EP0523287A1 - Perfume additives for fabric-softening compositions - Google Patents

Perfume additives for fabric-softening compositions Download PDF

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Publication number
EP0523287A1
EP0523287A1 EP91201887A EP91201887A EP0523287A1 EP 0523287 A1 EP0523287 A1 EP 0523287A1 EP 91201887 A EP91201887 A EP 91201887A EP 91201887 A EP91201887 A EP 91201887A EP 0523287 A1 EP0523287 A1 EP 0523287A1
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EP
European Patent Office
Prior art keywords
perfume
softening
additive according
softening active
fabric
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP91201887A
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German (de)
French (fr)
Inventor
Hugo Jean Marie Demeyere
Ann Appeltants
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to EP91201887A priority Critical patent/EP0523287A1/en
Priority to PCT/US1992/005686 priority patent/WO1993001794A1/en
Priority to CA 2113613 priority patent/CA2113613C/en
Priority to JP5502838A priority patent/JPH06509611A/en
Priority to IE922340A priority patent/IE922340A1/en
Priority to MX9204224A priority patent/MX9204224A/en
Priority to PT10070692A priority patent/PT100706A/en
Publication of EP0523287A1 publication Critical patent/EP0523287A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0034—Fixed on a solid conventional detergent ingredient
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/12—Water-insoluble compounds
    • C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
    • 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
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay

Definitions

  • the present invention relates to perfume additives for use in combination with fabric-softening compositions.
  • Fabric-softening compositions to be added in the rinse step of a laundry cycle are well known.
  • compositions can be defined as the improvement of fabrics aesthetics/feel, after a wash cycle; this is why, in addition to softness, perfume delivery on fabrics from such compositions is an especially important aspect, and continuous efforts are made to improve such perfume delivery, so as to make it not only consumer-noticeable, but also long-lasting.
  • EP-A-0 397 245 and EP-A-397 246 have been described perfume particles wherein perfume is dispersed within certain water-insoluble polymeric carrier materials, and the resulting particles are used in fabric cleaning or conditioning compositions. Not all perfume compositions, however, are compatible with said polymeric carrier materials.
  • Such a carrier system consists of porous silica onto which a mixture, at specific ratios, of perfume and softening active is adsorbed.
  • porous spheroidal silica per se as carrier for a wide range of material including perfumes, has been disclosed in EP-A-294 206, not relating to softening of fabrics nor any combination with softening active.
  • the present invention relates to a perfume additive in granular form for use with fabric-softening compositions, containing :
  • the present invention also encompasses the use of said additives as single doses during use of fabric softening compositions, or the preparation of ready-to-use fabric softening compositions out of concentrates.
  • the porous silica useful herein is a precipitated spheroidal silica, having a particle size not exceeding 500 micrometers.
  • the silica herein typically has a pore volume in the range 25 to 75%.
  • This silica is further characterized by a BET surface area* superior to 50m2/g (DIN 66131) and a high absorption value.
  • the absorption can be expressed as Dibutylphtalate (DBP) number, this DBP number should be above 100g/100g, preferably above 200g/100g (DIN 53601, ASTM D 2414). * measured according to the method developed by Brunauer, Emmet and Teller (BET), J. Amer. Chem. Soc. 60, 309 (1938).
  • BET Brunauer, Emmet and Teller
  • Porous silica corresponding to the above specifications is available under the trade name Sipernat R from Degussa.
  • the additives herein contain from 20% to 70% of porous silica.
  • the characterizing feature of the present invention is that perfume is mixed with a softening active before being adsorbed onto the porous silica.
  • the ratio of perfume to softening active is from 1:10 to 5:1, preferably 1:5 to 3:1.
  • Perfume in the sense of perfume components or compositions of perfume components, can be any odorifirous materials or any materials which act as a malodour counteractent.
  • the perfume will most often be liquid at ambient temperatures, but also can be liquified solid such as the various camphoraceous perfumes known in the art.
  • the perfume can be relatively simple in composition or can comprise highly sophisticated, compact mixtures of natural or synthetic chemical components, all chosen to provide any desired odour.
  • perfumes are those odorous materials that deposit on fabrics during the laundry process and are detectable by people with normal olfactory sensitivity. Many of the perfume ingredients along with their odor character and their physical and chemical properties are given in "Perfume and Flavor chemicals (aroma chemicals)", Stephen Arctender, Vols. I and II, Aurthor, Montclair, H.J. and the Merck Index, 8th Edition, Merck & Co., Inc. Rahway, N.J. Perfume components and compositions can also be found in the art, e.g. US Patent Nos. 4,145,184, 4,152,272, 4,209,417 or 4,515,705.
  • perfume use includes materials such as aldehydes, ketones, esters and the like. More commonly, naturally occurring plant and animal oils and exudates comprising complex mixtures of various chemical components are known for use as perfume, and such materials can be used herein.
  • Typical perfumes can comprise e.g. woody/earthy bases containing exotic materials such as sandalwood oil, civet and patchouli oil.
  • the perfume also can be of a light floral fragrance e.g. rose or violet extract. Further the perfume can be formulated to provide desirable fruity odours e.g. lime, limon or orange.
  • perfume components and compositions are anetole, benzaldehyde, benzyl acetate, benzyl alcohol, benzyl formate, iso-bornyl acetate, camphene, cis-citral (neral), citronellal, citronellol, citronellyl acetate, paracymene, decanal, dihydrolinalool, dihydromyrcenol, dimethyl phenyl carbinol, eucalyptol, geranial, geraniol, geranyl acetate, geranyl nitrile, cis-3-hexenyl acetate, hydroxycitronellal, d-limonene, linalool, linalool oxide, linalyl acetate, linalyl propionate, methyl anthranilate, alpha-methyl ionone, methyl nonyl acetaldehyde, methyl phen
  • Di-long chain quaternary ammonium compounds are of the formula : wherein R1 and R2 are C1 ⁇ 4 saturated alkyl groups or hydroxyalkyl groups and R3 and R4 are acyclic aliphatic C8 ⁇ 30, preferably C12 ⁇ 23, more preferably C15 ⁇ 22 hydrocarbon groups which may be intempted by ester linkages, and A is an anion.
  • Preferred compounds of the formula above for use herein include the well known ditallowdimethyl ammonium chloride (DTDMAC), ditallowdimethyl ammonium methyl sulfate, and di(hydrogetated tallow)dimethyl ammonium chloride.
  • DTDMAC ditallowdimethyl ammonium chloride
  • ditallowdimethyl ammonium methyl sulfate ditallowdimethyl ammonium methyl sulfate
  • di(hydrogetated tallow)dimethyl ammonium chloride di(hydrogetated tallow)dimethyl ammonium chloride
  • Examples of such mixtures are the alkyl radicals obtained from coconut oil, "soft” (non-hardened) tallow, and hardened tallow;
  • X is wherein T is O or NR5, R5 being H or C1-C4 alkyl, preferably H, and R4 is a divalent C1-C3 alkylene group or (C2H4O) m , wherein m is a number of from 1 to 8; or X is R4.
  • imidazoline actives of the formula above are of the following formulae : wherein R1 is a tallow group.
  • Compounds of formula Ia are ditallowimidazolines, while compounds of formula Ib are ditallowimidazoline esters.
  • Quaternized di-long chain imidazoline compounds are of the formula : or mixtures thereof, wherein R and R1 are, independently, C11-C21 hydrocarbyl groups, preferably tallow, R2 is a C1-C4 hydrocarbyl group, preferably methyl, A is an anion, m is an integer from 2 to 4, preferably 2 and X is wherein T is O or NR5, R5 being H or C1-C4 alkyl, preferably H, and R4 is a divalent C1-C3 alkylene group or (C2H4O) m , wherein m is a number of from 1 to 8; or X is R4.
  • T is O and R4 is (CH2)2 (quaternized ditallow imidazoline ester).
  • Mono long-chain alkyl amines useful herein include compounds of the formula wherein R1 is a C8 ⁇ 30 acyclic aliphatic , preferably C12 ⁇ 23 hydrocarbon group which may be intempted by ester linkages, R2 and R3 are C1 ⁇ 4 saturated alkyl groups or hydroxyalkyl groups of the formula (CH2CH2O) n H where n is an integer from 1 to 5.
  • Mono alkyl quaternary ammonium compounds useful herein include compounds of the formula wherein R1 is an acyclic aliphatic C8 ⁇ 30, preferably C12 ⁇ 23 hydrocarbon group which may be interupted by ester linkages, R2, R3 and R4 are C1 ⁇ 4 saturated alkyl groups or hydroxyalkyl groups; and A is an anion.
  • a preferred mono-alkyl ammonium compound for use herein is cetyl trimethylammonium bromide.
  • Most preferred softening actives for use in the additives herein are ditallowdimethyl ammonium, ditallowimidazoline ester, quaternized ditallowimidazoline ester, and mixtures thereof.
  • the present additives may contain additional ingredients, which can be pre-mixed with the perfume and softening active before they are adsorbed onto the porous silicate, or added, after the adsorption is completed, to the particles.
  • Ingredients which can be pre-mixed with the perfume and softening active are selected from the group of
  • Preferred ingredients to be pre-mixed are the esters of C8-20 alcohols, in particular glyceryl monostearate.
  • the water-soluble coating/agglomerating materials can be selected from the group of polyvinyl alcohol, polyethylene glycol, sugars, polyacrylamides, polysaccharides and similar natural and synthetic polymers.
  • Dyes are typically used and can be added to the mix before adsorption onto silica, or sprayed on the formed particles as a last step.
  • a co-melt of the softening active and the perfume is typically made, possibly including an optional ingredient such as listed above.
  • the co-melt is adsorbed on porous silica, keeping the temperature, needed to keep the co-melt liquid, typically at 50°C; Adsorption can be achieved by adding the co-melt in portions to the pre-heated porous silica under agitation, or by spraying it on pre-heated porous silica in a "Nauta" type mixer.
  • the resulting free-flowing powder is cooled to a temperature ranging from 3°C to ambient, and sieved on an appropriate sieve (e.g. Mesh 22); the powder is then agglomerated in an agglomeration unit, such as a Plough Share Lödige, possibly with the addition of a coating/agglomeration material; the agglomerate is cooled and sieved over an appropriate sieve (e.g. Mesh 22).
  • an agglomeration unit such as a Plough Share Lödige
  • the perfume additives herein can either be used as single-dose additives for fabric softening compositions, during use, or as additives in the preparation of fabric-softening compositions out of concentrates, before use.
  • the present additives are used as single-dose additives to unperfumed fabric softening compositions during use; i.e. a dose of additive sufficient for a typical washing machine load is added to unperfumed fabric softening composition, prior to the rinse cycle of the laundry process.
  • Such an addition can conveniently be made in the dispenser of automatic washing machines; i.e. before starting the laundry cycle, an amount of fabric softening composition in liquid form is first poured into the dispenser of the washing machine, and the specific dose of perfume additive in granular form is added to said fabric softening composition sitting in the dispenser, and is dispersed therein.
  • the resulting mixture is then brought into contact with the fabrics, during the rinse cycle and the perfume is released onto the fabrics.
  • perfume additives herein is not limited to liquid fabric softening compositions since their granular form would render them quite suitable for use in combination with fabric-softening compositions in particulate form; such fabric-softening compositions can be used as is, or diluted with water before use.
  • the present additives can conveniently be packaged into single-dose sachets containing the powdered additive, such sachets being made available to the consumer in the form of boxes containing several of them, said sachets containing either the same perfume, or different perfumes so as to allow the consumer to choose the perfume to be left on the laundered fabrics, for each laundry cycle.
  • Dye is sprayed onto the above granulates; the formed granulates are used as perfume additives for fabric softening compositions.

Abstract

Granular perfume additives for rinse-added fabric softening compositions are disclosed, said additives containing a mixture of perfume and softening active in specified ratios, adsorbed onto particles of porous silica.

Description

    Technical Field
  • The present invention relates to perfume additives for use in combination with fabric-softening compositions.
    • Background
  • Fabric-softening compositions to be added in the rinse step of a laundry cycle are well known.
  • The overall function of such compositions can be defined as the improvement of fabrics aesthetics/feel, after a wash cycle; this is why, in addition to softness, perfume delivery on fabrics from such compositions is an especially important aspect, and continuous efforts are made to improve such perfume delivery, so as to make it not only consumer-noticeable, but also long-lasting.
  • In EP-A-0 397 245 and EP-A-397 246 have been described perfume particles wherein perfume is dispersed within certain water-insoluble polymeric carrier materials, and the resulting particles are used in fabric cleaning or conditioning compositions. Not all perfume compositions, however, are compatible with said polymeric carrier materials.
  • It has now been found a simple and inexpensive carrier system for perfumes, which is fully compatible with any perfume, and is very convenient to use.
  • Such a carrier system consists of porous silica onto which a mixture, at specific ratios, of perfume and softening active is adsorbed.
  • The use of porous spheroidal silica per se as carrier for a wide range of material including perfumes, has been disclosed in EP-A-294 206, not relating to softening of fabrics nor any combination with softening active.
    • Summary of the Invention
  • The present invention relates to a perfume additive in granular form for use with fabric-softening compositions, containing :
    • from 30% to 80% by weight of a mixture of perfume and softening active, in a ratio of perfume to softening active of 1:10 to 5:1, preferably 1:5 to 3:1
    • from 20% to 70% by weight of porous silica on which said mixture of perfume and softening active is adsorbed, the particle size of the porous silica not exceeding 500 micrometers.
  • The present invention also encompasses the use of said additives as single doses during use of fabric softening compositions, or the preparation of ready-to-use fabric softening compositions out of concentrates.
    • Detailed Description of the Invention The porous silica
  • The porous silica useful herein is a precipitated spheroidal silica, having a particle size not exceeding 500 micrometers.
  • The silica herein typically has a pore volume in the range 25 to 75%. This silica is further characterized by a BET surface area* superior to 50m²/g (DIN 66131) and a high absorption value. The absorption can be expressed as Dibutylphtalate (DBP) number, this DBP number should be above 100g/100g, preferably above 200g/100g (DIN 53601, ASTM D 2414).
    * measured according to the method developed by Brunauer, Emmet and Teller (BET), J. Amer. Chem. Soc. 60, 309 (1938).
  • Porous silica corresponding to the above specifications is available under the trade name SipernatR from Degussa. The additives herein contain from 20% to 70% of porous silica.
    • The perfume/softening active mixture
  • The characterizing feature of the present invention is that perfume is mixed with a softening active before being adsorbed onto the porous silica.
  • The ratio of perfume to softening active is from 1:10 to 5:1, preferably 1:5 to 3:1.
  • Perfume, in the sense of perfume components or compositions of perfume components, can be any odorifirous materials or any materials which act as a malodour counteractent. The perfume will most often be liquid at ambient temperatures, but also can be liquified solid such as the various camphoraceous perfumes known in the art. The perfume can be relatively simple in composition or can comprise highly sophisticated, compact mixtures of natural or synthetic chemical components, all chosen to provide any desired odour.
  • Useful perfumes are those odorous materials that deposit on fabrics during the laundry process and are detectable by people with normal olfactory sensitivity. Many of the perfume ingredients along with their odor character and their physical and chemical properties are given in "Perfume and Flavor chemicals (aroma chemicals)", Stephen Arctender, Vols. I and II, Aurthor, Montclair, H.J. and the Merck Index, 8th Edition, Merck & Co., Inc. Rahway, N.J. Perfume components and compositions can also be found in the art, e.g. US Patent Nos. 4,145,184, 4,152,272, 4,209,417 or 4,515,705.
  • A wide variety of chemicals are known for perfume use including materials such as aldehydes, ketones, esters and the like. More commonly, naturally occurring plant and animal oils and exudates comprising complex mixtures of various chemical components are known for use as perfume, and such materials can be used herein. Typical perfumes can comprise e.g. woody/earthy bases containing exotic materials such as sandalwood oil, civet and patchouli oil. The perfume also can be of a light floral fragrance e.g. rose or violet extract. Further the perfume can be formulated to provide desirable fruity odours e.g. lime, limon or orange.
  • Particular examples of useful perfume components and compositions are anetole, benzaldehyde, benzyl acetate, benzyl alcohol, benzyl formate, iso-bornyl acetate, camphene, cis-citral (neral), citronellal, citronellol, citronellyl acetate, paracymene, decanal, dihydrolinalool, dihydromyrcenol, dimethyl phenyl carbinol, eucalyptol, geranial, geraniol, geranyl acetate, geranyl nitrile, cis-3-hexenyl acetate, hydroxycitronellal, d-limonene, linalool, linalool oxide, linalyl acetate, linalyl propionate, methyl anthranilate, alpha-methyl ionone, methyl nonyl acetaldehyde, methyl phenyl carbinyl acetate, laevo-menthyl acetate, menthone, iso-menthone, myrcene, myrcenyl acetate, myrcenol, nerol, neryl acetate, nonyl acetate, phenyl ethyl alcohol, alpha-pinene, beta-pinene, gamma-terpinene, alpha-terpineol, beta-terpineol, terpinyl acetate, vertenex (para-tertiary-butyl cyclohexyl acetate), amyl cinnamic aldehyde, iso-amyl salicylate, beta-caryophyllene, aldehyde, iso-amyl salicylate, beta-carophyllene, cedrene, cinnamic alcohol, couramin, dimethyl benzyl carbinyl acetate, ethyl vanillin, eugenol, iso-eugenol, flor acetate, heliotrophine, 3-cis-hexenyl salicylate, hexyl silicylate, lilial (para-tertiarybutyl-alpha-methyl hydrocinnamic aldehyde), gamma-methyl ionone, nerolidol, patchouli alcohol, phenyl hexanol, beta-selinene, trichloromethyl phenyl carbinyl acetate, triethyl citrate, vanillin, veratraldehyde, alpha-cedrene, beta-cedrene, C₁₅H₂₄sesquiterpenes, benzophenone, benzyl salicylate, ethylene brassylate, galaxolide (1,3,4,6,7,8-hexahydro-4,6,7,8,8,-hexamethyl-cyclo-penta-gamma-2-benzopyran), hexyl cinnamic aldehyde, lyral (4-(4-hydroxy-4-methyl phenyl)-3-cyclohexene-10-carboxaldehyde), methyl cedrylone, methyl dihydro jasmonate, methyl-beta-naphthyl ketone, musk ambrette, musk idanone, musk ketone, musk tibetine, musk xylol, aurantiol and phenylethyl phenyl acetate.
  • The softening active for use in the perfume additives herein can be selected from the group of di-long chain quaternary ammonium compounds, di-long chain imidazoline compounds, di-long chain quaternized imidazoline compounds, as well as certain mono long-chain alkyl quaternary ammonium compounds and mono long-chain alkyl amines.
  • Di-long chain quaternary ammonium compounds are of the formula :
    Figure imgb0001
       wherein R₁ and R₂ are C₁₋₄ saturated alkyl groups or hydroxyalkyl groups and R₃ and R₄ are acyclic aliphatic C₈₋₃₀, preferably C₁₂₋₂₃, more preferably C₁₅₋₂₂ hydrocarbon groups which may be intempted by ester linkages, and A is an anion.
  • Preferred are compounds of the formula above wherein R₁ and R₂ are methyl groups, and R₃ and R₄ are derived from fatty materials such as tallow.
  • Preferred compounds of the formula above for use herein include the well known ditallowdimethyl ammonium chloride (DTDMAC), ditallowdimethyl ammonium methyl sulfate, and di(hydrogetated tallow)dimethyl ammonium chloride.
  • Compounds of the formula above wherein R3 and R4 are interrupted by ester groups are disclosed in EP-A-239 910; such compounds have the advantage of being more rapidly biodegradable than the above-described compounds; preferred is N,N di(2-tallowyloxy-2-oxo-ethyl)N,N dimethylammonium chloride.
  • Di-long chain imidazoline compounds are of the formula
    Figure imgb0002
       wherein m is an integer from 2 to 4, preferably 2, and R₁ and R₂ are, independently, a C₈-C₃₀ alkyl or alkenyl, preferably C₁₂-C₂₀ alkyl, more preferably C₁₅-C₁₈ alkyl, or mixtures of such alkyl radicals. Examples of such mixtures are the alkyl radicals obtained from coconut oil, "soft" (non-hardened) tallow, and hardened tallow;
       X is
    Figure imgb0003
       wherein T is O or NR₅, R₅ being H or C₁-C₄ alkyl, preferably H, and R₄ is a divalent C₁-C₃ alkylene group or (C₂H₄O)m, wherein m is a number of from 1 to 8; or X is R₄.
  • Most preferred imidazoline actives of the formula above are of the following formulae :
    Figure imgb0004
       wherein R₁ is a tallow group.
  • Compounds of formula Ia are ditallowimidazolines, while compounds of formula Ib are ditallowimidazoline esters.
  • Quaternized di-long chain imidazoline compounds are of the formula :
    Figure imgb0005
       or mixtures thereof, wherein R and R¹ are, independently, C₁₁-C₂₁ hydrocarbyl groups, preferably tallow, R² is a C₁-C₄ hydrocarbyl group, preferably methyl, A is an anion, m is an integer from 2 to 4, preferably 2 and X is
    Figure imgb0006
    wherein T is O or NR₅, R₅ being H or C₁-C₄ alkyl, preferably H, and R₄ is a divalent C₁-C₃ alkylene group or (C₂H₄O)m, wherein m is a number of from 1 to 8; or X is R₄. Preferably, T is O and R₄ is (CH₂)₂ (quaternized ditallow imidazoline ester).
  • Mono long-chain alkyl amines useful herein include compounds of the formula
    Figure imgb0007
    wherein R₁ is a C₈₋₃₀ acyclic aliphatic , preferably C₁₂₋₂₃ hydrocarbon group which may be intempted by ester linkages, R₂ and R₃ are C₁₋₄ saturated alkyl groups or hydroxyalkyl groups of the formula (CH₂CH₂O)n H where n is an integer from 1 to 5.
  • They further include monotallowimidazolines of the formula (CH₂)m
    Figure imgb0008
    wherein R₁ is a C₈₋₃₀ alkyl or alkyl group, preferably C₁₂₋₂₀, more preferably C₁₅₋₁₈; m is an integer from 2 to 4, preferably 2 and X is
    Figure imgb0009
       wherein T is O or NR₅, R₅ being H or C₁-C₄ alkyl, preferably H, and R₄ is a divalent C₁-C₃ alkylene group or (C₂H₄O)m, wherein m is a number of from 1 to 8; or X is R₄.
  • Mono alkyl quaternary ammonium compounds useful herein include compounds of the formula
    Figure imgb0010
    wherein R₁ is an acyclic aliphatic C₈₋₃₀, preferably C₁₂₋₂₃ hydrocarbon group which may be interupted by ester linkages, R₂, R₃ and R₄ are C₁₋₄ saturated alkyl groups or hydroxyalkyl groups; and A is an anion.
  • A preferred mono-alkyl ammonium compound for use herein is cetyl trimethylammonium bromide.
  • The mono long-chain alkyl amines and mono long-chain alkyl ammonium compounds are preferably used in combination with the di-long chain alkyl ammonium or imidazolines described hereinabove.
  • Most preferred softening actives for use in the additives herein are ditallowdimethyl ammonium, ditallowimidazoline ester, quaternized ditallowimidazoline ester, and mixtures thereof.
    • Optional ingredients
  • The present additives may contain additional ingredients, which can be pre-mixed with the perfume and softening active before they are adsorbed onto the porous silicate, or added, after the adsorption is completed, to the particles.
  • Ingredients which can be pre-mixed with the perfume and softening active are selected from the group of
    • sythetic and natural waxes
    • synthetic and natural fats
    • synthetic and natural mono, di and tri esters of polyols with C₈-C₂₂ carboxylic acids or mixtures thereof
    • C₈₋₂₂ alcohols, ethoxylates thereof and esters thereof with C₁₋₄ carboxylic acids
    • dyes
  • Ingredients which can be added to the particles after adsorption is complete include water-soluble coating materials/agglomerating materials and dyes
  • Preferred ingredients to be pre-mixed are the esters of C8-20 alcohols, in particular glyceryl monostearate.
  • The water-soluble coating/agglomerating materials can be selected from the group of polyvinyl alcohol, polyethylene glycol, sugars, polyacrylamides, polysaccharides and similar natural and synthetic polymers.
  • Dyes are typically used and can be added to the mix before adsorption onto silica, or sprayed on the formed particles as a last step.
    • Method of preparation of the additives herein
  • A co-melt of the softening active and the perfume is typically made, possibly including an optional ingredient such as listed above.
  • The co-melt is adsorbed on porous silica, keeping the temperature, needed to keep the co-melt liquid, typically at 50°C; Adsorption can be achieved by adding the co-melt in portions to the pre-heated porous silica under agitation, or by spraying it on pre-heated porous silica in a "Nauta" type mixer.
  • The resulting free-flowing powder is cooled to a temperature ranging from 3°C to ambient, and sieved on an appropriate sieve (e.g. Mesh 22); the powder is then agglomerated in an agglomeration unit, such as a Plough Share Lödige, possibly with the addition of a coating/agglomeration material; the agglomerate is cooled and sieved over an appropriate sieve (e.g. Mesh 22).
    • Use of the perfume additives herein
  • The perfume additives herein can either be used as single-dose additives for fabric softening compositions, during use, or as additives in the preparation of fabric-softening compositions out of concentrates, before use.
  • Preferably, the present additives are used as single-dose additives to unperfumed fabric softening compositions during use; i.e. a dose of additive sufficient for a typical washing machine load is added to unperfumed fabric softening composition, prior to the rinse cycle of the laundry process.
  • Such an addition can conveniently be made in the dispenser of automatic washing machines; i.e. before starting the laundry cycle, an amount of fabric softening composition in liquid form is first poured into the dispenser of the washing machine, and the specific dose of perfume additive in granular form is added to said fabric softening composition sitting in the dispenser, and is dispersed therein.
  • The resulting mixture is then brought into contact with the fabrics, during the rinse cycle and the perfume is released onto the fabrics.
  • The use of the perfume additives herein is not limited to liquid fabric softening compositions since their granular form would render them quite suitable for use in combination with fabric-softening compositions in particulate form; such fabric-softening compositions can be used as is, or diluted with water before use.
  • When used as such single-wash doses, the present additives can conveniently be packaged into single-dose sachets containing the powdered additive, such sachets being made available to the consumer in the form of boxes containing several of them, said sachets containing either the same perfume, or different perfumes so as to allow the consumer to choose the perfume to be left on the laundered fabrics, for each laundry cycle.
  • The following examples illustrate the invention and facilitate the understanding.
  • The following granulates are prepared, according to the method described above (with cooling temperature of 4°C).
    Ingredients Percentage by weight
    Ex.I Ex.II Ex.III Ex.IV Ex.V Ex.VI Ex.VII Ex.VIII Ex.IX
    Perfume 13% 47% 20% 20% 20% 30% 20% 20% 15%
    Dittalow Dimethyl ammonium 54% 20% 15% 24% - - - - -
    chloride
    Dittalow Imidazoline ester - - - - 47% 30% 27% - -
    CTAB (Cetyl Trimethyl Ammonium Bromide - - - - - - - 14% 10%
    Glyceryl monostearate* - - 10% 23% - - - - -
    Sorbitan distearate* - - - - - - - - 25%
    Silica SipernatR50 33% 33% 40% 33% 33% - - 34% -
    Silica SipernatR22 - - - - - 40% 33% - 50%
    Polyethylene glycol 4000** - - 15% - - - 20% - -
    TO₈ (Tallowalcohol 8 times ethoxylated)* - - - - - - - 32% -
    * added in the pre-mix
    ** sprayed onto formed particles
  • Dye is sprayed onto the above granulates; the formed granulates are used as perfume additives for fabric softening compositions.

Claims (9)

  1. A perfume additive in granular form for use with fabric-softening compositions, containing :
    - from 30% to 80% by weight of a mixture of perfume and softening active, in a ratio of perfume to softening active of 1:10 to 5:1
    - from 20% to 70% by weight of porous silica on which said mixture of perfume and softening active are adsorbed, the particle size of the porous silica not exceeding 500 micrometers.
  2. A perfume additive according to claim 1, wherein the softening active is selected from the group of di-long chain quaternary ammonium compounds, di-long chain imidazoline compounds, di-long chain quaternized imidazoline compounds, mono long chain amines, mono long chain quaternary ammonium compounds, and mixtures thereof.
  3. A perfume additive according to claim 2 wherein the softening active is selected from ditallowdimethylammonium, ditallowimidazoline, ditallowimidazoline ester, quaternized ditallow imidazoline ester, and mixtures thereof.
  4. A perfume additive according to claims 1-3 wherein the weight ratio of perfume to softening active is from 1:5 to 3:1.
  5. A perfume additive according to claims 1-4 which, in addition contains an ingredient selected from the group of:
    - sythetic and natural waxes
    - synthetic and natural fats
    - synthetic and natural mono, di and tri esters of polyols with C₈-C₂₂ carboxylic acids
    - C₈₋₂₂ alcohols, ethoxylates thereof and esters thereof with C₁₋₄ carboxylic acids
    - water-soluble coating or agglomeration materials
    - dyes
  6. A perfume additive according to claim 5 wherein the water-soluble coating material is selected from the group of polyvinyl alcohol, polyethylene oxide/PEG, sugars, polyacrylamides, polysaccharides or similar synthetic or natural polymers.
  7. A perfume additive according to claims 1-5 which contains perfume, softening active, a polyethylene glycol, and a dye.
  8. Use of a perfume additive according to claims 1-6 as a single-dose additive to a quantity of unperfumed fabric-softening composition useful for one laundry cycle of an automatic washing machine.
  9. Use of a perfume additive according to claims 1-6 in the preparation of a fabric-softening composition ready for use, out of a concentrated composition.
EP91201887A 1991-07-18 1991-07-18 Perfume additives for fabric-softening compositions Withdrawn EP0523287A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP91201887A EP0523287A1 (en) 1991-07-18 1991-07-18 Perfume additives for fabric-softening compositions
PCT/US1992/005686 WO1993001794A1 (en) 1991-07-18 1992-07-10 Perfume additives for fabric-softening compositions
CA 2113613 CA2113613C (en) 1991-07-18 1992-07-10 Perfume additives for fabric-softening compositions
JP5502838A JPH06509611A (en) 1991-07-18 1992-07-10 Flavor additives for textile softening compositions
IE922340A IE922340A1 (en) 1991-07-18 1992-07-17 Perfume additives for fabric softening compositions
MX9204224A MX9204224A (en) 1991-07-18 1992-07-17 PERFUME ADDITIVES FOR SOFTENING COMPOSITIONS OF FABRICS.
PT10070692A PT100706A (en) 1991-07-18 1992-07-17 PERFUMED ADDITIVES USED IN FABRIC TYPICAL COMPOSITIONS, CONTAINING A MIXTURE OF PERFUME AND ACTIVE SUBSTANCE OF ADSORVATED YIELD IN SILICA POROSA

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP91201887A EP0523287A1 (en) 1991-07-18 1991-07-18 Perfume additives for fabric-softening compositions

Publications (1)

Publication Number Publication Date
EP0523287A1 true EP0523287A1 (en) 1993-01-20

Family

ID=8207791

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91201887A Withdrawn EP0523287A1 (en) 1991-07-18 1991-07-18 Perfume additives for fabric-softening compositions

Country Status (7)

Country Link
EP (1) EP0523287A1 (en)
JP (1) JPH06509611A (en)
CA (1) CA2113613C (en)
IE (1) IE922340A1 (en)
MX (1) MX9204224A (en)
PT (1) PT100706A (en)
WO (1) WO1993001794A1 (en)

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EP0622453A1 (en) * 1993-04-26 1994-11-02 Setric International S.A. Process for particulate protection of a combustible product against the action of a chlorinated product mixed therewith
WO1995030733A1 (en) * 1994-05-09 1995-11-16 Unilever N.V. Bleach catalyst composition
US5536421A (en) * 1992-09-28 1996-07-16 The Procter & Gamble Company Method for using solid particulate fabric softener in automatic dosing dispenser
US5545350A (en) * 1992-05-12 1996-08-13 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
EP0760243A1 (en) * 1995-08-31 1997-03-05 The Procter & Gamble Company Use of allylic alcohol perfumes as a malodour reduction agent
WO1997011151A1 (en) * 1995-09-18 1997-03-27 The Procter & Gamble Company Delivery systems
WO1997047720A2 (en) * 1996-06-11 1997-12-18 The Procter & Gamble Company Process for producing a particulate laundry additive for perfume delivery having improved physical properties
EP0816484A2 (en) * 1996-06-24 1998-01-07 Givaudan-Roure (International) S.A. Perfume delivery system
WO1998041607A1 (en) * 1997-03-15 1998-09-24 The Procter & Gamble Company Delivery systems
EP0881279A2 (en) * 1997-05-26 1998-12-02 Henkel Kommanditgesellschaft auf Aktien Process for making granules containing cationic surfactant
WO2001005926A1 (en) * 1999-07-20 2001-01-25 The Procter & Gamble Company Improved encapsulated oil particles
WO2002090479A1 (en) * 2001-05-04 2002-11-14 The Procter & Gamble Company Perfumed particles and articles containing the same
EP1471137A1 (en) * 2003-04-23 2004-10-27 The Procter & Gamble Company A composition comprising a surface deposition enhacing cationic polymer
DE102004020400A1 (en) * 2004-04-23 2005-11-17 Henkel Kgaa Perfumed solids
WO2006024415A1 (en) * 2004-09-02 2006-03-09 Henkel Kommanditgesellschaft Auf Aktien Liquids manufactured in solid form for use in particle-shaped detergents and cleansers
WO2009087033A1 (en) * 2008-01-10 2009-07-16 Unilever Plc Granules
GB2507750A (en) * 2012-11-07 2014-05-14 Intelligent Fabric Technologies Plc Fabric softener with colloidal silica for imparting stain resistant properties
US8927026B2 (en) 2011-04-07 2015-01-06 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US8980292B2 (en) 2011-04-07 2015-03-17 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles
WO2019034264A1 (en) * 2017-08-18 2019-02-21 Symrise Ag Fragrance release composition
EP3663385A1 (en) * 2018-12-04 2020-06-10 The Procter & Gamble Company Particulate laundry softening wash additive
WO2020249707A1 (en) * 2019-06-13 2020-12-17 Henkel Ag & Co. Kgaa Granular detergent-, cleaning agent- or treatment agent additive
US11186803B2 (en) 2018-12-04 2021-11-30 The Procter & Gamble Company Particulate laundry softening wash additive

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CN101124310A (en) * 2004-12-21 2008-02-13 德古萨有限责任公司 Perfume delivery system
GB0520900D0 (en) 2005-10-14 2005-11-23 Brightwater Engineering Ltd Method and system

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EP0397245A2 (en) * 1989-05-11 1990-11-14 The Procter & Gamble Company Perfume particles for use in cleaning and conditioning compositions

Cited By (42)

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Publication number Priority date Publication date Assignee Title
US5545350A (en) * 1992-05-12 1996-08-13 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
US5792219A (en) * 1992-09-28 1998-08-11 The Procter & Gamble Company Method for using solid particulate fabric softener in automatic dosing dispenser
US5536421A (en) * 1992-09-28 1996-07-16 The Procter & Gamble Company Method for using solid particulate fabric softener in automatic dosing dispenser
EP0622453A1 (en) * 1993-04-26 1994-11-02 Setric International S.A. Process for particulate protection of a combustible product against the action of a chlorinated product mixed therewith
WO1995030733A1 (en) * 1994-05-09 1995-11-16 Unilever N.V. Bleach catalyst composition
EP0760243A1 (en) * 1995-08-31 1997-03-05 The Procter & Gamble Company Use of allylic alcohol perfumes as a malodour reduction agent
EP1160311A2 (en) * 1995-09-18 2001-12-05 The Procter & Gamble Company Perfume delivery system
WO1997011151A1 (en) * 1995-09-18 1997-03-27 The Procter & Gamble Company Delivery systems
EP1160311A3 (en) * 1995-09-18 2002-03-20 The Procter & Gamble Company Perfume delivery system
WO1997047720A3 (en) * 1996-06-11 1998-03-05 Procter & Gamble Process for producing a particulate laundry additive for perfume delivery having improved physical properties
WO1997047720A2 (en) * 1996-06-11 1997-12-18 The Procter & Gamble Company Process for producing a particulate laundry additive for perfume delivery having improved physical properties
EP0816484A2 (en) * 1996-06-24 1998-01-07 Givaudan-Roure (International) S.A. Perfume delivery system
EP0816484A3 (en) * 1996-06-24 1999-01-27 Givaudan-Roure (International) S.A. Perfume delivery system
WO1998041607A1 (en) * 1997-03-15 1998-09-24 The Procter & Gamble Company Delivery systems
EP0881279A3 (en) * 1997-05-26 1999-06-16 Henkel Kommanditgesellschaft auf Aktien Process for making granules containing cationic surfactant
EP0881279A2 (en) * 1997-05-26 1998-12-02 Henkel Kommanditgesellschaft auf Aktien Process for making granules containing cationic surfactant
WO2001005926A1 (en) * 1999-07-20 2001-01-25 The Procter & Gamble Company Improved encapsulated oil particles
US6608017B1 (en) 1999-07-20 2003-08-19 Procter & Gamble Company Encapsulated oil particles
WO2002090479A1 (en) * 2001-05-04 2002-11-14 The Procter & Gamble Company Perfumed particles and articles containing the same
EP1471137A1 (en) * 2003-04-23 2004-10-27 The Procter & Gamble Company A composition comprising a surface deposition enhacing cationic polymer
DE102004020400A1 (en) * 2004-04-23 2005-11-17 Henkel Kgaa Perfumed solids
WO2006024415A1 (en) * 2004-09-02 2006-03-09 Henkel Kommanditgesellschaft Auf Aktien Liquids manufactured in solid form for use in particle-shaped detergents and cleansers
WO2009087033A1 (en) * 2008-01-10 2009-07-16 Unilever Plc Granules
CN101910396B (en) * 2008-01-10 2012-10-17 荷兰联合利华有限公司 Granules
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US11096875B2 (en) 2010-04-28 2021-08-24 The Procter & Gamble Company Delivery particle
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US10143632B2 (en) 2011-04-07 2018-12-04 The Procter And Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US9561169B2 (en) 2011-04-07 2017-02-07 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US8980292B2 (en) 2011-04-07 2015-03-17 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US8927026B2 (en) 2011-04-07 2015-01-06 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
GB2507750A (en) * 2012-11-07 2014-05-14 Intelligent Fabric Technologies Plc Fabric softener with colloidal silica for imparting stain resistant properties
WO2019034264A1 (en) * 2017-08-18 2019-02-21 Symrise Ag Fragrance release composition
CN110997892A (en) * 2017-08-18 2020-04-10 西姆莱斯有限公司 Fragrance delivery composition
EP3663385A1 (en) * 2018-12-04 2020-06-10 The Procter & Gamble Company Particulate laundry softening wash additive
CN112955530A (en) * 2018-12-04 2021-06-11 宝洁公司 Granular laundry softening detergent additive
WO2020117644A1 (en) * 2018-12-04 2020-06-11 The Procter & Gamble Company Particulate laundry softening wash additive
US11186803B2 (en) 2018-12-04 2021-11-30 The Procter & Gamble Company Particulate laundry softening wash additive
US11193091B2 (en) 2018-12-04 2021-12-07 The Procter & Gamble Company Particulate laundry softening wash additive
US11708545B2 (en) 2018-12-04 2023-07-25 The Procter & Gamble Company Particulate laundry softening wash additive comprising a quat and nonionic surfactant carrier
WO2020249707A1 (en) * 2019-06-13 2020-12-17 Henkel Ag & Co. Kgaa Granular detergent-, cleaning agent- or treatment agent additive

Also Published As

Publication number Publication date
IE922340A1 (en) 1993-01-27
WO1993001794A1 (en) 1993-02-04
PT100706A (en) 1993-08-31
CA2113613C (en) 1998-05-05
JPH06509611A (en) 1994-10-27
MX9204224A (en) 1993-04-01
CA2113613A1 (en) 1993-02-04

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