IP Library Granted Patent US 9,550,894
Granted Patent B2
US 9,550,894 · App. 14/610,852 · Granted Jan 24, 2017

Compositions and methods for making polyesters and articles therefrom

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Quick Facts
Patent No.
US 9,550,894
App. No.
14/610,852
Granted
Jan 24, 2017
Kind
B2
Abstract

Polyester materials, methods for making polyesters materials, and uses of the polyester materials in binder materials and articles of manufacture are disclosed. In one embodiment, a process is provided for preparing a polyester solution, including mixing monomers of at least one organic acid containing at least three carboxylic groups and at least one multi-hydroxyl alcohol containing at least three hydroxyl groups to form a reaction mixture, heating the reaction mixture to a first temperature, polymerizing the monomers at the first temperature until reaching an acid value from about 200 to about 400 mg KOH/g, adjusting the temperature to a second temperature less than the first temperature, and forming the polyester solution. The polyester materials may be mixed with cross-linking materials to form binder materials. The binder material may then be used to form articles of manufacture.

Claims (20)

1. A process for forming a binder material, comprising:

forming a polyester solution, comprising:

mixing monomers of at least one organic acid containing at least three carboxylic groups and at least one multi-hydroxyl alcohol containing at least three hydroxyl groups;

heating the reaction mixture to a first temperature;

polymerizing the monomers at the first temperature until reaching an acid value from about 200 to about 400 mg KOH/g; and

adjusting the temperature to a second temperature less than the first temperature;

adding a vinyl alcohol containing polymer to the reaction mixture; and

adding a cross-linking agent comprising an acrylic polymer, wherein the binder material is free of formaldehyde.

2. The process of claim 1 , wherein the cross-linking agent further comprises an aldehyde compound.

3. The process of claim 2 , wherein the aldehyde compound is a formaldehyde-free aldehyde component selected from the group consisting of glyoxal, glutaraldehyde compound, and combinations thereof.

4. The process of claim 1 , wherein the acrylic polymer is selected from the group consisting of polyacrylic acid, polyacrylic ether polymer, polyacrylic ester polymer, polyacrylic amide polymer, and combinations thereof.

5. The process of claim 1 , wherein vinyl alcohol containing polymer comprises polyvinyl alcohol, a derivative thereof or a co-polymer thereof.

6. The process of claim 3 , wherein polyester material is water-soluble.

7. The process of claim 1 , wherein the at least one organic acid having three carboxylic groups comprises citric acid and the at least one multi-hydroxyl alcohol having three hydroxyl groups is selected from the group consisting of glycerol, trimethylolpropane, trimethyolethane, and combinations thereof.

8. The process of claim 1 , wherein the ratio of at least one organic acid to at least one multi-hydroxyl alcohol is from 1:3 to 3:1.

9. The process of claim 1 , further comprising adding the binder material to a substrate and then curing the substrate.

10. The process of claim 9 , wherein the curing the substrate comprises a curing process from about 1 to about 6 minutes at a temperature from about 350° F. to about 450° F.

11. The process of claim 10 , wherein the wet web strength of the binder and substrate is from about 180 g to about 400 g, before the curing the substrate.

12. The process of claim 1 , wherein the acid value is from about 200 to about 300 mg KOH/g.

13. The process of claim 1 , wherein the acid value is from about 200 to about 250 mg KOH/g.

Assignments (21)
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 →
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 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.; SURFACE TECH LLC
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0250 →
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 →
CHANGE OF NAME Recorded May 3, 2022
From: HEXION VAD LLC
To: BAKELITE LLC
Reel/Frame 059926/0973 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2022
From: BAKELITE LLC
To: BAKELITE UK HOLDING LTD.
Reel/Frame 060377/0699 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2021
From: HEXION INC.
To: HEXION VAD LLC
Reel/Frame 057323/0086 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0677 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0582 →
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 →
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.
Reel/Frame 041793/0920 →
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 2, 2016
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 037639/0795 →
SECURITY INTEREST Recorded Jun 8, 2015
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 035801/0372 →
SECURITY INTEREST Recorded Jun 8, 2015
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 035848/0705 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2015
From: ZHANG, YINGCHAO; SUBRAYAN, RAMAN C.; MALHOTRA, VINAY; SNOVER, DAVID A.
To: HEXION INC.
Reel/Frame 034894/0138 →