EP1962908A2 - Utilisation de copolymeres blocs de lactame polyvinylique et d'oxyde de polyalkylene comme solubilisants dans des composes peu solubles dans l'eau - Google Patents

Utilisation de copolymeres blocs de lactame polyvinylique et d'oxyde de polyalkylene comme solubilisants dans des composes peu solubles dans l'eau

Info

Publication number
EP1962908A2
EP1962908A2 EP06830233A EP06830233A EP1962908A2 EP 1962908 A2 EP1962908 A2 EP 1962908A2 EP 06830233 A EP06830233 A EP 06830233A EP 06830233 A EP06830233 A EP 06830233A EP 1962908 A2 EP1962908 A2 EP 1962908A2
Authority
EP
European Patent Office
Prior art keywords
use according
preparations
water
fatty acid
soluble
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Withdrawn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
EP06830233A
Other languages
German (de)
English (en)
Inventor
Ronald Frans Maria Lange
Nathalie Bouillo
Ingo MÜNSTER
Klemens Mathauer
Kathrin MEYER-BÖHM
Rainer Dobrawa
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.)
BASF SE
Original Assignee
BASF SE
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
Application filed by BASF SE filed Critical BASF SE
Priority to EP06830233A priority Critical patent/EP1962908A2/fr
Publication of EP1962908A2 publication Critical patent/EP1962908A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/288—Synthetic resins, e.g. polyvinylpyrrolidone
    • 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
    • A61K8/90—Block 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
    • 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

Definitions

  • solubilisates produced are characterized in that the poorly water-soluble or water-insoluble substance is present in the molecular associates of the surface-active compounds which form in aqueous solution - the so-called micelles - in colloidal solution.
  • the resulting solutions are stable single-phase systems that appear optically clear to opalescent and can be manufactured without energy input.
  • solubilizers can improve the appearance of cosmetic formulations and of food preparations by making the formulations transparent.
  • the bioavailability and thus the effect of drugs can be increased by using solubilizers.
  • the main solubilizers for pharmaceutical drugs and cosmetic active ingredients are surfactants such as ethoxylated (hydrogenated) castor oil, ethoxylated
  • Sorbitan fatty acid ester or ethoxylated hydroxystearic acid used.
  • solubilizers described have a number of disadvantages in terms of application technology.
  • the known solubilizers have only a slight solubilizing effect for some poorly soluble drugs such as clotrimazole.
  • solubilizers known hitherto are mostly liquid or semi-solid compounds which, owing to the fact that they have less favorable processing properties.
  • WO 94/20073 discloses polyvinylpyrrolidone block copolymers and their use as wall material for liposomes.
  • WO 03/072158 discloses polyvinylpyrrolidone block copolymers and their use in medical technology, for example for surface modification of catheters. The hydroxyl functionalization of polyvinylpyrrolidone with isopropoxyethanol is described for the preparation of the block copolymers. The task was to provide new solubilizers for pharmaceutical, cosmetic, food technology and agrotechnical applications.
  • the object has been achieved according to the invention by using polyvinyl acetate-polyalkylene oxide block copolymers as solubilizers for substances which are sparingly soluble in water.
  • the polyvinyl lactam block is referred to as the A block and the polyalkylene oxide block as the B block.
  • the polyvinyl lactams are functionalized with hydroxyl groups at the beginning and / or at the end of the chain.
  • the OH functionalization can be achieved either via the radical starter or via a controller. Functionalization via the radical starter takes place at the beginning of the chain, functionalization via the controller at the end of the chain.
  • at least one radical initiator carrying hydroxyl groups or one regulator carrying hydroxyl groups must therefore be used in the polymerization of the polyvinyllactam prepolymer. If B-A-B block copolymers are to be produced, radical initiators and regulators must carry hydroxyl groups.
  • N-vinyl lactams are N-vinyl pyrrolidone, N-vinyl caprolactam or N-vinyl piperidone or mixtures thereof. N-vinylpyrrolidone is preferably used.
  • Suitable non-aqueous solvents are, for example, alcohols, such as methanol, ethanol, n-propanol and isopropanol, and glycols, such as ethylene glycol and glycerin.
  • Alcohols such as methanol, ethanol, n-propanol and isopropanol
  • glycols such as ethylene glycol and glycerin.
  • Acetic acid esters such as, for example, ethyl acetate or butyl acetate are also suitable as solvents.
  • the polymerization is preferably carried out at temperatures from 60 to 100.degree.
  • Free radical initiators are used as free radical initiators to initiate the polymerization.
  • the amounts of initiator or initiator mixtures used, based on the monomer used, are between 0.01 and 10% by weight, preferably between 0.3 and 5% by weight.
  • organic and inorganic peroxides such as sodium persulfate or azo starters such as azo-bis-isobutyronitrile, azo-bis- (2-amidopropane) dihydrochloride or 2,2'-azo-bis- (2-methyl- butyronitrile).
  • Peroxidic initiators are, for example, dibenzoyl peroxide, diacetyl peroxide, succinyl peroxide, tert-butyl perpivalate, tert-butyl 2-ethylhexanoate, tert-butyl permaleinate, bis- (tert-butyl peroxy) cyclohexane, tert-butyl peroxi-isopropyl carbonate .-Butyl peracetate, 2,2-bis (tert-butyl peroxy) butane, dicumyl peroxide, di-tert-amyl peroxide, di-tert-butyl peroxide, p-menthane hydroperoxide, pinane hydroperoxide, cumene hydroperoxide, tert-butyl hydroperoxide, hydrogen peroxide and mixtures of the initiators mentioned.
  • the initiators mentioned can also be used in combination with redox components such as ascorbic acid.
  • the radical polymerization can optionally take place in the presence of emulsifiers, optionally further protective colloids, optionally buffer systems and optionally subsequent pH adjustment using bases or acids.
  • Suitable molecular weight regulators are hydrogen sulfide compounds such as alkyl mercaptans, for example n-dodecyl mercaptan, tert-dodecyl mercaptan, thioglycolic acid and their esters, mercaptoalkanols such as mercaptoethanol.
  • alkyl mercaptans for example n-dodecyl mercaptan, tert-dodecyl mercaptan, thioglycolic acid and their esters, mercaptoalkanols such as mercaptoethanol.
  • Other suitable regulators are mentioned, for example, in DE 197 12 247 A1, page 4.
  • the required amount of the molecular weight regulator is in the range from 0 to 5% by weight, based on the amount of monomers to be polymerized, in particular 0.05 to 2% by weight, particularly preferably 0.1 to 1.5% by weight.
  • Mercaptoethanol is preferably used.
  • the monomer or a monomer mixture or the monomer (s) emulsion are introduced together with the initiator, which is usually present in solution, in a stirred reactor at the polymerization temperature (batch process), or, if appropriate, continuously or in several successive stages in the polymers. onsreaktor dosed (feed process).
  • the reactor in addition to water (in order to allow the reactor to be stirred), in addition to water, in part, rarely the total amount intended for the polymerization, of the starting materials, such as emulsifiers, protective colloids, monomers, regulators, etc., before the actual polymerization begins. or partial quantities of the feeds (generally monomer or emulsion feed and initiator feed) are filled.
  • Polyalkylene glycols are preferably suitable as polyalkylene oxides.
  • the polyalkylene glycols can have molecular weights of 300 to 25,000 D [Dalton], preferably 1,000 to 15,000 D, particularly preferably 1,000 to 10,000 D. The molecular weights are determined on the basis of the hydroxyl number measured in accordance with DIN 53240.
  • Polyethylene glycols are considered as particularly preferred polyalkylene glycols.
  • Polybutylene glycols obtained from 2-ethyloxirane or 2,3-dimethyloxirane.
  • Suitable polyethers are also random or block-like copolymers of polyalkylene glycols obtained from ethylene oxide, propylene oxide and butylene oxides, such as, for example, polyethylene glycol-polypropylene glycol block copolymers.
  • the block copolymers can be of the AB or ABA type.
  • the preferred polyalkylene glycols also include those which are substituted on one of the two OH end groups.
  • Alkyl, aryl or aralkyl radicals having 1 to 30 C atoms are suitable as substituents.
  • Suitable aryl radicals are phenyl and naphthyl radicals.
  • suitable aralkyl radicals are, for example, benzyl radicals.
  • Suitable alkyl radicals are branched or unbranched, open-chain or cyclic d to C22 alkyl radicals.
  • Suitable cycloalkyl radicals are, for example, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radicals, which can optionally be substituted by one or more C1-C4-alkyl radicals.
  • Ci-Cis-alkyl radicals for example methyl, ethyl, n-butyl, isobutyl, pentyl, hexyl, octyl, nonyl, decyl, dodecyl, tridecyl or octadecyl radicals, are preferred.
  • Such polyalkylene oxides are either easy to manufacture or commercially available.
  • the polyalkylene oxides are reacted in an equimolar amount, based on the hydroxyl groups in the polyalkylene oxide and in the vinyl lactam prepolymer.
  • the amount of OH groups present can, if necessary, in a manner known per se to the person skilled in the art respectively.
  • For the determination of the hydroxyl number see, for example, Römpp Chemie Lexikon, 9th edition, 1990.
  • polyalkylene oxides are used in individual cases depends on the desired block structure. If a B-A-B type or an A-B type is desired, a polyalkylene oxide can be used, the OH group of which is substituted at one end. If an A-B-A type is desired, only a polyalkylene oxide can be used which has free OH groups at both ends.
  • the coupling of vinyl lactam polymers and polyalkylene oxides takes place by reaction with diisocyanates, the polyalkylene oxide being coupled to the vinyl lactam copolymer via urethane groups by reaction with the hydroxyl groups of the vinyl lactam copolymer. Either the vinyl lactam polymer or the polyalkylene oxide can first be reacted with the diisocyanate.
  • the coupling takes place via polyalkylene oxides functionalized with isocyanate groups as end groups.
  • the polyalkylene oxide is first reacted with the diisocyanate and then the functionalized polyalkylene oxide is reacted with the vinyl lactam polymer.
  • Suitable diisocyanates are compounds of the general formula OCN-R-NCO, where R can mean aliphatic, alicyclic or aromatic radicals, which can also be substituted by alkyl radicals.
  • symmetrical diisocyanates such as hexamethylene diisocyanate or 4,4'-methylene di (phenyl isocyanate) are also suitable.
  • Isophorone diisocyanate is preferably used.
  • the reaction with the diisocyanate is preferably carried out in an organic solvent such as ketones, for example acetone, furthermore dimethyl sulfoxide, dimethylformamide, or generally aprotic-polar organic solvents or mixtures of such solvents.
  • the reaction is usually carried out at elevated temperatures, the temperature also depending on the boiling point of the solvent selected.
  • the reaction of the diisocyanate with the first component can be done at 20 to 50 ° C, but if desired also up to 100 ° C.
  • the reaction of the second isocyanate group can take place at temperatures from 50 to 100 ° C.
  • the reaction is preferably carried out in equimolar amounts, which means that the quantitative ratio is chosen so that 1 mol of diisocyanate is used per mole of hydroxyl group to be reacted. If the vinyl lactam polymer is OH-functionalized by a regulator, the diisocyanate is converted to the regulator in an equimolar amount. If the vinyl lactam polymer is OH-functionalized via a radical initiator, 2 moles of diisocyanate are used per mole of radical initiator.
  • Suitable catalysts are, for example, organometallic compounds such as organotitanium compounds or zinc compounds such as dibutyltin dilaurate or tin octoate, and also bases such as 1,4-diaza (2,2,2) bicyclooctane or tetramethylbutanediamine.
  • the catalyst can be used in amounts of 0.05 to 0.2 Mol, preferably 0.1 to 0.14 mol, are used per mole of diisocyanate.
  • the reaction is usually carried out at elevated temperatures in the range from 50 to 100.degree. Which temperature is selected depends on the type of organic solvent used. The solvent can then be removed by distillation.
  • the initial charge was heated to 80 ° C. at a stirrer speed of 60 rpm, 1.6 kg of feed 2 g of feed 2 were added and the mixture was polymerized for 15 minutes. Then the remaining amounts of feed 1 and feed 2 were added over a period of 2 hours. Feed 3 was then added as a batch and post-polymerization was carried out at 80 ° C. for 3 hours. The mixture was then cooled to 30 ° C. and the polymer was isolated by spray drying.
  • the OH numbers of the polyalkylene oxides and vinyl lactam prepolymers are determined by acetylating the hydroxyl groups with acetic anhydride and then titrating the acetic acid formed with base (DIN 53240 and DIN 16945, see Römpp, 9th edition).
  • the isocyanate value was determined titrimetrically: 1 g of the product was dissolved in 20 ml of a 0.1 molar solution of dibutylamine in toluene and back-titrated with 0.1 molar hydrochloric acid using bromophenol blue as an indicator.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Toxicology (AREA)
  • Plant Pathology (AREA)
  • Nutrition Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Epidemiology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne l'utilisation de copolymères blocs de lactame polyvinylique et d'oxyde de polyalkylène comme solubilisants pour des substances peu solubles dans l'eau.
EP06830233A 2005-12-09 2006-11-30 Utilisation de copolymeres blocs de lactame polyvinylique et d'oxyde de polyalkylene comme solubilisants dans des composes peu solubles dans l'eau Withdrawn EP1962908A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP06830233A EP1962908A2 (fr) 2005-12-09 2006-11-30 Utilisation de copolymeres blocs de lactame polyvinylique et d'oxyde de polyalkylene comme solubilisants dans des composes peu solubles dans l'eau

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP05111923 2005-12-09
EP06830233A EP1962908A2 (fr) 2005-12-09 2006-11-30 Utilisation de copolymeres blocs de lactame polyvinylique et d'oxyde de polyalkylene comme solubilisants dans des composes peu solubles dans l'eau
PCT/EP2006/069129 WO2007065846A2 (fr) 2005-12-09 2006-11-30 Utilisation de copolymeres blocs de lactame polyvinylique et d'oxyde de polyalkylene comme solubilisants dans des composes peu solubles dans l'eau

Publications (1)

Publication Number Publication Date
EP1962908A2 true EP1962908A2 (fr) 2008-09-03

Family

ID=37758751

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06830233A Withdrawn EP1962908A2 (fr) 2005-12-09 2006-11-30 Utilisation de copolymeres blocs de lactame polyvinylique et d'oxyde de polyalkylene comme solubilisants dans des composes peu solubles dans l'eau

Country Status (5)

Country Link
US (1) US20080300320A1 (fr)
EP (1) EP1962908A2 (fr)
JP (1) JP2009523119A (fr)
CN (1) CN101325976A (fr)
WO (1) WO2007065846A2 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005053066A1 (de) * 2005-11-04 2007-05-10 Basf Ag Verwendung von Copolymeren als Solubilisatoren für in Wasser schwerlöslichen Verbindungen
WO2007065845A1 (fr) * 2005-12-09 2007-06-14 Basf Se Copolymeres a base de copolymeres de n-vinyllactame a modification polyalkylene-oxyde
WO2009040248A1 (fr) * 2007-09-27 2009-04-02 Basf Se Agents améliorant la systémicité
EP2503878B1 (fr) * 2009-11-27 2015-01-28 Basf Se Polyurée dendritique pour la solubilisation de substances actives difficilement solubles
WO2011110481A1 (fr) * 2010-03-08 2011-09-15 Basf Se Composition comprenant une substance active et un polymère d'ester vinylique greffé par un oxyde de polyalkylène
CN103347931B (zh) 2011-02-28 2016-02-17 巴斯夫欧洲公司 制备用于药物剂型的稳定保护性衣层的粉末包衣剂
EP2636403A1 (fr) 2012-03-09 2013-09-11 Basf Se Fabrication de revêtements de protection pharmaceutiques ayant une bonne résistance en milieu neutre
US20130236505A1 (en) 2012-03-09 2013-09-12 Basf Se Production Of Pharmaceutical Protective Coatings With Good Resistance In A Neutral Environment

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Also Published As

Publication number Publication date
US20080300320A1 (en) 2008-12-04
CN101325976A (zh) 2008-12-17
WO2007065846A3 (fr) 2007-11-29
WO2007065846A2 (fr) 2007-06-14
JP2009523119A (ja) 2009-06-18

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