IP Library Granted Patent US 8,871,870
Granted Patent B2
US 8,871,870 · App. 13/840,056 · Granted Oct 28, 2014

Synthesized resins and varnishes and prepegs and laminates made therefrom

Inventors: Guroen He (Chandler, AZ); Tarun Amla (Chandler, AZ); Larry D. Olson (Viroqua, WI); Peggy Conn (Chandler, AZ)
Assignee: Isola USA Corp.
C09D153/02C08F2810/20C08F36/06C08C19/22C09D147/00C08F271/02C08K5/00C08F36/04C09D109/00C09D109/06
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Quick Facts
Patent No.
US 8,871,870
App. No.
13/840,056
Granted
Oct 28, 2014
Kind
B2
Abstract

Synthesized base resin compositions that include a raw resin and a maleimide and/or bismaleimide monomer as well as compounded varnishes that include a raw resin or synthesized base resin as well as a monomer, flame retardant and initiator as well as prepregs and laminates made using the synthesized base resin and compounded varnishes.

Claims (41)

1. A method of preparing a synthesized base resin by the steps of:

admixing in the presence of a solvent, from about 1 to about 99 wt % of at least one unsaturated polyolefin polymer and from about 1 to about 50 wt % of at least one monomer of a mono maleimide, a bismaleimide and combinations thereof;

adding an initiator to the admixture to form a reactive mixture;

heating the reactive mixture to a temperature of from about 90 to about 105° C. and allowing the reactive mixture to react for a period of time sufficient for the reactive mixture to reach a viscosity of from about 300-1000 cP measured at 25° C.; and

adding an inhibitor to the reactive mixture to stop the reaction wherein the admixture does not include a polyphenylene ether.

2. The method of claim 1 wherein the solvent includes dimethylformamide in an amount ranging from greater that 0 to about 50% of the weight the base co-polymer admixture.

3. The method of claim 1 wherein the solvent includes dimethylformamide and toluene.

4. The method of claim 1 wherein the unsaturated polyolefin polymer has a molecular weight of from about 1000 to about 5000.

5. The method of claim 1 wherein the at least one monomer of a mono maleimide, a bismaleimide and combinations thereof is a mono maleimide monomer.

6. The method of claim 1 wherein the synthesized base resin includes from about 30 to about 70 wt % of an unsaturated polyolefin polymer and from about 5 to about 35 wt % of the at least one mono maleimide monomer.

7. The method of claim 1 wherein the admixture further includes a reactive monomer.

8. The method of claim 7 wherein the reactive monomer is at least one styrenic monomer.

9. The method of claim 7 wherein the reactive monomer is a soluble halogenated monomer.

10. The method of claim 1 wherein the admixture includes an adhesion promoter.

11. The method of claim 10 wherein the adhesion promoter is one or more di-functional methacrylates of urethane.

12. The method of claim 1 wherein the at least one monomer of a mono maleimide, a bismaleimide and combinations thereof is selected from the group consisting of N-phenyl-maleimide; N-phenyl-methylmaleimide; N-phenyl-chloromaleimide; N-p-chlorophenyl-maleimide; N-p-methoxyphenyl-maleimide; N-p-methylphenyl-maleimide; N-p-nitrophenyl-maleimide; N-p-phenoxyphenyl-maleimide; N-p-phenylaminophenyl-maleimide; N-p-phenoxycarbonylphenyl-maleimide; 1-maleimido-4-acetoxysuccinimido-benzene; 4-maleimido-4′-acetoxysuccinimido-diphenylmethane; 4-maleimido-4′-acetoxysuccinimido-diphenyl ether; 4-maleimido-4′-acetamido-diphenyl ether; 2-maleimido-6-acetamido-pyridine; 4-maleimido-4′-acetamido-diphenylmethane N-p-phenylcarbonylphenyl-maleimide; N-ethylmaleimide; N-2.6-xylylmaleimide; N-cyclohexylmaleimide; N-2,3-xylylmaleimide; xylyl maleimide, 2,6-xylenemaleimide; 4,4′-bismaleimidodiphenylmethane and combinations thereof.

13. A method of preparing a synthesized base resin comprising the steps of:

admixing in the presence of a solvent, from about 1 to about 99 wt % of at least one unsaturated polyolefin polymer, from about 1 to about 50 wt % of at least one monomer of a mono maleimide, a bismaleimide and combinations thereof and a reactive monomer;

adding an initiator to the admixture to form a reactive mixture;

heating the reactive mixture to a temperature of from about 90 to about 105° C. and allowing the reactive mixture to react for a period of time sufficient for the reactive mixture to reach a viscosity of from about 300-1000 cP measured at 25° C.; and adding an inhibitor to the reactive mixture to stop the reaction wherein the admixture further includes a reactive monomer, wherein the reactive monomer is a soluble halogenated monomer, and wherein the soluble halogenated monomer is dibromostyrene.

14. The method of claim 13 wherein the admixture is formed by the further steps of:

i. combining the at least one unsaturated polyolefin polymer, at least on solvent and an initiator to form a first solution;

ii. preparing a second solution by mixing the at least one monomer of a mono maleimide, a bismaleimide and combinations thereof and the reactive monomer; and

iii. adding the second solution into the first solution over several hours.

15. A method of preparing a synthesized base resin comprising the steps of:

admixing in the presence of a solvent, from about 1 to about 99 wt % of a copolymer of butadiene-styrene and from about 1 to about 50 wt % of at least one monomer of a mono maleimide, a bismaleimide and combinations thereof;

adding an initiator to the admixture to form a reactive mixture;

heating the reactive mixture to a temperature of from about 90 to about 105° C. and allowing the reactive mixture to react for a period of time sufficient for the reactive mixture to reach a viscosity of from about 300-1000 cP measured at 25° C.; and adding an inhibitor to the reactive mixture to stop the reaction.

16. A method of preparing a synthesized base resin by the steps of:

admixing in the presence of a solvent, from about 30 to about 70 wt % of an unsaturated polyolefin polymer that is selected from the group consisting of polyisoprene, copolymers of butadiene and styrenic monomers and combinations thereof and from about 5 to about 35 wt % of at least one monomer of a mono maleimide that is selected from the group consisting of N-phenyl-maleimide; N-phenyl-methylmaleimide; N-phenyl-chloromaleimide; N-p-chlorophenyl-maleimide; N-p-methoxyphenyl-maleimide; N-p-methylphenyl-maleimide; N-p-nitrophenyl-maleimide; N-p-phenoxyphenyl-maleimide; N-p-phenylaminophenyl-maleimide; N-p-phenoxycarbonylphenyl-maleimide; 1-maleimido-4-acetoxysuccinimido-benzene; 4-maleimido-4′-acetoxysuccinimido-diphenylmethane; 4-maleimido-4′-acetoxysuccinimido-diphenyl ether; 4-maleimido-4′-acetamido-diphenyl ether; 2-maleimido-6-acetamido-pyridine; 4-maleimido-4′-acetamido-diphenylmethane and N-p-phenylcarbonylphenyl-maleimide; N-ethylmaleimide; N-2.6-xylylmaleimide, N-cyclohexylmaleimide; N-2,3-xylylmaleimide; xylyl maleimide; 2,6-xylenemaleimide or combinations thereof;

adding an initiator to the admixture to form a reactive mixture;

heating the reactive mixture to a temperature of from about 90 to about 105° C. for a time sufficient to allow the reactive mixture to react a viscosity of from about 300-1000 cP measured at 25° C.; and

adding an inhibitor to the reactive mixture to stop the reaction.

17. The method of claim 16 wherein the admixture is made by the further steps of:

preparing a first solution including the unsaturated polyolefin polymer;

preparing a second solution including the at least one monomer of a mono maleimide and at least one reactive monomer; and

combining the first solution and second solution to form the admixture.

18. The method of claim 17 wherein the at least one reactive monomer is a soluble halogenated monomer.

19. The method of claim 18 wherein the soluble halogenated monomer is dibromostyrene, pentabromobenzyl acrylate and combinations thereof.

20. The method of claim 17 wherein a reactive monomer is added to the first solution.

21. The method of claim 16 wherein the admixture includes an adhesion promoter.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Jun 17, 2026
From: CERBERUS BUSINESS FINANCE, LLC
To: ISOLA USA CORP.
Reel/Frame 075784/0206 →
SECURITY INTEREST Recorded Jan 2, 2018
From: ISOLA USA CORP.
To: CERBERUS BUSINESS FINANCE, LLC, AS COLLATERAL AGENT (FIRST LIEN)
Reel/Frame 044519/0030 →
ASSIGNMENT OF SECURITY AGREEMENT Recorded May 16, 2017
From: JEFFERIES FINANCE LLC
To: CERBERUS BUSINESS FINANCE, LLC
Reel/Frame 042467/0299 →
SECURITY AGREEMENT Recorded Dec 3, 2013
From: ISOLA USA CORP.
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 031752/0404 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 5, 2013
From: HE, GUROEN; AMLA, TARUN; OLSON, LARRY D.; CONN, PEGGY
To: ISOLA USA CORP.
Reel/Frame 031548/0350 →
Continuity (3)
Continuation PCTUS2013022549 · Jan 22, 2013
Provisional Application 61588528 · Jan 19, 2012
Related Publication 20140011962A1 · Jan 9, 2014