IP Library Granted Patent US 11,649,315
Granted Patent B2
US 11,649,315 · App. 16/644,802 · Granted May 16, 2023

Polyurethane insulation foam composition comprising halogenated olefins and a tertiary amine compound

Inventors: Sachchida N. Singh (The Woodlands, TX); Lifeng Wu (The Woodlands, TX); Khang Nguyen (The Woodlands, TX)
Assignee: HUNTSMAN INTERNATIONAL LLC
C08G18/163C08G18/1833C08G18/227C08G18/329C08G18/3221C08G18/7664C08J9/144C08G2110/0025C08J2203/182C08J2205/10C08J2207/04
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Quick Facts
Patent No.
US 11,649,315
App. No.
16/644,802
Granted
May 16, 2023
Kind
B2
Abstract

A polyurethane insulation foam composition is disclosed herein. The polyurethane insulation foam comprises: (i) an 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; and (vii) optionally, other additives.

Claims (38)

1. A method of making a polyurethane foam product comprising:

providing a polyurethane insulation foam composition having a CT REACTIVITY SHIFT less than or equal to 60 and a TFT REACTIVITY SHIFT less than or equal to 60, wherein the polyurethane foam insulation comprises the following components:

(i) an isocyanate compound;

(ii) an isocyanate reactive compound;

(iii) water;

(iv) a tertiary amine having the structure Formula (a):

R 1 R 2 N—CH 2 —CH 2 —X—CH 2 —CH 2 —Y  (a)

wherein

R 1 and R 2 are independently C 1 -C 4 alkyl or C 2 -C 4 alkanol;

X is Oxygen or N—R 3 wherein R 3 is C 1 -C 4 alkyl or C 2 -C 4 alkanol or OH;

and

Y is OH or NR 4 R 5 wherein R 4 and R 5 are independently C 1 -C 4 alkyl or C 2 -C 4 alkanol;

(v) a hydrophilic carboxylic acid having the structure Formula (b):

(HO) n —R′—(COOH) m   (b)

wherein

R′ is a divalent C 1 -C 10 aliphatic hydrocarbon moiety, n and m are both integers and wherein when n=0 then m≥2 and wherein when n≥1 then m≥1;

(vi) a halogenated olefin blowing agent; and

(vii) other additives;

equilibrating an A-Side comprising Component (i) and a B-Side comprising Components (ii) to (v) to 15° C., wherein one or both of the A-side and B-side comprise Components (vi) and (vii); combining the A-Side and B-Side and mixing the combined composition for 4 seconds at 2500 rpm; and allowing the A-Side and the B-Side to react to form the pour-in-place polyurethane foam product, wherein the CT REACTIVITY by using Formulas X and Y respectively:

CT REACTIVE SHIFT=100*[(CT 17 −CT 0 )/CT 0 ]  Formula X:

wherein

CT 17 means a composition's CT after the composition's B-Side comprising has been aged at 40° C. in a closed, pressure-rated, glass container that was placed in an oven for 17 days;

CT 0 means a composition's CT after the composition's B-Side comprising has been aged at 40° C. for 0 days;

and

TFT REACTIVE SHIFT=100*[(TFT 17 −TFT 0 )/TFT 0 ]  Formula Y:

wherein

TFT 17 means a composition's TFT after the composition's B-Side comprising has been aged at 40° C. in a closed, pressure-rated, glass container that was placed in an oven for 17 days;

TFT 0 means a composition's TFT after the composition's B-Side has been aged at 40° C. for 0 days

wherein CT means the elapsed time between the moment the A-side is mixed with the B- Side and the formation of a fine froth in the composition and

wherein TFT means the elapsed time between the moment the A-side is mixed with the B-Side and the time on which an outer skin of the polyurethane foam product loses its adhesive quality.

2. The method according to claim 1 , wherein Component (i) comprises aliphatic, araliphatic, aromatic polyisocyanates, or combinations thereof.

3. The method according to claim 2 , wherein the polyisocyanate comprises diphenylmethane diisocyanate, tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylxylene diisocyanate, 1,5-naphtalenediisocyanate, p-phenylenediisocyanate, 1,4-cyclohexanediisocyanate, tolidine diisocyanate, or combinations thereof.

4. 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.

5. The method according to claim 1 , wherein Component (iv) further comprises 1 -methylimidazole, 1 , 2 -dimethlyimidazol and 1 -methyl- 2 -hydroxyethylimidazole, N-( 3 -aminopropyl)imidazole, 1 -n-butyl- 2 -methylimidazole, 1 -iso-butyl- 2 -methylimidazole; N, N, N′-trimethylaminoethyl-ethanolamine, N-methyldicyclohexylamine, 2 , 2 ′dimorpholinodiethylether, N-methylmorpholine, N,N-dimethylcyclohexylamine, 3 , 5 -dimethylthio- 2 , 4 -toluenediamine, N,N-dimethyl-p-toluidine, N, N-dimethyl-p-toluidine, 1,1′, 1″, 1′″-(1,2-ethanediyldinitrilo)tetrakis[2-propanol] neodecanoate complexes, 2,2′,2″,2′″-(1,2-ethanediyldinitrilo)tetrakis[ethanol] neodecanoate complexes, or combinations thereof.

6. The method according to claim 1 , wherein Component (v) comprises a Waste AGS Acid Compound, a Natural Acid Compound, or combinations thereof.

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

8. The method according to claim 1 , wherein Component (vii) comprise a secondary blowing agent comprising air, nitrogen, carbon dioxide, hydrofluoroalkanes, alkanes, alkenes, mono-carboxylic acid salts, ketones, ethers, or combinations thereof.

9. The method according to claim 1 , where the foam composition does not contain a guanidine compound.

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 Dec 10, 2020
From: SINGH, SACHCHIDA N.; WU, LIFENG; NGUYEN, KHANG
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 054669/0460 →
Continuity (2)
Provisional Application 62558428 · Sep 14, 2017
Related Publication 20210070917A1 · Mar 11, 2021