IP Library Granted Patent US 8,088,881
Granted Patent B2
US 8,088,881 · App. 12/145,871 · Granted Jan 3, 2012

Storage stable melamine-urea-formaldehyde resins and applications thereof

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Quick Facts
Patent No.
US 8,088,881
App. No.
12/145,871
Granted
Jan 3, 2012
Kind
B2
Abstract

Melamine-urea-formaldehyde resins may be prepared using processes including a first cook stage, a second cook stage, and a final addition wherein: the molar ratio of formaldehyde to urea and melamine (F:U+M) in the first cook stage is from about 2.0 to about 5.0; and the molar ratio of formaldehyde to urea and melamine (F:U+M) in the second cook stage is from about 1.5 to 3.0; and the molar ratio of formaldehyde to urea and melamine (F:U+M) in the final addition from about 0.4 to 0.70.

Claims (40)

1. A method for preparing a melamine-urea-formaldehyde resin comprising a first cook stage, a second cook stage, and a final addition wherein:

the first cook stage comprises adding at least formaldehyde and melamine to form a first cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) from about 2.0 to about 5.0;

the second cook stage comprises adding at least urea to form a second cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) from about 1.5 to 3.0; and

the final addition comprises adding at least urea to form a final addition molar ratio of formaldehyde to urea and melamine (F:U+M) from about 0.4 to 0.7.

2. The method of claim 1 wherein the melamine-urea-formaldehyde resin is prepared using formalin.

3. The method of claim 2 wherein the formalin has a formaldehyde concentration of from about 44 to 55 weight percent.

4. The method of claim 1 wherein the melamine-urea-formaldehyde resin is prepared using a urea formaldehyde concentrate.

5. The method of claim 4 wherein the urea formaldehyde concentrate has a formaldehyde concentration of about 60 weight percent and a urea concentration of about 25 weight percent.

6. The method of claim 5 wherein the melamine-urea-formaldehyde resin is prepared using melamine having a particle size of from about 50 to about 400 microns.

7. The method of claim 1 wherein urea is added in the first cook stage and the urea of the first and second cooks stages is divided between the first and second cook stages.

8. The method of claim 1 wherein all of the urea of the first and second cook stages is added in the second cook stage.

9. The method of claim 1 wherein from 75 to 100 weight percent of the formaldehyde added during the first and second cook stages is added during the first cook stage.

10. The method of claim 1 wherein from 60 to 100 weight percent of the melamine added during the first and second cook stages is added during the first cook stage.

11. The method of claim 1 wherein from 0 to 80 weight percent of the urea added during the first and second cook stages is added during the first cook stage.

12. A method for preparing a melamine-urea-formaldehyde resin comprising:

charging formaldehyde and melamine to form a mixture at a first molar ratio of formaldehyde to urea and melamine (F:U+M) from about 2.0 to about 5.0 and then heating the mixture;

charging a first amount of urea to the mixture to form a second molar ratio of formaldehyde to urea and melamine (F:U+M) from about 1.5 to 3.0 and heating the mixture; and

charging a second amount of urea to the mixture to form a third molar ratio of formaldehyde to urea and melamine (F:U+M) from about 0.25 to 1.1.

13. The method of claim 12 , further comprising charging urea with the formaldehyde and melamine to form the mixture.

14. The method of claim 13 , wherein from 75 to 100 weight percent of the formaldehyde, from 60 to 100 weight percent of the melamine and from 0 to 80 weight percent of the urea is added to form the mixture.

15. The method of claim 12 , wherein the first molar ratio of formaldehyde to urea and melamine (F:U+M) is from about 2.5 to about 5.0 and the second molar ratio of formaldehyde to urea and melamine (F:U+M) is from about 1.5 to 2.3.

16. The method of claim 12 , wherein the first molar ratio of formaldehyde to urea and melamine (F:U+M) is from 2.5 to about 5.0 and the second molar ratio of formaldehyde to urea and melamine (F:U+M) is from about 1.5 to less than 2.5.

17. The method of claim 1 , wherein the first cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) is from about 2.5 to about 5.0 and the second cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) is from about 1.5 to 2.3.

18. The method of claim 1 , wherein the first cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) is from 2.5 to about 5.0 and the second cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) is from about 1.5 to less than 2.5.

19. The method of claim 1 , wherein the second cook stage further comprises adding formaldehyde, melamine, or both.

20. The method of claim 1 , wherein the charging the second amount of urea to the mixture comprises charging urea to form a third molar ratio of formaldehyde to urea and melamine (F:U+M) from about 0.33 to about 0.9.

21. A melamine-urea-formaldehyde resin prepared using a method comprising a first cook stage, a second cook stage, and a final addition wherein:

the first cook stage comprises adding at least formaldehyde and melamine to form a first cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) from about 2.0 to about 5.0;

the second cook stage comprises adding at least urea to form a second cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) from about 1.5 to 3.0; and

final addition comprises adding at least urea to form a final addition molar ratio of formaldehyde to urea and melamine (F:U+M) from about 0.4 to 0.7.

22. The melamine-urea-formaldehyde resin of claim 21 wherein the resin is prepared using a formulation further comprising sugar.

23. The melamine-urea-formaldehyde resin of claim 21 further comprising an additive selected from the group consisting of: a mold release agent; a buffering agent; an internal catalyst; a tack modifier; a flow modifier; a fire retardant; and combinations thereof.

24. An article of manufacture comprising a substrate and a melamine-urea-formaldehyde resin wherein:

the substrate is selected from the group consisting of cellulosic-particles, -strands, -fibers, -veneers, and mixtures thereof; the melamine-urea-formaldehyde resin functions to adhere the substrate together into the article of manufacture; and

the melamine-urea-formaldehyde resin is prepared using a method comprising a first cook stage, a second cook stage, and a final addition wherein:

the first cook stage comprises adding at least formaldehyde and melamine to form a first cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) from about 2.0 to about 5.0;

the second cook stage comprises adding at least urea to foam a second cook stage molar ratio of formaldehyde to urea and melamine (F:U+M) from about 1.5 to 3.0; and

the final addition comprises adding at least urea to form a final addition molar ratio of formaldehyde to urea and melamine (F:U+M) from about 0.4 to 0.7.

25. The article of manufacture of claim 24 wherein the article of manufacture is particleboard, hardwood plywood, or medium density fiberboard.

26. The article of manufacture of claim 24 wherein the article of manufacture is particle board.

Assignments (19)
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0823 →
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 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0748 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0842 →
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 →
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 (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 034882/0127 →
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 Apr 15, 2011
From: HEXION SPECIALTY CHEMICALS, INC.
To: MOMENTIVE SPECIALTY CHEMICALS INC.
Reel/Frame 026138/0817 →
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 Jun 25, 2008
From: NO, BYUNG Y.; MOTTER, WILLIAM K.; HARMON, DAVID M.
To: HEXION SPECIALTY CHEMICALS, INC.
Reel/Frame 021150/0046 →