WO2013068384A2 - Emulsions containing polymeric cationic emulsifiers, substance and process - Google Patents

Emulsions containing polymeric cationic emulsifiers, substance and process Download PDF

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Publication number
WO2013068384A2
WO2013068384A2 PCT/EP2012/072004 EP2012072004W WO2013068384A2 WO 2013068384 A2 WO2013068384 A2 WO 2013068384A2 EP 2012072004 W EP2012072004 W EP 2012072004W WO 2013068384 A2 WO2013068384 A2 WO 2013068384A2
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weight
amount
emulsion
oil
monomers
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PCT/EP2012/072004
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English (en)
French (fr)
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WO2013068384A3 (en
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Rainer Dobrawa
Dieter Boeckh
Aaron FLORES-FIGUEROA
Markus Brym
Rajan K. Panandiker
Frank Huelskoetter
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Basf Se
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Priority to BR112014010971A priority Critical patent/BR112014010971A2/pt
Priority to EP12783986.8A priority patent/EP2776149A2/en
Priority to CN201280055087.1A priority patent/CN103930194B/zh
Priority to JP2014540430A priority patent/JP2015507520A/ja
Priority to CA2850271A priority patent/CA2850271A1/en
Priority to KR1020147015673A priority patent/KR20140093264A/ko
Priority to RU2014123613/04A priority patent/RU2014123613A/ru
Priority to IN3626CHN2014 priority patent/IN2014CN03626A/en
Priority to MX2014004773A priority patent/MX2014004773A/es
Publication of WO2013068384A2 publication Critical patent/WO2013068384A2/en
Publication of WO2013068384A3 publication Critical patent/WO2013068384A3/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
    • C08F226/04—Diallylamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111—Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate

Definitions

  • the present invention is directed to stable emulsions comprising oils and a polymeric cationic emulsifier, the process to obtain said emulsions and the use of said emulsions.
  • Oils such as silicone oils, natural oils, polyolefines and in particular polyisobutene are useful ingredients in a lot of technical applications. It is, however, still difficult to obtain stable emulsions comprising such oil(s) and water. There is always a need to add either surfactants or huge amounts of additional polymer.
  • PCT/EP201 1/057586 discloses an emulsion comprising (a) polyolefines such as polyisobutene, polymers Px which are copolymers of non ionic, anionic or pseudocationic monomers and water.
  • DE 195 05 100 A1 relates to the preparation of polymers which are the product of the polymerization of bisesters of akyl-or alkenyl carboxylic acid derivatives and polyal- cohols. These polymers are used as solubilisers, emulsifiers and cleaning compounds.
  • WO 2007/042454 A1 describes the use of terpolymers of (a) maleic anhydride, (b) isobutylene and (c) polyisobutylene for producing aqueous emulsions or dispersions of hydrophobic substances such as silicones.
  • WO 2007/014915 writes on aqueous dispersions comprising (A) a polymer such as polyisobutene and (B) an emulsifier obtained by the polymerization of isobutylene, ma- leic anhydride and polyethyleneglycol. This dispersion is used for the treatment of leather or as additive in construction chemicals.
  • EP 0 995 791 A1 discloses a polymer formed by copolymerizing two or more monomers A, B and C, wherein A is selected from one or more C3-C8 monoethylenically unsaturated carboxylic acid moieties, B can be a C3-C60 alkyl(meth)acrylate and C is an ethylenically unsaturated monomer which is copolymerizable with monomers A and B.
  • the polymer is used in solid form or liquid form, as an aqueous or co-solvent based solution, to promote the release of oily soil from fabrics.
  • additive(s) Ax in an amount of from 0 to 20 weight%
  • the emulsion can consist of components a), b) and e), in which case the amounts add up to 100 weight%, - such an emulsion forms a preferred embodiment of the present invention.
  • the emulsion can also contain components a), b) and e) as well as additional components.
  • Emulsions, which in addition to components a), b) and e) also contain components c) and/or d) form one preferred embodiment of the invention.
  • the inventive emulsion may also contain other components.
  • additive(s) Ax in an amount of from 0.1 to 15 weight%
  • additive(s) Ax in an amount of from 1 to 10 weight%
  • emulsion wherein the components of the emulsion independently of each other are present in amounts of:
  • emulsions are those, which comprise: a) oil(s) in an amount of from 15 to 35 weight%,
  • polymeric cationic emulsifiers Px in an amount of from 0,5 to 10 weight%
  • surfactant(s) Sx in an amount of from 4 to 12 weight%
  • additive(s) Ax in an amount of from 0 to 10 weight% and e) water in an amount of from 33 to 80,5 weight%,
  • polymeric cationic emulsifiers Px in an amount of from 0,5 to 10 weight%
  • surfactant(s) Sx in an amount of from 4 to 12 weight%
  • additive(s) Ax in an amount of 0 weight%
  • polymeric cationic emulsifiers Px in an amount of from 0,5 to 10 weight%
  • surfactant(s) Sx in an amount of from 4 to 12 weight%
  • additive(s) Ax in an amount of 0 weight%
  • polymeric cationic emulsifiers Px in an amount of from 0,5 to 30 weight%
  • surfactant(s) Sx in an amount of 0 weight%
  • additive(s) Ax in an amount of from 2 to 8 weight%
  • polymeric cationic emulsifiers Px in an amount of from 0,5 to 5 weight%
  • surfactant(s) Sx in an amount of 0 weight %
  • additive(s) Ax in an amount of 0 weight %
  • the oil(s) used in the present invention is/are selected from the group consisting of: a1 ) polyolefines,
  • mineral oils having a boiling point at atmospheric pressure of 150 °C or higher, a5) esters of C10- to C26-carboxylic acid with C8 - C24-alcohols, and/or mixtures thereof.
  • Oils according to the invention refer to hydrophobic substances, which are liquid at ambient temperature.
  • polyolefine(s) as used in the present invention is/are a chemical compound ⁇ ) consisting of carbon and hydrogen atoms.
  • the polyolefine(s) can be linear, e.g. polyethylene, or can have side chains, e.g. polypropylene having methyl-side chains, which side chains may be that long that comb-like structures are found, or can be co- or ter-polymers, e.g. ethene/propene-copolymer or ethane/propene/hexane- terpolymer. It is particularly preferred, when the polyolefine(s) is/are substantially ho- mopolymers, i.e.
  • the degree of co- or ter-monomer is below 10 mass%, preferably below 5 mass% based on the mass of the polymer. It is particularly preferred, if the polymers) is/are homopolymers, i.e. they consist of only one kind of monomer.
  • an emulsion wherein the polyolefine(s) a1 ) is/are selected from the group consisting of: polyethylene, polypropylene, polybutylene and polyisobutylene is preferred.
  • the emulsion can comprise one or more polyolefine(s).
  • An emulsion, which only comprises one polyolefine a1 ) is preferred.
  • An emulsion, which only comprises poly- isobutylene as polyolefine a1 ) is particularly preferred.
  • the polyolefines a1 ) can be prepared by the usual procedures (Ullmann's Encyclopedia of Industrial Chemistry, Polyolefins, Whiteley, Heggs, Koch, Mawer, Immel, Wiley-VCH Verlag GmbH & Co.
  • the polyolefine(s) a1 ) preferably has/have of molar mass (Mn) of at least 250 g/mol, preferably at least 350 g/mol and more preferred at least 500 g/mol.
  • the polyolefine(s) a1 ) have a maximum molar mass Mn of 10.000 g/mol, preferably 5000 g/mol and more preferred of 2500 g/mol.
  • the most preferred range of the molar mass Mn of polyolefins a1 ) is from 550 to 2000 g/mol.
  • Suitable silicone oils a2) contained within the emulsion of the present invention are, for example, linear polydimethylsiloxanes,
  • poly(methylphenylsiloxanes), cyclic siloxanes and mixtures thereof are preferably in a range from about 1000 to 150 000 g/mol.
  • Preferred cyclic siloxanes have 4- to 8-membered rings. Suitable cyclic siloxanes are commercially available, for example, under the name cyclomethicone.
  • Preferred natural oils a3) contained within the emulsion of the present invention are, for example, castor oil, soya oil, peanut oil, olive oil, sunflower oil, sesame oil, avocado oil, cocoa butter, almond oil, peach kernel oil, ricinus oil, cod-liver oil, pig fat, spermaceti, spermaceti oil, sperm oil, wheatgerm oil, macadamia nut oil, evening primrose oil, jo- joba oil; fatty alcohols, such as lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, cetyl alcohol; fatty acids, such as myristic acid, stearic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid and saturated, unsaturated and substituted fatty acids different therefrom; and mixtures of the abovementioned oil and fat components.
  • castor oil soya oil, peanut oil, olive oil,
  • Preferred mineral oils a4) contained within the emulsion of the present invention available under the names mineral oil light, mineral oil heavy, paraffin liquid or Nujol, that are liquid at room temperature.
  • the emulsion according to the invention comprises polymer(s) PX, wherein Px is the product of the polymerization of
  • Monomer A is a cationic monoethylenically unsaturated monomer which is at least partially soluble in water of the reaction solvent.
  • Suitable examples of monomer A are (3- acrylamidopropyl)-trimethylammonium chloride (APT AC), diallyl dimethyl ammonium chloride (DADMAC), (3-methacrylamidopropyl)-trimethylammonium chloride (MAP- TAC), dimethylaminopropylacrylat methochlorid, dimethylaminopropylmethacrylat methochlorid,.
  • A is preferably DADMAC.
  • Monomer B is a linear or branched alkyl (meth)acrylate, preferably a C10-C30 al- kyl(meth)acrylate, even more preferably a C12-C20 alkyl(meth)acrylate.
  • Suitable monomers B include linear and branched alkyl esters of (meth)acrylic acid, such as octyl acrylate, dodecyl acrylate, lauryl acrylate, cetyl acrylate, octadecyl acrylate, isodecyl acrylate, 2-ethylhexyl acrylate.
  • Monomer B is preferably lauryl acrylate (LA).
  • Monomer C is a C3-C8 monoethylenically unsaturated mono- or dicarboxylic acid as well as the anhydrides and salts thereof. Suitable examples of monomer C include acrylic acid, methacrylic acid, crotonic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid and metal salts thereof. Monomer C is preferably acrylic acid (AA).
  • the polymer Px is the product of the polymerization of
  • the polymer Px is preferably the product of the polymerization of
  • surfactant(s) Sx is/are selected from the group consisting of: c1 ) nonionic surfactants,
  • Surfactants normally consist of a hydrophobic and a hydrophilic part.
  • the hydrophobic part normally has a chain length of 4 to 20 C-atoms, preferably 6 to 19 C- atoms and particularly preferred 8 to 18 C-atoms.
  • the functional unit of the hydrophobic group is generally an OH-group, whereby the alcohol can be linear or branched
  • the hydrophilic part generally consists substantially of alkoxylated units (e.g.
  • anionic surfactants are: carboxylates, sulfonates, sulfo fatty acid methyl- esters, sulfates, phosphates.
  • cationic surfactants are: quartery ammonium compounds.
  • betaine-surfactants are: alkyl betaines.
  • non-ionic compounds are: alcohol alkoxylates.
  • a Treatinglate is a compound, which comprises at least one carboxylate-group in the molecule.
  • carboxylates which can be used according to the present invention, are soaps— e.g. stearates, oleates, cocoates of alkali metals or of ammonium,
  • ethercarboxylates e.g. Akypo® RO 20, Akypo® RO 50, Akypo® RO 90.
  • a ..sulfonate is a compound, which comprises at least one sulfonate-group in the molecule.
  • sulfonates which can be used according to the invention, are alkyl benzene sulfonates— e.g. Lutensit® A-LBS, Lutensit® A-LBN, Lutensit® A-LBA, Marlon® AS3, Maranil® DBS,
  • alkyl sulfonates e.g. Alscoap OS-14P, BIO-TERGE® AS-40, BIO-TERGE® AS-40
  • sulfonated oils such as Turkish red oil
  • aromatic sulfonates e.g. Nekal® BX, Dowfax® 2A1.
  • a ..sulfo fatty acid methylester is a compound, having the following general formula (I):
  • R has 10 to 20 C-atoms; preferably 12 to 18 and particu-
  • a ..sulfate is a compound, which comprises at least one S04-group in the molecule.
  • sulfates which can be used according to the present invention, are fatty acid alcohol sulfates such as coco fatty alcohol sulfate (CAS 97375-27-4)— e.g. EMAL® 10G, Dispersogen® SI, Elfan® 280, Mackol® 100N,
  • coco fatty alcohol ethersulfates e.g. Emal® 20C, Latemul® E150, Sulfochem® ES-7, Texapon® ASV-70 Spec, Agnique SLES-229-F, Octosol 828, POLYSTEP® B-23, Unipol® 125-E, 130-E, Unipol® ES-40,
  • alcohol ethersulfates e.g. Avanel® S-150, Avanel® S 150 CG, Avanel® S 150 CG N, Witcolate® D51 -51 , Witcolate® D51 -53.
  • a ..phosphate is a compound, which comprises at least one P04-group.
  • alkyl ether phosphates e.g. Maphos® 37P, Maphos® 54P, Maphos® 37T, Maphos®
  • alkyl phosphates When producing the chemical composition of the present invention the anionic surfactants are preferably added as salts. Acceptable salts are e.g. alkali metal salts, such as sodium-, potassium- and lithium salts, and ammonium salts, such as hydroxyl ethylammonium-, di(hydroxy-ethyl)ammonium- und tri(hydroxyethyl)ammonium salts.
  • alkali metal salts such as sodium-, potassium- and lithium salts
  • ammonium salts such as hydroxyl ethylammonium-, di(hydroxy-ethyl)ammonium- und tri(hydroxyethyl)ammonium salts.
  • a group of the cationic surfactants are the quarternary ammonium compounds.
  • a deliberatelyquarternary ammonium compound is a compound, which comprises at least one R4N+-group per molecule. Examples of counter ions, which are useful in the quarternary ammonium compounds, are
  • halogens methosulfates, sulfates and carbonates of coco fat-, sebaceous fat- or cetyl/oleyltrimethylammonium.
  • Particularly suitable cationic surfactants are: - N,N-dimethyl-N-(hydroxy-C7-C25-alkyl)ammonium salts;
  • esterquats especially mono-, di- and trialkanolamines, quarternary esterified by C8-C22-carbonic acids;
  • R9 C1 -C25-alkyl or C2-C25-alkenyl
  • a Treatbetain-surfactant is a compound, which comprises under conditions of use - i.e. in the case of textile washing under normal pressure and at temperatures of from room temperature to 95 °C - at least one positive charge and at least one negative charge.
  • An instinctalkylbetain is a betain-surfactant, which comprises at least one alkyl-unit per molecule. Examples of betain-surfactants, which can be used according to the invention, are Cocamidopropylbetain— e.g.
  • Non-ionic surfactants are interfacially active substances having a head group, which is an uncharged, polar, hydrophilic group, not carrying a ionic charge at neutral pH, and which head group makes the non-ionic surfactant water soluble. Such a surfactant adsorbs at interfaces and aggregates to micelles above the critical micelle concentration (cmc).
  • the hydrophilic head group it can be distinguished between (oligo)oxyalkylene-groups, especially (oligo)oxyethylene-groups, (polyethyl- eneglycol-groups), including fatty alcohol polyglycole ether (fatty alcohol alkoxylates), alkylphenol polyglycolether and fatty acid ethoxylates, alkoxylated triglycerides and mixed ethers (polyethylene glycolether alcoxylated on both sides); and carbohydrate- groups, including e.g. alkyl polyglucosides and fatty acid-N-methylglucamides.
  • Alcohol alkoxylates are based on a hydrophobic part having a chain length of 4 to 20 C-atoms, preferably 6 to 19 C-atoms and particularly preferred 8 to 18 C-atoms, whereby the alcohol can be linear or branched, and a hydrophilic part, which can be alkoxylated units, e.g. ethylene oxide (EO), propylene oxide (PO) and/or butylene oxide (BuO), having 2 to 30 repeating units. Examples are besides others Lutensol ® XP,
  • Lutensol ® XL Lutensol ® ON, Lutensol ® AT, Lutensol ® A, Lutensol ⁇ AO, Lutensol ⁇ TO.
  • Alcoholphenolalkoxylat.es are compounds according to general formula (V),
  • Non-limiting examples of such compounds are: Norfox® OP-102, Surfonic® OP-120, T-Det® 0-12.
  • Fatty acid ethoxylates are fatty acid esters, which have been treated with different amounts of ethylene oxide (EO).
  • Triglycerides are esters of the glycerols (glycerides), in which all three hydroxy-groups have been esterified using fatty acids. These can be modified by alkylene oxides.
  • Fatty acid alkanol amides are compounds of general formula (VI)
  • R comprises 1 1 to 17 C-atoms and 1 ⁇ m + n ⁇ 5.
  • Alkylpolyglycosides are mixtures of alkylmonoglucosides (alkyl- a-d- and - ⁇ -d-gluco- pyranoside plus small amounts of -glucofuranoside), alkyldiglucosides (-isomaltosides, -maltosides and others) and alkyloligoglucosides (-maltotriosides, -tetraosides and others).
  • Alkylpolyglycosides are among other routes accessible by acid catalysed reaction (Fischer-reaction) from glucose (or starch) or from n-butylglucosides with fatty alcohols. Alkylpolyglycosides fit general formula (VII)
  • n 4 to 20.
  • Lutensol ® GD70 In the group of non-ionic N-alkylated, preferably N-methylated, fatty acid amides of general formula (VIII)
  • R1 is a n-C12-alkyl-moiety
  • R2 an alkyl-moiety having 1 to 8 C-atoms.
  • R2 preferably is methyl.
  • an emulsion wherein the additive(s) Ax is/are selected from the group consisting of: disinfectant, dye, acid, base, complexing agent, biocide, hydrotope, thickener, builder, cobuilder, enzyme, bleaching agent, bleach activator, bleaching catalyst, corrosion inhibitor, dye protection additive, dye transfer inhibitor, anti-greying agent, soil-release- polymer, fiber protection agent, silicon, bactericide, preserving agent, organic solvent, solubility adjustor, solubility enhancer, perfume gel formers, dyes, pigments, photopro- tective agents, consistency regulators, antioxidants, bleaches, care agents, tints, tan- ning agents, humectants, refatting agents, collagen, protein hydrolysates, lipids, emollients, softeners, antifoams, antistats, resins, solvents, solubility promoters, neutralizing agents, stabilizers, sterilizing agents, propellants, drying agents, opacifiers is preferred.
  • Disinfectants can be: oxidation agents, halogens such as chlorine and iodine and sub- stances, which release the same, alcohols such as ethanol, 1 -propanol and 2-propanol, aldehydes, phenoles, ethylene oxide, chlorohexidine and mecetroniummetilsulfate.
  • Pathogenic germs can be: bacteria, spores, fungi and viruses.
  • Dyes can be besides others: Acid Blue 9, Acid Yellow 3, Acid Yellow 23, Acid Yellow 73, Pigment Yellow 101 , Acid Green 1 , Acid Green 25.
  • Acids are compounds that can advantageously be used to solve or to avoid scaling.
  • Non-limiting examples of acids are formic acid, acetic acid, citric acid, hydrochloric a- cid, sulfuric acid and sulfonic acid.
  • Bases are compounds, which are useful for adjusting a preferable pH-range for complexing agents.
  • bases which can be used according to the present inven- tion, are: NaOH, KOH and amine ethanol.
  • crystalline and amorphous alumino silicates having ion exchanging properties such as zeolites: different types of zeolites are useful, especially those of type A, X, B, P, MAP and HS in their Na-modification or in modifications in which Na is partially substituted by other cat ions such as Li, K, Ca, Mg or ammonium;
  • crystalline silicates such as disilicates and layered-silicates, e.g. ⁇ - and ⁇ - Na2Si205.
  • the silicates can be used as alkali metal-, earth alkali metal- or ammonium salts, the Na-, Li- and Mg-silicates are preferred;
  • amorphous silicates such as sodium metasilicate and amorphous disilicate
  • carbonates and hydrogencarbonates These can be used as alkali metal-, earth alkali metal- or ammonium salts.
  • Na-, Li- and Mg-carbonates and -hydrogen carbonate, especially sodium carbonate and/or sodium hydrogen carbonate are preferred;
  • - polyphosphates such as pentanatriumtriphosphate.
  • Oligomeric and polymeric carbonic acids such as homopolymers of acrylic acid and aspartic acid, oligomaleic acid, copolymers of maleic acid and acrylic acid, methacrylic acid or C2-C22-olefines, e.g. isobutene or long chain a-olefines, vinyl-C1 -C8- alkylether, vinylacetate, vinylpropionate, (meth)acryl acid ester of C1 -C8-alcohols and styrene.
  • the oligomeric and polymeric carbonic acids preferably are used as acids or as sodium salts.
  • Chelating agents are compounds, which can bind cat ions. They can be used to reduce water hardness and to precipitate heavy metals. Examples of complexing agents are: NTA, EDTA, MGDA, DTPA, DTPMP, IDS, HEDP, ⁇ -ADA, GLDA, citric acid, oxodisuc- cinic acid and butanetetracarbonic acid.
  • the advantage of the use of these compounds lies in the fact that many compounds, which serve as cleaning agents, are more active in soft water. In addition to that scaling can be reduced or even be avoided. By using such compounds there is no need to dry a cleaned surface. This is an advantage in the work flow.
  • Useful anti greying agents are e.g. carboxymethylcellulose and graft polymers of vinyl acetate on polyethylene glycol.
  • Useful bleaching agents are e.g. adducts of hydrogenperoxide as inorganic salts, such as sodium perborate-monohydrate, sodium perborate-tetrahydrate and sodium carbo- nate-perhydrate, and percarbonic acids, such as phthalimidopercapronic acid.
  • bleach activators compounds such as ⁇ , ⁇ , ⁇ ', ⁇ '-tetraacetylethylendiamine (TAED), sodium-p-nonanoyloxybenzenesulfonate and N-methylmorpholiniumacetonitrilemethyl- sulfate are useful.
  • TAED ⁇ , ⁇ , ⁇ ', ⁇ '-tetraacetylethylendiamine
  • sodium-p-nonanoyloxybenzenesulfonate sodium-p-nonanoyloxybenzenesulfonate
  • N-methylmorpholiniumacetonitrilemethyl- sulfate N-methylmorpholiniumacetonitrilemethyl- sulfate
  • Useful enzymes are e.g. proteases, lipases, amylases, cellulases, mannanases, oxidases and peroxidases.
  • Useful as dye transfer inhibitors are e.g. homo-, co- and graft-polymers of 1 - vinylpyrrolidone, 1 -vinylimidazol or 4-vinylpyridine-N-oxide. Also homo- and copolymers of 4-vinylpyridin, which have been treated with chloro acetic acid are useful dye transfer inhibitors.
  • Biocides are compounds, which kill bacteria.
  • An example of a biocide is glutaric aldehyde.
  • the advantage of the use of biocides is that the spreading of pathogenic germs is counteracted.
  • Hydrotropes are compounds which enhance the solubility of the surfactant / the surfactants in the chemical composition.
  • An example is: Cumolsulfonate.
  • Thickeners are compounds, which enhance the viscosity of the chemical composition.
  • Non-limiting examples of thickeners are: polyacrylates and hydrophobically modified polyacrylates.
  • the advantage of the use of thickeners is, that liquids having a higher viscosity have a longer residence time on the surface to be treated in the cases this surface is inclined or even vertical. This leads to an enhanced time of interaction.
  • An emulsion which has a content of organic solvent below 50 mg/kg of emulsion is particularly preferred.
  • the stability of the emulsion is tested by visual inspection via the phase-stability-test. After preparation, the emulsion is stored in a closed graduated cylinder (Hirschmann Duran 100 ml volume, NS24/29) at room temperature without agitation. After 1 h, 4 h, 24 h and 48 h, the emulsion is inspected for phase separation.
  • a closed graduated cylinder Hirschmann Duran 100 ml volume, NS24/29
  • the emulsion is defined stable when no visually observable phase separation occurs after 48 h.
  • the emulsion is defined as re-emulsifiable when phase separation occurs after 48 h, but the emulsion is immediately reformed upon slight shaking or stirring with low shear, for example with a magnetic stirrer bar, and the reformed emulsion is stable again for at least four hours.
  • the emulsion is defined unstable, when phase separation occurs shortly after preparation and the emulsion can not be reformed by slight shaking or stirring with low shear, for example with a magnetic stir bar.
  • emulsions can be prepared by processes known in the literature, for example in Heusch, R., "Ullmann's Encyclopedia of Industrial Chemistry", Chapter “Emulsions", 1 - 47, Wiley-VCH, 2000 (DOI: 10.1002/14356007.a09_297) or in Kostansek, E.,
  • Suitable emulsifying machines are for example high-speed stirrers, agitation or impact machines, emulsifier centrifuges, colloid mills, metering pumps (atomizers), vibrators, ultrasonic generators and homogenizers.
  • the preparation of the emulsion is achieved via a solvent-free route (a solvent being a substance with a boiling point below 150 °C that can dissolve the oil(s) a), for example o-xylene) by combination of the compo- nents, comprising oil(s), polymer(s) Px, water, optionally surfactant, and optionally further additives such as defoamers etc., and homogenization with a suitable device, like for example a high-shear mixer or for example a high-pressure homogenizer, optionally at elevated temperatures.
  • a solvent being a substance with a boiling point below 150 °C that can dissolve the oil(s) a
  • the compo- nents comprising oil(s), polymer(s) Px, water, optionally surfactant, and optionally further additives such as defoamers etc.
  • a suitable device like for example a high-shear mixer or for example a high-pressure homogenizer, optionally at elevated temperatures.
  • the step of combining the components can vary: in one preferred embodiment, polymers) Px is dissolved in the oil(s), optionally additional components, and then combined with the water phase, comprising water, optionally surfactant and additional components. In another preferred embodiment, polymer(s) Px is dissolved in the water phase, comprising water, optionally surfactant and/or additional components, and then combined with the oil phase, comprising oil(s) and optionally additional components.
  • the preparation of the emulsion is achieved via a solvent route.
  • the components of the emulsion, comprising oil(s) a) and polymer(s) Px, are dissolved in a solvent, for example o-xylene, in a stirred reactor, optionally at elevated temperatures. After complete dissolution, water is added to the solution and the mixture is distilled, optionally under addition of water steam, at elevated temperature (above 80 °C) until the solvent is removed.
  • a solvent for example o-xylene
  • Low concentrated emulsions shall mean emulsions where the water content lies above 40 weight%, preferably in the range of from 45 weight% to 65 weight%, based on the total weight of the emulsion.
  • Highly concentrated emulsions shall mean emulsions where the water content lies below or is equal to 40 weight%, preferably in the range from 20 weight% to 35 weight%, based on the total weight of the emulsion.
  • the cleaning and/or treatment compositions of the present invention can be formulated into any suitable form and prepared by any process chosen by the formulator, non- limiting examples of which are described in U.S. 5,879,584; U.S. 5,691 ,297; U.S.
  • the K value of the polymers of the invention was determined in accordance with Fik- entscher (see H. Fikentscher, Cellulosechemie 13 (1932), 58 -64 and 71 -74) by measuring the viscosity of 0.1 % strength by weight solutions of the polymers in 3% strength by weight NaCI solution.
  • the solid content was determined by drying the aqueous solution of the polymer in an oven at 100°C, for 2 h, at reduced pressure (100 mbar).
  • Polymers P6 -P10 as well as Comparative Polymers CP1 and CP2 were prepared in a similar way as described in Example P1 , taking the monomers and the respective amounts given in Table 1 .
  • Polymers P2, P4, P5 and P1 1 were prepared in a similar way as described in Example P1 1 , taking the monomers and the respective amounts given in Table 1 .
  • Polyisobutene (PIB) (molecular weight 1000 g/mol) (17.5 parts per weight) and paraffin oil (17.5 parts per weight) were mixed and the mixture heated to 80 °C.
  • Polymer P1 (1 .75 parts per weight, calculated as active content) and nonionic surfactant C10-Guerbetalcohol alkoxylate (HLB 12.5, 8.8 parts per weight) were mixed with de-ionized water (54.4 parts per weight) and heated to 80 °C as well.
  • Example LC2 - LC12 The PIB/paraffin mixture was placed in a heated beaker and fitted with the Ultraturrax equipped with shear-head T50 and the speed was set to 5000 to 6000 rpm. At 80 °C the mixture of water, polymer and non-ionic surfactant was added and emulsified for 120 sec without further heating. A homogeneous emulsion that is stable against phase- separation for >1 week is formed.
  • Example LC2 - LC12 The PIB/paraffin mixture was placed in a heated beaker and fitted with the Ultraturrax equipped with shear-head T50 and the speed was set to 5000 to 6000 rpm. At 80 °C the mixture of water, polymer and non-ionic surfactant was added and emulsified for 120 sec without further heating. A homogeneous emulsion that is stable against phase- separation for >1 week is formed.
  • Example LC2 - LC12 The PIB/paraffin mixture was placed in a
  • Example LC1 The following examples were prepared in a similar way as described in Example LC1 , using the same quantities of the respective polymers P2 -P12.
  • the stability results are given in Table 2.
  • Emulsion stability is assessed by visual inspection after 2h, 3 days and 6 days, and an average is calculated. All emulsions were homogeneous and did not show phase separation. Some emulsions showed creaming after 3d or 6d. The degree of creaming is assessed and graded by visual inspection, with grade 1 being a perfectly homogeneous emulsion showing not signs of creaming, and grade 6 being an emulsion that is completely creamed. Nevertheless, all emulsions were stable against phase separation and a homogeneous emulsion could easily be reformed by shaking or stirring with a low shear magnetic stirrer.
  • Polyisobutene (PIB) (molecular weight 1000 g/mol) (10.0 g, 41 .6 parts per weight) was heated to 80°C.
  • Polymer P1 (4.25 g calculated as solid polymer, 17.3 parts per weight) and nonionic surfactant C10-Guerbetalcohol alkoxylate (HLB 12.5) (2.55 g, 10.4 parts per weight) were mixed and heated to 80°C as well.
  • the residual water originates from the water content of the raw materials.
  • the PIB was placed in a heated beaker and fitted with a high shear mixer (Polytron PT 10-35 GT) and the speed was set to 8000 to 10000 rpm. At 80 °C the mixture of polymer and non-ionic surfactant was added and treated at this shear rate for 120 sec without further heating. A homogeneous, highly concentrated emulsion that is stable against phase-separation for >2 week is formed.
  • Examples HC2 - HC12 are examples of the mixture of polymer and non-ionic surfactant
  • Example HC1 The following examples were prepared in a similar way as described in Example HC1 , taking the polymers and the respective amounts given in Table 3. All emulsions HC1 - HC12 can be diluted with water by simple low-shear stirring with a magnetic stirrer bar. Emulsion stability is assessed by visual inspection after 4h and 14 days. Emulsions are graded "homogeneous" (H in Table 3) when no visually observable
  • creaming/sedimentation and no coalescence and phase separation can be observed; they are graded "creaming” when creaming (CR) was observed but a homogeneous emulsion could be reformed by low-shear stirring.
  • Emulsions were graded "phase separation” (PS) when an oily phase was reformed and the emulsion could not easily be simple low-shear stirring.
  • Polyisobutene (PIB) (molecular weight 1000 g/mol) (17.5 parts per weight) and paraffin oil (17.5 parts per weight) were mixed and the mixture heated to 80 °C.
  • copolymer of DADMAC and acrylic acid CP1 (1.75 parts per weight, calculated as active content) and nonionic surfactant C10-Guerbetalcohol alkoxylate (HLB 12.5, 8.8 parts per weight) were mixed with de-ionized water (54.4 parts per weight) and heated to 80 °C as well.
  • Polyisobutene (PIB) (molecular weight 1000 g/mol) (17.5 parts per weight) and paraffin oil (17.5 parts per weight) were mixed and the mixture heated to 80 °C.
  • the PIB/paraffin mixture was placed in a heated beaker and fitted with the Ultraturrax equipped with shear-head T50 and the speed was set to 5000 to 6000 rpm.
  • the mixture of water, polymer and non-ionic surfactant was added and emulsified for 120 sec without further heating.
  • the resulting mixture showed creaming after approx. 4 hours and was separated into a clear water phase below and a white highly viscous phase on top. After stirring, creaming reappeared immediately.
  • Polyisobutene (PIB) (molecular weight 1000 g/mol) (17.5 parts per weight) and paraffin oil (17.5 parts per weight) were mixed and the mixture heated to 80 °C.
  • the DADMAC homopolymer CP3 (commercial Poly-DADMAC sample, (as supplied for example by Sigma-Aldrich under order numbers 522376 or 409014, CAS-# 26062-79- 3) (1 .75 parts per weight, calculated as active content) and nonionic surfactant C10- Guerbetalcohol alkoxylate (HLB 12.5, 8.8 parts per weight) were mixed with de-ionized water (54.4 parts per weight) and heated to 80 °C as well.
  • DADMAC homopolymer CP3 commercial Poly-DADMAC sample, (as supplied for example by Sigma-Aldrich under order numbers 522376 or 409014, CAS-# 26062-79- 3) (1 .75 parts per weight, calculated as active content) and nonionic surfactant C10- Guerbetalcohol alkoxylate (HLB 12.5, 8.8 parts per weight) were mixed with de-ionized water (54.4 parts per weight) and heated to 80 °C as well.
  • the PIB/paraffin mixture was placed in a heated beaker and fitted with the Ultraturrax equipped with shear-head T50 and the speed was set to 5000 to 6000 rpm.
  • the mixture of water, polymer and non-ionic surfactant was added and emulsified for 120 sec without further heating.
  • the resulting mixture showed creaming immediately after emulsification and was separated into a Clear water phase below and a white highly viscous phase on top. After stirring, creaming reappeared immediately.
  • Paraffin (35.0 parts per weight) was heated to 80 °C.
  • Polymer P1 (5 parts per weight, calculated as active content) and nonionic surfactant C10-Guerbetalcohol alkoxylate (HLB 12.5, 8.8 parts per weight) were mixed with de-ionized water (51.2 parts per weight) and heated to 80 °C as well.
  • Corn oil (35.0 parts per weight) was heated to 80 °C.
  • Polymer P1 (5 parts per weight, calculated as active content) and nonionic surfactant C10-Guerbetalcohol alkoxylate (HLB 12.5, 8.8 parts per weight) were mixed with de-ionized water (51.2 parts per weight) and heated to 80 °C as well.
  • the corn oil was placed in a heated beaker and fitted with the Ultraturrax equipped with shear-head T50 and the speed was set to 5000 to 6000 rpm. At 80 °C the mixture of water, polymer and non-ionic surfactant was added and emulsified for 120 sec without further heating. A homogeneous paraffin emulsion that is stable against phase- separation for >2 week is formed.
  • Soy bean oil (35.0 parts per weight) was heated to 80 °C.
  • Polymer P1 (5 parts per weight, calculated as active content) and nonionic surfactant C10-Guerbetalcohol alko- xylate (HLB 12.5, 8.8 parts per weight) were mixed with de-ionized water (51.2 parts per weight) and heated to 80 °C as well.
  • soy bean oil was placed in a heated beaker and fitted with the Ultraturrax equipped with shear-head T50 and the speed was set to 5000 to 6000 rpm.
  • the mixture of water, polymer and non-ionic surfactant was added and emulsified for 120 sec without further heating.
  • a homogeneous paraffin emulsion that is stable against phase- separation for >2 week is formed.
  • the following example formulations are made containing the emulsions of the present invention:
  • Liquid detergent fabric care compositions of Example A are made by mixing together the ingredients listed in the proportions shown;
  • Rinse-Added fabric care compositions are prepared by mixing together ingredients shown below:
  • Cationic polyacrylamide polymer such as a copolymer of acrylamide/[2-

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10808047B2 (en) 2015-08-21 2020-10-20 G&P Holding, Inc. Silver and copper itaconates and poly itaconates

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130118531A1 (en) * 2011-11-11 2013-05-16 The Procter & Gamble Company Emulsions containing polymeric cationic emulsifiers, substance and process
ES2910059T3 (es) * 2018-02-20 2022-05-11 Basf Se Método para producir tableros de fibra de madera
CN113121744B (zh) * 2021-04-02 2023-04-07 浙江凯色丽科技发展有限公司 快速交联固化的水性聚丙烯酸酯及其制备方法

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2923701A (en) 1955-05-02 1960-02-02 American Cyanamid Co Composition comprising a linear copolymer of a quaternary ammonium compound and an ethylenically unsaturated copolymerizable compound
US5486303A (en) 1993-08-27 1996-01-23 The Procter & Gamble Company Process for making high density detergent agglomerates using an anhydrous powder additive
US5489392A (en) 1994-09-20 1996-02-06 The Procter & Gamble Company Process for making a high density detergent composition in a single mixer/densifier with selected recycle streams for improved agglomerate properties
US5516448A (en) 1994-09-20 1996-05-14 The Procter & Gamble Company Process for making a high density detergent composition which includes selected recycle streams for improved agglomerate
DE19505100A1 (de) 1995-02-15 1996-08-22 Basf Ag Alk(en)yldicarbonsäurebisester, deren Verwendung sowie Verfahren zu deren Herstellung
US5565422A (en) 1995-06-23 1996-10-15 The Procter & Gamble Company Process for preparing a free-flowing particulate detergent composition having improved solubility
US5569645A (en) 1995-04-24 1996-10-29 The Procter & Gamble Company Low dosage detergent composition containing optimum proportions of agglomerates and spray dried granules for improved flow properties
US5574005A (en) 1995-03-07 1996-11-12 The Procter & Gamble Company Process for producing detergent agglomerates from high active surfactant pastes having non-linear viscoelastic properties
WO1996040808A1 (de) 1995-06-07 1996-12-19 Basf Aktiengesellschaft Verfahren zur herstellung von niedermolekularem, hochreaktivem polyisobuten
US5691297A (en) 1994-09-20 1997-11-25 The Procter & Gamble Company Process for making a high density detergent composition by controlling agglomeration within a dispersion index
US5879584A (en) 1994-09-10 1999-03-09 The Procter & Gamble Company Process for manufacturing aqueous compositions comprising peracids
EP0995791A1 (en) 1998-10-22 2000-04-26 Rohm And Haas Company Polymer compositions and a method of promoting soil release from fabrics using said polymer compositions
WO2002006359A1 (de) 2000-07-18 2002-01-24 Basf Aktiengesellschaft Verfahren zur herstellung von polyisobutenen
WO2007014915A1 (de) 2005-08-04 2007-02-08 Basf Se Wässrige dispersionen und ihre verwendung
WO2007042454A1 (de) 2005-10-12 2007-04-19 Basf Se Verfahren zur herstellung wässriger emulsionen und dispersionen

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5686024A (en) * 1995-12-18 1997-11-11 Rhone-Poulenc Surfactants & Specialties, L.P. Aqueous dispersion of a surface active polymer having enhanced performance properties
FR2833186B1 (fr) * 2001-12-12 2004-01-23 Rhodia Chimie Sa Utilisation de copolymeres cationiques a blocs comme aide au depot d'emulsions simples ou multiples
BR0316878B1 (pt) * 2002-12-23 2012-08-21 polìmeros hidrofobicamente modificados, produto de limpeza, formulação de processo têxtil, auxiliares de tingimento ou impressão e/ou agentes de acabamento, e método para processamento têxtil.
KR20070089138A (ko) * 2004-12-07 2007-08-30 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 소수성 변성된 양이온성 중합체 및 이들의 세정제로서 용도
CN101233187A (zh) * 2005-08-04 2008-07-30 巴斯福股份公司 水分散体及其用途
CN101365493A (zh) * 2005-11-24 2009-02-11 巴斯夫欧洲公司 结合角蛋白的效应分子以及产生其的方法
JP4944756B2 (ja) * 2006-12-28 2012-06-06 花王株式会社 繊維処理剤
MX340883B (es) * 2010-05-12 2016-07-29 Basf Se Emulsiones de poliisobutenos, sustancia y proceso.
US20130118531A1 (en) * 2011-11-11 2013-05-16 The Procter & Gamble Company Emulsions containing polymeric cationic emulsifiers, substance and process

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2923701A (en) 1955-05-02 1960-02-02 American Cyanamid Co Composition comprising a linear copolymer of a quaternary ammonium compound and an ethylenically unsaturated copolymerizable compound
US5486303A (en) 1993-08-27 1996-01-23 The Procter & Gamble Company Process for making high density detergent agglomerates using an anhydrous powder additive
US5879584A (en) 1994-09-10 1999-03-09 The Procter & Gamble Company Process for manufacturing aqueous compositions comprising peracids
US5691297A (en) 1994-09-20 1997-11-25 The Procter & Gamble Company Process for making a high density detergent composition by controlling agglomeration within a dispersion index
US5516448A (en) 1994-09-20 1996-05-14 The Procter & Gamble Company Process for making a high density detergent composition which includes selected recycle streams for improved agglomerate
US5489392A (en) 1994-09-20 1996-02-06 The Procter & Gamble Company Process for making a high density detergent composition in a single mixer/densifier with selected recycle streams for improved agglomerate properties
DE19505100A1 (de) 1995-02-15 1996-08-22 Basf Ag Alk(en)yldicarbonsäurebisester, deren Verwendung sowie Verfahren zu deren Herstellung
US5574005A (en) 1995-03-07 1996-11-12 The Procter & Gamble Company Process for producing detergent agglomerates from high active surfactant pastes having non-linear viscoelastic properties
US5569645A (en) 1995-04-24 1996-10-29 The Procter & Gamble Company Low dosage detergent composition containing optimum proportions of agglomerates and spray dried granules for improved flow properties
WO1996040808A1 (de) 1995-06-07 1996-12-19 Basf Aktiengesellschaft Verfahren zur herstellung von niedermolekularem, hochreaktivem polyisobuten
US5565422A (en) 1995-06-23 1996-10-15 The Procter & Gamble Company Process for preparing a free-flowing particulate detergent composition having improved solubility
EP0995791A1 (en) 1998-10-22 2000-04-26 Rohm And Haas Company Polymer compositions and a method of promoting soil release from fabrics using said polymer compositions
WO2002006359A1 (de) 2000-07-18 2002-01-24 Basf Aktiengesellschaft Verfahren zur herstellung von polyisobutenen
WO2007014915A1 (de) 2005-08-04 2007-02-08 Basf Se Wässrige dispersionen und ihre verwendung
WO2007042454A1 (de) 2005-10-12 2007-04-19 Basf Se Verfahren zur herstellung wässriger emulsionen und dispersionen

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
H. FIKENTSCHER, CELLULOSECHEMIE, vol. 13, 1932, pages 58 - 64,71-74
HEUSCH, R.: "Ullmann's Encyclopedia of Industrial Chemistry", 2000, WILEY-VCH, article "Emulsions", pages: 1 - 47
KOSTANSEK, E.: "Kirk-Othmer Encyclopedia of Chemical Technology", vol. 10, 2003, JOHN WILEY & SONS, article "Emulsions", pages: 113 - 133
ULLMANN'S: "Encyclopedia of Industrial Chemistry", 2005, WILEY-VCH VERLAG GMBH & CO. KGAA

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10808047B2 (en) 2015-08-21 2020-10-20 G&P Holding, Inc. Silver and copper itaconates and poly itaconates

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CN103930194B (zh) 2016-06-22
JP2015507520A (ja) 2015-03-12

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