IP Library Granted Patent US 7,560,526
Granted Patent B2
US 7,560,526 · App. 11/725,991 · Granted Jul 14, 2009

Polyol with high cyclopentane solubility

Assignee: Oxid, L.P.
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Quick Facts
Patent No.
US 7,560,526
App. No.
11/725,991
Granted
Jul 14, 2009
Kind
B2
Abstract

Methods and compositions for forming polyurethane foam. A method for manufacturing an aromatic polyester polyol comprises heating a glycol, a dicarboxylic acid or ester, functionality enhancing agent, and a natural oil to about 480° F. to form a reaction product, allowing the reaction product to cool to about 140° F., and adding additional glycol to form an aromatic polyester polyol composition, wherein the total glycol comprises less than about 36 weight percent of the polyol composition. An aromatic polyester polyol composition comprises a glycol, a dicarboxylic acid or ester, functionality enhancing agent, and a natural oil, wherein the total glycol comprises less than about 36 weight percent of the aromatic polyester polyol composition. An aromatic polyester polyol composition comprising a cyclopentane solubility of at least about 25 percent, a hydroxyl number of at least about 150, the natural oil comprising less than about 25 weight percent, and/or the dicarboxylic acid or ester comprising more than about 29 weight percent of the polyol composition.

Claims (30)

1. A method for manufacturing an aromatic polyester polyol, comprising:

heating a glycol, a dicarboxylic acid or ester, functionality enhancing agent, and a natural oil to about 460° F.—about 480° F. to form a reaction product;

allowing the reaction product to cool to about 140° F.; and

adding additional glycol to form an aromatic polyester polyol composition, wherein the total glycol comprises less than about 36 weight percent of the polyol composition,

wherein the natural oil comprises less than about 25 weight percent of the polyol composition and

wherein the aromatic polyester polyol has a cyclopentane solubility of greater than 25%.

2. The method of claim 1 , wherein the dicarboxylic acid or ester comprises more than about 29 weight percent of the polyol composition.

3. The method of claim 1 , wherein the glycol is diethylene glycol, triethylene glycol, tetraethylene glycol, or combinations thereof.

4. The method of claim 1 , wherein the dicarboxylic acid or ester is terephthalic acid, phthalic anhydride, polyethylene terephthalate (PET), a byproduct of aromatic carboxylic acid (BACA) or combinations thereof.

5. The method of claim 1 , wherein the functionality enhancing agent is sorbitol, pentaerythritol, corpent, glycerin, or combinations thereof.

6. The method of claim 1 , wherein the natural oil is corn oil, soybean oil, or combinations thereof.

7. An aromatic polyester-polyol composition, comprising:

an aromatic polyester polyol reaction product formed by the method of claim 1 .

8. The composition of claim 7 , wherein the aromatic polyester polyol has a hydroxyl number of at least about 150.

9. The composition of claim 7 , further comprising an aromatic acid content of about 30 to about 40 weight percent.

10. The composition of claim 7 further comprising a hydrocarbon blowing agent having a concentration of about 25 percent of the polyol composition.

11. The composition of claim 10 , wherein the hydrocarbon blowing agent is pentane, cyclopentane, isopentane, or a combination thereof.

12. The method of claim 1 , wherein the concentration of the natural oil is from about 16 to about 23 weight percent of the polyol composition.

13. A method for manufacturing an aromatic polyester polyol, comprising:

heating a glycol, a dicarboxylic acid or ester, functionality enhancing agent, and a natural oil to about 460° F.—about 480° F. to form a reaction product;

allowing the reaction product to cool to about 140° F.; and

adding additional glycol to form an aromatic polyester polyol composition having a hydroxyl number of at least about 150.

14. The method of claim 13 wherein the aromatic polyester polyol composition has a cyclopentane solubility of greater than 25%.

15. The method of claim 13 , wherein the natural oil comprises between about 16 wt. % to about 25 wt. % of the aromatic polyester polyol composition.

16. The method of claim 13 , wherein the glycol comprises less than about 36 wt. % of the aromatic polyester polyol composition.

17. An aromatic polyester-polyol composition, comprising:

an aromatic polyester polyol reaction product formed by the method of claim 13 .

18. The composition of claim 17 , wherein the aromatic polyester polyol reaction product has a cyclopentane solubility of greater than about 25%.

19. The composition of claim 17 , wherein the natural oil comprises between about 16 wt. % to about 25 wt. % of the aromatic polyester polyol reaction product.

20. The composition of claim 17 , wherein the glycol comprises less than about 36 wt. % of the aromatic polyester polyol reaction product.

Assignments (6)
SECURITY INTEREST Recorded May 4, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCOMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK N.A.
Reel/Frame 075498/0663 →
PATENT SECURITY AGREEMENT Recorded Mar 10, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCAMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK, N.A.
Reel/Frame 075106/0238 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN UNITED STATES TRADEMARKS AND PATENTS Recorded Jun 13, 2018
From: JPMORGAN CHASE BANK, N.A.
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 046355/0306 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2017
From: OXID LP
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 040868/0863 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2013
From: OXID L.P.
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 031265/0567 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2007
From: SHIEH, DAVID J.
To: OXID, L.P.
Reel/Frame 019230/0178 →
Continuity (2)
Provisional Application 6078441100 · Mar 21, 2006
Related Publication 20070225392A1 · Sep 27, 2007