IP Library Granted Patent US 8,445,590
Granted Patent B2
US 8,445,590 · App. 13/442,695 · Granted May 21, 2013

Compositions useful for preparing composites and composites produced therewith

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Quick Facts
Patent No.
US 8,445,590
App. No.
13/442,695
Granted
May 21, 2013
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 (41)

1. An epoxy resin composition comprising:

an epoxy resin component;

an epoxidized cycloaliphatic dicyclopentadiene phenolic resin;

an alkylphenol novolac resin; and

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

2. The epoxy resin composition of claim 1 further comprising an epoxidized bisphenol-A novolac resin.

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

4. The epoxy resin composition 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 epoxy resin composition of claim 1 wherein the epoxidized cycloaliphatic dicyclopentadiene phenolic resin is present, as a weight percentage of the composition, from about 5 wt % to about 70 wt %.

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

7. The epoxy resin composition of claim 1 wherein the oligomeric butadiene component is present, as a weight percentage of the composition, from about 0.05 wt % to about 4 wt %.

8. The epoxy resin composition of claim 1 further comprising a solvent component, and the solvent component is present, as a weight percentage of the composition, from about 15 wt % to about 50 wt %.

9. The epoxy resin composition 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 epoxy resin composition of claim 1 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 methyl group.

11. The epoxy resin composition of claim 1 wherein a ratio of the total epoxy groups to the phenolic hydroxyl equivalents is between about 0.5 to about 1.5.

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

13. The epoxy resin composition of claim 1 wherein the composition, when cured, has a T g of about 150° C. or greater and a T d of 300° C. or greater.

14. A process for forming a composition, comprising:

providing an epoxy resin and an epoxidized cycloaliphatic dicyclopentadiene phenolic resin to a reactor to form a mixture; and

providing an oligomeric butadiene homopolymer and an alkylphenol novolac resin to the mixture.

15. The process of claim 14 , wherein:

the epoxy resin is present, as a weight percentage, from about 30 wt % to about 80 wt %;

the epoxidized cycloaliphatic dicyclopentadiene phenolic resin is present, as a weight percentage of the composition, from about 5 wt % to about 70 wt %;

the epoxidized bisphenol-A novolac resin component is present, as a weight percentage of the composition, from about 10 wt % to about 40 wt %; and

the oligomeric butadiene component is present, as a weight percentage of the composition, from about 0.05 wt % to about 4 wt %; and wherein the total amount of components is 100 wt. %.

16. The process of claim 14 , wherein the process further comprises adding a solvent component with the providing the epoxy resin and the epoxidized cycloaliphatic dicyclopentadiene phenolic resin, adding a solvent component with the providing the oligomeric butadiene homopolymer and the alkylphenol novolac resin, or both.

17. The process of claim 16 , wherein the solvent component is present, as a weight percentage of the composition, from about 15 wt % to about 50 wt %.

18. The process of claim 14 , further comprising impregnating a substrate with the composition.

Assignments (17)
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 (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
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
To: HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.)
Reel/Frame 041793/0286 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →
CHANGE OF NAME Recorded Feb 3, 2015
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: HEXION INC.
Reel/Frame 034882/0816 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030146/0970 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 030146/0946 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Mar 28, 2013
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE SPECIALTY CHEMICALS INC. (F/K/A HEXION SPECIALTY CHEMICALS, INC.)
Reel/Frame 030111/0021 →
SECURITY AGREEMENT Recorded Aug 20, 2012
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 028810/0165 →
SECURITY AGREEMENT Recorded Aug 17, 2012
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 028802/0001 →
SECURITY AGREEMENT Recorded Jul 25, 2012
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 028640/0062 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2012
From: SHIRRELL, CHARLES DAVID
To: MOMENTIVE SPECIALTY CHEMICALS INC.
Reel/Frame 028016/0733 →