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US4365024A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyoxyalkylene/unsaturated diester reaction product for cellular foam stabilization

Assignee: Celotex Corp
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Filing: 1981-07-10
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Granted: 1982-12-21
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Expires: 2001-07-10
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Abstract

Abstract Polyoxyalkylene surfactants for cellular foams 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 2026-11-01 18:28
CPC Classifications
C; C08; C08J; C08J9/00; C08J9/0061; C08F; C08F283/00; C08F283/06; C08J2451/00

Claims Analysis

Total Claims: 39
Claim 1
Independent Claim 157 words
A foam material comprising the reaction product of: A. phenol aldehyde resin forming ingredients, and 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, and wherein polyoxyalkylene adduct is treated either before or after its reaction with the esterified unsaturated dibasic acid with a capping agent capable of reacting with the hydroxyl groups of said adduct to reduce the hydroxyl number of said adduct to less than 50.
Claim 2
Dependent Claim 157 words
A foam material comprising the reaction product of: A. phenol aldehyde resin forming ingredients, and 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, and wherein polyoxyalkylene adduct is treated either before or after its reaction with the esterified unsaturated dibasic acid with a capping agent capable of reacting with the hydroxyl groups of said adduct to reduce the hydroxyl number of said adduct to less than 50.
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--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 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 20 words
The composition of claims 1 or 7 wherein the hydroxyl number of said adduct is reduced to less than 10.
Claim 10
Dependent Claim 14 words
The composition of claims 1 or 7 wherein the capping agent is acetic anhydride.
Claim 11
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 12
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 13
Dependent Claim 32 words
The composition of claim 11 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 14
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 15
Dependent Claim 57 words
The composition of claim 13 wherein the esterified unsaturated dibasic acid has the formula T 1 O 2 C--C u H 2u-2 --CO 2 T 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 16
Dependent Claim 18 words
The composition of claim 14 wherein the hydroxyl number of said adduct is reduced to less than 10.
Claim 17
Dependent Claim 12 words
The composition of claim 15 wherein the capping agent is acetic anhydride.
Claim 18
Dependent Claim 27 words
The composition of claim 16 wherein the esterified unsaturated dibasic acid is a member selected from the group consisting of dioctyl maleate, ditridecyl maleate and dioleyl maleate.
Claim 19
Dependent Claim 37 words
The composition of claim 16 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 20
Dependent Claim 35 words
The composition of claim 18 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 21
Dependent Claim 24 words
The composition of claim 19 wherein the ethoxylated castor oil contains from about 35 to 40 moles of ethylene oxide per mole of oil.
Claim 22
Dependent Claim 41 words
The composition of claim 20 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 23
Dependent Claim 158 words
In the method of preparing cellular foam from: A. phenol aldehyde resin 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, and wherein polyoxyalkylene adduct is treated either before or after its reaction with the esterified unsaturated dibasic acid with a capping agent capable of reacting with the hydroxyl groups of said adduct to reduce the hydroxyl number of said adduct to less than 50.
Claim 24
Dependent Claim 158 words
In the method of preparing cellular foam from: A. phenol aldehyde resin 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, and wherein polyoxyalkylene adduct is treated either before or after its reaction with the esterified unsaturated dibasic acid with a capping agent capable of reacting with the hydroxyl groups of said adduct to reduce the hydroxyl number of said adduct to less than 50.
Claim 25
Dependent Claim 51 words
The process of claim 22 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 26
Dependent Claim 54 words
The process of claim 23 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 27
Dependent Claim 14 words
The process of claims 20 or 24 wherein the capping agent is acetic anhydride.
Claim 28
Dependent Claim 19 words
The process of claim 22 wherein an organo transition metal catalyst is additionally present during the free-radical initiated reaction.
Claim 29
Dependent Claim 13 words
The process of claim 26 wherein the organo transition metal catalyst is ferrocene.
Claim 30
Dependent Claim 45 words
The process of claim 22 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 31
Dependent Claim 33 words
The process of claim 28 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 32
Dependent Claim 110 words
The process of claim 22 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 33
Dependent Claim 51 words
The process of claim 30 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 34
Dependent Claim 27 words
The process of claim 31 wherein the capping agent is acetic anhydride, the acetic acid which forms during the capping treatment being removed from the reaction mixture.
Claim 35
Dependent Claim 27 words
The process of claim 32 wherein the esterified unsaturated dibasic acid is a member selected from the group consisting of dioctyl maleate, ditridecyl maleate and dioleyl maleate.
Claim 36
Dependent Claim 37 words
The process of claim 32 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 37
Dependent Claim 35 words
The process of claim 34 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 38
Dependent Claim 24 words
The process of claim 35 wherein the ethoxylated castor oil contains from about 35 to 40 moles of ethylene oxide per mole of oil.
Claim 39
Dependent Claim 41 words
The process of claim 36 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)

US3383351A Cited
US3304273A Cited
US3779959A Cited
US3546321A Cited
US3914188A Cited
US4250077A Cited
US4140842A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-12-20 1986-06-21 1986-12-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-12-20 1990-06-21 1990-12-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-12-20 1994-06-21 1994-12-21 $7700.00 Window Closed / Lapsed

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