WO1998012292A1 - Fabric softeners having increased performance - Google Patents

Fabric softeners having increased performance Download PDF

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Publication number
WO1998012292A1
WO1998012292A1 PCT/US1997/016688 US9716688W WO9812292A1 WO 1998012292 A1 WO1998012292 A1 WO 1998012292A1 US 9716688 W US9716688 W US 9716688W WO 9812292 A1 WO9812292 A1 WO 9812292A1
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WO
WIPO (PCT)
Prior art keywords
mixtures
formula
alkyl
cationic charge
weight
Prior art date
Application number
PCT/US1997/016688
Other languages
French (fr)
Inventor
Ellen Schmidt Baker
Frederick Anthony Hartman
Errol Hoffman Wahl
Mark Robert Sivik
Lucille Florence Taylor
Original Assignee
The Procter & Gamble Company
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.)
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=21831841&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1998012292(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to EP97941708A priority Critical patent/EP0931131B1/en
Priority to CA002265731A priority patent/CA2265731A1/en
Priority to JP51491198A priority patent/JP3190357B2/en
Priority to DE69728778T priority patent/DE69728778D1/en
Priority to CZ99945A priority patent/CZ94599A3/en
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AT97941708T priority patent/ATE264903T1/en
Priority to BR9712068A priority patent/BR9712068A/en
Priority to US09/269,087 priority patent/US6083899A/en
Priority to AU43562/97A priority patent/AU734821B2/en
Publication of WO1998012292A1 publication Critical patent/WO1998012292A1/en
Priority to NO991201A priority patent/NO991201L/en

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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
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
    • 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
    • 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
    • C11D3/3723—Polyamines or polyalkyleneimines
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3776—Heterocyclic compounds, e.g. lactam

Definitions

  • fabric softener compositions which have an increased or "boosted” fabric softening capacity.
  • fabric softener compositions which comprise fabric softener actives having suitable properties other than sufficient cationic charge density, need a means to boost the overall charge density thereby providing to the consumer a better fabric care benefit.
  • the cationic charge enhancing agents of the present invention have the effect of increasing the net cationic charge concentration independent of the intrinsic properties of the softener active. Therefore, the formulator may combine fabric softener actives having low cationic charge capacity, but which have other desirable properties inter alia good dispensability, low melting point, with cationic charge boosters thereby obtaining a composition which overcomes the lack of cationic charge density of the fabric softener active.
  • X is a softener compatible anion; m is from 1 to 3; n is from 1 to 4; at least one cationic charge booster selected from the group consisting of: i) at least about 0.2%, preferably from about 0.2% to about 10%, more preferably from about 0.2% to about 6% by weight, of a cationic charge booster having the formula:
  • R 1 , R-, R 3 . and R 4 are each independently C 1 -C22 alkyl, C3-C22 alkenyl.
  • R 5 -Q-(CH ) m - wherein R 5 is Cj - C22 alkyl, C3-C22 alkenyl, and mixtures thereof, m is from 1 to about 6;
  • Q is a carbonyl unit as defined hereinabove;
  • X is a softener compatible anion; ii) at least about 0.2%, preferably from about 0.2% to about 5%, more preferably from about 0.2% to about 2% by weight, of a cationic charge booster having the formula:
  • the preferred fabric softening actives according to the present invention have the formula:
  • each R is independently Cj-C ⁇ alkyl, C ⁇ -C hydroxyalkyl, benzyl, and mixtures thereof;
  • Rl is preferably C ⁇ 1-C22 alkyl, C ⁇ 1-C22 alkenyl, and mixtures thereof;
  • Q is a carbonyl moiety having the formula:
  • O — O— C-Rl is a fatty acyl moiety.
  • Suitable fatty acyl moieties for use in the softener actives of the present invention are derived from sources of triglycerides including tallow, vegetable oils and/or partially hydrogenated vegetable oils including inter alia canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil.
  • mixed chain fatty acyl units is defined as "a mixture of fatty acyl units comprising alkyl and alkenyl chains having from 10 carbons to 22 carbon atoms including the carbonyl carbon atom, and in the case of alkenyl chains, from one to three double bonds, preferably all double bonds in the cis configuration".
  • R units of the present invention it is preferred that at least a substantial percentage of the fatty acyl groups are unsaturated, e.g., from about 25%, preferably from about 50% to about 70%, preferably to about 65%.
  • the total level of fabric softening active containing polyunsaturated fatty acyl groups can be from about 3%, preferably from about 5%, more preferably from about 10% to about 30%, preferably to about 25%, more preferably to about 18%.
  • cis and trans isomers can be used, preferably with a cis/ trans ratio is of from 1 : 1, preferably at least 3:1, and more preferably from about 4:1 to about 50:1, more preferably about 20:1, however, the minimum being 1 :1.
  • the R units suitable for use in the present invention can be further characterized by the Iodine Value (IV) of the parent fatty acid, said IV is preferably from about 20, more preferably from about 50, most preferably from about 70, to a value of about 140, preferably to about 130, more preferably to about 115.
  • IV is preferably from about 20, more preferably from about 50, most preferably from about 70, to a value of about 140, preferably to about 130, more preferably to about 115.
  • formulators may wish to add an amount of fatty acyl units which have Iodine Values outside the range listed herein above.
  • "hardened stock" (IV less than or equal to about 10) may be combined with the source of fatty acid admixture to adjust the properties of the final softener active.
  • a further preferred embodiment of the present invention comprises DEQA's wherein the average Iodine Value for Rl is approximately 45.
  • R moieties which are introduced during the quaternization step are preferably methyl.
  • R moieties which are introduced during the quaternization step are preferably methyl.
  • R is preferably the same moiety (i.e. methyl) which is introduced during the quaternization step.
  • a methyl amine having the formula:
  • Gte '3-m-N-KCHzfo-Z m wherein not all of the Z units are fully reacted with a fatty acyl moiety thereby leaving an amount of ami ⁇ e and/or quatemized ammonium compound in the final fabric softener active admixture having one or more Z units unreacted and thereby not transformed into an ester or amide.
  • N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride where the tallow chains are at least partially unsaturated and N,N-di(canoloyl-oxy-ethyl)-N,N-dimethyl ammonium chloride.
  • the amount of fabric softening active present in the compositions of the present invention is at least about 2%, preferably from about 2%, more preferably from about 5% to about 60%, more preferably to about 40% by weight, of the composition.
  • Cationic Charge Boosters The preferred cationic charge boosters of the present invention are described herein below. i) Quaternary Ammonium Compounds
  • Rl, R2, R3, and R ⁇ are each independently C1-C22 alkyl, C3-C22 alkenyl, R5-Q-(CH2) m -, wherein R- ⁇ is C1-C22 alkyl, and mixtures thereof, m is from 1 to about 6;
  • X is an anion.
  • R is C6-C22 alkyl, Cg-C22 alkenyl, and mixtures thereof, more preferably C ⁇ J -CJ S lkyl > j-Cjg alkenyl, and mixtures thereof;
  • R 2 , R 3 , and R 4 are each preferably C1-C4 alkyl, more preferably each R2, R3 ? and R 4 are methyl.
  • the formulator may similarly choose R to be a R5-Q-(CH2) m - moiety wherein R$ is an alkyl or alkenyl moiety having from 1 to 22 carbon atoms, preferably the alkyl or alkenyl moiety when taken together with the Q unit is an acyl unit derived preferably derived from a source of triglyceride selected from the group consisting of tallow, partially hydrogenated tallow, lard, partially hydrogenated lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, co oil, soybean oil, tall oil, rice bran oil, etc. and mixtures thereof.
  • R$ is an alkyl or alkenyl moiety having from 1 to 22 carbon atoms, preferably the alkyl or alkenyl moiety when taken together with the Q unit is an acyl unit derived preferably derived from a source of triglyceride selected from the group consisting of
  • X is a softener compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and mixtures thereof, more preferably chloride and methyl sulfate.
  • a strong acid for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and mixtures thereof, more preferably chloride and methyl sulfate.
  • a preferred composition according to the present invention contains at least about 0.2%, preferably from about 0.2% to about 5%, more preferably from about 0.2% to about 2% by weight, of one or more poly vinyl amines having the formula
  • y is from about 3 to about 10,000, preferably from about 10 to about 5,000, more preferably from about 20 to about 500.
  • Polyvinyl amines suitable for use in the present invention are available from BASF.
  • one or more of the polyvinyl amine backbone -NH2 unit hydrogens can be substituted by an alkyleneoxy unit having the formula:
  • Rl is C2-C4 alkyiene
  • R is hydrogen, C1-C4 alkyl, and mixtures thereof
  • x is from 1 to 50.
  • the polyvinyl amine is reacted first with a substrate which places a 2-propyleneoxy unit directly on the nitrogen followed by reaction of one or more moles of ethylene oxide to form a unit having the general formula:
  • x has the value of from 1 to about 50. Substitutions such as the above are represented by the abbreviated formula PO-EO x -. However, more than one propyleneoxy unit can be incorporated into the alkyleneoxy substituent.
  • the compounds of the present invention comprise polyamines having a ratio of m : n that is at least 1:1 but may include linear polymers (n equal to 0) as well as a range as high as 10:1, preferably the ratio is 2:1.
  • the ratio of m:n is 2:1, the ratio of primary secondary :tertary amine moieties, that is the ratio of -RNH2, -RNH, and -RN moieties, is 1 :2:1.
  • R units are C2 ⁇ C alkyiene, C -Cg alkyl substituted alkyiene, and mixtures thereof, preferably ethylene, 1 ,2-propylene, 1 ,3-propylene, and mixtures thereof, more preferably ethylene.
  • R units serve to connect the amine nitrogens of the backbone.
  • one or more of the polyvinyl amine backbone -NH2 unit hydrogens can be substituted by an alkyleneoxy unit having the formula: — (RlO) x R2 wherein Rl is C2-C4 alkyiene, R is hydrogen, C1-C4 alkyl, and mixtures thereof; x is from 1 to 50.
  • the polyvinyl amine is reacted first with a substrate which places a 2-propyleneoxy unit directly on the nitrogen followed by reaction of one or more moles of ethylene oxide to form a unit having the general formula:
  • ethanolamine may be used as an "initiator" in the synthesis of polyethyleneimines, therefore a sample of polyethyleneimine that comprises one hydroxyethyl moiety resulting from the polymerization "initiator” would be considered to comprise a homogeneous polyamine backbone for the purposes of the present invention.
  • the PEI's which comprise the preferred backbones of the polyamines of the present invention can be prepared, for example, by polymerizing ethyleneimine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc.
  • a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc.
  • a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc.
  • Specific methods for preparing PEI's are disclosed in U.S. Patent 2,182,306, Ulrich et al., issued December 5, 1939; U.S. Patent 3,033,746, Mayle et al., issued May 8, 1962; U.S. Patent 2,208,095, Esselmann et al., issued July 16, 1940; U.S. Patent 2,806,839, Crowther, issued September
  • the present invention also includes the cyclic amines that are typically formed as artifacts of synthesis. The presence of these materials may be increased or decreased depending on the conditions chosen by the formulator. iv) Polv-Quaternarv Ammonium Compounds
  • R is substituted or unsubstituted C2-C12 alkyiene, substituted or unsubstituted C2-C12 hydroxyalkylene; each R is independently C1-C4 ⁇ lkyl, each R 2 is independently C i -C22 alkyl, C3-C22 alkenyl, R 5 -Q-(CH2) m -, wherein R 5 is CJ-C22 alkyl, C3-C22 alkenyl, and mixtures thereof; m is from 1 to about 6; Q is a carbonyl unit as defined hereinabove; and mixtures thereof; X is an anion.
  • R is ethylene; R is methyl or ethyl, more preferably methyl; at least one R2 is preferably C1-C4 alkyl, more preferably methyl. Preferably at least one R is C ⁇ 1-C22 alkyl, Cj 1-C22 alkenyl, and mixtures thereof.
  • the formulator may similarly choose R2 to be a R5-Q-(CH2) m - moiety wherein Rp is an alkyl moiety having from 1 to 22 carbon atoms, preferably the alkyl moiety when taken together with the Q unit is an acyl unit derived preferably derived from a source of triglyceride selected from the group consisting of tallow, partially hydrogenated tallow, lard, partially hydrogenated lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, com oil, soybean oil, tall oil, rice bran oil, etc. and mixtures thereof.
  • Rl is methyl, one R units is methyl and the other R2 unit is R ⁇ -Q- (CH2) m -wherein R- ⁇ -Q- is an oleoyl unit and m is equal to 2.
  • X is a softener compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and mixtures thereof, more preferably chloride and methyl sulfate.
  • a strong acid for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and mixtures thereof, more preferably chloride and methyl sulfate.
  • soil release agents will generally comprise from about 0.01% to about 10.0%, by weight, of the detergent compositions herein, typically from about 0.1% to about 5%, preferably from about 0.2% to about 3.0%.
  • soil release agents include the METOLOSE SMI 00, METOLOSE SM200 manufactured by Shin-etsu Kagaku Kogyo K.K., SOKALAN type of material, e.g., SOKALAN HP-22, available from BASF (Germany), ZELCON 5126 (from Dupont) and MILEASE T (from ICI).
  • Perfumes The products herein can also contain from about 0.5% to about 60%, preferably from about 1% to about 50%, cyclodextrin/perfume inclusion complexes and/or free perfume, as disclosed in U.S. Pat. Nos. 5,139,687, Borcher et al., issued Aug. 18, 1992; and 5,234,610, Gardlik et al., to issue Aug. 10, 1993, which are incorporated herein by reference.
  • Perfumes are highly desirable, can usually benefit from protection, and can be complexed with cyclodextrin.
  • Fabric softening products typically contain perfume to provide an olfactory aesthetic benefit and/or to serve as a signal that the product is effective.
  • perfume ingredients and compositions of this invention are the conventional ones known in the art. Selection of any perfume component, or amount of perfume, is based solely on aesthetic considerations. Suitable perfume compounds and compositions can be found in the art including U.S. Pat. Nos.: 4,145,184, Brain and Cummins, issued Mar. 20, 1979; 4,209,417, Whyte, issued June 24, 1980; 4,515,705, Moeddel, issued May 7, 1985; and 4,152,272, Young, issued May 1, 1979, all of said patents being incorporated herein by reference. Many of the art recognized perfume compositions are relatively substantive to maximize their odor effect on substrates. However, it is a special advantage of perfume delivery via the perfume/cyclodextrin complexes that nonsubstantive perfumes are also effective.
  • Stabilizers can be present in the compositions of the present invention.
  • the term "stabilizer,” as used herein, includes antioxidants and reductive agents. These agents are present at a level of from 0% to about 2%, preferably from about 0.01% to about 0.2%, more preferably from about 0.035% to about 0.1% for antioxidants, and more preferably from about 0.01% to about 0.2% for reductive agents. These assure good odor stability under long term storage conditions for the compositions and compounds stored in molten form.
  • the use of antioxidants and reductive agent stabilizers is especially critical for low scent products (low perfume).
  • antioxidants examples include a mixture of ascorbic acid, ascorbic palmitate, propyl gallate, available from Eastman Chemical Products, Inc., under the trade names Tenox® PG and Tenox S-l; a mixture of BHT (butylated hydroxytoluene), BHA (butylated hydroxyanisole), propyl gallate, and citric acid, available from Eastman Chemical Products, Inc., under the trade name Tenox-6; butylated hydroxytoluene, available from UOP Process Division under the trade name Sustane® BHT; tertiary butylhydroquinone, Eastman Chemical Products, Inc., as Tenox TBHQ; natural tocopherols, Eastman Chemical Products, Inc., as Tenox GT-l/GT-2; and butylated hydroxyanisole, Eastman Chemical Products, Inc., as BHA; long chain esters (Cs- C22) of gallic acid, e.g., dodecyl
  • Tiron® available from Kodak with a chemical name of 4,5-dihydroxy-m-benzene- sulfonic acid/sodium salt, EDDS, and DTP A®, available from Aldrich with a chemical name of diethylenetriaminepentaacetic acid. Concentration aids
  • Inorganic viscosity/dispersibility control agents which can also act like or augment the effect of the surfactant concentration aids, include water-soluble, ionizable salts which can also optionally be incorporated into the compositions of the present invention.
  • ionizable salts can be used. Examples of suitable salts are the halides of the Group IA and IIA metals of the Periodic Table of the Elements, e.g., calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride.
  • the ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein, and later to obtain the desired viscosity.
  • the amount of ionizable salts used depends on the amount of active ingredients used in the compositions and can be adjusted according to the desires of the formulator. Typical levels of salts used to control the composition viscosity are from about 20 to about 20,000 parts per million (ppm), preferably from about 20 to about 11,000 ppm, by weight of the composition.
  • the present invention can include other adjunct components (minor components) conventionally used in textile treatment compositions, for example, colorants, preservatives, optical brighteners, opacifiers, anti-shrinkage agents, anti- wrinkle agents, fabric crisping agents, spotting agents, germicides, fungicides, anti- corrosion agents, antifoam agents, and the like.
  • adjunct components for example, colorants, preservatives, optical brighteners, opacifiers, anti-shrinkage agents, anti- wrinkle agents, fabric crisping agents, spotting agents, germicides, fungicides, anti- corrosion agents, antifoam agents, and the like.
  • suitable ingredients useful in fabric softener containing compositions see WO 97/03169 included herein by reference.
  • the following compositions illustrate the present invention.
  • N,N-di(canoyloxyethyl)-N-2-hydroxyethyl-N-methyl ammonium methyl sulfate available from Witco.
  • Polyvinylamine having a MW 23,000 available from BASF.
  • Polyvinylamine having a MW 1,500 available from BASF.
  • Minors can include perfume, dye, acid, preservatives, etc.

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Abstract

The present invention relates to fabric softener compositions having enhanced softening benefits comprising a fabric softener active in combination with a cationic charge booster. The cationic charge boosters of the present invention are suitable for use with any fabric softener active, preferably with diester and diamide quaternary ammonium (DEQA) compounds.

Description

FABRIC SOFTENERS HAVING INCREASED PERFORMANCE
FIELD OF THE INVENTION
The present invention relates to fabric softener compositions wherein the performance of the fabric softener active is enhanced by the presence of a cationic charge booster. The present invention also relates to methods for providing enhanced fabric conditioning benefits to fabric by contacting said fabric with a composition comprising a quaternary ammonium fabric softener active and one or more cationic charge boosting compounds.
BACKGROUND OF THE INVENTION
Consumers have come to expect clean, freshened, static-free, cling-free fabric after the laundry cycle. Fabric softeners, whether added at the laundry rinse stage or at the automatic dryer stage, have become a means for providing fabric, especially clothing, with direct enhancement of these properties. One important class of fabric softener actives comprises Diester and Diamide Quaternary Ammonium (DEQA) compounds which typically can comprise mono-, di-, or tri- functional amines (e.g. diethanol amine) which are converted to the corresponding esters or amides then fully or partially quatemized. Manipulation of the acyl moiety combined with the mono-, di-, or tri- functional amines have led to DEQA's which are effective fabric softener active suitable for use in dryer added or rinse added fabric softener compositions. However, some cationic fabric softening actives perform in some ways less well than others.
Accordingly, there remains a need in the art for cationic fabric softener compositions which have an increased or "boosted" fabric softening capacity. In addition, fabric softener compositions which comprise fabric softener actives having suitable properties other than sufficient cationic charge density, need a means to boost the overall charge density thereby providing to the consumer a better fabric care benefit.
BACKGROUND ART
The following relate to fabric softening and fabric enhancement. U.S. Pat. No. 3,915,867, Kang et al, issued October 28, 1975; U.S. 3,904,533, Neiditch et al. issued September 9, 1975; U.S. 4,401,578, Verbruggen, issued August 30, 1983; U.S. 4,767,547, Straathof et al., issued Aug. 30, 1988; U.S. 4,808,321 , Walley, issued February 28, 1989; U.S. 5,066,414, Chang, issued November 19, 1991; Japanese Patent Application 63-194316, filed November 21, 1988; Japanese Laid Open Publication 1,249,129, filed October 4, 1989; Japanese Patent Application 4- 333,667, published November 20, 1992; EP 243,735; EP 336,267-A with a priority of April 2, 1988; European Patent Application 243,735, Nusslein et al., published November 4, 1987; European Patent Application 409,502, Tandela et al., published January 23, 1991; European Patent Application 240,727, Nusslein et al., priority date of March 12, 1986; and WO 89/11522-A (DE 3,818,061 -A; EP-346,634-A), with a priority of May 27, 1988.
SUMMARY OF THE INVENTION
It has now been surprisingly discovered that the addition of certain cationic charge enhancing agents will sufficiently increase the performance of cationic fabric softener actives having diminished or insufficient charge density, to a level which allows the low charge density active to be used in fabric softening formulations. In addition, it has been surprisingly found that when cationic charge boosters are used in conjunction with Diester or Diamide Quaternary Ammonium (DEQA) compounds, these preferred fabric softening actives are enhanced even further.
The cationic charge enhancing agents of the present invention have the effect of increasing the net cationic charge concentration independent of the intrinsic properties of the softener active. Therefore, the formulator may combine fabric softener actives having low cationic charge capacity, but which have other desirable properties inter alia good dispensability, low melting point, with cationic charge boosters thereby obtaining a composition which overcomes the lack of cationic charge density of the fabric softener active.
The first aspect of the present invention relates to fabric softener compositions comprising: a) at least about 2%, preferably from about 2%, more preferably from about 5% to about 60%, more preferably to about 40% by weight, of a fabric softening active having the formula:
Figure imgf000004_0001
wherein each R is independently C \ -Cg alkyi. C \ -C hydroxyalkyl, benzyl, and mixtures thereof; R1 is C1-C22 alkyl, C3-C22 alkenyl, and mixtures thereof; Q is a carbonyl moiety having the formula:
O O R2 O O R2
II II I II II I
— O— C — , — C-O — , — N— C — , — C-N— ,
O
O R3 O O— C— Rl O
II I II I II
— O— C— O — , — CH—O— C — , — CH— CH2— O— C — wherein R2 is hydrogen, C1-C4 alkyl, C 1-C4 hydroxyalkyl, and mixtures thereof; R^ is hydrogen, C 1-C4 alkyl, and mixtures thereof;
X is a softener compatible anion; m is from 1 to 3; n is from 1 to 4; at least one cationic charge booster selected from the group consisting of: i) at least about 0.2%, preferably from about 0.2% to about 10%, more preferably from about 0.2% to about 6% by weight, of a cationic charge booster having the formula:
Figure imgf000005_0001
wherein R1 , R-, R3. and R4 are each independently C 1 -C22 alkyl, C3-C22 alkenyl. R5-Q-(CH )m-, wherein R5 is Cj - C22 alkyl, C3-C22 alkenyl, and mixtures thereof, m is from 1 to about 6; Q is a carbonyl unit as defined hereinabove; X is a softener compatible anion; ii) at least about 0.2%, preferably from about 0.2% to about 5%, more preferably from about 0.2% to about 2% by weight, of a cationic charge booster having the formula:
Figure imgf000005_0002
wherein each -NH2 unit hydrogen is optionally substituted by an alkyleneoxy unit having the formula: (RlO)xR2 wherein R-* is C2-C4 alkyiene, R2 is hydrogen, C1-C4 alkyl, and mixtures thereof; x is from 1 to 50; y is from 3 to about 10,000; iii) at least about 0.2%, preferably from about 0.2% to about 10%, more preferably from about 0.2% to about 5% by weight, of a cationic charge booster having the formula:
I
[H2N-R 1 -[N-R]m-[N-R]n-NH2 wherein R is C2-C6 alkyiene, m is from about 3 to about 70, n is from 0 to about 35; wherein each hydrogen atom of said backbone is optionally substituted by an alkyleneoxy unit having the formula:
(RlO)xR2 wherein R' is C2-C4 alkyiene, R is hydrogen, C 1 -C4 alkyl, and mixtures thereof; x is from 1 to 50; iv) at least about 0.2%, preferably from about 0.2% to about 10%, more preferably from about 0.2% to about 6% by weight, of a cationic charge booster having the formula:
Figure imgf000006_0001
wherein R is substituted or unsubstituted C2-C12 alkyiene, substituted or unsubstituted C2-C12 hydroxyalkylene; each Rl is independently C j -C4 alkyl, each R2 is independently C1-C22 alkyl, C3-C22 alkenyl, R5-Q-(CH2)m-, wherein R5 is C1-C22 alkyl, C3-C22 alkenyl, and mixtures thereof; m is from 1 to about 6; Q is a carbonyl unit as defined hereinabove; and mixtures thereof; X is a softener compatible anion; and v) mixtures thereof; and c) the balance carriers and adjunct ingredients, said adjunct ingredients selected from the group consisting of nonionic fabric softening agents, concentration aid, soil release agent, perfume, preservatives, stabilizers, colorants, optical brighteners, opacifiers, fabric conditioning agents, anti-shrinkage agents, anti-wrinkle agents, fabric crisping agents, spotting agents, germicides, fungicides, anti- corrosion agents, antifoam agents, and mixtures thereof. The present invention further relates to methods for boosting the cationic charge of fabric softening compositions by adding one or more charge boosting components. These and other objects, features and advantages will become apparent to those of ordinary skill in the art from a reading of the following detailed description and the appended claims.
All percentages, ratios and proportions herein are by weight, unless otherwise specified. All temperatures are in degrees Celsius (° C) unless otherwise specified. All documents cited are in relevant part, incorporated herein by reference. DETAILED DESCRIPTION OF THE INVENTION The present invention relates to improving the softening capacity of fabric softener actives, preferably Diester and Diamide Quaternary Ammonium (DEQA) fabric softening actives. Without wishing to be limited by theory it has been surprisingly discovered that the performance of fabric softener actives can be further enhanced by combining said actives with certain cationic charge boosters. The effect is to increase the overall charge density of the total softener composition. Among the compounds suitable for use as cationic charge boosters are compounds having pre-formed cations (i.e. quaternary ammonium compounds) while others (i.e. ethoxylated polyethyleneimines) form the cationic charge booster in situ during storage or during use.
Quaternary Ammonium Fabric Softening Active Compounds (DEQA) The preferred fabric softening actives according to the present invention have the formula:
Figure imgf000007_0001
wherein each R is independently Cj-Cό alkyl, C\-C hydroxyalkyl, benzyl, and mixtures thereof; Rl is preferably C\ 1-C22 alkyl, C\ 1-C22 alkenyl, and mixtures thereof; Q is a carbonyl moiety having the formula:
O O R2 O O R2
II II I II II I
— O— C — , — C— O — , — N— C- -C-N-
Figure imgf000008_0001
wherein R2 is hydrogen, C1-C4 alkyl, preferably hydrogen; R^ is C1-C4 alkyl, preferably hydrogen or methyl; preferably Q has the formula:
O O
II II
— O— C — or — NH-C —
X is a softener compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and mixtures thereof, more preferably chloride and methyl sulfate. The anion can also, but less preferably, carry a double charge, in which case χ(') represents half a group. The index m has a value of from 1 to 3; the index n has a value of from 1 to 4, preferably 2 or 3, more preferably 2.
More preferred softener actives according to the present invention have the formula:
Figure imgf000008_0002
wherein the unit having the formula:
O — O— C-Rl is a fatty acyl moiety. Suitable fatty acyl moieties for use in the softener actives of the present invention are derived from sources of triglycerides including tallow, vegetable oils and/or partially hydrogenated vegetable oils including inter alia canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil.
The Rl units are typically mixtures of linear and branched chains of both saturated and unsaturated aliphatic fatty acids, an example of which (canola oil), is described in Table I herein below.
Table I
Fatty acyl unit %
C14 0.1
C16 5.4
C16:l 0.4
C18 5.7
C18:l 67.0
C18:2 13.5
C18:3 2.7
C20 0.5
C20:l 4.6
The formulator, depending upon the desired physical and performance properties of the final fabric softener active, can choose any of the above mentioned sources of fatty acyl moieties, or alternatively, the formulator can mix sources of triglyceride to form a "customized blend". However, those skilled in the art of fats and oils recognize that the fatty acyl composition may vary, as in the case of vegetable oil, from crop to crop, or from variety of vegetable oil source to variety of vegetable oil source. DEQA's which are prepared using fatty acids derived from natural sources are preferred.
A preferred embodiment of the present invention provides softener actives comprising Rl units which have at least about 3%, preferably at least about 5%, more preferably at least about 10%, most preferably at least about 15% Cj 1-C22 alkenyl, including polyalkenyl (polyunsaturated) units inter alia oleic, linoleic, linolenic.
For the purposes of the present invention the term "mixed chain fatty acyl units" is defined as "a mixture of fatty acyl units comprising alkyl and alkenyl chains having from 10 carbons to 22 carbon atoms including the carbonyl carbon atom, and in the case of alkenyl chains, from one to three double bonds, preferably all double bonds in the cis configuration". With regard to the R units of the present invention, it is preferred that at least a substantial percentage of the fatty acyl groups are unsaturated, e.g., from about 25%, preferably from about 50% to about 70%, preferably to about 65%. The total level of fabric softening active containing polyunsaturated fatty acyl groups can be from about 3%, preferably from about 5%, more preferably from about 10% to about 30%, preferably to about 25%, more preferably to about 18%. As stated herein above cis and trans isomers can be used, preferably with a cis/ trans ratio is of from 1 : 1, preferably at least 3:1, and more preferably from about 4:1 to about 50:1, more preferably about 20:1, however, the minimum being 1 :1.
The R units suitable for use in the present invention can be further characterized by the Iodine Value (IV) of the parent fatty acid, said IV is preferably from about 20, more preferably from about 50, most preferably from about 70, to a value of about 140, preferably to about 130, more preferably to about 115. However, formulators, depending upon which embodiment of the present invention they choose to execute, may wish to add an amount of fatty acyl units which have Iodine Values outside the range listed herein above. For example, "hardened stock" (IV less than or equal to about 10) may be combined with the source of fatty acid admixture to adjust the properties of the final softener active. A further preferred embodiment of the present invention comprises DEQA's wherein the average Iodine Value for Rl is approximately 45.
Amines which are used to prepare the preferred fabric softening actives of the present invention have the formula:
Figure imgf000010_0001
wherein R is the same as defined herein above; each Z is independently selected from the group consisting of -OH, -CHR OH, -CH(OH)CH2OH, -NH2, and mixtures thereof; preferably -OH, -NH2, and mixtures thereof; R3 is CJ-C4 alkyl, preferably methyl; the indices m and n are the same as defined hereinabove.
Non-limiting examples of preferred amines which are used to form the DEQA fabric softening actives according to the present invention include methyl bis(2-hydroxyethyl)amine having the formula:
Figure imgf000010_0002
methyl bis(2-hydroxypropyl)amine having the formula:
Figure imgf000011_0001
methyl (3-aminopropyl) (2-hydroxyethyl)amine having the formula:
Figure imgf000011_0002
methyl bis(2-aminoethyl)amine having the formula:
Figure imgf000011_0003
triethanol amine having the formula:
Figure imgf000011_0004
bis(2-aminoethyl) ethanolamine having the formula:
Figure imgf000011_0005
For the purposes of the present invention, R moieties which are introduced during the quaternization step are preferably methyl. In the case of amines having the formula:
Figure imgf000011_0006
R is preferably the same moiety (i.e. methyl) which is introduced during the quaternization step. For example, a methyl amine having the formula:
CH3—N- "(CH2)n-Z is preferably quatemized to the softener active having the general formula:
Figure imgf000012_0001
In one embodiment of the present invention, the fabric softening active precursor amine mixture is not fully quatemized, that is, some free amine having the general formula:
Figure imgf000012_0002
is still present in the final fabric softener mixture.
A yet further embodiment of the present invention comprises an amine of the formula:
Gte '3-m-N-KCHzfo-Z m wherein not all of the Z units are fully reacted with a fatty acyl moiety thereby leaving an amount of amiήe and/or quatemized ammonium compound in the final fabric softener active admixture having one or more Z units unreacted and thereby not transformed into an ester or amide..
The following are examples of preferred softener actives according to the present invention.
N,N-di(tallowyl-oxy-ethyl)-N,N-dimethyl ammonium chloride;
N,N-di(canolyl-oxy-ethyl)-N,N-dimethyl ammonium chloride;
N,N-di(tallowyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium chloride;
N,N-di(canolyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium chloride;
N,N-di(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride;
N,N-di(2-canolyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride
N,N-di(2-tallowyloxyethylcarbonyloxyethyl)-N,N-dimethyl ammonium chloride; N,N-di(2-canolyloxyethylcarbonyloxyethyl)-N,N-dimethyl ammonium chloride; N-(2-tallowoyloxy-2-ethyl)-N-(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride; N-(2-canolyloxy-2-ethyl)-N-(2-canoIyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride; N,N,N-tri(tallowyl-oxy-ethyl)-N-methyl ammonium chloride; N,N,N-tricanolyl-oxy-ethyl)-N-methyl ammonium chloride; N-(2-tallowyloxy-2-oxoethyl)-N-(tallowyl)-N,N-dimethyl ammonium chloride; N-(2-canolyloxy-2-oxoethyl)-N-(canolyl)-N,N-dimethyl ammonium chloride; l,2-ditallowyloxy-3-N,N,N-trimethylammoniopropane chloride; and 1 ,2-dicanolyloxy-3-N,N,N-trimethylammoniopropane chloride; and mixtures of the above actives. Particularly preferred is N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride, where the tallow chains are at least partially unsaturated and N,N-di(canoloyl-oxy-ethyl)-N,N-dimethyl ammonium chloride.
The amount of fabric softening active present in the compositions of the present invention is at least about 2%, preferably from about 2%, more preferably from about 5% to about 60%, more preferably to about 40% by weight, of the composition.
Cationic Charge Boosters The preferred cationic charge boosters of the present invention are described herein below. i) Quaternary Ammonium Compounds
A preferred composition of the present invention comprises at least about 0.2%, preferably from about 0.2% to about 10%, more preferably from about 0.2% to about 5% by weight, of a cationic charge booster having the formula:
Figure imgf000013_0001
wherein Rl, R2, R3, and R^ are each independently C1-C22 alkyl, C3-C22 alkenyl, R5-Q-(CH2)m-, wherein R-^ is C1-C22 alkyl, and mixtures thereof, m is from 1 to about 6; X is an anion. Preferably R is C6-C22 alkyl, Cg-C22 alkenyl, and mixtures thereof, more preferably C\ J -CJ S lkyl> j-Cjg alkenyl, and mixtures thereof; R2, R3, and R4 are each preferably C1-C4 alkyl, more preferably each R2, R3? and R4 are methyl.
The formulator may similarly choose R to be a R5-Q-(CH2)m- moiety wherein R$ is an alkyl or alkenyl moiety having from 1 to 22 carbon atoms, preferably the alkyl or alkenyl moiety when taken together with the Q unit is an acyl unit derived preferably derived from a source of triglyceride selected from the group consisting of tallow, partially hydrogenated tallow, lard, partially hydrogenated lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, co oil, soybean oil, tall oil, rice bran oil, etc. and mixtures thereof.
An example of a fabric softener cationic booster comprising a R-^-Q- (CH2)m- moiety has the formula:
Figure imgf000014_0001
wherein R-^-Q- is an oleoyl units and m is equal to 2.
X is a softener compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and mixtures thereof, more preferably chloride and methyl sulfate. ii) Polyvinyl Amines
A preferred composition according to the present invention contains at least about 0.2%, preferably from about 0.2% to about 5%, more preferably from about 0.2% to about 2% by weight, of one or more poly vinyl amines having the formula
Figure imgf000014_0002
wherein y is from about 3 to about 10,000, preferably from about 10 to about 5,000, more preferably from about 20 to about 500. Polyvinyl amines suitable for use in the present invention are available from BASF.
Optionally, one or more of the polyvinyl amine backbone -NH2 unit hydrogens can be substituted by an alkyleneoxy unit having the formula:
-(Rl0)χR2 wherein Rl is C2-C4 alkyiene, R is hydrogen, C1-C4 alkyl, and mixtures thereof; x is from 1 to 50. In one embodiment or the present invention the polyvinyl amine is reacted first with a substrate which places a 2-propyleneoxy unit directly on the nitrogen followed by reaction of one or more moles of ethylene oxide to form a unit having the general formula:
Figure imgf000015_0001
wherein x has the value of from 1 to about 50. Substitutions such as the above are represented by the abbreviated formula PO-EOx-. However, more than one propyleneoxy unit can be incorporated into the alkyleneoxy substituent.
Polyvinyl amines are especially preferred for use as cationic charge booster in liquid fabric softening compositions since the greater number of amine moieties per unit weight provides substantial charge density. In addition, the cationic charge is generated in situ and the level of cationic charge can be adjusted by the formulator. iii) Polvalkyleneimines
A preferred composition of the present invention comprises at least about 0.2%, preferably from about 0.2% to about 10%, more preferably from about 0.2% to about 5% by weight, of a polyalkyleneimine charge booster having the formula:
[H^-RJrr l -[N ¥-R]m-[N 1 -R]n-NH2 wherein the value of m is from 2 to about 700 and the value of n is from 0 to about 350. Preferably the compounds of the present invention comprise polyamines having a ratio of m : n that is at least 1:1 but may include linear polymers (n equal to 0) as well as a range as high as 10:1, preferably the ratio is 2:1. When the ratio of m:n is 2:1, the ratio of primary secondary :tertary amine moieties, that is the ratio of -RNH2, -RNH, and -RN moieties, is 1 :2:1.
R units are C2~C alkyiene, C -Cg alkyl substituted alkyiene, and mixtures thereof, preferably ethylene, 1 ,2-propylene, 1 ,3-propylene, and mixtures thereof, more preferably ethylene. R units serve to connect the amine nitrogens of the backbone.
Optionally, one or more of the polyvinyl amine backbone -NH2 unit hydrogens can be substituted by an alkyleneoxy unit having the formula: — (RlO)xR2 wherein Rl is C2-C4 alkyiene, R is hydrogen, C1-C4 alkyl, and mixtures thereof; x is from 1 to 50. In one embodiment or the present invention the polyvinyl amine is reacted first with a substrate which places a 2-propyleneoxy unit directly on the nitrogen followed by reaction of one or more moles of ethylene oxide to form a unit having the general formula:
CH3 I (CH2CHO) — (CH2CH2O)χH wherein x has the value of from 1 to about 50. Substitutions such as the above are represented by the abbreviated formula PO-EOx-. However, more than one propyleneoxy unit can be incorporated into the alkyleneoxy substituent.
The preferred polyamine cationic charge boosters of the present invention comprise backbones wherein less than 50% of the R groups comprise more than 3 carbon atoms. The use of two and three carbon spacers as R moieties between nitrogen atoms in the backbone is advantageous for controlling the charge booster properties of the molecules. More preferred embodiments of the present invention comprise less than 25% moieties having more than 3 carbon atoms. Yet more preferred backbones comprise less than 10% moieties having more than 3 carbon atoms. Most preferred backbones comprise 100% ethylene moieties.
The cationic charge boosting polyamines of the present invention comprise homogeneous or non-homogeneous polyamine backbones, preferably homogeneous backbones. For the purpose of the present invention the term "homogeneous polyamine backbone" is defined as a polyamine backbone having R units that are the same (i.e., all ethylene). However, this sameness definition does not exclude polyamines that comprise other extraneous units comprising the polymer backbone that are present due to an artifact of the chosen method of chemical synthesis. For example, it is known to those skilled in the art that ethanolamine may be used as an "initiator" in the synthesis of polyethyleneimines, therefore a sample of polyethyleneimine that comprises one hydroxyethyl moiety resulting from the polymerization "initiator" would be considered to comprise a homogeneous polyamine backbone for the purposes of the present invention.
For the purposes of the present invention the term "non-homogeneous polymer backbone" refers to polyamine backbones that are a composite of one or more alkyiene or substituted alkyiene moieties, for example, ethylene and 1,2- propylene units taken together as R units However, not all of the suitable charge booster agents belonging to this category of polyamine comprise the above described polyamines. Other polyamines that comprise the backbone of the compounds of the present invention are generally polyalkyleneamines (PAA's), polyalkyleneimines (PAI's), preferably polyethyleneamine (PEA's), or polyethyleneimines (PEI's). A common polyalkyleneamine (PAA) is tetrabutylenepentamine. PEA's are obtained by reactions involving ammonia and ethylene dichloride, followed by fractional distillation. The common PEA's obtained are triethylenetetramine (TETA) and tetraethylenepentamine (TEPA). Above the pentamines, i.e., the hexamines, heptamines, octamines and possibly nonamines, the cogenerically derived mixture does not appear to separate by distillation and can include other materials such as cyclic amines and particularly piperazines. There can also be present cyclic amines with side chains in which nitrogen atoms appear. See U.S. Patent 2,792,372, Dickinson, issued May 14, 1957, which describes the preparation of PEA's.
The PEI's which comprise the preferred backbones of the polyamines of the present invention can be prepared, for example, by polymerizing ethyleneimine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc. Specific methods for preparing PEI's are disclosed in U.S. Patent 2,182,306, Ulrich et al., issued December 5, 1939; U.S. Patent 3,033,746, Mayle et al., issued May 8, 1962; U.S. Patent 2,208,095, Esselmann et al., issued July 16, 1940; U.S. Patent 2,806,839, Crowther, issued September 17, 1957; and U.S. Patent 2,553,696, Wilson, issued May 21, 1951 (all herein incorporated by reference). In addition to the linear and branched PEI's, the present invention also includes the cyclic amines that are typically formed as artifacts of synthesis. The presence of these materials may be increased or decreased depending on the conditions chosen by the formulator. iv) Polv-Quaternarv Ammonium Compounds
A preferred composition of the present invention comprises at least about 0.2%, preferably from about 0.2% to about 10%, more preferably from about 0.2% to about 5% by weight, of a cationic charge booster having the formula:
Figure imgf000017_0001
wherein R is substituted or unsubstituted C2-C12 alkyiene, substituted or unsubstituted C2-C12 hydroxyalkylene; each R is independently C1-C4 ^lkyl, each R2 is independently C i -C22 alkyl, C3-C22 alkenyl, R5-Q-(CH2)m-, wherein R5 is CJ-C22 alkyl, C3-C22 alkenyl, and mixtures thereof; m is from 1 to about 6; Q is a carbonyl unit as defined hereinabove; and mixtures thereof; X is an anion.
Preferably R is ethylene; R is methyl or ethyl, more preferably methyl; at least one R2 is preferably C1-C4 alkyl, more preferably methyl. Preferably at least one R is C\ 1-C22 alkyl, Cj 1-C22 alkenyl, and mixtures thereof.
The formulator may similarly choose R2 to be a R5-Q-(CH2)m- moiety wherein Rp is an alkyl moiety having from 1 to 22 carbon atoms, preferably the alkyl moiety when taken together with the Q unit is an acyl unit derived preferably derived from a source of triglyceride selected from the group consisting of tallow, partially hydrogenated tallow, lard, partially hydrogenated lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, com oil, soybean oil, tall oil, rice bran oil, etc. and mixtures thereof.
An example of a fabric softener cationic booster comprising a R-5-Q- (CH2) - moiety has the formula:
Figure imgf000018_0001
wherein Rl is methyl, one R units is methyl and the other R2 unit is R^-Q- (CH2)m-wherein R-^-Q- is an oleoyl unit and m is equal to 2.
X is a softener compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and mixtures thereof, more preferably chloride and methyl sulfate.
ADJUNCT INGREDIENTS
The following are non-limiting examples of adjunct ingredients which are suitable for use in the fabric softening compositions of the present invention. Soil Release Agents
Any polymeric soil release agent known to those skilled in the art can optionally be employed in the compositions and processes of this invention. Polymeric soil release agents are characterized by having both hydrophilic segments, to hydrophilize the surface of hydrophobic fibers, such as polyester and nylon, and hydrophobic segments, to deposit upon hydrophobic fibers and remain adhered thereto through completion of washing and rinsing cycles and, thus, serve as an anchor for the hydrophilic segments. This can enable stains occurring subsequent to treatment with the soil release agent to be more easily cleaned in later washing procedures.
If utilized, soil release agents will generally comprise from about 0.01% to about 10.0%, by weight, of the detergent compositions herein, typically from about 0.1% to about 5%, preferably from about 0.2% to about 3.0%.
The following, all included herein by reference, describe soil release polymers suitable for use in the present invention. U.S. 3,959,230 Hays, issued May 25, 1976; U.S. 3,893,929 Basadur, issued July 8, 1975; U.S. 4,000,093, Nicol, et al, issued December 28, 1976; U.S. Patent 4,702,857 Gosselink, issued October 27, 1987; U.S. 4,968,451, Scheibel et al, issued November 6; U.S. 4,702,857, Gosselink, issued October 27, 1987; U.S. 4,711,730, Gosselink et al, issued December 8, 1987; U.S. 4,721,580, Gosselink, issued January 26, 1988; U.S. 4,877,896, Maldonado et al, issued October 31, 1989; U.S. 4,956,447, Gosselink et al, issued September 11, 1990; U.S. 5,415,807 Gosselink et al, issued May 16, 1995; European Patent Application 0 219 048, published April 22, 1987 by Kud, et al.
Further suitable soil release agents are described in U.S. 4,201,824, Violland et al; U.S. 4,240,918 Lagasse et al; U.S. 4,525,524 Tung et al; U.S. 4,579,681, Ruppert et al; U.S. 4,240,918; U.S. 4,787,989; U.S. 4,525,524; EP 279,134 A, 1988, to Rhone-Poulenc Chemie; EP 457,205 A to BASF (1991); and DE 2.335,044 to Unilever N. V., 1974 all incorporated herein by reference.
Commercially available soil release agents include the METOLOSE SMI 00, METOLOSE SM200 manufactured by Shin-etsu Kagaku Kogyo K.K., SOKALAN type of material, e.g., SOKALAN HP-22, available from BASF (Germany), ZELCON 5126 (from Dupont) and MILEASE T (from ICI).
Perfumes The products herein can also contain from about 0.5% to about 60%, preferably from about 1% to about 50%, cyclodextrin/perfume inclusion complexes and/or free perfume, as disclosed in U.S. Pat. Nos. 5,139,687, Borcher et al., issued Aug. 18, 1992; and 5,234,610, Gardlik et al., to issue Aug. 10, 1993, which are incorporated herein by reference. Perfumes are highly desirable, can usually benefit from protection, and can be complexed with cyclodextrin. Fabric softening products typically contain perfume to provide an olfactory aesthetic benefit and/or to serve as a signal that the product is effective.
The optional perfume ingredients and compositions of this invention are the conventional ones known in the art. Selection of any perfume component, or amount of perfume, is based solely on aesthetic considerations. Suitable perfume compounds and compositions can be found in the art including U.S. Pat. Nos.: 4,145,184, Brain and Cummins, issued Mar. 20, 1979; 4,209,417, Whyte, issued June 24, 1980; 4,515,705, Moeddel, issued May 7, 1985; and 4,152,272, Young, issued May 1, 1979, all of said patents being incorporated herein by reference. Many of the art recognized perfume compositions are relatively substantive to maximize their odor effect on substrates. However, it is a special advantage of perfume delivery via the perfume/cyclodextrin complexes that nonsubstantive perfumes are also effective.
If a product contains both free and complexed perfume, the escaped perfume from the complex contributes to the overall perfume odor intensity, giving rise to a longer lasting perfume odor impression.
As disclosed in U.S. Pat. No. 5,234,610, Gardlik Trinh/Banks Benvegnu, issued Aug. 3, 1993, said patent being incorporated herein by reference, by adjusting the levels of free perfume and perfume/CD complex it is possible to provide a wide range of unique perfume profiles in terms of timing (release) and/or perfume identity (character). Solid, dryer-activated fabric conditioning compositions are a uniquely desirable way to apply the cyclodextrins, since they are applied at the very end of a fabric treatment regimen when the fabric is clean and when there are almost no additional treatments that can remove the cyclodextrin.
Stabilizers
Stabilizers can be present in the compositions of the present invention. The term "stabilizer," as used herein, includes antioxidants and reductive agents. These agents are present at a level of from 0% to about 2%, preferably from about 0.01% to about 0.2%, more preferably from about 0.035% to about 0.1% for antioxidants, and more preferably from about 0.01% to about 0.2% for reductive agents. These assure good odor stability under long term storage conditions for the compositions and compounds stored in molten form. The use of antioxidants and reductive agent stabilizers is especially critical for low scent products (low perfume).
Examples of antioxidants that can be added to the compositions of this invention include a mixture of ascorbic acid, ascorbic palmitate, propyl gallate, available from Eastman Chemical Products, Inc., under the trade names Tenox® PG and Tenox S-l; a mixture of BHT (butylated hydroxytoluene), BHA (butylated hydroxyanisole), propyl gallate, and citric acid, available from Eastman Chemical Products, Inc., under the trade name Tenox-6; butylated hydroxytoluene, available from UOP Process Division under the trade name Sustane® BHT; tertiary butylhydroquinone, Eastman Chemical Products, Inc., as Tenox TBHQ; natural tocopherols, Eastman Chemical Products, Inc., as Tenox GT-l/GT-2; and butylated hydroxyanisole, Eastman Chemical Products, Inc., as BHA; long chain esters (Cs- C22) of gallic acid, e.g., dodecyl gallate; Irganox® 1010; Irganox® 1035; Irganox®
B 1 171 ; Irganox® 1425; Irganox® 31 14; Irganox® 3125; and mixtures thereof; preferably Irganox® 3125, Irganox® 1425, Irganox® 31 14, and mixtures thereof; more preferably Irganox® 3125 alone or mixed with citric acid and/or other chelators such as isopropyl citrate, Dequest® 2010, available from Monsanto with a chemical name of 1-hydroxyethylidene-l, 1-diphosphonic acid (etidronic acid), and
Tiron®, available from Kodak with a chemical name of 4,5-dihydroxy-m-benzene- sulfonic acid/sodium salt, EDDS, and DTP A®, available from Aldrich with a chemical name of diethylenetriaminepentaacetic acid. Concentration aids
Concentrated compositions of the present invention may require organic and/or inorganic concentration aids to go to even higher concentrations and/or to meet higher stability standards depending on the other ingredients. Surfactant concentration aids are typically selected from the group consisting of single long chain alkyl cationic surfactants; nonionic surfactants; amine oxides; fatty acids; or mixtures thereof, typically used at a level of from 0 to about 15% of the composition.
Inorganic viscosity/dispersibility control agents which can also act like or augment the effect of the surfactant concentration aids, include water-soluble, ionizable salts which can also optionally be incorporated into the compositions of the present invention. A wide variety of ionizable salts can be used. Examples of suitable salts are the halides of the Group IA and IIA metals of the Periodic Table of the Elements, e.g., calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride. The ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein, and later to obtain the desired viscosity. The amount of ionizable salts used depends on the amount of active ingredients used in the compositions and can be adjusted according to the desires of the formulator. Typical levels of salts used to control the composition viscosity are from about 20 to about 20,000 parts per million (ppm), preferably from about 20 to about 11,000 ppm, by weight of the composition.
Other Adjunct Ingredients
The present invention can include other adjunct components (minor components) conventionally used in textile treatment compositions, for example, colorants, preservatives, optical brighteners, opacifiers, anti-shrinkage agents, anti- wrinkle agents, fabric crisping agents, spotting agents, germicides, fungicides, anti- corrosion agents, antifoam agents, and the like. For examples of other suitable ingredients useful in fabric softener containing compositions see WO 97/03169 included herein by reference. The following compositions illustrate the present invention.
Weight %
Ingredients 1 2 3 5
DEQA 1 26.0 25.7 26.0 30.0
MAQ 2 -- — — —
PVAm-23K 3 2.0 ~ -- —
PVAm-1.2K 4 -- 1.0 — —
Polyethylenediamine 5 -- — 2.0 --
MADQ 6 — ~ « 2.4
Ethanol 2.2 2.4 2.2 2.6
Hexylene glycol 2.6 2.3 2.6 2.6
1 ,2-Hexanediol 17.0 ~ 17.0 --
TMPD 7 -- 11.9 — 12.0
CHDM 8 -- 5.0 -- 48.1
Water 52.5 53.6 52.5 48.1
Minors 8 balance balance balance balance
1. N,N-di(canoyloxyethyl)-N-2-hydroxyethyl-N-methyl ammonium methyl sulfate available from Witco.
2. Monocanolyl trimethyl ammonium chloride, available as Adogen 417® from Witco.
3. Polyvinylamine having a MW = 23,000 available from BASF.
4. Polyvinylamine having a MW = 1,500 available from BASF.
5. Ethoxylated polyethyleneimine having a backbone average molecular weight of 1800 and an average of 1 ethyleneoxy unit substituted per N-H backbone unit (PEI 1800 El), added as a 10% aqueous solution acidified to pH 3 with cone. HC1.
6. Monotallowyl diquat., available as Adogen 277® from Witco.
7. Trimethyl pnetanediol available from Eastman Chemical.
8. 1 ,4-cyclohexane dimethanol available from Eastman Chemical.
9. Minors can include perfume, dye, acid, preservatives, etc.

Claims

What is claimed is:
1. A fabric softener composition comprising: a) at least 2%, preferably from 2%, more preferably from 5% to 60%, more preferably to 40% by weight, of a fabric softening active having the formula:
X
Figure imgf000023_0001
wherein each R is independently C\-C alkyl, C\-C hydroxyalkyl, benzyl, and mixtures thereof; Rl is C\-C22 alkyl, C3-C22 alkenyl, and mixtures thereof; Q is a carbonyl moiety having the formula:
-
Figure imgf000023_0002
wherein R is hydrogen, C1-C4 alkyl, C1-C4 hydroxyalkyl, and mixtures thereof; R3 is hydrogen, C j -C4 alkyl, and mixtures thereof;
X is a softener compatible anion; m is from 1 to 3; n is from 1 to 4; b) at least one cationic charge booster selected from the group consisting of: i) at least 0.2%, preferably from 0.2% to 10%, more preferably from 0.2% to 6% by weight, of a cationic charge booster having the formula:
Figure imgf000023_0003
wherein R**, R , R3, and R4 are each independently C1-C22 alkyl, C3-C22 alkenyl, R5-Q-(CH2)m-, wherein R5 is C\- C22 alkyl, C3-C22 alkenyl, and mixtures thereof, m is from 1 to 6; Q is a carbonyl unit as defined hereinabove: X is a softener compatible anion; ii) at least 0.2%, preferably from 0.2% to 5%, more preferably from 0.2% to 2% by weight, of a cationic charge booster having the formula:
Figure imgf000024_0001
wherein each -NH2 unit hydrogen is optionally substituted by an alkyleneoxy unit having the formula:
(Rl0)χR2 wherein Rl is C2-C4 alkyiene, R is hydrogen, C 1 -C4 alkyl, and mixtures thereof; x is from 1 to 50; y is from 3 to 10,000; iii) at least 0.2%, preferably from 0.2% to 10%, more preferably from 0.2% to 5% by weight, of a cationic charge booster having the formula:
H I
[H∑N-Rfen -[N-R]m-[N-R]n-NH2 wherein R is C2-C6 alkyiene, m is from 3 to 70, n is from 0 to 35; wherein each hydrogen atom of said backbone is optionally substituted by an alkyleneoxy unit having the formula:
Figure imgf000024_0002
wherein R-- is C2-C4 -alkyiene, R2 is hydrogen, C 1 -C4 alkyl, and mixtures thereof; x is from 1 to 50; iv) at least 0.2%, preferably from 0.2% to 10%, more preferably from 0.2% to 5% by weight, of a cationic charge booster having the formula:
Figure imgf000025_0001
wherein R is substituted or unsubstituted C2-C12 alkyiene, substituted or unsubstituted C2-C12 hydroxyalkylene; each Rl is independently C1-C4 alkyl, each R is independently C!-C22 alkyl, C3-C22 alkenyl, R5-Q-(CH2)m-, wherein R-5 is C1-C22 alkyl, C3-C22 alkenyl, and mixtures thereof; m is from 1 to 6; Q is a carbonyl unit as defined hereinabove; and mixtures thereof; X is a softener compatible anion; and v) mixtures thereof; and c) the balance carriers and adjunct ingredients.
A composition according to Claim 1 wherein Q has the formula:
O O
II II -O— C — or -C— O —
3. A composition according to either Claim 1 or 2 wherein R is methyl, hydroxyethyl, and mixtures thereof.
4. A composition according to any of Claims 1-3 wherein n is equal to 2.
5. A composition according to any of Claims 1-4 wherein said cationic charge booster has the formula:
Figure imgf000025_0002
wherein y is from 3 to 10,000.
6. A composition according to any of Claims 1-5 wherein y is from 10 to 1,000.
7. A composition according to any of Claims 1-6 wherein Rl is derived from tallow, canola oil, and mixtures thereof. A composition according to any of Claims 1-7 wherein each R is independently methyl, hydroxyethyl, and mixtures thereof; and Q has the formula:
O
II
— O- -c-
9. A composition according to any of Claims 1-8 wherein X is -O3SOCH3.
10. A fabric softener composition comprising: a) at least 2%, preferably from 2%, more preferably from 5% to 60%, more preferably to 40% by weight, of a quaternary ammonium fabric softening compound having the formula:
Figure imgf000026_0001
wherein Q is a carbonyl unit having the formula:
O II — O— C — .
R is methyl; each Rl unit is independently linear or branched C\ \-
C22 alkyl, linear or branched Cj 1-C22 alkenyl, and mixtures thereof;
X is chloro, -O3SOCH3, and mixtures thereof; b) at least one cationic charge booster selected form the group consisting of: i) at least 0.2%, preferably from 0.2% to 10%, more preferably from 0.2% to 5% by weight, of a cationic charge booster having the formula:
Figure imgf000026_0002
wherein Rl, R , R3, and R4 are each independently -C22 alkyl, C3-C22 alkenyl, R5-Q-(CH2)m-, wherein R5 is C\- C22 alkyl, and mixtures thereof, m is from 1 to 6; Q is a carbonyl unit as defined hereinabove; X is an anion; ii) at least 0.2%, preferably from 0.2% to 5%. more preferably from 0.2% to 2% by weight, of a cationic charge booster having the formula:
Figure imgf000027_0001
wherein each -NH2 unit hydrogen is optionally substituted by an alkyleneoxy unit having the formula:
(Rl0)χR2 wherein R is C2-C4 alkyiene, R2 is hydrogen, C ]-C4 alkyl, and mixtures thereof; x is from 1 to 50; y is from 3 to 10,000; iii) optionally at least 0.2%, preferably from 0.2% to 10%, more preferably from 0.2% to 5% by weight, of a cationic charge booster having the formula:
[H2N-R 1 -[N-R]m-[N-R-„-NH2 wherein R is C2-Cg alkyiene, m is from 3 to 70. n is from 0 to 35; wherein each hydrogen atom of said backbone is optionally substituted by an alkyleneoxy unit having the formula:
(Rl0)χR2 wherein Rl is C2-C4 alkyiene, R is hydrogen, C1-C4 alkyi, and mixtures thereof; x is from 1 to 50; iv) optionally at least 0.2%, preferably from 0.2% to 10%, more preferably from 0.2% to 5% by weight, of a cationic charge booster having the formula:
Figure imgf000028_0001
wherein R is substituted or unsubstituted C2-C12 alkyiene, substituted or unsubstituted C2-C12 hydroxyalkylene; each Rl is independently C1-C4 alkyl, each R2 is independently C!-C22 alkyl, C3-C22 alkenyl, R5-Q-(CH2)m-, wherein R5 is C1-C22 alkyl, and mixtures thereof; m is from 1 to 6; Q is a carbonyl unit as defined hereinabove; and mixtures thereof; X is a softener compatible anion; and v) mixtures thereof; and the balance carriers and adjunct ingredients, said adjunct ingredients selected from the group consisting of nonionic fabric softening agents, concentration aid, soil release agent, perfume, preservatives, stabilizers, colorants, optical brighteners, opacifiers, fabric conditioning agents, anti-shrinkage agents, anti-wrinkle agents, fabric crisping agents, spotting agents, germicides, fungicides, anti- corrosion agents, antifoam agents, and mixtures thereof.
PCT/US1997/016688 1996-09-19 1997-09-19 Fabric softeners having increased performance WO1998012292A1 (en)

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JP51491198A JP3190357B2 (en) 1996-09-19 1997-09-19 Fabric softener with enhanced performance
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