# US 9,752,007 B2 · Thermally conductive condensation reaction curable polyorganosiloxane composition and methods for the preparation and use of the composition

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- Number: US 9,752,007 B2
- Document ID: US9752007B2
- Status: Granted
- Kind: B2
- Application number: 14/418,464
- Filed: 2013-05-31
- Published: 2015-07-02
- Granted: 2017-09-05
- Earliest claimed: 2012-07-30
- Assignees: Dow Corning Corporation
- Applicants: Dow Corning Corporation
- Inventors: Dorab Edul Bhagwagar; Jeffrey Krzywosinski; Kai Su
- Web page: https://patentgrep.com/patent/US9752007B2

## CPC

- C08K 3/22: of metals
- C08L 83/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08L83/10 takes precedence)
- C09J 183/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09J183/10 takes precedence)
- C08G 77/14: containing silicon bound to oxygen-containing groups
- C08G 77/50: by carbon linkages
- C08K 2003/2227: {of aluminium}
- C08K 2201/001: Conductive additives
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A composition comprises (A) a condensation reaction catalyst, (B) a polyorganosiloxane having an average, per molecule, of at least two hydrolyzable substituents, (C) a crosslinker, and (D) a thermally conductive filler. The polyorganosiloxane may be silanol terminated, and the crosslinker may be an alkoxysilylhydrocarbylene functional polyorganosiloxane. The composition is capable of reacting via condensation reaction to form a thermally conductive product. The composition and product are useful for thermal management in (opto)electronics applications.

## Claims

### Claim 1

A curable composition comprising:
(A) a condensation reaction catalyst,
(B) a polyorganosiloxane having an average, per molecule, of at least two hydrolyzable substituents,
(C) a crosslinker having formula (R12R2SiO1/2)f(R1R2SiO2/2)g(R2SiO3/2)h(R13SiO1/2)i(R12SiO2/2)j(R1SiO3/2)k(SiO4/2)l, where
each R1 is independently a monovalent organic group,
each R2 has formula
where each D is independently a divalent organic group, each R is independently a monovalent hydrocarbon group, each X is independently a hydrolyzable substituent, subscript a is 0, 1, or 2, subscript b≧0, subscript c is 0, 1, 2, or 3, with the proviso that a quantity (a+c)≧1; and subscript d≧1, subscript e is 0 or 1, subscript f≧0, subscript g≧0, subscript h≧0, with the proviso that a quantity (f+g+h)≧2, subscript i≧0, subscript j≧0, subscript k≧0, subscript l≧0, with the proviso that a quantity (g+j)≧2, and with the proviso that when a quantity (a+c)=1, then a quantity (f+g+h)≧3, and
(D) a thermally conductive filler, where ingredient (D) is present in an amount of from 30% to 80% by volume of the curable composition.

### Claim 2 (depends on 1)

The curable composition of claim 1, where at least one of the following conditions is satisfied:
(i) ingredient (A) comprises an organotin compound, or
(ii) ingredient (A) comprises a dimethyltin compound.

### Claim 3 (depends on 1)

The curable composition of claim 1, where at least one of the following conditions is satisfied:
(i) ingredient (B) comprises a silanol-functional polyorganosiloxane; or
(ii) ingredient (B) comprises a silanol-terminated polydiorganosiloxane of formula R4R32SiO—(R32SiO)p—SiR32R4, where
each R3 is independently a monovalent hydrocarbon group or a monovalent halogenated hydrocarbon group,
each R4 is a hydrolyzable substituent, and
subscript p has an average value of 50 to 200,000; or
(iii) ingredient (B) comprises a silanol-terminated polydimethylsiloxane.

### Claim 4 (depends on 1)

The curable composition of claim 1, where at least one of the following conditions is satisfied:
(i) ingredient (C) comprises a crosslinker of formula (i)
where each D is independently a divalent hydrocarbon group, each X is independently a hydrolyzable substituent, each subscript a is independently 0, 1, or 2, each subscript b≧0, each subscript c is independently 0, 1, 2, or 3, each subscript d≧1, each subscript e is independently is 0 or 1, with the proviso that subscripts a, b, and c are selected such that the crosslinker has an average, per molecule, of at least three X, and subscript m has an average value of at least 100; or
(ii) ingredient (C) comprises a crosslinker of formula (ii)
where each D is independently an alkylene group, each X is independently an alkoxy group, each subscript b≧0, each subscript 2≧d≧1, and subscript m has an average value of 150 to 500; or
(iii) ingredient (C) comprises an alkoxysilylhydrocarbylene functional polyorganosiloxane.

### Claim 5 (depends on 1)

The curable composition of claim 1, where the curable composition further comprises at least one additional ingredient selected from (E) a spacer, (F) a pigment, (G) a treating agent, (H) an adhesion promoter, or (J) a drying agent.

### Claim 6

A method comprising (i) mixing ingredients comprising:
(A) a condensation reaction catalyst,
(B) a polyorganosiloxane having an average, per molecule, of at least two hydrolyzable substituents,
(C) a crosslinker having unit formula (R12R2SiO1/2)f(R1R2SiO2/2)g(R2SiO3/2)h(R13SiO1/2)i(R12SiO2/2)j(R1SiO3/2)k(SiO4/2)l, where
each R1 is independently a monovalent organic group,
each R2 has formula
where each D is independently a divalent organic group, each R is independently a monovalent hydrocarbon group, each X is independently a hydrolyzable substituent, subscript a is 0, 1, or 2, subscript b≧0, subscript c is 0, 1, 2, or 3, with the proviso that a quantity (a+c)≧1; subscript d≧1, subscript e is 0 or 1, subscript f≧0, subscript g≧0, subscript h≧0, with the proviso that a quantity (f+g+h)≧2, subscript i≧0, subscript j≧0, subscript k≧0, subscript l≧0, with the proviso that a quantity (g+j)≧2, and with the proviso that when a quantity (a+c)=1, then a quantity (f+g+h)≧3, and
(D) a thermally conductive filler;
thereby preparing a curable composition; where ingredient (D) is present in an amount of from 30% to 80% by volume of the curable composition.

### Claim 7 (depends on 6)

The method of claim 6, where the method further comprises adding to the curable composition at least one additional ingredient selected from (E) a spacer, (F) a pigment, (G) a treating agent, (H) an adhesion promoter, or (J) a drying agent.

### Claim 8 (depends on 6)

The method of claim 6, further comprising: (ii) contacting the curable composition with water.

### Claim 9 (depends on 8)

A thermally conductive reaction product prepared by the method of claim 8.

### Claim 10 (depends on 1)

The curable composition of claim 1, where ingredient (D) comprises alumina.

### Claim 11 (depends on 2)

The curable composition of claim 2, where condition (ii) is satisfied: ingredient (A) comprises a dimethyltin compound.

### Claim 12 (depends on 4)

The curable composition of claim 4, where condition (ii) is satisfied: ingredient (C) comprises a crosslinker of formula (ii)
where each D is independently an alkylene group, each X is independently an alkoxy group, each subscript b≧0, each subscript 2≧d≧1, and subscript m has an average value of 150 to 500.

### Claim 13 (depends on 5)

The curable composition of claim 5, where the curable composition further comprises (H) the adhesion promoter.

### Claim 14 (depends on 6)

The method of claim 6, where ingredient (D) comprises alumina.

### Claim 15 (depends on 7)

The method of claim 7, further comprising: (ii) contacting the curable composition with water.

### Claim 16 (depends on 15)

A thermally conductive reaction product prepared by the method of claim 15.

### Claim 17 (depends on 5)

The curable composition of claim 5, where the curable composition is stored under substantially anhydrous conditions, alternatively is stored in a sealed container.

### Claim 18 (depends on 6)

The method of claim 6, further comprising: (i-b) sealing the curable composition in a container to prevent exposure to moisture.