide comprises an aminimide functional group and at least one additional functional group selected from the group consisting of an acid functional group, a hydroxyl functional group, an amine functional group, a mercapto functional group and combinations thereof.

2. The method of claim 1 , wherein the (b) hydrazine compound comprises 1-amino-piperidine, 1,1-dimethylhydrazine, 1-amino pyrrolidine, or a combination thereof.

3. The method of claim 1 , wherein the (d) cyclic compound has the formula (I):

wherein R 1 is O, R 2 is O, S, or N, n=0 or 1, m=1-3, X=H or (CH 2 ) p CH 3 , and p=0-15.

4. The method of claim 1 , wherein the (d) cyclic compound comprises, caprolactam, ethylene carbonate, propylene carbonate, butylene carbonate, or combinations thereof.

5. The method of claim 1 , wherein a molar ratio of the (a) epoxy compound to the (b) hydrazine compound is from 1:0.5 to 0.5:1.

6. The method of claim 1 , wherein a molar ratio of the (d) cyclic compound to the (b) hydrazine compound is from 1:0.7 to 0.7:1.

7. The method of claim 1 , wherein the (a) epoxy compound, the (b) hydrazine compound, and the (d) cyclic compound are reacted in a (e) diluent.

8. The method of claim 1 , wherein the aminimide comprises an acid functional group.

9. The method of claim 1 , further comprising separating a solid from a liquid phase.

10. An aminimide prepared according to the method of claim 1 .

Assignees

• Ppg Ind Ohio Inc

Inventors

• Zhou Hongying
• Nakajima Masayuki
• Swarup Shanti
• Chao Tien-Chieh

Classifications

• C08G59/1477 Primary

  containing nitrogen · CPC title

• C08G59/1455

  Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof · CPC title

• C08F210/14

  Monomers containing five or more carbon atoms · CPC title

• C08F222/06

  Maleic anhydride · CPC title