WO2000002986A2 - Procede servant a preparer des particules de produit de reaction d'amine - Google Patents

Procede servant a preparer des particules de produit de reaction d'amine Download PDF

Info

Publication number
WO2000002986A2
WO2000002986A2 PCT/US1999/015679 US9915679W WO0002986A2 WO 2000002986 A2 WO2000002986 A2 WO 2000002986A2 US 9915679 W US9915679 W US 9915679W WO 0002986 A2 WO0002986 A2 WO 0002986A2
Authority
WO
WIPO (PCT)
Prior art keywords
reaction product
bis
mixtures
amine reaction
process according
Prior art date
Application number
PCT/US1999/015679
Other languages
English (en)
Other versions
WO2000002986A3 (fr
Inventor
Marcel Homble
Alfred Busch
Rafael Trujillo
Christophe Laudamiel
Johan Smets
Jean Wevers
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from EP98870227A external-priority patent/EP0971025A1/fr
Priority claimed from EP98870226A external-priority patent/EP0971024A1/fr
Priority claimed from EP99870025A external-priority patent/EP0971026A1/fr
Priority claimed from EP99870026A external-priority patent/EP0971027A1/fr
Priority to EP99932389A priority Critical patent/EP1144578B1/fr
Priority to AU48703/99A priority patent/AU4870399A/en
Priority to CA002335576A priority patent/CA2335576C/fr
Priority to ES99932389T priority patent/ES2237123T3/es
Priority to US09/720,401 priority patent/US6451751B1/en
Priority to DE69923227T priority patent/DE69923227T2/de
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AT99932389T priority patent/ATE286962T1/de
Priority to BRPI9912023-2A priority patent/BR9912023B1/pt
Priority to JP2000559208A priority patent/JP2002524573A/ja
Publication of WO2000002986A2 publication Critical patent/WO2000002986A2/fr
Publication of WO2000002986A3 publication Critical patent/WO2000002986A3/fr

Links

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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation

Definitions

  • the present invention relates to a process for producing particles of amine reaction product.
  • 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.
  • the mixing of the amine reaction product with a carrier having specific melting point to form a particle fulfills such a need.
  • the obtained particle is thereafter treated to form a coated particle.
  • both viscous and non- viscous amine reaction product when processed by the present invention exhibit better deposition and long lasting release than amine reaction product which have not been processed according to this process.
  • the mixing with such carrier act as a shell around the amine reaction product, thus protecting it from the aggressive wash liquor as well as enhancing its fabric deposition properties.
  • 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.
  • the carrier for use herein has a melting point, measured at atmospheric pressure, of from 30°C to 135°C.
  • the present invention is a process for making particles of amine reaction product of a compound containing a primary and/or secondary amine functional group and an active ketone or aldehyde containing component, and which comprises the steps of : a)-providing the amine reaction product, and b)-mixing therewith a carrier having a melting point of from 30°C to 135°C.
  • the obtained particle is further processed to form a coated particle.
  • 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
  • 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 method
  • Odour Intensity Index it 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.
  • Preferred B carriers are inorganic or organic carriers.
  • inorganic carrier it is meant carrier which are non-or substantially non carbon based backbones.
  • Preferred primary and/or secondary amines, among the inorganic carriers are those selected from mono or polymers or organic-organosilicon copolymers of amino derivatised organo silane, siloxane, silazane, alumane, aluminum siloxane, or aluminum silicate compounds.
  • Typical examples of such carriers are: organosiloxanes with at least one primary amine moiety like the diaminoalkylsiloxane [H2NCH2(CH3) 2Si]0, or the organoaminosilane (C6H5) 3SiNH2 described in: Chemistry and Technology of Silicone, W. Noll, Academic Press Inc. 1998, London, pp 209, 106).
  • Preferred primary and/or secondary amines are those selected from aminoaryl derivatives, polyamines, amino acids and derivatives thereof, substituted amines and amides, glucamines, dendrimers, the polyvinylamines with a MW of from 600-50K; amino substituted polyvinylalcohol with a MW ranging from 400-300,000; polyoxyethylene bis [amine]; polyoxyethylene bis [6-aminohexyl]; N,N'-bis-(3-aminopropyl)-1 ,3- propanediamine linear or branched; 1 ,4-bis-(3-aminopropyl) piperazine, and mixtures thereof.
  • Preferred aminoaryl derivatives are the amino-benzene derivatives including the alkyl esters of 4-amino benzoate compounds, and more preferably selected from ethyl-4-amino benzoate, phenylethyl-4-aminobenzoate, phenyl-4- aminobenzoate, 4-amino-N'-(3-aminopropyl)-benzamide, and mixtures thereof.
  • Preferred polyamines are polyethyleneimines commercially available under the tradename Lupasol like Lupasol FG, G20,wfv, PR8515, WF, FC, G20, G35, G100, HF, P, PS, SK, SNA.
  • 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-diamino- cyclohexane; 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.
  • 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. This is often done to protect these chemical amine and acid functions of the amino acid in a subsequent reaction or to give special properties to the amino acids, like improved solubility.
  • 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 :
  • Polyamino acid (L-lysine / lauric acid in a molar ratio of 10/1), Polyamino acid (L-lysine / aminocaproic acid / adipic acid in a molar ratio of 5/5/1), ), Polyamino acid (L-lysine / aminocaproic acid /ethylhexanoic acid in a molar ratio of 5/3/1) Polyamino acid (polylysine-cocaprolactam); Polylysine hydrobromide; cross- linked polylysine,
  • TPTA N,N'-bis-(3-aminopropyl)-1 ,3-propanediamine linear or branched
  • BNPP - 1 ,4-bis-(3-aminopropyl) piperazine
  • the more preferred compounds are 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; glucamine; the diaminobutane dendrimers Astramol ® , polyvinylamines with a MW ranging from 600, 1200, 3K, 20K, 25K or 50K; amino substituted polyvinylalcohol with a MW ranging from 400-300,000; polyoxyethylene bis [amine]; polyoxyethylene bis [6-aminohexyl]; polyaminoacid, cross-linked polyaminoacid, N,N'-bis-(3- aminopropyl)-1 ,3-propanediamine linear or branched; 1 ,4-bis-(3-aminopropyl) piperazine, and mixture thereof
  • Most preferred primary and/or secondary amine compounds are 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; the diaminobutane dendrimers Astramol ® , N,N'-bis-(3-aminopropyl)-1 ,3- propanediamine linear or branched; 1 ,4-bis-(3-aminopropyl) piperazine, and mixtures thereof.
  • 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; N,N'-bis-(3-aminopropyl)-1 ,3-propanediamine linear or branched, 1 ,4-bis-(3-aminopropyl) piperazine, polylysine, cross-linked polylysine, and mixtures thereof.
  • Lupasol like Lupasol FG, G20,wfv, PR8515, WF, FC, G20, G35, G100, HF, P, PS, SK, SNA N,N'-bis-(3-aminopropyl)-1 ,3-propanediamine linear or branched, 1 ,4-bis-(3-aminopropyl) piperaz
  • 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-Napht
  • Indanone 4-Damascol, Dulcinyl or Cassione, Gelsone, Hexalon, Isocyclemone E, Methyl Cyclocitrone, Methyl-Lavender-Ketone, Orivon, Para-tertiary-Butyl- Cyclohexanone, Verdone, Delphone, Muscone, Neobutenone, Plicatone, Veloutone, 2,4,4, 7-Tetramethyl-oct-6-en-3-one, Tetrameran, hedione, and mixtures thereof.
  • 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.
  • 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. Please refer 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. Since the precise concentration at the detector at any point in time is known, the mass per volume inhaled is known and hence the concentration of material.
  • solutions are delivered to the sniff port at the back-calculated concentration. A panelist sniffs the GC effluent and identifies the retention time when odor is noticed. The average over all panelists determines the threshold of noticeability. The necessary amount of analyte is injected onto the column to achieve a certain concentration, such as 10 ppb, at the detector. Typical gas chromatograph parameters for determining odor detection thresholds are listed below.
  • 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 which have a Dry Surface Odour Index as per given in co-pending application EP 98870155.3 given at page 29, line 26 to page 32 line 29, in which the specified unperfumed base for fabric sufaces and hard surfaces are respectively as follow:
  • Most 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.
  • Even most preferred amine reaction products are those from the reaction of Lupasol HF with Delta Damascone; LupasolG35 with Alpha Damascone; LupasolGIOO 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 a carrier having a melting point between 30°C and 135°C, preferably between 45°C and 85°C. By means of this carrier, particles of amine reaction product will be produced.
  • Suitable carrier for use in the process invention are components like organic polymeric compounds, waxes, paraffins, oils, glycerides, monoglycerides, diglycerides, triglycerides, anionic surfactants; nonionic surfactants, cationic surfactants, zwitterionic surfactants, and mixtures thereof, preferably 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.
  • Polyhydroxy fatty acid amides suitable for use herein are those having the structural formula R2CONR1Z wherein : R1 is H, C-1-C4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl, or a mixture thereof, preferable C1-C4 alkyl, more preferably C-
  • C31 hydrocarbyl preferably straight-chain C5-C19 alkyl or alkenyl, more preferably straight-chain C9-C17 alkyl or alkenyl, most preferably straight-chain
  • 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 from a reducing sugar in a reductive amination reaction; more preferably Z is a glycityl.
  • 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 ⁇ -C22 fatty alcohols and C5-C22 mixed ethoxylated/propoxylated fatty alcohols are suitable surfactants for use herein, particularly where water soluble.
  • the ethoxylated fatty alcohols are the C10- 22 ethoxylated fatty alcohols with a degree of ethoxylation of from 25 to 150, most preferably these are the C12- -I8 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 PluronicT 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.
  • nonionic surfactant include certain of the commercially available TetronicT compounds, marketed by BASF.
  • Nonionic alkylpolysaccharide surfactant include certain of the commercially available TetronicT 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
  • 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: R6CON(R7)2 wherein R ⁇ is an alkyl group containing from 7 to 21 , preferably from 9 to 17 carbon atoms and each R? is selected from the group consisting of hydrogen, C1-C4 alkyl, C1-C4 hydroxyalkyl, and -(C2H4 ⁇ ) x H, where x is in the range of from 1 to 3.
  • Preferred carrier materials are selected from nonionic ethoxylated alcohol surfactants.
  • the amine reaction product will be present in an amount of from 1 to 75%, preferably 10 to 60%, more preferably 15 to 45% by weight of the processed reaction product in the produced particle. In this instance, 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 carrier will be present in an amount of from 3 to 95%, preferably from 15 to 80% and most preferably from 25 to 75%, by weight of the produced particles in the processed amine reaction product.
  • Processing of the amine reaction product with the carrier is done by thoroughly mixing the amine reaction product with the carrier.
  • This mixing is done at the lowest possible temperature, i.e. just above the melting point of the carrier.
  • the mixing step is carried out until a complete homogeneous mixture is obtained.
  • homogeneous it is meant compositions which have similar appearance to the resulting composition of a 20g of amine reaction product mixed with 80g of TAE80 for 5 minutes by means of an Ultra Turrax , the temperature of mixing being of about 70°C.
  • a carrier with a melting point between 35 and 135°C it is then preferred to further process the mixture to form a coated particle like e.g. by adsorption of the mixture onto a solid, preferably porous coating.
  • the resulting coated particles can be in any form which is suitable for incorporation into liquid or powders, preferably powders, such as agglomerate, pellets, tablets, or mixtures thereof.
  • Suitable coating agents for both solid, including paste, and liquid mixture are substantially water-soluble solid binder or agglomerating agents.
  • 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 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, carbonates, bicarbonates, borates, phosphates, sulfate salts like sodium and magnesium sulfate, inorganic perhydrate salts including perborate like perborate monohydrate, percarbonate, silicates, starch, cyclodextrin, and mixtures of any of the foregoing.
  • 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.
  • 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 Si ⁇ 2: Na2 ⁇ 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.
  • Typical disclosure of cyclodextrin derivatives are disclosed in WO96/05358, 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
  • M is sodium or hydrogen
  • x is a number from 1.9 to 4
  • y is a number from 0 to 20.
  • EP-A-0164514 and methods for their preparation are disclosed in DE-A-
  • x in the general formula above has a value of 2, 3 or 4 and is preferably 2.
  • the most preferred material is 5-Na2Si2 ⁇ 5, available from Hoechst AG as NaSKS-6.
  • Suitable aluminosilicate zeolites have the unit cell formula Na z [(Al ⁇ 2)z(Si ⁇ 2)y].
  • XH2O 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
  • Zeolite X has the formula Nas ⁇ [(AIO 2 )86(Si ⁇ 2)l06l- 276 H 2 O.
  • the amine reaction product when the amine reaction product is mixed with a carrier and further processed to form a coated particle, the amine reaction product will be present in an amount of from 1 to 75%, preferably 5 to 30%, more preferably 6 to 25% 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 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 take 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, 150g of a mixture containing TAE80 and 20% of the amine reaction product is poured at 60°C into a Braun Mixer containing 300g 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 65°C. The agglomerated particle can then be used as is for incorporation into the finished composition.
  • the coated particle may also contain one or more additional ingredients like a surfactant for improved solubility or dispersability.
  • a surfactant for improved solubility or dispersability.
  • Typical of such surfactant are the anionic, nonionic, or cationic surfactants, a cationic, anion or non-ionic surfactant like.
  • the weight ratio of such additional ingredient(s) to the coating agent is of up to 1 :1.
  • an additional coating on the coated particle can be provided, which depending on the nature of this additional coating will give improved storage stability, flowability and/or improved fabric substantivity of the coated particle.
  • One typical example is polyvinyl alcohol.
  • the finished compositions aspect of the invention comprises the incorporation of the hereinbefore described processed amine reaction product together with one or more laundry or cleaning ingredient in a finished composition.
  • the incorporation of the processed amine reaction product is conveniently made depending on its end form by either by spraying when in sprayable liquid form, or dry-addition when 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.
  • compositions incorporating the processed amine reaction product will normally contain from 0.1 to 25%, more preferably from 0.2 to 10%, and most preferably from 0.5 to 5% of the processed product on a composition weight basis.
  • 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 anti- redeposition agents, suds suppressors, enzymes, fluorescent whitening agents, photoactivated bleaches, perfumes, colours, clay softening agent, effervescent, and mixtures thereof.
  • surfactants organic and inorganic builders, soil suspending and anti- redeposition agents, suds suppressors, enzymes, fluorescent whitening agents, photoactivated bleaches, perfumes, colours, clay softening agent, effervescent, and mixtures thereof.
  • Typical disclosure of such components can be found in EP-A-0,659,876 and European patent application No. 98870226.2 which are both incorporated herein by reference.
  • 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. Where present as such components, 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.
  • European Patents No.s 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. C6H 8 0 7 + 3NaHC ⁇ 3 Na ⁇ CeHsOy + 3C0 2 + 3H2O
  • 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
  • Other preferred optional ingredients include enzyme stabilisers, polymeric soil release agents, materials effective for inhibiting the transfer of dyes from one fabric to another during the cleaning process (i.e., dye transfer inhibiting agents), polymeric dispersing agents, suds suppressors, optical brighteners or other brightening or whitening agents, anti-static agents, other active ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations and solid fillers for bar compositions.
  • enzyme stabilisers materials effective for inhibiting the transfer of dyes from one fabric to another during the cleaning process (i.e., dye transfer inhibiting agents), polymeric dispersing agents, suds suppressors, optical brighteners or other brightening or whitening agents, anti-static agents, other active ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations and solid fillers for bar compositions.
  • 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.
  • the package is a dispensing means. Typical disclosure of such spray dispenser can be found in WO 96/04940 page 19 line 21 to page 22 line 27.
  • 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 perfume 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 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 G100 was dried using the following procedure: 20 g of the Lupasol solution was dried at the rotating evaporator during several hours. The obtained residue, still containing about 4.5 g of H 2 O, was azeotropically distilled at the rotating evaporator using toluene. The residue was then placed in the desiccator dried at 60 °C (using P 2 0 5 as water absorbing material). On basis of the obtained weight we concluded that the oil contained less then 10 % H 2 0. On basis of the NMR-spectra we concluded that this is probably less then 5 %. This dried sample was then used in the preparation of ⁇ -amino ketones.
  • amine reaction product is processed as hereinbefore described.
  • 20g of amine reaction product as above synthesised is mixed in an Ultra Turrax containing 80g of carrier, e.g. TAE80 for 5 minutes, the temperature of mixing being of about 70°C, and the speed of the mixer being sufficient so as to maintain such temperature substantially constant. Temperature and time will depend on the nature of the carrier but are a conventional step to skilled man.
  • the resulting mixture is maintained at a temperature substantially equal to the melting point of the carrier material. Once the mixture is at a suitable temperature, it is poured onto the coating material and agglomerated in an electrical mixer like a Braun Mixer. Care is also taken that the temperature during the mixing does not substantially exceed the melting point of the carrier material.
  • DEQA Di-(tallowyl-oxy-ethyl) dimethyl ammonium chloride
  • DTDMAC Ditallow dimethylammonium chloride
  • DEQA (2) Di-(soft-tallowyloxyethyl) hydroxyethyl methyl ammonium methylsulfate.
  • DTDMAMS Ditallow dimethyl ammonium methylsulfate. SDASA 1 :2 ratio of stearyldimethyl amine:triple-pressed stearic acid.
  • PEI Polyethyleneimine with an average molecular weight of 1800 and an average ethoxylation degree of 7 ethyleneoxy residues per nitrogen
  • STPP Anhydrous sodium tripolyphosphate TSPP Tetrasodium pyrophosphate Zeolite A Hydrated sodium aluminosilicate of formula Na-
  • Citric acid Anhydrous citric acid
  • Bicarbonate Anhydrous sodium bicarbonate with a particle size distribution between 400 ⁇ m and 1200 ⁇ m
  • MA/AA Copolymer of 4:6 maleic/acrylic acid, average molecular weight about 10,000
  • Protease I Proteolytic enzyme, having 4% by weight of active enzyme, as described in WO 95/10591 , sold by
  • Alcalase Proteolytic enzyme having 5.3% by weight of active enzyme, sold by NOVO Industries A S Cellulase Cellulytic enzyme, having 0.23% by weight of active enzyme, sold by NOVO Industries A/S under the tradename Carezyme
  • Amylase Amylolytic enzyme having 1.6% by weight of active enzyme, sold by NOVO Industries A/S under the tradename Termamyl 120T
  • Lipase Lipolytic enzyme having 2.0% by weight of active enzyme, sold by NOVO Industries A/S under the tradename Lipolase
  • Lipolytic enzyme having 2.0% by weight of active enzyme, sold by NOVO Industries A/S under the tradename Lipolase Ultra
  • Endolase Endoglucanase enzyme having 1.5% by weight of active enzyme, sold by NOVO Industries A/S
  • NAC-OBS (6-nonamidocaproyl) oxybenzene sulfonate
  • TAED Tetraacetylethylenediamine DTPA
  • DTPMP Diethylene triamine penta (methylene phosphonate), marketed by Monsanto under the Tradename
  • Dequest 2060 Ethylenediamine-N,N'-disuccinic acid, (S,S) isomer in the form of its sodium salt.
  • Photoactivated Sulfonated zinc phthlocyanine encapsulated in bleach (1) dextrin soluble polymer Photoactivated Sulfonated alumino phthlocyanine encapsulated in bleach (2) dextrin soluble polymer Brightener 1 Disodium 4,4'-bis(2-sulphostyryl)biphenyl Brightener 2 Disodium 4,4'-bis(4-anilino-6-morpholino-1.3.5- triazin-2-yl)amino) stilbene-2:2'-disulfonate
  • PEO Polyethylene oxide with an average molecular weight of 50,000
  • PVNO Polyvinylpyridine N-oxide polymer with an average molecular weight of 50,000
  • PEI Polyethyleneimine with an average molecular weight of 1800 and an average ethoxylation degree of 7 ethyleneoxy residues per nitrogen
  • Opacifier Water based monostyrene latex mixture, sold by
  • Wax Paraffin wax PA30 Polyacrylic acid of average molecular weight of between about 4,500 - 8,000.
  • Polygel/carbopol High molecular weight crosslinked polyacrylates High molecular weight crosslinked polyacrylates.
  • 3 -C-]5 mixed ethoxylated/propoxylated fatty alcohol with an average degree of ethoxylation of 3.8 and an average degree of propoxylation of 4.5.
  • Neodol 45-13 C14-C15 linear primary alcohol ethoxylate sold by Shell
  • MnTACN Manganese 1 ,4,7-trimethyl-1 ,4,7-triazacyclononane.
  • PAAC Pentaamine acetate cobalt(lll) salt PAAC Pentaamine acetate cobalt(lll) salt.
  • PARP1 Processed amine reaction product of ethyl 4- aminobenzoate with 2,4-dimethyl-3-cyclohexen-1- carboxaldehyde as made from Synthesis example I, mixed with TAE80 carrier and agglomerated with a coating agent according to processing method above described.
  • PARP2 Processed amine reaction product of Lupasol G35 with ⁇ -Damascone as made from Synthesis example III, mixed with TAE100 carrier and agglomerated with a coating agent according to processing method above described.
  • PARP3 Processed amine reaction product of Lupasol HF with ⁇ - Damascone as made from Synthesis example III, mixed with TAE80 carrier and agglomerated with a coating agent according to processing method above described.
  • PARP4 Processed amine reaction product of BNPP with ⁇ - Damascone as made from Synthesis example II, mixed with PEG4000 carrier and agglomerated with a coating agent according to processing method above described.
  • PARP5 Processed amine reaction product of LupasolGIOO with 2,4-dimethyl-3-cyclohexen-1 -carboxaldehyde as made from Synthesis example III, mixed with a TAE80 carrier and agglomerated with a coating agent according to processing method above described.
  • PARP6 Processed amine reaction product of ethyl 4- aminobenzoate with trans-2-nonenal as made from Synthesis example I, mixed with a TAE80 carrier and agglomerated with a coating agent according to processing method above described.
  • PARP7 Processed amine reaction product of ethyl 4- aminobenzoate with trans-2-hexenal as made from Synthesis example I, mixed with TAE80 carrier and agglomerated with a coating agent according to processing method above described.
  • Flocculating agent II polyethylene oxide of average molecular weight of between 400,000 and 1 ,000,000
  • Flocculating agent III polymer of acrylamide and/ or acrylic acid of average molecular weight of 200,000 and 400,000
  • DOBS Decanoyl oxybenzene sulfonate in the form of the sodium salt
  • Fabric softener active Di-(canoloyl-oxy-ethyl)hydroxyethyl methyl ammonium methylsulfate
  • Genapol V4463 Coco alcohol ethoxylated with 10 moles ethylene oxide and commercially available from Clariant
  • Silwet 7604 Polyalkyleneoxide polysiloxanes of MW 4000 of formula
  • Silwet 7600 Polyalkyleneoxide polysiloxanes of MW 4000, of formula
  • liquid detergent formulations were prepared in accord with the invention (levels are given as parts per weight).
  • liquid detergent formulations were prepared in accord with the invention (levels are given in parts per weig ht) :
  • liquid detergent compositions were prepared in accord with the invention (levels are given in parts per weight).
  • composition in the form of a tablet, bar, extrudate or granule in accord with the invention is a composition in the form of a tablet, bar, extrudate or granule in accord with the invention
  • laundry bar detergent compositions were prepared in accord with the invention (levels are given in parts per weight).
  • Nonionic 1.2 1.0 0.7 0.8 1.9 0.7 0.6 0.3
  • the following tablet detergent compositions were prepared according to the present invention by compression of a granular dishwashing detergent composition at a pressure of 13KN/cm2 using a standard 12 head rotary press:
  • Nonionic 1.5 2.0 1.5 1.65 0.8 6.3 PAAC - - 0.02 0.009
  • liquid dishwashing detergent compositions of density 1.40Kg/L were prepared according to the present invention :
  • liquid rinse aid compositions were prepared according to the present invention : A B C
  • liquid dishwashing compositions were prepared according to the present invention :
  • liquid hard surface cleaning compositions were prepared according to the present invention :
  • lavatory cleansing block compositions were prepared according to the present invention.
  • the following toilet bowl cleaning composition was prepared according to the present invention.
  • Example 28 The following are non-limiting examples of 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:

Abstract

L'invention concerne un procédé servant à préparer des particules d'un produit de réaction d'amine au moyen d'un support dont le point de fusion est situé entre 30 °C et 135 °C, ce qui est éventuellement suivi par une étape de revêtement. Elle concerne également des produits de réaction d'amine traités et des compositions finies incorporant ce produit traité.
PCT/US1999/015679 1998-07-10 1999-07-12 Procede servant a preparer des particules de produit de reaction d'amine WO2000002986A2 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
JP2000559208A JP2002524573A (ja) 1998-07-10 1999-07-12 アミン反応生成物の粒子の製造方法
BRPI9912023-2A BR9912023B1 (pt) 1998-07-10 1999-07-12 processo para a fabricaÇço de partÍculas de produto de reaÇço de amina, produto de reaÇço de amina processada, mÉtodo de incorporaÇço da mesma, composiÇço final, mÉtodo para distribuiÇço de fragrÂncia residual a uma superfÍcie, uso de produto e composiÇço acondicionada.
AT99932389T ATE286962T1 (de) 1998-07-10 1999-07-12 Verfahren zur herstellung von aminierungsprodukte-teilchen
EP99932389A EP1144578B1 (fr) 1998-07-10 1999-07-12 Procede servant a preparer des particules de produit de reaction d'amine
AU48703/99A AU4870399A (en) 1998-07-10 1999-07-12 Process for producing particles of amine reaction product
CA002335576A CA2335576C (fr) 1998-07-10 1999-07-12 Procede servant a preparer des particules de produit de reaction d'amine
ES99932389T ES2237123T3 (es) 1998-07-10 1999-07-12 Proceso para fabricar particulas de producto de reaccion de amina.
US09/720,401 US6451751B1 (en) 1998-07-10 1999-07-12 Process for producing particles of amine reaction product
DE69923227T DE69923227T2 (de) 1998-07-10 1999-07-12 Verfahren zur Herstellung von Aminierungsprodukt-Teilchen

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
EP98870155.3 1998-07-10
EP98870156 1998-07-10
EP98870156.1 1998-07-10
EP98870155 1998-10-28
EP98870226.2 1998-10-28
EP98870227A EP0971025A1 (fr) 1998-07-10 1998-10-28 Produits de réaction d'aminé comprenant un ou plusieurs principes actifs
EP98870226A EP0971024A1 (fr) 1998-07-10 1998-10-28 Compositions de blanchissage et de lavage
EP98870227.0 1998-10-28
EP99870026A EP0971027A1 (fr) 1998-07-10 1999-02-11 Produits de réaction d'aminé comprenant un ou plusieurs ingrédients actifs
EP99870025.6 1999-02-11
EP99870025A EP0971026A1 (fr) 1998-07-10 1999-02-11 Compositions de lavage et de nettoyage
EP99870026.4 1999-02-11
EP99870029.8 1999-02-15
EP99870029A EP0971021A1 (fr) 1998-07-10 1999-02-15 Procédé de production de particules de produit de réaction aminé

Publications (2)

Publication Number Publication Date
WO2000002986A2 true WO2000002986A2 (fr) 2000-01-20
WO2000002986A3 WO2000002986A3 (fr) 2001-08-02

Family

ID=27562215

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/015679 WO2000002986A2 (fr) 1998-07-10 1999-07-12 Procede servant a preparer des particules de produit de reaction d'amine

Country Status (11)

Country Link
EP (2) EP0971021A1 (fr)
JP (1) JP2002524573A (fr)
CN (1) CN1167780C (fr)
AR (1) AR019367A1 (fr)
AT (1) ATE286962T1 (fr)
AU (1) AU4870399A (fr)
BR (1) BR9912023B1 (fr)
CA (1) CA2335576C (fr)
DE (1) DE69923227T2 (fr)
ES (1) ES2237123T3 (fr)
WO (1) WO2000002986A2 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6916769B2 (en) 2001-12-03 2005-07-12 The Procter & Gamble Company Fabric treatment composition
WO2006010087A1 (fr) 2004-07-09 2006-01-26 The Procter & Gamble Company Rouleau présentant des avantages pour le tissu
EP1760142A1 (fr) 2005-09-02 2007-03-07 The Procter and Gamble Company Personnalisation du parfum des lessives
EP1992680A2 (fr) 2001-09-06 2008-11-19 The Procter and Gamble Company Bougies parfumées
US7569529B2 (en) 2005-09-07 2009-08-04 The Procter & Gamble Company Method of using fabric care compositions to achieve a synergistic odor benefit
JP2010031285A (ja) * 2001-10-19 2010-02-12 Procter & Gamble Co 有益剤デリバリーシステム
WO2011002872A1 (fr) 2009-06-30 2011-01-06 The Procter & Gamble Company Composition de conditionnement de tissu à multiples utilisations avec aminosilicone
WO2011005816A1 (fr) 2009-07-09 2011-01-13 The Procter & Gamble Company Procédé de préparation de particules de parfum
US11344493B2 (en) 2017-01-23 2022-05-31 Firmenich Sa Cleavable surfactant

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6319507B1 (en) * 1997-05-02 2001-11-20 Kobo Products, Inc. Agar gel bead composition and method
JP4410322B2 (ja) * 1998-08-05 2010-02-03 クミアイ化学工業株式会社 無水硫酸ナトリウム含有粒状組成物およびその製造法
US6740713B1 (en) 1999-07-08 2004-05-25 Procter & Gamble Company Process for producing particles of amine reaction products
US6764986B1 (en) 1999-07-08 2004-07-20 Procter & Gamble Company Process for producing particles of amine reaction products
US6972276B1 (en) 1999-07-09 2005-12-06 Procter & Gamble Company Process for making amine compounds
US6559116B1 (en) 1999-09-27 2003-05-06 The Procter & Gamble Company Antimicrobial compositions for hard surfaces
US6906012B1 (en) 1999-11-09 2005-06-14 Procter & Gamble Company Detergent compositions comprising a fragrant reaction product
ES2250225T3 (es) 1999-12-22 2006-04-16 THE PROCTER & GAMBLE COMPANY Proceso para fabricar un producto detergente.
JP4537545B2 (ja) * 2000-07-12 2010-09-01 花王株式会社 化粧料
EP1192885A1 (fr) 2000-10-02 2002-04-03 The Procter & Gamble Company Drap jetable perméable à la vapeur d'eau, imperméable aux liquides et contenant des agents actifs pour articles de literie
US7365043B2 (en) * 2003-06-27 2008-04-29 The Procter & Gamble Co. Lipophilic fluid cleaning compositions capable of delivering scent
MX2009007714A (es) * 2007-01-30 2009-12-14 Firmenich & Cie Liberacion controlada de aldehidos y cetonas activos de mezclas dinamicas equilibradas.
DE102007012910A1 (de) 2007-03-19 2008-09-25 Momentive Performance Materials Gmbh Mit Duftstoffen modifizierte, verzweigte Polyorganosiloxane
DE102007012909A1 (de) 2007-03-19 2008-09-25 Momentive Performance Materials Gmbh Mit Duftstoffen modifizierte, reaktive Polyorganosiloxane
US8557262B2 (en) 2008-09-12 2013-10-15 Firmenich Sa Divinyl ether derivatives capable of releasing active aldehydes and ketones and methods of use for perfuming surfaces
JP2012506414A (ja) 2008-10-21 2012-03-15 フイルメニツヒ ソシエテ アノニム 芳香組成物およびその使用
WO2010146556A2 (fr) 2009-06-19 2010-12-23 Firmenich Sa Compositions contre les mauvaises odeurs et procédé pour leur utilisation pour lutter contre des mauvaises odeurs de sueur
EP2270124A1 (fr) * 2009-06-30 2011-01-05 The Procter & Gamble Company Compositions de blanchiment comportant un système de livraison de parfum
EP2380959A1 (fr) * 2010-04-19 2011-10-26 The Procter & Gamble Company Composition détergente solide comprenant de la bêta cyclodextrine
EP2579839B1 (fr) 2010-06-10 2016-01-13 Firmenich SA Compositions de parfums et leurs utilisations
US9296978B2 (en) 2011-10-27 2016-03-29 Firmenich Sa Perfuming compositions and uses thereof
JP6223986B2 (ja) 2011-11-04 2017-11-01 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ 香料組成物及びそれらの使用
CN105102600A (zh) * 2013-03-28 2015-11-25 宝洁公司 包含聚醚胺、去垢性聚合物和羧甲基纤维素的清洁组合物
CN109336777A (zh) * 2018-11-19 2019-02-15 潍坊医学院 一种碘催化生成β-氨基酮类化合物的方法
WO2020260598A1 (fr) 2019-06-27 2020-12-30 Firmenich Sa Produits de consommation parfumés
CN110839629A (zh) * 2019-09-05 2020-02-28 中国计量大学 一种瓜果蔬菜高效抗菌杀菌剂制备方法及其应用
JP7421920B2 (ja) 2019-12-17 2024-01-25 花王株式会社 繊維製品用洗浄剤組成物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0041328A1 (fr) * 1980-05-16 1981-12-09 Unilever Plc Procédé de déposition de parfum sur des matières textiles et le produit utilisé ainsi
EP0430315A2 (fr) * 1989-09-29 1991-06-05 Unilever N.V. Compositions détegentes parfumées
USH1468H (en) * 1994-04-28 1995-08-01 Costa Jill B Detergent compositions containing cellulase enzyme and selected perfumes for improved odor and stability
WO1998008925A1 (fr) * 1996-08-26 1998-03-05 The Procter & Gamble Company Procede d'agglomeration permettant de produire des compositions detergentes et consistant a effectuer le melange prealable de polymeres de polyamines modifiees
EP0831143A1 (fr) * 1996-09-19 1998-03-25 The Procter & Gamble Company Composé polymérique contenant un ou plus alcools actifs

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0041328A1 (fr) * 1980-05-16 1981-12-09 Unilever Plc Procédé de déposition de parfum sur des matières textiles et le produit utilisé ainsi
EP0430315A2 (fr) * 1989-09-29 1991-06-05 Unilever N.V. Compositions détegentes parfumées
USH1468H (en) * 1994-04-28 1995-08-01 Costa Jill B Detergent compositions containing cellulase enzyme and selected perfumes for improved odor and stability
WO1998008925A1 (fr) * 1996-08-26 1998-03-05 The Procter & Gamble Company Procede d'agglomeration permettant de produire des compositions detergentes et consistant a effectuer le melange prealable de polymeres de polyamines modifiees
EP0831143A1 (fr) * 1996-09-19 1998-03-25 The Procter & Gamble Company Composé polymérique contenant un ou plus alcools actifs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KAMOGAWA H ET AL: "Chemical release control- Schiff bases of perfume aldehydes and aminostyrenes" JOURNAL OF POLYMER SCIENCE, POLYMER CHEMISTRY EDITION, vol. 20, 1 January 1982 (1982-01-01), pages 3121-3129, XP002084908 ISSN: 0887-624X *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1992680A2 (fr) 2001-09-06 2008-11-19 The Procter and Gamble Company Bougies parfumées
JP2010031285A (ja) * 2001-10-19 2010-02-12 Procter & Gamble Co 有益剤デリバリーシステム
US6916769B2 (en) 2001-12-03 2005-07-12 The Procter & Gamble Company Fabric treatment composition
WO2006010087A1 (fr) 2004-07-09 2006-01-26 The Procter & Gamble Company Rouleau présentant des avantages pour le tissu
EP1760142A1 (fr) 2005-09-02 2007-03-07 The Procter and Gamble Company Personnalisation du parfum des lessives
US7569529B2 (en) 2005-09-07 2009-08-04 The Procter & Gamble Company Method of using fabric care compositions to achieve a synergistic odor benefit
WO2011002872A1 (fr) 2009-06-30 2011-01-06 The Procter & Gamble Company Composition de conditionnement de tissu à multiples utilisations avec aminosilicone
WO2011005816A1 (fr) 2009-07-09 2011-01-13 The Procter & Gamble Company Procédé de préparation de particules de parfum
US8273699B2 (en) 2009-07-09 2012-09-25 The Procter & Gamble Company Process for preparing a perfume particle
US11344493B2 (en) 2017-01-23 2022-05-31 Firmenich Sa Cleavable surfactant

Also Published As

Publication number Publication date
DE69923227D1 (de) 2005-02-17
JP2002524573A (ja) 2002-08-06
BR9912023A (pt) 2001-04-03
WO2000002986A3 (fr) 2001-08-02
EP1144578B1 (fr) 2005-01-12
ES2237123T3 (es) 2005-07-16
BR9912023B1 (pt) 2008-11-18
AR019367A1 (es) 2002-02-13
ATE286962T1 (de) 2005-01-15
AU4870399A (en) 2000-02-01
CA2335576C (fr) 2007-04-10
CN1167780C (zh) 2004-09-22
CA2335576A1 (fr) 2000-01-20
DE69923227T2 (de) 2006-01-05
CN1334858A (zh) 2002-02-06
EP0971021A1 (fr) 2000-01-12
EP1144578A2 (fr) 2001-10-17

Similar Documents

Publication Publication Date Title
EP1144578B1 (fr) Procede servant a preparer des particules de produit de reaction d'amine
US7601681B2 (en) Laundry and cleaning and/or fabric care composition
US6451751B1 (en) Process for producing particles of amine reaction product
US6764986B1 (en) Process for producing particles of amine reaction products
US6740713B1 (en) Process for producing particles of amine reaction products
US20030228992A1 (en) Laundry and cleaning and/or fabric care compositions
EP1067174B1 (fr) Procédé de production de particules de produit de réaction d'amine
EP1144566B1 (fr) Compositions de lessive et de nettoyage
EP1123376B1 (fr) Compositions de lessive et de nettoyage
US20040147426A1 (en) Laundry and cleaning compositions
US6972276B1 (en) Process for making amine compounds
WO2001004084A1 (fr) Procede de production de composes a fonction amine
WO2001004247A1 (fr) Production de particules d'un produit de reaction amine
EP1067117A1 (fr) Procédé de préparation de composés imines
MXPA01000297A (en) Process for producing particles of amine reaction product

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 99808508.1

Country of ref document: CN

AK Designated states

Kind code of ref document: A2

Designated state(s): AE AL AM AT AT AU AZ BA BB BG BR BY CA CH CN CU CZ CZ DE DE DK DK EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: IN/PCT/2000/00335/DE

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 09720401

Country of ref document: US

ENP Entry into the national phase

Ref document number: 2335576

Country of ref document: CA

ENP Entry into the national phase

Ref document number: 2000 559208

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: PA/a/2001/000297

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 1999932389

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

AK Designated states

Kind code of ref document: A3

Designated state(s): AE AL AM AT AT AU AZ BA BB BG BR BY CA CH CN CU CZ CZ DE DE DK DK EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

WWP Wipo information: published in national office

Ref document number: 1999932389

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1999932389

Country of ref document: EP