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US4533486A Expired / Lapsed US ⏱️ 0.0 years remaining

Sulfated addition products of selected unsaturated dicarboxylic acids and poly(oxyalkylated) alcohols as anionic surfactants

Assignee: Arch Chemicals Inc
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Filing: 1984-09-24
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Granted: 1985-08-06
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Expires: 2004-09-24
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Abstract

Abstract Described are anionic surfactants which are made by (1) reacting maleic acid, fumaric acid, or mixtures thereof with at least one selected poly(oxyalkylated) alcohol in the presence of a peroxy-type free radical initiator to form a carboxylic acid group-containing addition product and (2) sulfating said addition product with a sufficient amount of a sulfating agent (i.e. sulfamic acid) to convert at least a major proportion of the terminal hydroxyl groups to sulfate groups. These surfactants exhibit excellent surface activity as well as being highly soluble in caustic solutions.

Inventors

  • 👤 Michael Scardera
  • 👤 John G. Bayusik

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 20:13
CPC Classifications
C; C23; C23G; C23G1/00; C23G1/14; C07; C07C; C07C59/00; C07C59/235; C07C59/305; C08; C08F; C08F2/00; C08F2/12; C08F2/16; C08F2/22; C08F2/24; C08F2/26; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/329; C08G65/331; C08G65/332; C08G65/334; C08G65/3348; C09; C09K; C09K23/00; C09K23/10; C11; C11D; C11D1/00; C11D1/02; C11D1/12; C11D1/123; Y; Y10; Y10S; Y10S516/00; Y10S516/01; Y10S516/03

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 183 words
A surfactant composition made by the process comprising: a. forming a carboxylic acid group-containing addition product by reacting, in the presence of a peroxy-type free-radical initiator, an ethylenically unsaturated dicarboxylic acid selected from the group consisting of maleic acid and fumaric acid and mixtures thereof, with at least one poly(oxyalkylated) alcohol having the formula: ##STR3## wherein R is a hydrocarbon-containing radical having an average of from about 6 to about 18 carbon atoms; R 1 , R 2 , and R 3 are individually selected from hydrogen and methyl with the proviso that R 2 is different than R 1 and R 3 ; x is an integer having a value from 1 to about 25; y is an integer having a value from about 1 to about 25; and z is an integer from about 0 to about 25; in the said weight ratio of said poly(oxyalkylated) from about 95:5 to about 40:60; and b. sulfating said addition product with a sufficient amount of a sulfating agent to convert at least a major portion of said terminal hydroxyl groups to sulfonate groups.
Claim 2
Dependent Claim 183 words
A surfactant composition made by the process comprising: a. forming a carboxylic acid group-containing addition product by reacting, in the presence of a peroxy-type free-radical initiator, an ethylenically unsaturated dicarboxylic acid selected from the group consisting of maleic acid and fumaric acid and mixtures thereof, with at least one poly(oxyalkylated) alcohol having the formula: ##STR3## wherein R is a hydrocarbon-containing radical having an average of from about 6 to about 18 carbon atoms; R 1 , R 2 , and R 3 are individually selected from hydrogen and methyl with the proviso that R 2 is different than R 1 and R 3 ; x is an integer having a value from 1 to about 25; y is an integer having a value from about 1 to about 25; and z is an integer from about 0 to about 25; in the said weight ratio of said poly(oxyalkylated) from about 95:5 to about 40:60; and b. sulfating said addition product with a sufficient amount of a sulfating agent to convert at least a major portion of said terminal hydroxyl groups to sulfonate groups.
Claim 3
Dependent Claim 26 words
The surfactant composition of claim 1 wherein R is a linear, aliphatic hydrocarbon radical having an average of from about 8 to about 14 carbon atoms.
Claim 4
Dependent Claim 20 words
The surfactant composition of claim 1 wherein x is an integer having a value from about 2 to about 12.
Claim 5
Dependent Claim 20 words
The surfactant composition of claim 1 wherein y is an integer having a value from about 2 to about 15.
Claim 6
Dependent Claim 21 words
The surfactant composition of claim 1 wherein z is an integer having a value from about 5 to : about 20.
Claim 7
Dependent Claim 25 words
The surfactant composition of claim 1 wherein the weight ratio of said poly(oxyalkylated) alcohol to said dicarboxylic acid is from about 90:10 to about 60:40.
Claim 8
Dependent Claim 32 words
The surfactant composition of claim 1 wherein said addition product is sulfated with a sufficient amount of a sulfating agent to convert at least substantially all of said terminal hydroxyl sulfonate groups.
Claim 9
Dependent Claim 13 words
The surfactant composition of claim 1 wherein said sulfating agent is sulfamic acid.
Claim 10
Dependent Claim 17 words
The surfactant composition of claim 1 wherein said addition product is neutralized prior to sulfating step (b).
Claim 11
Dependent Claim 215 words
A surfactant composition made by the process comprising: a. forming a carboxylic acid group-containing addition product by reacting, in the presence of a peroxy-type free-radical initiator, an ethylenically unsaturated dicarboxylic acid selected from the group consisting of maleic acid and fumaric acid and mixtures thereof, with at least one poly(oxyalkylated) alcohol having the formula: ##STR4## wherein R is a hydrocarbon-containing radical having an average of from about 6 to about 18 carbon atoms; R 1 , R 2 , and R 3 are individually selected from hydrogen and methyl with the proviso that R 2 is different than R 1 and R 3 ; x is an integer having a value from 1 to about 25; y is an integer having a value from about 1 to about 25; and z is an integer weight ratio of said poly(oxyalkylated) alcohol to said dicarboxylic acid being from about 95:5 to about 40:60; b. sulfating said addition product with a sufficient amount of a sulfating agent to convert at least a major portion of terminal hydroxyl groups to sulfate groups; and c. neutralizing said sulfated addition product with a sufficient amount of a neutralizing agent to convert at least a major portion of the total of said carboxylic acid groups and said sulfate groups to salt groups.
Claim 12
Dependent Claim 215 words
A surfactant composition made by the process comprising: a. forming a carboxylic acid group-containing addition product by reacting, in the presence of a peroxy-type free-radical initiator, an ethylenically unsaturated dicarboxylic acid selected from the group consisting of maleic acid and fumaric acid and mixtures thereof, with at least one poly(oxyalkylated) alcohol having the formula: ##STR4## wherein R is a hydrocarbon-containing radical having an average of from about 6 to about 18 carbon atoms; R 1 , R 2 , and R 3 are individually selected from hydrogen and methyl with the proviso that R 2 is different than R 1 and R 3 ; x is an integer having a value from 1 to about 25; y is an integer having a value from about 1 to about 25; and z is an integer weight ratio of said poly(oxyalkylated) alcohol to said dicarboxylic acid being from about 95:5 to about 40:60; b. sulfating said addition product with a sufficient amount of a sulfating agent to convert at least a major portion of terminal hydroxyl groups to sulfate groups; and c. neutralizing said sulfated addition product with a sufficient amount of a neutralizing agent to convert at least a major portion of the total of said carboxylic acid groups and said sulfate groups to salt groups.
Claim 13
Dependent Claim 26 words
The surfactant composition of claim 10 wherein R is a linear, aliphatic hydrocarbon radical having an average of from about 8 to about 14 carbon atoms.
Claim 14
Dependent Claim 20 words
The surfactant composition of claim 10 wherein x is an integer having a value from about 2 to about 12.
Claim 15
Dependent Claim 20 words
The surfactant composition of claim 10 wherein y is an integer having a value from about 2 to about 15.
Claim 16
Dependent Claim 20 words
The surfactant composition of claim 10 wherein z is an integer having a value from about 5 to about 20.
Claim 17
Dependent Claim 25 words
The surfactant composition of claim 10 wherein the weight ratio of said poly(oxyalkylated) alcohol to said dicarboxylic acid is from about 90:10 to about 60:40.
Claim 18
Dependent Claim 39 words
The surfactant composition of claim 10 wherein said addition product is neutralized with a sufficient amount of a neutralization agent to convert substantially all of the total of said carboxylic acid groups and said sulfate groups to salt groups.
Claim 19
Dependent Claim 29 words
An aqueous solution comprising water and at least about 10% by weight of an alkali metal hyroxide and an effective surface active amount of the surfactant of claim 1.
Claim 20
Dependent Claim 29 words
An aqueous solution comprising water and at least about 10% by weight of an alkali metal hydroxide and an effective surface active amount of the surfactant of claim 10.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-08-05 1989-02-04 1989-08-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-08-05 1993-02-04 1993-08-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-08-05 1997-02-04 1997-08-06 $7700.00 Window Closed / Lapsed

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