US20050261134A1 - Aqueous compositions comprising vesicles having certain vesicle permeability - Google Patents
Aqueous compositions comprising vesicles having certain vesicle permeability Download PDFInfo
- Publication number
- US20050261134A1 US20050261134A1 US10/967,758 US96775804A US2005261134A1 US 20050261134 A1 US20050261134 A1 US 20050261134A1 US 96775804 A US96775804 A US 96775804A US 2005261134 A1 US2005261134 A1 US 2005261134A1
- Authority
- US
- United States
- Prior art keywords
- composition
- water
- ethyl
- quaternary ammonium
- active material
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 114
- 230000035699 permeability Effects 0.000 title claims abstract description 18
- 239000011149 active material Substances 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
- -1 hydroxypropyl Chemical group 0.000 claims abstract description 10
- 150000001450 anions Chemical class 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- 239000002304 perfume Substances 0.000 claims description 15
- 239000004744 fabric Substances 0.000 claims description 11
- 229920000858 Cyclodextrin Polymers 0.000 claims description 10
- 239000003139 biocide Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 230000007704 transition Effects 0.000 claims description 5
- QTJISTOHDJAKOQ-UHFFFAOYSA-N 2-hydroxyethylazanium;methyl sulfate Chemical compound [NH3+]CCO.COS([O-])(=O)=O QTJISTOHDJAKOQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940097362 cyclodextrins Drugs 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 3
- 230000003750 conditioning effect Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003337 fertilizer Substances 0.000 claims description 3
- UMKXBPIKICNFME-UHFFFAOYSA-M dimethyl-(2-octadecanoyloxyethyl)-octadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCOC(=O)CCCCCCCCCCCCCCCCC UMKXBPIKICNFME-UHFFFAOYSA-M 0.000 claims description 2
- NUCJYHHDSCEKQN-UHFFFAOYSA-M dimethyl-bis(2-octadecanoyloxyethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(=O)OCC[N+](C)(C)CCOC(=O)CCCCCCCCCCCCCCCCC NUCJYHHDSCEKQN-UHFFFAOYSA-M 0.000 claims description 2
- 239000012872 agrochemical composition Substances 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 238000009792 diffusion process Methods 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 5
- 0 C.[4*]C(=O)OC.[4*]OC(C)=O Chemical compound C.[4*]C(=O)OC.[4*]OC(C)=O 0.000 description 5
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 5
- 238000000638 solvent extraction Methods 0.000 description 5
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004900 laundering Methods 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 229940067107 phenylethyl alcohol Drugs 0.000 description 3
- 238000001472 pulsed field gradient Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000001116 FEMA 4028 Substances 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 2
- 229960004853 betadex Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930002839 ionone Natural products 0.000 description 2
- 150000002499 ionone derivatives Chemical class 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000244 nuclear magnetic resonance diffusometry Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 229930007090 gamma-ionone Natural products 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000007431 microscopic evaluation Methods 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- SFEOKXHPFMOVRM-BQYQJAHWSA-N γ-ionone Chemical compound CC(=O)\C=C\C1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-BQYQJAHWSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/14—Liposomes; Vesicles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- 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
- 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
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
Definitions
- the present invention relates to aqueous compositions comprising vesicles having a vesicle permeability index of less than about 1.3 to facilitate the delivery of water-soluble active materials having a C log P of less than about 2.0 to surfaces being treated with the compositions.
- a number of commercialized products such as fabric softeners, hard surface cleaners, hair conditioners, agrochemical products and paints, contain active materials that are water-soluble. Oftentimes, these products contain water-soluble active materials that are intended to be deposited onto a surface being treated with the product. However, if these water-soluble materials are in a highly aqueous environment, it can be difficult to effectively deposit the water-soluble active materials onto the surface.
- a fabric softening composition is typically added to the rinse solution in a fabric laundering process, which contains a large volume of water. Once the rinse cycle is complete, the rinse solution is discarded down the drain, usually taking a large portion of the water-soluble active materials with it. Thus only a small portion of the water-soluble active materials is actually deposited on the treated fabrics.
- composition containing water-soluble active materials such that the composition can effectively deposit the water-soluble active materials to a surface being treated with the composition.
- compositions comprising:
- the present invention further relates to a process for making the present compositions comprising the steps of dispersing the dialkyl quaternary ammonium compound and the water-soluble active material in an aqueous solution to form vesicles having a vesicle permeability index of less than about 1.3.
- the present invention relates to compositions containing vesicles to facilitate the delivery of water-soluble active materials to surfaces treated with the present compositions.
- vesicle means one or more bilayers arranged in a closed, usually spherical geometry, said bilayer comprises quaternary ammonium agent as described hereinabove.
- the vesicles are preferably substantially spherical.
- the presence of vesicles in the present compositions can be detected by microscopic analysis (e.g., polarised light microscopy at a magnification of 60 ⁇ ).
- the vesicles in the present compositions have a number average size of from about 50 nm to about 20 ⁇ m, more preferably from about 100 nm to about 5 ⁇ m, most preferably from about 200 nm to about 2 ⁇ m as determined by photon correlation spectroscopy.
- the vesicles in the present compositions are generally formed by dispersing the molten dialkyl quaternary ammonium compound in hot water having a temperature above the transition temperature of the dialkyl quaternary ammonium compound. It is believed that the vesicles envelope the water-soluble active materials and then can effectively deliver these species to a surface being treated.
- the vesicles in the present compositions exhibit a particular vesicle permeability as measured according to the test method described herein.
- the vesicle permeability of the vesicles formed can be affected by the temperature and by the structure of the dialkyl quaternary ammonium compounds, more specifically by the degree of unsaturation and the presence or the absence of linking groups between the alkyl chain and the nitrogen, such as esters.
- compositions of the present invention will typically have a pH of from about 2 to about 7, preferably from about 2 to about 6, and more preferably from about 2.5 to about 5.0.
- compositions comprise a dialkyl quaternary ammonium compound having the formula: wherein R 1 and R 2 are independently C 12 to C 20 saturated alkyl chains; Y is wherein R 4 is ethyl or isopropyl; R 3 and R 5 are independently methyl, ethyl, hydroxyethyl, or hydroxypropyl; m is 1, 2, or 3; n is 1 or 2; and p is 0 or 1.
- the counterion, X ⁇ in the above compounds can be any compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and the like, more preferably chloride or methyl sulfate.
- a strong acid for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and the like, more preferably chloride or methyl sulfate.
- Suitable dialkyl quaternary ammonium compounds of the present invention include alkylchains wherein R 1 and R 2 are C 16 or C 18 or hardened tallow or hardened palm or mixtures thereof.
- Non-limiting examples of dialkyl quaternary ammonium compounds include N,N-di(stearoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride; N-stearyl-N-(stearoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride; N,N-di(stearoyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium methylsulfate; and 1,2-distearoyloxy-3-N,N,N-trimethylammoniumpropane chloride.
- the dialkyl quaternary ammonium compound is typically present in the compositions of the invention at a level of from about 1% to about 30%, preferably from about 2% to about 25%, and more preferably from about 3% to about 20%, by weight of the composition.
- the present compositions further comprise a water-soluble active material.
- the degree of hydrophilicity of an active material in the present compositions can be correlated with its octanol/water partitioning coefficient P.
- the octanol/water partitioning coefficient of an active material is the ratio between its equilibrium concentration in octanol and in water.
- An active material with a greater partitioning coefficient P is more hydrophobic.
- an active material with a smaller partitioning coefficient P is more hydrophilic. Since the partitioning coefficients of active materials normally have high values, they are more conveniently given in the form of their logarithm to the base 10, log P.
- the log P of many materials has been reported; for example, the Pomona 92 database, available from Daylight Chemical Information Systems, Inc. (Daylog CIS), Irvine, Calif., contains many, along with citations to the original literature. However, the log P values are most conveniently calculated by the “C log P” program (calculation of hydrophobicities as log P (oil/water)) version 4.01, available from Daylight Chemical Information Systems Inc of Irvine Calif., USA.
- the C log P values which are the most reliable and widely used estimates for this physicochemical property, are used instead of the experimental log P values in the selection of water-soluble active materials which are useful in the present invention.
- the water-soluble active materials in the present compositions have a C log P of less than about 2.0, more preferably less than about 1.0.
- water-soluble active materials include perfume raw materials (“PRMs”), cyclodextrins, biocides, fertilizers, drugs, and the like.
- PRMs perfume raw materials
- Non-limiting examples of water-soluble perfume raw materials include beta gamma hexenol, coumarin, ethyl acetoacetate, and a mixture of 2 parts benzaldehyde, 2 parts beta gamma hexenol, 10 parts coumarin, 10 parts ethyl acetoacetate and 40 parts phenyl ethyl alcohol.
- Non-limiting examples of water-soluble cyclodextrins include hydroxypropyl beta-cyclodextrin.
- Non-limiting examples of water-soluble biocides include dodecyl trimethyl ammonium chloride, glutaraldehyde, and KATHON®.
- the water-soluble active material is typically present in the compositions of the present invention at a level of from about 0.01% to about 10%, preferably from about 0.05% to about 5%, and more preferably from about 0.1% to about 2%, by weight of the composition.
- compositions are free of humectants, such as those described in WO 98/22085, WO 98/18444 and WO 97/01326, and/or emollients, such as those described in Sagarin, Cosmetics, Science and Technology, 2 nd Edition, Vol. 1, pp. 32-43 (1972).
- humectants such as those described in WO 98/22085, WO 98/18444 and WO 97/01326, and/or emollients, such as those described in Sagarin, Cosmetics, Science and Technology, 2 nd Edition, Vol. 1, pp. 32-43 (1972).
- compositions further comprise water, typically at a level of from about 60% to about 99%, preferably from about 70% to about 97%, and more preferably from about 75% to about 97%, by weight of the composition.
- the present compositions can optionally further comprise a number of various adjunct ingredients, depending on the type and use for the composition.
- the present compositions include fabric softening compositions for imparting softness and freshness (perfumes) to fabrics during a laundering process. Such compositions are typically added to the rinse cycle of a laundering process, although certain compositions can also be added during a wash cycle.
- Typical adjunct ingredients of fabric softening compositions are described in, e.g., U.S. Pat. No. 5,574,179; U.S. Pat. No. 5,562,849; U.S. Pat. No. 5,545,350; U.S. Pat. No. 5,545,340; U.S. Pat. No. 4,981,239; U.S. Pat. No. 4,767,547; U.S. Pat. No. 4,550,862; and U.S. Pat. No. 4,424,134.
- compositions can also include hard surface cleaning compositions, such as for delivering water-soluble biocides or perfume materials to the surface being cleaned.
- hard surface cleaning compositions such as for delivering water-soluble biocides or perfume materials to the surface being cleaned.
- Typical adjunct ingredients of hard surface cleaning compositions are described in, e.g., U.S. Pat. No. 5,382,376 and U.S. Pat. No. 4,111,854.
- the present compositions can also include hair conditioning compositions, such as for delivering water-soluble perfume raw materials or cyclodextrins to the hair being treated.
- hair conditioning compositions such as for delivering water-soluble perfume raw materials or cyclodextrins to the hair being treated.
- Typical adjunct ingredients of hair conditioning compositions are described in, e.g., U.S. Pat. No.6,589,517; U.S. Pat. No. 6,468,515; and U.S. Pat. No. 5,876,705.
- compositions can also include agrochemical compositions such as for targeted delivery of water-soluble biocides, fertilizer, or drugs to plant leaves and soil.
- agrochemical compositions such as for targeted delivery of water-soluble biocides, fertilizer, or drugs to plant leaves and soil.
- Typical adjunct ingredients of agrochemical compositions are described in, e.g., U.S. Pat. No. 6,200,586; US 2003/0013799A1; and Pesticide Formulation and Adjuvant Technology , Edited by Chester L. Foy and David W Pitchard, 1996, CRC Press Inc.
- the present compositions can include paint compositions such as for delivery and adhesion of water-soluble biocides to the surfaces being painted, such as boat hulls.
- Typical adjunct ingredients of paint compositions are described in, e.g., U.S. Pat. No. 6,479,566; U.S. Pat. No. 6,242,526; WO 96/41842; and WO 97/00919.
- the vesicular compositions of the present invention are made by dispersing a molten dialkyl quaternary ammonium compound in water having a temperature above the transition temperature of the dialkyl quaternary ammonium compound under mechanical shear.
- the water temperature is kept above the transition temperature during the dispersion process to ensure the formation of a vesicular dispersion of the dialkyl quaternary ammonium compound.
- the water-soluble active material to be delivered to the treated surface is preferably added to the hot water prior to the addition of the molten dialkyl quaternary ammonium compound.
- the water-soluble active material is added together with or after the addition of the dialkyl quaternary ammonium compound to the hot dispersion, and the dispersion is kept hot for a sufficient time under mechanical shear to ensure the water-soluble active material is partioned into the intravesicular water domain.
- the vesicular dispersion is subsequently cooled to ambient temperature, thus ensuring effective encapsulation of the water-soluble active material in the vesicles.
- a NMR diffusometry method provides information about the distances diffused by species in a component resolved manner.
- the method allows for determination of the diffusion rates of all components in the mixture. Due to the very high signal-to-noise of water, water is used to act as the probe for the permeability though the vesicle membranes.
- the component resolved signal decay in the NMR diffusometry experiment is impacted by the presence of barriers. In a concentrated mixture of vesicles the signal contains, roughly, two different types of water; water trapped inside and water outside the vesicles. Due to the chemical exchange, the fraction of water inside or outside depends strongly on the allowed diffusion time.
- the ratio of the apparent volume fraction inside vesicles at a shorter diffusion time (e.g. 10 ms) over the apparent volume fraction at a longer diffusion time (e.g. 80 ms) gives therefore a measure of the vesicle permeability.
- the vesicles in the present compositions have a particular permeability index, P, that is determined according to the following test method.
- Water diffusion inside and outside the vesicles is measured with Pulsed Field Gradient (“PFG”) NMR and evaluated according to the methods described in “Colloids and Surfaces A, Diffusion of water in multilamellar vesicles of dialkyl and dialkyl ester ammonium surfactants”, Cecilia Groth, Johanna Bender and Magnus Nydén (in press). Diffusion measurements are performed at 20° C. Diffusion times range from 10 ms up to 1 s using 5 different values logarithmically spaced between 10 and 80 ms.
- the pulsed field gradient strength is varied between 0.005 to 3.74 T/m with 45 linearly spaced gradient strengths spaced in-between (47 in total).
- the permeability Index, P can then be calculated as P vw app (10 ms)/P vw app (80 ms).
- compositions of the present invention are provided in the following table as Examples 1-11.
- the compositions can be used as fabric softening compositions added during the rinse cycle of a laundering process to improve the softness and freshness of the fabrics being laundered.
- PRM1 beta gamma hexenol
- PRM2 coumarin
- PRM3 ethyl acetoacetate
- PRM4 2 parts benzaldehyde, 2 parts beta gamma hexenol, 10 parts coumarin, 10 parts ethyl acetoacetate and 40 parts phenyl ethyl alcohol.
- composition of Example 11 is a preferred composition of the present invention wherein the composition is made by adding PRM 4 to the hot product during formation of the vesicular dispersion, whereas the compositions of Examples 12 and 13 are made by adding PRM 4 to the cold product after the vesicular dispersion is formed.
- Every maximum numerical limitation given throughout this specification includes every lower numerical limitation, as if such lower numerical limitations were expressly written herein. Every minimum numerical limitation given throughout this specification includes every higher numerical limitation, as if such higher numerical limitations were expressly written herein. Every numerical range given throughout this specification includes every narrower numerical range that falls within such broader numerical range, as if such narrower numerical ranges were all expressly written herein.
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Abstract
Compositions for effectively delivering a water-soluble active material to a surface comprise:
(a) from about 1% to about 30%, by weight of the composition, of a dialkyl quaternary ammonium compound having the formula:
wherein R1 and R2 are independently C12 to C20 saturated alkyl chains; Y is
wherein R4 is ethyl or isopropyl; R3 and R5 are independently methyl, ethyl, hydroxyethyl, or hydroxypropyl; m is 1, 2, or 3; n is 1 or 2; p is 0 or 1; and X− is a suitable anion; (b) from about 0.01% to about 10%, by weight of the composition, of water-soluble active material having a C log P of less than about 2.0; and (c) at least about 60%, by weight of the composition, of water; wherein the compositions contain vesicles having a vesicle permeability index of less than about 1.3. Processes to make the compositions comprise the steps of dispersing the dialkyl quaternary ammonium compound and the water-soluble active material in an aqueous solution to form vesicles having a vesicle permeability index of less than about 1.3.
(a) from about 1% to about 30%, by weight of the composition, of a dialkyl quaternary ammonium compound having the formula:
wherein R1 and R2 are independently C12 to C20 saturated alkyl chains; Y is
wherein R4 is ethyl or isopropyl; R3 and R5 are independently methyl, ethyl, hydroxyethyl, or hydroxypropyl; m is 1, 2, or 3; n is 1 or 2; p is 0 or 1; and X− is a suitable anion; (b) from about 0.01% to about 10%, by weight of the composition, of water-soluble active material having a C log P of less than about 2.0; and (c) at least about 60%, by weight of the composition, of water; wherein the compositions contain vesicles having a vesicle permeability index of less than about 1.3. Processes to make the compositions comprise the steps of dispersing the dialkyl quaternary ammonium compound and the water-soluble active material in an aqueous solution to form vesicles having a vesicle permeability index of less than about 1.3.
Description
- This application claims priority to U.S. Provisional Application Ser. No. 60/511,732, filed Oct. 16, 2003, the disclosure of which is incorporated by reference herein.
- The present invention relates to aqueous compositions comprising vesicles having a vesicle permeability index of less than about 1.3 to facilitate the delivery of water-soluble active materials having a C log P of less than about 2.0 to surfaces being treated with the compositions.
- A number of commercialized products, such as fabric softeners, hard surface cleaners, hair conditioners, agrochemical products and paints, contain active materials that are water-soluble. Oftentimes, these products contain water-soluble active materials that are intended to be deposited onto a surface being treated with the product. However, if these water-soluble materials are in a highly aqueous environment, it can be difficult to effectively deposit the water-soluble active materials onto the surface. For example, a fabric softening composition is typically added to the rinse solution in a fabric laundering process, which contains a large volume of water. Once the rinse cycle is complete, the rinse solution is discarded down the drain, usually taking a large portion of the water-soluble active materials with it. Thus only a small portion of the water-soluble active materials is actually deposited on the treated fabrics.
- It has thus been desired to develop a composition containing water-soluble active materials such that the composition can effectively deposit the water-soluble active materials to a surface being treated with the composition.
- The present invention relates to compositions comprising:
-
- (a) from about 1% to about 30%, by weight of the composition, of a dialkyl quaternary ammonium compound having the formula:
wherein R1 and R2 are independently C12 to C20 saturated alkyl chains; Y is
wherein R4 is ethyl or isopropyl; R3 and R5 are independently methyl, ethyl, hydroxyethyl, or hydroxypropyl; m is 1, 2, or 3; n is 1 or 2; p is 0 or 1; and X− is a suitable anion; - (b) from about 0.01% to about 10%, by weight of the composition, of water-soluble active material having a C log P of less than about 2.0; and
- (c) at least about 60%, by weight of the composition, of water;
wherein the compositions contain vesicles having a vesicle permeability of less than about 1.3, preferably less than about 1.1, and more preferably less than about 1.0. The fully saturated dialkyl quaternary ammonium compounds of the present compositions, containing at least one ester bond, have been found to form vesicles that can encapsulate water-soluble active materials and that exhibit a low rate of diffusion across the membrane of the vesicles. As the vesicles deposit onto the surfaces being treated with the compositions, the vesicles are able to effectively deliver water-soluble active materials to the surface, which previously has been difficult to achieve.
- (a) from about 1% to about 30%, by weight of the composition, of a dialkyl quaternary ammonium compound having the formula:
- The present invention further relates to a process for making the present compositions comprising the steps of dispersing the dialkyl quaternary ammonium compound and the water-soluble active material in an aqueous solution to form vesicles having a vesicle permeability index of less than about 1.3.
- Vesicular Compositions
- The present invention relates to compositions containing vesicles to facilitate the delivery of water-soluble active materials to surfaces treated with the present compositions. As used herein the term “vesicle” means one or more bilayers arranged in a closed, usually spherical geometry, said bilayer comprises quaternary ammonium agent as described hereinabove. In the compositions herein, the vesicles are preferably substantially spherical. The presence of vesicles in the present compositions can be detected by microscopic analysis (e.g., polarised light microscopy at a magnification of 60×). Preferably, the vesicles in the present compositions have a number average size of from about 50 nm to about 20 μm, more preferably from about 100 nm to about 5 μm, most preferably from about 200 nm to about 2 μm as determined by photon correlation spectroscopy.
- The vesicles in the present compositions are generally formed by dispersing the molten dialkyl quaternary ammonium compound in hot water having a temperature above the transition temperature of the dialkyl quaternary ammonium compound. It is believed that the vesicles envelope the water-soluble active materials and then can effectively deliver these species to a surface being treated.
- The vesicles in the present compositions exhibit a particular vesicle permeability as measured according to the test method described herein. The vesicle permeability of the vesicles formed can be affected by the temperature and by the structure of the dialkyl quaternary ammonium compounds, more specifically by the degree of unsaturation and the presence or the absence of linking groups between the alkyl chain and the nitrogen, such as esters.
- The compositions of the present invention will typically have a pH of from about 2 to about 7, preferably from about 2 to about 6, and more preferably from about 2.5 to about 5.0.
- Dialkyl Quaternary Ammonium Compound
- The present compositions comprise a dialkyl quaternary ammonium compound having the formula:
wherein R1 and R2 are independently C12 to C20 saturated alkyl chains; Y is
wherein R4 is ethyl or isopropyl; R3 and R5 are independently methyl, ethyl, hydroxyethyl, or hydroxypropyl; m is 1, 2, or 3; n is 1 or 2; and p is 0 or 1. The counterion, X− in the above compounds, can be any compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and the like, more preferably chloride or methyl sulfate. - Suitable dialkyl quaternary ammonium compounds of the present invention include alkylchains wherein R1 and R2 are C16 or C18 or hardened tallow or hardened palm or mixtures thereof. Non-limiting examples of dialkyl quaternary ammonium compounds include N,N-di(stearoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride; N-stearyl-N-(stearoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride; N,N-di(stearoyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium methylsulfate; and 1,2-distearoyloxy-3-N,N,N-trimethylammoniumpropane chloride.
- The dialkyl quaternary ammonium compound is typically present in the compositions of the invention at a level of from about 1% to about 30%, preferably from about 2% to about 25%, and more preferably from about 3% to about 20%, by weight of the composition.
- Water-Soluble Activie Material
- The present compositions further comprise a water-soluble active material. The degree of hydrophilicity of an active material in the present compositions can be correlated with its octanol/water partitioning coefficient P. The octanol/water partitioning coefficient of an active material is the ratio between its equilibrium concentration in octanol and in water. An active material with a greater partitioning coefficient P is more hydrophobic. Conversely, an active material with a smaller partitioning coefficient P is more hydrophilic. Since the partitioning coefficients of active materials normally have high values, they are more conveniently given in the form of their logarithm to the base 10, log P.
- The log P of many materials has been reported; for example, the Pomona 92 database, available from Daylight Chemical Information Systems, Inc. (Daylog CIS), Irvine, Calif., contains many, along with citations to the original literature. However, the log P values are most conveniently calculated by the “C log P” program (calculation of hydrophobicities as log P (oil/water)) version 4.01, available from Daylight Chemical Information Systems Inc of Irvine Calif., USA. The C log P values, which are the most reliable and widely used estimates for this physicochemical property, are used instead of the experimental log P values in the selection of water-soluble active materials which are useful in the present invention.
- The water-soluble active materials in the present compositions have a C log P of less than about 2.0, more preferably less than about 1.0.
- Examples of water-soluble active materials include perfume raw materials (“PRMs”), cyclodextrins, biocides, fertilizers, drugs, and the like. Non-limiting examples of water-soluble perfume raw materials include beta gamma hexenol, coumarin, ethyl acetoacetate, and a mixture of 2 parts benzaldehyde, 2 parts beta gamma hexenol, 10 parts coumarin, 10 parts ethyl acetoacetate and 40 parts phenyl ethyl alcohol. Non-limiting examples of water-soluble cyclodextrins include hydroxypropyl beta-cyclodextrin. Non-limiting examples of water-soluble biocides include dodecyl trimethyl ammonium chloride, glutaraldehyde, and KATHON®.
- The water-soluble active material is typically present in the compositions of the present invention at a level of from about 0.01% to about 10%, preferably from about 0.05% to about 5%, and more preferably from about 0.1% to about 2%, by weight of the composition.
- In one embodiment of the present invention, the compositions are free of humectants, such as those described in WO 98/22085, WO 98/18444 and WO 97/01326, and/or emollients, such as those described in Sagarin, Cosmetics, Science and Technology, 2nd Edition, Vol. 1, pp. 32-43 (1972).
- Water
- The present compositions further comprise water, typically at a level of from about 60% to about 99%, preferably from about 70% to about 97%, and more preferably from about 75% to about 97%, by weight of the composition.
- Adjunct Material
- The present compositions can optionally further comprise a number of various adjunct ingredients, depending on the type and use for the composition. In a preferred embodiment, the present compositions include fabric softening compositions for imparting softness and freshness (perfumes) to fabrics during a laundering process. Such compositions are typically added to the rinse cycle of a laundering process, although certain compositions can also be added during a wash cycle. Typical adjunct ingredients of fabric softening compositions are described in, e.g., U.S. Pat. No. 5,574,179; U.S. Pat. No. 5,562,849; U.S. Pat. No. 5,545,350; U.S. Pat. No. 5,545,340; U.S. Pat. No. 4,981,239; U.S. Pat. No. 4,767,547; U.S. Pat. No. 4,550,862; and U.S. Pat. No. 4,424,134.
- The present compositions can also include hard surface cleaning compositions, such as for delivering water-soluble biocides or perfume materials to the surface being cleaned. Typical adjunct ingredients of hard surface cleaning compositions are described in, e.g., U.S. Pat. No. 5,382,376 and U.S. Pat. No. 4,111,854.
- The present compositions can also include hair conditioning compositions, such as for delivering water-soluble perfume raw materials or cyclodextrins to the hair being treated. Typical adjunct ingredients of hair conditioning compositions are described in, e.g., U.S. Pat. No.6,589,517; U.S. Pat. No. 6,468,515; and U.S. Pat. No. 5,876,705.
- The present compositions can also include agrochemical compositions such as for targeted delivery of water-soluble biocides, fertilizer, or drugs to plant leaves and soil. Typical adjunct ingredients of agrochemical compositions are described in, e.g., U.S. Pat. No. 6,200,586; US 2003/0013799A1; and Pesticide Formulation and Adjuvant Technology, Edited by Chester L. Foy and David W Pitchard, 1996, CRC Press Inc.
- The present compositions can include paint compositions such as for delivery and adhesion of water-soluble biocides to the surfaces being painted, such as boat hulls. Typical adjunct ingredients of paint compositions are described in, e.g., U.S. Pat. No. 6,479,566; U.S. Pat. No. 6,242,526; WO 96/41842; and WO 97/00919.
- Process of Manufacture
- The vesicular compositions of the present invention are made by dispersing a molten dialkyl quaternary ammonium compound in water having a temperature above the transition temperature of the dialkyl quaternary ammonium compound under mechanical shear. The water temperature is kept above the transition temperature during the dispersion process to ensure the formation of a vesicular dispersion of the dialkyl quaternary ammonium compound.
- The water-soluble active material to be delivered to the treated surface is preferably added to the hot water prior to the addition of the molten dialkyl quaternary ammonium compound. In an alternative process, the water-soluble active material is added together with or after the addition of the dialkyl quaternary ammonium compound to the hot dispersion, and the dispersion is kept hot for a sufficient time under mechanical shear to ensure the water-soluble active material is partioned into the intravesicular water domain.
- The vesicular dispersion is subsequently cooled to ambient temperature, thus ensuring effective encapsulation of the water-soluble active material in the vesicles.
- Test Method for Determining the Vesicle Permeability Index
- A NMR diffusometry method provides information about the distances diffused by species in a component resolved manner. In a mixture of molecules, for example with water, surfactant and other solvents forming a vesicle dispersion, the method allows for determination of the diffusion rates of all components in the mixture. Due to the very high signal-to-noise of water, water is used to act as the probe for the permeability though the vesicle membranes. The component resolved signal decay in the NMR diffusometry experiment is impacted by the presence of barriers. In a concentrated mixture of vesicles the signal contains, roughly, two different types of water; water trapped inside and water outside the vesicles. Due to the chemical exchange, the fraction of water inside or outside depends strongly on the allowed diffusion time. Important to know is also that once a molecule from the inside leaves to the outside that water would appear to have belonged to the outside from the beginning. For the water initially outside, the situation is quite opposite. That water appears all the time to belong to the outside. In effect the signal from the water inside will decrease as the allowed diffusion time is made longer while the signal from the outside increases.
- The ratio of the apparent volume fraction inside vesicles at a shorter diffusion time (e.g. 10 ms) over the apparent volume fraction at a longer diffusion time (e.g. 80 ms) gives therefore a measure of the vesicle permeability.
- The vesicles in the present compositions have a particular permeability index, P, that is determined according to the following test method. Water diffusion inside and outside the vesicles is measured with Pulsed Field Gradient (“PFG”) NMR and evaluated according to the methods described in “Colloids and Surfaces A, Diffusion of water in multilamellar vesicles of dialkyl and dialkyl ester ammonium surfactants”, Cecilia Groth, Johanna Bender and Magnus Nydén (in press). Diffusion measurements are performed at 20° C. Diffusion times range from 10 ms up to 1 s using 5 different values logarithmically spaced between 10 and 80 ms. The pulsed field gradient strength is varied between 0.005 to 3.74 T/m with 45 linearly spaced gradient strengths spaced in-between (47 in total). The basic Hahn-echo sequence is used with δ=4 ms and with varying diffusion times Δ=10, 20, 40 and 80 and for Δ=1000 ms the stimulated echo-sequence is used.
- From fitted values of the echo decay the apparent fraction of water in the vesicles at a specific diffusion time t can be calculated. The permeability Index, P, can then be calculated as Pvw app(10 ms)/Pvw app(80 ms).
- As a non-limiting example, for a composition comprising HT-DEEDMAC at 20° C. the apparent fraction of water at Δ=10 ms is Pvw app(10 )=0.28 and at Δ=80 ms it is 0.49. The reason for this behavior is, as stated above, due to the finite gradient effect. The permeability index, as defined above then becomes Pvw app(10 ms)/Pvw app(80 ms)=0.28/0.49=0.57. Note that in this case the index is smaller than one due to the effect mentioned above in combination with the very slow water permeation.
- Non-limiting examples of compositions of the present invention are provided in the following table as Examples 1-11. The compositions can be used as fabric softening compositions added during the rinse cycle of a laundering process to improve the softness and freshness of the fabrics being laundered.
Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 HT-DEEDMAC1 5% — — 5% 5% HT-TEAesterquat2 — — 5% — — HT-PDesterquat3 — 5% — — — Hydrochloric acid 0.02% 0.02% 0.02% 0.02% 0.02% Gluteraldehyde 0.05% 0.05% 0.05% 0.05% 0.05% Dye 10 ppm 10 ppm 10 ppm 10 ppm 10 ppm Perfume4 0.3% 0.3% 0.3% 0.17% 0.3% Water Soluble 0.01% 0.05% 0.05% 0.17% — Perfume Material PRM1 PRM2 PRM3 PRM4 Cyclodextrin5 — — — — 0.3% Water Balance Balance Balance Balance Balance Ex. 6 Ex. 7 Ex. 8 Ex. 9 Ex. 10 HT-DEEDMAC1 15% — — 15% 15% HT-TEAesterquat2 — — 15% — — HT-PDesterquat3 — 15% — — — Hydrochloric acid 0.02% 0.02% 0.02% 0.02% 0.02% CaCl2 0.15% 0.15% 0.15% 0.15% 0.15% Dye 10 ppm 10 ppm 10 ppm 10 ppm 10 ppm Perfume4 0.9% 0.9% 0.9% 0.5% 0.9% Water Soluble 0.03% 0.15% 0.15% 0.5% — Perfume Material (PRM1) (PRM2) (PRM3) (PRM4) Cyclodextrin5 — — — — 1.0% Water Balance Balance Balance Balance Balance
1N,N-di(hardened tallowyl-oxy-ethyl)-N,N-dimethyl ammonium chloride.
2N,N-di(hardened tallowoyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium methylsulfate
31,2-dihardenedtallowoyloxy-3-N,N,N-trimethylammoniumpropane chloride
4Water-insoluble perfume.
5Hydroxypropyl beta-cyclodextrin.
PRM1: beta gamma hexenol
PRM2: coumarin
PRM3: ethyl acetoacetate
PRM4: 2 parts benzaldehyde, 2 parts beta gamma hexenol, 10 parts coumarin, 10 parts ethyl acetoacetate and 40 parts phenyl ethyl alcohol.
- In the following table, the composition of Example 11 is a preferred composition of the present invention wherein the composition is made by adding PRM4 to the hot product during formation of the vesicular dispersion, whereas the compositions of Examples 12 and 13 are made by adding PRM4 to the cold product after the vesicular dispersion is formed.
Ex. 11 Ex. 12 Ex. 13 HT-DEEDMAC1 10% 10% — DEEDMAC6 — — 10% Hydrochloric acid 0.02% 0.02% 0.02% CaCl2 — — — Dye — — — Perfume4 0.18% 0.18% Ionone 0.18% Ionone Gamma Ionone Gamma Methyl Gamma Methyl Methyl Water Soluble 0.32% 0.32% 0.32% Perfume Material (PRM4) (PRM4) (PRM4) Cyclodextrin5 — — — Water Balance Balance Balance
1N,N-di(hardened tallowyl-oxy-ethyl)-N,N-dimethyl ammonium chloride.
4Water-insoluble perfume.
5Hydroxypropyl beta-cyclodextrin.
6N,N-di(tallowyl-oxy-ethyl)-N,N-dimethyl ammonium chloride.
PRM4: 2 parts benzaldehyde, 2 parts beta gamma hexenol, 10 parts coumarin, 10 parts ethyl acetoacetate and 40 parts phenyl ethyl alcohol.
- In this example, 2 terry swatches of 40 grams each are rinsed for 5 minutes in 1 liter of tap water containing 2 ml of each of the compositions of Examples 11-13 above, and the terry swatches are subsequently spun dry in a commercial washing machine. The swatches are line dried overnight, and the odor impact of the swatches treated with the composition of Example 11 are compared to swatches treated with the compositions of Example 12 and 13 respectively.
- The table below shows a higher odor impact for the terry swatches treated with the preferred compositions of the invention.
Ex. 11 Ex. 12 Ex. 13 Damp Fabric Odor +4 Ref. — Odor on Dry Fabrics +3 — Ref.
Scale used:
+3 = slightly stronger;
+5 = stronger.
- All documents cited in the Detailed Description of the Invention are, in relevant part, incorporated herein by reference; the citation of any document is not to be construed as an admission that it is prior art with respect to the present invention.
- It should be understood that every maximum numerical limitation given throughout this specification includes every lower numerical limitation, as if such lower numerical limitations were expressly written herein. Every minimum numerical limitation given throughout this specification includes every higher numerical limitation, as if such higher numerical limitations were expressly written herein. Every numerical range given throughout this specification includes every narrower numerical range that falls within such broader numerical range, as if such narrower numerical ranges were all expressly written herein.
- While particular embodiments of the present invention have been illustrated and described, it would be apparent to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.
Claims (17)
1. An aqueous composition comprising:
(a) from about 1% to about 30%, by weight of the composition, of a dialkyl quaternary ammonium compound having the formula:
wherein R1 and R2 are independently C12 to C20 saturated alkyl chains; Y is
wherein R4 is ethyl or isopropyl; R3 and R5 are independently methyl, ethyl, hydroxyethyl, or hydroxypropyl; m is 1, 2, or 3; n is 1 or 2; p is 0 or 1; and X− is an anion;
(b) from about 0.01% to about 10%, by weight of the composition, of water-soluble active material having a C log P of less than about 2.0; and
(c) at least about 60%, by weight of the composition, of water;
wherein the compositions contain vesicles having a vesicle permeability index of less than about 1.3.
2. The composition of claim 2 wherein said vesicle permeability index of said vesicles is less than about 1.1.
3. The composition of claim 3 wherein said vesicle permeability index of said vesicles is less than about 1.0.
4. The composition of claim 1 , wherein the C log P of said water-soluble active material is less than about 1.0.
5. The composition of claim 1 wherein said water-soluble active material is selected from the group consisting of perfume raw materials, cyclodextrins, biocides, fertilizers, drugs, and mixtures thereof.
6. The composition of claim 5 wherein said water-soluble active material is a perfume raw material.
7. The composition of claim 5 wherein said water-soluble active material is a cyclodextrin.
8. The composition of claim 5 wherein said water-soluble active material is a biocide.
9. The composition of claim 1 wherein said dialkyl quaternary ammonium compound is selected from the group consisting of N,N-di(stearoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride; N,N-di(hardenedtallowoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride; N-stearyl-N-(stearoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride; N-hardenedtallowyl-N-(hardenedtallowoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride; N,N-di(stearoyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium methylsulfate; N,N-di(hardenedtallowoyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium methylsulfate; 1,2-distearoyloxy-3-N,N,N-trimethylammoniumpropane chloride and 1,2-hardenedtallowoyloxy-3-N,N,N-trimethylammoniumpropane chloride.
10. The composition of claim 9 wherein said dialkyl quaternary ammonium compound is present at a level of from about 2% to about 25%, by weight of the composition.
11. The composition of claim 10 wherein said dialkyl quaternary ammonium compound is present at a level of from about 3% to about 20%, by weight of the composition.
12. The composition of claim 1 wherein said composition is a fabric softening composition.
13. The composition of claim 1 wherein said composition is a hard surface cleaning composition.
14. The composition of claim 1 wherein said composition is a hair conditioning composition.
15. The composition of claim 1 wherein said composition is an agrochemical composition.
16. The composition of claim 1 wherein said composition is a paint composition.
17. A process for making a composition comprising vesicles having a vesicle permeability index of less than about 1.3 and water-soluble active material, said process comprising the steps of:
(a) providing a dialkyl quaternary ammonium compound having the formula:
wherein R1 and R2 are independently C12 to C20 saturated alkyl chains; Y is
wherein R4 is ethyl or isopropyl; R3 and R5 are independently methyl, ethyl, hydroxyethyl, or hydroxypropyl; m is 1, 2, or 3; n is 1 or 2; p is 0 or 1; and X− is an anion;
(b) heating said dialkyl quaternary ammonium compound to a temperature above a transition temperature of said dialkyl quaternary ammonium compound;
(c) adding said water-soluble active material to said dialkyl quaternary ammonium compound to form a mixture; and
(d) dispersing said mixture into water having a temperature above a transition temperature of said dialkyl quaternary ammonium compound.
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US12/793,912 Active 2025-10-26 US8506940B2 (en) | 2003-10-16 | 2010-06-04 | Aqueous compositions comprising vesicles having certain vesicle permeability |
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US (2) | US20050261134A1 (en) |
EP (1) | EP1673425B1 (en) |
JP (1) | JP4633722B2 (en) |
AT (1) | ATE401385T1 (en) |
DE (1) | DE602004015129D1 (en) |
ES (1) | ES2309593T3 (en) |
WO (1) | WO2005037973A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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US20070191256A1 (en) * | 2006-02-10 | 2007-08-16 | Fossum Renae D | Fabric care compositions comprising formaldehyde scavengers |
GB0717485D0 (en) | 2007-09-08 | 2007-10-17 | Unilever Plc | Improvements relating to fabric conditioners |
US9441187B2 (en) | 2012-05-07 | 2016-09-13 | Evonik Degussa Gmbh | Fabric softener active composition and method for making it |
BR112015013278A2 (en) | 2012-12-11 | 2017-07-11 | Colgate Palmolive Co | fabric conditioning composition |
BR102014025172B1 (en) | 2013-11-05 | 2020-03-03 | Evonik Degussa Gmbh | METHOD FOR MANUFACTURING A TRIS- (2-HYDROXYETHYL) -METHYLMETHYL ESTER OF FATTY ACID AND ACTIVE COMPOSITION OF SOFTENING CLOTHES |
UA119182C2 (en) | 2014-10-08 | 2019-05-10 | Евонік Дегусса Гмбх | Fabric softener active composition |
JP6530248B2 (en) * | 2015-06-12 | 2019-06-12 | 花王株式会社 | Softening processing method of textile products |
WO2023247298A1 (en) * | 2022-06-21 | 2023-12-28 | Firmenich Sa | Compositions for preventing, reducing, or ameliorating malodorous aldehydes and ketones, and uses thereof |
Citations (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4111854A (en) * | 1974-03-15 | 1978-09-05 | The Procter & Gamble Company | General purpose household cleaner |
US4424134A (en) * | 1983-06-15 | 1984-01-03 | The Procter & Gamble Company | Aqueous fabric softening compositions |
US4550862A (en) * | 1982-11-17 | 1985-11-05 | The Procter & Gamble Company | Liquid product pouring and measuring package with self draining feature |
US4767547A (en) * | 1986-04-02 | 1988-08-30 | The Procter & Gamble Company | Biodegradable fabric softeners |
US4981239A (en) * | 1989-01-03 | 1991-01-01 | The Procter & Gamble Company | Container having a drain-back spout |
US5089148A (en) * | 1990-11-27 | 1992-02-18 | Lever Brothers Company, Division Of Conopco, Inc. | Liquid fabric conditioner containing fabric softener and peach colorant |
US5392376A (en) * | 1994-04-11 | 1995-02-21 | Corning Incorporated | Gallium sulfide glasses |
US5409621A (en) * | 1991-03-25 | 1995-04-25 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening composition |
US5531910A (en) * | 1995-07-07 | 1996-07-02 | The Procter & Gamble Company | Biodegradable fabric softener compositions with improved perfume longevity |
US5545340A (en) * | 1993-03-01 | 1996-08-13 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
US5545350A (en) * | 1992-05-12 | 1996-08-13 | The Procter & Gamble Company | Concentrated fabric softener compositions containing biodegradable fabric softeners |
US5874396A (en) * | 1997-02-28 | 1999-02-23 | The Procter & Gamble Company | Rinse added laundry additive compositions having color care agents |
US5876705A (en) * | 1995-10-16 | 1999-03-02 | The Procter & Gamble Co. | Conditioning shampoo compositions |
US6093691A (en) * | 1996-08-19 | 2000-07-25 | The Procter & Gamble Company | Rinse added fabric softening compositions and method of use for the delivery of fragrance derivatives |
US6200586B1 (en) * | 1989-03-17 | 2001-03-13 | Albright & Wilson Limited | Biocidal and agrochemical suspensions |
US6218354B1 (en) * | 1997-12-10 | 2001-04-17 | The Procter & Gamble Company | Process for making a liquid fabric softening composition |
US6242526B1 (en) * | 1997-01-28 | 2001-06-05 | Stepan Company | Antimicrobial polymer latexes derived from unsaturated quaternary ammonium compounds and antimicrobial coatings, sealants, adhesives and elastomers produced from such latexes |
US6323172B1 (en) * | 1996-03-22 | 2001-11-27 | The Procter & Gamble Company | Concentrated, stable fabric softening composition |
US6468515B1 (en) * | 1998-06-04 | 2002-10-22 | The Procter & Gamble Company | Hair conditioning composition comprising high molecular weight ester oil |
US6479566B2 (en) * | 2000-07-06 | 2002-11-12 | International Coatings Limited | Antifouling paint |
US20030013799A1 (en) * | 2001-03-30 | 2003-01-16 | Regan Crooks | Aqueous suspension of nanoparticles comprising an agrochemical active ingredient |
US20030114338A1 (en) * | 2001-09-10 | 2003-06-19 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Fabric conditioning compositions |
US6589517B1 (en) * | 1999-09-30 | 2003-07-08 | The Procter & Gamble Company | Hair care compositions |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3264359D1 (en) * | 1981-02-28 | 1985-08-01 | Procter & Gamble | Textile treatment compositions |
GB9106308D0 (en) * | 1991-03-25 | 1991-05-08 | Unilever Plc | Fabric softening composition |
US5382376A (en) | 1992-10-02 | 1995-01-17 | The Procter & Gamble Company | Hard surface detergent compositions |
NO952329D0 (en) | 1995-06-13 | 1995-06-13 | Jotun As | Polymers for antifouling paints and processes for their preparation |
NO952537L (en) | 1995-06-23 | 1996-12-27 | Jotun As | Coarse paint |
US5948416A (en) | 1995-06-29 | 1999-09-07 | The Procter & Gamble Company | Stable topical compositions |
CA2226550C (en) * | 1995-07-11 | 2002-02-19 | The Procter & Gamble Company | Concentrated, stable fabric softening compositions including chelants |
US5972361A (en) | 1996-10-25 | 1999-10-26 | The Procter & Gamble Company | Cleansing products |
CA2272306A1 (en) | 1996-11-22 | 1998-05-28 | The Procter & Gamble Company | Cosmetic compositions |
-
2004
- 2004-10-13 WO PCT/US2004/033655 patent/WO2005037973A1/en active Application Filing
- 2004-10-13 JP JP2006527172A patent/JP4633722B2/en not_active Expired - Fee Related
- 2004-10-13 EP EP04809943A patent/EP1673425B1/en not_active Not-in-force
- 2004-10-13 ES ES04809943T patent/ES2309593T3/en active Active
- 2004-10-13 AT AT04809943T patent/ATE401385T1/en not_active IP Right Cessation
- 2004-10-13 DE DE602004015129T patent/DE602004015129D1/en active Active
- 2004-10-18 US US10/967,758 patent/US20050261134A1/en not_active Abandoned
-
2010
- 2010-06-04 US US12/793,912 patent/US8506940B2/en active Active
Patent Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4111854A (en) * | 1974-03-15 | 1978-09-05 | The Procter & Gamble Company | General purpose household cleaner |
US4550862A (en) * | 1982-11-17 | 1985-11-05 | The Procter & Gamble Company | Liquid product pouring and measuring package with self draining feature |
US4424134A (en) * | 1983-06-15 | 1984-01-03 | The Procter & Gamble Company | Aqueous fabric softening compositions |
US4767547A (en) * | 1986-04-02 | 1988-08-30 | The Procter & Gamble Company | Biodegradable fabric softeners |
US4981239A (en) * | 1989-01-03 | 1991-01-01 | The Procter & Gamble Company | Container having a drain-back spout |
US6200586B1 (en) * | 1989-03-17 | 2001-03-13 | Albright & Wilson Limited | Biocidal and agrochemical suspensions |
US5089148A (en) * | 1990-11-27 | 1992-02-18 | Lever Brothers Company, Division Of Conopco, Inc. | Liquid fabric conditioner containing fabric softener and peach colorant |
US5409621A (en) * | 1991-03-25 | 1995-04-25 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening composition |
US5545350A (en) * | 1992-05-12 | 1996-08-13 | The Procter & Gamble Company | Concentrated fabric softener compositions containing biodegradable fabric softeners |
US5574179A (en) * | 1993-03-01 | 1996-11-12 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compouds containing intermediate iodine value unsaturated fatty acid chains |
US5545340A (en) * | 1993-03-01 | 1996-08-13 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
US5562849A (en) * | 1993-03-01 | 1996-10-08 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
US5392376A (en) * | 1994-04-11 | 1995-02-21 | Corning Incorporated | Gallium sulfide glasses |
US5668102A (en) * | 1995-07-07 | 1997-09-16 | The Procter & Gamble Company | Biodegradable fabric softener compositions with improved perfume longevity |
US5531910A (en) * | 1995-07-07 | 1996-07-02 | The Procter & Gamble Company | Biodegradable fabric softener compositions with improved perfume longevity |
US5876705A (en) * | 1995-10-16 | 1999-03-02 | The Procter & Gamble Co. | Conditioning shampoo compositions |
US6323172B1 (en) * | 1996-03-22 | 2001-11-27 | The Procter & Gamble Company | Concentrated, stable fabric softening composition |
US6093691A (en) * | 1996-08-19 | 2000-07-25 | The Procter & Gamble Company | Rinse added fabric softening compositions and method of use for the delivery of fragrance derivatives |
US6242526B1 (en) * | 1997-01-28 | 2001-06-05 | Stepan Company | Antimicrobial polymer latexes derived from unsaturated quaternary ammonium compounds and antimicrobial coatings, sealants, adhesives and elastomers produced from such latexes |
US5874396A (en) * | 1997-02-28 | 1999-02-23 | The Procter & Gamble Company | Rinse added laundry additive compositions having color care agents |
US6218354B1 (en) * | 1997-12-10 | 2001-04-17 | The Procter & Gamble Company | Process for making a liquid fabric softening composition |
US6468515B1 (en) * | 1998-06-04 | 2002-10-22 | The Procter & Gamble Company | Hair conditioning composition comprising high molecular weight ester oil |
US6589517B1 (en) * | 1999-09-30 | 2003-07-08 | The Procter & Gamble Company | Hair care compositions |
US6479566B2 (en) * | 2000-07-06 | 2002-11-12 | International Coatings Limited | Antifouling paint |
US20030013799A1 (en) * | 2001-03-30 | 2003-01-16 | Regan Crooks | Aqueous suspension of nanoparticles comprising an agrochemical active ingredient |
US20030114338A1 (en) * | 2001-09-10 | 2003-06-19 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Fabric conditioning compositions |
Also Published As
Publication number | Publication date |
---|---|
EP1673425B1 (en) | 2008-07-16 |
DE602004015129D1 (en) | 2008-08-28 |
US8506940B2 (en) | 2013-08-13 |
ATE401385T1 (en) | 2008-08-15 |
JP2007508126A (en) | 2007-04-05 |
JP4633722B2 (en) | 2011-02-16 |
ES2309593T3 (en) | 2008-12-16 |
WO2005037973A1 (en) | 2005-04-28 |
US20100239513A1 (en) | 2010-09-23 |
EP1673425A1 (en) | 2006-06-28 |
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Legal Events
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AS | Assignment |
Owner name: PROCTER & GAMBLE COMPANY, THE, OHIO Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:DEMEYERE, HUGO JEAN MARIE;JOHANSSON, GUNNEL INDEGARD MATILDA;NYDEN, MAGNUS BO;REEL/FRAME:017168/0610;SIGNING DATES FROM 20050112 TO 20050202 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |