Room temperature curable siloxane-based gels

Patent metadata

Field	Value
Publication number	US-10294333-B2
Application number	US-201314650608-A
Country	US
Kind code	B2
Filing date	Dec 4, 2013
Priority date	Dec 12, 2012
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

Siloxane-based gel compositions are prepared from room temperature condensation curable mixtures that include 0.5-45% by weight silicone resin with at least two hydroxyl groups, 99.5-55% by weight of at least one silanol-terminated siloxane fluid, and a co-curable compound with an amino group. The siloxane-based gel compositions can be used as adhesives or sealants in medical articles.

First claim

What is claimed is:

1. A gel composition comprising the reaction product of a condensation curable mixture comprising:
at least 0.5 to less than 45% by weight silicone resin comprising at least two hydroxyl groups;
at least 55 to less than 99.5% by weight of at least one silanol-terminated siloxane fluid; and
a co-curable compound comprising an amino group, wherein the condensation curable mixture is curable at room temperature and wherein the condensation curable mixture upon curing is a gel selected from a medical gel adhesive or a medical gel sealant, wherein the gel comprises a crosslinked matrix containing a liquid or fluid.

2. The gel composition of claim 1 , wherein the co-curable compound comprising an amino group has the general structure:
R 6 2-x R 7 x N-G-Si(OR 8 ) y R 9 3-y
wherein each R 6 and R 7 independently comprises a hydrogen atom or an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group;
x is an integer of 0, 1, or 2;
G is a divalent linking group;
each R 8 independently is an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group;
each R 9 independently is an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group; and
y is an integer of 1, 2, or 3.

3. The gel composition of claim 2 , wherein G is a divalent alkylene group having the general structure:
(—CH 2 -) a

wherein a is an integer of 1 to 18.

4. The gel composition of claim 1 , further comprising at least one non-reactive siloxane fluid.

5. The gel composition of claim 1 , wherein the gel composition comprises a medical gel sealant.

6. The gel composition of claim 1 , wherein the gel composition comprises a medical gel adhesive layer.

7. The gel composition of claim 1 , wherein the gel composition comprises at least 0.5% by weight of extractable siloxane fluid.

8. An article comprising:
a substrate; and
a layer of adhesive gel disposed on at least a portion of at least one major surface of the substrate, the adhesive gel comprising the reaction product of a condensation curable mixture comprising:
at least 0.5 to less than 45% by weight silicone resin comprising at least two hydroxyl groups;
at least 55 to less than 99.5% by weight of at least one silanol-terminated siloxane fluid; and
a co-curable compound comprising an amino group, wherein the condensation curable mixture is curable at room temperature, and wherein the gel comprises a crosslinked matrix and a liquid or fluid.

9. The article of claim 8 , wherein the co-curable compound comprising an amino group has the general structure:
R 6 2-x R 7 x N-G-Si(OR 8 ) y R 9 3-y
wherein each R 6 and R 7 independently comprises a hydrogen atom or an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group;
x is an integer of 0, 1, or 2;
G is a divalent linking group;
each R 8 independently is an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group;
each R 9 independently is an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group; and
y is an integer of 1, 2, or 3.

10. The article of claim 9 , wherein G is a divalent alkylene group having the general structure:
(—CH 2 —) a

wherein a is an integer of 1 to 18.

11. The article of claim 8 , wherein the adhesive gel further comprises at least one non-reactive siloxane fluid.

12. The article of claim 8 , wherein the substrate comprises a release liner or a medical substrate.

13. The article of claim 8 , wherein the reaction product of the condensation curable mixture has been exposed to ultra-violet radiation, gamma radiation, or an electron beam.

14. A method of preparing a medical article comprising:
providing a condensation curable gel precursor composition comprising:
at least 0.5 to less than 45% by weight silicone resin comprising at least two hydroxyl groups;
at least 55 to less than 99.5% by weight of at least one silanol-terminated siloxane fluid; and
a co-curable compound comprising an amino group, wherein the condensation curable gel precursor composition is curable at room temperature;

applying the condensation curable gel precursor composition to a substrate; and
permitting the condensation curable gel precursor composition to cure at room temperature to form a gel.

15. The method of claim 14 , wherein providing the condensation curable gel precursor composition comprises mixing together of a 2 part mixture, the 2 part mixture comprising:
1) the at least 0.5 to less than 45% by weight silicone resin comprising at least two hydroxyl groups the; at least 55 to less than 99.5% by weight of at least one silanol-terminated siloxane fluid; and
2) the co-curable compound comprising an amino group, wherein 1) and 2) are physically isolated from each other prior to mixing.

16. The method of claim 15 , wherein the gel comprises a sealant.

17. The method of claim 14 , wherein the gel comprises an adhesive.

18. The method of claim 17 , wherein the substrate comprises a release liner or a medical substrate.

19. The method of claim 18 , wherein the substrate comprises a release liner, and the method further comprises laminating the gel to a second substrate or to a surface.

20. The method of claim 14 , wherein the co-curable compound comprising an amino group has the general structure:
R 6 2-x R 7 x N-G-Si(OR 8 ) y R 9 3-y
wherein each R 6 and R 7 independently comprises a hydrogen atom or an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group;
x is an integer of 0, 1, or 2;
G is a divalent linking group;
each R 8 independently is an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group;
each R 9 independently is an alkyl, aryl, heteroalkyl, heteroaryl, or aralkyl group; and
y is an integer of 1, 2, or 3.

21. The method of claim 14 , wherein the gel further comprises at least one non-reactive siloxane fluid.

22. The method of claim 14 , further comprising exposing the condensation curable gel precursor composition to ultra-violet radiation, gamma radiation, or an electron beam.

Assignees

• 3M Innovative Properties Co

Inventors

• Liu Junkang J
• Ishiwatari Hironobu
• Welke Siegfried K
• Kakinuma Yoshiteru

Classifications

• C08K5/544 Primary

  containing nitrogen · CPC title

• C08G77/44 Primary

  containing only polysiloxane sequences · CPC title

• C09J183/04

  Polysiloxanes · CPC title

• C08G77/16

  to hydroxy groups · CPC title

• C09J7/40

  characterised by release liners · CPC title