IP Library Granted Patent US 12,049,536
Granted Patent B2
US 12,049,536 · App. 17/639,453 · Granted Jul 30, 2024

Tris (hydroxymethyl) phosphine oxide based polyester polyol and a resin composition obtained therefrom

Inventors: Zhenghe Zhang (Shanghai, CN); Fan Xie (Shanghai, CN); Hualiang Zhong (Shanghai, CN); Yuefan Zhang (Shanghai, CN)
Assignee: HUNTSMAN INTERNATIONAL LLC
C08G18/4684C07F9/091C08G18/7664C08G2110/0025
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Quick Facts
Patent No.
US 12,049,536
App. No.
17/639,453
Granted
Jul 30, 2024
Kind
B2
Abstract

This disclosure generally provides tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compounds and resin compositions made therefrom which have improved flammability, wherein the resin composition comprising: (a) a polyfunctional isocyanate; (b) an isocyanate reactive composition comprising (b1) a polyfunctional polyol composition and a catalyst composition; and optionally (b2) a polyfunctional amine; wherein the polyfunctional polyol composition comprises tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound.

Claims (37)

1. A tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound having the formula (I):

wherein

R 1 is selected from a combination of linear, branched, saturated, unsaturated, cyclic and/or non-cyclic carbon chains, aliphatic hydrocarbons, araliphatic hydrocarbons, aromatic hydrocarbons and combinations thereof, optionally interrupted by one or more oxygen atoms, nitrogen atoms and/or sulphur atoms, and optionally comprising any functional group selected from hydroxy, ether, halogen, carbonyl, and/or carboxyl groups and combinations thereof;

n is in a range of from 1 to 25;

m is in a range of from 0 to 25; and

R 2 is a hydrogenated triazine group or derivative thereof.

2. The tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound of claim 1 , wherein n is in a range of from 1 to 3.

3. The tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound of claim 1 , wherein m is in a range of from 1 to 3.

4. The tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound of claim 1 , wherein each R 1 is an alkyl group.

5. The tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound of claim 1 , wherein the molecular weight of the polyfunctional polyol is in an amount ranging from about 100 to about 1500.

6. A resin composition comprising:

(a) a polyfunctional isocyanate; and

(b) an isocyanate reactive composition comprising

(b1) a polyfunctional polyol composition and a catalyst composition; and optionally

(b2) a polyfunctional amine;

wherein the polyfunctional polyol composition comprises the tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound of claim 1 .

7. The resin composition of claim 6 , wherein the resin composition has a NCO index in the range from about 0.7 to about 5.

8. The resin composition of claim 6 , wherein the polyfunctional isocyanate is a polymeric MDI or an MDI isomer mixture or a mixture thereof.

9. The resin composition of claim 6 , wherein the catalyst composition comprises an amine catalyst and/or a trimerization catalyst.

10. The resin composition of claim 6 , wherein the polyfunctional amine (b2) is a polyetheramine.

11. A process for making a resin composition comprising adding an isocyanate reactive composition to a polyfunctional isocyanate, wherein the isocyanate reactive composition comprises:

a polyfunctional polyol composition and a catalyst composition; and optionally

a polyfunctional amine;

wherein the polyfunctional polyol composition comprises a tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound having the formula (I):

wherein

R 1 is selected from a combination of linear, branched, saturated, unsaturated, cyclic and/or non-cyclic carbon chains, aliphatic hydrocarbons, araliphatic hydrocarbons, aromatic hydrocarbons and combinations thereof, optionally interrupted by one or more oxygen atoms, nitrogen atoms and/or sulphur atoms, and optionally comprising any functional group selected from hydroxy, ether, halogen, carbonyl, and/or carboxyl groups and combinations thereof;

n is in a range of from 1 to 25; and

m is in a range of from 0 to 25; and

R 2 is a hydrogenated triazine group or derivative thereof.

12. A rigid foam product prepared from the resin composition of claim 6 .

13. A tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound having the formula (III):

14. A resin composition comprising:

(a) a polyfunctional isocyanate; and

(b) an isocyanate reactive composition comprising

(b1) a polyfunctional polyol composition and a catalyst composition; and optionally

(b2) a polyfunctional amine;

wherein the polyfunctional polyol composition comprises the tris (hydroxymethyl) phosphine oxide based polyfunctional polyester polyol compound of claim 13 .

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 →
CORRECTIVE ASSIGNMENT TO CORRECT THE TITLE OF APPLICATION PREVIOUSLY RECORDED AT REEL: 061911 FRAME: 0181. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Jan 5, 2023
From: ZHANG, ZHENGHE; XIE, FAN; ZHONG, HUALIANG; ZHANG, YUEFAN
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 062326/0691 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2022
From: ZHANG, ZHENGHE; XIE, FAN; ZHONG, HUALIANG; ZHANG, YUEFAN
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 061911/0181 →
Priority Claims (1)
WO PCT/CN2019/105705 · Sep 12, 2019 · international
Continuity (1)
Related Publication 20220356294A1 · Nov 10, 2022