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WO1993006294A1 - Concentrated fabric-softening compositions - Google Patents

Concentrated fabric-softening compositions Download PDF

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Publication number
WO1993006294A1
WO1993006294A1 PCT/US1992/008048 US9208048W WO9306294A1 WO 1993006294 A1 WO1993006294 A1 WO 1993006294A1 US 9208048 W US9208048 W US 9208048W WO 9306294 A1 WO9306294 A1 WO 9306294A1
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WO
WIPO (PCT)
Prior art keywords
acid
composition
softening
compositions
chelating agent
Prior art date
Application number
PCT/US1992/008048
Other languages
French (fr)
Inventor
Hugo Jean Marie Demeyere
Johan Maurice Theo De Poortere
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.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP5506335A priority Critical patent/JPH07505189A/en
Priority to CA002119767A priority patent/CA2119767A1/en
Publication of WO1993006294A1 publication Critical patent/WO1993006294A1/en

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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/461—Quaternised amin-amides from polyamines or heterocyclic compounds or polyamino-acids
    • 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
    • C11D1/58—Heterocyclic 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
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • 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
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/33—Amino carboxylic acids
    • 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
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/364—Organic compounds containing phosphorus containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/352—Heterocyclic compounds having five-membered heterocyclic rings
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • D06M13/473—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having five-membered heterocyclic rings
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • the present invention relates to concentrated fabric-softening compositions in liquid form, to be used in the rinse step of the laundry cycle.
  • Fabric-softening compositions to be added in the rinse step of a laundry cycle are well known in the art and have found wide-scale commercial application.
  • ester-containing fabric-softening actives have been disclosed, to be used in replacement of, or in combination with, conventional quaternary softening actives.
  • ester-containing actives include the imidazoline ester derivatives disclosed in e. g. GB 1,561,808 and further disclosed in e.g. EP-A- 345 842.
  • the present invention is based on the discovery that such a problem is surprisingly cured by the
  • the present invention encompasses concentrated fabric-softening compositions containing at least 10% by weight, preferably 15 to 25% by weight of an
  • imidazoline ester softening active of the formula is imidazoline ester softening active of the formula :
  • X and XI are, independently, C11-C21
  • hydrocarbyl groups preferably C13-C17 alkyl, and m and n are, independently, from 2 to 4, preferably 2, and a Bronstedt acid as levels such as to have a pH below 4, characterized in that, it contains a
  • chelating agent for heavy metal ions at levels of from 0.01% to 1%, preferably 0.05 to 0.2% of the composition.
  • compositions of the present invention contain at least 10%, preferably from 15% to 25% of a substituted imidazoline ester softening compound having the formula
  • X and X 1 are, independently, C 11 -C 21
  • hydrocarbyl groups preferably C 13 -C 17 alkyl, most preferably straight chain C 17 alkyl, and m and n are, independently, from 2 to 4, preferably m and n are both 2.
  • the total concentration of softener active cannot exceed about 40% by weight. It will be
  • substituents X and X 1 may optionally be substituted with various groups such as alkoxyl, hydroxyl, or can be branched, but such materials are not preferred herein.
  • X and/or X 1 may optionally be unsaturated (i.e., alkenyl groups).
  • the preferred substituted imidazoline ester softening compounds will hereinafter be referred to as di-alkyl imidazoline ester compounds. Most preferred is ditallow imidazoline ester.
  • the pH, measured in distilled water at 3% dilution of the present compositions should be not greater than 4, preferably from 2.5-4.
  • a Bronstedt acid having a pKa value of 6 or less is present in the present
  • suitable acids include the inorganic mineral acids, carboxylic acids, in particular the low molecular weight (C 1 -C 5 ) carboxylic acids, aromatic carboxylic acids, like benzoic acid, and alkylsulfonic acids.
  • Suitable ionorganic acids include HCl, HBr, H 2 SO 4 , HNO 3 and H 3 PO 4 .
  • Suitable organic acids include benzoic acid, formic, acetic, methylsulfonic and ethylsulfonic acid.
  • Preferred acids are phosphoric, formic, and methylsulfonic acid.
  • compositions herein comprise a liquid carrier, e.g., water, preferably a mixture of water and a C 1 -C 4 monohydric alcohol (e.g., ethanol, propanol,
  • a liquid carrier e.g., water, preferably a mixture of water and a C 1 -C 4 monohydric alcohol (e.g., ethanol, propanol,
  • compositions comprise from 60% to 98%, preferably from 70% to 95% of the liquid carrier.
  • amount of the C 1 -C 4 monohydric alcohol in the liquid carrier is from
  • the balance of the liquid carrier being water.
  • the chelating agents are present at levels of from 0.01% to 1% of the compositions herein, preferably from 0.05 to 0.2%.
  • the chelating agents for heavy metal ions useful herein include any material known in the art for that purpose. Suitable compounds include the following carboxylic acids and salts thereof : citric acid, tartaric acid, oxydisuccinic acid, ethylene diamine -N,N disuccinic acid, oxydiacetic acid, carboxymethyltartronic acid, carboxymethyloxysuccinic acid, tartrate monosuccinic acid/tartrate disuccinic acid blend at 80:20 weight ratio, as well as 2-dodecenyl succinic acid, and dodecyl succinic acid.
  • carboxylic acids and salts thereof include the following carboxylic acids and salts thereof : citric acid, tartaric acid, oxydisuccinic acid, ethylene diamine -N,N disuccinic acid, oxydiacetic acid, carboxymethyltartronic acid, carboxymethyloxysuccinic acid, tartrate monosuccinic acid/tartrate disuccinic acid blend at 80:
  • This category also includes polycarboxylic acids and salts thereof, such as polyacrylates and copolymers of maleic and acrylic acids.
  • nitrilotriacetic acid ethylene diamine tetracetic acid, cyclo ethyiene diamine tetracetic acid, trans 1,2 diamino cyclohexane N,N,N',N' tetraacetic
  • tetracetic acid diethylene triaminopentacetic acid, N-glyceryl imino diacetic acid, N(-2 hydroxypropyl) iminodiacetic acid;
  • tetramethylenephosphonic acid and diethylene triamine pentamethylenephosphonic acid are also suitable as chelating agents hereof.
  • Fully-formulated fabric softening compositions may optionally contain, in addition to the substituted imidazoline ester softening compounds of the formula herein, the liquid carrier and the acid, one or more of the following ingredients.
  • Quaternary ammonium softening agents may optionally contain, in addition to the substituted imidazoline ester softening compounds of the formula herein, the liquid carrier and the acid, one or more of the following ingredients.
  • compositions of the present invention can further comprise a di(higher alkyl) quaternary
  • compositions herein can contain from 0% to 25% (preferably from 0.1% to 10%) of the di(higher alkyl) quaternary ammonium softening agent.
  • quaternary softening agents useful herein are selected from the group of
  • R 2 is an acyclic aliphatic C 15 -C 22
  • R 3 is a C 1 -C 4 saturated alkyl or hydroxyalkyl group, R 4 is selected from R 2 and R 3 , and A is an anion;
  • Rapidly biodegradable compounds of formula (i) where R 2 , and possibly R 4 , are interupted by ester groups, are disclosed in EPA 239 910.
  • R 1 is an acyclic aliphatic C 15 -C 22
  • R 2 is a divalent alkylene group having 1 to 3 carbon atoms
  • R 5 and R 8 are C 1 -C 4 saturated alkyl or hydroxyalkyl groups
  • A- is an anion
  • n is equal to from 1 to 5, and R 1 , R 2 , R 5 and A- are as defined above.
  • R 1 C 15 -C 17 saturated alkyl
  • R 2 C 1 -C 4 saturated alkyl
  • Z NH or O
  • A- is an anion.
  • dialkyldimethylammoniums salts such as
  • di (hydrogenated tallow) dimethylammonium chloride dibehenyldimethylammonium chloride.
  • R 1 is an acyclic aliphatic C 15 - C 17 hydrocarbon group
  • R 2 is an ethylene group
  • R 5 is a methyl group
  • R 8 is a hydroxyalkyl group
  • A is a methylsulfate anion
  • component (iv) are 1-methyl-1- tallowamino-ethyl-2-tallowimidazolinium methylsulfate and 1-methyl-1-(hydrogenated tallowamidoethyl)- methylsulfate.
  • the ratio of quaternary ammonium salt to cyclicamine should not exceed 10:1, and preferably does not exceed 2:1.
  • the aqueous dispersion of quaternary softening agent is prepared in a conventional way, typically by injecting the quaternary material in a molten form in a batch containing water, with continuous agitation.
  • said concentrated composition will, immediately after step d) be added to the aqueous dispersion of quaternary ammonium compound.
  • concentrated composition obtained after step d) will first be cooled to a temperature of from 15 to 25oC, (room temperature) and then some time will be allowed for e.g. storage, shipment of the concentrated
  • the viscosity of the finished product will be in a range of 20 to 500 cp, preferably 50 to 150 cp.
  • Optional co-softening agents
  • the co-softening agents for use herein can be selected from fatty acid esters of polyhydric alcohols having up to 8 carbon atoms such as described in DE-A- 26 31 114.
  • fatty acid esters of polyhydric alcohols having up to 8 carbon atoms such as described in DE-A- 26 31 114.
  • the like esters include sorbitan esters and glycerol esters such as sorbitan monostearate, sorbitan monooleate, glycerol mono-di- and tri-fatty acid esters wherein the acid is selected from stearic, oleic, lauric, capric, caprylic,
  • an individual glycerol can be esterified by identical fatty acid groups or by mixed esters e.g. glycerol monostearatedioleate.
  • Polyethyleneglycol esters monostearate, wherein the polyethyleneglycol moiety has a molecular weight in the range from 200 to 400 are also included in that class.
  • Fatty acid esters of monohydric alcohols having at least 4 carbon atoms such as isobutyl stearate and ethyl hexyl stearate can also be useful.
  • Additional co-softening agents which can be used are : glycerol, diglycerol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol,
  • dihexylene glycol polyethylene glycol (MW 200- 100.000), polypropylene glycol (MW 200-100.000), polyvinylalcohol, polyoxyethylenepolyoxypropylene copolymers, polypropylene glycol (MW 900), glucose methylether, butyldiglycolether,
  • propyleneglycolmonoethyl or ethyl ether ethylene carbonate, propylene carbonate.
  • alkylpolyglucosides of the general formula R 2 O(CnH 2n O) t (glucosyl) x wherein R 2 is alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl and mixtures thereof wherein the alkyl chain has from 8 to 18 carbon atoms, t is from 0 to 2 and x from 2 to 7, can also be used in the composition.
  • R 2 is alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl and mixtures thereof wherein the alkyl chain has from 8 to 18 carbon atoms, t is from 0 to 2 and x from 2 to 7, can also be used in the composition.
  • These glucosides exhibit desirable solvent properties and in addition can confer fiber benefits such as softness.
  • Lanolins and derivatives and paraffins having from 16 to 20 carbon atoms constitute another example of non-ionic agents which can be used if desired.
  • Low melting oils from animal, vegetable or mineral origin are representative of this class of materials.
  • Carnation oil R Jojoba oil R and Sunflower oil are specific examples which are found to work.
  • R 1 COOR 2 wherein R 1 is a straight or branched chain alkyl or alkenyl group having from 8 to 23 carbon atoms and R 2 is hydrogen or an alkyl or hydroxyalkyl group having 1-4 carbon atoms.
  • Highly preferred materials of this class are the C 10 to C 20 saturated fatty acids, especially lauric acid, myristic acid, palmitic acid and stearic acid.
  • ethoxylates such as LUTENSOL ® compounds available from BASF, as well as branched C 8 _ 18 akanols such as EXXAL compounds available from EXXON.
  • Clay materials such as the low ion-exchange-capacity ones describerd in EPA 150.531 can also be used.
  • cation-active amines namely primary, secondary and tertiary amines having, at least, one straight-chain organic group of from 12 to 22 carbon atoms.
  • Preferred amines of this class are
  • ethoxyamines such as monotallow-dipolyethoxyamine, having a total of 2to 30 ethoxygroups per molecule.
  • Suitable are also diamines such as tallow-N,N', N'- tris (2-hydroxyethyl)-1,3-propylenediamine, or C 16-18 - alkyl-N-bis(2-hydroxyethyl) amines, examples of above amines are these sold under the trade name GENAMIN C, S, D, and T, by Hoechst.
  • co-softening agents above are used at ratios of from 5:1 of 20:1 of quaternary softening agent to co- softening agent.
  • preferred ratio is from 8:1 to 10:1.
  • silicone components such as described in
  • additives are normally incorporated at their conventional low levels e.g. from 0.001% to 5%, in the dilution step of the concentrates herein.
  • compositions were prepared :
  • Example 1 and 2 were stored for 3 weeks at 50oC and compared with similar compositions not containing citric acid, stored under the same conditions; the compositions of Example 1 and 2 did not develop any perfume off-note, contrary to the reference compositions.
  • compositions are also prepared.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Concentrated fabric-softening compositions are disclosed, containing at least 10 % by weight of a di-long chain imidazoline ester, preferably ditallowimidazoline ester, and having a pH below 4, characterized in that they contain from 0.01 % to 1 % of a chelating agent for heavy metal ions, to cure perfume off-note development under storage.

Description

CONCENTRATED FABRIC-SOFTENING COMPOSITIONS
Technical Field
The present invention relates to concentrated fabric-softening compositions in liquid form, to be used in the rinse step of the laundry cycle.
Background
Fabric-softening compositions to be added in the rinse step of a laundry cycle are well known in the art and have found wide-scale commercial application.
In addition to achieving excellent fabric-softening performance, it has been, in recent years, the
objective of fabric softener manufacturers to provide compositions which have an increased biodegradability. Accordingly, ester-containing fabric-softening actives have been disclosed, to be used in replacement of, or in combination with, conventional quaternary softening actives. Such ester-containing actives include the imidazoline ester derivatives disclosed in e. g. GB 1,561,808 and further disclosed in e.g. EP-A- 345 842.
It has been found, however, that concentrated compositions containing said ester imidazoline
compounds have a tendency to develop an odor off-note, on prolonged storage.
The present invention is based on the discovery that such a problem is surprisingly cured by the
incorporation in said concentrated compositions of a small amount of chelating agent for heavy metal ions.
In U.S. Patent 3, 756,950 are disclosed fabric- softening compositions containing conventional
quaternary ammonium softening actives and an acid salt of amino-carboxylic acid chelating agent, to decrease fabric yellowing.
Summary of the Invention
The present invention encompasses concentrated fabric-softening compositions containing at least 10% by weight, preferably 15 to 25% by weight of an
imidazoline ester softening active of the formula :
Figure imgf000004_0001
wherein X and XI are, independently, C11-C21
hydrocarbyl groups, preferably C13-C17 alkyl, and m and n are, independently, from 2 to 4, preferably 2, and a Bronstedt acid as levels such as to have a pH below 4, characterized in that, it contains a
chelating agent for heavy metal ions, at levels of from 0.01% to 1%, preferably 0.05 to 0.2% of the composition. Detailed Description of the Invention
Substituted imidazoline ester softening compound
The compositions of the present invention contain at least 10%, preferably from 15% to 25% of a substituted imidazoline ester softening compound having the formula
Figure imgf000005_0001
wherein X and X1 are, independently, C11-C21
hydrocarbyl groups, preferably C13-C17 alkyl, most preferably straight chain C17 alkyl, and m and n are, independently, from 2 to 4, preferably m and n are both 2. The total concentration of softener active cannot exceed about 40% by weight. It will be
understood that substituents X and X1 may optionally be substituted with various groups such as alkoxyl, hydroxyl, or can be branched, but such materials are not preferred herein. In addition X and/or X1 may optionally be unsaturated (i.e., alkenyl groups). The preferred substituted imidazoline ester softening compounds will hereinafter be referred to as di-alkyl imidazoline ester compounds. Most preferred is ditallow imidazoline ester.
pH
The pH, measured in distilled water at 3% dilution of the present compositions should be not greater than 4, preferably from 2.5-4. To achieve such a pH, a Bronstedt acid having a pKa value of 6 or less, is present in the present
composition.
Examples of suitable acids include the inorganic mineral acids, carboxylic acids, in particular the low molecular weight (C1-C5) carboxylic acids, aromatic carboxylic acids, like benzoic acid, and alkylsulfonic acids.
Suitable ionorganic acids include HCl, HBr, H2SO4, HNO3 and H3PO4. Suitable organic acids include benzoic acid, formic, acetic, methylsulfonic and ethylsulfonic acid. Preferred acids are phosphoric, formic, and methylsulfonic acid.
Liquid carrier
The compositions herein comprise a liquid carrier, e.g., water, preferably a mixture of water and a C1-C4 monohydric alcohol (e.g., ethanol, propanol,
isopropanol, butanol, and mixtures thereof),
isopropanol being preferred. These compositions comprise from 60% to 98%, preferably from 70% to 95% of the liquid carrier. Preferably, the amount of the C1-C4 monohydric alcohol in the liquid carrier is from
5% to 50% by weight of the softening compounds, the balance of the liquid carrier being water.
The chelating agent for heavy metal ions
The chelating agents are present at levels of from 0.01% to 1% of the compositions herein, preferably from 0.05 to 0.2%.
The chelating agents for heavy metal ions useful herein include any material known in the art for that purpose. Suitable compounds include the following carboxylic acids and salts thereof : citric acid, tartaric acid, oxydisuccinic acid, ethylene diamine -N,N disuccinic acid, oxydiacetic acid, carboxymethyltartronic acid, carboxymethyloxysuccinic acid, tartrate monosuccinic acid/tartrate disuccinic acid blend at 80:20 weight ratio, as well as 2-dodecenyl succinic acid, and dodecyl succinic acid.
This category also includes polycarboxylic acids and salts thereof, such as polyacrylates and copolymers of maleic and acrylic acids.
Other suitable compounds are the following amino- carboxylic acids and salts thereof, as
nitrilotriacetic acid, ethylene diamine tetracetic acid, cyclo ethyiene diamine tetracetic acid, trans 1,2 diamino cyclohexane N,N,N',N' tetraacetic
monohydrate (CHELCD) , hydroxyethylenediamine
tetracetic acid, diethylene triaminopentacetic acid, N-glyceryl imino diacetic acid, N(-2 hydroxypropyl) iminodiacetic acid;
Polyamino polyalkylene phosphonic acids and salts thereof such as ethylenediamine
tetramethylenephosphonic acid and diethylene triamine pentamethylenephosphonic acid are also suitable as chelating agents hereof.
Optional ingredients
Fully-formulated fabric softening compositions may optionally contain, in addition to the substituted imidazoline ester softening compounds of the formula herein, the liquid carrier and the acid, one or more of the following ingredients. Quaternary ammonium softening agents
The compositions of the present invention can further comprise a di(higher alkyl) quaternary
ammonium softening agent. The compositions herein can contain from 0% to 25% (preferably from 0.1% to 10%) of the di(higher alkyl) quaternary ammonium softening agent.
The quaternary softening agents useful herein are selected from the group of
(i) acyclic quaternary ammonium salts having the formula:
Figure imgf000008_0001
wherein R2 is an acyclic aliphatic C15-C22
hydrocarbon group which may be interupted by ester groups. R3 is a C1-C4 saturated alkyl or hydroxyalkyl group, R4 is selected from R2 and R3, and A is an anion;
Rapidly biodegradable compounds of formula (i) where R2, and possibly R4, are interupted by ester groups, are disclosed in EPA 239 910.
(ii) diamido quaternary ammonium salts having the formula :
Figure imgf000008_0002
wherein R1 is an acyclic aliphatic C15-C22
hydrocarbon group, R2 is a divalent alkylene group having 1 to 3 carbon atoms, R5 and R8 are C1-C4 saturated alkyl or hydroxyalkyl groups, and A- is an anion;
(iii) diamido alkoxylated quaternary ammonium salts having the formula :
Figure imgf000009_0001
wherein n is equal to from 1 to 5, and R1, R2, R5 and A- are as defined above.
(iv) quaternary imidazolinium compounds having the formula :
Figure imgf000009_0002
wherein R1 = C15-C17 saturated alkyl, R2 = C1-C4 saturated alkyl, Z = NH or O, and A- is an anion.
Examples of Component (i) are the well-known
dialkyldimethylammoniums salts such as
ditallowdimethylammonium chloride,
ditallowdimethylammonium methylsulfate,
di (hydrogenated tallow) dimethylammonium chloride, dibehenyldimethylammonium chloride.
Examples of Component (ii) and (iii) are
methylbis(tallowamidoethyl) (2-hydroxyethyl) ammonium methylsulfate and methyIbis (hydrogenated
tallowamidoethyl) (2-hydroxyethyl) ammonium
methylsulfate, wherein R1 is an acyclic aliphatic C15- C17 hydrocarbon group, R2 is an ethylene group, R5 is a methyl group, R8 is a hydroxyalkyl group and A is a methylsulfate anion; these materials are available from Sherex Chemical Company under the trade names VarisoftR 222 and VarisoftR 110, respectively.
Examples of component (iv) are 1-methyl-1- tallowamino-ethyl-2-tallowimidazolinium methylsulfate and 1-methyl-1-(hydrogenated tallowamidoethyl)- methylsulfate.
The ratio of quaternary ammonium salt to cyclicamine should not exceed 10:1, and preferably does not exceed 2:1.
The aqueous dispersion of quaternary softening agent is prepared in a conventional way, typically by injecting the quaternary material in a molten form in a batch containing water, with continuous agitation.
Once this dispersion is prepared, the concentrated composition resulting from steps a) to d) will be added to it;
In case of a continuous process, said concentrated composition will, immediately after step d) be added to the aqueous dispersion of quaternary ammonium compound.
In an alternative and convenient way, the
concentrated composition obtained after step d) will first be cooled to a temperature of from 15 to 25ºC, (room temperature) and then some time will be allowed for e.g. storage, shipment of the concentrated
composition, before it is added to the aqueous
dispersion of quaternary softening agent.
In any case, the viscosity of the finished product will be in a range of 20 to 500 cp, preferably 50 to 150 cp. Optional co-softening agents
The co-softening agents for use herein can be selected from fatty acid esters of polyhydric alcohols having up to 8 carbon atoms such as described in DE-A- 26 31 114. Examples of the like esters include sorbitan esters and glycerol esters such as sorbitan monostearate, sorbitan monooleate, glycerol mono-di- and tri-fatty acid esters wherein the acid is selected from stearic, oleic, lauric, capric, caprylic,
caproic, valeric, butyric, propionic and acetic acid; an individual glycerol can be esterified by identical fatty acid groups or by mixed esters e.g. glycerol monostearatedioleate. Polyethyleneglycol esters monostearate, wherein the polyethyleneglycol moiety has a molecular weight in the range from 200 to 400 are also included in that class. Fatty acid esters of monohydric alcohols having at least 4 carbon atoms such as isobutyl stearate and ethyl hexyl stearate can also be useful.
Additional co-softening agents which can be used are : glycerol, diglycerol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol,
dihexylene glycol, polyethylene glycol (MW 200- 100.000), polypropylene glycol (MW 200-100.000), polyvinylalcohol, polyoxyethylenepolyoxypropylene copolymers, polypropylene glycol (MW 900), glucose methylether, butyldiglycolether,
diethyleneglycolmonobutylether,
propyleneglycolmonoethyl or ethyl ether, ethylene carbonate, propylene carbonate.
Useful also are alkylpolyglucosides of the general formula R2O(CnH2nO)t (glucosyl)x wherein R2 is alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl and mixtures thereof wherein the alkyl chain has from 8 to 18 carbon atoms, t is from 0 to 2 and x from 2 to 7, can also be used in the composition. These glucosides exhibit desirable solvent properties and in addition can confer fiber benefits such as softness.
Lanolins and derivatives and paraffins having from 16 to 20 carbon atoms constitute another example of non-ionic agents which can be used if desired. Low melting oils from animal, vegetable or mineral origin are representative of this class of materials.
Carnation oilR, Jojoba oilR and Sunflower oil are specific examples which are found to work.
Another important class of co-softening agents is represented by materials of the general formula :
R1COOR2 wherein R1 is a straight or branched chain alkyl or alkenyl group having from 8 to 23 carbon atoms and R2 is hydrogen or an alkyl or hydroxyalkyl group having 1-4 carbon atoms.
Highly preferred materials of this class are the C10 to C20 saturated fatty acids, especially lauric acid, myristic acid, palmitic acid and stearic acid.
Also suitable are linear fatty C8-18 akanol
ethoxylates such as LUTENSOL® compounds available from BASF, as well as branched C8_18 akanols such as EXXAL compounds available from EXXON.
Clay materials such as the low ion-exchange-capacity ones describerd in EPA 150.531 can also be used.
The co-softening agents above can be used in
combination with cation-active amines, namely primary, secondary and tertiary amines having, at least, one straight-chain organic group of from 12 to 22 carbon atoms. Preferred amines of this class are
ethoxyamines, such as monotallow-dipolyethoxyamine, having a total of 2to 30 ethoxygroups per molecule. Suitable are also diamines such as tallow-N,N', N'- tris (2-hydroxyethyl)-1,3-propylenediamine, or C16-18- alkyl-N-bis(2-hydroxyethyl) amines, examples of above amines are these sold under the trade name GENAMIN C, S, D, and T, by Hoechst.
The co-softening agents above are used at ratios of from 5:1 of 20:1 of quaternary softening agent to co- softening agent.
In the instance for fatty acids are used, a
preferred ratio is from 8:1 to 10:1.
Further other optional ingredients for use herein include silicone components such as described in
British Patent No. 1,549,180, emulsifiers,
preservatives, germicides, dyes, bactericides,
stabilizers, brighteners, opacifiers, photoactivators, copolymeric carboxylates having sequestering
properties, soil release agents, bleaches, bleach activators, and anti-yellowing agents. Suitable polymeric soil-release agents are disclosed in
EP-A-220 156.
These additives are normally incorporated at their conventional low levels e.g. from 0.001% to 5%, in the dilution step of the concentrates herein.
The following examples illustrate the present invention.
The following compositions were prepared :
Figure imgf000014_0001
The compositions of Example 1 and 2 were stored for 3 weeks at 50ºC and compared with similar compositions not containing citric acid, stored under the same conditions; the compositions of Example 1 and 2 did not develop any perfume off-note, contrary to the reference compositions.
The following compositions are also prepared
Figure imgf000014_0002
* diethylene triamine pentamethylene phosphonic acid ** trans 1,2 diamino cyclohexane N,N,N',N' tetraacetic monohydrate

Claims

WHAT IS CLAIMED IS:
1. A concentrated fabric-softening composition containing at least 10% by weight of an imidazoline ester softening active of the formula :
Figure imgf000015_0001
wherein X and XI are, independently, C11-C21
hydrocarbyl groups, preferably C13-C17 alkyl, and m and n are, independently, from 2 to 4, preferably 2, and a Bronstedt acid as levels such as to have a pH below 4, characterized in that, it contains a
chelating agent for heavy metal ions, at levels of from 0.01% to 1% of the composition.
2. The composition of claim 1 wherein said
imidazoline ester is ditallow imidazoline ester.
3. The composition of claims 1-2 wherein said chelating agent is selected from the group of
carboxylic acids, polycarboxylic acids, amino
carboxylic acids, polyamino polyalkylenephosphonic acids, and salts thereof.
4. The composition of claim 3 wherein said chelating agent is selected from the group of citric acid, EDTA, and diethylene triamine pentamethylene phosphonic acid.
5. The composition of claims 1-4 wherein the level of chelating agent is from 0. 05% to 0.2% .
6. The composition of claims 1-5 wherein the level of imidazoline ester is from 15% to 25%.
7. The composition of claims 1-6 wherein the pH of the composition is from 2.5 to 4.
PCT/US1992/008048 1991-09-27 1992-09-21 Concentrated fabric-softening compositions WO1993006294A1 (en)

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WO1998017750A1 (en) * 1996-10-21 1998-04-30 The Procter & Gamble Company Concentrated, fabric softening composition
US5767052A (en) * 1995-01-12 1998-06-16 The Procter & Gamble Company Stabilized liquid fabric softener compositions
US10570567B2 (en) 2016-02-29 2020-02-25 Kemira Oyj Softener composition

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US5484540A (en) * 1991-03-08 1996-01-16 The Procter & Gamble Company Concentrated fabric softening compositions
US5433869A (en) * 1992-12-22 1995-07-18 Colgate-Palmolive Co. Liquid fabric conditioning composition containing amidoamine softening compound
US5403499A (en) * 1993-04-19 1995-04-04 Lever Brothers Company, Division Of Conopco, Inc. Concentrated fabric conditioning compositions
US5468398A (en) * 1993-05-20 1995-11-21 Colgate-Palmolive Company Liquid fabric softening composition
HUP9802404A3 (en) * 1995-07-11 2000-06-28 Procter And Gamble Company Cin Concentrated, stable, especially transparent fabric softening composition, material capable of forming it and process for producing it
EP0768369A1 (en) * 1995-10-11 1997-04-16 The Procter & Gamble Company Fabric softener compositions
JP4781527B2 (en) * 1997-07-29 2011-09-28 ザ プロクター アンド ギャンブル カンパニー Concentrated stable, preferably transparent fabric softening composition containing an amine fabric softener
US20250122445A1 (en) * 2022-03-10 2025-04-17 Conopco, Inc., D/B/A Unilever Concentrated fabric conditioner

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US5686376A (en) * 1995-01-12 1997-11-11 The Procter & Gamble Company Chelating agents for improved color fidelity
US5767052A (en) * 1995-01-12 1998-06-16 The Procter & Gamble Company Stabilized liquid fabric softener compositions
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WO1998017750A1 (en) * 1996-10-21 1998-04-30 The Procter & Gamble Company Concentrated, fabric softening composition
US10570567B2 (en) 2016-02-29 2020-02-25 Kemira Oyj Softener composition
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EP0534009A1 (en) 1993-03-31
PT100908A (en) 1993-11-30
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MX9205493A (en) 1993-04-01
AR246566A1 (en) 1994-08-31

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