IP Library Granted Patent US 8,980,774
Granted Patent B2
US 8,980,774 · App. 13/524,828 · Granted Mar 17, 2015

Compositions and methods for making polyesters and articles therefrom

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Quick Facts
Patent No.
US 8,980,774
App. No.
13/524,828
Granted
Mar 17, 2015
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 (33)

1. A binder material prepared using a formulation comprising:

a polyester material formed from at least one organic acid having three carboxylic groups and at least one multi-hydroxyl alcohol having three hydroxyl groups;

a cross-linking agent comprising an acrylic polymer; and

a vinyl alcohol containing polymer, wherein the binder material is free of formaldehyde.

2. The binder material of claim 1 , wherein the formulation further comprises a formaldehyde-free aldehyde compound.

3. The binder material of claim 1 , wherein the vinyl alcohol containing polymer comprises from about 0.1 wt. % to about 20 wt. % of the formulation.

4. The binder material 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 binder material of claim 1 , wherein the acrylic polymer comprises from about 0.1 wt. % to about 50 wt. % of the formulation.

6. The binder material of claim 2 , wherein the formaldehyde-free aldehyde compound comprises from about 0.1 wt. % to about 10 wt. % of the formulation.

7. The binder material of claim 1 , wherein vinyl alcohol containing polymer comprises polyvinyl alcohol, a derivative thereof or a co-polymer thereof.

8. The binder material of claim 2 , wherein the formaldehyde-free aldehyde compound is selected from the group consisting of glyoxal, glutaraldehyde compound, and combinations thereof.

9. The binder material of claim 1 , wherein the polyester material is water-soluble.

10. The binder material of claim 1 , wherein the at least one organic acid having three carboxylic groups comprises citric acid.

11. The binder material of claim 1 , wherein the at least one multi-hydroxyl alcohol having three hydroxyl groups is selected from the group consisting of glycerol, trimethylolpropane, trimethyolethane, and combinations thereof.

12. The binder material of claim 1 , wherein the molar ratio of at least one organic acid to at least one multi-hydroxyl alcohol is from 1:3 to 3:1.

13. An article of manufacture comprising:

a substrate; and

a binder material, wherein:

the substrate comprises a fibrous material selected from the group consisting of glass fibers, mineral fibers (mineral wool), polyester fibers, cellulose materials, and combinations thereof;

the binder material functions to adhere the substrate together into or within the article of manufacture; and

the binder material is prepared using a formulation comprising:

a polyester material formed from at least one organic acid containing three carboxylic groups and at least one multi-hydroxyl alcohol containing three hydroxyl groups; and

a cross-linking agent comprising an acrylic polymer; and

a vinyl alcohol containing polymer, wherein the binder material is free of formaldehyde.

14. The article of claim 13 , wherein the binder material is prepared using a formulation further comprising a formaldehyde-free aldehyde compound.

15. The article of claim 13 , wherein the article of manufacture has a dry tensile strength from 40 lbf/1.5 inch to 100 lbf/1.5 inch.

16. The article of claim 13 , wherein the article of manufacture has a wet tensile strength from 3 lbf/1.5 inch to 70 lbf/1.5 inch.

17. The article of claim 13 , wherein the fibrous material comprise from about 70 wt. % to about 95 wt. % of the article of manufacture.

18. The binder material of claim 1 , wherein the polyester material is a self-crosslinkable polyester material.

19. The article of claim 13 , wherein the polyester material is a self-crosslinkable polyester material.

20. The article of claim 13 , wherein the vinyl alcohol containing polymer comprises from about 0.1 wt. % to about 20 wt. % of the formulation.

21. The article of claim 13 , wherein the vinyl alcohol containing polymer comprises polyvinyl alcohol, a derivative thereof or a co-polymer thereof.

22. The article of claim 14 , wherein the formaldehyde-free aldehyde compound comprises from about 0.1 wt. % to about 10 wt. % of the formulation.

Assignments (26)
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.
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 →
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 056219/0582 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0677 →
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
To: HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.)
Reel/Frame 041793/0286 →
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: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030146/0970 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 030146/0946 →
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 →
SECURITY AGREEMENT Recorded Aug 20, 2012
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 028810/0165 →
SECURITY AGREEMENT Recorded Aug 17, 2012
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 028802/0001 →
SECURITY AGREEMENT Recorded Jul 25, 2012
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 028640/0062 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2012
From: ZHANG, YINGCHAO; SUBRAYAN, RAMAN C.; MALHOTRA, VINAY; SNOVER, DAVID A.
To: MOMENTIVE SPECIALTY CHEMICALS INC.
Reel/Frame 028470/0788 →