IP Library Granted Patent US 12,600,813
Granted Patent B2
US 12,600,813 · App. 18/599,966 · Granted Apr 14, 2026

Polyurethane insulation foam composition comprising a stabilizing compound

Inventors: Yangjun Cai (The Woodlands, TX); Lifeng Wu (The Woodlands, TX); Sachchida Singh (The Woodlands, TX); Yun-Shan Liu (The Woodlands, TX)
C08G18/5057C08G18/1833C08G18/3206C08G18/482C08G18/4829C08G18/6611C08G18/7664C08J9/125C08G2110/0025C08G2110/005C08J2375/08
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Quick Facts
Patent No.
US 12,600,813
App. No.
18/599,966
Granted
Apr 14, 2026
Kind
B2
Abstract

A polyurethane insulation foam composition is disclosed herein. The polyurethane insulation foam comprises: (i) an aromatic isocyanate compound; (ii) an isocyanate reactive compound; (iii) water; (iv) a tertiary amine compound; (v) a hydrophilic carboxylic acid compound; (vi) a halogenated olefin compound; (vii) a stabilizing compound, and (vii) optionally, other additives.

Claims (73)

1 . A method of making a rigid polyurethane foam product from a polyurethane insulation foam composition comprising:

reacting one or more of the following reactive ingredients of the polyurethane insulation foam composition to form the rigid polyurethane foam product:

(i) an aromatic isocyanate compound;

(ii) an isocyanate reactive compound;

(iii) water;

(iv) a tertiary amine compound;

(v) a hydrophilic carboxylic acid compound selected from a monocarboxylic acid or a monocarboxylic acid blended with at least one compound selected from a hydroxyl-carboxylic acid, a hydroxyl-polycarboxylic acid, and an AGS acid;

(vi) a halogenated olefin blowing agent; and

(vii) a stabilizing compound wherein the stabilizing compound comprises an un-alkoxylated polyhydroxy compound having 4 or more hydroxyl groups;

(viii) optionally, other additives;

wherein Component (v) is present in the polyurethane insulation foam composition in an amount ranging from 0.2 to 4 equivalents of carboxyl group per equivalent of tertiary amines in Component (iv) and Component (vii) is present in an amount of less than 0.8 moles per mole of Component (v);

wherein a CT REACTIVITY SHIFT of the polyurethane insulation foam composition is less than or equal to 20 and a TFT REACTIVITY SHIFT is less than or equal to 4; and wherein the CT REACTIVITY SHIFT and the TFT REACTIVITY SHIFT of the polyurethane insulation foam composition is determined by using Formulas X and Y, respectively:

CT

REACTIVE

SHIFT

=

100

*

[

(

CT

79

-

CT

0

)

/

CT

0

]

Formula

X

wherein

CT 79 means a composition's CT as determined using the FOAM REACTIVITY TEST after the composition's B-Side comprising Components (ii) and (iii) has been aged at 40° C. in a closed, pressure-rated, glass container that was placed in an oven for 79 days,

CT 0 means a composition's CT as determined using the FOAM REACTIVITY TEST after the composition's B-Side comprising Components (ii) and (iii) has been aged at 40° C. for 0 days;

and

TFT

REACTIVE

SHIFT

=

100

*

[

(

TFT

79

-

TFT

0

)

/

TFT

0

]

Formula

Y

wherein

TFT 79 means a composition's TFT as determined using the FOAM REACTIVITY TEST after the composition's B-Side comprising Components (ii) and (iii) has been aged at 40° C. in a closed, pressure-rated, glass container that was placed in an oven for 79 days,

TFT 0 means a composition's TFT as determined using the FOAM REACTIVITY TEST after the composition's B-Side comprising Components (ii) and (iii) has been aged at 40° C. for 0 days.

2 . The method according to claim 1 , wherein the polyisocyanate comprises wherein the polyisocyanate comprises diphenylmethane diisocyanate, polyphenylene polymethylene polyisocyanate, tolylene diisocyanate, 1,5-naphtalenediisocyanate, p-phenylenediisocyanate, tolidine diisocyanate, or combinations thereof.

3 . The method according to claim 1 , wherein Component (ii) comprises a polyether polyol, polyester polyol, hydroxyl-terminated polythioethers, polyamides, polyesteramides, polycarbonates, polyacetals, polyolefins, polyamines, polythiols, polysiloxanes, glycols, or combinations thereof.

4 . The method according to claim 1 , wherein Component (iv) further comprises wherein Component (iv) further comprises of bis-(2-dimethylaminoethyl)ether; N,N, N′-trimethyl -N′-hydroxyethylbisaminoethylether; N,N-dimethylethanolamine; N,N-dimethylcyclohexylamine;

N-methyldicyclohexylamine; benzyldimethylamine; pentamethyldiethylenetriamine; N,N,N′,N″,N″-pentamethyldipropylenetriamine; N′-(3-(dimethylamino)propyl-N,N-dimethyl-1,3-propanediamine;

2-(2-dimethylaminoethoxy)ethanol; N,N, N′-trimethylaminoethyl-ethanolamine; 2-[N-(dimethylaminoethoxyethyl)-N-methylamino] ethanol; N,N, N′-trimethyl-N′-3-aminopropyl-bis(aminoethyl) ether; N,N,N′,N′-tetramethylenediamine; N-ethylmorpholine; 2,2′dimorpholinodiethylether; 1,3,5-tris (3-(dimethylamino)propyl)-hexahydro-s-triazine; 1,2-dimethlyimidazol; N-methyl-, N′-(2-dimethylamino)ethyl-piperazine; N,N-dimethylaminoethyl morpholine and triethylene diamine combinations thereof.

5 . The method according to claim 1 , wherein the hydrophilic carboxylic acid compound is a monocarboxylic acid selected from formic acid, acetic acid, or a combination thereof.

6 . The method according to claim 1 , wherein Component (vi) comprises trifluoropropenes, tetrafluoropropenes, pentafluoropropenes, chlorotrifloropropenes, chlorodifluoropropenes, chlorotrifluoropropenes, chlorotetrafluoropropenes, hexafluorobutenes, or combinations thereof.

7 . The method according to claim 1 , wherein Component (vi) comprises trans-1-chloro-3,3,3-trifluoropropene; (z)-1, 1, 1,4,4,4-hexafluorobut-2-ene; trans-1,3,3,3-tetrafluoroprop-1-ene or combinations thereof.

Assignments (3)
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 Jun 19, 2024
From: CAI, YANGJUN; WU, LIFENG; SINGH, SACHCHIDA; LIU, YUN-SHAN
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 067766/0965 →
Continuity (3)
Division 17273526
Provisional Application 62730725 · Sep 13, 2018
Related Publication 20240270896A1 · Aug 15, 2024
References Cited (4)
US 11958935B2 · Cai · 2024 [cited by examiner]
US 20130137787A1 · Burdeniuc · 2013 [cited by examiner]
US 20140271338A1 · Holcomb · 2014 [cited by examiner]
US 20180022885A1 · Younes · 2018 [cited by examiner]