IP Library Granted Patent US 8,741,430
Granted Patent B2
US 8,741,430 · App. 12/145,667 · Granted Jun 3, 2014

Storage stable amino-formaldehyde resins and applications thereof

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Quick Facts
Patent No.
US 8,741,430
App. No.
12/145,667
Granted
Jun 3, 2014
Kind
B2
Abstract

Amino-formaldehyde resins may be prepared using formulations including formaldehyde, glycerin and at least one amino compound selected from the group consisting of urea, melamine, and mixtures thereof; under reaction conditions sufficient to prepare a resin, wherein; the amino-formaldehyde resin is prepared in a substantial absence of a sulfonating agent, ethylene glycol, and polyalkylene glycols. If the amino compound is urea, then the urea is present in a molar ratio of formaldehyde to urea ranging from 0.70 to 1.30; if the amino compound is melamine, then the melamine is present in a molar ratio of formaldehyde to melamine ranging from 1.3 to 2.2; and if the amino compound is a mixture of urea and melamine, then the mixture of urea and melamine is present in a molar ratio of formaldehyde to urea and melamine ranging from 0.35 to 1.3.

Claims (32)

1. An amino-formaldehyde resin prepared using a formulation comprising, under condensation reaction conditions, formaldehyde, glycerin and at least one compound selected from the group consisting of urea, melamine, and mixtures thereof; wherein;

the amino-formaldehyde resin is prepared in a substantial absence of a sulfonating agent, ethylene glycol, and polyalkylene glycols;

if the at least one compound is urea, then the urea is present in a final molar ratio of formaldehyde to urea ranging from about 0.70 to about 1.30;

if the at least one compound is melamine, then the melamine is present in a final molar ratio of formaldehyde to melamine ranging from about 1.3 to about 2.2; and

if the at least one compound is a mixture of urea and melamine, then the mixture of urea and melamine is present in a final molar ratio of formaldehyde to urea and melamine ranging from about 0.35 to about 1.3; and wherein;

the amino-formaldehyde resin has improved storage stability, as compared to a conventional resin which has the same final ratio of formaldehyde to amino compounds as the amino-formaldehyde resin but which does not use glycerin in the formulation; and

the amino-formaldehyde resin comprises a glycerin modified amino-formaldehyde resin prepared by introducing the glycerin using a front end addition process.

2. The amino-formaldehyde resin of claim 1 wherein the resin is a UF resin and the urea is present in a final molar ratio of formaldehyde to urea ranging from about 0.70 to about 1.30.

3. The amino-formaldehyde resin of claim 2 wherein the resin is a UF resin and the urea is present in a final molar ratio of formaldehyde to urea of about 1.15.

4. The amino-formaldehyde resin of claim 2 wherein the resin is a UF resin and the glycerin is present at a concentration of about 6 weight percent of the formulation.

5. The amino-formaldehyde resin of claim 1 wherein the resin is a MF resin and the melamine is present in a final molar ratio of formaldehyde to melamine ranging from about 1.3 to about 2.2.

6. The amino-formaldehyde resin of claim 5 wherein the resin is a MF resin and the melamine is present in a final molar ratio of formaldehyde to melamine of about 1.7.

7. The amino-formaldehyde resin of claim 5 wherein the resin is a MF resin and the glycerin is present at a concentration of about 15 weight percent of the formulation.

8. The amino-formaldehyde resin of claim 1 wherein the resin is a MUF resin and the mixture of urea and melamine is present in a final molar ratio of formaldehyde to urea and melamine ranging from about 0.35 to about 1.3.

9. The amino-formaldehyde resin of claim 8 wherein the resin is a MUF resin and the mixture of urea and melamine is present in a final molar ratio of formaldehyde to urea and melamine of about 0.65.

10. The amino-formaldehyde resin of claim 8 wherein the resin is a MUF resin and the glycerin is present at a concentration of about 15 weight percent of the formulation.

11. The amino-formaldehyde resin of claim 1 wherein the amino-formaldehyde resin is a UF or a MUF resin and the UF or MUF resin is prepared using a formaldehyde urea concentrate.

12. The amino-formaldehyde resin of claim 1 wherein the amino-formaldehyde resin is a MF or a MUF resin and the MF or MUF resin is prepared using melamine having a particle size of from about 50 to 400 microns.

13. The amino-formaldehyde resin of claim 1 wherein the resin is a UF or a MUF resin and the UF or MUF resin is prepared using an urea having a purity of about 98 percent.

14. A process for preparing an amino-formaldehyde resin comprising combining under condensation reaction conditions formaldehyde, glycerin, and at least one compound selected from the group consisting of urea, melamine, and mixtures thereof; wherein;

the amino-formaldehyde resin is prepared in a substantial absence of a sulfonating agent, ethylene glycol, and polyalkylene glycols;

if the at least one compound is urea, then the urea is present in a final molar ratio of formaldehyde to urea ranging from about 0.70 to about 1.30;

if the at least one compound is melamine, then the melamine is present in a final molar ratio of formaldehyde to melamine ranging from about 1.3 to about 2.2; and

if the at least one compound is a mixture of urea and melamine, then the mixture of urea and melamine is present in a final molar ratio of formaldehyde to urea and melamine ranging from about 0.35 to about 1.3; and wherein;

the amino-formaldehyde resin has improved storage stability, as compared to a conventional resin which has the same final ratio of formaldehyde to amino compounds as the amino-formaldehyde resin but which does not use glycerin in the formulation; and

the amino-formaldehyde resin comprises a glycerin modified amino-formaldehyde resin prepared by introducing the glycerin using a front end addition process.

15. An article of manufacture comprising a substrate and an amino-formaldehyde resin wherein:

the substrate is in a form selected from the group consisting of cellulosic:

-particles, -strands, -fibers, -veneers, and mixtures thereof;

the amino-formaldehyde resin functions to adhere the substrate together into or within the article of manufacture; and

the amino-formaldehyde resin is prepared using the formulation of claim 1 .

16. The article of manufacture of claim 15 wherein the article of manufacture is particle board.

Assignments (11)
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 →