IP Library Granted Patent US 10,308,750
Granted Patent B2
US 10,308,750 · App. 15/122,308 · Granted Jun 4, 2019

Polymerizable composition containing reactive silsesquioxane compound

Inventors: Kentaro Ohmori (Funabashi, JP); Takehiro Nagasawa (Funabashi, JP)
Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
C08F290/068C08F220/30C08F230/08C08G77/20C08L83/04C08L83/10G02B1/041C08G77/442
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Quick Facts
Patent No.
US 10,308,750
App. No.
15/122,308
Granted
Jun 4, 2019
Kind
B2
Abstract

A polymerizable composition that is suitable to produce a molded product that can suppress cracking and dimensional change caused by a high-temperature heat history with a high refractive index of a cured product maintained. A polymerizable composition including (a) 100 parts by mass of the specific reactive silsesquioxane compound, (b) 10 to 500 parts by mass of the specific fluorene compound, a cured product obtained by the polymerizable composition and a material for a high-refractive index resin lens including the polymerizable composition.

Claims (45)

1. A polymerizable composition comprising

a chain transfer agent in an amount of from 0.01 to 20 parts by mass, relative to a total amount of 100 parts by mass of polymerizable components in the polymerizable composition, the polymerizable components including:

(a) 100 parts by mass of reactive silsesquioxane compound obtained by polycondensation of an alkoxy silicon compound A of Formula [1] with an alkoxy silicon compound B of Formula [2] in the presence of an acid or a base, and

(b) 10 to 500 parts by mass of a fluorene compound of Formula [3], where the Formulae [1], [2] and [3] are as follows:

Ar 1 —Si(OR 1 ) 3   [1]

wherein Ar 1 is a phenyl group having at least one group having a polymerizable double bond or a naphthyl group having at least one group having a polymerizable double bond, and R 1 is a methyl group or an ethyl group;

Ar 2 —Si(OR 2 ) 3   [2]

wherein Ar 2 is a phenyl group optionally substituted by a C 1-6 alkyl group, or a naphthyl group optionally substituted by a C 1-6 alkyl group, and R 2 is a methyl group or an ethyl group; and

wherein R 3 and R 4 are each independently a hydrogen atom or a methyl group, L 1 and L 2 are each independently a phenylene group optionally having a substituent, L 3 and L 4 are each independently a C 1-6 alkylene group, and m and n are 0 or a positive integer such that m+n is 0 to 40.

2. The polymerizable composition according to claim 1 , further comprising 10 to 100 parts by mass of (c) (meth)acrylate compound that is different from the fluorene compound.

3. The polymerizable composition according to claim 2 , wherein the (c) (meth)acrylate compound is a mono(meth)acrylate compound having an aromatic group.

4. The polymerizable composition according to claim 1 , wherein the (a) reactive silsesquioxane compound is a reactive silsesquioxane compound obtained by polycondensation of a compound of Formula [1a] with a compound of Formula [2a] in the presence of an acid or a base, where the Formulae [1a] and [2a] are as follows:

wherein R 1 has the same meaning as described above; and

wherein R 2 has the same meaning as described above.

5. The polymerizable composition according to claim 1 , wherein a cured product obtained from the composition has an Abbe number of 32 or less.

6. A cured product obtained by polymerization of the polymerizable composition according to claim 1 .

7. A material for a high-refractive index resin lens that comprises the polymerizable composition according to claim 1 .

8. A method for producing a molded body comprising the steps of:

charging a space between a support and a mold with a polymerizable composition;

exposing the charged composition to light resulting in photopolymerization;

releasing a photopolymerized product on the support from the mold; and

heating the photopolymerized product together with the support; wherein the polymerizable composition comprises:

(a) 100 parts by mass of reactive silsesquioxane compound obtained by polycondensation of an alkoxy silicon compound A of Formula [1] with an alkoxy silicon compound B of Formula [2] in the presence of an acid or a base, and (b) 10 to 500 parts by mass of a fluorene compound of Formula [3], where the Formulae [1], [2] and [3] are as follows:

Ar 1 —Si(OR 1 ) 3   [1]

wherein Ar 1 is a phenyl group having at least one group having a polymerizable double bond or a naphthyl group having at least one group having a polymerizable double bond, and R 1 is a methyl group or an ethyl group;

Ar 2 —Si(OR 2 ) 3   [2]

wherein Ar 2 is a phenyl group optionally substituted by a C 1-6 alkyl group, or a naphthyl group optionally substituted by a C 1-6 alkyl group, and R 2 is a methyl group or an ethyl group; and

wherein R 3 and R 4 are each independently a hydrogen atom or a methyl group, L 1 and L 2 are each independently a phenylene group optionally having a substituent, L 3 and L 4 are each independently a C 1-6 alkylene group, and m and n are 0 or a positive integer such that m+n is 0 to 40.

9. The method according to claim 8 , wherein the molded body is a lens for a camera module.

10. A polymerizable composition comprising

(a) 100 parts by mass of reactive silsesquioxane compound, the 100 parts by mass of reactive silsesquioxane compound obtained by a reaction consisting of a polycondensation of an alkoxy silicon compound A of Formula [1] with an alkoxy silicon compound B of Formula [2] in the presence of an acid or a base, and optionally a solvent, and

(b) 10 to 500 parts by mass of a fluorene compound of Formula [3], where the Formulae [1], [2] and [3] are as follows:

Ar 1 —Si(OR 1 ) 3   [1]

wherein Ar 1 is a phenyl group having at least one group having a polymerizable double bond or a naphthyl group having at least one group having a polymerizable double bond, and R 1 is a methyl group or an ethyl group;

Ar 2 —Si(OR 2 ) 3   [2]

wherein Ar 2 is a phenyl group optionally substituted by a C 1-6 alkyl group, or a naphthyl group optionally substituted by a C 1-6 alkyl group, and R 2 is a methyl group or an ethyl group; and

wherein R 3 and R 4 are each independently a hydrogen atom or a methyl group, L 1 and L 2 are each independently a phenylene group optionally having a substituent, L 3 and L 4 are each independently a C 1-6 alkylene group, and m and n are 0 or a positive integer such that m+n is 0 to 40.

11. The polymerizable composition according to claim 10 , further comprising 10 to 100 parts by mass of (c) (meth)acrylate compound that is different from the fluorene compound.

12. The polymerizable composition according to claim 11 , wherein the (c) (meth)acrylate compound is a mono(meth)acrylate compound having an aromatic group.

13. The polymerizable composition according to claim 10 , wherein the (a) reactive silsesquioxane compound is a reactive silsesquioxane compound obtained by polycondensation of a compound of Formula [1a] with a compound of Formula [2a] in the presence of an acid or a base, where the Formulae [1a] and [2a] are as follows:

wherein R 1 has the same meaning as described above; and

wherein R 2 has the same meaning as described above.

14. The polymerizable composition according to claim 10 , wherein a cured product obtained from the composition has an Abbe number of 32 or less.

15. A cured product obtained by polymerization of the polymerizable composition according to claim 10 .

16. A material for a high-refractive index resin lens that comprises the polymerizable composition according to claim 10 .

Assignments (2)
CHANGE OF NAME Recorded Jan 21, 2022
From: NISSAN CHEMICAL INDUSTRIES, LTD.
To: NISSAN CHEMICAL CORPORATION
Reel/Frame 058813/0182 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 29, 2016
From: OHMORI, KENTARO; NAGASAWA, TAKEHIRO
To: NISSAN CHEMICAL INDUSTRIES, LTD.
Reel/Frame 039566/0126 →
Priority Claims (1)
JP 2014-038738 · Feb 28, 2014 · national
Continuity (1)
Related Publication 20160369029A1 · Dec 22, 2016