Curable composition, article, method of curing, and tack-free reaction product

Patent metadata

Field	Value
Publication number	US-9611360-B2
Application number	US-201214003129-A
Country	US
Kind code	B2
Filing date	Mar 27, 2012
Priority date	Mar 28, 2011
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

A curable composition includes 3-substituted benzoxazine, polyepoxide, and polythiol. Articles including the curable composition, methods of curing the curable composition, and a tack-free reaction product preparable from the curable composition are also disclosed.

First claim

What is claimed is:

1. A curable composition comprising:
x equivalents of at least one 3-substituted benzoxazine, wherein x is a number greater than 0, wherein the at least one 3-substituted benzoxazine is selected from the group consisting of

and combinations thereof;
at least one polyepoxide, wherein the at least one polyepoxide contains y equivalents of glycidyl groups, wherein y is a number greater than or equal to 0; and
z equivalents of at least one polythiol selected from the group consisting of

wherein
v is 0 or 1;
t is an integer in a range of from 1 to 6, inclusive;
R 14 is a t-valent hydrocarbyl radical having from 1 to 30 carbon atoms; and
R 15 is selected from the group consisting of an alkylene group having from 1 to 30 carbon atoms, a hydroxyalkylene group having from 1 to 30 carbon atoms, an oxyalkylene group having from 1 to 30 carbon atoms, a polyoxyalkylene group having from 4 to 100 carbon atoms, and combinations thereof;
R 16 is selected from the group consisting of an alkylene group having from 1 to 30 carbon atoms, an alkyleneoxyalkylene group having from 1 to 30 carbon atoms, an alkylenepolyoxyalkylene group having from 4 to 100 carbon atoms, and combinations thereof; and

wherein z is a number greater than 0, and wherein z is in a range of from 0.1(x+y) to (x+y).

2. A curable composition according to claim 1 , wherein z is in a range of from 0.1(x+y) to 0.3(x+y).

3. A curable composition according to claim 1 , wherein y is in a range of from 0.1x to x.

4. A curable composition according to claim 1 , wherein the at least one polyepoxide comprises a polyepoxide having glycidyl groups.

5. A curable composition according to claim 1 , further comprising an acid.

6. A curable composition according to claim 5 , wherein the acid comprises a superacid.

7. A curable composition according to claim 1 , wherein the curable composition comprises a B-stage curable composition.

8. A method of curing a composition, the method comprising:
providing a curable composition comprising:
x equivalents of at least one 3-substituted benzoxazine, wherein x is a number greater than 0, wherein the at least one 3-substituted benzoxazine is selected from the group consisting of

and combinations thereof;
at least one polyepoxide, wherein the at least one polyepoxide contains y equivalents of glycidyl groups, wherein y is a number greater than or equal to 0; and

z equivalents of at least one polythiol selected from the group consisting of

wherein
v is 0 or 1;
t is an integer in a range of from 1 to 6, inclusive;
R 14 is a t-valent hydrocarbyl radical having from 1 to 30 carbon atoms; and
R 15 is selected from the group consisting of an alkylene group having from 1 to 30 carbon atoms, a hydroxyalkylene group having from 1 to 30 carbon atoms, an oxyalkylene group having from 1 to 30 carbon atoms, a polyoxyalkylene group having from 4 to 100 carbon atoms, and combinations thereof;
R 16 is selected from the group consisting of an alkylene group having from 1 to 30 carbon atoms, an alkyleneoxyalkylene group having from 1 to 30 carbon atoms, an alkylenepolyoxyalkylene group having from 4 to 100 carbon atoms, and combinations thereof; and

wherein z is a number greater than 0, and wherein z is in a range of from 0.1(x+y) to (x+y); and
curing the curable composition.

9. A method according to claim 8 , wherein z is in a range of from 0.1(x+y) to 0.3(x+y).

10. A method according to claim 8 , wherein y is in a range of from 0.1x to x.

11. A method according to claim 8 , wherein the at least one polyepoxide comprises a polyepoxide having glycidyl groups.

12. A method according to claim 8 , wherein the curable composition further comprises a superacid.

13. A tack-free reaction product of a curable composition, the curable composition comprising:
x equivalents of at least one 3-substituted benzoxazine, wherein x is a number greater than 0, wherein the at least one 3-substituted benzoxazine is selected from the group consisting of

and combinations thereof;
at least one polyepoxide, wherein the at least one polyepoxide contains y equivalents of glycidyl groups, wherein y is a number greater than or equal to 0; and
z equivalents of at least one polythiol selected from the group consisting of

wherein
v is 0 or 1;
t is an integer in a range of from 1 to 6, inclusive;
R 14 is a t-valent hydrocarbyl radical having from 1 to 30 carbon atoms; and
R 15 is selected from the group consisting of an alkylene group having from 1 to 30 carbon atoms, a hydroxyalkylene group having from 1 to 30 carbon atoms, an oxyalkylene group having from 1 to 30 carbon atoms, a polyoxyalkylene group having from 4 to 100 carbon atoms, and combinations thereof;
R 16 is selected from the group consisting of an alkylene group having from 1 to 30 carbon atoms, an alkyleneoxyalkylene group having from 1 to 30 carbon atoms, an alkylenepolyoxyalkylene group having from 4 to 100 carbon atoms, and combinations thereof; and

wherein z is a number greater than 0, and wherein z is in a range of from 0.1(x+y) to (x+y).

14. A tack-free reaction product according to claim 13 , wherein z is in a range of from 0.1(x+y) to 0.3(x+y).

15. A tack-free reaction product according to claim 13 , wherein y is in a range of from 0.1x to x.

16. A tack-free reaction product according to claim 13 , wherein the at least one polyepoxide comprises a polyepoxide having glycidyl groups.

17. A tack-free reaction product according to claim 13 , wherein the components further comprise an acid.

18. A tack-free reaction product according to claim 17 , wherein the acid comprises a superacid.

19. An article comprising a curable composition disposed on a first releasable liner, wherein the curable composition comprises:
x equivalents of at least one 3-substituted benzoxazine, wherein x is a number greater than 0, wherein the at least one 3-substituted benzoxazine is selected from the group consisting of

and combinations thereof;
at least one polyepoxide, wherein the at least one polyepoxide contains y equivalents of glycidyl groups, wherein y is a number greater than or equal to 0; and
z equivalents of at least one polythiol selected from the group consisting of

wherein
v is 0 or 1;
t is an integer in a range of from 1 to 6, inclusive;
R 14 is a t-valent hydrocarbyl radical having from 1 to 30 carbon atoms; and
R 15 is selected from the group consisting of an alkylene group having from 1 to 30 carbon atoms, a hydroxyalkylene group having from 1 to 30 carbon atoms, an oxyalkylene group having from 1 to 30

Assignees

• Gorodisher Ilya
• 3M Innovative Properties Co

Inventors

• Gorodisher Ilya

Classifications

• C08L63/00 Primary

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08L81/02

  Polythioethers; Polythioether-ethers · CPC title

• C08G75/14 Primary

  Polysulfides · CPC title

• C08G59/504 Primary

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title

• C08G77/392

  containing sulfur · CPC title