WO1989004163A1 - Composition de lotion - Google Patents

Composition de lotion Download PDF

Info

Publication number
WO1989004163A1
WO1989004163A1 PCT/GB1988/000962 GB8800962W WO8904163A1 WO 1989004163 A1 WO1989004163 A1 WO 1989004163A1 GB 8800962 W GB8800962 W GB 8800962W WO 8904163 A1 WO8904163 A1 WO 8904163A1
Authority
WO
WIPO (PCT)
Prior art keywords
groups
composition according
hair
polydiorganosiloxane
silane
Prior art date
Application number
PCT/GB1988/000962
Other languages
English (en)
Inventor
Annemieke Constantia Maria Donkers
Shirley Elizabeth Wright
Original Assignee
Dow Corning Limited
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 Dow Corning Limited filed Critical Dow Corning Limited
Publication of WO1989004163A1 publication Critical patent/WO1989004163A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • This invention is concerned with conditioning compo ⁇ sitions and is particularly concerned with conditioning compositions for human hair.
  • compositions intended for use for example, on human hair with a view to conditioning the hair, i.e. imparting to the hair one or more desirable properties, for example, ease of combing or detangliug of wet hair, or ease of combing, lustre, a fullness or body accompanied by a certain liveliness, manageability and avoidance of static in the dried hair.
  • Such compositions may take the form, for example, of shampoos, conditioners or rinses, and all such compositions are referred to herein as conditioning compositions.
  • surfac ⁇ tants such as stearyldimethylbenzylammoniu chloride, cetyltrimethylammonium bromide and dimethylbis(hydrogenated tallow)ammonium chloride, for their hair conditioning properties.
  • surfac ⁇ tants such as stearyldimethylbenzylammoniu chloride, cetyltrimethylammonium bromide and dimethylbis(hydrogenated tallow)ammonium chloride
  • hair treating compositions comprising certain silanes or poly ⁇ siloxanes having quaternary ammonium groups in combination with polysiloxanes having certain amino groups are desc ⁇ ribed and claimed in G.E. patent specification 2 144 329.
  • These compositions are effective to provide a variety of desirable properties to shampooed hair but it is recom ⁇ mended that they are not used frequently on the hair due to a tendency of the polysiloxanes having amino groups to adhere strongly to the hair for a considerable time and to resist removal during normal shampooing.
  • the polysi ⁇ loxanes having siloxane units including quaternary ammonium salt groups generally require a series of preparation steps and their manufacture can be costly.
  • a conditioning composition capable of imparting a range of beneficial properties to human hair may be provided by an aqueous composition based on certain selected polydiorganosiloxanes and selected silanes having quaternary ammonium salt groups.
  • the present invention provides in one of its aspects a conditioning composition formed by admixture of compo ⁇ nents comprising (a) an aqueous emulsion of a polydiorgano- siloxane having units of the general formula R'R ⁇ SiO ⁇ and R SiO, .
  • R is selected from the group consisting " 2 "" of alkyl and aryl groups having no more than 8 carbon atoms
  • R' is selected from R groups and hydroxyl and a. is an integer with a value of from 0 to 2, with (b) a quater- nary ammonium compound characterised in that the quaternary ammonium compound is a quaternary ammonium silane of the general (ii) R 3 3 SiR 4 + (R 5 ).
  • R 3 in which each R 3 is selected from the group consisting of alkyl groups having up to 5 carbon atoms in their chain, a hydroxyl group, alkoxy groups, alkoxyalkoxy groups having less than 12 carbon atoms, and a trimethylsiloxy group
  • R represents a divalent aliphatic hydrocarbon group having from 2 to 10 carbon atoms in its chain linking the silicon and nitrogen atoms and composed of carbon, hydrogen, optionally oxygen in the form of hydroxyl and optionally oxygen in the form of ether link
  • Component (a) is an oil-in-water emulsion of a poly- diorganosiloxane compound.
  • Suitable polydiorganosiloxanes are those which can be provided in emulsions either by emulsion polymerisation or by mechanical emulsification.
  • Preferred polydiorganosiloxanes are linear polymers wherein a_ has a value of 2 and which have the average general formula (i) R'SiR ⁇ EOSiRg] ORgSiR', wherein-R and R * are as defined above and n is an integer.
  • the groups R are preferably at least predominantly methyl but may include phenyl or other aromatic groups as aforesaid.
  • Polydi ⁇ organosiloxanes in which at least substantially ail R groups are methyl groups preferably have a viscosity of at least 1000 mm 2 /s at 25°C and preferably less than about 300,000 mm 2 /s; preferably they have a viscosity of from 10,000 to about 200,000 mm 2 /s at 25°C, most preferably from 12,500 to 100,000 mm 2 /s at 25°C.
  • Polydiorganosiloxanes in which more than about 10% of the R groups are phenyl and less than 90% are alkyl groups preferably have a viscosity in the range of about 10 to about 1000 mm 2 /s at 25°C.
  • the emulsion, in which the polydiorganosiloxane is provided may be made by mechanically emulsifying a polydiorganosiloxane of required viscosity according to methods which are well known in the art.
  • Polydiorganosiloxanes which may be thus emulsified are well known, and many are commercially avail ⁇ able. They may be prepared for example by the hydrolysis of halogenosilanes or by equilibration of cyclic diorgano- siloxanes with monofunctional silanes.
  • the emulsion may be made by emulsion polymerisation, as is described for example in British Patent Specification 992 087.
  • Emulsions made by the emulsion polymerisation technique are usually more stable and have a smaller particle size than the emulsions which are made by mechanical emulsification.
  • Polydiorgano ⁇ siloxanes made via the emulsion polymerisation technique usually have a structure in which each R" represents a hydroxyl group.
  • Emulsions which are useful in the present invention may have a solids content of up to about 75%, but preferably contain from about 10% to about 40% b ⁇ weight polydiorganosiloxane.
  • the amount of emulsion (a) in a composition according to the invention is such that up to
  • component (b) is a quaternary ammonium silane of the
  • At least one of the groups R is an alkyl group, preferably a methyl group and up to two of 3 the groups R. are alkoxy groups,preferably methoxy groups.
  • the quaternary ammonium silanes are known materials and may be prepared in various ways, for example as disclosed in G.B. patent specifications 1 117 592 and 2 107 715. We prefer to prepare them from the corresponding tertiary amine and chlorosilane, trialkyl chlorosilanes are pref ⁇ erred over those containing readil ⁇ 7 hydrolysable groups, for example alkoxy and alkoxyalkoxy groups, thus avoiding production of disiloxanes and trisiloxanes during conversion of the silane to the quaternarv ammonium salts.
  • the group R may be for example -(CE -.
  • R may be chosen for example from methyl, ethyl, propyl, decyl, dodecyl, tetradecyl and octadecyl. Preferably one only of •
  • the groups R has a longer aliphatic chain.
  • two of the groups R are methyl groups and one of them has an aliphatic chain having on average about 12 to 14 chain carbon atoms.
  • the nature of the anion X ⁇ influences the solubility of the silane; whilst many organic a d inorganic anions may be employed depending on the surfactant used in the emulsion, for example acetate, bromide and iodide, we prefer to employ the chloride ion.
  • Suitable quaternary ammonium silanes include those of the formulae (CH 3 0) 2 CH 3 Si(CH 2 ) 3 N + (CH 3 ) 2 (C 13 H 27 )Cl ⁇ , (CH 3 0) 2 CH 3 Si(CH 2 ) 3 N + CH 3 C 12 H 25 ) 2 Cl ⁇ , (CH 3 ) 3 Si(CH 2 ) 3 Ef (CK 3 ) 2 (C 13 H 27 )C1 " , (CE 3 OCH 2 CH 2 0)CCH 3 0) 2 .Si(CH 2 ) 3 N + (CH 3 ) 2 (C 18 H 37 )Cl " , (CH 3 SiO) 3 Si(CH 2 ) 3 + (CH 3 ) 2 (C 13 H 27 )Cl " ,
  • Component (b) of a composition according to the invention is water soluble and may be readily incorporated with- component (a) by a simple mixing procedure.
  • Components (a) and (b) when mixed in the required propor ⁇ tions provide an aqueous emulsion which may be readily supplied to the hair.
  • the emulsion may be formulated into a form in which it is stable for a short period but unless appropriate surfactants and stabilizers are included in the formulation, the emulsion is likely to be unstable in storage and it is then preferable to store the components separately and to mix them in desired proportions shortly before use.
  • a composition according to the invention may, and preferably does ' , contain at least one surfactant which functions to stabilize the emulsion and maintain the poly ⁇ diorganosiloxane in the dispersed state in the aqueous medium.
  • the nature of the surfactant is not critical; preferably it is cationic or nonionic.
  • Examples of surfac- tants are aliphatic fatty amines and their derivatives e.g. octadecylamine acetate and quaternary ammonium halides, sulphonic acids e.g. dodecyl benzene sulphonic acid, ethylene oxide adducts of octyl or nonyl phenols e.g.
  • octylphenoxypolyethoxyethanol condensation products of aliphatic alcohols and ethylene oxide, monoesters of alcohols and fatty acids e.g. sodium lauryl sulphate glyceryl stearate, sorbitan monolaurate and polyox ⁇ - ethylenemonostearate, and polyvinyl alcohol.
  • the surfactant component is generally employed in amounts of about 0.01% to about 5% by weight of the composition.
  • the silane (b) is preferably present in excess of about 0.25% by weight of the composition in order to achieve the desired low level of static for the treated hair. Larger proportions may be used to give increased static control but it is generally not necessary to employ more than about 5% of the silane in the composition.
  • the polydiorgano- siloxane provided in component (a) is present principally to contribute softness and related properties. When using the lower molecular weight polydiorganosiloxanes, the amount employed is greater than when the higher molecular weight polydiorganosiloxanes are employed.
  • the composition may include other ingredients as stabilisers, for example non-ionic surfactants as afore ⁇ said, thickeners e.g. carboxymethyl cellulose, hydroxy- propyl cellulose and guar gum, colorants, perfumes, bacte- ricides, solvents, preservatives, and conventional hair conditioning ingredients e.g. handle modifiers eg fatty acid salts esters and ethers and long chain alkyl alcohols, waxes, oils and organic quaternary compounds.
  • stabilisers for example non-ionic surfactants as afore ⁇ said, thickeners e.g. carboxymethyl cellulose, hydroxy- propyl cellulose and guar gum, colorants, perfumes, bacte- ricides, solvents, preservatives, and conventional hair conditioning ingredients e.g. handle modifiers eg fatty acid salts esters and ethers and long chain alkyl alcohols, waxes, oils and organic quaternary compounds.
  • composition may be formulated as a shampoo by the inclusion of suitable sequestering agents and detergents for the cleaning of hair, for example those based on fatty alcohols e.g. lauryl and myristyl alcohols, or fatty alcoholethoxylate ⁇ .
  • suitable sequestering agents and detergents for the cleaning of hair, for example those based on fatty alcohols e.g. lauryl and myristyl alcohols, or fatty alcoholethoxylate ⁇ .
  • suitable sequestering agents and detergents for the cleaning of hair, for example those based on fatty alcohols e.g. lauryl and myristyl alcohols, or fatty alcoholethoxylate ⁇ .
  • suitable sequestering agents and detergents for the cleaning of hair, for example those based on fatty alcohols e.g. lauryl and myristyl alcohols, or fatty alcoholethoxylate ⁇ .
  • detergents are sodium lauryl sulphate, sodium lauryl ether sulphate, ammoni
  • a process for the treatment of hair which comprises applying thereto a composition according to the invention.
  • the treatment is preferably done after the hair has been shampooed and the shampoo rinsed off, but it may be done simultaneously with the shampooing of the hair, the latter being more appropriate when a composition according to the invention is formulated as as shampoo.
  • compositions according to the present invention allow the formulation of hair conditioning compositions as a shampoo or as a rinse for treating shampooed hair, using a minimal number of ingredients in comparatively small quantities, still providing a desirable conditioning effect on human hair and, in particular, ensuring a low level of static electricity in the treated hair.
  • the composition may be easily washed from the treated hair in a normal shampooing of the hair.
  • a first aqueous emulsion was prepared by emulsion polymerisation of cyclic polydimethylsiloxanes in presence of an alkyl benzene sulphonic acid to provide an emulsion of 35 parts of a first polydiorganosiloxane namely a dimethylhydroxysiloxy end blocked polydimethylsiloxane having a viscosity at 25°C of 100,000 mm 2 /s, dispersed in water and neutralised with triethanolamine, together with minor amounts (i.e. less than 5% of the composition, and preferably less than 3% of the composition) of preservative and a non-ionic emulsifier as stabilizer and 53 parts water.
  • a second aqueous emulsion of 35 parts of a second polysiloxane namely trimethylsiloxy end blocked polydi ⁇ methylsiloxane having a viscosity at 25°C of 12,500 mm 2 /s was prepared by emulsion polymerisation in presence of an alkyl benzene sulphonic acid in water and neutralised with triethanolamine, together with minor amounts of preserva ⁇ tive and a non-ionic emulsifier as stabilizer and 53 parts water.
  • compositions were also prepared using components as shown in Table 1.
  • the resulting compositions were used to treat swatches of virgin European hair and their ability as conditioning compositions was assessed by reference to their ability to ease the combing of hair, both when wet after shampooing, and when dry, for their ability to reduce static, and for the handle (feel and body) they impart to the hair.
  • the tests were carried out as follows. A hair swatch (virgin European brown hair) was wetted and washed twice using a shampoo, based on 20% sodium lauryl ether sulphate and 3.5% of linoleic diethanola ide. The hair swatch was rinsed well in running water. Then 5ml of the composition under examination per 7.8g of hair was applied to the swatch.
  • the hair swatch was then dried in an air-circulating oven at 70°C for one hour.
  • dry comba ⁇ bility was assessed in the same way as the wet combability, results of the initial combing and final combing being recorded in Table 2 in the columns "Dry Comb I" and “Dry Comb F” respectively.
  • the percentage increase in bulk size was measured and recorded in Table 2 as "Body".
  • the static of the hair was assessed by combing the dry hair five times downwards with a plastic comb, and comparing the angle at which the hair spreads out before and after the combing. Performance of the compositions in this test was ranked on a scale 0 to 5 with 0 recording total absence of static.
  • the handle was assessed by feeling the hair and considering its softness, silkiness and body. This test was carried out by a panel of people and the average result is recorded in Table 2.
  • composition Component(a) Componen (b) Ratio

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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Abstract

Composition de lotion améliorée destinée par exemple aux cheveux, réalisée par mélange d'une émulsion aqueuse d'un polydiorganosiloxane qui est de préférence un polydiméthylsiloxane linéaire ou un polyméthylphénylsiloxane, d'un silane d'ammonium quaternaire de formule générale (ii) R33SiR4N+(R5)3X- comportant de préférence un groupe aliphatique C8-18 ainsi que deux groupes aliphatiques C1-5 liés à l'atome N. On peut utiliser la composition comme lotion de rinçage, ou on peut l'incorporer dans une composition de shampooing.
PCT/GB1988/000962 1987-11-11 1988-11-07 Composition de lotion WO1989004163A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB878726439A GB8726439D0 (en) 1987-11-11 1987-11-11 Conditioning compositions
GB8726439 1987-11-11

Publications (1)

Publication Number Publication Date
WO1989004163A1 true WO1989004163A1 (fr) 1989-05-18

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ID=10626794

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1988/000962 WO1989004163A1 (fr) 1987-11-11 1988-11-07 Composition de lotion

Country Status (5)

Country Link
EP (1) EP0340269A1 (fr)
JP (1) JPH02502184A (fr)
CA (1) CA1331145C (fr)
GB (1) GB8726439D0 (fr)
WO (1) WO1989004163A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0590192A1 (fr) * 1991-04-09 1994-04-06 Toshiba Silicone Co., Ltd. Composition cosmétique
EP0617607A1 (fr) * 1992-10-20 1994-10-05 Alberto Culver Co Composition de soins des cheveux contenant une huile de silicone dispersee.
US5676938A (en) * 1992-09-29 1997-10-14 Toshiba Silicone Co., Ltd. Cosmetic composition
FR2783164A1 (fr) * 1998-09-16 2000-03-17 Oreal Composition cosmetique a base de composes organiques du silicium, peu ou pas polymerises, solubles dans l'eau, et partiellement neutralises
WO2001022925A1 (fr) * 1999-09-27 2001-04-05 L'oreal Composition cosmetique a base de composes organiques du silicium partiellement neutralises
DE10233963A1 (de) * 2002-07-25 2004-02-12 Itn-Nanovation Gmbh Verwendung von Silanen in kosmetischen Mitteln und Verfahren zur Haarbehandlung
US6953584B1 (en) 1999-09-27 2005-10-11 L'oreal Cosmetic compositions based on organic silicon compounds comprising at least a non basic solubilising function
US7244420B1 (en) 1999-09-27 2007-07-17 L'oreal Cosmetic composition based on organic silicon compounds comprising at least a function with a cosmetic effect
EP1935398A1 (fr) * 2006-12-20 2008-06-25 L'Oréal Utilisation d'une silicone dans une composition de mise en forme des cheveux comprenant un groupe fonctionnel solubilisant
FR2910276A1 (fr) * 2006-12-20 2008-06-27 Oreal Utilisation d'un polymere cationique dans une composition de mise en forme des cheveux comprenant un alcoxysilane contenant un groupe fonctionnel solubilisant
WO2009033399A1 (fr) * 2007-09-13 2009-03-19 Dow Corning (Shanghai) Co., Ltd. Procédé de préparation d'une émulsion de silicone contenant un polysiloxane élastomère qui possède des groupes ammonium quaternaires
US10085927B2 (en) 2009-01-30 2018-10-02 L'oreal Nondetergent cosmetic compositions comprising at least one alkoxysilane and at least one microbial gum and styling uses

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2930438B1 (fr) * 2008-04-25 2012-09-21 Oreal Composition cosmetique comprenant au moins un compose organique du silicium, au moins un tensioactif cationique et au moins un acide organique, et un procede de traitement cosmetique mettant en oeuvre ladite composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2144329A (en) * 1983-07-30 1985-03-06 Dow Corning Compositions and process for treating hair
EP0179347A2 (fr) * 1984-10-12 1986-04-30 Revlon, Inc. Compositions pour le conditionnement des cheveux
GB2173515A (en) * 1985-04-12 1986-10-15 Beecham Group Plc Dye compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2144329A (en) * 1983-07-30 1985-03-06 Dow Corning Compositions and process for treating hair
EP0179347A2 (fr) * 1984-10-12 1986-04-30 Revlon, Inc. Compositions pour le conditionnement des cheveux
GB2173515A (en) * 1985-04-12 1986-10-15 Beecham Group Plc Dye compositions

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0590192A1 (fr) * 1991-04-09 1994-04-06 Toshiba Silicone Co., Ltd. Composition cosmétique
US5676938A (en) * 1992-09-29 1997-10-14 Toshiba Silicone Co., Ltd. Cosmetic composition
EP0617607A1 (fr) * 1992-10-20 1994-10-05 Alberto Culver Co Composition de soins des cheveux contenant une huile de silicone dispersee.
EP0617607A4 (fr) * 1992-10-20 1995-01-11 Alberto Culver Co Composition de soins des cheveux contenant une huile de silicone dispersee.
FR2783164A1 (fr) * 1998-09-16 2000-03-17 Oreal Composition cosmetique a base de composes organiques du silicium, peu ou pas polymerises, solubles dans l'eau, et partiellement neutralises
US7244420B1 (en) 1999-09-27 2007-07-17 L'oreal Cosmetic composition based on organic silicon compounds comprising at least a function with a cosmetic effect
US6953572B1 (en) 1999-09-27 2005-10-11 L'oreal Cosmetic compositions based on partly neutralized organic silicon compounds
US6953584B1 (en) 1999-09-27 2005-10-11 L'oreal Cosmetic compositions based on organic silicon compounds comprising at least a non basic solubilising function
WO2001022925A1 (fr) * 1999-09-27 2001-04-05 L'oreal Composition cosmetique a base de composes organiques du silicium partiellement neutralises
DE10233963A1 (de) * 2002-07-25 2004-02-12 Itn-Nanovation Gmbh Verwendung von Silanen in kosmetischen Mitteln und Verfahren zur Haarbehandlung
EP1935398A1 (fr) * 2006-12-20 2008-06-25 L'Oréal Utilisation d'une silicone dans une composition de mise en forme des cheveux comprenant un groupe fonctionnel solubilisant
FR2910275A1 (fr) * 2006-12-20 2008-06-27 Oreal Utilisation d'une silicone dans une composition de mise en forme des cheveux comprenant une alcoxysilane contenant un groupe fonctionnel solubilisant
FR2910276A1 (fr) * 2006-12-20 2008-06-27 Oreal Utilisation d'un polymere cationique dans une composition de mise en forme des cheveux comprenant un alcoxysilane contenant un groupe fonctionnel solubilisant
WO2009033399A1 (fr) * 2007-09-13 2009-03-19 Dow Corning (Shanghai) Co., Ltd. Procédé de préparation d'une émulsion de silicone contenant un polysiloxane élastomère qui possède des groupes ammonium quaternaires
US10085927B2 (en) 2009-01-30 2018-10-02 L'oreal Nondetergent cosmetic compositions comprising at least one alkoxysilane and at least one microbial gum and styling uses

Also Published As

Publication number Publication date
GB8726439D0 (en) 1987-12-16
EP0340269A1 (fr) 1989-11-08
JPH02502184A (ja) 1990-07-19
CA1331145C (fr) 1994-08-02

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