Organic silicon compound, surface treatment agent containing same, resin composition containing same, and gel or cured product of same

Patent metadata

Field	Value
Publication number	US-10604658-B2
Application number	US-201415757702-A
Country	US
Kind code	B2
Filing date	Aug 11, 2014
Priority date	Aug 14, 2013
Publication date	Mar 31, 2020
Grant date	Mar 31, 2020

Abstract

An organic silicon compound is disclosed which is represented by a formula: (R13SiO)3SiR2—[SiR32O]y[SiR32]w—R4—R5, wherein each of R1 and R3 is a group independently selected from the group consisting of alkyl groups, alkenyl groups, aryl groups, aralkyl groups and alkoxy groups having 1 to 20 carbon atoms, R2 is a divalent hydrocarbon group or an oxygen atom, R4 is a divalent hydrocarbon group, or a direct bond to a silicon (Si) atom, R5 is a monovalent group represented by (R6O)qR7(3-q)Si or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and each of R6 and R7 is a group independently selected from the group consisting of alkyl groups, alkenyl groups, aryl groups, aralkyl groups and alkoxy groups having 1 to 20 carbon atoms, and q is an integer between 1 and 3, y is an integer between 0 and 200, and w is 0 or 1.

First claim

The invention claimed is:

1. A resin composition comprising an organic silicon compound and a filler whose surface has been treated therewith, wherein the organic silicon compound is represented by a formula (1) below:

wherein each of R 1 and R 3 is a group selected independently from the group consisting of alkyl groups, alkenyl groups, aryl groups, aralkyl groups and alkoxy groups having 1 to 20 carbon atoms, R 2 is a divalent hydrocarbon group, which may optionally contain a hetero atom, or an oxygen atom, R 4 is a divalent hydrocarbon group, which may optionally contain a hetero atom, or a direct bond to a silicon (Si) atom, R 5 is a monovalent group represented by (R 6 O) q R 7 (3-q) Si or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and each of R 6 and R 7 is a group independently selected from the group consisting of alkyl groups, alkenyl groups, aryl groups, aralkyl groups and alkoxy groups having 1 to 20 carbon atoms, and q is an integer between 1 and 3, y is an integer between 0 and 200, and w is an integer that is 0 or 1.

2. A material comprising the resin composition according to claim 1 , wherein the material is further defined as a thermally conductive material, an electrically conductive material, a semiconductor sealing material, an optical material, a functional coating material or a cosmetic material.

3. The resin composition according to claim 1 , which exhibits thickening properties, curing properties or phase change properties.

4. A thermally conductive silicone composition comprising (A) an organic silicon compound and (B) a thermally conductive filler; wherein the organic silicon compound is represented by a formula (1) below:

wherein each of R 1 and R 3 is a group selected independently from the group consisting of alkyl groups, alkenyl groups, aryl groups, aralkyl groups and alkoxy groups having 1 to 20 carbon atoms, R 2 is a divalent hydrocarbon group, which may optionally contain a hetero atom, or an oxygen atom, R 4 is a divalent hydrocarbon group, which may optionally contain a hetero atom, or a direct bond to a silicon (Si) atom, R 5 is a monovalent group represented by (R 6 O) q R 7 (3-q) Si or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and each of R 6 and R 7 is a group independently selected from the group consisting of alkyl groups, alkenyl groups, aryl groups, aralkyl groups and alkoxy groups having 1 to 20 carbon atoms, and q is an integer between 1 and 3, y is an integer between 0 and 200, and w is an integer that is 0 or 1.

5. The thermally conductive silicone composition according to claim 4 , further comprising (C) at least one type of organopolysiloxane other than the organic silicon compound.

6. The thermally conductive silicone composition according to claim 4 , wherein the thermally conductive filler (B) is at least one type of powder and/or fiber selected from the group consisting of a pure metal, an alloy, a metal oxide, a metal hydroxide, a metal nitride, a metal carbide, a metal silicide, carbon, a soft magnetic alloy and a ferrite.

7. The thermally conductive silicone composition according to claim 6 ,
wherein the pure metal is bismuth, lead, tin, antimony, indium, cadmium, zinc, silver, copper, nickel, aluminum, iron or metallic silicon,
wherein the alloy is an alloy consisting of two or more metals selected from the group consisting of bismuth, lead, tin, antimony, indium, cadmium, zinc, silver, copper, nickel, aluminum, iron and metallic silicon,
wherein the metal oxide is alumina, zinc oxide, silicon oxide, magnesium oxide, beryllium oxide, chromium oxide or titanium oxide,
wherein the metal hydroxide is magnesium hydroxide, aluminum hydroxide, barium hydroxide or calcium hydroxide,
wherein the metal nitride is boron nitride, aluminum nitride or silicon nitride,
wherein the metal carbide is silicon carbide, boron carbide or titanium carbide,
wherein the metal silicide is magnesium silicide, titanium silicide, zirconium silicide, tantalum silicide, niobium silicide, chromium silicide, tungsten silicide or molybdenum silicide,
wherein the carbon is diamond, graphite, a fullerene, carbon nanotubes, graphene, activated carbon or monolithic carbon black,
wherein the soft magnetic alloy is an Fe—Si alloy, an Fe—Al alloy, an Fe—Si—Al alloy, an Fe—Si—Cr alloy, an Fe—Ni alloy, an Fe—Ni—Co alloy, an Fe—Ni—Mo alloy, an Fe—Co alloy, an Fe—Si—Al—Cr alloy, an Fe—Si—B alloy or an Fe—Si—Co—B alloy, and
wherein the ferrite is a Mn—Zn ferrite, a Mn—Mg—Zn ferrite, a Mg—Cu—Zn ferrite, a Ni—Zn ferrite, a Ni—Cu—Zn ferrite or a Cu—Zn ferrite.

8. The thermally conductive silicone composition according to claim 4 , wherein the thermally conductive filler (B) is (B1) a lamellar boron nitride powder having an average particle diameter of 0.1 to 30 μm, (B2) a granular boron nitride powder having an average particle diameter of 0.1 to 50 μm, (B3) a spherical and/or crushed aluminum oxide powder having an average particle diameter of 0.01 to 50 μm, (B4) a spherical and/or crushed graphite having an average particle diameter of 0.01 to 50 μm, or a mixture of two or more types thereof.

9. The thermally conductive silicone composition according to claim 5 , wherein the content of component (B) is 100 to 3,500 parts by mass relative to a total of 100 parts by mass of component (A) and component (C).

10. The thermally conductive silicone composition according to claim 5 , wherein the organopolysiloxane of component (C) has a hydrolyzable functional group bonded to a silicon atom in the molecule.

11. The thermally conductive silicone composition according to claim 5 , wherein component (C) comprises 1) an organopolysiloxane having a monovalent hydrocarbon group having an aliphatic unsaturated bond bonded to a silicon atom in the molecule, and 2) an organopolysiloxane having a hydrogen atom bonded to a silicon atom in the molecule, wherein the composition contains a catalyst which thickens or cures these organopolysiloxanes by a hydrosilylation reaction.

12. The thermally conductive silicone composition according to claim 5 , wherein component (C) comprises 1) an organopolysiloxane having a monovalent hydrocarbon group having an aliphatic unsaturated bond bonded to a silicon atom in the molecule, 2) an organopolysiloxane having a hydrogen atom bonded to a silicon atom in the molecule, and 3) an organopolysiloxane having a hydrolyzable functional group bonded to a silicon atom in the molecule, wherein the composition contains a catalyst which thickens or cures these organopolysiloxanes by a hydrosilylation reaction.

13. A gel or cured product obtained by thickening or curing the thermally conductive silicone composition according to claim 11 .

14. A gel or cured product obtained by thickening or curing the thermally conductive silicone composition according to claim 12 .

15. A method of preparing a surface treated filler, said method comprising:
treating a surface of a filler with an organo silicon compound to give the surface treated filler, wherein the organic silicon compound is represented by a formula (1) below:

wherein each of R 1 and R 3 is a group selected independently from the group consisting of alkyl groups, alkenyl groups, aryl groups, aralkyl groups and alkoxy groups having 1 to 20 carbon atoms, R 2 is a divalent hyd

Assignees

• Dow Corning Toray Co Ltd
• Dow Toray Co Ltd

Inventors

• Furukawa Haruhiko
• Iwai Makoto
• Iwakawa Kousei
• Kitaura Eiji
• Nishijima Kazuhiro
• Okawa Tadashi

Classifications

• C08K9/06

  with silicon-containing compounds · CPC title

• C08K2201/003

  Additives being defined by their diameter · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C09D183/14 Primary

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09D183/10 takes precedence) · CPC title

• C08K2201/001

  Conductive additives · CPC title