IP Library Granted Patent US 9,809,674
Granted Patent B2
US 9,809,674 · App. 14/391,013 · Granted Nov 7, 2017

High functional polyester polyols

Inventor: David J. Shieh (Sugarland, TX)
Assignee: HUNTSMAN INTERNATIONAL LLC
C08G18/4219C08G18/14C08G18/381C08G18/4018C08G18/4208C08G18/4288C08G18/4829C08G18/6633C08G18/72C08G63/12C08G63/183C08G63/916C08J9/143C08G2101/00C08G2101/005C08J2201/022C08J2375/08Y02P20/127
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Quick Facts
Patent No.
US 9,809,674
App. No.
14/391,013
Granted
Nov 7, 2017
Kind
B2
Abstract

Aromatic polyester polyols with high functionality, moderate viscosity, and high aromatic content suitable as the sole polyol in the production of polyurethane foams without the use of any polyether polyols are disclosed. This unique combination of properties makes them suit for use as the sole polyol in the production of polyurethane foams. With reduction of flame retardants, these foams based on sole aromatic polyol can have E-84 class one fire properties. The aromatic polyester polyols of this invention are characterized as having a functionality of greater than 2.8 while having a moderate viscosity ranging from 4,000-10,000 cps @ 25 C. A typical high functional polyester polyol of the present invention has a hydroxyl number in the range of 320-400, viscosity of 4,000-10,000 cps @ 25 C, functionality of greater than 2.8 and percent phenyl content greater than 14.75.

Claims (20)

1. An aromatic polyester polyol, suitable as the sole polyol in the production of polyurethane foams that have an E-84 tunnel fire test class one rating, said aromatic polyester polyol having a functionality range from 2.8 to 3.2 and a moderate viscosity ranging from 4,000-10,000 cps @ 25° C. inclusive, wherein said polyol is prepared by the transesterification or esterification of a mixture comprising:

46.9-66% w/w of a glycol,

24-34% w/w of a terephthalate source,

5.02-17% w/w glycerin,

0-14% w/w pentaerythritol,

0-5% w/w methyl glucoside,

0-10% w/w sorbitol,

0-15% w/w of a natural vegetable oil, modified natural vegetable oil or fatty acid derivative of vegetable oil.

2. The aromatic polyester polyol of claim 1 wherein the glycol is ethylene glycol, polyethylene glycol, propylene glycol, or polypropylene glycol.

3. The aromatic polyester polyol of claim 1 wherein the terephthalate source is polyethylene terephthalate (PET), industrial recycled PET, post-consumer PET, terephthalic acid (TA), industrial recycled TA (BACA), phthalic anhydride, iso-phthalic acid or meta-phthalic acid.

4. The aromatic polyester polyol of claim 1 wherein the mixture comprises the natural vegetable oil or the fatty acid derivative of vegetable oil wherein the natural vegetable oil is castor oil, palm oil, cotton oil, soybean oil, epoxidized soybean oil, corn oil, tall oil, linseed oil, epoxidized linseed oil, tung oil, or tofu oil, or the fatty acid derivative of vegetable oil is a fatty acid derivative of castor oil, palm oil, cotton oil, soybean oil, corn oil, tall oil, linseed oil, tung oil, or tofu oil.

5. The aromatic polyester polyol of claim 1 further characterized as having a hydroxyl number in the range of 320-400 inclusive and percent phenyl content w/w in the range of 14.75 to 19.58.

6. A composition for preparing polyurethane foam comprising: an A-side component comprising polyisocyanate; and a B-side component comprising catalyst, surfactant, flame retardant, blowing agent and in major part a polyol component consisting essentially of the aromatic polyester polyol according to claim 1 and essentially free of polyether polyol.

7. The composition of claim 6 wherein the polyol component is 65-80% w/w of the B-side component.

8. The composition of claim 6 wherein the volume ratio of A-side component to B-side component is 1:1.

9. The composition of claim 6 wherein the blowing agent is water, pentafluoropropane, pentafluorobutane, heptafluoropropane, chloro-trifluoropropane, hexafluoro-2-butene, pentanes or combinations thereof.

10. A polyurethane foam comprising the reaction product of the composition according to claim 6 .

11. A method of applying a polyurethane foam comprising the steps of: providing an A-side component comprising polyisocyanate and a B-side component comprising catalyst, surfactant, flame retardant, blowing agent and in major part a polyol component consisting essentially of the aromatic polyester polyol according to claim 1 and essentially free of polyether polyol, preparing a surface on which to apply the foam; reacting the A-side and B-side components; and applying the reacting components to a surface.

12. The method of claim 11 wherein said surface comprises a roof, a structural wall, an insulated cavity, a storage tank or a process vessel.

13. The aromatic polyester polyol of claim 1 , wherein the glycerin is a biodiesel recycled crude glycerin.

Assignments (4)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2014
From: SHIEH, DAVID J.
To: OXID L.P.
Reel/Frame 033898/0655 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2014
From: OXID L.P.
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 033898/0693 →
Continuity (2)
Provisional Application 61622293 · Apr 10, 2012
Related Publication 20150051304A1 · Feb 19, 2015