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

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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 (4)
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 →