Modified liquid diene rubber and resin composition containing modified liquid diene rubber

• US 10,414,834 B2
• Filed: 12/22/2015
• Issued: 09/17/2019
• Est. Priority Date: 12/25/2014
• Status: Active Grant

• Current Assignee: Kuraray Company Limited
• Original Assignee: Kuraray Company Limited
• Inventors: Motoda, Satoshi, Hirata, Kei
• Primary Examiner(s): Grinsted, Ronald
• Application Number:
  US15/538,076
• Publication Number:
  US 20180022835A1
• Time in Patent Office: 1,365 Days
• Field of Search: 524525
• CPC Class Codes: C08C 19/02 Hydrogenation
• CPC Class Codes: C08C 19/28 Reaction with compounds containing carbon-to-carbon unsaturated bonds graft polymers C08F279/00
• CPC Class Codes: C08F 222/06 Maleic anhydride
• CPC Class Codes: C08F 2500/02 Low molecular weight, e.g. <100,000 Da.
• CPC Class Codes: C08F 2500/04 Broad molecular weight distribution, i.e. Mw/Mn > 6
• CPC Class Codes: C08F 279/02 on to polymers of conjugated dienes
• CPC Class Codes: C08F 290/12 Polymers provided for in subclasses C08C or C08F
• CPC Class Codes: C08F 290/128 Polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
• CPC Class Codes: C08F 36/06 Butadiene
• CPC Class Codes: C08F 36/08 Isoprene
• CPC Class Codes: C09D 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
• CPC Class Codes: C09J 109/00 Adhesives based on homopolymers or copolymers of conjugated diene hydrocarbons
• CPC Class Codes: C09J 11/06 organic
• CPC Class Codes: C09J 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Abstract

There are provided a modified liquid diene rubber that can be used for a curable resin composition and a resin composition containing the modified liquid diene rubber. The curable resin composition containing the modified liquid diene rubber has a much higher curing rate than that in the related art, and the resulting cured product has excellent mechanical properties, transparency, and heat resistance. Produced are a modified liquid diene rubber and a resin composition containing the modified liquid diene rubber. The modified liquid diene rubber includes a modifying group (p) partly containing a (meth)acryloyl group therein and a monomer unit (a1) derived from a conjugated diene compound. A carbon-carbon double bond derived from the conjugated diene compound has a hydrogenation rate of 30 to 95 mol %, and the modifying group (p) has a functional group equivalent weight of 700 to 20,000 g/eq.

Claims

1. A modified liquid diene rubber, comprising a modifying group (p) and a monomer unit (a1) derived from a con_jugated diene compound,

wherein a carbon-carbon double bond derived from the conjugated diene compound has a hydrogenation rate of 30 to 95 mol%,

the modifying group (p) comprises at least one structure selected from the group consisting of (p1), (p1′

), (p2) and (p2′

),

and a functional group equivalent weight of the modifying group (p) is from700 to 20,000 g/eq;

2. The modified liquid diene rubber according to claim 1, having a number-average molecular weight of 1,000 to 80,000.

3. The modified liquid diene rubber according to claim 1, having a melt viscosity of 0.1 to 5,000 Pa·

s at 38°

C.

4. The modified liquid diene rubber according to claim 1, wherein the modifying group (p) bonds to a polymer main chain.

5. A resin composition, comprising a modified liquid diene rubber (A) and a radical polymerization initiator (B),

wherein

a content of the radical polymerization initiator (B) is from 0.1 to 20 mass % relative to a total amount of the resin composition,

the modified liquid diene rubber (A) comprises a modifying group (p) having at least one stricture selected from the group consisting of (p1), (p1′

), (p2) and (p2′

), and

a monomer unit (a1) derived from a conjugated diene compound,

a carbon-carbon double bond derived from the conjugated diene compound has a hydrogenation rate of 30 to 95 mol %, and

a functional group equivalent weight of the modifying group (p) is from700 to 20,000 g/eq;

6. The resin composition according to claim 5, further comprising a radically polymerizable monomer (C) having a carbon-carbon double bond,

wherein a mass ratio [(A)/(C)] of the modified liquid diene rubber (A) to the monomer (C) is 0.01 to 100.

7. A cured product, obtained by a process comprising curing the resin composition according to claim 5.

8. An optical adhesive, formed of the resin composition according to claim 5.