# US 10,308,783 B2 · Stability of polyurethane polyol blends containing halogenated olefin blowing agent

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- Number: US 10,308,783 B2
- Document ID: US10308783B2
- Status: Granted
- Kind: B2
- Application number: 14/430,289
- Filed: 2013-09-19
- Published: 2015-07-16
- Granted: 2019-06-04
- Earliest claimed: 2012-09-24
- Assignees: Arkema Inc.
- Applicants: Arkema Inc.
- Inventors: Benjamin Bin Chen; Joseph S. Costa; Laurent Abbas; Sri R. Seshadri; Gary S. Smith
- Web page: https://patentgrep.com/patent/US10308783B2

## CPC

- C08J 9/144: {containing carbon, halogen and hydrogen only}
- C08G 18/14: {Manufacture of cellular products}
- C08G 18/1808: {having alkylene polyamine groups}
- C08G 18/1816: {having carbocyclic groups}
- C08G 18/1833: {having ether, acetal, or orthoester groups}
- C08G 18/4018: {Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48}
- C08G 18/4208: {containing aromatic groups}
- C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/6674: {with compounds of group C08G18/3203}
- C08G 18/72: Polyisocyanates or polyisothiocyanates
- C08J 9/0023: {containing oxygen}
- C08J 9/0061: {characterized by the use of several polymeric components}
- C08G 2110/0025: rigid
- C08J 2203/162: Halogenated unsaturated hydrocarbons, e.g. H2C=CF2
- C08J 2375/08: from polyethers
- C08J 2383/12: containing polyether sequences
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A polyol pre-mix composition includes a blowing agent having a halogenated hydroolefin, a polyol, a catalyst composition, and an antioxidant. The antioxidant may be, for example, a benzene diol or a benzene triol or other polyhydroxy-substituted aromatic compound, which is optionally substituted with one or more substituents such as alkyl groups. A two-part system for producing a thermosetting foam blend includes (a) a polyisocyanate and, optionally, one or more isocyanate compatible raw materials; and (b) the polyol pre-mix composition. A method for producing a thermosetting foam blend includes combining: (a) a polyisocyanate; and (b) the polyol pre-mix composition.

## Claims

### Claim 1

A polyol foam B-side pre-mix composition comprising a blowing agent comprising a halogenated hydroolefin, a polyol, a catalyst composition comprising an amine catalyst, a non-amine catalyst, or catalyst mixture thereof, and a primary antioxidant chosen from the group consisting of substituted and unsubstituted 1,2-benzenediols, substituted and unsubstituted 1,3-benzenediols and substituted and unsubstituted benzene triols and mixtures thereof wherein said polyol B-side foam premix forms a thermosetting foam when mixed with a polyol foam A-side premix.

### Claim 2 (depends on 1)

The polyol foam B-side pre-mix composition of claim 1, wherein the substituted and unsubstituted benzene triol is chosen from the group consisting of substituted and unsubstituted 1,2,3-benzenetriols, substituted and unsubstituted 1,2,4-benzenetriols, and substituted and unsubstituted 1,3,5-benzenetriols and mixtures thereof.

### Claim 3 (depends on 1)

The polyol foam B-side pre-mix composition of claim 1, wherein the primary antioxidant is present in an amount ranging from 0.01 wt % to 20 wt % antioxidant based on the total weight of the polyol pre-mix.

### Claim 4 (depends on 1)

The polyol foam B-side pre-mix composition of claim 1, further comprising a secondary antioxidant chosen from the group consisting of phenylene diamine, phosphites, sulfides, sulfites, and mercaptides and mixtures thereof.

### Claim 5 (depends on 1)

The polyol currently amended foam pre-mix composition of claim 1, wherein the catalyst composition comprises an oxygen-containing amine catalyst.

### Claim 6 (depends on 5)

The polyol B-side foam pre-mix composition of claim 5, wherein the oxygen-containing amine catalyst is an alkanolamine, ether amine, or a morpholine group-containing catalyst.

### Claim 7 (depends on 5)

The polyol B-side foam pre-mix composition of claim 5, wherein the oxygen-containing amine catalyst is a compound having the chemical structure:
R1R2N(CH2)2X
wherein:
R1 and R2 are the same or different and are each a C1-C6 alkyl group and/or an alkanol group,
X is O(CH2)2Y, OH, or NR3(CH2)2Y, where R3 is a C1-C6 alkyl group or an alkanol group, and
Y is OH or NR4R5, where R4 and R5 are the same or different and are each a C1-C6 alkyl group or an alkanol group, subject to the proviso that the compound contains at least one ether and/or hydroxyl group.

### Claim 8 (depends on 1)

The polyol B-side foam pre-mix composition of claim 1, wherein the catalyst composition comprises a non-oxygen-containing amine catalyst.

### Claim 9 (depends on 1)

The polyol B-side foam pre-mix composition of claim 1, wherein the catalyst composition further comprises a non-amine catalyst.

### Claim 10 (depends on 9)

The polyol B-side foam pre-mix composition of claim 9, wherein the non-amine catalyst comprises an organometallic salt of tin (Sn) or lead (Pb) or mixtures thereof.

### Claim 11 (depends on 1)

The polyol B-side foam pre-mix composition of claim 1, wherein the blowing agent additionally comprises one or more hydrofluorocarbons (HFCs), hydrofluoroethers (HFEs), hydrocarbons, alcohols, aldehydes, ketones, ethers/diethers, or CO2 generating materials, or combinations thereof.

### Claim 12 (depends on 1)

The polyol B-side foam pre-mix composition of claim 1, wherein the blowing agent comprises a halogenated hydroolefin selected from the group consisting of hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), and mixtures thereof, and optionally one or more hydrofluorocarbons (HFCs), hydrofluoroethers (HFEs), hydrocarbons, alcohols, aldehydes, ketones, ethers/diethers, esters, or carbon dioxide generating materials.

### Claim 13 (depends on 12)

The polyol B-side foam pre-mix composition of claim 12, wherein said hydrocarbons are selected from the group consisting of normal pentane, isopentane, cyclopentane, neopentane, and butane.

### Claim 14 (depends on 1)

The polyol B-side foam pre-mix composition of claim 1, further comprising a surfactant.

### Claim 15 (depends on 14)

The polyol B-side foam pre-mix composition of claim 14, wherein the surfactant comprises a polysiloxane polyoxyalkylene block co-polymer silicone surfactant.

### Claim 16 (depends on 1)

The polyol B-side foam pre-mix composition of claim 1, wherein the pre-mix composition is comprised of from about 0.3 to about 5 weight percent of one or more metal carboxylates, acetylacetonates, and alcoholates based on the total weight of the polyol pre-mix composition.

### Claim 17 (depends on 1)

The polyol B-side foam pre-mix composition of claim 1, further comprising a metal salt.

### Claim 18 (depends on 17)

The polyol B-side foam pre-mix composition of claim 17, wherein the metal salt comprises a carboxylate, alcoholate, and/or amidinate of a metal selected from the group consisting of Zn, Co, Ca, Mg, Bi, K, and Sn.

### Claim 19 (depends on 17)

The polyol B-side foam pre-mix composition of claim 17, wherein the metal salt comprises a carboxylate, alcoholate, and/or amidinate of a C1-C21 carboxylic acid or alcohol.

### Claim 20 (depends on 17)

The polyol B-side foam pre-mix composition of claim 17, wherein the metal salt comprises a carboxylate, alcoholate, and/or amidinate of a C1-C21 straight chain or branched aliphatic monocarboxylic acid or monoalcohol.

### Claim 21 (depends on 17)

The polyol B-side foam pre-mix composition of claim 17, wherein the metal salt is selected from the group consisting of magnesium formate, zinc octoate, calcium octoate, cobalt octoate, magnesium octoate, bismuth octoate, potassium octoate, and stannous octoate, magnesium acetylacetonate, zinc acetylacetonate, calcium acetylacetonate, cobalt acetylacetonate, bismuth acetylacetonate, potassium acetylacetonate, and tin acetylacetonate, and mixtures thereof.

### Claim 22 (depends on 1)

The polyol B-side foam pre-mix composition of claim 1, further comprising at least one flame retardant or suppressor.