Patent US4721580A successfully refreshed from Google Patents.
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
•
Filing: 1987-01-07
•
Granted: 1988-01-26
•
Expires: 2007-01-07
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.
References Cited (Backward Citations)
US3416952A
Cited
GB1161668A
Cited
US3512920A
Cited
US3639352A
Cited
US4161577A
Cited
US3712873A
Cited
US3893929A
Cited
US3821169A
Cited
US3823185A
Cited
US4132680A
Cited
US4156073A
Cited
US4116885A
Cited
CA1100262A
Cited
US4238531A
Cited
US4427557A
Cited
US4598141A
Cited
US4525524A
Cited
EP0185427B1
Cited
EP0194127A2
Cited
GB2172608A
Cited
EP0199403B1
Cited
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 |