EP1354001A2 - Compositions renfermant des copolymeres a base d'acide acryloyldimethyl-amino-ethylsulfonique et des additifs synergiques - Google Patents

Compositions renfermant des copolymeres a base d'acide acryloyldimethyl-amino-ethylsulfonique et des additifs synergiques

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Publication number
EP1354001A2
EP1354001A2 EP01998569A EP01998569A EP1354001A2 EP 1354001 A2 EP1354001 A2 EP 1354001A2 EP 01998569 A EP01998569 A EP 01998569A EP 01998569 A EP01998569 A EP 01998569A EP 1354001 A2 EP1354001 A2 EP 1354001A2
Authority
EP
European Patent Office
Prior art keywords
acid
compositions according
vinyl
optionally
copolymers
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01998569A
Other languages
German (de)
English (en)
Inventor
Roman MORSCHHÄUSER
Christoph Kayser
Matthias LÖFFLER
Karl Heinz Heier
Aranka Tardi
Manfred Schade
Gernold Botthof
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE10059821A external-priority patent/DE10059821A1/de
Priority claimed from DE10059818A external-priority patent/DE10059818A1/de
Priority claimed from DE10059829A external-priority patent/DE10059829A1/de
Priority claimed from DE10059823A external-priority patent/DE10059823A1/de
Priority claimed from DE10059825A external-priority patent/DE10059825A1/de
Priority claimed from DE10059822A external-priority patent/DE10059822A1/de
Priority claimed from DE10059833A external-priority patent/DE10059833A1/de
Priority claimed from DE10059824A external-priority patent/DE10059824A1/de
Priority claimed from DE10059827A external-priority patent/DE10059827A1/de
Priority claimed from DE10059828A external-priority patent/DE10059828A1/de
Priority claimed from DE10059826A external-priority patent/DE10059826A1/de
Priority claimed from DE10059819A external-priority patent/DE10059819A1/de
Priority claimed from DE10059832A external-priority patent/DE10059832A1/de
Priority claimed from DE10059830A external-priority patent/DE10059830A1/de
Priority claimed from DE10059831A external-priority patent/DE10059831A1/de
Priority claimed from DE2001127876 external-priority patent/DE10127876A1/de
Application filed by Clariant GmbH filed Critical Clariant GmbH
Publication of EP1354001A2 publication Critical patent/EP1354001A2/fr
Withdrawn legal-status Critical Current

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    • 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
    • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. 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
    • A61K8/86—Polyethers
    • 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
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • 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
    • A61K8/91—Graft copolymers
    • 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
    • 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
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
    • C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of amides or imides
    • 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
    • C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
    • C08F271/02—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00 on to polymers of monomers containing heterocyclic nitrogen
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • 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
    • A61K2800/54—Polymers characterized by specific structures/properties
    • 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
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate

Definitions

  • compositions containing copolymers based on acryloyldimethyltauric acid and synergistic additives are included in compositions containing copolymers based on acryloyldimethyltauric acid and synergistic additives.
  • the invention relates to compositions containing copolymers based on acryloyldimethyltauric acid and synergistic additives selected from anionic, cationic, nonionic and betaine surfactants.
  • the compositions show a pronounced thermoassociative behavior and are outstandingly suitable as thickeners.
  • Such thickeners especially the "superabsorbers” based on polyacrylic acid, have been an integral part of the hygiene sector since their development in the 1970s.
  • partially or fully neutralized polyacrylic acids and their water-soluble copolymers are used as consistency agents in many cosmetic formulations.
  • the variety of possible structures and the associated diverse application possibilities are not least expressed in a large number of patents that have been registered worldwide since the mid-1970s.
  • novel thickeners based on 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) or their salts were introduced onto the market (EP 816 403 and WO 98/00094).
  • AMPS 2-acrylamido-2-methyl-1-propanesulfonic acid
  • thickeners are superior to the corresponding polycarboxylates (carbopoles) in many respects.
  • thickener systems based on AMPS show excellent properties in pH ranges below pH 6, i.e. in a pH range in which it is no longer possible to work with conventional polycarboxylate thickeners.
  • microgel structure inherent in the acryloyldimethyltauric acid thickeners leads to a particularly pleasant feeling on the skin. The easy processability and the favorable toxicological profile of the main monomer give these thickeners a high application potential.
  • synergistic additives selected from anionic, cationic, betaine and nonionic surfactants
  • thermoviscosification can also be implemented in formulations which contain a lot of electrolytes.
  • the invention relates to compositions containing
  • thermosensitive, macromonomers with a number average molecular weight greater than or equal to 200 g / mol
  • Component selected from groups B) to G) is copolymerized, at least one of the structural elements selected from groups B) to G) having thermosensitive properties;
  • At least one synergistic additive selected from anionic, cationic, nonionic and betaine surfactants.
  • the copolymers preferably have a molecular weight of 10 3 g / mol to 10 9 g / mol, particularly preferably 10 4 to 10 7 g / mol, particularly preferably 5 * 10 4 to 5 * 10 6 g / mol.
  • the Acryloyldimethyltauraten can be the inorganic or organic salts of Acryloyldimethyltaurinklare.
  • the Li + , Na + , K + , Mg + ⁇ Ca ++ , Al +++ and / or NH 4 + salts are preferred.
  • the monoalkylammonium, dialkylammonium, trialkylammonium and / or tetraalkylammonium salts where the alkyl substituents of the amines independently of one another can be (C 1 -C 22 ) -A! Alkyl radicals, which may optionally contain up to 3 (C 2 -C ⁇ o) -Hydroxyalkyl phenomenon can be occupied. Furthermore, one to three times ethoxylated ammonium compounds with different degrees of ethoxylation are preferred. It should be noted that mixtures of two or more of the abovementioned representatives or the free acryloyldimethyltauric acid are also within the meaning of the invention.
  • the degree of neutralization of acryloyldimethyltauric acid in the copolymers can be between 0 and 100%, a degree of neutralization of above 80% is particularly preferred.
  • the content of acryloyldimethyltauric acid or acryloyldimethyltaurates can be 0.1 to 99.9% by weight, preferably 20 to 99.5% by weight, particularly preferably 50 to 98% by weight.
  • comonomers B All olefinically unsaturated, non-cationic monomers whose reaction parameters permit copolymerization with acryloyldimethyltauric acid and / or acryloyldimethyltaurates in the respective reaction media can be used as comonomers B).
  • Preferred comonomers B) are unsaturated carboxylic acids and their anhydrides and salts, and also their esters with aliphatic, olefinic, cycloaliphatic, arylaliphatic or aromatic alcohols with a carbon number of 1 to 22.
  • Acrylic acid, methacrylic acid, styrenesulfonic acid, maleic acid are particularly preferred. Fumaric acid, crotonic acid, itaconic acid and senecioic acid.
  • Preferred counterions are Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NH 4 + , monoalkylammonium, dialkylammonium, trialkylammonium and / or tetraalkyl- ammonium radicals, it being possible for the alkyl substituents of the amines to be (C 1 -C 22 ) -alkyl radicals independently of one another, which can optionally be occupied by up to 3 (C 2 -C- 0 ) -hydroxyalkyl groups. In addition, one to three times ethoxylated ammonium compounds with different degrees of ethoxylation can also be used. The degree of neutralization of the carboxylic acids can be between 0 and 100%.
  • comonomers B) are open-chain N-vinylamides, preferably N-vinylformamide (VIFA), N-vinylmethylformamide, N-vinylmethylacetamide (VIMA) and N-vinylacetamide; cyclic N-vinylamides (N-vinyllactams) with a ring size of 3 to 9, preferably N-vinylpyrrolidone (NVP) and N-vinylcaprolactam; Amides of acrylic and methacrylic acid, preferably acrylamide, methacrylamide, N, N-dimethylacrylamide, N, N-diethylacrylamide and N, N-diisopropylacrylamide; alkoxylated acrylic and methacrylamides, preferably hydroxyethyl methacrylate, hydroxymethyl methacrylamide, hydroxyethyl methacrylamide, hydroxypropyl methacrylamide and succinic acid mono- [2- (methacryloyloxy) eth
  • thermosensitive properties in the polymer so that the corresponding polymers have LCST and / or UCST properties.
  • the following non-limiting list represents the best-known monomers which copolymers with thermosensitive properties can produce: N, N-diisopropylacrylamide, N-vinylpyrrolidone (NVP), methacrylic acid and vinyl acetate or vinyl alcohol units in the polymer.
  • the copolymers are crosslinked, ie they contain comonomers B) with at least two polymerizable vinyl groups.
  • Preferred crosslinkers are methylene bisacrylamide; methylenebismethacrylamide; Esters of unsaturated mono- and polycarboxylic acids with polyols, preferably diacrylates and triacrylates or methacrylates, particularly preferably butanediol and ethylene glycol diacrylate or methacrylate, trimethylolpropane triacrylate (TMPTA) and trimethylolpropane trimethacrylate (TMPTMA); Allyl compounds, preferably allyl (meth) acrylate, triallyl cyanurate, maleic acid diallyl ester, polyallyl ester, tetraallyloxyethane, triallylamine, tetraallylethylene diamine; Allyl esters of phosphoric acid; and / or vinylphosphonic acid derivatives.
  • TMPTA Trimethylolpropane triacrylate
  • the proportion by weight of comonomers B), based on the total mass of the copolymers, can be 0 to 99.9% by weight and is preferably 0.05 to 80% by weight, particularly preferably 0.05 to 70% by weight.
  • Suitable comonomers C) are all olefinically unsaturated monomers with a cationic charge which are capable of forming copolymers in the selected reaction media with acryloyldimethyltauric acid or its salts.
  • the resulting distribution of the cationic charges over the chains can be statistical, alternating, block-like or gradient-like.
  • the cationic comonomers C) are also to be understood as meaning those which carry the cationic charge in the form of a betaine structure.
  • Comonomers C) in the sense of the invention are also amino-functionalized precursors which can be converted into their corresponding quaternary derivatives by polymer-analogous reactions (e.g. reaction with DMS).
  • comonomers C are diallyldimethylammonium chloride (DADMAC), [2- (methacryloyloxy) ethyl] trimethylammonium chloride (MAPTAC), [2- (acryloyloxy) ethyl] trimethylammonium chloride, [2-methacrylamidoethyl] trimethylammonium chloride, [2- (acrylamido) ethyl] trimethylammonium chloride, N-methyl-2-vinylpyridinium chloride and / or N-methyl-4-vinylpyridinium chloride.
  • the proportion by weight of the comonomers C), based on the total mass of the copolymers, is preferably 0.1 to 99.8% by weight, particularly preferably 0.5 to 30% by weight and particularly preferably 1 to 20% by weight.
  • Suitable polymerizable, silicon-containing components D) are all at least mono-olefinically unsaturated compounds which are capable of radical copolymerization under the reaction conditions chosen in each case.
  • the distribution of the individual silicone-containing monomers across the resulting polymer chains does not necessarily have to be statistical.
  • the formation of, for example, block (also multiblock) or gradient-like structures is also within the meaning of the invention. Combinations of two or more different silicone-containing representatives are also possible.
  • the use of silicone-containing components with two or more polymerization-active groups leads to the formation of branched or cross-linked structures.
  • Preferred silicon-containing components D) are those of the formula (I).
  • R 1 represents a polymerizable function from the group of vinylically unsaturated compounds, which is suitable for building polymer structures by radical means.
  • R 1 preferably represents a vinyl, allyl, methallyl, methylvinyl, acrylic, methacrylic, crotonyl, senecionyl, itaconyl, maleinyl, fumaryl or styryl radical, particularly preferably an acrylic or methacrylic radical.
  • a suitable chemical bridge Y is required to link the silicone-containing polymer chain to the reactive end group R 1 .
  • Preferred bridges Y are -O-, -C (O) -, -C (O) -O-, -S-, -O-CH 2 -CH (O -) - CH 2 OH, -0-CH 2 - CH (OH) -CH 2 -O-, -O-SO 2 -0-, -OS (O) -O-, -PH-, -P (CH 3 ) -, -PO 3 -, -NH-, -N (CH 3 ) -, -O ⁇ d-CsoJalkyl-O-, -O-phenyl-O-, -O-benzyl-O-, -O- (C 5 -C 8 ) cycloalkyl-O-, - O- (CC 5 o) alkenyl-O-, -O- (CH
  • indices w and x in the above formula represent stoichiometric coefficients which are independently 0 to 500, preferably 10 to 250.
  • the distribution of the repeating units over the chain can not only be purely statistical, but can also be block-like, alternating or gradient-like.
  • R 2 stands for an aliphatic, olefinic, cycloaliphatic, arylaliphatic or aromatic (Ci - C 50 ) hydrocarbon radical (linear or branched) or -OH, -NH 2 , -N (CH 3 ) 2 , -R 7 or for the structural unit [-YR 1 ].
  • R 7 stands for a Si-containing group, preferably for -O-Si (CH 3 ) 3 , -O-Si (Ph) 3 , -O-Si (O-Si (CH 3 ) 3 ) 2 CH 3 ) or -O-Si (O-Si (Ph) 3 ) 2 Ph).
  • R 2 represents an element of the group [-YR 1 ], it is a matter of difunctional monomers which can be used to crosslink the polymer structures formed.
  • Formula (I) describes not only vinylically functionalized, silicone-containing polymer species with a typical polymer distribution, but also defined compounds with discrete molecular weights.
  • Vinyldimethoxysilyl endblocked polydimethylsiloxanes with f 10-500, preferably 10 to 250.
  • suitable silicon-containing components can be up to 99.8% by weight, preferably 0.5 to 30% by weight, particularly preferably 1 to 20% by weight.
  • Suitable polymerizable, fluorine-containing components E) are all at least mono-olefinically unsaturated compounds which are capable of radical copolymerization under the reaction conditions chosen in each case.
  • the distribution of the individual fluorine-containing monomers across the resulting polymer chains does not necessarily have to be statistical.
  • the formation of, for example, block (also multiblock) or gradient-like structures is also within the meaning of the invention.
  • Combinations of two or more different fluorine-containing components E) are also possible, it being clear to the expert that monofunctional representatives lead to the formation of comb-shaped structures, whereas di-, tri- or polyfunctional components E) lead to at least partially crosslinked structures.
  • Preferred fluorine-containing components E) are those of the formula (II).
  • R 1 represents a polymerizable function from the group of vinylically unsaturated compounds, which is suitable for building polymer structures by radical means.
  • a suitable chemical bridge Y is required to link the fluorine-containing group to the reactive end group R 1 .
  • Preferred bridges Y are -O-, -C (O) -, -C (0) -O-, -S-, -O-CH 2 -CH (O -) - CH 2 OH, -O-CH 2 - CH (OH) -CH 2 -O-, -O-SO 2 -O-, -OS (O) -O-, -PH-, -P (CH 3 ) -, -PO 3 -, -NH-, -N (CH 3 ) -, -O- (C 1 -C 50 ) alkyl-O-, -O-phenyl-O-, -O-benzyl-O-, -O- (C 5 -C 8 ) cycloalkyl -O-, -O- (-C ⁇ -C 50 ) alkenyl-O-,
  • n, m and o independently of one another are numbers from 0 to 200 and the distribution of the EO and PO units can be statistical or block-shaped.
  • R and s are stoichiometric coefficients that independently represent numbers from 0 to 200.
  • the proportion of fluorine-containing components can be up to 99.8% by weight, preferably 0.5 to 30% by weight, particularly preferably 1 to 20% by weight.
  • the macromonomers F) are at least simple olefinically functionalized polymers with one or more discrete repeating units and a number average molecular weight greater than or equal to 200 g / mol. Mixtures of chemically different macromonomers F) can also be used in the copolymerization.
  • the macromonomers are polymeric structures which are composed of one or more repeating unit (s) and have a molecular weight distribution which is characteristic of polymers.
  • Preferred macromonomers F) are compounds of the formula (III).
  • R 1 represents a polymerizable function from the group of vinylically unsaturated compounds which are suitable for building polymer structures by radical means.
  • R 1 preferably represents a vinyl, allyl, methallyl, methylvinyl, acrylic, methacrylic, crotonyl, senecionyl, itaconyl, maleinyl, fumaryl or styryl radical.
  • a suitable bridging group Y is required to connect the polymer chain to the reactive end group.
  • Preferred bridges Y are -O-, -C (O) -, -C (O) -O-, -S-, -O-CH 2 -CH (O -) - CH 2 OH, -O-CH 2 - CH (OH) -CH 2 O-, -0-SO 2 -0-, -O-SO 2 -O-, -O-SO-O-, -PH-, -P (CH 3 ) -, -PO 3 -, -NH- and -N (CH 3 ) -, particularly preferably -O-.
  • the polymeric middle part of the macromonomer is represented by the discrete repeat units A, B, C and D.
  • the repeating units A, B, C and D are preferably but not limited to: acrylamide, methacrylamide, ethylene oxide, propylene oxide, AMPS, acrylic acid, methacrylic acid, methyl methacrylate, acrylonitrile, maleic acid, vinyl acetate (vinyl alcohol), N-vinylpyrrolidinone, N-vinylcaprolactam , Styrene, 1, 3-butadiene, isoprene, isobutene, diethylacrylamide and diisopropylacrylamide.
  • indices v, w, x and z in formula (III) represent the stoichiometric coefficients relating to the repeating units A, B, C and D.
  • v, w, x and z are independently 0 to 500, preferably 1 to 30, the The sum of the four coefficients must be ⁇ 1 on average.
  • the distribution of the repeating units over the macromonomer chain can be statistical, block-like, alternating or gradient-like.
  • R 2 denotes a linear or branched aliphatic, olefinic, cycloaliphatic, arylaliphatic or aromatic (Ct-Csc -hydrocarbon residue, OH, -NH 2 , -N (CH 3 ) 2 or is equal to the structural unit [-YR 1 ].
  • R 2 is equal to [-YR 1 ]
  • these are difunctional macromonomers which are suitable for crosslinking the copolymers.
  • Particularly preferred macromonomers F) are acrylic or methacrylic monofunctionalized alkyl ethoxylates of the formula (IV).
  • R 3 , R 4 , 5 and R 6 independently of one another are hydrogen or n-aliphatic, iso-aliphatic, olefinic, cycloaliphatic, arylaliphatic or aromatic (-C-C 3 o) hydrocarbon radicals.
  • R 3 and R are preferably H or -CH 3 , particularly preferably H;
  • R 5 is H or -CH 3 ;
  • R ⁇ is an n-aliphatic, iso-aliphatic, olefinic, cycloaliphatic, arylaliphatic or aromatic (C 1 -C 30 ) hydrocarbon radical.
  • v and w are in turn the stoichiometric coefficients relating to the ethylene oxide units (EO) and propylene oxide units (PO), v and w are independently 0 to 500, preferably 1 to 30, the sum of v and w having to be 1 on average.
  • the distribution of the EO and PO units over the macromonomer chain can be statistical, block-like, alternating or gradient-like.
  • Y stands for the bridges mentioned above.
  • Particularly preferred macromonomers F) have the following structure according to formula (IV):
  • Also particularly suitable as macromonomers F) are esters of (meth) acrylic acid with
  • Genapol ® types are products from Clariant, GmbH.
  • thermosensitive properties in the copolymers so that the corresponding polymers have LCST and / or UCST properties.
  • the following non-limiting list represents macromonomers that can produce copolymers with thermosensitive properties.
  • Acrylic or methacrylic fatty alcohol ethoxylate esters such as: (C ⁇ o-C 18 ) fatty alcohol polyglycol ethers with 8 EO units (Genapol ® C-080), Cn-oxo alcohol polyglycol ethers with 8 EO units (Genapol ® UD-080),
  • the molecular weight of the macromonomers F) is preferably 200 g / mol to 10 ⁇ g / mol, particularly preferably 200 to 10 5 g / mol and particularly preferably 200 to 10,000 g / mol. Based on the total mass of the copolymers, suitable macromonomers up to 99.8% by weight can be used. The ranges 0.5 to 30% by weight and 70 to 99.5% by weight are preferably used. Fractions of 1 to 20% by weight and 65 to 95% by weight are particularly preferred.
  • the copolymerization is carried out in the presence of at least one polymeric additive G), the additive G) being added to the polymerization medium in whole or in part in solution before the actual copolymerization.
  • the use of several additives G) is also according to the invention.
  • Crosslinked additives G) can also be used.
  • additives G) or their mixtures only have to be wholly or partly soluble in the chosen polymerization medium.
  • additive G) has several functions. On the one hand, it prevents the formation of over-crosslinked polymer fractions in the copolymer being formed in the actual polymerization step and, on the other hand, additive G) is statistically attacked by active radicals in accordance with the generally known mechanism of graft copolymerization. As a result, depending on the additive G), more or less large amounts of it are incorporated into the copolymers.
  • suitable additives G) have the property of changing the solution parameters of the copolymers formed during the radical polymerization reaction in such a way that the average molecular weights are shifted to higher values. Compared with analog copolymers which were produced without the addition of additives G), those which were produced with the addition of additives G) advantageously show a significantly higher viscosity in aqueous solution.
  • Preferred additives G) are homopolymers and copolymers which are soluble in water and / or alcohols. Copolymers are also to be understood as meaning those with more than two different types of monomers. Particularly preferred additives G) are homo- and copolymers of vinyl acetate, vinyl butyral, vinyl alcohol, N-vinylformamide, N-vinyl acetamide, N-vinyl pyrrolidone, ethylene oxide, propylene oxide, acryloyldimethyl tauric acid, N-vinyl caprolactone, N-vinyl methylacetamide, acrylamide, acrylic acid, methacrylic acid, N-vinyl morpholide, hydroxyethyl methacrylate, diallyldimethylammonium chloride (DADMAC) and / or [2- (methacryloyloxy) ethyl] trimethylammonium chloride (MAPTAC); Polyalkylene glycols and / or alkyl polyglycols
  • additives G are polyvinylpyrrolidones (such as Luviskol K 5 ®, ® K20 and K30 ® from BASF), poly (N-vinylformamides), poly (N-vinylcaprolactams) and copolymers of N-vinylpyrrolidone, N-vinylformamide and / or Acrylic acid, which can also be partially or completely saponified.
  • the molecular weight of the additives G) is preferably 10 2 to 10 7 g / mol, particularly preferably 0.5 * 10 4 to 10 6 g / mol.
  • the amount of polymeric additive G) used is, based on the total mass of the monomers to be polymerized during the copolymerization, preferably 0.1 to 90% by weight, particularly preferably 1 to 20% by weight and particularly preferably 1.5 to 10% by weight .-%.
  • all organic or inorganic solvents which are largely inert with respect to radical polymerization reactions and which advantageously permit the formation of medium or high molecular weights can be used as the polymerization medium.
  • Water is preferred; lower alcohols; preferably methanol, ethanol, propanols, iso-, sec- and t-butanol, particularly preferably t-butanol; Hydrocarbons with 1 to 30 carbon atoms and mixtures of the aforementioned compounds.
  • the polymerization reaction is preferably carried out in the temperature range between 0 and 150 ° C., particularly preferably between 10 and 100 ° C., both under normal pressure and under elevated or reduced pressure.
  • the polymerization can also be carried out under a protective gas atmosphere, preferably under nitrogen.
  • a protective gas atmosphere preferably under nitrogen.
  • chemical polymerization initiators such as organic peroxides, for example benzoyl peroxide, tert-butyl hydroperoxide, Methyl ethyl ketone peroxide, cumene hydroperoxide, dilauroyl peroxide or azo initiators such as azodiisobutyronitrile (AIBN) can be used.
  • organic peroxides for example benzoyl peroxide, tert-butyl hydroperoxide, Methyl ethyl ketone peroxide, cumene hydroperoxide, dilauroyl peroxide or azo initiators such as azodiisobutyronitrile (AIBN)
  • AIBN azodiisobutyronitrile
  • inorganic peroxy compounds such as (NH 4 ) 2 S 2 O 8 , K 2 S 2 Os or H 2 O 2 , optionally in combination with reducing agents (for example sodium bisulfite, ascorbic acid, iron (II) sulfate etc.) or Redox systems which contain an aliphatic or aromatic sulfonic acid (eg benzenesulfonic acid, toluenesulfonic acid etc.) as reducing component.
  • reducing agents for example sodium bisulfite, ascorbic acid, iron (II) sulfate etc.
  • Redox systems which contain an aliphatic or aromatic sulfonic acid (eg benzenesulfonic acid, toluenesulfonic acid etc.) as reducing component.
  • the polymerization reaction can be carried out, for example, as precipitation polymerization, emulsion polymerization, bulk polymerization, solution polymerization or gel polymerization.
  • the synergistic additives can be anionic, cationic, nonionic and / or betaine surfactants. Only the combination of copolymers and synergistic additives leads above unexpected threshold temperatures to the unexpectedly strong formation of thermo-reversible, associative superstructures and thus to a strong increase in viscosity.
  • the person skilled in the art is largely free to select the synergistic additives, but the threshold temperature and the strength of the thermoassociating effect can advantageously be controlled via the choice of the copolymer / additive combinations.
  • Preferred synergistic additives are polyalkylene glycols (preferably PEGs and MPEGs, PO / EO copolymers), alkyl polyglycols (preferably ® Genapol types, Clariant GmbH), alkyl sulfonates, preferably lauryl sulfonate, ether sulfates, preferably alkyl ether sulfates, particularly preferably lauryl ether sulfate, preferably alkyl quats (preferably Behenyl) ® KDMP, Clariant GmbH), cocoamidopropylbetaine (preferably ® Genagen GAB, Clariant), alkyldimethylbetaine (preferably ® Genagen LAB, Clariant GmbH) and mixtures of ether sulfates and betaines. Combinations of two or more representatives of the substance classes mentioned above are of course also in accordance with the invention.
  • synergistic additives are polyalkylene glycols, particularly preferably PEGs and MPEGs, and alkyl polyglycols, particularly preferably the ® GenapoI types.
  • Preferred PEGs and MPEGs are those with molecular weights above 300 g / mol and water-soluble alkyl polyglycols with (C 2 -C 22 ) alkyl chains.
  • the weight ratio between copolymers and synergistic additives is preferably 1: 1000 to 1000: 1, particularly preferably 1: 100 to 100: 1, particularly preferably 1:10 to 10: 1, very particularly preferably 1: 5 to 5: 1.
  • compositions according to the invention preferably contain 0.01 to 50% by weight, particularly preferably 0.1 to 25% by weight, particularly preferably 0.1 to 10% by weight, very particularly preferably 0.1 to 5% by weight, of copolymers of Component I) and 0.01 to 50% by weight, particularly preferably 0.1 to 25% by weight, particularly preferably 0.1 to 10% by weight, very particularly preferably 0.1 to 5% by weight , on synergistic additives of component II).
  • thermoassociating effect of the compositions according to the invention can be controlled very well via the salt content of the compositions.
  • the compositions preferably contain 0.1 to 25% by weight, particularly preferably 1 to 10% by weight, particularly preferably 1 to 5% by weight of salt.
  • Table salt is preferred as the salt.
  • compositions according to the invention have a very wide range of possible uses due to the large structural diversity of the copolymers and the various possible combinations with the synergistic additives, which can be tailored to almost any problem in which interface or surface effects play a role.
  • the compositions according to the invention are preferably oil field chemicals, cosmetic agents, dermatological agents, pharmaceutical agents, washing and cleaning agents and crop protection agents.
  • the invention furthermore relates to the use of the compositions according to the invention as thickeners.
  • the invention furthermore relates to a process for thickening agents, characterized in that the agents are mixed with at least one of the compositions according to the invention.
  • the invention furthermore relates to a process for thickening agents containing at least one of the copolymers, characterized in that the agents are mixed with at least one of the synergistic additives.
  • the invention also relates to a process for thickening agents containing at least one of the synergistic additives, characterized in that the agents are mixed with at least one of the copolymers.
  • compositions according to the invention or the individual components I) and II) can also be used in concentrated form, if appropriate also as a mixture of pure substances or pure substances.
  • the amounts used are preferably such that the final concentrations of
  • compositions correspond to the preferred values indicated above.
  • Examples 1 to 9 relate to the copolymers.
  • the copolymers form thermosensitive structures that allow the formation of associative structures above certain threshold temperatures.
  • the polymer was tert in the precipitation process. Butanol made. The monomers were initially charged in t-butanol, the reaction mixture was rendered inert, and the reaction was then initiated after heating by adding DLP. The polymer was isolated by suction extraction of the solvent and subsequent vacuum drying.
  • the polymer was tert in the precipitation process. Butanol made. The monomers were initially charged in t-butanol, the reaction mixture was rendered inert, and the reaction was then initiated after heating by adding DLP. The Polymer was isolated by suctioning off the solvent and then vacuum drying.
  • the polymer was made in water by the gel polymerization process.
  • the monomers were dissolved in water, the reaction mixture was rendered inert, and the reaction was then initiated after heating by adding sodium peroxodisulfate.
  • the polymer gel was then crushed and the polymer isolated by vacuum drying.
  • the polymer was made in water by the emulsion process.
  • the monomers were emulsified in a water / cyclohexane using ® Span 80, the reaction mixture was rendered inert using N 2 and the reaction was then started after heating by adding sodium peroxodisulfate.
  • the polymer emulsion was then evaporated (cyclohexane acts as a tug for water), thereby isolating the polymer.
  • the polymer was tert in the precipitation process. Butanol made. The monomers were initially introduced into t-butanol, the reaction mixture was rendered inert, and the reaction was then initiated after heating by adding AIBN. The polymer was isolated by suction extraction of the solvent and subsequent vacuum drying.
  • the polymer was made by the solution method in water. The monomers were dissolved in water, the reaction mixture was rendered inert, and the reaction was then initiated by a suitable redox couple after heating. The polymer solution was then evaporated and the polymer was then isolated by vacuum drying.
  • the polymer was tert in the precipitation process. Butanol made. The monomers were initially introduced into t-butanol, the reaction mixture was rendered inert, and the reaction was then initiated after heating by adding AIBN. The polymer was isolated by suction extraction of the solvent and subsequent vacuum drying.
  • the polymer was tert in the precipitation process. Butanol made. The monomers were initially charged in t-butanol, the reaction mixture was rendered inert, and the reaction was then initiated after heating by adding DLP. The polymer was isolated by evaporation of the solvent and subsequent vacuum drying.
  • the polymer was made in an isopropanol / water mixture by the solution method.
  • the monomers were placed in isopropanol / water, the reaction mixture was rendered inert, and the reaction was then initiated after heating by adding ABAH.
  • the polymer was isolated by evaporation of the solvent mixture and subsequent vacuum drying.
  • Examples 10 to 18 show the effect of synergistic additives on the viscosity behavior of selected copolymers. This shows that the threshold temperature and the strength of the thermoassociating effect can be controlled within wide limits.
  • Examples 10 and 15 are comparative examples. The viscosities were determined up to 100 ° C with a Brookfield viscometer and up to 200 ° C with a Fann 50 viscometer. For simplification, only the temperatures at which there is a significant increase in viscosity are given has been observed (column T V j S k) and the maximum observed viscosity (column maximum viscosity)
  • the ® Genapol types are alkyl polyglycols from Clariant GmbH.
  • Comparative Examples 10 and 15 show that without the addition of a synergistic additive, no measurable thermoassociative effect is observed.
  • Examples 10 to 13 document the influence of the amount of synergistic additive used on the threshold temperature of the thermal association and on its maximum viscosity.
  • Example 14 shows that different additives change the threshold temperature as well as the viscosity for a given copolymer.
  • Example 18 illustrates how the thermoassociative properties can be controlled via the salt content of the compositions.

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Abstract

L'invention concerne une composition renfermant des copolymères à base d'acide acryloyldiméthyl-amino-éthylsulfonique, ainsi que des additifs synergiques, sélectionnés parmi des agents tensioactifs anioniques, cationiques, non-ioniques et/ou bétaïniques. Les compositions présentent un comportement marqué d'association thermique et conviennent remarquablement bien comme épaississants.
EP01998569A 2000-12-01 2001-11-28 Compositions renfermant des copolymeres a base d'acide acryloyldimethyl-amino-ethylsulfonique et des additifs synergiques Withdrawn EP1354001A2 (fr)

Applications Claiming Priority (33)

Application Number Priority Date Filing Date Title
DE10059831 2000-12-01
DE10059827A DE10059827A1 (de) 2000-12-01 2000-12-01 Kosmetische und dermatologische Haarbehandlungsmittel
DE10059823A DE10059823A1 (de) 2000-12-01 2000-12-01 Deodorantien und Antiperspirantien
DE10059826 2000-12-01
DE10059823 2000-12-01
DE10059825A DE10059825A1 (de) 2000-12-01 2000-12-01 Verwendung von kammförmigen Copolymeren auf Basis von Acryloyldimethyltaurinsäure in kosmetischen, pharmazeutischen und dermatologischen Mitteln
DE10059822A DE10059822A1 (de) 2000-12-01 2000-12-01 Saure kosmetische, pharmazeutische und dermatologische Mittel
DE10059833 2000-12-01
DE10059822 2000-12-01
DE10059833A DE10059833A1 (de) 2000-12-01 2000-12-01 Fluormodifizierte Kammpolymere auf Basis von Acryloyldimethylaurinsäure
DE10059818 2000-12-01
DE10059824A DE10059824A1 (de) 2000-12-01 2000-12-01 Elektrolythaltige kosmetische, pharmazeutische und dermatologische Mittel
DE10059819 2000-12-01
DE10059821A DE10059821A1 (de) 2000-12-01 2000-12-01 Tensidfreie kosmetische, dermatologische und pharmazeutische Mittel
DE10059829A DE10059829A1 (de) 2000-12-01 2000-12-01 Gepfropfte Kammpolymere auf Basis von Acryloyldimethyltaurinsäure
DE10059825 2000-12-01
DE10059828 2000-12-01
DE10059819A DE10059819A1 (de) 2000-12-01 2000-12-01 Tensidhaltige kosmetische, dermatologische und pharmazeutische Mittel
DE10059832 2000-12-01
DE10059824 2000-12-01
DE10059826A DE10059826A1 (de) 2000-12-01 2000-12-01 Kosmetische, pharmazeutische und dermatologische Mittel
DE10059832A DE10059832A1 (de) 2000-12-01 2000-12-01 Gepfropfte Copolymere auf Basis von Acryloyldimethyltaurinsäure
DE10059821 2000-12-01
DE10059829 2000-12-01
DE10059818A DE10059818A1 (de) 2000-12-01 2000-12-01 Dekorative kosmetische und dermatologische Mittel
DE10059831A DE10059831A1 (de) 2000-12-01 2000-12-01 Siliziummodifizierte Kammpolymere auf Basis von Acryloyldimethyltaurinsäure
DE10059830A DE10059830A1 (de) 2000-12-01 2000-12-01 Kationisch modifizierte Kammpolymere auf Basis von Acryloyldimethyltaurinsäure
DE10059827 2000-12-01
DE10059828A DE10059828A1 (de) 2000-12-01 2000-12-01 Kammförmige Copolymere auf Basis von Acryloyldimethyltaurinsäure
DE10059830 2000-12-01
DE2001127876 DE10127876A1 (de) 2001-06-11 2001-06-11 Zusammensetzungen, enthaltend Copolymere auf Basis von Acryloyldimethyltaurinsäure und synergistische Additive
DE10127876 2001-06-11
PCT/EP2001/013859 WO2002044230A2 (fr) 2000-12-01 2001-11-28 Compositions renfermant des copolymeres a base d'acide acryloyldimethyl-amino-ethylsulfonique et des additifs synergiques

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US7053146B2 (en) 2006-05-30
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JP2002327102A (ja) 2002-11-15

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