IP Library Granted Patent US 8,173,745
Granted Patent B2
US 8,173,745 · App. 12/639,726 · Granted May 8, 2012

Compositions useful for preparing composites and composites produced therewith

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Quick Facts
Patent No.
US 8,173,745
App. No.
12/639,726
Granted
May 8, 2012
Kind
B2
Abstract

A composite prepared using a thermosettable epoxy resin composition having, as components: (1) an epoxy resin; (2) an epoxidized cycloaliphatic dicyclopentadiene phenolic resin; (3) an optional epoxidized bisphenol-A novolac resin; (4) an optional oligomeric butadiene; (5) an optional organic solvent; and (6) an alkylphenol novolac resin, the alkylphenol novolac resin serving as a curing agent. The composite so prepared may have good physical properties and superior a electrical properties as compared to conventional composites, such as laminates. The prepregs used to make the laminates may have a better surface appearance as well.

Claims (43)

1. A composite prepared using a thermosettable epoxy resin composition, the thermosettable epoxy resin composition having been prepared using formulation components comprising:

an epoxy resin;

an epoxidized cycloaliphatic dicyclopentadiene phenolic resin;

an alkylphenol novolac resin; and

an oligomeric butadiene homopolymer having a weight average molecular weight (Mw) of from about 1,000 to about 20,000 Daltons,

wherein the alkylphenol novolac resin serves as a curing agent.

2. The composite of claim 1 wherein the formulation components used to prepare the thermosettable epoxy resin additionally comprise an epoxidized bisphenol-A novolac resin.

3. The composite of claim 1 wherein the epoxy resin is present, as a weight percentage of all formulation components, from about 30 wt % to about 80 wt %.

4. The composite of claim 1 wherein epoxidized cycloaliphatic dicyclopentadiene phenolic resin utilized in the composition is produced from an epihalohydrin and a dicyclopentadiene polyphenolic compound having the general formula:

wherein “n” represents a whole number from 0 to 7; Ph is a phenylol radical derived from mononuclear phenol, and D is a tricyclodecylene radical having a general formula:

5. The composite of claim 4 wherein the epoxidized cycloaliphatic dicyclopentadiene phenolic resin is present, as a weight percentage of all formulation components, from about 5 wt % to about 70 wt %.

6. The composite of claim 2 wherein the epoxidized bisphenol-A novolac resin component is present, as a weight percentage of all formulation components, from about 10 wt % to about 40 wt %.

7. The composite of claim 1 wherein the oligomeric butadiene component is present, as a weight percentage of all formulation components, from about 0.05 wt % to about 4 wt %.

8. The composite of claim 1 wherein the formulation components further comprise a solvent component, and the solvent component is present, as a weight percentage of all formulation components, from about 15 wt % to about 50 wt %.

9. The composite of claim 1 wherein the alkylphenol novolac resin serving as the curing agent has the general formula:

where:

Ar represents an aryl or alkyl-aryl group;

each Ar group contains x number of non-aromatic carbon atoms,

OH represents a hydroxyl group bonded to each Ar group,

each R 1 represents substituent group(s) bonded to each Ar group,

each R 2 represents a group connecting adjacent Ar groups,

n is a number between 2 and 20,

x is an integer from 4 to 8,

y is an integer from 1 to x−2, and

z is an integer from 1 to x−3.

10. The composite of claim 9 wherein the alkylphenol novolac resin serving as the curing agent has the general formula:

wherein:

R 1 represents a single alkyl substituent in the para position having from 4 to 9 carbon atoms and is sometimes a butyl or octyl group and R 2 is a methylene group.

11. The composite of claim 10 wherein a ratio of the total epoxy groups to the phenolic hydroxyl equivalents is between about 0.5 to about 1.5.

12. The composite of claim 1 wherein the oligomeric butadiene homopolymer comprises a 1, 2 vinyl group content from 25 to about 99 percent.

13. The composite of claim 1 wherein the formulation components, when cured, have a T g of about 150° C. or greater and a T d of 300° C. or greater.

14. A prepreg prepared using a thermosettable epoxy resin composition, the thermosettable epoxy resin composition having been prepared using formulation components comprising:

an epoxy resin;

an epoxidized cycloaliphatic dicyclopentadiene phenolic resin;

an epoxidized bisphenol A novolac resin;

an oligomeric butadiene homopolymer; and

an alkylphenol novolac resin,

wherein the alkylphenol novolac resin serves as a curing agent.

15. The prepreg of claim 14 wherein the epoxy resin is present, as a weight percentage of all formulation components, from about 30 wt % to about 80 wt %.

16. The prepreg of claim 14 wherein the epoxidized cycloaliphatic dicyclopentadiene phenolic resin is present, as a weight percentage of all formulation components, from about 5 wt % to about 70 wt %.

17. The prepreg of claim 14 wherein the epoxidized bisphenol-A novolac resin component is present, as a weight percentage of all formulation components, from about 10 wt % to about 40 wt %.

18. The prepreg of claim 14 wherein the oligomeric butadiene component is present, as a weight percentage of all formulation components, from about 0.05 wt % to about 4 wt %.

19. A laminate comprising the prepreg of claim 14 .

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2022
From: HEXION INC.
To: WESTLAKE EPOXY INC.
Reel/Frame 061611/0876 →
PARTIAL TERMINATION AND RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (ABL) Recorded Feb 1, 2022
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 058932/0915 →
PARTIAL TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) Recorded Feb 1, 2022
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 058932/0923 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (030146/0970) Recorded Jul 9, 2019
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.)
Reel/Frame 049706/0264 →
PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Recorded Apr 3, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT
Reel/Frame 048788/0617 →
RELEASE OF SECURITY INTEREST Recorded Feb 23, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION (SUCCESSOR BY MERGER TO WILMINGTON TRUST FSB), AS COLLATERAL AGENT
To: HEXION INC. (FORMERLY KNOWN AS HEXION SPECIALTY CHEMICALS INC.); BORDEN CHEMICAL FOUNDRY, LLC; HEXION INVESTMENTS INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INVESTMENTS, INC.); HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; HEXION INTERNATIONAL INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INTERNATIONAL INC.); OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
Reel/Frame 041793/0001 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →