IP Library Granted Patent US 7,989,575
Granted Patent B2
US 7,989,575 · App. 11/956,662 · Granted Aug 2, 2011

Phenol-formaldehyde resole resins, method of manufacture, methods of use, and articles formed therefrom

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,989,575
App. No.
11/956,662
Granted
Aug 2, 2011
Kind
B2
Abstract

A composition is disclosed, which comprises a hydroxyaromatic-aldehyde resole resin comprising an aldehyde and a hydroxyaromatic compound, modified with a urea-aldehyde condensate. The hydroxyaromatic-aldehyde resole resin is prepared without ammonia or a primary amine and the composition does not contain a triazone or a substituted triazone compound. The composition has improved premix stability, improved cure efficiency, comparable tensile strength, and lower volatiles than the hydroxyaromatic-aldehyde resole resin unmodified with a urea-aldehyde condensate. Also disclosed are articles prepared therefrom.

Claims (20)

1. A composition comprising a hydroxyaromatic-aldehyde resole resin comprising the reaction product of an aldehyde and a hydroxyaromatic compound, modified with a urea-aldehyde condensate wherein the urea-aldehyde condensate is substantially free of a triazone compound.

2. The composition of claim 1 , having an initial aldehyde to hydroxyaromatic compound molar ratio of about 2.0:1 to about 6.0:1 before combining the hydroxyaromatic-aldehyde resole resin with the urea-aldehyde condensate; and a final free formaldehyde content of about 1% to about 18% by weight of solids in the composition after combining, wherein the composition has a solids content of about 45 to about 50%.

3. The composition of claim 2 having an unreacted hydroxyaromatic compound content of less than about 1% by weight of solids in the composition.

4. The composition of claim 1 wherein the hydroxyaromatic-aldehyde resole resin is modified with about 1 to about 40% by weight of solids of a urea-aldehyde condensate.

5. The composition of claim 1 wherein the hydroxyaromatic-aldehyde resole resin is a phenol-formaldehyde resole resin.

6. The composition of claim 1 wherein the urea-aldehyde condensate is a urea-formaldehyde condensate.

7. The composition of claim 1 , wherein a premix comprising the composition remains free of visible haze for greater than 36 hours at a temperature of about 9 to about 10° C. and with no precipitate forming for at least 72 hours.

8. The composition of claim 1 , wherein a premix comprising the composition remains free of visible haze for greater than about 48 hours at a temperature of about 22° C. to about 27° C.

9. The composition of claim 1 , further comprising fibers.

10. The composition of claim 9 , wherein the fibers are glass fibers.

11. The composition of claim 9 , wherein the composition comprises an insulation product.

12. A method of making modified hydroxyaromatic-aldehyde resole resin, comprising combining a urea-aldehyde condensate, substantially free of a triazone compound, with a hydroxyaromatic-aldehyde resole resin, at a time prior to the use of the modified hydroxyaromatic-aldehyde resole resin in a process for the manufacture of an article therefrom.

13. The method of claim 12 , wherein a substituted nitrogen compound is added to the hydroxyaromatic-aldehyde resole resin.

14. The method of claim 12 wherein the urea-aldehyde condensate is urea-formaldehyde condensate, and wherein the hydroxyaromatic-aldehyde resole resin is a phenol-formaldehyde resole resin.

15. The method of claim 13 , wherein the substituted nitrogen compound comprises melamine, urea, dicyandiamide, ethyleneurea, propyleneurea, trimethyleneurea, glycouril, or a combination comprising at least one of the foregoing.

16. The method of claim 13 , wherein the urea-aldehyde condensate is added to the hydroxyaromatic-aldehyde resole resin after the substituted nitrogen compound has been added to the hydroxyaromatic-aldehyde resole resin.

17. A method of manufacture of an article, comprising contacting a composition comprising a hydroxyaromatic-aldehyde resole resin modified with a urea-aldehyde condensate which is substantially free of a triazone compound, to fibers; and curing the composition.

18. The method of claim 17 wherein the fibers are glass fibers.

19. The method of claim 18 wherein the article is an insulation product.

20. An article comprising fibers and a cured hydroxyaromatic-aldehyde resole resin that has been modified with a urea-aldehyde condensate which condensate is substantially free of a triazone compound.

Assignments (28)
ASSIGNMENT OF PATENT AND TRADEMARK SECURITY INTEREST Recorded May 12, 2025
From: MACQUARIE CAPITAL FUNDING LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071276/0379 →
SECURITY INTEREST Recorded May 12, 2025
From: BAKELITE CHEMICALS LLC; BAKELITE UK HOLDING LTD.; BAKELITE GMBH; BAKELITE SYNTHETICS UK
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071090/0740 →
SECURITY INTEREST Recorded Jan 23, 2025
From: BAKELITE CHEMICALS LLC; BAKELITE UK HOLDING LTD.; BAKELITE GMBH; BAKELITE SYNTHETICS UK LIMITED
To: GOLDMAN SACHS BANK USA
Reel/Frame 069981/0468 →
RELEASE OF SECURITY INTEREST Recorded Jun 15, 2022
From: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P.
To: HEXION VAD LLC
Reel/Frame 060209/0558 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.
To: MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0327 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.; SURFACE TECH LLC
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0250 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2022
From: BAKELITE LLC
To: BAKELITE UK HOLDING LTD.
Reel/Frame 060377/0699 →
CHANGE OF NAME Recorded May 3, 2022
From: HEXION VAD LLC
To: BAKELITE LLC
Reel/Frame 059926/0973 →
RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) RECORDED AT REEL/FRAME 049741/0425 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0473 →
RELEASE OF SECURITY INTEREST IN PATENTS (ABL) RECORDED AT REEL/FRAME 049740/0770 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0490 →
PARTIAL RELEASE OF SECURITY INTEREST Recorded Nov 3, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 058577/0201 →
PARTIAL RELEASE OF SECURITY INTEREST Recorded Nov 3, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 058796/0363 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2021
From: HEXION INC.
To: HEXION VAD LLC
Reel/Frame 057323/0086 →
SECURITY INTEREST Recorded May 5, 2021
From: HEXION VAD LLC
To: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P., AS COLLATERAL AGENT
Reel/Frame 056145/0957 →
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 →
CHANGE OF NAME Recorded Feb 3, 2015
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: HEXION INC.
Reel/Frame 034882/0280 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 030146/0946 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030146/0970 →
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 →
CHANGE OF NAME Recorded Aug 3, 2011
From: HEXION SPECIALTY CHEMICALS, INC.
To: MOMENTIVE SPECIALTY CHEMICALS INC.
Reel/Frame 026693/0854 →
SECURITY AGREEMENT Recorded Feb 5, 2010
From: HEXION LLC; HEXION SPECIALTY CHEMICALS, INC.; BORDEN CHEMICAL FOUNDRY, LLC; BORDEN CHEMICAL INVESTMENTS, INC.; HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; BORDEN CHEMICAL INTERNATIONAL, INC.; OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 023905/0451 →
SECURITY INTEREST Recorded Jan 29, 2010
From: HEXION SPECIALTY CHEMICALS, INC.; BORDEN CHEMICAL FOUNDRY, LLC; BORDEN CHEMICAL INVESTMENTS, INC.; HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; BORDEN CHEMICAL INTERNATIONAL, INC.; OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
To: WILMINGTON TRUST FSB, AS COLLATERAL AGENT
Reel/Frame 023963/0038 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2007
From: ARBUCKLE, STEPHEN W.
To: HEXION SPECIALTY CHEMICALS, INC.
Reel/Frame 020248/0495 →