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EP1067174B1 - Procédé de production de particules de produit de réaction d'amine - Google Patents

Procédé de production de particules de produit de réaction d'amine Download PDF

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Publication number
EP1067174B1
EP1067174B1 EP99870147A EP99870147A EP1067174B1 EP 1067174 B1 EP1067174 B1 EP 1067174B1 EP 99870147 A EP99870147 A EP 99870147A EP 99870147 A EP99870147 A EP 99870147A EP 1067174 B1 EP1067174 B1 EP 1067174B1
Authority
EP
European Patent Office
Prior art keywords
acid
reaction product
composition
particles
amine reaction
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.)
Expired - Lifetime
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EP99870147A
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German (de)
English (en)
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EP1067174A1 (fr
Inventor
Alfred Busch
Johan Smets
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Procter and Gamble Co
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Procter and Gamble Co
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Filing date
Publication date
Priority to DE69920676T priority Critical patent/DE69920676D1/de
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to AT99870147T priority patent/ATE277999T1/de
Priority to EP99870147A priority patent/EP1067174B1/fr
Priority to AU57880/00A priority patent/AU5788000A/en
Priority to JP2001509452A priority patent/JP2003504488A/ja
Priority to PCT/US2000/018561 priority patent/WO2001004248A1/fr
Priority to US10/019,177 priority patent/US6764986B1/en
Priority to MXPA02000338 priority patent/MX228338B/es
Publication of EP1067174A1 publication Critical patent/EP1067174A1/fr
Application granted granted Critical
Publication of EP1067174B1 publication Critical patent/EP1067174B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/02—Inorganic compounds
    • C11D7/04—Water-soluble compounds
    • C11D7/08—Acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3209—Amines or imines with one to four nitrogen atoms; Quaternized amines
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3245—Aminoacids
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3263—Amides or imides
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/329—Carbohydrate or derivatives thereof

Definitions

  • the present invention relates to a process for producing particles of amine reaction product salt.
  • perfumed products are well-known in the art. However, consumer acceptance of such perfumed products like laundry and cleaning products is determined not only by the performance achieved with these products but also by the aesthetics associated therewith. The perfume components are therefore an important aspect of the successful formulation of such commercial products.
  • perfume additives make such compositions more aesthetically pleasing to the consumer, and in some cases the perfume imparts a pleasant fragrance to fabrics treated therewith.
  • the amount of perfume carried-over from an aqueous laundry bath onto fabrics is often marginal and does not last long on the fabric.
  • fragrance materials are often very costly and their inefficient use in laundry and cleaning compositions and ineffective delivery to fabrics results in a very high cost to both consumers and laundry and cleaning manufacturers. Industry, therefore, continues to seek with urgency for more efficient and effective fragrance delivery in laundry and cleaning products, especially for improvement in the provision of long-lasting fragrance to the fabrics.
  • viscous it is meant a product which has a viscosity higher than 1000 cps.
  • the viscosity is measured on a rheometer, TA Instrument CSL 2 100 at a temperature of 25C with a gap setting of 500 microns.
  • salt carrier a carrier which forms a salt with the amine reaction product.
  • the salt formation occurs by reacting the amine reaction product with an acid.
  • the salt formation takes place via a reaction of the acid at the nitrogen of the ⁇ -aminoketone or imine function.
  • the salt formation may also take place at other nucleophilic centers of the amine or amine reaction product. Indeed, it is believed that when the salt formation takes place at the nucleophilic center of the primary amine, the link nitrogen-active tends to be more labile and therefore may liberate the perfume in-situ.
  • Typical examples of such other suitable nucleophilic centers are the tertiary and secondary amine functions in polyethylenimine polymers.
  • the present invention is a process for making particles of salts of an amine reaction product of a selected type of amine compound containing a primary and/or secondary amine functional group and an active ketone or aldehyde containing component, and which comprises the steps of :
  • the obtained amine reaction product is further processed to form a coated particle.
  • the obtained particle or coated particle is incorporated in a finished composition.
  • the amine reaction product for use herein is a product of reaction between a compound containing a primary and/or secondary amine functional group and an active ketone or aldehyde containing component, so called hereinafter "amine reaction product".
  • primary and/or secondary amine it is meant a component which carries at least one primary and/or secondary amine and/or amide function.
  • the primary and/or secondary amine compound is also characterized by an Odour Intensity Index of less than that of a 1% solution of methylanthranilate in dipropylene glycol.
  • Odour Intensity Index it is meant that the pure chemicals were diluted at 1% in Dipropylene Glycol, odor-free solvent used in perfumery. This percentage is more representative of usage levels.
  • Smelling strips, or so called “blotters” were dipped and presented to the expert panellist for evaluation. Expert panellists are assessors trained for at least six months in odor grading and whose gradings are checked for accuracy and reproducibility versus a reference on an on-going basis. For each amine compound, the panellist was presented two blotters: one reference (Me Anthranilate, unknown from the panellist) and the sample. The panellist was asked to rank both smelling strips on the 0-5 odor intensity scale, 0 being no odor detected, 5 being very strong odor present.
  • a general structure for the primary amine compound of the invention is as follows: B-(NH2) n ; wherein B is a carrier material, and n is an index of value of at least 1.
  • Compounds containing a secondary amine group have a structure similar to the above excepted that the compound comprises one or more -NH- groups instead of -NH2. Further, the compound structure may also have one or more of both -NH2 and -NH- groups.
  • B carriers are organic carriers.
  • the primary and/or secondary amines which are useful herein are those selected from polyamines, amino acids and derivatives thereof, substituted amines and amides, glucamines, dendrimers, polyvinylamines and derivatives thereof, and/or copolymer thereof, alkylene polyamine, polyaminoacid and copolymer thereof, cross-linked polyaminoacids, amino substituted polyvinylalcohol, polyoxyethylene bis amine or bis aminoalkyl, aminoalkyl piperazine and derivatives thereof, bis (amino alkyl) alkyl diamine linear or branched, and mixtures thereof.
  • Preferred polyamines are polyethyleneimines commercially available under the tradename Lupasol like Lupasol FG (MW 800), G20wfv (MW 1300), PR8515 (MW 2000), WF (MW 25000), FC (MW 800), G20 (MW 1300), G35 (MW 1200), G100 (MW 2000), HF (MW 25000), P (MW 750000), PS (MW 750000), SK (MW 2000000), SNA (MW 1000000).
  • Preferred amino acids for use herein are selected tyrosine, tryptophane, lysine, glutamic acid, glutamine, aspartic acid, arginine, asparagine, phenylalanine, proline, glycine, serine, histidine, threonine, methionine, and mixture thereof, most preferably selected from tyrosine, tryptophane, and mixture thereof.
  • Preferred amino acid derivatives selected from tyrosine ethylate, glycine methylate, tryptophane ethylate, and mixture thereof.
  • Preferred substituted amines and amides for use herein are selected from nipecotamide, N-coco-1,3-propenediamine; N-oleyl-1,3-propenediamine; N-(tallow alkyl)-1,3-propenediamine; 1,4-diamino cyclohexane; 1,2-diaminocyclohexane; 1,12-diaminododecane, and mixtures thereof.
  • glucamines preferably selected from 2,3,4,5,6-pentamethoxy-glucamine; 6-acetylglucamine, glucamine, and mixture thereof.
  • PAMAM Starburst® polyamidoamines
  • amino-functional polymers are selected from the polyvinylamines, derivatives thereof, copolymer thereof, alkylene polyamine, polyaminoacids and copolymer thereof, cross-linked polyaminoacids, amino substituted polyvinylalcohol, polyoxyethylene bis amine or bis aminoalkyl, aminoalkyl piperazine and derivatives, N,N'-bis-(3-aminopropyl)-1,3-propanediamine linear or branched (TPTA), and mixtures thereof.
  • Preferred amino-functional polymers for use in the present invention are selected from the polyvinylamines, derivatives thereof, copolymer thereof, alkylene polyamine, polyaminoacids and copolymer thereof, cross-linked polyaminoacids, amino substituted polyvinylalcohol, polyoxyethylene bis amine or bis aminoalkyl, aminoalkyl piperazine and derivatives, N,N'-bis-(3-aminopropyl)-1,3-
  • Polyamino acid is one suitable and preferred class of amino-functional polymer.
  • Polyaminoacids are compounds which are made up of amino acids or chemically modified amino acids. They can contain alanine, serine, aspartic acid, arginine, valine, threonine, glutamic acid, leucine, cysteine, histidine, lysine, isoleucine, tyrosine, asparagine, methionine, proline, tryptophan, phenylalanine, glutamine, glycine or mixtures thereof.
  • chemically modified amino acids the amine or acidic function of the amino acid has reacted with a chemical reagent.
  • Preferred polyamino acids are polylysines, polyarginine, polyglutamine, polyasparagine, polyhistidine, polytryptophane or mixtures thereof. Most preferred are polylysines or polyamino acids where more than 50% of the amino acids are lysine, since the primary amine function in the side chain of the lysine is the most reactive amine of all amino acids.
  • the preferred polyamino acid has a molecular weight of 500 to 10.000.000, more preferably between 5.000 and 750.000.
  • the polyamino acid can be cross linked.
  • the cross linking can be obtained for example by condensation of the amine group in the side chain of the amino acid like lysine with the carboxyl function on the amino acid or with protein cross linkers like PEG derivatives.
  • the cross linked polyamino acids still need to have free primary and/or secondary amino groups left for reaction with the active ingredient.
  • the preferred cross linked polyamino acid has a molecular weight of 20.000 to 10.000.000, more preferably between 200.000 and 2.000.000.
  • the polyamino acid or the amino acid can be co-polymerized with other reagents like for instance with acids, amides, acyl chlorides. More specifically with aminocaproic acid, adipic acid, ethylhexanoic acid, caprolactam or mixture thereof.
  • the molar ratio used in these copolymers ranges from 1:1 (reagent/amino acid (lysine)) to 1:20, more preferably from 1:1 to 1:10.
  • the polyamino acid like polylysine can be partially ethoxylated.
  • polyaminoacids containing lysine, arginine, glutamime, asparagine are given in the Bachem 1996, Peptides and Biochemicals catalog.
  • polyaminoacid can be obtained before reaction with the active ingredient, under a salt form.
  • polylysine can be supplied as polylysine hydrobromide.
  • Polylysine hydrobromide is commercially available from Sigma, Applichem, Bachem and Fluka.
  • Suitable amino functional polymers containing at least one primary and/or secondary amine group for the purpose of the present invention are :
  • the more preferred compounds are selected from polyethyleneimine polymers commercially available under the tradename Lupasol like Lupasol FG, G20,wfv, PR8515, WF, FC, G20, G35, G100, HF, P, PS, SK, SNA; the diaminobutane dendrimers Astramol®, polylysine, cross-linked polylysine, N,N'-bis-(3-aminopropyl)-1,3-propanediamine linear or branched; 1,4-bis-(3-aminopropyl) piperazine, and mixtures thereof.
  • polyethyleneimine polymers commercially available under the tradename Lupasol like Lupasol FG, G20,wfv, PR8515, WF, FC, G20, G35, G100, HF, P, PS, SK, SNA
  • the diaminobutane dendrimers Astramol® polylysine, cross-linked polylysine, N,N'-bis-(
  • Even most preferred compounds are those selected from ethyl-4-amino benzoate, polyethyleneimine polymers commercially available under the tradename Lupasol like Lupasol FG, G20,wfv, PR8515, WF, FC, G20, G35, G100, HF, P, PS, SK, SNA; polylysine, cross-linked polylysine, N,N'-bis-(3-aminopropyl)-1,3-propanediamine linear or branched, 1,4-bis-(3-aminopropyl) piperazine, and mixtures thereof.
  • Lupasol like Lupasol FG, G20,wfv, PR8515, WF, FC, G20, G35, G100, HF, P, PS, SK, SNA polylysine, cross-linked polylysine, N,N'-bis-(3-aminopropyl)-1,3-propanediamine linear or branched, 1,4-bis-(3-amin
  • such most preferred primary and/or secondary amine compounds also provide fabric appearance benefit, in particular colour appearance benefit, thus providing a resulting amine reaction product with the dual properties of both fabric appearance benefit and delayed release of the active.
  • the primary and/or secondary amine compound has more than one free primary and/or secondary amine group, several different active ingredients (aldehyde and/or ketone) can be linked to the amine compound.
  • active ketone or active aldehyde it is meant any chain containing at least 1 carbon atom, preferably at least 5 carbon atoms.
  • the active ketone or active aldehyde is respectively selected from a flavour ketone or aldehyde ingredient, a pharmaceutical ketone or aldehyde active, a biocontrol ketone or aldehyde agent, a perfume ketone or aldehyde component and mixtures thereof; most preferably a perfume ketone and/or aldehyde.
  • Flavour ingredients include spices, flavor enhancers that contribute to the overall flavour perception.
  • Pharmaceutical actives include drugs.
  • Biocontrol agents include biocides, antimicrobials, bactericides, fungicides, algaecides, mildewcides, disinfectants, sanitiser like bleach, antiseptics, insecticides, insect and/or moth repellant, vermicides, plant growth hormones.
  • Typical antimicrobials include Glutaraldehyde, Cinnamaldehyde, and mixtures thereof.
  • Typical insect and/or moth repellants are perfume ingredients, such as citronellal, citral, N, N diethyl meta toluamide, Rotundial, 8-acetoxycarvotanacenone, and mixtures thereof.
  • Other examples of insect and/or moth repellant for use herein are disclosed in US 4,449,987, 4,693,890, 4,696,676, 4,933,371, 5,030,660, 5,196,200, and "Semio Activity of Flavor and Fragrance molecules on various Insect Species", B.D. Mookherjee et al., published in Bioactive Volatile Compounds from Plants , ASC Symposium Series 525, R. Teranishi, R.G. Buttery, and H. Sugisawa, 1993, pp. 35-48.
  • Perfume ketones components include components having odoriferous properties.
  • the perfume ketone is selected from buccoxime; iso jasmone; methyl beta naphthyl ketone; musk indanone; tonalid/musk plus; Alpha-Damascone, Beta-Damascone, Delta-Damascone, Iso-Damascone, Damascenone, Damarose, Methyl-Dihydrojasmonate, Menthone, Carvone, Camphor, Fenchone, Alpha-lonone, Beta-lonone, Gamma-Methyl so-called lonone, Fleuramone, Dihydrojasmone, Cis-Jasmone, Iso-E-Super, Methyl- Cedrenyl-ketone or Methyl- Cedrylone, Acetophenone, Methyl-Acetophenone, Para-Methoxy-Acetophenone, Methyl-Beta-Naph
  • the preferred ketones are selected from Alpha Damascone, Delta Damascone, Iso Damascone, Carvone, Gamma-Methyl-lonone, Iso-E-Super, 2,4,4,7-Tetramethyl-oct-6-en-3-one, Benzyl Acetone, Beta Damascone, Damascenone, methyl dihydrojasmonate, methyl cedrylone, hedione, and mixtures thereof.
  • Perfume aldehyde components include components having odoriferous properties.
  • the perfume aldehyde is selected from adoxal; anisic aldehyde; cymal; ethyl vanillin; florhydral; helional; heliotropin; hydroxycitronellal; koavone; lauric aldehyde; lyral; methyl nonyl acetaldehyde; P. T.
  • aldehydes are selected from citral, 1-decanal, benzaldehyde, florhydral, 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde; cis/trans-3,7-dimethyl-2,6-octadien-1-al; heliotropin; 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde; 2,6-nonadienal; alpha-n-amyl cinnamic aldehyde, alpha-n-hexyl cinnamic aldehyde, P.T. Bucinal, lyral, cymal, methyl nonyl acetaldehyde, trans-2-nonenal, lilial, trans-2-nonenal, and mixture thereof.
  • perfume ingredients some are commercial names conventionally known to one skilled in the art, and also includes isomers. Such isomers are also suitable for use in the present invention.
  • Odor Detection Threshold should be lower than 1ppm, preferably lower than 10ppb - measured at controlled Gas Chromatography (GC) conditions such as described here below.
  • GC Gas Chromatography
  • This parameter refers to the value commonly used in the perfumery arts and which is the lowest concentration at which significant detection takes place that some odorous material is present, as referred to for example in "Compilation of Odor and Taste Threshold Value Data (ASTM DS 48 A)", edited by F. A.
  • the Odor Detection Threshold is measured according to the following method : The gas chromatograph is characterized to determine the exact volume of material injected by the syringe, the precise split ratio, and the hydrocarbon response using a hydrocarbon standard of known concentration and chain-length distribution. The air flow rate is accurately measured and, assuming the duration of a human inhalation to last 0.02 minutes, the sampled volume is calculated.
  • GC 5890 Series II with FID detector 7673 Autosampler Column: J&W Scientific DB-1 Length 30 meters ID 0.25 mm film thickness 1 micron Method: Split Injection: 17/1 split ratio Autosampler: 1.13 microliters per injection Column Flow: 1.10 mL/minute Air Flow: 345 mL/minute Inlet Temp. 245°C Detector Temp. 285°C Temperature Information Initial Temperature: 50°C Rate: 5C/minute Final Temperature: 280°C Final Time: 6 minutes Leading assumptions: 0.02 minutes per sniff GC air adds to sample dilution
  • perfume components are those selected from : 2-methyl-2-(para-iso-propylphenyl)-propionaldehyde, 1-(2,6,6-trimethyl-2-cyclohexan-1-yl)-2-buten-1-one and/or para-methoxy-acetophenone.
  • the level of active is of from 10 to 90%, preferably from 30 to 85%, more preferably from 45 to 80% by weight of the amine reaction product.
  • Preferred amine reaction products are those resulting from the reaction of polyethyleneimine polymer like Lupasol polymers, BNPP, or TPTA with one or more of the following Alpha Damascone, Delta Damascone, Carvone, Gamma-Methyl-lonone, Hedione, Florhydral, Lilial, Heliotropine, and 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde.
  • Still other preferred amine reaction products are those resulting from the reaction of Astramol Dendrimers with Carvone as well as those resulting from the reaction of ethyl-4-amino benzoate with one or more of the following 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde, and trans-2-nonenal.
  • Still another preferred amine reaction products are those resulting from the reaction of polylysine with one or more of the following Alpha Damascone, Delta Damascone, Carvone, and 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde.
  • Most preferred amine reaction products are those from the reaction of Lupasol HF with Delta Damascone; LupasolG35 with Alpha Damascone; LupasolG100 with 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde, BNPP or TPTA with Alpha and Delta Damascone; ethyl-4-amino benzoate with 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde.
  • Another essential ingredient of the process invention is an anhydrous acid carrier.
  • an anhydrous acid carrier By means of this carrier, particles of amine reaction product will be easily and quickly produced.
  • the amine reaction product and the carrier material are in close physical proximity, more preferably in close contact, most preferably in intimate admixture within said obtained particle.
  • Typical of these acid carrier for use herein are the commonly known organic acids or inorganic acids, which fall under the description of Bronsted or Lewis acids.
  • Suitable acid carrier for use herein have a pKa relative to water of from minus 9 to 16, more preferably from minus 2 to 10, most preferably from 0 to 7.
  • alcohols like phenol derivatives are suitable acid carrier for use herein.
  • a typical example of such phenol derivative is picric acid which has a pKa of 0.25.
  • Preferred organic or inorganic acids include those conventionally known as solid binders or agglomerating agents. More preferred organic acids are substantially water soluble solid binders or agglomerating agents. Most preferred are organic acids used in detergent applications, for example as builders.
  • substantially water soluble shall refer to a material that is soluble in distilled (or equivalent) water, at 25°C., at a concentration of 0.2% by weight, and are preferably soluble at 1.0% by weight.
  • a “solid” is defined as a material that is a solid at ambient temperatures, and so solid substantially water-soluble binder or agglomerating agent must have a melting point of at least 30°C, and preferably of at least 40°C.
  • Suitable water-soluble binders or agglomerating agents as organic acid carriers include monocarboxylic acids, monomeric polycarboxylic acids, homo or copolymeric polycarboxylic acids, inorganic acids, and mixtures thereof.
  • Suitable example of monocarboxylic acids containing one carboxy group include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and mixtures thereof.
  • Suitable monocarboxylic acids are the monocarboxylic acids substituted by any of the following groups: CH3- (CH2)n, wherein n is an integer of value of at least 1, CH3, OH, NH2, Cl, Br, F, I, OR", NHR", NR"2, NO2, SO3, cyclic rings like cyclopentane, cyclohexane, phenyl, benzyl, or a mixture of these substituents; wherein R" is selected from saturated or unsaturated alkyl chains.
  • Preferred examples are 1-methylcyclohexanecarboxylic acid, glycolic acid, mandelic acid, lactic acid, salicylic acid, benzoic acid, and derivatives thereof.
  • the substituents may also be anywhere in the alkyl chain attached to the acidic function.
  • the alkyl chain can be saturated or non saturated.
  • organic acids suitable for use herein as acid carrier includes the polycarboxylic acids containing two carboxy groups.
  • these ingredients are selected from succinic acid, malonic acid, (ethylenedioxy) diacetic acid, maleic acid, diglycolic acid, tartaric acid, tartronic acid, fumaric acid, oxalic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, or sebacic acid, as well as the ether carboxylic acid and the sulfinyl carboxylic acids, and mixtures thereof.
  • dicarboxylic acids suitable for use herein are the dicarboxylic acids substituted by CH3- (CH2)n, wherein n is an integer of value of at least 1, CH3, OH, NH2, Cl, Br, F, I, OR", NHR", NR"2, NO2, SO3, cyclic rings like cyclopentane, cyclohexane, phenyl, benzyl, or a mixture of these substituents; wherein R" is selected from saturated or unsaturated alkyl chain.
  • Preferred examples of such substituted dicarboxylic acids are phtalic acid, isophtalic acid, terephtalic acid, malic acid, fumaric acid, tartaric acid, or mixtures thereof.
  • the substituents may also be anywhere in the alkyl chain attached to the acidic functions.
  • the alkyl chains can be saturated or non saturated.
  • polycarboxylic acids suitable for use herein are the polycarboxylic acids containing three carboxy groups and include, in particular, water-soluble citric acid, aconitric and citraconic acid as well as succinic derivatives such as the carboxymethyloxysuccinic described in British Patent No. 1,379,241, lactoxysuccinic described in British Patent No. 1,389,732, and aminosuccinic described in Netherlands Application 7205873, and the oxypolycarboxylic materials such as 2-oxa-1,1,3-propane tricarboxylic described in British Patent No. 1,387,447.
  • polycarboxylic acids suitable for use herein are the polycarboxylic acids containing four carboxy groups and include oxydisuccinic disclosed in British Patent No. 1,261,829, 1,1,2,2-ethane tetracarboxylic, 1,1,3,3-propane tetracarboxylic and 1,1,2,3-propane tetracarboxylic.
  • Polycarboxylic containing sulfo substituents include the sulfosuccinic derivatives disclosed in British Patent Nos. 1,398,421 and 1,398,422 and in U.S. Patent No. 3,936,448, and the sulfonated pyrolysed citratic described in British Patent No. 1,439,000.
  • Alicyclic and heterocyclic polycarboxylic include cyclopentane-cis,cis,cis-tetracarboxylic, cyclopentadienide pentacarboxylic, 2,3,4,5-tetrahydrofuran - cis, cis, cis-tetracarboxylic, 2,5-tetrahydrofuran - cis - dicarboxylic, 2,2,5,5-tetrahydrofuran - tetracarboxylic, 1,2,3,4,5,6-hexane - hexacarboxylic, polyacrylic acid, polymaleic acid, polymaleic-acrylic acids, sugar-acids like glucose-phosphonic acid, gluconic acid, glucuronic acid, mannanic acid, galactonic acid, arabinamic acid, and carboxymethyl derivatives of polyhydric alcohols such as sorbitol, mannitol and xylitol.
  • Suitable carriers are amino acids like, glycine, lysine, alanine, valine, leucine, isoleucine, proline, phenylalanine, tyrosine, tryptophan, serine, threonine, cysteine, methionine, asparagine, glutamine, aspartate, glutamate, arginine, histidine, and mixtures thereof.
  • Suitable acid carriers are the so called inorganic acids like for example HF, HCl, HBr, HI, H 2 SO 4 , H 2 SO 3 , H 2 CO 3 , HNO 2 , HNO 3 , HClO 4 , HClO 3 , HClO 2 , HClO, or H 3 PO 4 , H 4 P 2 O 7 , or H 5 P 3 O 10 or mixture thereof.
  • acid carriers are the protonated forms of the anionic surfactants, like the protonated form of the linear C 11-13 alkyl benzene sulfonate anionic surfactant.
  • Acid anhydrides react in the presence of water to acids. Sometimes, the production of the amine reaction product is followed by the incomplete removal of the water in the amine samples. It may then be desired to remove the remaining water by reacting it with the acid anhydrides to form acids which in turn make the salt with the amine reaction product.
  • acids where the acidic proton is linked to C, N, S, Si or other non-oxygen atoms.
  • Example of such acids is 2,4-pentanedione.
  • the acid carrier is used in its anhydrous forms.
  • citric acid is available under anhydrous form or as a monohydrate.
  • the preferred acid carriers are polycarboxylic acids selected from citric acid, tartaric acid, malonic acid, succinic acid, oxalic acid, adipic acid, maleic acid, malic acid, phtalic acid, succinic acid, hydroxysuccinic acid, polyacrylic acid, and mixtures thereof.
  • the amine reaction product when the amine reaction product is mixed with such acid carrier, the amine reaction product will be present in an amount of from 10 to 85%, preferably 20 to 80%, more preferably 45 to 75% by weight of the processed reaction product in the produced particle.
  • the amount of carrier will be sufficient to add up to 100%.
  • the particle may also contain minors but in quantities which will not exceed the amount of carrier material.
  • the processed particle may contain one or more additional ingredients like a surfactant for improved solubility or dispersability.
  • Typical of such surfactant are the anionic, nonionic, or cationic surfactants.
  • the weight ratio of such additional ingredient(s) to the carrier is of up to 1:1.
  • the acid carrier will be present in an amount of from 5 to 90%, preferably from 15 to 80% and most preferably from 20 to 70%, by weight of the produced particles in the processed amine reaction product.
  • Processing of the amine reaction product with the acid carrier is done by first dissolving the amine reaction product in anhydrous solvent, preferably ethanol. Separately, the acid carrier is also dissolved in the same solvent that is used for the amine reaction product. The two solutions are then slowly added together, by adding the solution of the acid carrier to the solution of the amine reaction product whilst maintaining the temperature upon the addition to room temperature. During the addition the salt of the amine reaction product and the acid carrier precipitate resulting a solid powder. The solvent is removed by either filtering off the salt and drying or by evaporation of the solvent. Preferably the salt is obtained by filtering off.
  • a coating on the particle can be provided, which depending on the nature of this coating will give ease of dispersion, improved storage stability, flowability and/or improved fabric substantivity of the coated particle.
  • Suitable coating materials suitable for use herein are those having a melting point between 30°C and 135°C, preferably between 45°C and 85°C.
  • Suitable additional coating materials for use in the process invention are components like organic polymeric compounds, waxes, paraffins, oils, glycerides, monoglycerides, diglycerides, triglycerides, fatty acids, anionic surfactants; nonionic surfactants, cationic surfactants, zwitterionic surfactants, and mixtures thereof, preferably are selected from organic polymeric compound, nonionic surfactants, and mixtures thereof.
  • Preferred organic polymeric compounds suitable for mixing with primary and/or secondary amine compound herein include polyethylene glycols, and derivatives thereof, particularly those of molecular weight 1000-10000, more particularly 2000 to 8000 and most preferably about 4000.
  • any nonionic surfactants useful for detersive purposes can be included in the compositions provided it has a melting point between 30°C and 135°C.
  • Nonionic polyhydroxy fatty acid amide surfactant Nonionic polyhydroxy fatty acid amide surfactant
  • Polyhydroxy fatty acid amides suitable for use herein are those having the structural formula R2CONR1Z wherein : R1 is H, C 1 -C 4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl, or a mixture thereof, preferable C1-C4 alkyl, more preferably C 1 or C 2 alkyl, most preferably C 1 alkyl (i.e., methyl); and R2 is a C 5 -C 31 hydrocarbyl, preferably straight-chain C 5 -C 19 alkyl or alkenyl, more preferably straight-chain C 9 -C 17 alkyl or alkenyl, most preferably straight-chain C 11 -C 17 alkyl or alkenyl, or mixture thereof; and Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof. Z preferably will be derived
  • polyethylene, polypropylene, and polybutylene oxide condensates of alkyl phenols are suitable for use herein.
  • the polyethylene oxide condensates are preferred.
  • These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to about 18 carbon atoms in either a straight chain or branched chain configuration with the alkylene oxide with from about 1 to about 150 moles of alkylene oxide per mole of alcohol.
  • the alkyl ethoxylate condensation products of aliphatic alcohols with from about 1 to about 150 moles of ethylene oxide are suitable for use herein.
  • the alkyl chain of the aliphatic alcohol can either be straight or branched, primary or secondary, and generally contains from 6 to 22 carbon atoms.
  • Particularly preferred are the condensation products of alcohols having an alkyl group containing from 8 to 20 carbon atoms with from about 25 to about 150 moles of ethylene oxide per mole of alcohol, preferably 50 to 100, more preferably 80 moles of ethylene oxide per mole of alcohol.
  • Preferred nonionic ethoxylated alcohol surfactants are selected from tallow (C 16 -C 18 ) alcohol ethoxylated with 25, 50, 80, or 100 moles of ethylene oxide commercially available from under the tradename of Lutensol from BASF, Empilan from Albright and Wilson, and Genapol from Clariant.
  • the most preferred nonionic ethoxylated alcohol surfactant is tallow (C 16 -C 18 ) alcohol ethoxylated with 80moles of ethylene oxide and commercially available under the tradename of Lutensol 80/80 from BASF, Empilan KM 80 from Albright and Wilson, or Genapol T800 from Clariant.
  • the ethoxylated C 6 -C 22 fatty alcohols and C 6 -C 22 mixed ethoxylated/propoxylated fatty alcohols are suitable surfactants for use herein, particularly where water soluble.
  • the ethoxylated fatty alcohols are the C 10 -C 22 ethoxylated fatty alcohols with a degree of ethoxylation of from 25 to 150, most preferably these are the C 12 -C 18 ethoxylated fatty alcohols with a degree of ethoxylation from 50 to 80.
  • the mixed ethoxylated/propoxylated fatty alcohols have an alkyl chain length of from 10 to 18 carbon atoms, a degree of ethoxylation of from 3 to 30 and a degree of propoxylation of from 1 to 30.
  • the condensation products of ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol are suitable for use herein.
  • the hydrophobic portion of these compounds preferably has a molecular weight of from about 1500 to about 1800 and exhibits water insolubility.
  • Examples of compounds of this type include certain of the commercially-available PluronicTM surfactants, marketed by BASF.
  • condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylenediamine are suitable for use herein.
  • the hydrophobic moiety of these products consists of the reaction product of ethylenediamine and excess propylene oxide, and generally has a molecular weight of from about 2500 to about 3000.
  • this type of nonionic surfactant include certain of the commercially available TetronicTM compounds, marketed by BASF.
  • Suitable alkylpolysaccharides for use herein are disclosed in U.S. Patent 4,565,647, Llenado, issued January 21, 1986, having a hydrophobic group containing from about 6 to about 30 carbon atoms, preferably from about 10 to about 16 carbon atoms and a polysaccharide, e.g., a polyglycoside, hydrophilic group containing from about 1.3 to about 10, preferably from about 1.3 to about 3, most preferably from about 1.3 to about 2.7 saccharide units.
  • Any reducing saccharide containing 5 or 6 carbon atoms can be used, e.g., glucose, galactose and galactosyl moieties can be substituted for the glucosyl moieties.
  • the hydrophobic group is attached at the 2-, 3-, 4-, etc. positions thus giving a glucose or galactose as opposed to a glucoside or galactoside.
  • the intersaccharide bonds can be, e.g., between the one position of the additional saccharide units and the 2-, 3-, 4-, and/or 6- positions on the preceding saccharide units.
  • the preferred alkylpolyglycosides have the formula R2O((CnH2n)O)t(glycosyl) x wherein R2 is selected from the group consisting of alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl, and mixtures thereof in which the alkyl groups contain from 10 to 18, preferably from 12 to 14, carbon atoms; n is 2 or 3; t is from 0 to 10, preferably 0, and X is from 1.3 to 8, preferably from 1.3 to 3, most preferably from 1.3 to 2.7.
  • the glycosyl is preferably derived from glucose.
  • Nonionic fatty acid amide surfactant Nonionic fatty acid amide surfactant
  • Fatty acid amide surfactants suitable for use herein are those having the formula: R 6 CON(R 7 ) 2 wherein R 6 is an alkyl group containing from 7 to 21, preferably from 9 to 17 carbon atoms and each R 7 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, and -(C 2 H 4 O) x H, where x is in the range of from 1 to 3.
  • Preferred coating materials from those above mentioned are the nonionic ethoxylated alcohol surfactants having a melting point between 30°C and 135°C.
  • suitable water-soluble binders or agglomerating agents include the water soluble organic polymeric compounds, water soluble monomeric polycarboxylates, or their acid forms, homo or copolymeric polycarboxylic acids or their salts in which the polycarboxylic acid comprises at least two carboxylic radicals separated from each other by not more that two carbon atoms.
  • Suitable organic polymeric compounds suitable as coating agents include cellulose derivatives such as methylcellulose, carboxymethylcellulose, hydroxypropylcellulose and hydroxyethylcellulose, as well as carbohydrates like pectins, and gums. Further compounds are carbohydrates and derivatives such as fructose, xylose, galactose, galacturonic acid or glucose based polymers like inuline, dextran, xyloglucan, pectin or gums
  • Suitable carboxylates containing one carboxy group include the water soluble salts of lactic acid, glycolic acid and ether derivatives thereof.
  • Polycarboxylates containing two carboxy groups include the water-soluble salts of succinic acid, malonic acid, (ethylenedioxy) diacetic acid, maleic acid, diglycolic acid, tartaric acid, tartronic acid and fumaric acid, as well as the ether carboxylates and the sulfinyl carboxylates.
  • Polycarboxylates containing three carboxy groups include, in particular, water-soluble citrates, aconitrates and citraconates as well as succinate derivatives such as the carboxymethyloxysuccinates described in British Patent No.
  • Polycarboxylates containing four carboxy groups include oxydisuccinates disclosed in British Patent No. 1,261,829, 1,1,2,2-ethane tetracarboxylates, 1,1,3,3-propane tetracarboxylates and 1,1,2,3-propane tetracarboxylates.
  • Polycarboxylates containing sulfo substituents include the sulfosuccinate derivatives disclosed in British Patent Nos. 1,398,421 and 1,398,422 and in U.S. Patent No. 3,936,448, and the sulfonated pyrolysed citrates described in British Patent No. 1,439,000.
  • Alicyclic and heterocyclic polycarboxylates include cyclopentane-cis,cis,cis-tetracarboxylates, cyclopentadienide pentacarboxylates, 2,3,4,5-tetrahydrofuran - cis, cis, cis-tetracarboxylates, 2,5-tetrahydrofuran - cis - dicarboxylates, 2,2,5,5-tetrahydrofuran - tetracarboxylates, 1,2,3,4,5,6-hexane - hexacarboxylates and carboxymethyl derivatives of polyhydric alcohols such as sorbitol, mannitol and xylitol.
  • Aromatic polycarboxylates include mellitic acid, pyromellitic acid and the phthalic acid derivatives disclosed in British Patent No. 1,425,343.
  • the preferred polycarboxylates are hydroxycarboxylates containing up to three carboxy groups per molecule, more particularly citrates.
  • water-soluble binders or agglomerating agents as coating materials include, carbonates, bicarbonates, borates, phosphates, sulfate salts like sodium and magnesium sulfate, inorganic perhydrate salts including perborate like perborate monohydrate, percarbonate, silicates, starch, cyclodextrin, clay as defined hereinafter like smectite and bentonite clay and mixtures of any of the foregoing.
  • Borate, as well as builders containing borate-forming materials that can produce borate under detergent storage or wash conditions can also be used but are not preferred at wash conditions less that about 50°C, especially less than about 40°C.
  • carbonates are the alkaline earth and alkali metal carbonates, including sodium carbonate and sesqui-carbonate and mixtures thereof with ultra-fine calcium carbonate as disclosed in German Patent Application No. 2,321,001 published on November 15, 1973.
  • water-soluble phosphates are the alkali metal tripolyphosphates, sodium, potassium and ammonium pyrophosphate, sodium and potassium and ammonium pyrophosphate, sodium and potassium orthophosphate, sodium polymeta/phosphate in which the degree of polymerization ranges from about 6 to 21, and salts of phytic acid.
  • Suitable silicates include the water soluble sodium silicates with an SiO 2 : Na 2 O ratio of from 1.0 to 2.8, with ratios of from 1.6 to 2.4 being preferred, and 2.0 ratio being most preferred.
  • the silicates may be in the form of either the anhydrous salt or a hydrated salt.
  • Sodium silicate with an SiO 2 : Na 2 O ratio of 2.0 is the most preferred silicate.
  • Typical disclosure of cyclodextrin derivatives are disclosed in W096/05358, U.S. Pat. Nos: 3,426,011, Parmerter et al., issued Feb. 4, 1969; 3,453,257; 3,453,258; 3,453,259; and 3,453,260, all in the names of Parmerter et al., and all issued July 1, 1969; 3,459,731, Gramera et al., issued Aug. 5, 1969; 3,553,191, Parmerter et al., issued Jan. 5, 1971; 3,565,887, Parmerter et al., issued Feb. 23, 1971; 4,535,152, Szejtli et al., issued Aug.
  • partially water soluble coating agents may also be used as coating agent. These compounds are indeed less preferred because during the wash cycle the amine reaction product will still be at least partially coated and therefore can not display its full functionality of long lasting freshness on dry fabrics or hard surfaces.
  • partially water soluble coating agents include the crystalline layered silicates.
  • largely water insoluble builders include the sodium aluminosilicates.
  • Crystalline layered sodium silicates have the general formula NaMSi x O x+1.y H 2 O wherein M is sodium or hydrogen, x is a number from 1.9 to 4 and y is a number from 0 to 20. Crystalline layered sodium silicates of this type are disclosed in EP-A-0164514 and methods for their preparation are disclosed in DE-A-3417649 and DE-A-3742043.
  • x in the general formula above has a value of 2, 3 or 4 and is preferably 2.
  • the most preferred material is ⁇ -Na 2 Si 2 O 5 , available from Hoechst AG as NaSKS-6.
  • Suitable aluminosilicate zeolites have the unit cell formula Na z [(AlO 2 ) z (SiO 2 )y]. XH 2 O wherein z and y are at least 6; the molar ratio of z to y is from 1.0 to 0.5 and x is at least 5, preferably from 7.5 to 276, more preferably from 10 to 264.
  • the aluminosilicate material are in hydrated form and are preferably crystalline, containing from 10% to 28%, more preferably from 18% to 22% water in bound form.
  • the aluminosilicate ion exchange materials can be naturally occurring materials, but are preferably synthetically derived. Synthetic crystalline aluminosilicate ion exchange materials are available under the designations Zeolite A, Zeolite B, Zeolite P, Zeolite X, Zeoilte MAP, Zeolite HS and mixtures thereof.
  • Zeolite A has the formula Na 12 [AlO 2 ) 12 (SiO 2 ) 12 ].xH 2 O wherein x is from 20 to 30, especially 27.
  • Zeolite X has the formula Na 86 [(AlO 2 ) 86 (SiO 2 ) 106 ].276 H 2 O.
  • the amine reaction product when the amine reaction product is mixed with an acid carrier and further processed to form a coated particle, the amine reaction product will be present in an amount of from 1 to 85%, preferably 5 to 24% by weight of the processed reaction product in the produced particle.
  • the coating agent will be present in an amount of from 10% to 95%, preferably from 30 to 90%, more preferably, 50 to 75% by weight of the particle of the processed amine reaction product.
  • the amount of carrier will be sufficient to add up to 100%.
  • the coated particle may also contain minors but in quantities which will not exceed either of the amount of carrier material or coating agent.
  • Preferred coating materials are selected from nonionic ethoxylated alcohol surfactants having a melting point between 30°C and 135°C, carbonate, starch, cyclodextrin, and mixtures thereof.
  • the surface treatment of the particle can be carried out in a number of ways using equipment known in the art and the process may be taken in batch wise or continuous fashion.
  • One method for applying the coating material involves agglomeration. Any conventional agglomerator/mixer may be used including, but not limited to pan, rotary drum and vertical blender types. Molten coating compositions may also be applied either by being poured onto, or spray atomized onto a moving bed of the mixture of amine reaction product with carrier.
  • Another method for applying the coating is to pour the obtained mixture (so-called particle), as herein before described, onto the coating material and agglomerate it in a Braun Mixer. Care is also taken that the temperature during the mixing and/or coating step does not substantially exceed the melting point of the carrier material. For example, 130g of a mixture containing the citric acid salt of the amine reaction product and 39g of PEG 4000 is poured at 60°C into a Braun Mixer containing 50g of carbonate. The mixing of the ingredients is carried out for about 5 minutes. Care is also taken that the temperature during the coating does not exceed 60°C. The agglomerated particle can then be used as is for incorporation into the finished composition.
  • Still another preferred marketing execution is by mixing the particle with a solvent capable of dissolving the particle, thereby enabling the spraying of the resulting mixture.
  • the finished compositions aspect of the invention comprises the incorporation of the hereinbefore described processed amine reaction product salt together with one or more laundry or cleaning ingredient in a finished composition.
  • Finished compositions incorporating the processed amine reaction product salt will normally contain from 0.01 to 25%, more preferably from 0.02 to 10%, and most preferably from 0.05 to 5% of the processed product on a composition weight basis.
  • Laundry compositions of the invention which also encompass compositions providing color care, are suitable for use in any steps of the domestic treatment, that is as a pre-treatment composition, as a wash additive as a composition suitable for use in the rinse-cycle of the laundry cycle or applied on a dryer-sheet.
  • a pre-treatment composition as a wash additive as a composition suitable for use in the rinse-cycle of the laundry cycle or applied on a dryer-sheet.
  • multiple applications can be made such as treating the fabric with a pre-treatment composition of the invention and also thereafter with a composition of the invention suitable for use in the rinse cycle and/or suitable for use as a dryer-sheet.
  • liquid finished compositions of the invention may also be in a spray, foam, or aerosol form which for example can be suitable for use while ironing, or applied on the surfaces of the tumble dryer.
  • the incorporation of the processed amine reaction product salt is conveniently made depending on its end form by dry-addition, as is or in coated form.
  • Laundry compositions encompass laundry detergent compositions, including liquid, solid form like powdered, tablets as well as softening compositions including rinse added softening composition as well as dryer added softening compositions.
  • the finished composition is a detergent composition, more preferably in solid form.
  • the detergent composition comprises a clay.
  • compositions of the invention may preferably contain a clay, preferably present at a level of from 0.05% to 40%, more preferably from 0.5% to 30%, most preferably from 2% to 20% by weight of the composition.
  • clay mineral compound as used herein, excludes sodium aluminosilicate zeolite builder compounds, which however, may be included in the compositions of the invention as optional components.
  • One preferred clay may be a bentonite clay.
  • Highly preferred are smectite clays, as for example disclosed in the US Patents No.s 3,862,058 3,948,790, 3,954,632 and 4,062,647 and European Patents No.s EP-A-299,575 and EP-A-313,146 all in the name of the Procter and Gamble Company.
  • smectite clays herein includes both the clays in which aluminium oxide is present in a silicate lattice and the clays in which magnesium oxide is present in a silicate lattice. Smectite clays tend to adopt an expandable three layer structure.
  • Suitable smectite clays include those selected from the classes of the montmorillonites, hectorites, volchonskoites, nontronites, saponites and sauconites, particularly those having an alkali or alkaline earth metal ion within the crystal lattice structure.
  • Sodium or calcium montmorillonite are particularly preferred.
  • Suitable smectite clays are sold by various suppliers including English China Clays, Laviosa, Georgia Kaolin and Colin Stewart Minerals.
  • Clays for use herein preferably have a particle dimension of from 10nm to 800nm more preferably from 20nm to 500 mm, most preferably from 50nm to 200 mm.
  • Particles of the clay mineral compound may be included as components of agglomerate particles containing other detergent compounds.
  • the term "largest particle dimension" of the clay mineral compound refers to the largest dimension of the clay mineral component as such, and not to the agglomerated particle as a whole.
  • Substitution of small cations, such as protons, sodium ions, potassium ions, magnesium ions and calcium ions, and of certain organic molecules including those having positively charged functional groups can typically take place within the crystal lattice structure of the smectite clays.
  • a clay may be chosen for its ability to preferentially absorb one cation type, such ability being assessed by measurements of relative ion exchange capacity.
  • the smectite clays suitable herein typically have a cation exchange capacity of at least 50 meq/100g.
  • U.S. Patent No. 3,954,632 describes a method for measurement of cation exchange capacity.
  • the crystal lattice structure of the clay mineral compounds may have, in a preferred execution, a cationic fabric softening agent substituted therein.
  • a cationic fabric softening agent substituted therein Such substituted clays have been termed 'hydrophobically activated' clays.
  • the cationic fabric softening agents are typically present at a weight ratio, cationic fabric softening agent to clay, of from 1:200 to 1:10, preferably from 1:100 to 1:20.
  • Suitable cationic fabric softening agents include the water insoluble tertiary amines or dilong chain amide materials as disclosed in GB-A-1 514 276 and EP-B-0 011 340.
  • a preferred commercially available "hydrophobically activated" clay is a bentonite clay containing approximately 40% by weight of a dimethyl ditallow quaternary ammonium salt sold under the tradename Claytone EM by English China Clays International.
  • the clay is present in an intimate mixture or in a particle with a humectant and a hydrophobic compound, preferably a wax or oil, such as paraffin oil.
  • humectants are organic compounds, including propylene glycol, ethylene glycol, dimers or trimers of glycol, most preferably glycerol.
  • the particle is preferably an agglomerate.
  • the particle may be such that the wax or oil and optionally the humectant form an encapsulate on the clay or alternatively, the clay be a encapsulate for the wax or oil and the humectant. It may be preferred that the particle comprises an organic salt or silica or silicate.
  • the clay is preferably mixed with one or more surfactants and optionally builders and optionally water, in which case the mixture is preferably subsequently dried.
  • a mixture is further processed in a spray-drying method to obtain a spray dried particle comprising the clay.
  • the flocculating agent is also comprised in the particle or granule comprising the clay.
  • the intimate mixture comprises a chelating agent.
  • compositions of the invention may contain a clay flocculating agent, preferably present at a level of from 0.005% to 10%, more preferably from 0.05% to 5%, most preferably from 0.1% to 2% by weight of the composition.
  • the clay flocculating agent functions such as to bring together the particles of clay compound in the wash solution and hence to aid their deposition onto the surface of the fabrics in the wash. This functional requirement is hence different from that of clay dispersant compounds which are commonly added to laundry detergent compositions to aid the removal of clay soils from fabrics and enable their dispersion within the wash solution.
  • Preferred as clay flocculating agents herein are organic polymeric materials having an average weight of from 100,000 to 10,000,000, preferably from 150,000 to 5,000,000, more preferably from 200,000 to 2,000,000.
  • Suitable organic polymeric materials comprise homopolymers or copolymers containing monomeric units selected from alkylene oxide, particularly ethylene oxide, acrylamide, acrylic acid, vinyl alcohol, vinyl pyrrolidone, and ethylene imine. Homopolymers of, on particular, ethylene oxide, but also acrylamide and acrylic acid are preferred.
  • EP-A-299,575 and EP-A-313,146 in the name of the Procter and Gamble Company describe preferred organic polymeric clay flocculating agents for use herein.
  • the weight ratio of clay to the flocculating polymer is preferably from 1000:1 to 1:1, more preferably from 500:1 to 1:1, most preferably from 300:1 to 1:1, or even more preferably from 80:1 to 10:1, or in certain applications even from 60:1 to 20:1.
  • Inorganic clay flocculating agents are also suitable herein, typical examples of which include lime and alum.
  • the flocculating agent is preferably present in a detergent base granule such as a detergent agglomerate, extrudate or spray-dried particle, comprising generally one or more surfactants and builders.
  • Effervescent means may also be optionally used in the compositions of the invention.
  • Effervescency as defined herein means the evolution of bubbles of gas from a liquid, as the result of a chemical reaction between a soluble acid source and an alkali metal carbonate, to produce carbon dioxide gas, i.e. C 6 H 8 O 7 + 3NaHCO 3 ⁇ Na 3 C 6 H 5 O 7 + 3CO 2 ⁇ + 3H 2 O
  • Suitable alkali and/ or earth alkali inorganic carbonate salts herein include carbonate and hydrogen carbonate of potassium, lithium, sodium, and the like amongst which sodium and potassium carbonate are preferred.
  • Suitable bicarbonates to be used herein include any alkali metal salt of bicarbonate like lithium, sodium, potassium and the like, amongst which sodium and potassium bicarbonate are preferred.
  • the choice of carbonate or bicarbonate or mixtures thereof may be made depending on the pH desired in the aqueous medium wherein the granules are dissolved.
  • the inorganic alkali and/ or earth alkali carbonate salt of the compositions of the invention comprises preferably a potassium or more preferably a sodium salt of carbonate and/ or bicarbonate.
  • the carbonate salt comprises sodium carbonate, optionally also a sodium bicarbonate.
  • the inorganic carbonate salts herein are preferably present at a level of at least 20% by weight of the composition. Preferably they are present at a level of at least 23% or even 25% or even 30% by weight, preferably up to about 60% by weight or more preferably up to 55% or even 50% by weight.
  • detergent granules such as agglomerates or spray dried granules.
  • an effervescence source is present, preferably comprising an organic acid, such as carboxylic acids or aminoacids, and a carbonate. Then it may be preferred that part or all of the carbonate salt herein is premixed with the organic acid, and thus present in an separate granular component.
  • Preferred effervescent source are selected from compressed particles of citric acid and carbonate optionally with a binder; and particle of carbonate, bicarbonate and malic or maleic acid in weight ratios of 4:2:4.
  • the dry add form of citric acid and carbonate are preferably used.
  • the carbonate may have any particle size.
  • the carbonate salt in particular when the carbonate salt is present in a granule and not as separately added compound, the carbonate salt has preferably a volume median particle size from 5 to 375 microns, whereby preferably at least 60%, preferably at least 70% or even at least 80% or even at least 90% by volume, has a particle size of from 1 to 425 microns.
  • the carbon dioxide source has a volume median particle size of 10 to 250, whereby preferably at least 60 %, or even at least 70% or even at least 80% or even at least 90% by volume, has a particle size of from 1 to 375 microns; or even preferably a volume median particle size from 10 to 200 microns, whereby preferably at least 60 %, preferably at least 70% or even at least 80% or even at least 90% by volume, has a particle size of from 1 to 250 microns.
  • the carbonate salt when added as separate component, so to say 'dry-added' or admixed to the other detergent ingredients, the carbonate may have any particle size, including the above specified particle sizes, but preferably at least an volume average particle size of 200 microns or even 250 microns or even 300 microns.
  • the carbon dioxide source of the required particle size is obtained by grinding a larger particle size material, optionally followed by selecting the material with the required particle size by any suitable method.
  • percarbonate salts may be present in the compositions of the invention as a bleaching agent, they are not included in the carbonate salts as defined herein
  • the preferred detergent composition will, preferably contain a bleach precursor, a source of alkaline hydrogen peroxide necessary to form a peroxyacid bleaching species in the wash solution and preferably will also contain other components conventional in detergent compositions.
  • preferred detergent compositions will incorporate one or more of surfactants, organic and inorganic builders, soil suspending and antiredeposition agents, suds suppressors, enzymes, fluorescent whitening agents, photoactivated bleaches, perfumes, colours, and mixtures thereof.
  • composition of the invention may take a variety of physical form including liquid, gel, foam in either aqueous or non-aqueous form, granular and tablet forms.
  • a packaged composition comprising the processed product of the invention or composition of the invention.
  • the packaged composition is a closed packaging system having a moisture vapour transmission rate of less than 20g/m 2 /24 hours. Typical disclosure of such a package can be found in WO 98/40464.
  • Still another preferred package is a spray dispenser.
  • the present invention also relates to such compositions incorporated into a spray dispenser to create an article of manufacture that can facilitate treatment of fabric articles and/or surfaces with said compositions containing the amine reaction product and other ingredients (examples are cyclodextrins, polysaccharides, polymers, surfactant, perfume, softener) at a level that is effective, yet is not discernible when dried on the surfaces.
  • the spray dispenser comprises manually activated and non-manual powered (operated) spray means and a container containing the treating composition. Typical disclosure of such spray dispenser can be found in WO 96/04940 page 19 line 21 to page 22 line 27.
  • the articles of manufacture preferably are in association with instructions for use to ensure that the consumer applies sufficient ingredient of the composition to provide the desired benefit.
  • compositions to be dispensed from a sprayer contain a level of amine reaction product of from about 0.01% to about 5%, preferably from about 0.05% to about 2%, more preferably from about 0.1% to about 1%, by weight of the usage composition.
  • Also provided herein is a method for providing a delayed release of an active ketone or aldehyde which comprises the step of contacting the surface to be treated with a a compound or composition of the invention, and thereafter contacting the treated surface with a material, preferably an aqueous medium like moisture or any other means susceptible of releasing the active from the amine reaction product.
  • surface it is meant any surface onto which the compound can deposit. Typical examples of such material are fabrics, hard surfaces such as dishware, floors, bathrooms, toilet, kitchen, paper, skin, and other surfaces in need of a delayed release of a perfume ketone and/or aldehyde such as that with litter like animal litter.
  • the surface is selected from a fabric, a tile, a ceramic; more preferably is a fabric.
  • delayed release is meant release of the active component (e.g perfume) over a longer period of time than by the use of the active (e.g., perfume) itself.
  • ⁇ -amino ketone from Lupasol G100 (commercially available from BASF with a content of 50 % water, 50 % Lupasol G100 (Mw. 5000)) and ⁇ -Damascone (or ⁇ -Damascone) was prepared using any one of these three different procedures described as follows:
  • Lupasol G35 or Lupasol HF is used instead of Lupasol G100.
  • the obtained mixture (so-called particle), as herein before described, is pour onto the coating material and agglomerated it in a Braun Mixer. Care is taken that the temperature during the mixing and/or coating step does not substantially exceed the melting point of the carrier material. For example, 130g of a mixture containing the citric acid salt of the amine reaction product and 39g of PEG 4000 is poured at 60°C into a Braun Mixer containing 50g of carbonate. The mixing of the ingredients is carried out for about 5 minutes. Care is also taken that the temperature during the coating does not exceed 60°C.
  • detergent compositions were prepared: A B C Blown Powder Zeolite A 15.0 15.0 15.0 Sulfate 0.0 5.0 0.0 LAS 3.0 3.0 3.0 QAS - 1.5 1.5 DTPMP 0.4 0.2 0.4 EDDS - 0.4 0.2 CMC 0.4 0.4 0.4 MA/AA 4.0 2.0 2.0 Agglomerates LAS 5.0 5.0 5.0 TAS 2.0 2.0 1.0 Silicate 3.0 3.0 4.0 Zeolite A 8.0 8.0 8.0 Carbonate 8.0 8.0 4.0 Spray On Perfume 0.3 0.3 0.3 C45E7 2.0 2.0 2.0 C25E3 2.0 - - Dry additives Citrate 5.0 - 2.0 Bicarbonate - 3.0 - Carbonate 8.0 15.0 10.0 TAED 6.0 2.0 5.0 PB1 14.0 7.0 10.0 PEO - - 0.2 PARP3 0.2 0.
  • composition in the form of a tablet, bar, extrudate or granule in accord with the invention A B C D E F G Sodium C 1 -C 13 alkylbenzenesulfonate 12.0 16.0 23.0 19.0 18.0 20.0 16.0 Sodium C 14 -C 15 alcohol sulfate 4.5 - - - 4.0 C 14 -C 15 alcohol ethoxylate (3) sulfate - - 2.0 - 1.0 1.0 1.0 1.0 Sodium C 14 -C 15 alcohol ethoxylate 2.0 2.0 - 1.3 - - 5.0 C 9 -C 14 alkyl dimethyl hydroxy ethyl quaternary ammonium salt - - 1.0 0.5 2.0 Tallow fatty acid - - - - 1.0 Sodium tripolyphosphate / Zeolite 23.0 25.0 14.0 22,0 20.0 10.0 20.0 Sodium carbonate 25.0 22.0 35.0 20.0 28.0 41.0 30.0 Sodium Polyacrylate (45%)
  • perfume, PVP, PVPVI/PVNO, brightener, photo-bleach 2.0 1.0 1.0 1.0 2.5 1.5 1.0 PARP2 1.6 2.0 0.8 0.2 1.0 0.16 0.5 H I J K Sodium C 11 -C 13 alkylbenzenesulfonate 23.0 13.0 20.0 18.0 Sodium C 14 -C 15 alcohol sulfate - 4.0 - - Clay I or II 5.0 10.0 14.0 6.0 Flocculating agent I or II 0.2 0.3 0.1 0.9 Wax 0.5 0.5 1.0 - Humectant (glycerol/ silica) 0.5 2.0 1.5 - C 14 -C 15 alcohol ethoxylate sulfate - - 2.0 Sodium C 14 -C 15 alcohol ethoxylate ( 2.5 3.5 - - C 9 -C 14 alkyl dimethyl hydroxy ethyl quaternary ammonium salt - - 0.5 Tallow fatty acid 0.5 - - - Tallow alcohol e
  • detergent additive compositions were prepared according to the present invention : A B C LAS - 5.0 5.0 STPP 30.0 - 20.0 Zeolite A - 35.0 20.0 PB1 20.0 15.0 - TAED 10.0 8.0 - PARP1 0.1 - 0.1 PARP2 - 0.4. 0.2 Protease - 0.3 0.3 Amylase - 0.06 0.06 Minors, water and miscellaneous Up to 100%
  • liquid dishwashing detergent compositions of density 1.40Kg/L were prepared according to the present invention : A B C D STPP 17.5 17.5 17.2 16.0 Carbonate 2.0 - 2.4 - Silicate 5.3 6.1 14.6 15.7 NaOCI 1.15 1.15 1.15 1.25 Polygen/carbopol 1.1 1.0 1.1 1.25 Nonionic - - 0.1 - NaBz 0.75 0.75 - - PARP3 0.08 0.2 0.1 0.5 NaOH - 1.9 - 3.5 KOH 2.8 3.5 3.0 - pH 11.0 11.7 10.9 11.0 Sulphate, miscellaneous and water up to 100%
  • liquid rinse aid compositions were prepared according to the present invention : A B C Nonionic 12.0 - 14.5 Nonionic blend - 64.0 - Citric 3.2 - 6.5 HEDP 0.5 - - PEG - 5.0 - SCS 4.8 - 7.0 Ethanol 6.0 8.0 - PARP5 3 - 1 PARP3 - 0.2 0.1 pH of the liquid 2.0 7.5 / Miscellaneous and water Up to 100%
  • liquid dishwashing compositions were prepared according to the present invention : A B C D E C17ES 28.5 27.4 19.2 34.1 34.1 Amine oxide 2.6 5.0 2.0 3.0 3.0 C12 glucose amide - - 6.0 - - Betaine 0.9 - - 2.0 2.0 Xylene sulfonate 2.0 4.0 - 2.0 - Neodol C11E9 - - 5.0 - - Polyhydroxy fatty acid amide - - - 6.5 6.5 Sodium diethylene penta acetate - - 0.03 - - (40%) TAED - - - 0.06 0.06 Sucrose - - - 1.5 1.5 Ethanol 4.0 5.5 5.5 9.1 9.1 Alkyl diphenyl oxide disulfonate - - - - 2.3 Ca formate - - - 0.5 1.1 Ammonium citrate 0.06 0.1 - - - Na chloride - 1.0 - - - Mg chloride
  • the following spray composition for cleaning of hard surfaces and removing household mildew was prepared according to the present invention : PARP3 0.3 Amylase 0.01 Protease 0.01 Na octyl sulfate 2.0 Na dodecyl sulfate 4.0 Na hydroxide 0.8 Silicate 0.04 Butyl carbitol 4.0 Perfume 0.35 Water/minors up to 100%
  • lavatory cleansing block compositions were prepared according to the present invention.
  • the following toilet bowl cleaning composition was prepared according to the present invention.
  • pre-soak fabric conditioning and/or fabric enhancement compositions according to the present invention which can be suitably used in the laundry rinse cycle.
  • the perfume 1, 2, and 3 have the following compositions: Perfume 1 2 3 Perfume Ingredients Wt.% Wt.% Wt.% Anisic aldehyde - - 2 Benzophenone 3 5 - Benzyl acetate 10 15 5 Benzyl salicylate 5 20 5 Cedrol 2 - - Citronellol 10 - 5 Coumarin - - 5 Cymal - - 3 Dihydromyrcenol 10 - 5 Flor acetate 5 - 5 Galaxolide 10 - - Lilial 10 15 20 Linalyl acetate 4 - 5 Linalool 6 15 5 Methyl dihydro jasmonate 3 10 5 Phenyl ethyl acetate 2 5 1 Phenyl ethyl alcohol 15 15 20 alpha-Terpineol 5 - 8 Vanillin - - 1 Total 100 100 100 100 100 100 100 100 100

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Claims (24)

  1. Procédé pour préparer des particules d'un produit de réaction aminé d'un composé contenant un groupe fonctionnel amine primaire et/ou secondaire et qui est choisi parmi
    i) les polyamines ;
    ii) les acides aminés et des dérivés de ceux-ci ;
    iii) les amines et amides substitués ;
    iv) les glucamines ;
    v) les dendrimères ;
    vi) les polyvinylamines et des dérivés et/ou copolymères de celles-ci;
    vii) les alkylène polyamines ;
    viii) les polyaminoacides et copolymères de ceux-ci ;
    ix) les polyaminoacides réticulés ;
    x) les alcools polyvinyliques substitués par un groupe amino ;
    xi) les polyoxyéthylène bis amines ou bis aminoalkyles ;
    x) les aminoalkylpipérazines et des dérivés de celles-ci ;
    xi) les bis(aminoalkyl)diamines, linéaires ou ramifiées ; et
    xii) des mélanges de ceux-ci ;
    avec un constituant contenant une cétone active ou un aldéhyde actif, et qui comprend les étapes consistant :
    a) à fournir un produit de réaction aminé ayant une viscosité supérieure à 1000 cP, et
    b) à mélanger avec celui-ci un véhicule acide anhydre pour former ainsi un sel du produit de réaction aminé traité ; et
    c) à façonner ensuite ledit sel du produit de réaction aminé traité en particules.
  2. Procédé selon la revendication 1, dans lequel le composé a un indice d'intensité d'odeur inférieur à celui d'une solution à 1 % d'anthranilate de méthyle dans du dipropylèneglycol.
  3. Procédé selon l'une des revendications 1 ou 2, dans lequel l'amine primaire et/ou secondaire est choisie parmi les polymères polyéthylèneimines ; une polylysine, une polylysine réticulée, la N,N'-bis-(3-aminopropyl)-1,3-propanediamine linéaire ou ramifiée, la 1,4-bis-(3-aminopropyl)pipérazine, et des mélanges de ceux-ci.
  4. Procédé selon l'une quelconque des revendications 1 à 3, dans lequel le produit actif est choisi parmi un ingrédient d'arôme cétone ou aldéhyde, un produit actif cétone ou aldéhyde pharmaceutique, un agent de biocontrôle cétone ou aldéhyde, un constituant de parfum cétone ou aldéhyde, un agent de refroidissement rafraíchissant cétone ou aldéhyde et/ou des mélanges de ceux-ci.
  5. Procédé selon l'une quelconque des revendications 1 à 4, dans lequel ledit constituant actif est un produit insectifuge et/ou antimite, de préférence choisi parmi le citronellal, le citral, le N,N diéthyl méta toluamide, le Rotundial, la 8-acétoxycarvotanacénone, et des mélanges de ceux-ci.
  6. Procédé selon l'une quelconque des revendications 1 à 4, dans lequel ledit constituant actif est un antimicrobien, de préférence choisi parmi le glutaraldéhyde, le cinnamaldéhyde et des mélanges de ceux-ci.
  7. Procédé selon l'une quelconque des revendications 1 à 4, dans lequel le produit actif est un parfum, de préférence choisi parmi l'alpha-damascone, la delta damascone, la Carvone, la gamma-méthyl-ionone ; la Damascénone, l'hédione, le 2,4-diméthyl-3-cyclohexèn-1-carboxaldéhyde, le Florhydral, le Lilial, l'héliotropine, le trans-2-nonénal, le citral et des mélanges de ceux-ci.
  8. Procédé selon l'une quelconque des revendications 1 à 7, dans lequel la quantité de produit de réaction aminé se situe de 10 à 85 %, de préférence de 20 à 80 %, mieux encore de 45 à 75 %, en poids des particules.
  9. Procédé selon l'une quelconque des revendications 1 à 8, dans lequel le véhicule acide a un pKa par rapport à l'eau de moins 9 à 16, de préférence de moins 2 à 10, mieux encore de 0 à 7.
  10. Procédé selon l'une quelconque des revendications 1 à 9, dans lequel le véhicule acide est choisi parmi les acides organiques, les acides minéraux et des mélanges de ceux-ci, est de préférence un acide organique choisi parmi les acides monocarboxyliques, les acides polycarboxyliques monomères, les acides polycarboxyliques homo ou copolymères, les acides minéraux et des mélanges de ceux-ci, est mieux encore un acide polycarboxylique choisi parmi l'acide citrique, l'acide tartrique, l'acide malonique, l'acide oxalique, l'acide adipique, l'acide maléique, l'acide malique, l'acide phtalique, l'acide succinique, l'acide hydroxysuccinique, un acide polyacrylique, et des mélanges de ceux-ci.
  11. Procédé selon l'une quelconque des revendications 1 à 10, dans lequel la quantité de matière véhicule acide se situe de 5 à 90 %, de préférence de 15 à 80 % et mieux encore de 20 à 70 %, en poids des particules.
  12. Procédé selon l'une quelconque des revendications 1 à 11, dans lequel lesdites particules sont traitées pour former une particule enrobée.
  13. Procédé selon l'une quelconque des revendications 1 à 12, dans lequel les particules sont traitées, en outre, avec un matériau d'enrobage choisi parmi les agents tensioactifs non ioniques de type alcool éthoxylé ayant un point de fusion entre 30 °C et 135 °C, les polyéthylèneglycols, du carbonate, de l'amidon, la cyclodextrine, les sels sulfates, et des mélanges de ceux-ci.
  14. Procédé selon la revendication 13, dans lequel la quantité de produit de réaction aminé se situe de 1 à 85 %, de préférence 15 à 55 % en poids de la particule enrobée.
  15. Particules d'un sel de produit de réaction aminé traité obtenues par le procédé selon les revendications 1 à 14.
  16. Procédé d'incorporation de particules d'un sel de produit de réaction aminé traité selon la revendication 15 dans un produit fini, comprenant la combinaison desdites particules avec un ou plusieurs ingrédients de nettoyage ou de blanchissage.
  17. Composition finie comprenant un ou plusieurs ingrédients de nettoyage ou de blanchissage et des particules d'un sel de produit de réaction aminé traité selon la revendication 15.
  18. Composition selon la revendication 17, dans laquelle ladite composition est choisie parmi une composition de blanchissage, une composition de nettoyage de surface dure et une composition soins personnels.
  19. Composition selon la revendication 18, dans laquelle ladite composition est une composition détergente de blanchissage comprenant, en outre, une argile.
  20. Composition selon la revendication 19, dans laquelle la composition détergente de blanchissage comprend, en outre, un agent de floculation.
  21. Procédé pour délivrer un produit actif résiduel à une surface, qui comprend les étapes consistant à mettre en contact ladite surface avec des particules selon la revendication 15, ou une composition selon l'une quelconque des revendications 17 à 20, puis à mettre en contact la surface traitée avec un matériau de sorte que l'ingrédient actif soit libéré.
  22. Utilisation de particules telles que définies dans la revendication 15, pour la fabrication d'une composition de blanchissage et/ou de nettoyage pour délivrer un parfum résiduel sur une surface sur laquelle elle est appliquée.
  23. Utilisation de particules telles que définies dans la revendication 15, pour la fabrication d'une composition de blanchissage et/ou de nettoyage pour délivrer un parfum résiduel et un agent d'entretien du linge sur les tissus sur lesquels elle est appliquée.
  24. Composition conditionnée comprenant les particules selon la revendication 15 ou une composition selon l'une quelconque des revendications 17 à 20.
EP99870147A 1999-07-08 1999-07-08 Procédé de production de particules de produit de réaction d'amine Expired - Lifetime EP1067174B1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AT99870147T ATE277999T1 (de) 1999-07-08 1999-07-08 Verfahren zur herstellung von amin- umsetzungsprodukt-teilchen
EP99870147A EP1067174B1 (fr) 1999-07-08 1999-07-08 Procédé de production de particules de produit de réaction d'amine
DE69920676T DE69920676D1 (de) 1999-07-08 1999-07-08 Verfahren zur Herstellung von Amin-Umsetzungsprodukt-Teilchen
JP2001509452A JP2003504488A (ja) 1999-07-08 2000-07-06 アミン反応生成物の粒子の製造方法
AU57880/00A AU5788000A (en) 1999-07-08 2000-07-06 Process for producing particles of amine reaction product
PCT/US2000/018561 WO2001004248A1 (fr) 1999-07-08 2000-07-06 Procede de production de particules d'un produit de reaction amine
US10/019,177 US6764986B1 (en) 1999-07-08 2000-07-06 Process for producing particles of amine reaction products
MXPA02000338 MX228338B (es) 1999-07-08 2000-07-06 Proceso para producir particulas de producto de reaccion dje amina.

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US6958148B1 (en) 1998-01-20 2005-10-25 Pericor Science, Inc. Linkage of agents to body tissue using microparticles and transglutaminase
US6906012B1 (en) 1999-11-09 2005-06-14 Procter & Gamble Company Detergent compositions comprising a fragrant reaction product
MX239674B (es) * 1999-12-22 2006-08-22 Procter & Gamble Procedimiento para fabricar un producto detergente.
JP4703090B2 (ja) * 2001-08-30 2011-06-15 日本メナード化粧品株式会社 毛髪処理剤組成物およびその製造方法
ATE416246T1 (de) 2001-09-06 2008-12-15 Procter & Gamble Duftkerzen
GB2382586A (en) 2001-12-03 2003-06-04 Procter & Gamble Fabric treatment compositions
ES2307676T3 (es) * 2002-01-11 2008-12-01 CHEMISCHE FABRIK DR. WEIGERT GMBH & CO. KG Uso de un concentrado de producto de limpieza y procedimiento para la limpieza de instrumental quirurgico.
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ES2435773T3 (es) 2005-09-02 2013-12-23 The Procter & Gamble Company Personalización de aroma para lavado de ropa
US20070275866A1 (en) * 2006-05-23 2007-11-29 Robert Richard Dykstra Perfume delivery systems for consumer goods
WO2011002872A1 (fr) 2009-06-30 2011-01-06 The Procter & Gamble Company Composition de conditionnement de tissu à multiples utilisations avec aminosilicone
EP2270124A1 (fr) * 2009-06-30 2011-01-05 The Procter & Gamble Company Compositions de blanchiment comportant un système de livraison de parfum
CN102471739B (zh) 2009-07-09 2016-05-11 宝洁公司 制备香料颗粒的方法
SG173230A1 (en) * 2010-01-25 2011-08-29 Rohm & Haas Laundry detergent bar composition
EP2395070A1 (fr) * 2010-06-10 2011-12-14 The Procter & Gamble Company Composition détergente liquide pour linge comprenant une lipase d'origine bactérienne
US10913921B2 (en) * 2014-06-18 2021-02-09 HEX Performance, LLC Performance gear, textile technology, and cleaning and protecting systems and methods
CA2959691A1 (fr) * 2014-09-26 2016-03-31 The Procter & Gamble Company Produits comprenant des matieres de reduction des mauvaises odeurs
WO2018124090A1 (fr) * 2016-12-27 2018-07-05 花王株式会社 Composition détergente en poudre pour article textile
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EP1067174A1 (fr) 2001-01-10
AU5788000A (en) 2001-01-30
WO2001004248A1 (fr) 2001-01-18
MXPA02000338A (es) 2002-06-21
MX228338B (es) 2005-06-07
ATE277999T1 (de) 2004-10-15
JP2003504488A (ja) 2003-02-04

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