IP Library Granted Patent US 9,255,186
Granted Patent B2
US 9,255,186 · App. 14/667,743 · Granted Feb 9, 2016

Thermosetting resins with enhanced cure characteristics containing organofunctional silane moieties

Inventors: Vandana Vij (Palmdale, CA); Andrew Guenthner (Lancaster, CA); Timothy S. Haddad (Lancaster, CA); Joseph M. Mabry (Lancaster, CA)
Assignee: The United States of America as represented by the Secretary of the Air Force
C08G77/80C07F7/0818C07F7/10C07F7/0809C08F230/08C08L43/04
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Quick Facts
Patent No.
US 9,255,186
App. No.
14/667,743
Granted
Feb 9, 2016
Kind
B2
Abstract

A thermosetting resin. The resin includes a silane and a co-reactant monomer. The silane includes a quaternary silicon atom with first and second non-hydrolyzable moieties chemically bonded thereto. Each of the first and second non-hydrolyzable moieties includes respective first and second reactive groups. The reactive groups include at least one aromatic or unsaturated group having a triple bond.

Claims (43)

1. A thermosetting resin comprising:

a silane comprising:

a quaternary silicon atom;

a first non-hydrolyzable moiety bonded to the quaternary silicon atom and including a first reactive group;

a second non-hydrolyzable moiety bonded to the quaternary silicon atom and including a second reactive group;

a third non-hydrolyzable moiety bonded to the quaternary silicon atom and including a third reactive group; and

a fourth non-hydrolyzable moiety bonded to the quaternary silicon atom,

wherein each of the first, second, and third reactive groups includes at least one triple bond and is selected from the group consisting of a cyanate ester and a phthalonitrile; and

a co-reactant monomer configured to react and form a three dimensional network with the silane.

2. The thermosetting resin of claim 1 , wherein the

fourth non-hydrolyzable moiety is chemically inert.

3. The thermosetting resin of claim 1 , wherein the silane further comprises:

at least one linking group between the quaternary silicon atom and one or more of the first non-hydrolyzable moiety, the second non-hydrolyzable moiety, and the third non-hydrolyzed moiety.

4. The thermosetting resin of claim 1 , wherein the co-reactant monomer includes an epoxy monomer.

5. The thermosetting resin of claim 1 , wherein the

fourth non-hydrolyzable moiety is an aromatic or an unsaturated group having a triple bond.

6. A method comprising:

curing non-hydrolyzable silanes to form a resin, each non-hydrolyzable silane comprising:

a quaternary silicon atom;

a first terminal group chemically bonded to the quaternary silicon atom;

a second terminal group chemically bonded to the quaternary silicon atom;

a third terminal group chemically bonded to the quaternary silicon atom; and

a fourth terminal group chemically bonded to the quaternary silicon atom, the fourth terminal group being nonhydrolyzable,

wherein each of the first, second, and third terminal groups is non-hydrolyzable and includes at least one reactive group having a triple bond and is selected from the group consisting of a cyanate ester and a phthalonitrile,

wherein the reactive groups of the first, second, and third terminal groups form more than 3 mmoles of network junctions per cubic centimeter volume within the resin.

7. The method of claim 6 , further comprising:

introducing one or more additives while curing the non-hydrolyzable silanes, the one or more additives configured to impart a mechanical characteristic, a thermal characteristic, a moisture-resistant characteristic, an electrical characteristic, or two or more thereof to the resin.

8. A thermosetting resin comprising:

a plurality of non-hydrolyzable silanes, each non-hydrolyzable silane of the plurality comprising:

a quaternary silicon atom; and

four non-hydrolyzable terminal groups chemically bonded to the quaternary silicon atom, at least three of the four non-hydrolyzable terminal groups having a reactive group including at least one triple bond and is selected from the group consisting of a cyanate ester and a phthalonitrile,

wherein the cured resin includes more than 3 mmoles of network junctions per cubic centimeter volume.

9. The thermosetting resin of claim 8 , wherein the one non-hydrolyzable terminal group without the reactive group is chemically inert.

10. The thermosetting resin of claim 1 , further comprising:

at least one linking group between the quaternary silicon atom and the fourth non-hydrolyzable moiety.

11. The thermosetting resin of claim 3 , wherein the at least one linking group comprises dimethylsiloxy or methylene.

12. The thermosetting resin of claim 1 , wherein the silane has a chemical name of tetrakis(4-cyanatophenyl)silane.

13. The thermosetting resin of claim 5 , wherein the fourth non-hydrolyzable moiety is selected from a group consisting of methyl, phenyl, napthyl, trimethylsilyl, trimethylsiloxy, and trifluoromethyl.

14. The thermosetting resin of claim 10 , wherein the at least one linking group comprises dimethylsiloxy or methylene.

15. The thermosetting resin of claim 13 , wherein the fourth non-hydrolyzable moiety is methyl, and wherein the silane has a chemical name of tris(4-cyanatophenyl)methylsilane.

16. The thermosetting resin of claim 8 , further comprising:

at least one linking group between the quaternary silicon atom and at least one of the four non-hydrolyzable terminal groups.

17. The thermosetting resin of claim 16 , wherein the at least one linking group comprises dimethylsiloxy or methylene.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2015
From: VIJ, VANDANA; MABRY, JOSEPH; GUENTHNER, ANDREW; HADDAD, TIMOTHY; ERC, INCORPORATED
To: GOVERNMENT OF THE UNITED STATES AS REPRESENTED BY THE SECRETARY OF THE AIR FORCE
Reel/Frame 035247/0838 →
Continuity (2)
Division 13748730 · Jan 24, 2013
Related Publication 20150197606A1 · Jul 16, 2015