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US4721580A Expired / Lapsed US ⏱️ 0.0 years remaining

Anionic end-capped oligomeric esters as soil release agents in detergent compositions

Assignee: Procter and Gamble Co
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Filing: 1987-01-07
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Granted: 1988-01-26
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Expires: 2007-01-07
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Abstract

Abstract Oligomeric esters and mixtures thereof useful as soil release agents in consumer laundering and fabric care compositions are disclosed. Preferred oligomers have the formulae ##STR1## wherein E is ##STR2## wherein the R substituents may be the same or different and are members selected from the group consisting of --CH 2 CH(CH 3 )--, --CH(CH 3 )CH 2 --and --CH 2 CH 2 --, n is an integer from 1 to 30 and x is an integer from 0 to about 20 provided that when E is ##STR3## x is at least 1. Mixtures of the oligomers having one and two NaO 3 S(CH 2 CH 2 O) n --substituents are particularly effective and formulable soil release agents in detergent compositions.

Inventors

  • 👤 Eugene P. Gosselink

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 14:21
CPC Classifications
C; C07; C07C; C07C309/00; C07C309/01; C07C309/02; C07C309/03; C07C309/04; C11; C11D; C11D3/00; C11D3/0005; C11D3/0036; C08; C08G; C08G63/00; C08G63/68; C08G63/688; C08G63/6884; C08G63/6886; C11D3/16; C11D3/37; C11D3/3703; C11D3/3715

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 236 words
Oligomeric esters having at least one anionic substituent group, said esters having the formula Q--Z--O--R--O].sub.x Z--Q' I or Q"--Z--O--R--O].sub.y H II or mixtures thereof; wherein Q, Q' and Q" may be the same or different anionic substituents selected from the group consisting of MO 3 S(CH 2 CH 2 O) n --, MO 3 S--(L) q (YO) m (CH 2 CH 2 O) r , and mixtures thereof, wherein M is H or a salt-forming cation, L is phenoethoxy, phenoxypropoxy or C 1 -C 6 alkoxy, Y is --CH 2 CH(CH 3 )-- or --CH(CH 3 )CH 2 --, n is an integer from 1 to 30, q is 1 or 0, m is an integer from 0 to 15 provided that m+q is at least 1 and r is an integer from 0 to 30; x and y may be the same or different and are each integers with x selected from 0 to 20 and y selected from 1 to 20; the R-substituents may be the same or different alkylene substituents selected from the group consisting of --CH 2 CH 2 --, --CH 2 CH(X)-- and --CH(X)CH 2 -- wherein X is methyl, ethyl, methoxymethyl, or C 1 -C 4 -alkylpoly(oxyalkylene)oxymethyl, or mixtures thereof; and the Z-substituents may be the same or different aryldicarbonyl substituents selected from the group consisting of ##STR29## and mixtures thereof with aryl-1,3-dicarbonyl or substituted aryl-1,3-dicarbonyl or substituted aryl-1,4-dicarbonyl groups.
Claim 2
Dependent Claim 236 words
Oligomeric esters having at least one anionic substituent group, said esters having the formula Q--Z--O--R--O].sub.x Z--Q' I or Q"--Z--O--R--O].sub.y H II or mixtures thereof; wherein Q, Q' and Q" may be the same or different anionic substituents selected from the group consisting of MO 3 S(CH 2 CH 2 O) n --, MO 3 S--(L) q (YO) m (CH 2 CH 2 O) r , and mixtures thereof, wherein M is H or a salt-forming cation, L is phenoethoxy, phenoxypropoxy or C 1 -C 6 alkoxy, Y is --CH 2 CH(CH 3 )-- or --CH(CH 3 )CH 2 --, n is an integer from 1 to 30, q is 1 or 0, m is an integer from 0 to 15 provided that m+q is at least 1 and r is an integer from 0 to 30; x and y may be the same or different and are each integers with x selected from 0 to 20 and y selected from 1 to 20; the R-substituents may be the same or different alkylene substituents selected from the group consisting of --CH 2 CH 2 --, --CH 2 CH(X)-- and --CH(X)CH 2 -- wherein X is methyl, ethyl, methoxymethyl, or C 1 -C 4 -alkylpoly(oxyalkylene)oxymethyl, or mixtures thereof; and the Z-substituents may be the same or different aryldicarbonyl substituents selected from the group consisting of ##STR29## and mixtures thereof with aryl-1,3-dicarbonyl or substituted aryl-1,3-dicarbonyl or substituted aryl-1,4-dicarbonyl groups.
Claim 3
Dependent Claim 22 words
Oligomeric esters or mixtures thereof according to claim 1 wherein x and y are integers below 8, and the Z-substituents are ##STR30##
Claim 4
Dependent Claim 24 words
Oligomeric esters according to claim 1 wherein x is an integer from 3 to 7 and y is an integer from 4 to 8.
Claim 5
Dependent Claim 69 words
Mixtures of anionic oligomeric esters according to claim 1 wherein Z is ##STR31## all R substituents are independently selected from --CH 2 CH 2 --, --CH 2 CH(CH 3 )-- and --CH(CH 3 )CH 2 --, and Q, Q' and Q" may be the same or different and are each selected from NaO 3 S(CH 2 CH 2 O) n wherein n is an integer from 2 to 15.
Claim 6
Dependent Claim 30 words
Mixtures of anionic oligomeric esters according to claim 4 wherein the weight ratio of esters having formula I and esters having formula II is from about 30:1 to about 1:20.
Claim 7
Dependent Claim 46 words
Mixtures of anionic oligomeric esters according to claim 4 wherein the molar ratio of R substituents being --CH 2 CH 2 -- substituents to R substituents being --CH 2 CH(CH 3 )-- and --CH(CH 3 )CH 2 -- substituents is from about 0:1 to about 0.9:0.1.
Claim 8
Dependent Claim 33 words
Mixtures of anionic oligomeric esters according to claim 4 wherein at least 2% by weight of the esters having formula I or II contain from 4 ##STR32## units to about 8 ##STR33## units.
Claim 9
Dependent Claim 89 words
Mixtures of anionic oligomeric esters according to claim 4 wherein the weight ratio of esters having formula I and esters having formula II is from about 30:1 to about 1:1 and wherein the molar ratio of R substituents being --CH 2 CH 2 -- substituents to R substituents being --CH 2 CH(CH 3 )-- and --CH(CH 3 )CH 2 -- substituents is from about 0:1 to about 0.7:0.3 and wherein at least 2% by weight of the esters having formula I or II contain at least 4 ##STR34## units.
Claim 10
Dependent Claim 33 words
A laundering and fabric care composition comprising from about 0.1% to about 50% by weight of a soil release component comprising anionic oligomeric esters and mixtures of anionic oligomeric esters of claim 1.
Claim 11
Dependent Claim 56 words
A detergent composition comprising from about 1% to about 50% by weight of a detersive surfactant selected from the group consisting of anionic surfactants, cationic surfactants, nonionic surfactants, zwitterionic surfactants and mixtures thereof, and from about 0.1% to about 50% by weight of anionic oligomeric esters or mixtures of anionic oligomeric esters according to claim 1.
Claim 12
Dependent Claim 19 words
A detergent composition according to claim 10 wherein the detersive surfactant component comprises at least one anionic detersive surfactant.
Claim 13
Dependent Claim 14 words
A composition according to claim 10 which is formulated as a liquid laundry detergent.
Claim 14
Dependent Claim 34 words
A composition according to claim 9 which is formulated as a bar, powder, granule, tablet or flowable gel, or is releasably contained in pouch or sheet form or in or upon other carrier substrate.
Claim 15
Dependent Claim 34 words
A composition according to claim 10 which is formulated as a bar, powder, granule, tablet or flowable gel, or is releasably contained in pouch or sheet form or in or upon other carrier substrate.
Claim 16
Dependent Claim 56 words
A detergent composition comprising from about 1% to about 30% by weight of a detersive surfactant selected from the group consisting of anionic surfactants, cationic surfactants, nonionic surfactants, zwitterionic surfactants and mixtures thereof and from about 0.1% to about 4% by weight of anionic oligomeric esters or mixtures of anionic oligomeric esters according to claim 4.
Claim 17
Dependent Claim 56 words
A detergent composition comprising from about 1% to about 30% by weight of a detersive surfactant selected from the group consisting of anionic surfactants, cationic surfactants, nonionic surfactants, zwitterionic surfactants and mixtures thereof and from about 0.1% to about 4% by weight of anionic oligomeric esters or mixtures of anionic oligomeric esters according to claim 8.
Claim 18
Dependent Claim 541 words
A heavy-duty liquid detergent composition comprising, by weight: (a) from about 10% to about 35% of an anionic surfactant on an acid basis; (b) from 0% to about 15% of an ethoxylated nonionic surfactant of the formula R 1 (OC 2 H 4 ) j OH, wherein R 1 is a C 10 -C 16 alkyl group or a C 8 -C 12 alkyl phenyl group, j averages from about 3 to about 9, and said nonionic surfactant has an HLB of from about 10 to about 13; (c) from about 0% to about 15% of a cosurfactant selected from the group consisting of: (i) quaternary ammonium surfactants having the formula: [R.sup.2 (OR.sup.3).sub.y ][R.sup.4 (OR.sup.3).sub.y ].sub.2 R.sup.5 N.sup.+ X.sup.- wherein R 2 is an alkyl or alkyl benzyl group having from about 6 to about 16 carbon atoms in the alkyl chain; each R 3 is selected from the group consisting of --CH 2 CH 2 --, --CH 2 CH(CH 3 )--, --CH(CH 3 )CH 2 --, --CH 2 CH(CH 2 OH)--, --CH 2 CH 2 CH 2 --, and mixtures thereof; each R 4 is selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, benzyl, and hydrogen when y is not 0; R 5 is the same as R 4 or is an alkyl chain wherein the total number of carbon atoms of R 2 plus R 5 is from about 8 to about 16; each y averages from 0 to about 10 and the sum of the y values is from 0 to about 15; and X is any compatible anion; (ii) amine surfactants having the formula: [R.sup.2 (OR.sup.3).sub.y ][R.sup.4 (OR.sup.3).sub.y ]R.sup.5 N wherein R 2 , R 3 , R 4 , R 5 and y are as defined above; (iii) amine oxide surfactants having the formula: [R.sup.2 (OR.sup.3).sub.y ][R.sup.4 (OR.sup.3).sub.y ]R.sup.5 N→O wherein R 2 , R 3 , R 4 , R 5 and y are as defined above; (iv) an amide surfactant of the formula: ##STR35## wherein R 6 is an alkyl, hydroxyalkyl or alkenyl radical containing from about 8 to about 20 carbon atoms, and R 7 and R 8 are each selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, and wherein said radicals additionally contain up to about 5 ethylene oxide units; and (v) mixtures thereof; (d) from about 5% to about 30% of detergent builder; (e) a neutralization system; (f) an aqueous solvent system; (g) from about 0.1% to about 5.0% of anionic oligomeric soil release esters having the formula ##STR36## wherein all R substituents are independently selected from --CH 2 CH 2 --, --CH 2 CH(CH 3 )-- and --CH(CH 3 )CH 2 --, n is an integer from 2 to 15 or is a number from 2 to 15 representing an average degree of ethoxylation, x is the average degree of polymerization of the ester backbone ##STR37## and is a number between 0.3 and 7; and E is a mixture of the substituents ##STR38## provided that at least 0.5 mole fraction of said E substituents are ##STR39## substituents and further provided that at least 0.1 mole fraction of the total of all R substituents are 1,2-propylene substituents.
Claim 19
Dependent Claim 541 words
A heavy-duty liquid detergent composition comprising, by weight: (a) from about 10% to about 35% of an anionic surfactant on an acid basis; (b) from 0% to about 15% of an ethoxylated nonionic surfactant of the formula R 1 (OC 2 H 4 ) j OH, wherein R 1 is a C 10 -C 16 alkyl group or a C 8 -C 12 alkyl phenyl group, j averages from about 3 to about 9, and said nonionic surfactant has an HLB of from about 10 to about 13; (c) from about 0% to about 15% of a cosurfactant selected from the group consisting of: (i) quaternary ammonium surfactants having the formula: [R.sup.2 (OR.sup.3).sub.y ][R.sup.4 (OR.sup.3).sub.y ].sub.2 R.sup.5 N.sup.+ X.sup.- wherein R 2 is an alkyl or alkyl benzyl group having from about 6 to about 16 carbon atoms in the alkyl chain; each R 3 is selected from the group consisting of --CH 2 CH 2 --, --CH 2 CH(CH 3 )--, --CH(CH 3 )CH 2 --, --CH 2 CH(CH 2 OH)--, --CH 2 CH 2 CH 2 --, and mixtures thereof; each R 4 is selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, benzyl, and hydrogen when y is not 0; R 5 is the same as R 4 or is an alkyl chain wherein the total number of carbon atoms of R 2 plus R 5 is from about 8 to about 16; each y averages from 0 to about 10 and the sum of the y values is from 0 to about 15; and X is any compatible anion; (ii) amine surfactants having the formula: [R.sup.2 (OR.sup.3).sub.y ][R.sup.4 (OR.sup.3).sub.y ]R.sup.5 N wherein R 2 , R 3 , R 4 , R 5 and y are as defined above; (iii) amine oxide surfactants having the formula: [R.sup.2 (OR.sup.3).sub.y ][R.sup.4 (OR.sup.3).sub.y ]R.sup.5 N→O wherein R 2 , R 3 , R 4 , R 5 and y are as defined above; (iv) an amide surfactant of the formula: ##STR35## wherein R 6 is an alkyl, hydroxyalkyl or alkenyl radical containing from about 8 to about 20 carbon atoms, and R 7 and R 8 are each selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, and wherein said radicals additionally contain up to about 5 ethylene oxide units; and (v) mixtures thereof; (d) from about 5% to about 30% of detergent builder; (e) a neutralization system; (f) an aqueous solvent system; (g) from about 0.1% to about 5.0% of anionic oligomeric soil release esters having the formula ##STR36## wherein all R substituents are independently selected from --CH 2 CH 2 --, --CH 2 CH(CH 3 )-- and --CH(CH 3 )CH 2 --, n is an integer from 2 to 15 or is a number from 2 to 15 representing an average degree of ethoxylation, x is the average degree of polymerization of the ester backbone ##STR37## and is a number between 0.3 and 7; and E is a mixture of the substituents ##STR38## provided that at least 0.5 mole fraction of said E substituents are ##STR39## substituents and further provided that at least 0.1 mole fraction of the total of all R substituents are 1,2-propylene substituents.
Claim 20
Dependent Claim 69 words
A detergent composition according to claim 17 comprising anionic oligomeric soil release esters wherein at least 0.95 mole fraction of the E substituents are ##STR40## wherein the average degree of ethoxylation, n, is greater than 2; wherein the average degree of polymerization of the ester backbone, x, is at least about 1.75; and wherein at least 0.33 mole fraction of the total of all R substituents are 1,2-propylene substituents.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1991-01-25 1991-07-27 1992-01-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1995-01-25 1995-07-27 1996-01-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1999-01-25 1999-07-27 2000-01-26 $7700.00 Window Closed / Lapsed

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