IP Library Granted Patent US 9,388,269
Granted Patent B2
US 9,388,269 · App. 14/202,762 · Granted Jul 12, 2016

Amino-formaldehyde resins and applications thereof

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Quick Facts
Patent No.
US 9,388,269
App. No.
14/202,762
Granted
Jul 12, 2016
Kind
B2
Abstract

Amino-formaldehyde resins, articles of manufacture from the amino-formaldehyde resins, and processes for making the resins and articles are provided herein. In one embodiment, the amino-formaldehyde resins may be prepared using a reaction mixture including formaldehyde, a monohydroxy cyclic compound, and at least one amino compound selected from the group consisting of urea, melamine, and mixtures thereof. In another embodiment, the amino-formaldehyde resins are produced by reacting formaldehyde, a monohydroxy cyclic compound, and at least one amino compound selected from the group consisting of urea, melamine, and mixtures thereof, and the monohydroxy cyclic compound may be added as a front addition, an intermediate addition, a back addition, or a combination thereof, to the reaction mixture of formaldehyde and the at least one amino compound.

Claims (12)

1. An amino-formaldehyde resin prepared using a reaction mixture comprising:

formaldehyde;

a monohydroxy cyclic compound selected from the group of monohydroxy cyclical acetals, monohydroxy cyclical ketals, and combinations thereof; and

at least one amino compound selected from the group consisting of urea, melamine, and mixtures thereof.

2. The amino-formaldehyde resin of claim 1 , wherein the monohydroxy cyclic compound is a monohydroxy heterocyclic compound.

3. The amino-formaldehyde resin of claim 2 , wherein the monohydroxy cyclic compound is selected from the group of glycerol formal, 2,2-dimethyl-1,3-dioxolane-4-methanol, and combinations thereof.

4. The amino-formaldehyde resin of claim 1 , wherein the monohydroxy cyclic compound is present at a concentration from about 0.5 to about 15 weight percent of the reaction mixture.

5. The amino-formaldehyde resin of claim 1 , wherein the reaction mixture further comprises one or more organic compounds.

6. The amino-formaldehyde resin of claim 1 , wherein the amino-formaldehyde resin is an urea-formaldehyde resin, a melamine-formaldehyde resin, a melamineurea-formaldehyde resin, or a combinations thereof.

7. The amino-formaldehyde resin of claim 1 , wherein the amino-formaldehyde resin has surface tension from about 35 mN/m to about 50 mN/m.

8. The amino-formaldehyde resin of claim 1 wherein the amino-formaldehyde resin is prepared by introducing the monohydroxy cyclic compound using a back addition, a front addition, an intermediate addition, or combinations thereof.

9. The amino-formaldehyde resin of claim 1 wherein the monohydroxy cyclic compound is formed by reacting an aldehyde, a ketone, or combinations thereof, with a triol having at least two hydroxyl groups located on adjacent carbon atoms or two hydroxyl groups located on two carbon atoms with one carbon between the two carbon atoms with the hydroxyl groups.

Assignments (15)
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 →
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: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0823 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0842 →
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 →
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 041793/0674 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →
SECURITY INTEREST Recorded Feb 16, 2015
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 034967/0872 →
CHANGE OF NAME Recorded Feb 3, 2015
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: HEXION INC.
Reel/Frame 034882/0127 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 23, 2014
From: LESSMAN, VALTER E.; SABOIA, GILBERTO E.; DA SILVA, CÍCERO L.; CHIPANSKI, EDIELMA D.; HARMON, DAVID M.; NAGARAJAN, RAJAMANI
To: MOMENTIVE SPECIALTY CHEMICALS INC.
Reel/Frame 033015/0560 →
SECURITY INTEREST Recorded Apr 25, 2014
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 032760/0303 →
SECURITY INTEREST Recorded Apr 25, 2014
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 032760/0421 →