EP0354856A2 - Weichspülerzusammensetzungen und Verfahren zu deren Herstellung und Verwendung - Google Patents

Weichspülerzusammensetzungen und Verfahren zu deren Herstellung und Verwendung Download PDF

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Publication number
EP0354856A2
EP0354856A2 EP89402291A EP89402291A EP0354856A2 EP 0354856 A2 EP0354856 A2 EP 0354856A2 EP 89402291 A EP89402291 A EP 89402291A EP 89402291 A EP89402291 A EP 89402291A EP 0354856 A2 EP0354856 A2 EP 0354856A2
Authority
EP
European Patent Office
Prior art keywords
fabric softening
cationic
softening composition
composition
softening
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP89402291A
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English (en)
French (fr)
Other versions
EP0354856A3 (de
Inventor
Norman Blumenkopf
Jean-Paul Grandmaire
Alain Jacques
Viviane Tack
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Colgate Palmolive Co
Original Assignee
Colgate Palmolive Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Publication of EP0354856A2 publication Critical patent/EP0354856A2/de
Publication of EP0354856A3 publication Critical patent/EP0354856A3/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid

Definitions

  • the invention relates to fabric softening compositions adapted to be used in the rinse cycle of an automatic dishwashing machine. More particularly, this invention is concerned with aqueous fabric softening compositions which impart improved softness and other desirable attributes such as better rewettability to the compositions. Specifically, the invention is based on the combination of a cationic softener and a unique class of polysiloxanes.
  • compositions containing quaternary ammonium salts having at least one long chain hydrocarboxyl group such as distearyl dimethyl ammonium chloride or longchain imidazolinium salts are commonly used to provide fabric softening benefits when employed in an laundry rinse operation; for example, see U.S. Patents 3,349,033; 3,644,203; 3,946,115; 3,997,453; 4,073,735; and 4,119,545, among many others.
  • the quaternary ammonium compounds while they are salts, are nevertheless generally characterized as water-insoluble since their solubility in water under normal conditions is less than about 5% by weight.
  • the usual concentration used by the consumer and accepted as the "standard” is 6% by weight.
  • these cationic salts are generally present as "sols" or dispersions, and stability becomes a major problem. See for example U.S. Patent 4,426,299 col. 1, lines 11 to 22.
  • stability and viscosity problems become major ones at higher concentrations e.g. above about 7% by weight of the cationic.
  • cationic softening compositions particularly for use in the rinse cycle of a clothes washing machine, which are of improved softening not only at equal concentrations with older formulations, but even at lower concentrations.
  • This concept is not new as evidenced e.g. by U.S. Patent 4,000,077 to Wixon wherein cationic quaternary softener is combined with alcohol or alcohol ether sulfate.
  • This patent also demonstrates that with improved softening, another plus is achieved in terms of enhanced whiteness, the latter often being adversely affected by cationics.
  • silicone-based composition for treating fibers or yarns and textiles to soften them. See, in this regard, an article in Colorage - June 29, 1972 entitled “Silicones in the Textile Industry” by M.J. Pald p 46 and 53. Also attention is directed to U.S. Patents 3,968,042 and 4,020,212 wherein compositions or organo polysiloxane (and predominantly a poly [dimethyl siloxane]) with a cationic softening surfactant (e.g. distearyl dimethyl ammonium chloride) or conventional imidazolinium softener (Varisoft 475) are described for the treatment of polyolefin fibers.
  • the organo polysiloxanes are liquid, water-dispersible products with viscosities ranging from "about 100 to about 400" cps at 77° F (25°C).
  • silicones are siloxanes with viscosities at 25°C of "at least 100 centistokes and up to 8000 centistokes". While this patent appears limited to siloxanes with viscosities not above 8000 centistokes, disclosures of higher viscosities (e.g. up to 170000 centistokes) are given, but data is given allegedly establishing optimum performance in the range of 3000 to 8000 cs. (Ex. I).
  • improved softening compositions are provided by a combination of a cationic softener or mixture of cationic softeners or mixtures of cationics with anionics (e.g. alcohol sulfates or alcohol ether sulfates) and/or non-ionics (e.g. fatty alcohols, fatty acid esters), and the like, with a cross-linked polysiloxane.
  • anionics e.g. alcohol sulfates or alcohol ether sulfates
  • non-ionics e.g. fatty alcohols, fatty acid esters
  • the liquids may have viscosities in the range of less than about 100 to several hundred to several thousand to the tens of thousands and up to where it becomes unmeasurable; the preferred polysiloxanes have viscosities about 10,000 cs (25°C) up to elastomeric types (i.e. no measurable viscosity).
  • compositions of this invention not only give superior softening, but quite unexpectedly yield treated textiles with improved rewettability.
  • the cationic softeners tend to provide fabrics with a degree of water-resistance or in other words these softeners tend to render the fabric somewhat hydrophobic.
  • Silicones or polysiloxanes also would be expected to increase the hydrophobicity of fabrics treated with them as described in British 1,549,180. Notwithstanding such teachings and expectations it has now been discovered that the compositions of this invention not only provide improved and outstanding softening of textiles especially in the rinse cycle of a washing machine but only do so without increasing the hydrophobicity of the textile. As a matter of fact the goods exhibit improved wettability.
  • the cationics which are usefull herein include the entire class of quaternary ammonium compounds which may, only in part, be represented by the following general formulas . wherein at least one of the R groups and preferably two (e.g. R & R1) represents an aliphatic from 12 to 30 carbon atoms and the other R groups (e.g. R2 & R3) may be lower aliphatic e.g. from C1 to C8 preferably C1 to C4 and preferably, alkyl or aralkyl as methyl, ethyl and propyl or benzyl.
  • the "other" R groups i.e.
  • R2 & R3 may also together with the nitrogen and/or one or more other heteroatoms and (preferably nitrogen) form a 5 - or 6 ⁇ membered heterocyclic ring and
  • X ⁇ is any anion, e.g. halo, sulfate, methyl sulfate, nitrate, acetate, phosphate, benzoate, oleate, etc.
  • the symbol "a” represents the ionic valance of the anion and also, therefore, the number of quaternary cationic moieties in association therewith.
  • Typical compounds of the foregoing formula I include ethyl-dimethyl-stearyl ammonium chloride, cetyl-dimethyl-benzyl ammonium chloride, dimethyl distearyl ammonium chloride, benzyl-dimethyl-stearyl ammonium chloride, benzyl-dimethyl-stearyl ammonium bromide, trimethyl-stearyl ammonium chloride, trimethyl-cetyl ammonium bromide, diethyldistearyl ammonium chloride, diethyl-octyl-stearyl ammonium chloride, dimethyl-ethyl-lauryl ammonium chloride, dimethyl-methylethyl-lauryl-cetyl ammonium chloride, propyl myristyl ammonium chloride, ditallow-dimethyl ammonium chloride, and the corresponding methosulfates, acetates, etc.
  • R4 groups represent independently hydrogen or C1 to C4 alkyl with hydrogen being preferred;
  • R5 represents aliphatic, preferably alkyl or acyloxyalkyl of C8 to C30 and more preferably alkyl of C13 to C22;
  • R6 represents aliphatic, preferably C1 to C4 alkyl and more preferably methyl or ethyl;
  • R7 may be selected as R5, the same or different, or may be lower alkyl or substituted alkyl of C1 to C4 such as haloalkyl, hydroxyalkyl, aminoalkyl, alkylaminoalkyl, acylaminoalkyl and the like;
  • X ⁇ is any anion similar to the formula I quaternary anions;
  • the more preferred compounds of formula II are the acylaminoethyl compounds of the formula where R5, R6, (a) and (b) are as defined for Formula
  • Illustrative compounds of Formulas II and IIa include; 2-heptadecyl-1-methyl-1-oleylamidoethyl imidazolinium ethosulfate 2-heptadecyl-1-methyl-1-(2-stearoylamido)e-thylimidazolinium sulfate, 2-heptadecyl-1-methyl-1-(2-stearoylamido)e-thylimidazolinium chloride, 2-coco-1-(2-hydroxyethyl)-1-benzyl imidazolonium chloride, 2-coco-1-(hydroxyethyl)-1-(4-chlorobutyl)-imidazolinium chloride, 2-coco-1-(2-hydroxyethyl)-1-octadecenyl imidazolinium chloride 2-tall oil fatty-1-(2-hydroxyethyl)-1-benzyl imidazolinium chloride, 2-tall oil fatty-1-(2-hydroxyethyl
  • R group is selected from C10 to C30 aliphatic, preferably alkyl or alkenyl; or RO-(CH2) n - where R has same meaning as above, i.e. C10 to C30 aliphatic and preferably alkyl or alkenyl; the R1's may be hydrogen; C1 to C4 alkyl or hydroxyalkyl groups; n is an integer of 2 to 6 and m is an integer from 1 to 5; and X is as defined in Formula (A).
  • the preferred com­pounds are those where R is C12 to C18 and R1 is lower alkyl, especially methyl.
  • N-Tallowyl-N,N,N1,N1-tetramethyl-1,3-propanediammonium dimethosulfate N-Tallowyl-N,N1,N1-trimethyl-1,3-propanediammonium dimethosulfate, N-Oleyl-N,N,N1,N1,N1-pentamethyl-1,3-propanediammonium dimethosulfate
  • N-stearyl-N,N,N1,N1,N1-pentamethyl-1,3-propanediammonium dimethosulfate N-stearyloxypropyl-N,N1,N1tris(3-hydroxypropyl)-1, 3-propanediammonium dimethosulfate
  • the cross-linked polysiloxanes which may be used are generally represented by a reticulated structure comprising the following units: wherein R represents alkyl, particularly lower (C1 to C4 alkyl), substituted alkyl (e.g. with alkoxy, amino, halo etc...), aralkyl (e.g. benzyl) and the like; the preferred R group is methyl, the "M” unit comprises from 0 to about 10% (e.g. 0%, 2%, 5%) of the number of units. The "D” unit from about 20 to about 95% of the number of units and the "T” unit from about 2 to about 80%.
  • R represents alkyl, particularly lower (C1 to C4 alkyl), substituted alkyl (e.g. with alkoxy, amino, halo etc...), aralkyl (e.g. benzyl) and the like; the preferred R group is methyl, the "M” unit comprises from 0 to about 10% (e.g. 0%,
  • Preferred ranges are 0 to 5% for "M” units; about 40% to about 80% “D” units; and about 10% to about 60% “T” units. Most preferred are ranges of 0% to less than 5% (e.g. 1%, 2% or 3%) of "M” units; 60 to 80% “D” units; and about 20% to about 40% “T” units.
  • m, n, and p represent integers expressing the relative content of the "M", "D” and “T” units respectively.
  • compositions of this invention are readily prepared in the usual 6 - 8% active ingredient level which is the customary one for the reasons advanced above. It is quite apparent that higher levels may be used resorting to the techniques of the prior art and, as demonstrated earlier, levels up to 60% by weight of active ingredients are readily obtained. Regardless, however, of the level of active ingredients, of more significance in achieving the maximum benefits of this invention is the ratio of cationic softener to polysiloxane. Ratios of cationic to polysiloxane may range from about 100:1 to about 1:10 with ratio from about 15:1 to 1:10 being preferred; 7:1 to 1:7 more preferred, 5:1 to 1:5 more highly preferred with outstanding results achievable at ratios of 5:1, 2:1, 1:1, 1:2 and 1:5.
  • viscosity preferences the range of from about 10,000 up to about 100,000 (e.g. 60,000 cps) is outstanding for softening, but also, up to and above 1,000,000 cps is equally useful.
  • elastomeric products which have, one might say, infinite viscosity. They are not only outstanding softeners but also impart rewettability characteristics which are even better than those given by the lower viscosity materials.
  • an alcohol sulfate e.g. softener adjuvets or otherwise for example, C16 to C18 alcohol sulfate
  • an alcohol ether sulfate e.g. C16 to C18 alcohol and 2 or 3 or 4 moles of ethylene oxide and then sulfated
  • sodium paraffin e.g. C16 to C18
  • non-ionic material such as paraffins, fatty acid ester glycol and glyceryl esters, a fatty alcohol e.g.
  • auxiliary materials may be present in a cationic to auxiliary ratio of about 20:1 to 1:5 preferably from about 15:1 to 1:1 and more preferably 10:1 to 3:1.
  • the composition may contain the usual adjuvants of perfume, color opacifiers (e.g. resin emulsions), sequestrant, viscosity control agents such as inorganic salts i.e. sodium nitrate, sodium chloride, calcium chloride and the like, solubilizers e.g. hydrotropes, etc...
  • a particularly preferred additional component is represented by the general class of high molecular weight alcohols and especially the fatty alcohols of C8 to C30, typically C12 to C20 such as n-dodecyl alcohol, n-tetradecylalcohol, oxo-tridecylalcohol, n-hexadecylalcohol, n-octadecyl alcohol, eicosyl alcohol, and mixed fatty alcohols of synthetic or natural derivation e.g. stearyl alcohol.
  • An especially preferred ratio of cationic to fatty alcohol ranges from 6:1 to 2:1 and more preferred 5:1 to 3:1 and most preferred 4.5:1 to 3.5:1 (e.g. 4:1).
  • a softening composition of the following components is provided % Ditallow dimethyl ammonium chloride 3.6 C16 - C18 fatty alcohol 0.9 Siloxane (cross-linked X2-7589) 0.5
  • the softening evaluation tests may be run according to a conventional laboratory procedure using six times hardened cotton terry cloth towels at a dosage of 110 ml/wash with 8 replicates or in a standard washing machine with terry cloth towels.
  • the rewettability is determined by partially immersing thin, treated strips of cloth into a column of water and measuring the wicking height of the liquid.
  • Example I is repeated using the following cationics and amounts thereof in place of the DTDMAC (3.6%) % (a) DTDMAC (4.0%) (b) DTDMAC (3.2%) (c) Dimethyl distearyl ammonium methosulfate (3.6%) (d) 2-heptodecyl-1-methyl-1-olylamidothyl imidazolinium ethosulfate (3.6%)
  • Example I and II(a) to II(e) is repeated replacing the mixed C16 - C18 fatty alcohol with the following non-ionics in the indicated amounts % (a) hexadecyl alcohol (0.9%) (b) octadecyl alcohol (0.9%) (c) glyceryl monostearate (0.9%) (d) C16 - C18 fatty alcohol (1.2%)
  • Example I test sample gives a wicking height of 44.8 mm whereas in this example the test sample goes only 35.4 mm. A difference of 3.5 mm in test results is considered significant.
  • Example I and II are repeated except that the fatty alcohol is eliminated and in the case of Example II(a) and II(b) the level of cationic is raised 30%. Excellent results are obtained.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
EP89402291A 1988-08-12 1989-08-11 Weichspülerzusammensetzungen und Verfahren zu deren Herstellung und Verwendung Withdrawn EP0354856A3 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US23234688A 1988-08-12 1988-08-12
US232346 1988-08-12

Publications (2)

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EP0354856A2 true EP0354856A2 (de) 1990-02-14
EP0354856A3 EP0354856A3 (de) 1990-05-02

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ID=22872742

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EP89402291A Withdrawn EP0354856A3 (de) 1988-08-12 1989-08-11 Weichspülerzusammensetzungen und Verfahren zu deren Herstellung und Verwendung

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EP (1) EP0354856A3 (de)
JP (1) JPH02154069A (de)
AU (1) AU616990B2 (de)
BR (1) BR8904038A (de)
DK (1) DK395589A (de)
GR (1) GR1000488B (de)
MX (1) MX170216B (de)
MY (1) MY105007A (de)
NZ (1) NZ230238A (de)
PH (1) PH27205A (de)
PT (1) PT91429A (de)
TR (1) TR24991A (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5064543A (en) * 1990-06-06 1991-11-12 The Procter & Gamble Company Silicone gel for ease of ironing and better looking garments after ironing
US5336419A (en) * 1990-06-06 1994-08-09 The Procter & Gamble Company Silicone gel for ease of ironing and better looking garments after ironing
WO1995024460A1 (en) * 1994-03-11 1995-09-14 The Procter & Gamble Company Fabric softener compositions
US5532023A (en) * 1994-11-10 1996-07-02 The Procter & Gamble Company Wrinkle reducing composition
WO1996033303A1 (en) * 1995-04-21 1996-10-24 Danaklon A/S Rewettable polyolefin fibres
US5741765A (en) * 1995-02-23 1998-04-21 Lever Brothers Company, Division Of Conopco, Inc. Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant
GB2318364A (en) * 1996-10-21 1998-04-22 Kao Corp Personal cleansing composition containing a glycerol derivative
US5798107A (en) * 1994-11-10 1998-08-25 The Procter & Gamble Company Wrinkle reducing composition
US7060666B2 (en) 2002-05-27 2006-06-13 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Fabric conditioning composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115023486A (zh) * 2019-12-30 2022-09-06 美国陶氏有机硅公司 阳离子表面活性剂及其制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB991597A (en) * 1960-05-25 1965-05-12 Wallace Cameron & Co Ltd Improvements in or relating to detergent solutions
US4128484A (en) * 1975-07-14 1978-12-05 The Procter & Gamble Company Fabric softening compositions
DE2631114C3 (de) * 1975-07-14 1981-11-26 The Procter & Gamble Co., 45202 Cincinnati, Ohio Weichmachungsmittel für Gewebe
DE2631419A1 (de) * 1975-07-16 1977-02-03 Procter & Gamble Europ Zusammensetzungen fuer die textilbehandlung
GB1549180A (en) * 1975-07-16 1979-08-01 Procter & Gamble Textile treating compositions
DE3427496A1 (de) * 1984-07-26 1986-01-30 Henkel KGaA, 4000 Düsseldorf Verfahren zur herstellung eines polysiloxan-blockpolymerisates

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5064543A (en) * 1990-06-06 1991-11-12 The Procter & Gamble Company Silicone gel for ease of ironing and better looking garments after ironing
US5336419A (en) * 1990-06-06 1994-08-09 The Procter & Gamble Company Silicone gel for ease of ironing and better looking garments after ironing
WO1995024460A1 (en) * 1994-03-11 1995-09-14 The Procter & Gamble Company Fabric softener compositions
US5532023A (en) * 1994-11-10 1996-07-02 The Procter & Gamble Company Wrinkle reducing composition
US5798107A (en) * 1994-11-10 1998-08-25 The Procter & Gamble Company Wrinkle reducing composition
US5741765A (en) * 1995-02-23 1998-04-21 Lever Brothers Company, Division Of Conopco, Inc. Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant
WO1996033303A1 (en) * 1995-04-21 1996-10-24 Danaklon A/S Rewettable polyolefin fibres
GB2318364A (en) * 1996-10-21 1998-04-22 Kao Corp Personal cleansing composition containing a glycerol derivative
US6008183A (en) * 1996-10-21 1999-12-28 Kao Corporation Detergent composition
GB2318364B (en) * 1996-10-21 2000-09-13 Kao Corp Detergent composition
US6265372B1 (en) 1996-10-21 2001-07-24 Kao Corporation Detergent composition
US7060666B2 (en) 2002-05-27 2006-06-13 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Fabric conditioning composition

Also Published As

Publication number Publication date
PT91429A (pt) 1990-03-08
NZ230238A (en) 1991-10-25
BR8904038A (pt) 1990-03-20
DK395589D0 (da) 1989-08-11
PH27205A (en) 1993-05-04
DK395589A (da) 1990-02-13
GR890100506A (en) 1990-08-22
MX170216B (es) 1993-08-11
AU3941189A (en) 1990-02-15
AU616990B2 (en) 1991-11-14
TR24991A (tr) 1992-08-21
EP0354856A3 (de) 1990-05-02
GR1000488B (el) 1992-07-30
MY105007A (en) 1994-07-30
JPH02154069A (ja) 1990-06-13

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