Curable composition containing silicone, and cured product thereof

Patent metadata

Field	Value
Publication number	US-9512272-B2
Application number	US-201414761763-A
Country	US
Kind code	B2
Filing date	Jan 22, 2014
Priority date	Jan 25, 2013
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

Disclosed is a curable composition including a silicone (A) of a specific structure and a composition containing Si—OH group and Si—H group, a silicone (B) of a specific structure and a composition containing Si—OH group and Si—CH═CH 2 group, and a hydrosilylation catalyst of a catalytic quantity containing at least one metal compound selected from the group consisting of platinum compounds, palladium compounds, and rhodium compounds. In this curable composition, as kind of each silicone and the content of Si—OH group are adjusted, in curing the silicone, foaming in a cured product can be inhibited by inhibiting a dehydration condensation reaction between Si—OH groups, as compared with a hydrosilylation reaction which is a reaction of Si—CH═CH 2 group and Si—H group. Furthermore, an excellent adhesion to a base body such as semiconductor substrate can be given when making a cured film.

First claim

The invention claimed is:

1. A curable composition, comprising:
(1) a silicone (A) containing Si—OH group and Si—H group,
(2) a silicone (B) containing Si—OH group and Si—CH═CH 2 group, and
(3) a hydrosilylation catalyst of a catalyst amount, containing at least one metal compound selected from the group consisting of platinum compounds, palladium compounds, and rhodium compounds,
wherein
(a): the silicone (A) is the following silicone (A-1) and/or silicone (A-2), the silicone (B) is the following silicone (B-1) and/or silicone (B-2), in case that the silicone (A) consists of the silicone (A-1), the silicone (B) comprises at least the silicone (B-2), and in case that the silicone (A) consists of the silicone (A-2), the silicone (B) comprises at least the silicone (B-1),
(b): a molar ratio of Si—H group to the Si—CH═CH 2 group in the silicone (A) and the silicone (B) which are contained in the curable composition is in a range of 4:1 to 1:1, and
(c): in the curable composition, a content of Si—OH group relative to a total amount of the curable composition is 3.4 mass % or greater and 9.8 mass % or less, a content of Si—H group is 0.1 mmol/g or greater and 5.0 mmol/g or less in molar content relative to the curable composition, and a content of Si—CH═CH 2 group is 0.1 mmol/g or greater and 5.0 mmol/g or less,
wherein (i) Silicone (A-1) is a silicone containing 10 mass % or greater of Si—OH group relative to a total amount of the silicone (A-1), which is obtained by hydrolysis and polycondensation of at least one alkoxysilane selected from the group consisting of an alkoxysilane represented by the general formula (1), (2), and (3):
R 1 R 2 Si(OR 3 ) 2 ,  (1)

R 4 Si(OR 5 ) 3 , and  (2)

Si(OR 6 ) 4 ;  (3)

 with an alkoxysilane represented by the general formula (4)
H—Si(OR 7 ) 3   (4)

 under an acid condition or a basic condition,
wherein (ii) Silicone (A-2) is a silicone containing 3.3 mass % or less of Si—OH group relative to a total amount of the silicone (A-2), which is obtained by reacting a reaction product containing Si—OH group and obtained by hydrolysis and polycondensation, under an acid condition or a basic condition, of at least one alkoxysilane selected from the group consisting of an alkoxysilane represented by the general formula (1), (2), and (3):
R 1 R 2 Si(OR 3 ) 2 ,  (1)

R 4 Si(OR 5 ) 3 , and  (2)

Si(OR 6 ) 4 ;  (3)

 with at least one silane compound containing Si—H group selected from the group comprising a silane compound containing Si—H group represented by the general formula (5-1), the general formula (5-2), the general formula (5-3), or the general formula (5-4)

 wherein (iii) silicone (B-1) is a silicone containing 10 mass % or greater of Si—OH group to a total amount of the silicone (B-1), which is obtained by hydrolysis and polycondensation of at least one alkoxysilane selected from the group consisting of an alkoxysilane represented by the general formula (1), (2), and (3):
R 1 R 2 Si(OR 3 ) 2 ,  (1)

R 4 Si(OR 5 ) 3 , and  (2)

Si(OR 6 ) 4 ;  (3)

 with an alkoxysilane represented by the general formula (6)
CH 2 ═CH—Si(OR 8 ) 3   (6)

 under an acid condition or a basic condition,
wherein (iv) Silicone (B-2) is a silicone containing 3.3 mass % or less of Si—OH group relative to a total amount of the silicone (B-2), which is obtained by reacting a reaction product containing Si—OH group and obtained by hydrolysis and polycondensation, under an acid condition or a basic condition, of at least one alkoxysilane selected from a group consisting of an alkoxysilane represented by the general formula (1), (2), and (3):
R 1 R 2 Si(OR 3 ) 2 ,  (1)

R 4 Si(OR 5 ) 3 , and  (2)

Si(OR 6 ) 4   (3)

 with at least one compound selected from the group consisting of a silane compound containing Si—CH═CH 2 group represented by the general formula (7-1), the general formula (7-2), the general formula (7-3), or the general formula (7-4)

wherein
each of R 1 and R 2 is a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group which is C 1-6 straight-chain, C 3-6 branched-chain, or C 3-6 cyclic, or an aryl group which is C 6-15 , in the alkyl group or aryl group, a part of or all of hydrogen atoms may be replaced with fluorine atom, a part of carbon atoms may be replaced with oxygen atom or nitrogen atom,
R 3 is a methyl group, an ethyl group, or an isopropyl group
R 4 is a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group which is C 1-6 straight-chain, C 3-6 branched-chain, or C 3-6 cyclic, or an aryl group which is C 6-15 , in the alkyl group or aryl group, a part of or all of hydrogens atom may be replaced with fluorine atom, a part of carbon atoms may be replaced with oxygen atom or nitrogen atom,
R 5 is a methyl group, an ethyl group, or an isopropyl group
R 6 is a methyl group, an ethyl group, or an isopropyl group
R 7 is a methyl group, an ethyl group, or an isopropyl group
each of R 1a and R 1b is independently a fluorine atom, an alkyl group which is C 1-6 straight-chain, C 3-6 branched-chain, or C 3-6 cyclic, or aryl group which is C 6- 15 , furthermore in the alkyl group or an aryl group, a part of or all of hydrogen atoms may be replaced with fluorine atom, a part of carbon atoms may be replaced with oxygen atom or nitrogen atom,
R 1c is a methyl group, an ethyl group, or an isopropyl group
R 8 is a methyl group, an ethyl group, or an isopropyl group
each of R 1d and R 1e is independently a fluorine atom, an alkyl group which is C 1-6 straight-chain, C 3-6 branched-chain, or C 3-6 cyclic, or an aryl group which is C 6-15 , in the alkyl group or aryl group, a part of or all of hydrogen atoms may be replaced with fluorine atom, a part of carbon atoms may be replaced with oxygen atom or nitrogen atom, and
R 1f is a methyl group, an ethyl group, or an isopropyl group.

2. The curable composition as claimed in claim 1 , wherein the silane compound containing Si—H group is a silane compound represented by the formula (5-5), (5-8), or (5-9).

3. The curable composition as claimed in claim 1 , wherein the silane compound containing Si—CH═CH 2 group is a silane compound represented by the formula (7-5), (7-7), or (7-8).

4. A cured product made by curing the curable composition as claimed in claim 1 .

5. A sealing material made by using the cured product as claimed in claim 4 .

6. A method for producing a cured product wherein the curable composition as claimed claim 1 is cured by heating to 70° C. or higher and 300° C. or lower.

Assignees

• Central Glass Co Ltd

Inventors

• Akiyama Katsuhiro
• Matsuno Yu
• Eguchi Hiroshi
• Yamanaka Kazuhiro
• Nakatsuji Junya
• Kawai Wataru
• Ogawa Tsuyoshi

Classifications

• H10W74/476

  Organic materials comprising silicon · CPC title

• H10H20/854

  characterised by their material, e.g. epoxy or silicone resins · CPC title

• H01L2924/0002

  Electricity · mapped topic

• C09K3/1018

  Macromolecular compounds having one or more carbon-to-silicon linkages · CPC title

• C08L83/06

  containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence) · CPC title