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WO2013068272A1 - Compositions de polyoléfines auto-émulsifiables - Google Patents

Compositions de polyoléfines auto-émulsifiables Download PDF

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Publication number
WO2013068272A1
WO2013068272A1 PCT/EP2012/071441 EP2012071441W WO2013068272A1 WO 2013068272 A1 WO2013068272 A1 WO 2013068272A1 EP 2012071441 W EP2012071441 W EP 2012071441W WO 2013068272 A1 WO2013068272 A1 WO 2013068272A1
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weight
amount
composition
self
water
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Inventor
Rainer Dobrawa
Dieter Boeckh
Rajan K. Panandiker
Julie Menkhaus
Frank Huelskoetter
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BASF SE
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BASF SE
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • C09K23/003—Organic compounds containing only carbon and hydrogen
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3749—Polyolefins; Halogenated polyolefins; Natural or synthetic rubber; Polyarylolefins or halogenated polyarylolefins
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the present invention is directed to self-emulsifiable polyolefine compositions, in particular to self-emulsifiable polyisobutene compositions and the use of said emulsions.
  • Polyolefines and in particular polyisobutene(s) are useful ingredients in a lot of technical applications and contribute to improve the feel properties when applied on surfaces such as hair or textile.
  • the formulation of polyisobutene mostly consists in firstly emulsify the polyisobutene in an oil-in-water emulsion and then incorporate the emulsion in an aqueous formulation such as a hair care or laundry formulation, in order to obtain benefits such as emollience, hydrophobi- zation, lubrication or adhesion.
  • Polyisobutene emulsions are exemplified in
  • PCT/EP201 1/057586 which has not yet been published and which discloses an emulsion comprising (a) polyolefines such as polyisobutene, in an amount of from 2 to 75 weight%, (b) poly- mers Px which are copolymers of non ionic, anionic or pseudocationic monomers in an amount of from 0.05 to 40 weight % and (c) water in an amount of from 10 to 97.95 weight %.
  • 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 sub- stances 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, maleic anhydride and polyethyleneglycol. This dispersion is used for the treatment of leather or as additive in con- struction chemicals.
  • WO2004/154216 describes a copolymer containing polyisobutene, maleic anhydride and poly- alkylene glycols. These copolymers are used as emulsifiers for the preparation of oil-in-water emulsions and find applications e.g. in washing and cleaning formulations, in the cosmetics or pharmaceutical sector.
  • emulsions have to be prepared at high shear rate stirring, which is a complex process in the production scale and involve a high energy input.
  • emulsions are not thermodynamically stable, and can segregate by creaming / sedimentation, aggregation and coalescence (phase separation). Creaming is observed when emulsion droplets have a density lower than that of the continuous phase. Such droplets have the tendency to gather on top of the liquid level to form a layer enriched with emulsion droplets.
  • an emulsion which already contains a large amount of water
  • an aqueous formulation such as a hair care or laundry formulation reduces the flexibility of the formulator as to the choice of ingredients and the total concentration of the final formulation.
  • the problem to be solved is to identify a polyolefin composition that has a water content as low as possible or, even better, is completely free of water and that can be emulsified in aqueous formulations and/or water without the need for a high shear emulsification or any other standard emulsification process.
  • the composition should be able to self-emulsify only by stirring it into water or an aqueous formulation.
  • composition according to claims 1 to 12. The use of such a composition according to claim 13 forms an additional aspect of the present invention.
  • the prefix (meth) written before a compound means the respective unsubstituted compound and/or the compound substituted by the methyl group.
  • (meth)acrylic acid means acrylic acid and/or methacrylic acid
  • (meth)acrylate means acrylate and/or methacrylate
  • (meth)acrylamide means acrylamide and/or methacrylamide.
  • the present invention is directed to a self-emulsifiable composition containing
  • oil(s) Ox in an amount of from 0 to 40 weight %
  • water is not the continuous phase of the composition
  • weight ratio of polyolefine(s) to P x and S x is in the range of from 4:1 to 1 :3 and the weight ratio of Px to S x is higher than 1.25.
  • the self-emulsifiable composition can consist of components a) and b), in which case the amounts add up to 100 weight %, - such a composition forms a preferred embodiment of the present invention.
  • the composition can also contain components a) and b) as well as additional components.
  • the inventive composition may also contain other components.
  • the amounts, in which the respective compounds are present in the self- emulsifiable composition there exist preferred ranges.
  • a composition according to the invention wherein the components of the self-emulsifiable composition independently of each other are present in amounts of:
  • oil(s) Ox in an amount of from 0 to 40 weight %
  • additive(s) Ax in an amount of from 0 to 10 weight %
  • water is not the continuous phase of the composition
  • weight ratio of polyolefine(s) to P x and S x is in the range of from 4:1 to 1 :3 and the weight ratio of Px to S x is higher than 1.25.
  • composition wherein the components of the self-emulsifiable composition independently of each other are present in amounts of:
  • oil(s) Ox in an amount of from 0,1 to 30 weight %
  • water is not the continuous phase of the composition
  • weight ratio of polyolefine(s) to P x and S x is in the range from 4:1 to 1 :3 and the weight ratio of Px to S x is higher than 1.25.
  • a composition wherein the components of the self-emulsifiable composition independently of each other are present in amounts of:
  • water is not the continuous phase of the composition
  • weight ratio of polyolefine(s) to P x and S x is in the range from 4:1 to 1 :3 and the weight ratio of Px to S x is higher than 1.25.
  • further preferred emulsions are those, which comprise: a) polyolefine(s) in an amount of from 35 to 55 weight%,
  • water is not the continuous phase of the composition
  • weight ratio of polyolefine(s) to P x and S x is in the range from 4:1 to 1 :3 and the weight ratio of Px to S x is higher than 1 .25 a) polyolefine(s) in an amount of from 50 to 65 weight %,
  • water is not the continuous phase of the composition
  • weight ratio of polyolefine(s) to P x and S x is in the range from 4:1 to 1 :3 and the weight ratio of Px to S x is higher than 1 .25 a) polyolefine(s) in an amount of from 5 to 20 weight %,
  • water is not the continuous phase of the composition
  • weight ratio of polyolefine(s) to P x and S x is in the range from 4:1 to 1 :3 and the weight ratio of Px to S x is higher than 1 .25 or a) polyolefine(s) in an amount of from 40 to 60 weight %,
  • water is not the continuous phase of the composition, wherein the weight ratio of polyolefine(s) to P x and S x is in the range from 4:1 to 1 :3 and the weight ratio of Px to S x is higher than 1.25.
  • compositions In order to test whether or not water is the continuous phase of the composition a conductivity measurement is used showing that the compositions have a low conductivity in the range of the pure polyolefine(s), oil(s) or surfactant(s), and not a high conductivity as water.
  • composition according to the invention is self-emulsifiable, i.e. when mixed in an aqueous formulation, simple stirring is required for the composition to form an emulsion.
  • the self-emulsifiable composition is a water-free composition.
  • Water-free compositions are prepared without added water. Nevertheless, there might be minor amounts of residual water originating from the water content of the raw materials.
  • Self- emulsifiable water-free compositions contain less than 2 weight% of water, preferably less than 1 weight% of water, even more preferably, less than 0.5 weight% of water.
  • the self-emulsifiable composition is a water-reduced composition.
  • Water-reduced compositions are prepared by adding a reduced amount of water, in order to reduce the viscosity of the self-emulsifiable composition, so that the total amount of water in the composition lies in the range of from 2 to 8 weight%, preferably from 2 to 6 weight%, even more preferably from 2 to 5 weight%.
  • polyolefine(s) as used in the present invention is/are a chemical compound(s) 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. eth- ene/propene-copolymer or ethane/propene/hexane-terpolymer. It is particularly preferred, when the polyolefine(s) is/are substantially homopolymers, 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 polymer(s) is/are homopolymers, i.e. they consist of only one kind of monomer.
  • a composition, wherein the polyolefin(s) a) is/are selected from the group consisting of: polyethylene, polypropylene, polybutylene and polyisobutylene is preferred.
  • the composition can comprise one or more polyolefine.
  • An emulsion, which only comprises one polyolefine a) is preferred.
  • a composition, which only comprises polyisobutylene as polyolefine a) is particularly preferred.
  • the polyolefines a) can be prepared by the usual procedures (Ullmann's Encyclope- dia of Industrial Chemistry, Polyolefins, Whiteley, Heggs, Koch, Mawer, Immel, Wiley-VCH Ver- lag GmbH & Co. KGaA, Weinheim 2005).
  • the production of polyisobutylene is described e.g. in WO 02/06359 and WO 96/40808 in even more detail.
  • the polyolefine(s) a) 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 polyolefin(s) a) 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 a) is from 550 to 2000 g/mol.
  • composition according to the invention comprises polymeric emulsifi- er(s) Px, wherein ⁇ is/are selected from the group consisting of
  • Pi polyisobutene derivatives, wherein Pi is polyisobutenamine, polyisobutene succinic anhydride, a copolymer of polyisobuten succinic anhydride with polyalkylene glycol, a copolymer of polyisobuten succinic anhydride with an oligoamine or with an oligoamine alkoxylate.
  • Polyisobutylene succinic acid is prepared by en-reaction of succinic anhydride and polyisobutylene, as described in DE-A 19519042, DE-A 4319671 , DE-A 4319672 or H. Mach and P. Rath in "Lubrication Science II (1999), S. 175-185.
  • the preparation of polyisobutene and polyisobutene amine is described in EP244616 and references cited therein.
  • Copolymers of polyisobutene succinic anhydride with polyalkylene glycol are described in WO2007/014915.
  • Copolymers of succinic anhydride with oligoamine or with an oligoamine alkoxylate are described in
  • the polyisobutylene part has a molar mass (M n ) of at least 250 g/mol, preferably at least 350 g/mol and more preferred at least 500 g/mol, and a maximum molar mass M n of 10.000 g/mol, preferably 5000 g/mol and more preferred of 2500 g/mol.
  • M n molar mass of the polyisobutylene part
  • the most preferred range of the molar mass M n of the polyisobutylene part is from 550 to 2000 g/mol.
  • Polymer P1 is preferably selected from the group consisting of polyisobutene derivatives, wherein Pi is polyisobutenamine, polyisobutene succinic anhydride, a copolymer of polyisobuten succinic anhydride and polyethylene glycol.
  • Monomer A2 is a cationic monoethylenically unsaturated monomer which is at least partially soluble in water of the reaction solvent, or in the other monomers if no water or solvent is used.
  • Suitable examples of monomer A are (3-acrylamidopropyl)-trimethylammonium chloride (AP- TAC), (3-methacrylamidopropyl)-trimethylammonium chloride (MAPTAC), dimethylaminopropy- lacrylat methochlorid, dimethylaminopropylmethacrylat methochlorid, diallyl dimethyl ammonium chloride (DADMAC).
  • Monomer A is preferably DADMAC.
  • Monomer B2 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 acry- late.
  • Monomer B is preferably lauryl acrylate (LA).
  • Monomer C2 is a C3-C8 monoethylenically unsaturated carboxylic acid. Suitable examples of monomer C include acrylic acid, methacrylic acid, crotonic acid, maleic acid, maleic anyhydride, fumaric acid, itaconic acid and alkyli and metal salts thereof. Monomer C is preferably acrylic acid (AA).
  • the polymer P x is preferably the product of the polymerization of
  • Another preferred embodiment is a polymer P2 which is the product of the polymerization of: A2) from 70 to 90 weight % of monomer A2,
  • polymer P2 is a polymeric cationic emulsifier, wherein P2 is the result of the polymerization of
  • R * H, CH 3 ,
  • R H, methyl
  • R' H, methyl
  • n 1 to 200
  • polyalkylene(s) of formula 3 is preferrably composed of:
  • n 1 to 200
  • n 1 to 200
  • the composition can comprise one or more polymers of one or more of the groups Pi), P2) and P3). If two or more polymers of one group and/or of different groups are present, they can be present in equal amounts or in different amounts.
  • esters of C10- to C26-carboxylic acid with C& - C24-alcohols and
  • Preferred oil(s) O x are mineral oils available under the names mineral oil light, mineral oil heavy, paraffin liquid or Nujol, that are liquid at room temperature.
  • mineral oil available from Sigma-Aldrich Chemie GmbH, Kunststoff, under the order number 69808.
  • Particularly preferred oils are silicone oils. Preferred silicone contents are less that 5 weight %, preferably less than 3 weight%, even more preferably less than 1 weight%.
  • Suitable silicone oils are, for example, linear polydimethylsiloxanes,
  • CTFA dimethicone copolyols
  • the number-average molecular weight of the polylsiloxanes is preferably in a range from about 1000 to 150 000 g/mol.
  • a self-emulsifiable composition wherein the surfactant(s) S x is/are selected from the group consisting of:
  • anionic surfactants d2) anionic surfactants and d3) cationic surfactants is preferred.
  • 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.
  • ethylene oxide EO
  • propylene oxide PO
  • butyl- ene oxide BO
  • sulfate sulfonate
  • carbonic acids ammonium und ammonium oxide
  • anionic surfactants are: carboxylates, sulfonates, sulfo fatty acid methylesters, sulfates, phosphates.
  • cationic surfactants are: quartery ammonium compounds.
  • betaine-surfactants are: alkyl betaines.
  • non-ionic compounds are: al- cohol alkoxylates.
  • a Treatcarboxylate is a compound, which comprises at least one carboxylate-group in the molecule.
  • Examples of 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,
  • alkyl sulfonates e.g. Alscoap OS-14P, BIO-TERGE® AS-40, BIO-TERGE® AS-40 CG, BIO-TERGE® AS-90 Beads, Calimulse® AOS-20, Calimulse® AOS-40, Calsoft® AOS-40, Colonial® AOS-40, Elfan® OS 46, Ifrapon® AOS 38, Ifrapon® AOS 38 P, Jeenate® AOS-40, Nikkol® OS-14, Norfox® ALPHA XL, POLYSTEP® A-18, Rhodacal®
  • aromatic sulfonates e.g. Nekal® BX, Dowfax® 2A1.
  • a ..sulfo fatty acid methylester is a compound, having the following general formula (I):
  • R 13 has 10 to 20 C-atoms; preferably 12 to 18 and particularly preferred 14 to 16 C- atoms.
  • a ..sulfate is a compound, which comprises at least one SCvgroup in the molecule.
  • SCvgroup in the molecule.
  • fatty acid alcohol sulfates such as coco fatty alcohol sulfate (CAS 97375-27-4)— e.g.
  • coco fatty alcohol ethersulfates e.g. Emal® 20C, Latemul® E150, Sulfochem® ES-7 i Texapon® ASV-70 Spec, Agnique SLES-229-F, Octosol 828, POLYSTEP® B-23, Uni- pol® 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 PC group.
  • examples of phosphates, which can be used according to the present invention, are
  • alkyl ether phosphates e.g. Maphos® 37P, Maphos® 54P, Maphos® 37T, Maphos® 210T and Maphos® 21 OP,
  • 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- and tri(hydroxyethyl)ammonium salts.
  • One group of the cationic surfactants are the quarternary ammonium compounds.
  • a ..quarternary ammonium compound is a compound, which comprises at least one R 4 N + -group per molecule.
  • Examples of counter ions, which are useful in the quarternary ammonium compounds, are
  • Particularly suitable cationic surfactants are:
  • imidazolinquats especially 1 -alkylimidazoliniumsalts of formula II or III
  • R 9 Ci-C 25 -alkyl or C 2 -C 2 5-alkenyl
  • R 10 Ci-C 4 -alkyl or hydroxy-Ci-C 4 -alkyl
  • R 11 Ci-C 4 -alkyl, hydroxy-Ci-C 4 -alkyl or a rest R 1 -(CO)-X-(CH 2 ) m - (X:-0- or -NH-; m: 2 or
  • 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
  • Non-ionic surfactants are interfacially active substances having a head group, which is an uncharged, polar, hydrophilic group, not carrying an 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, (polyethyleneglycol-groups), including fatty alcohol polyglycol ether (fatty alcohol alkoxylates), alkylphenol polyglycolether and fatty acid ethoxylates, alkox- ylated triglycerides and mixed ethers (polyethylene glycolether alkoxylated on both sides); and carbohydrate-groups, including e.g. alkyl polyglucosides and fatty acid-A/-methylglucamides.
  • fatty alcohol polyglycol ether fatty alcohol alkoxylates
  • alkylphenol polyglycolether alkylphenol polyglycolether
  • mixed ethers polyethylene glycolether alkoxylated on both sides
  • carbohydrate-groups including e.g. alkyl polyglucosides and fatty acid-A/-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.
  • EO ethylene oxide
  • PO propylene oxide
  • BuO butylene oxide
  • 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 12 comprises 1 1 to 17 C-atoms and 1 ⁇ m + n ⁇ 5.
  • Alkylpolyglycosides are mixtures of alkylmonoglucosides (alkyl- a-D- and - ⁇ -D-glucopyranoside 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)
  • Lutensol ® GD70 One example is Lutensol ® GD70.
  • R 6 is a n-Ci2-alkyl-moiety
  • R 7 an alkyl-moiety having 1 to 8 C-atoms.
  • R 7 preferably is methyl.
  • a self-emulsifiable composition wherein the additive(s) A x is/are selected from the group sisting of: disinfectant, dye, acid, base, complexing agent, biocide, hydrotope, thickener, builder, cobuild- er, 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 en- hancer, perfume, gel formers, dyes, pigments, photoprotective agents, consistency regulators, antioxidants, bleaches, care agents, tints, tanning agents, humectants, refatting agents, collagen, protein hydrolysates, lipids, emollients, softeners, antifoams, antistats, resins, solvents, solubility promoters, neutralizing agents, stabilizers, sterilizing agents, propellants, drying agents, o
  • Disinfectants can be: oxidation agents, halogens such as chlorine and iodine and substances, which release the same, alcohols such as ethanol, 1 -propanol and 2-propanol, aldehydes, phe- noles, ethylene oxide, chlorohexidine and mecetroniummetilsulfate.
  • oxidation agents such as chlorine and iodine and substances, which release the same
  • alcohols such as ethanol, 1 -propanol and 2-propanol
  • aldehydes such as ethanol, 1 -propanol and 2-propanol
  • aldehydes such as ethanol, 1 -propanol and 2-propanol
  • aldehydes such as ethanol, 1 -propanol and 2-propanol
  • aldehydes such as ethanol, 1 -propanol and 2-propanol
  • aldehydes such as ethanol, 1 -propanol and 2-propan
  • 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 acid, sulfuric acid and sulfonic acid.
  • Bases are compounds, which are useful for adjusting a preferable pH-range for complexing agents. Examples of bases, which can be used according to the present invention, are: NaOH, KOH and amine ethanol.
  • zeolites different types 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 layer-silicates, e.g. ⁇ - and p-Na2Si20s.
  • 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-d-Cs-alkylether, vinylacetate, vinylpropi- onate, (meth)acryl acid ester of d-Cs-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, oxodisuccinic acid and bu- tanetetracarbonic 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 at inorganic salts, such as sodium perborate-monohydrate, sodium perborate-tetrahydrate and sodium carbonate-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.
  • 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-vinyl pyridin, 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.
  • a self-emulsifiable composition which has a content of organic solvent below 50 mg/kg of emulsion is particularly preferred.
  • a self-emulsifiable composition that forms a transparent, homogeneous oil-phase forms one preferred embodiment of the present invention.
  • the self-emulsifiable compositions can be prepared by simply mixing and stirring the compounds a) to e) with each other until a homogeneous composition is obtained.
  • the step of combining the components can vary: in one preferred embodiment, polymer(s) P x is dissolved in polyisobutene, optionally comprising oil(s) and/or additional components, and then optionally combined with surfactants and additional components.
  • polymer(s) P x is optionally mixed with surfactants and/or addi- tional components, and then combined with polyisobutene phase, comprising polyisobutene and optionally oil(s) and/or additional components.
  • the premixes or formulations are assessed “clear”, when the transmittance of the formulation, measured with a CADAS 200 spectrophotometer (Dr. Lange Company) at 650 nm in a 1 cm cuvette is higher than 90%.
  • the premix or formulations are assessed “homogeneous”, when upon visual inspection no creaming / sedimentation or phase separation can be observed after one day.
  • the premixes or formulations are assessed "phase separated” when the mixture separated into clearly recognizable organic and aqueous phases, or if droplets of organic phase could be observed on top of the aqueous phase.
  • Polyisobutene (6.0 g, 60 parts per weight, molecular weight 1000 g/mol) and polyisobutene succinic anhydride (3.0 g, 30 parts per weight) were mixed in a 25ml glass vial and stirred at low shear with a magnetic stirrer bar. The mixture was heated to 80°C to reduce viscosity and thus simplify mixing.
  • Nonionic surfactant C10-Guerbetalcohol alkoxylate (HLB 12.5) (1 .0 g, 10 parts per weight) was added and the resulting mixture was stirred for 5 min, yielding an emulsifiable polyisobutene composition PM1 in the form of a homogeneous, clear and stable solution.
  • Example PM1 The mixture is prepared in the same way as Example PM1 , applying the ratios given in the table below. All examples formed homogeneous, clear and stable solutions.
  • Polyisobutene (6.0 g, 60 parts per weight, molecular weight 1000 g/mol) and polyisobutene succinic anhydride (3.0 g, 30 parts per weight) were mixed in a 25ml glass vial and stirred at low shear with a magnetic stirrer bar. The mixture was heated to 80°C to reduce viscosity and thus simplify mixing.
  • Polyisobutene (5.0 g, 50 parts per weight, molecular weight 1000 g/mol) , polyisobuteneamine (3.25 g, 32.5 parts per weight) and n-paraffin C5-C20 (1 .75 g, 17.5 parts per weight) were mixed in a 25ml glass vial and stirred at low shear with a magnetic stirrer bar.
  • the composition is a homogeneous, clear and stable solution.
  • Polyisobutene (4.0 g, 40 parts per weight, molecular weight 1000 g/mol) , polyisobuteneamine (3.9 g, 39.0 parts per weight) and n-paraffin C5-C20 (2.1 g, 21.0 parts per weight) were mixed in a 25ml glass vial and stirred at low shear with a magnetic stirrer bar.
  • the composition is a homogeneous, clear and stable solution.
  • Polyisobutene (1 .0 g, 10 parts per weight, molecular weight 1000 g/mol) , polyisobuteneamine (5.85 g, 58.5 parts per weight) and n-paraffin C5-C20 (3.15 g, 31.5 parts per weight) were mixed in a 25ml glass vial and stirred at low shear with a magnetic stirrer bar.
  • the composition is a homogeneous, clear and stable solution.
  • Polyisobutene (24.0 g, molecular weight 1000 g/mol) and polyisobutene succinic anhydride ( 12.0 g) were mixed in a 25ml glass vial and stirred at low shear with a magnetic stirrer bar. The mixture is heated to 80°C to reduce viscosity and thus simplify mixing.
  • a mixture of nonionic surfactant C10-Guerbetalcohol alkoxylate (HLB 12.5) (4.0 g) and water (2.0 g) is added and the mixture is stirred for 30 min, yielding an emulsifiable polyisobutene composition in the form of a homogeneous clear stable solution.
  • Polyisobutene (24.0 g, molecular weight 1000 g/mol) and polyisobutene succinic anhydride (12.0 g) were mixed in a 25ml glass vial and stirred at low shear with a magnetic stirrer bar. The mixture is heated to 80°C to reduce viscosity and thus simplify mixing.
  • Nonionic surfactant C10- Guerbetalcohol alkoxylate (HLB 12.5) (4.0 g) is added and the mixture is stirred for 5min. Sub- sequently, water (2 g) is added and the mixture is stirred for another 5 min, yielding an emulsifi- yable polyisobutene composition in the form of a homogeneous clear stable solution.
  • Formulations (F) of Polyisobutylene Premixes in Liquid Detergents 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. 5,574,005; U.S. 5,569,645; U.S. 5,565,422; U.S. 5,516,448; U.S. 5,489,392; U.S. 5,486,303 all of which are incorporated herein by reference.
  • Liquid detergent fabric care compositions of Example A were made by mixing together the ingredients listed in the proportions shown;
  • Liquid detergent formulation A (97.80 g) was placed in a 150 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • Polyisobutene Premix PM1 (2.20 g) was slowly added to the detergent formulation upon stirring.
  • the resulting turbid polyisobutene containing formulation was stirred for another 30 min to form a homogeneous, clear and stable formulation.
  • Liquid detergent formulation A (98.0 g) was placed in a 150 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • the resulting turbid polyisobutene containing formulation was stirred for another 30 min to form a phase-separated turbid mixture with a ring of polyisobutene on top of the liquid level.
  • Cationic polyacrylamide polymer such as a copolymer of acrylamide/[2- (acryloylamino)ethyl]tri-methylammonium chloride (quaternized dimethyl aminoethyl acry- late) available from BASF, AG, Ludwigshafen under the trade name Sedipur ® 544.
  • Fabric softener formulation B (98.0 g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • Polyisobutene premix PM1 1 (2.0 g) was slowly added to the fabric softener formulation upon stirring.
  • the resulting polyisobutene containing fabric softener formulation was stirred for another 30 min to form a homogeneous stable formulation that did not show any signs of phase separation.
  • Example F16
  • Example F17 The example is prepared analogous to Example F15, with the difference that the Polyisobutene premix PM1 1 is colored with a red, oil-soluble and water-insoluble dye (Sudan Red 7B, Sigma- Aldrich, 20 ppm) and the liquid fabric enhancer is colored with a blue, water-soluble and oil- insoluble dye (Liquitint Blue, Milliken, 20 ppm).
  • the resulting polyisobutene containing formula- tion exhibited a homogeneous, violet color as a result of the perfect emulsification of the water phase and the oil phase, showing not sign of creaming / sedimentation (i.e. no clear blue aqueous phase on top or bottom), as well as not sign of phase separation (i.e. no red oil phase or red oil droplets observable).
  • Example F17 Example F17:
  • Fabric softener formulation B (98.0 g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm. Polyisobutene premix PM13 (2.0 g) was slowly added upon stirring. The resulting polyisobutene containing fabric softener formulation was stirred for another 30 min to form a homogeneous stable formulation that did not show any signs of phase separation.
  • Example 7B The example was prepared analogous to Example F17, with the difference that the Polyisobu- tene premix PM5 is colored with a red, oil-soluble and water-insoluble dye (Sudan Red 7B,
  • the liquid fabric enhancer is colored with a blue, water-soluble and oil-insoluble dye (Liquitint Blue, Milliken, 20 ppm).
  • a blue, water-soluble and oil-insoluble dye Liquitint Blue, Milliken, 20 ppm.
  • the resulting polyisobutene containing formulation exhibited a homogeneous, violet color as a result of the perfect emulsification of the water phase and the oil phase, showing not sign of creaming / sedimentation (i.e. no clear blue aque- ous phase on top or bottom), as well as not sign of phase separation (i.e. no red oil phase or red oil droplets observable).
  • Fabric softener formulation B (98.0 g) that is colored with a blue, water-soluble and oil-insoluble dye (Liquitint Blue, Milliken, 20 ppm) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm. Polyisobutene (2.0 g, 1000 g/mol), colored with a red, oil-soluble and water-insoluble dye (Sudan Red 7B, Sigma-Aldrich, 20 ppm) was slowly added to the fabric softener formulation upon stirring.
  • a blue, water-soluble and oil-insoluble dye Liquitint Blue, Milliken, 20 ppm
  • the resulting polyisobutene containing formulation was stirred for another 30 min to form a clearly phase-separated product consisting of a polyisobutene phase forming a red-colored ring at the top of the liquid level and a liquid fabric enhancer phase forming a blue aqueous phase.
  • Liquid Hand Dish Wash formulation compositions prepared by mixing together ingredients shown below.
  • TMBA trimethoxy benzoic acid
  • HEDP is 1 -hydroxyethylidene 1 ,1 -diphosphonic acid
  • the hand dishwash formulation (50 g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • Polyisobutene premix PM2 (1 .1 g) was slowly added upon stirring.
  • the resulting polyisobutene containing formulation was stirred for another 30 min to form a turbid, homogeneous liquid.
  • the hand dishwash formulation (50g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • Polyisobutene premix PM13 (1.54 g) was slowly added upon stirring.
  • the resulting polyisobutene containing formulation was stirred for another 30 min to form a clear homogeneous liquid.
  • the hand dishwash formulation (50g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm. Polyisobutene (molecular weight 1000 g/mol, 1.0 g) was slowly added upon stirring. The resulting polyisobutene containing formulation was stirred for another 30 min to form a turbid liquid with clearly phase separated droplets of polyisobutene on top of the liquid.
  • Cocoamidopropylbetaine (12.5 g, 29.5 % active in water) and sodium laureth sulfate (35.7 g, 29 % active) were mixed with demineralized water (51 .8 g) to form a standard shampoo or body- wash formulation.
  • the product can be thickened with 1.0 g of sodium chloride.
  • the standard shampoo and bodywash formulation (50 g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm. Polyisobutene premix PM1 (1 .1 g) was slowly added upon stirring. The resulting polyisobutene containing formulation was stirred for another 30 min to form a turbid, homogeneous liquid.
  • the standard shampoo and bodywash formulation (50 g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • Polyisobutene premix PM13 (1.54 g) was slowly added upon stirring.
  • the resulting polyisobutene containing formulation was stirred for another 30 min to form a slightly turbid liquid that shows slight creaming upon storage.
  • Dodecylbenzenesulfonate amine salt (20 g, 55% active in water), C10-Guerbetalcohol+7EO (HLB 12.5) (2 g, 100% active) and alkylpolyglucoside (2 g, 70% active) were mixed with water (76 g) to form a standard car shampoo formulation for home users.
  • the standard car wash formulation (50 g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • Polyisobutene premix PM1 (1 .1 g) was slowly added upon stirring.
  • the resulting polyisobutene containing formulation was stirred for another 30 min to form a slightly turbid, homogeneous liquid.
  • the standard car wash formulation (50 g) was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • Polyisobutene premix PM13 (1 .54 g) was slowly added upon stirring.
  • the resulting polyisobutene containing formulation was stirred for another 30 min to form an opaque homogenous liquid.
  • the standard car wash formulation 50 g was placed in a 100 ml glass beaker and stirred with a mechanical cross-bar stirrer at 325 rpm.
  • Polyisobutene (molecular weight 1000 g/mol, 1 .54 g) was slowly added upon stirring.
  • the resulting polyisobutene containing formulation was stirred for another 30 min to form an inhomogenous, turbid liquid that instantaneously showed creaming and phase separation.
  • PIBSA Polyisobutene Succinic Anhydride
  • all premixes display the same conductivity as the hydrophobic components such as PIB or PIBA, showing that water is not the continuous phase in these premixes.

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Abstract

La présente invention concerne des compositions auto-émulsifiables comprenant des polyoléfines, notamment du polyisobutène, le procédé d'obtention desdites émulsions et l'utilisation desdites émulsions.
PCT/EP2012/071441 2011-11-11 2012-10-30 Compositions de polyoléfines auto-émulsifiables Ceased WO2013068272A1 (fr)

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Cited By (1)

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

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