Degradable silyl-containing thermosetting networks

Patent metadata

Field	Value
Publication number	US-11634534-B2
Application number	US-202016917179-A
Country	US
Kind code	B2
Filing date	Jun 30, 2020
Priority date	Dec 15, 2016
Publication date	Apr 25, 2023
Grant date	Apr 25, 2023

Abstract

A process of: providing a polyfunctional compound selected from polyisocyanate, polyacrylate, and polyepoxy; and reacting the polyfunctional compound with a hydroxyl- or amine-terminated silyl-containing compound. The polyfunctional compound and the silyl-containing compound are at least difunctional. A thermoset made by this process.

First claim

What is claimed is:

1. A method comprising:
providing a thermoset made by a process comprising:
providing a polyfunctional compound selected from polyisocyanate, polyacrylate, and polyepoxy; and
reacting the polyfunctional compound with a hydroxyl- or amine-terminated silyl-containing compound;
wherein the polyfunctional compound and the silyl-containing compound are at least difunctional; and

reacting the thermoset with a fluoride salt, an acid, or a base to cleave the silicon-carbon bonds in the thermoset.

2. The method of claim 1 , wherein the polyfunctional compound is a polyisocyanate.

3. The method of claim 2 , wherein the polyisocyanate is aliphatic, aromatic, cycloaliphatic, an isocyanate homopolymer, or an isocyanate-functional pre-polymer.

4. The method of claim 2 , wherein the polyisocyanate is an aliphatic trimer based on hexamethylene diisocyanate.

5. The method of claim 1 , wherein the polyfunctional compound is an epoxy-functional dimethylpolysiloxane, an epoxy-functional polydimethyldiphenylsiloxane, an aliphatic epoxy, an aromatic epoxy, a cycloaliphatic epoxy, an acrylate-functional dimethylpolysiloxane, or 1,6-hexanedioldiacrylate.

6. The method of claim 1 , wherein the silyl-containing compound has the formula
SiR 1 n [R 3 —(O—CO—X—R 3 ) m —X′] 4−n ;

wherein each X is independently selected from —O— and —NR 2 —;
wherein each X′ is independently selected from —OH and —NHR 2 ;
wherein each R 1 is independently selected from alkyl groups and aryl groups;
wherein each R 2 is independently selected from —H, alkyl groups, and aryl groups;
wherein each R 3 is an independently selected alkylene group;
wherein n is 0, 1, or 2; and
wherein each m is an independently selected non-negative integer.

7. The method of claim 6 , wherein the silyl-containing compound has the formula
SiR 1 n [(CH 2 ) 2 OH] 4−n .

8. The method of claim 6 , wherein the silyl-containing compound is
Si(CH 3 ) 2 (CH 2 CH 2 OH) 2 ,Si(Ph) 2 (CH 2 CH 2 OH) 2 ,SiPh(CH 2 CH 2 OH) 3 ,Si(CH 2 CH 2 OH) 4 ,Si(Ph) 2 (CH 2 CH 2 OCON(CH 3 )CH 2 CH 2 OH) 2 .

9. The method of claim 6 , wherein each R 3 group is ethylene, propylene, or butylene.

10. The method of claim 1 , wherein the polyfunctional compound is reacted with a hydroxyl-functional or amine-functional material with at least one hydroxyl or amine group.

11. The method of claim 1 , wherein the thermoset comprises at least 5 wt. % of the silyl-containing compound.

12. The method of claim 1 , wherein the reaction is performed with a catalyst, a solvent, a pigment, or an additive.

13. The method of claim 1 , wherein the fluoride salt is tetrabutylammonium fluoride, stannous fluoride, potassium fluoride, or sodium fluoride.

14. The method of claim 13 , wherein the acid is a Lewis acid or Bronsted acid.

15. The method of claim 13 , wherein the base is a Lewis base or Bronsted base.

Assignees

• Us Gov Sec Navy

Inventors

• Iezzi Erick B
• Camerino Eugene
• Daniels Grant
• Wynne James H

Classifications

• C08G77/60

  in which all the silicon atoms are connected by linkages other than oxygen atoms · CPC title

• C08G18/82 Primary

  Post-polymerisation treatment · CPC title

• C08G18/3893 Primary

  containing silicon · CPC title

• C08G59/14

  Polycondensates modified by chemical after-treatment · CPC title

• C08G77/62

  Nitrogen atoms · CPC title