Temperature-resistant silicone resins

Patent metadata

Field	Value
Publication number	US-9932475-B2
Application number	US-201615061459-A
Country	US
Kind code	B2
Filing date	Mar 4, 2016
Priority date	Jul 11, 2014
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

Methods and formulations for modified silicone resins of Formula (I) are presented:

The R 1 , R 2 , and R 3 are each independently selected from a group consisting of H, alkyl, alkenyl, alkynyl, and aryl; n ranges from 1 to 10; m ranges from 1 to 200; and p ranges from 2 to 1,000. The elastomeric materials prepared from modified silicone resins display robust mechanical properties following prolonged exposure to high temperatures (e.g., 316° C. or higher).

First claim

What is claimed is:

1. A silicone resin of Formula (I):

wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, and aryl;
n ranges from 1 to 10;
m ranges from 1 to 200; and
p ranges from 2 to 1,000.

2. The silicone resin of claim 1 , wherein:
m ranges from 1 to 100; and
p ranges from 10 to 500.

3. The silicone resin of claim 2 , wherein:
each of R 1 , R 2 , and R 3 is independently selected from the group consisting of H, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, and aryl.

4. The silicone resin of claim 3 , wherein:
each of R 1 , R 2 , and R 3 is independently selected from the group consisting of methyl, ethyl, propyl, butyl, ethylenyl, propylenyl, butylenyl, acetylenyl, diacetylenyl, and aryl.

5. The silicone resin of claim 4 , wherein:
each of R 1 , R 2 , and R 3 is independently selected from the group consisting of methyl and phenyl.

6. The silicone resin of claim 5 , wherein the silicone resin is selected from the group consisting of:

and wherein;
n ranges from 1 to 10;
m ranges from 5 to 100; and
p ranges from 10 to 500.

7. The silicone resin of claim 1 , wherein the ratio of n to m is between about 1:1 to about 1:2000.

8. The silicone resin of claim 7 , wherein the ratio of n to m is between about 1:4 and about 1:200.

9. A formulation comprising the silicone resin of claim 1 and a curing agent.

10. A formulation comprising:
at least one silicone resin of Formula (I):

wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, and aryl;
n ranges from 1 to 10;
m ranges from 1 to 200; and
p ranges from 2 to 1,000; and

at least one metal oxide.

11. The formulation of claim 10 , further comprising at least one curing agent selected from the group consisting of dibutyltin dilaurate, tris(dimethylamino)methylsilane, and ethyltriacetoxysilane.

12. The formulation of claim 11 , wherein the curing agent is dibutyltin dilaurate.

13. The formulation of claim 10 , wherein:
n ranges from 1 to 3;
m ranges from 1 to 100; and
p ranges from 10 to 500.

14. The formulation of claim 10 , wherein:
each of R 1 , R 2 , and R 3 is independently selected from the group consisting of H, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, and aryl.

15. The formulation of claim 14 , wherein:
each of R 1 , R 2 , and R 3 is independently selected from the group consisting of methyl, ethyl, propyl, butyl, ethylenyl, propylenyl, butylenyl, acetylenyl, diacetylenyl, and aryl.

16. The formulation of claim 15 , wherein:
each of R 1 , R 2 , and R 3 is independently selected from the group consisting of methyl and phenyl.

17. The formulation of claim 16 , wherein: the at least one silicone resin comprises at least one of the following:

and wherein:
n ranges from 1 to 10;
m ranges from 5 to 100; and
p ranges from 10 to 500.

18. The formulation of claim 10 , wherein the at least one metal oxide is selected from the group consisting of FeO, Fe 2 O 3 , Fe 3 O 4 , TiO 2 , CeO 2 , ZnO, ZrO 2 and TiO 2 .

19. The formulation of claim 10 , wherein the at least one metal oxide has a particle diameter size ranging from about 1 nm to about 5 μm.

20. The formulation of claim 19 , wherein the at least one metal oxide has a particle diameter size from about 25 nm to about 2 μm.

21. The formulation of claim 20 , wherein the at least one metal oxide has a particle diameter size from about 50 nm to about 500 nm.

22. The formulation of claim 10 , wherein values for n, m and p provide a resin of Formula (I) having a viscosity ranging from about 500 cSt to about 10,000 cSt.

23. The formulation of claim 10 , wherein a ratio of n to m ranges from about 1:1 to about 1:200.

24. The formulation of claim 10 , further comprising:
at least one silicone resin of Formula (II):

wherein each of R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, and aryl;
X is selected from the group consisting of arylene, transition metal, inorganic oxide, and silsesquioxane;
t ranges from 1 to 10;
y ranges from 1 to 200; and
z ranges from 1 to 1,000.

25. The silicone resin of claim 24 , wherein:
t ranges from 1 to 3;
y ranges from 1 to 100; and
z ranges from 10 to 500.

26. The formulation of claim 24 , wherein:
each of R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently selected from the group consisting of H, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, and aryl.

27. The formulation of claim 26 , wherein:
each of R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently selected from the group consisting of methyl, ethyl, propyl, butyl, ethylenyl, propylenyl, butylenyl, acetylenyl, diacetylenyl, and aryl.

28. The formulation of claim 27 , wherein:
each of R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently selected from the group consisting of methyl and phenyl.

29. The formulation of claim 10 , further comprising at least one silicate.

30. The formulation of claim 29 , wherein the at least one silicate comprises at least one of ethyl silicate, methyl silicate, isopropyl silicate and butyl silicate.

31. The formulation of claim 10 , further comprising:
at least one silicate; and
at least one silica.

32. The formulation of claim 31 , wherein:
the at least one silicate comprises at least one of ethyl silicate, methyl silicate, isopropyl silicate and butyl silicate; and
wherein the at least one silica comprises at least one of fumed silica and functionalized silica.

33. The formulation of claim 32 , wherein:
the metal oxide is Fe 2 O 3 having a particle size ranging from about 0.5 μm to about 5 μm.

34. The formulation of claim 24 , wherein X is arylene and a ratio of arylene units to siloxane units of formula (II) is between about 1:5 and about 1:200.

35. A formulation comprising:
at least one silicone resin having a tensile strength of between about 3.6 MPa and about 6.8 MPa at room temperature and represented by Formula (I):

wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, and aryl;
n ranges from 1 to 10;
m ranges from 1 to 200; and
p ranges from 2 to 1,000; and

at least one metal oxide.

36. An elastomer that is the reaction product of:
a siloxane of formula:

Assignees

• Boeing Co

Inventors

• Zhou Chaoyin
• Nowak Andrew P
• Sharp Richard E
• Li Wen
• French James E

Classifications

• C08K2003/2265

  of iron · CPC title

• C08K3/22

  of metals · CPC title

• C08G77/80

  Siloxanes having aromatic substituents, e.g. phenyl side groups · CPC title

• C08K3/36

  Silica · CPC title

• C08G77/395

  containing phosphorus · CPC title