Radical polymerization initiator, multi-branched polymer, varnish, adhesive agent, coating material, sealing material, semiconductor, and electronic device

Patent metadata

Field	Value
Publication number	US-9944732-B2
Application number	US-201315105034-A
Country	US
Kind code	B2
Filing date	Dec 27, 2013
Priority date	Dec 27, 2013
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

This invention is intended to synthesize a multi-branched polymer, which has an uniform molecular chain lengths and is free from branch defects, without the need for purification. This invention is also intended to synthesize a polyfunctional radical polymerization initiator represented by Formula 1:

wherein n is an integer of 1 or larger; Y is a polyfunctional unsaturated compound; R 1 is a hydrocarbon group; R 2 is a structure in which one molecule of a radically polymerizable unsaturated hydrocarbon compound is bound to R 1 and the oxygen atom; X 1 of B—X 1 (boron-X 1 ) bond is an alkoxy or phenyl group; and X 2 of B—X 2 (boron-X 2 ) bond is an alkoxy or phenyl group.

First claim

The invention claimed is:

1. A polyfunctional radical polymerization initiator represented by Formula 1:

wherein n is an integer of 1 or larger; Y is a polyfunctional unsaturated compound residue; R 1 is a hydrocarbon group; R 2 is a structure in which one molecule of a radically polymerizable unsaturated hydrocarbon compound is bound to R 1 and the oxygen atom; X 1 of B—X 1 (boron-X 1 ) bond is an alkoxy or phenyl group; and X 2 of B—X 2 (boron-X 2 ) bond is an alkoxy or phenyl group, wherein the polyfunctional unsaturated compound residue has a branched or cyclic molecular structure and comprises at least one of hydrocarbon, nitrogen, silicon, and phosphorus.

2. The polyfunctional radical polymerization initiator according to claim 1 , wherein the structure of R 2 is, as an unsaturated hydrocarbon compound residue before it is positioned between R 1 and the oxygen atom, selected from the group consisting of an aromatic vinyl compound, an aromatic allyl compound, a heterocycle-containing vinyl compound, a heterocycle-containing an allyl compound, an alkyl (meth)acrylate, an unsaturated monocarboxylic acid ester, a fluoroalkyl (meth)acrylate, a siloxanyl compound, a mono(meth)acrylate and di(meth)acrylate of an alkylene glycol, an alkoxyalkyl (meth)acrylate, a cyanoalkyl (meth)acrylate, acrylonitrile, and methacrylonitrile.

3. The polyfunctional radical polymerization initiator according to claim 1 , wherein the structure of R 2 is, as an unsaturated hydrocarbon compound residue before it is positioned between R 1 and the oxygen atom, selected from the group consisting of an oligo(meth)acrylate of a polyhydric alcohol, a hydroxyalkyl (meth)acrylate, a hydroxyalkylester of an unsaturated carboxylic acid, an unsaturated alcohol, an unsaturated (mono)carboxylic acid, an unsaturated polycarboxylic acid, an unsaturated polycarboxylic anhydrate, a monoester and diester of an unsaturated polycarboxylic acid or unsaturated polycarboxylic anhydrate, an epoxy-group-containing unsaturated compound, a diene compound, vinyl chloride, vinyl acetate, sodium isoprene sulfonate, a cinnamic acid ester, a crotonic acid ester, dicyclopentadienyl, and ethylidene norbornene.

4. The polyfunctional radical polymerization initiator according to claim 1 , wherein the polyfunctional unsaturated compound residue has a structure having one atom as a center skeleton and at least two unsaturated hydrocarbon groups bound to the atom.

5. A polyfunctional radical polymerization initiator represented by Formula 1:

wherein n is an integer of 1 or larger; Y is a polyfunctional unsaturated compound residue; R 1 is a hydrocarbon group; R 2 is a structure in which one molecule of a radically polymerizable unsaturated hydrocarbon compound is bound to R 1 and the oxygen atom; X 1 of B—X 1 (boron-X 1 ) bond is an alkoxy or phenyl group; and X 2 of B—X 2 (boron-X 2 ) bond is an alkoxy or phenyl group, wherein the polyfunctional unsaturated compound residue has a molecular structure selected from the group consisting of ester bond, urethane bond, amide bond, thioester bond, siloxane bond, carbonyl group, carboxyl group, amino group, alkylamino group, and dialkylamino group.

6. A polyfunctional radical polymerization initiator represented by Formula 1:

wherein n is an integer of 1 or larger; Y is a polyfunctional unsaturated compound residue; R 1 is a hydrocarbon group; R 2 is a structure in which one molecule of a radically polymerizable unsaturated hydrocarbon compound is bound to R 1 and the oxygen atom; X 1 of B—X 1 (boron-X 1 ) bond is an alkoxy or phenyl group; and X 2 of B—X 2 , (boron-X 2 ) bond is an alkoxy or phenyl group, wherein the polyfunctional unsaturated compound residue has a molecular structure selected from the group consisting of pyridyl group, pyrrolidyl group, isocyanuric acid ester skeleton, cyanuric acid ester skeleton, hexahydrotriazine skeleton, maleimide skeleton, imidazole skeleton, and organic silicon skeleton.

7. The polyfunctional radical polymerization initiator according to claim 1 , wherein R 1 —R 2 bond is alkyl bond.

8. A multi-branched polymer prepared through polymerization with the use of the polymerization initiator according to claim 7 .

9. The polyfunctional radical polymerization initiator according to claim 5 , wherein R 1 —R 2 bond is alkyl bond.

10. A multi-branched polymer prepared through polymerization with the use of the polymerization initiator according to claim 9 .

11. The polyfunctional radical polymerization initiator according to claim 6 , wherein R 1 —R 2 bond is alkyl bond.

12. A multi-branched polymer prepared through polymerization with the use of the polymerization initiator according to claim 11 .

Assignees

• Hitachi Ltd

Inventors

• Kajihara Yuri
• Muraki Takahito
• Nunoshige Jun

Classifications

• H10W90/756

  between a chip and a stacked lead frame, conducting package substrate or heat sink · CPC title

• H10W74/00

  Encapsulations, e.g. protective coatings · CPC title

• C09J133/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C09J125/06

  Polystyrene · CPC title

• C09D133/12

  Homopolymers or copolymers of methyl methacrylate · CPC title