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US4418158A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyoxyalkylene/unsaturated diester reaction product for cellular foam stabilization

Assignee: Celotex Corp
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Filing: 1982-09-29
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Granted: 1983-11-29
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Expires: 2002-09-29
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Abstract

Abstract Polyoxyalkylene surfactants for cellular forms can be prepared by reacting a polyoxyalkylene adduct and an esterified unsaturated dibasic acid in the presence of a free-radical initiator.

Inventors

  • 👤 Richard L. Frentzel

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 14:21
CPC Classifications
C; C08; C08J; C08J9/00; C08J9/0061; C08F; C08F283/00; C08F283/06; C08J2451/00; Y; Y10; Y10S; Y10S521/00; Y10S521/902

Claims Analysis

Total Claims: 43
Claim 1
Independent Claim 109 words
A foam material comprising the mixture of: A. polyurethane polymer forming ingredients, B. a blowing agent, and C. a surfactant which comprises the reaction product consisting of (a) a polyoxyalkylene adduct having the formula H--polyoxyalkylene chain).sub.t R, wherein R is an organic or inorganic radical and t is the number of polyoxyalkylene chains reacted onto R, and (b) an esterified unsaturated dibasic acid having the formula T.sup.1 O.sub.2 C--C.sub.u H.sub.2u-2)CO.sub.2 T.sup.2 wherein u is 2 or 3 and T 1 and T 2 are identical or different and represent a straight or branched, saturated or unsaturated hydrocarbon chain, in the presence of an effective amount of a free-radical initiator.
Claim 2
Dependent Claim 109 words
A foam material comprising the mixture of: A. polyurethane polymer forming ingredients, B. a blowing agent, and C. a surfactant which comprises the reaction product consisting of (a) a polyoxyalkylene adduct having the formula H--polyoxyalkylene chain).sub.t R, wherein R is an organic or inorganic radical and t is the number of polyoxyalkylene chains reacted onto R, and (b) an esterified unsaturated dibasic acid having the formula T.sup.1 O.sub.2 C--C.sub.u H.sub.2u-2)CO.sub.2 T.sup.2 wherein u is 2 or 3 and T 1 and T 2 are identical or different and represent a straight or branched, saturated or unsaturated hydrocarbon chain, in the presence of an effective amount of a free-radical initiator.
Claim 3
Dependent Claim 51 words
The composition of claim 1 wherein the esterified unsaturated dibasic acid has the formula T.sup.1 O.sub.2 C--Cu.sub.u H.sub.2u-2 --CO.sub.2 T.sup.2 wherein u is 2 or 3 and T 1 and T 2 are identical and represent a straight or branched, saturated or unsaturated hydrocarbon chain of 4 to 18 carbon atoms.
Claim 4
Dependent Claim 33 words
The composition of claim 2 wherein the esterified unsaturated dibasic acid is a member selected from the group consisting of dibutyl fumarate, dibutyl maleate, dihexyl maleate, diamyl methylenemalonate, dipropyl itaconate and dibutyl itaconate.
Claim 5
Dependent Claim 27 words
The composition of claim 2 wherein T 1 and T 2 represent a straight or branched, saturated or unsaturated hydrocarbon chain of 8 to 18 carbon atoms.
Claim 6
Dependent Claim 27 words
The composition of claim 4 wherein the esterified unsaturated dibasic acid is a member selected from the group consisting of dioctyl maleate, ditridecyl maleate and dioleyl maleate.
Claim 7
Dependent Claim 26 words
The composition of claim 1 wherein t is an integer from 1 to 8 and the molecular weight of the polyoxyalkylene adduct is above about 1000.
Claim 8
Dependent Claim 34 words
The composition of claim 6 wherein the polyoxyalkylene chain or chains of the adduct are derived from an alkylene oxide selected from the group consisting of ethylene oxide, 1,2-epoxypropane, an epoxybutane, and mixtures thereof.
Claim 9
Dependent Claim 50 words
The composition of claims 1 or 7 wherein the polyoxyalkylene adduct is capped by treatment either before or after the free-radical initiated reaction with a capping agent capable of reacting with the hydroxyl groups of said adduct, whereby the hydroxyl number of said adduct is reduced to less than 50.
Claim 10
Dependent Claim 18 words
The composition of claim 8 wherein the hydroxyl number of said adduct is reduced to less than 10.
Claim 11
Dependent Claim 12 words
The composition of claim 8 wherein the capping agent is acetic anhydride.
Claim 12
Dependent Claim 20 words
The composition of claim 1 wherein an organo transition metal catalyst is additionally present in the free-radical initiated reaction mixture.
Claim 13
Dependent Claim 45 words
The composition of claim 1 wherein the esterified unsaturated dibasic acid comprises about 5 to 40 weight percent of the free-radical initiated reaction mixture, and the initiator comprises from about 2 to 30 weight percent, based on the weight of the esterified unsaturated dibasic acid.
Claim 14
Dependent Claim 32 words
The composition of claim 12 wherein an organo transition metal catalyst is additionally present in the reaction mixture in a concentration from about 0.001 to 0.05 grams per gram of free-radical initiator.
Claim 15
Dependent Claim 110 words
The composition of claim 1 wherein the polyoxyalkylene adduct is a member selected from the group consisting of (a) an alkoxylated amine having the formula: ##STR13## wherein R 1 is independently an alkoxylated chain having the formula: ##STR14## s is an integer from 2 to 10 inclusive and the ratio p:q is from 10:90 to 90:10, the molecular weight of said alkoxylated amine being from about 1500 to 12,000, (b) a linear block copolymer of ethylene oxide and propylene oxide, the molecular weight of said block copolymer being above about 2000 and the ethylene oxide content being from about 30 to 80 weight percent, and (c) an ethoxylated castor oil.
Claim 16
Dependent Claim 51 words
The composition of claim 14 wherein the esterified unsaturated dibasic acid has the formula T.sup.1 O.sub.2 C--C.sub.u H.sub.2u-2 --CO.sub.2 T.sup.2 wherein u is 2 or 3 and T 1 and T 2 are identical and represent a straight or branched, saturated or unsaturated hydrocarbon chain of 8 to 18 carbon atoms.
Claim 17
Dependent Claim 48 words
The composition of claim 15 wherein the polyoxyalkylene adduct is capped by treatment either before or after the free-radical initiated reaction with a capping agent capable of reacting with the hydroxyl groups of said adduct, whereby the hydroxyl number of said adduct is reduced to less than 50.
Claim 18
Dependent Claim 18 words
The composition of claim 16 wherein the hydroxyl number of said adduct is reduced to less than 10.
Claim 19
Dependent Claim 12 words
The composition of claim 17 wherein the capping agent is acetic anhydride.
Claim 20
Dependent Claim 27 words
The composition of claim 18 wherein the esterified unsaturated dibasic acid is a member selected from the group consisting of dioctyl maleate, ditridecyl maleate from dioleyl maleate.
Claim 21
Dependent Claim 37 words
The composition of claim 18 wherein (a) the polyoxyalkylene adduct is ethoxylated castor oil, and (b) the esterified unsaturated dibasic acid is a member selected from the group consisting of dioctyl maleate, ditridecyl maleate and dioleyl maleate.
Claim 22
Dependent Claim 35 words
The composition of claim 20 wherein (a) the ethoxylated castor oil contains from about 25 to 60 moles of ethylene oxide per mole of oil, and (b) the esterified unsaturated dibasic acid is ditridecyl maleate.
Claim 23
Dependent Claim 24 words
The composition of claim 21 wherein the ethoxylated castor oil contains from about 35 to 40 moles of ethylene oxide per mole of oil.
Claim 24
Dependent Claim 41 words
The composition of claim 22 wherein the ditridecyl maleate comprises about 5 to 40 weight percent of the free-radical initiated reaction mixture and the initiator comprises from about 2 to 30 weight percent, based on the weight of the ditridecyl maleate.
Claim 25
Dependent Claim 114 words
In the method of preparing a cellular foam from: A. polyurethane polymer forming ingredients, and B. a blowing agent, the improvement which comprises utilizing as surfactant the reaction product consisting of (a) a polyoxyalkylene adduct having the formula H--polyoxyalkylene chain).sub.t R, wherein R is an organic or inorganic radical and t is the number of polyoxyalkylene chains reacted onto R, and (b) an esterified unsaturated dibasic acid having the formula T.sup.1 O.sub.2 C--C.sub.u H.sub.2u-2 --CO.sub.2 T.sup.2 wherein u is 2 or 3 and T 1 and T 2 are identical or different and represent a straight or branched, saturated or unsaturated hydrocarbon chain, in the presence of an effective amount of a free-radical initiator.
Claim 26
Dependent Claim 114 words
In the method of preparing a cellular foam from: A. polyurethane polymer forming ingredients, and B. a blowing agent, the improvement which comprises utilizing as surfactant the reaction product consisting of (a) a polyoxyalkylene adduct having the formula H--polyoxyalkylene chain).sub.t R, wherein R is an organic or inorganic radical and t is the number of polyoxyalkylene chains reacted onto R, and (b) an esterified unsaturated dibasic acid having the formula T.sup.1 O.sub.2 C--C.sub.u H.sub.2u-2 --CO.sub.2 T.sup.2 wherein u is 2 or 3 and T 1 and T 2 are identical or different and represent a straight or branched, saturated or unsaturated hydrocarbon chain, in the presence of an effective amount of a free-radical initiator.
Claim 27
Dependent Claim 51 words
The process of claim 24 wherein the esterified unsaturated dibasic acid has the formula T.sup.1 O.sub.2 C--C.sub.u H.sub.2u-2 --CO.sub.2 T.sup.2 wherein u is 2 or 3 and T 1 and T 2 are identical and represent a straight or branched, saturated or unsaturated hydrocarbon chain of 8 to 18 carbon atoms.
Claim 28
Dependent Claim 54 words
The process of claim 25 wherein t is an integer from 1 to 8, the molecular weight of the polyoxyalkylene adduct is above about 1000, and the polyoxyalkylene chain or chains of the adduct are derived from an alkylene oxide selected from the group consisting of ethylene oxide, 1,2-epoxypropane, an epoxybutane, and mixtures thereof.
Claim 29
Dependent Claim 48 words
The process of claims 23 or 26 wherein the polyoxyalkylene adduct is treated either before or after the free-radical initiated reaction with a capping agent capable of reacting with the hydroxyl groups of said adduct, whereby the hydroxyl number of said adduct is reduced to less than 50.
Claim 30
Dependent Claim 12 words
The process of claim 27 wherein the capping agent is acetic anhydride.
Claim 31
Dependent Claim 19 words
The process of claim 23 wherein an organo transition metal catalyst is additionally present during the free-radical initiated reaction.
Claim 32
Dependent Claim 13 words
The process of claim 29 wherein the organo transition metal catalyst is ferrocene.
Claim 33
Dependent Claim 45 words
The process of claim 23 wherein the esterified unsaturated dibasic acid comprises about 5 to 40 weight percent of the free-radical initiated reaction mixture, and the initiator comprises from about 2 to 30 weight percent, based on the weight of the esterified unsaturated dibasic acid.
Claim 34
Dependent Claim 33 words
The process of claim 31 wherein an organo transition metal catalyst is additionally present during the free-radical initiated reaction in a concentration from about 0.001 to 0.05 grams per gram of free-radical initiator.
Claim 35
Dependent Claim 110 words
The process of claim 25 wherein the polyoxyalkylene adduct is a member selected from the group consisting of (a) an alkoxylated amine having the formula: ##STR15## wherein R 1 is independently an alkoxylated chain having the formula: ##STR16## s is an integer from 2 to 10 inclusive and the ratio p:q is from 10:90 to 90:10, the molecular weight of said alkoxylated amine being from about 1500 to 12,000, (b) a linear block copolymer of ethylene oxide and propylene oxide, the molecular weight of said block copolymer being above about 2000 and the ethylene oxide content being from about 30 to 80 weight percent, and (c) an ethoxylated castor oil.
Claim 36
Dependent Claim 51 words
The process of claim 33 wherein the esterified unsaturated dibasic acid has the formula T.sup.1 O.sub.2 C--C.sub.u H.sub.2u-2 --CO.sub.2 T.sup.2 wherein u is 2 or 3 and T 1 and T 2 are identical and represent a straight or branched, saturated or unsaturated hydrocarbon chain of 8 to 18 carbon atoms.
Claim 37
Dependent Claim 46 words
The process of claim 34 wherein the polyoxyalkylene adduct is treated either before or after the free-radical initiated reaction with a capping agent capable of reacting with the hydroxyl groups of said adduct, whereby the hydroxyl number of said adduct is reduced to less than 50.
Claim 38
Dependent Claim 27 words
The process of claim 35 wherein the capping agent is acetic anhydride, the acetic acid which forms during the capping treatment being removed from the reaction mixture.
Claim 39
Dependent Claim 27 words
The process of claim 36 wherein the esterified unsaturated dibasic acid is a member selected from the group consisting of dioctyl maleate, ditridecyl maleate and dioleyl maleate.
Claim 40
Dependent Claim 37 words
The process of claim 36 wherein (a) the polyoxyalkylene adduct is ethoxylated castor oil, and (b) the esterified unsaturated dibasic acid is a member selected from the group consisting of dioctyl maleate, ditridecyl maleate and dioleyl maleate,
Claim 41
Dependent Claim 35 words
The process of claim 38 wherein (a) the ethoxylated castor oil contains from about 25 to 60 moles of ethylene oxide per mole of oil, and (b) the esterified unsaturated dibasic acid is ditridecyl maleate.
Claim 42
Dependent Claim 24 words
The process of claim 39 wherein the ethoxylated castor oil contains from about 35 to 40 moles of ethylene oxide per mole of oil.
Claim 43
Dependent Claim 41 words
The process of claim 40 wherein the ditridecyl maleate comprises about 5 to 40 weight percent of the free-radical initiated reaction mixture and the initiator comprises from about 2 to 30 weight percent, based on the weight of the ditridecyl maleate.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-11-28 1987-05-30 1987-11-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-11-28 1991-05-30 1991-11-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-11-28 1995-05-30 1995-11-29 $7700.00 Window Closed / Lapsed

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