IP Library Granted Patent US 11,932,716
Granted Patent B2
US 11,932,716 · App. 17/264,034 · Granted Mar 19, 2024

Radiaton curable resin composition

Inventors: Noriyasu Shinohara (Tokyo, JP); Seiichirou Takahashi (Tokyo, JP)
Assignee: Covestro (Netherlands) B.V.
C08F283/008C03C25/326C03C25/6226G02B6/02395
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Quick Facts
Patent No.
US 11,932,716
App. No.
17/264,034
Granted
Mar 19, 2024
Kind
B2
Abstract

There is provided a radiation-curable resin composition for formation of a primary covering layer, the radiation-curable resin composition being able to form a cured layer having excellent flexibility and adequate mechanical strength. A radiation-curable resin composition for formation of a primary covering layer of an optical fiber, comprising a urethane oligomer, a polymerization initiator and a free-radically polymerizable non-urethane monomer, the urethane oligomer being the reaction product of a polyether-based urethane prepolymer and an isocyanate reactive compound containing one active hydrogen group, the isocyanate reactive compound containing an aliphatic alcohol and an ethylenic unsaturated group-containing isocyanate reactive compound, and the aliphatic alcohol content in the isocyanate reactive compound being 24 mol % or higher.

Claims (40)

1. A radiation-curable resin composition for formation of a primary covering layer of an optical fiber, comprising a urethane oligomer with an ethylenic unsaturated group, a free-radically polymerizable non-urethane monomer and a polymerization initiator, wherein

the urethane oligomer with an ethylenic unsaturated group is the reaction product of a polyether-based urethane prepolymer and an isocyanate reactive compound containing one active hydrogen group,

the isocyanate reactive compound contains an aliphatic alcohol and an ethylenic unsaturated group-containing isocyanate reactive compound,

the aliphatic alcohol content in the isocyanate reactive compound is 24 mol % or higher, and

the urethane oligomer with an ethylenic unsaturated group contains a monofunctional urethane (meth)acrylate oligomer and a bifunctional urethane (meth)acrylate oligomer wherein a ratio of the number of moles of the monofunctional urethane (meth)acrylate oligomer with respect to the number of moles of the bifunctional urethane (meth)acrylate oligomer is from 3/1 to 100/1.

2. The radiation-curable resin composition according to claim 1 , wherein the radiation-curable resin composition possesses a curing speed S of 15% or higher as defined by the following formula (1):

S (%)= Y 20 /Y 1000 ×100; wherein  formula (1):

per the formula, Y 1000 and Y 20 each represent a Young's modulus at 23° C. for cured films of the radiation-curable resin composition, wherein the cured films are created under a 1 J/cm 2 curing condition for Y 1000 , and a 20 mJ/cm 2 curing condition for Y 20 .

3. The radiation-curable resin composition according to claim 1 , wherein the Young's modulus at 25° C. for the cured film of the radiation-curable resin composition with curing conditions of 1 J/cm 2 is 0.8 MPa or smaller.

4. The radiation-curable resin composition according to claim 1 , wherein the free-radically polymerizable non-urethane monomer contains at least one vinyl group-containing compound selected from the group consisting of vinyl ester compounds and vinylamide compounds.

5. The radiation-curable resin composition according to claim 4 , wherein the vinylamide compound contains N-vinylcaprolactam.

6. The radiation-curable resin composition according to claim 5 , wherein at least a portion of the urethane oligomer with an ethylenic unsaturated group and/or free-radically polymerizable non-urethane monomer is a (meth)acryloyl group-containing compound, and

a ratio of the number of moles of the (meth)acryloyl group-containing compound with respect to the number of moles of the vinyl group-containing compound is from 1/1 to 10/1.

7. The radiation-curable resin composition according to claim 1 , wherein the urethane oligomer with an ethylenic unsaturated group and the free-radically polymerizable non-urethane monomer comprise an ethylenic unsaturated group, and

a ratio of the number of moles of monofunctional compounds with one ethylenic unsaturated group with respect to the number of moles of polyfunctional compounds with two or more ethylenic unsaturated groups is from 2/1 to 100/1.

8. The radiation-curable resin composition according to claim 6 , wherein

the urethane oligomer with an ethylenic unsaturated group or the free-radically polymerizable non-urethane monomer contains a monofunctional (meth)acrylate and a polyfunctional (meth)acrylate, and

a ratio of the number of moles of the monofunctional (meth)acrylate in the radiation-curable resin composition with respect to the number of moles of the polyfunctional (meth)acrylate is from 1/1 to 75/1.

9. The radiation-curable resin composition according to claim 1 , wherein the number-average molecular weight of the urethane oligomer with an ethylenic unsaturated group is 2000 or greater.

10. The radiation-curable resin composition according to claim 1 , wherein the urethane oligomer with an ethylenic unsaturated group contains an alkoxysilyl group-containing urethane oligomer having one (meth)acryloyl group at one end and one alkoxysilyl group at the other end.

11. The radiation-curable resin composition according to claim 10 , wherein

a ratio of the number of moles of the alkoxysilyl group-containing urethane oligomer with respect to the number of moles of the monofunctional urethane (meth)acrylate oligomer other than the alkoxysilyl group-containing urethane oligomer is from 0.01/1 to 0.7/1.

12. The radiation-curable resin composition according to claim 11 , wherein

a ratio of the number of moles of the alkoxysilyl group-containing urethane oligomer with respect to the number of moles of the bifunctional urethane (meth)acrylate oligomer is from 0.2/1 to 20/1.

13. The radiation-curable resin composition according to claim 12 , wherein the free-radically polymerizable non-urethane monomer contains a free-radically polymerizable alkoxysilane.

14. The radiation-curable resin composition according to claim 13 , wherein the free-radically polymerizable alkoxysilane has a (meth)acryloyl group.

15. The radiation-curable resin composition according to claim 14 , wherein

the urethane oligomer with an ethylenic unsaturated group contains an alkoxysilyl group-containing urethane oligomer having one (meth)acryloyl group at one end and one alkoxysilyl group at the other end, and

the molar ratio of the alkoxysilyl group-containing urethane oligomer with respect to the free-radically polymerizable alkoxysilane is from 0.1/1 to 10/1.

16. The radiation-curable resin composition according to claim 1 , further comprising a non-free-radically polymerizable alkoxysilane.

17. The radiation-curable resin composition according to claim 16 , wherein

the urethane oligomer with an ethylenic unsaturated group contains an alkoxysilyl group-containing urethane oligomer having one (meth)acryloyl group at one end and one alkoxysilyl group at the other end, and

a molar ratio of the number of moles of the alkoxysilyl group-containing urethane oligomer with respect to the number of moles of the non-free-radically polymerizable alkoxysilane is from 0.01/1 to 4/1.

18. The radiation-curable resin composition according to claim 17 , wherein

the free-radically polymerizable non-urethane monomer contains a free-radically polymerizable alkoxysilane, and

the ratio of the number of moles of the free-radically polymerizable alkoxysilane with respect to the number of moles of the non-free-radically polymerizable alkoxysilane is from 0.01/1 to 3/1.

19. The radiation-curable resin composition according to claim 18 , wherein

the urethane oligomer with an ethylenic unsaturated group contains an alkoxysilyl group-containing urethane oligomer having one (meth)acryloyl group at one end and one alkoxysilyl group at the other end, and a free-radically polymerizable alkoxysilane, and

the free-radically polymerizable non-urethane monomer contains a free-radically polymerizable alkoxysilane, and

the ratio of the total number of moles of the alkoxysilyl group-containing urethane oligomer and the free-radically polymerizable alkoxysilane with respect to the number of moles of the non-free-radically polymerizable alkoxysilane is from 0.05/1 to 4/1.

Assignments (5)
CHANGE OF CORPORATE ADDRESS Recorded Mar 30, 2022
From: COVESTRO (NETHERLANDS) B.V.
To: COVESTRO (NETHERLANDS) B.V.
Reel/Frame 059546/0570 →
CHANGE OF NAME Recorded Aug 13, 2021
From: MS HOLDING B.V.
To: COVESTRO (NETHERLANDS) B.V.
Reel/Frame 057182/0645 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 13, 2021
From: DSM IP ASSETS B.V.
To: MS HOLDING B.V.
Reel/Frame 057182/0882 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2021
From: JAPAN FINE COATINGS CO. LTD.
To: DSM IP ASSETS B.V.
Reel/Frame 055502/0920 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2021
From: SHINOHARA, NORIYASU; TAKAHASHI, SEIICHIROU
To: DSM IP ASSETS B.V.
Reel/Frame 055145/0303 →
Cited By (1)
US 12,583,789