Polymerizable compositions, cured products obtained therewith, and use of these materials

Patent metadata

Field	Value
Publication number	US-9434818-B2
Application number	US-201113980501-A
Country	US
Kind code	B2
Filing date	Jan 21, 2011
Priority date	Jan 21, 2011
Publication date	Sep 6, 2016
Grant date	Sep 6, 2016

Abstract

[Problem] To provide a polymerizable composition having an excellent transparency in near-infrared wavelength and excellent heat resistance, and a method for producing the same. [Means of Solving the Problem] A polymerizable composition includes: a reactive silicone compound obtained by polycondensing a diaryl silicic acid compound of Formula [1] below with a silane compound, selected under compounds of Formula [2] and Formula [2b] below in the presence of an acid or a base; and (b) a compound having at least one polymerizable group selected from the group consisting of alkenyl group and (meth)acryl group, wherein Ar 1 and Ar 2 are independently a phenyl group optionally substituted with a C 1 -C 6 alkyl group, and X is a group which can undergo a hydrolytic condensation reaction, and wherein Ar 3 is naphthyl or anthracyl substituted with at least one group having a polymerizable double bond, or wherein Ar 3 is phenyl substituted with at least one group having a polymerizable double bond other than vinyl, or is phenyl substituted with at least two groups having a polymerizable double bond.

First claim

The invention claimed is:

1. A polymerizable composition comprising:
(a) a reactive silicone compound obtained by polycondensing a diaryl silicic acid compound of Formula [1] below with a silane compound, selected under compounds of Formula [2] and Formula [2b] below in the presence of an acid or a base;

wherein Ar 1 and Ar 2 are independently a phenyl group optionally substituted with a C 1 -C 6 alkyl group, and X is a group which can undergo a hydrolytic condensation reaction, and wherein Ar 3 is naphthyl or anthracyl substituted with at least one group having a polymerizable double bond, or wherein Ar 3 is phenyl substituted with at least one group having a polymerizable double bond other than vinyl, or is phenyl substituted with at least two groups having a polymerizable double bond, and
(b) a compound having at least one polymerizable alkenyl group of Formula [3],

wherein R 1 is a hydrogen atom or methyl group, L is a hydrogen atom, a C 1-20 aliphatic hydrocarbon residue having m-valence that is optionally substituted with a phenyl group, a C 1-20 aliphatic hydrocarbon residue having m-valence that optionally contains an ether bond, or a C 1-20 polyvalent alcohol residue optionally containing an ether bond, Ar 4 is a monocyclic or bicyclic or tricyclic, in each case aromatic hydrocarbon residue with n+1 valences, m is 1 and n is 2; or
wherein R 1 is a hydrogen atom or methyl group, L is a single bond, an oxygen atom, a C 1-20 aliphatic hydrocarbon residue having m-valence that is optionally substituted with a phenyl group, a C 1-20 aliphatic hydrocarbon residue having m-valence that optionally contains an ether bond, or a C 1-20 polyvalent alcohol residue optionally containing an ether bond, Ar 4 is a monocyclic or bicyclic or tricyclic, in each case aromatic hydrocarbon residue with n+1 valences, m is 2 or 3 and each of n is independently 1 or 2;
with the proviso that when L is a single bond or an oxygen atom, m is 2.

2. The composition according to claim 1 , wherein X is an alkoxy group having 1 to 10 carbon atoms.

3. The composition according to claim 2 , wherein X is methoxy or ethoxy.

4. The composition of claim 1 , wherein Ar 4 is a phenyl residue.

5. The composition according to claim 4 , wherein in the formula [3], n is 2.

6. The composition according to claim 1 , wherein in the formula [3], L is a hydrogen atom, m is 1, and n is 2.

7. The composition according to claim 1 , further comprising inorganic fine particles.

8. The composition according to claim 1 , further comprising a solvent.

9. The composition according to claim 1 , further comprising a polymerization initiator.

10. A cured product obtained by reacting a polymerizable double bond in the reactive silicone compound with a polymerizable group in the compound having at least one polymerizable group, in the composition according to claim 1 .

11. Use of a material comprising a composition according to claim 1 , for the preparation of components of optical devices, such as optical adhesives, transparent sealers, or cores or claddings of optical signal transmission devices, wherein said preparation includes curing the composition by reacting a polymerizable double bond in the reactive silicone compound with a polymerizable group in the compound having at least one polymerizable group, in the presence of a photo-radical initiator or a thermal radical initiator by light irradiation or heating.

12. Use of a material according to claim 1 , for the preparation of optical interconnections of printed wiring boards wherein the optical interconnection is preferably a chip-to-chip optical interconnection, wherein said preparation includes curing the composition by reacting a polymerizable double bond in the reactive silicone compound with a polymerizable group in the compound having at least one polymerizable group, in the presence of a photo-radical initiator or a thermal radical initiator by light irradiation or heating.

13. A cured product as claimed in claim 10 which is a component of optical devices, preferably an optical adhesive, transparent sealer, or core or cladding of optical signal transmission devices.

14. A cured product as claimed in claim 10 which is a component of an optical interconnection of printed wiring boards wherein the optical interconnection is preferably a chip-to-chip optical interconnection.

Assignees

• Popall Michael
• Houbertz-Krauss Ruth
• Cochet Sebastien
• Wolter Herbert
• Ohmori Kentaro
• Sato Tetsuo
• Fraundhofer-Gesellschaft Zur Foerderung Der Angewandter Forschung E V
• Nissan Chemical Ind Ltd

Inventors

• Popall Michael
• Houbertz-Krauss Ruth
• Cochet Sebastien
• Wolter Herbert
• Ohmori Kentaro
• Sato Tetsuo

Classifications

• C08G77/20 Primary

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• C08L43/04

  Homopolymers or copolymers of monomers containing silicon · CPC title

• C09K3/10

  {Materials in mouldable or extrudable form} for sealing or packing joints or covers (filling pastes C09D5/34) · CPC title

• C08G77/80 Primary

  Siloxanes having aromatic substituents, e.g. phenyl side groups · CPC title