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EP0341071B2 - Compositions détergentes - Google Patents

Compositions détergentes Download PDF

Info

Publication number
EP0341071B2
EP0341071B2 EP89304522A EP89304522A EP0341071B2 EP 0341071 B2 EP0341071 B2 EP 0341071B2 EP 89304522 A EP89304522 A EP 89304522A EP 89304522 A EP89304522 A EP 89304522A EP 0341071 B2 EP0341071 B2 EP 0341071B2
Authority
EP
European Patent Office
Prior art keywords
betaine
alkyl
active
amine oxide
ethanolamide
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.)
Expired - Lifetime
Application number
EP89304522A
Other languages
German (de)
English (en)
Other versions
EP0341071B1 (fr
EP0341071A3 (en
EP0341071A2 (fr
Inventor
Appaya Raghunath Naik
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.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10636497&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0341071(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Unilever PLC, Unilever NV filed Critical Unilever PLC
Publication of EP0341071A2 publication Critical patent/EP0341071A2/fr
Publication of EP0341071A3 publication Critical patent/EP0341071A3/en
Publication of EP0341071B1 publication Critical patent/EP0341071B1/fr
Application granted granted Critical
Publication of EP0341071B2 publication Critical patent/EP0341071B2/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides

Definitions

  • the present invention relates to novel detergent compositions and especially, but not exclusively, to foaming liquid compositions useful for light-duty applications such as manual dishwashing.
  • the compositions may also have use for fabric washing, cleaning carpets and as shampoos.
  • Light-duty liquid detergent compositions such as are suitable for use in washing dishes are well known.
  • Many commercially-available formulations are based on a sulphate - or sulphonate-type anionic detergent, especially alkyl sulphate, alkyl benzene sulphonate and alkane sulphonate, in conjunction with an alkyl polyethoxy sulphate (alkyl ether sulphate).
  • the sulphonate-type detergent generally predominates.
  • Alkyl mono- and poly-glycosides are known and have been disclosed in a number of prior art patents and literature publications.
  • Boettner (US3219656) discusses the utility of alkyl mono-glycosides as foam stabilisers for anionic and nonionic surfactants.
  • Lew (US 3772269) discloses that decyl glucoside containing less than 1.6 glucose units acts as a good foamer.
  • Several Procter and Gamble disclosures eg EP 0 070 074, EP 0 070 075 and EP 0 070 076) discuss the utility of alkylpolyglucosides having greater than 1.5 glucose units in detergent compositions.
  • Henkel (EP 216 301 A) disclose the beneficial use of alkyl glycosides having from 1 to 1.4 glucose units which are incorporated in dishwashing liquids comprising ether sulphate and ethanolamide.
  • the present invention relates to safe, mild liquid detergents with a good foam stability and a good cleansing ability based upon alkyl polyglycosides.
  • the invention aims to provide novel, high-foaming nonionic based liquid detergents comprising an alkyl polyglycoside. It is a further aim to provide a mild, ecologically safe liquid detergent.
  • an aqueous liquid detergent composition comprising:
  • Alkyl polyglycosides though nonionic in nature, differ from conventional ethoxylated nonionics such as alkyl ethoxylates or alkylphenol ethoxylates in having a different type of hydrophilic group and in consequence exhibit different physical, chemical and hence functional properties compared to conventional ethoxylated nonionics.
  • ethoxylates are low melting solids or liquids at room temperature, are completely miscible in non-polar solvents and their aqueous solutions have cloud points.
  • alkyl polyglycosides are high melting solids, sparingly soluble in non-polar solvents and their aqueous solutions do not show cloud points.
  • Alkyl polyglycosides also generally give lower surface tensions and give a more stable foam compared to comparable, conventional nonionics.
  • Alkyl polyglycosides are also prepared by different routes and can be produced entirely based on natural raw materials. Hence the compounds and compositions made therewith can be expected to be biologically safer and more acceptable than conventional nonionics and compositions containing them. Impurities present will also differ from conventional nonionics.
  • Alkyl polyglycosides may be manufactured by the Fischer glycoxidation of a detergent alcohol, eg C 8 -C 18 Alcohol + "glucose” + catalyst ⁇ ROG x + H 2 O (ROH) + (G)
  • ROG x product depends on control of the ratios of the reactants.
  • a product will be a ratio of, eg ROG 1 :ROG 2 :ROG 3 .
  • the alkyl polyglycosides used in the present invention have a hydrophobic group containing 8 to 20 carbon atoms, preferably about 10 to about 16, most preferably from 12 to 14, and a polysaccharide hydrophilic group containing from 1 to 1.4 preferably 1.2 to 1.4 saccharide units on average.
  • the saccharide unit may be, for example, a galactoside, glucoside, fructoside or glycosyl. Mixtures thereof may be used.
  • Preferred alkyl polyglycosides are APG 500 from Horizon (APG is a trademark).
  • APG 500 has an average degree of polymerisation of 1.4.
  • the alkyl polyglycoside is preferably the major active component and may, for example, be present at from 30 to 60 wt% of the total active.
  • the co-active anionic surfactant used according to the present invention is a primary alkyl sulphate surfactant.
  • the sulphates may be conventional anionic synthetic detergents, and are sulphuric acid half esters of alkanols. Suitable sulphates are from the linear, or branched, primary alcohols. Preferred alcohols are:
  • Primary alcohols with substantial branching may be used.
  • the preferred cations which neutralise the anionic surfactant are sodium and ammonium, and the latter sulphates can be an aid to hydrotroping of the liquid compositions of the invention.
  • the third essential feature of the present invention is the presence of an amine oxide or a betaine as a lather booster.
  • the amount of amine oxide is not more than 10% by weight of the active detergent mixture.
  • the amount of betaine is not more than 30% by weight of this mixture.
  • the total amount of amine oxide and betaine, and. if present, ethanolamide is from 12 to 30% by weight of the active detergent mixture.
  • the lather booster is preferably present at from 2 to 6% by weight of the total composition. It is preferred to use betaines alone.
  • Suitable betaines include simple betaines of formula: and amido betaines of formula:
  • R is a C 8 to C 18 straight or branched alkyl group. It may be a lauryl group or a middle cut coconut alkyl group.
  • R 6 and R 7 are each C 1 to C 3 alkyl or C 1 to C 3 hydroxyalkyl. Examples of sulphobetaines have the above formulae with -CH 2 CO - 2 replaced by:
  • a suitable simple betaine is Empigen BB from Albright & Wilson. It has the formula quoted above in which R is C 12 to C 14 alkyl, derived from coconut, and R 6 and R 7 are both methyl. Also preferred is Tego L7 from Goldschmidt, which has a whole coconut alkyl group.
  • Suitable amine oxides have the formula: R R 6 R 7 N ⁇ O wherein R is a straight- or branched-chain C 8 to C 18 alkyl group and R 6 and R 7 are each C 1 to C 3 alkyl, or C 1 to C 3 hydroxyalkyl.
  • a suitable amine oxide is Empigen OB from Albright & Wilson. In it R is middle-cut coconut alkyl and R 6 and R 7 are both methyl.
  • compositions according to the present invention may include other conventional ingredients such as minor amounts of builders, urea, sodium or ammonium chloride, corrosion inhibitors, colourings and perfumes.
  • Conventional foam boosters such as ethanolamides may be included.
  • ethanolamide is optional. If present, the total level of betaine and/or amine oxide and ethanolamide is from 12 to 30 wt% of the total active.
  • a preferred ethanolamide is Empilan LME (Albright & Wilson).
  • compositions according to the present invention are of particular use as light duty liquid detergent compositions for manual dishwashing.
  • compositions for manual dishwashing comprise from about 5 to about 60 wt%, preferably about 10 to about 40 wt% of the mixture of active components hereinbefore described, the balance comprising water and solvents.
  • compositions according to the present invention are mild and environmentally safe. They exhibit good foam characteristics.
  • Foaming performance was assessed by means of a modified Schlachter-Dierkes test based on the principle described in Fette und Seifen 1951, 53 , 207.
  • a 100 ml aqueous solution of each material tested, having a concentration of 0.04% active detergent in 24°H water (French hardness) at 45°C was rapidly oscillated using a vertically oscillating perforated disc within a graduated cylinder.
  • increments (0.2 g) of soil 9.5 parts commercial cooking fat, 0.25 parts oleic acid, 0.25 parts stearic acid and 10 parts wheat starch in 120 parts water
  • the result was recorded as the number of soil increments (NSI score): a score difference of 6 or less is generally regarded as insignificant.
  • NAI score number of soil increments
  • a comparison of wheatgerm acid phosphatase (WGAP) test and flex wash test results indicated that formulations giving less than 50% enzyme inhibition under the test conditions are substantially mild; any mildness differences between products giving ⁇ 40% inhibition do not show any detectable mildness differences in flex wash test, indicating that the enzyme test is very sensitive and that in a real life situation there is a threshold level of protein denaturation below which all actives and products are indistinguishably mild.
  • the results of the WGAP test are expressed as percentage inhibition (ie, 100% minus percentage activity remaining). Water gave no inhibition at all, ie 100% of activity remained.
  • compositions tested The varying amounts of ingredients used in the compositions tested are shown below as a percentage of the total weight of the composition.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Claims (4)

  1. Composition détergente liquide aqueuse comprenant:
    (a) un tensioactif alkyl(en C8-18) polyglycoside ayant un degré moyen de polymérisation de 1 à 1,4,
    (b) un tensioactif alkylsulfate primaire,
    (c) une bétaïne et/ou un oxyde d'amine agent de surface; et éventuellement,
    (d) un éthanolamide,
    dans laquelle :
    la quantité de tensioactif anionique n'est pas supérieure à 1,5 fois (sur une base molaire) le niveau de bétaïne et/ou d'oxyde d'amine, et
    le niveau de bétaïne et/ou d'oxyde d'amine et, le cas échéant, d'éthanolamide, représente de 12 à 30% en poids du total des ingrédients actifs.
  2. Composition selon la revendication 1 dans laquelle on utilise une bétaïne seule comme agent renforçateur de mousse.
  3. Composition selon l'une quelconque des revendications 1 ou 2 dans laquelle un ingrédient actif non ionique est aussi présent.
  4. Composition détergente liquide aqueuse selon la revendication 1 comprenant, par rapport à la quantité totale des ingrédients actifs,
    (a) de 50 à 60% en poids d'un tensioactif d'alkylpolyglycoside ayant un degré moyen de polymérisation de 1 à 1,4,
    (b) de 15 à 20% en poids d'un tensioactif alkylsulfate primaire,
    (c) de 10 à 15% en poids d'une bétaïne agent de surface, et
    (d) de 10 à 15% en poids d'un éthanolamide.
EP89304522A 1988-05-06 1989-05-05 Compositions détergentes Expired - Lifetime EP0341071B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8810820 1988-05-06
GB888810820A GB8810820D0 (en) 1988-05-06 1988-05-06 Detergent compositions

Publications (4)

Publication Number Publication Date
EP0341071A2 EP0341071A2 (fr) 1989-11-08
EP0341071A3 EP0341071A3 (en) 1990-07-11
EP0341071B1 EP0341071B1 (fr) 1994-08-03
EP0341071B2 true EP0341071B2 (fr) 2002-11-13

Family

ID=10636497

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89304522A Expired - Lifetime EP0341071B2 (fr) 1988-05-06 1989-05-05 Compositions détergentes

Country Status (9)

Country Link
EP (1) EP0341071B2 (fr)
JP (1) JP2664474B2 (fr)
AU (1) AU615740B2 (fr)
BR (1) BR8902111A (fr)
CA (1) CA1335876C (fr)
DE (1) DE68917195T3 (fr)
ES (1) ES2056215T5 (fr)
GB (1) GB8810820D0 (fr)
ZA (1) ZA893327B (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0699711B2 (ja) * 1989-07-25 1994-12-07 花王株式会社 液体洗浄剤組成物
DE4003098A1 (de) * 1990-02-02 1991-08-08 Henkel Kgaa Waessriges fluessiges reinigungsmittel
US5118440A (en) * 1990-03-05 1992-06-02 The Procter & Gamble Company Light-duty liquid dishwashing detergent composition containing alkyl polysaccharide and alpha-sulfonated fatty acid alkyl ester surfactants
DE4023334A1 (de) * 1990-07-23 1992-01-30 Henkel Kgaa Fluessiges, giess- und pumpfaehiges tensidkonzentrat
WO1992006161A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Compositions detergentes contenant des tensioactifs anioniques, des amides d'acides gras polyhydroxy et un agent ameliorant le pouvoir moussant a selection critique
DE4039229A1 (de) * 1990-12-08 1992-06-11 Huels Chemische Werke Ag Kosmetische reinigungsfluessigkeit
SE468252B (sv) * 1991-04-09 1992-11-30 Berol Nobel Ab Flytande diskmedelskomposition innehaallande ett anjoniskt ytaktivt medel och en kombination av amfotaera foereningar
TR26609A (tr) * 1991-11-21 1995-03-15 Procter & Gamble ANYONIK SüRFAKTANLARI, POLIHIDROKSI YAGLI ASIT AMIDLERI VE ÖNEM TASIYAN BIR SEKILDE SECILEN KÖPüK ARTTIRICI MADDEYI IHTIVA EDEN DETERJAN BILESIMLER.
GB9201519D0 (en) * 1992-01-24 1992-03-11 Unilever Plc Detergent compositions
DE4234487A1 (de) * 1992-10-14 1994-04-21 Henkel Kgaa Wäßrige Detergensgemische
JPH08505424A (ja) * 1993-01-12 1996-06-11 ヘンケル・コーポレイション 皿洗い洗剤
US5518647A (en) * 1993-12-20 1996-05-21 Colgate-Palmolive Company Foaming liquid emulsion composition
ZA951012B (en) * 1994-02-14 1996-08-08 Colgate Palmolive Co Composition
DE4435387C2 (de) * 1994-10-04 1997-08-14 Henkel Kgaa Pumpfähige wäßrige Tensidkonzentrate
DE4435495C2 (de) * 1994-10-04 1997-08-14 Henkel Kgaa Pumpfähige wäßrige Tensidkonzentrate
GB9509452D0 (en) * 1995-05-10 1995-07-05 Unilever Plc Light duty cleaning composititon
US5932535A (en) * 1995-12-21 1999-08-03 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored, low-viscosity surfactant concentrates
DE19548068C1 (de) 1995-12-21 1997-06-19 Henkel Kgaa Verfahren zur Herstellung hellfarbiger, niedrigviskoser Tensidkonzentrate
DE19714369A1 (de) * 1997-04-08 1998-10-15 Henkel Kgaa Mittel für die Reinigung harter Oberflächen
EP1003605A4 (fr) * 1997-06-12 2001-04-18 Henkel Corp Emploi de polyglycosides d'alkyle ameliorant la stabilisation des mousses des amphoacetates
US6673760B1 (en) * 2000-06-29 2004-01-06 Ecolab Inc. Rinse agent composition and method for rinsing a substrate surface
FR2826017B1 (fr) 2001-06-15 2004-06-11 Cognis France Sa Melanges de tensioactifs
KR100494626B1 (ko) * 2002-04-19 2005-06-13 주식회사 엘지생활건강 헹굼성이 우수한 주방용 세제 조성물
JP2005255708A (ja) * 2004-03-09 2005-09-22 Teepol Diversey Kk 濃縮中性洗浄剤組成物
FR2913351B1 (fr) 2007-03-08 2010-11-26 Rhodia Recherches Et Tech Utilisation d'une betaine a titre d'agent de reduction du drainage de la mousse
DE102007032110A1 (de) * 2007-07-09 2009-01-15 Henkel Ag & Co. Kgaa Wasch- oder Reinigungsmittel mit Tensiden auf Basis nachwachsender Rohstoffe
JP5367243B2 (ja) * 2007-09-13 2013-12-11 ディバーシー株式会社 家庭用業務用兼用濃縮中性洗浄剤組成物
US10329521B2 (en) 2014-05-21 2019-06-25 Colgate-Palmolive Company Aqueous liquid dishwashing composition comprising an ammonium alkyl ether sulfate and alkylamidopropyl betaine
WO2017209708A1 (fr) 2016-05-30 2017-12-07 Hayat Kimya San. A. Ş. Composition non irritante pour le lavage de la vaisselle à la main
JP7414896B2 (ja) * 2021-07-16 2024-01-16 ザ プロクター アンド ギャンブル カンパニー 液体食器手洗い用洗浄組成物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3275201D1 (en) * 1981-07-13 1987-02-26 Procter & Gamble Foaming surfactant compositions
JPS58132100A (ja) * 1981-09-28 1983-08-06 ザ・プロクタ−・エンド・ギヤンブル・カンパニ− 洗剤組成物
US4554098A (en) 1982-02-19 1985-11-19 Colgate-Palmolive Company Mild liquid detergent compositions
CA1209010A (fr) * 1982-04-26 1986-08-05 Keith A. Jones Compositions moussantes tensio-actives
JPS60197614A (ja) * 1984-03-21 1985-10-07 Shionogi & Co Ltd 低刺激性シヤンプ−組成物
US4668422A (en) * 1985-05-31 1987-05-26 A. E. Staley Manufacturing Company Liquid hand-soap or bubble bath composition
DE3534082A1 (de) * 1985-09-25 1987-04-02 Henkel Kgaa Fluessiges reinigungsmittel
JP2585032B2 (ja) * 1987-11-30 1997-02-26 株式会社資生堂 洗浄剤組成物

Also Published As

Publication number Publication date
EP0341071B1 (fr) 1994-08-03
AU3398989A (en) 1989-11-09
ZA893327B (en) 1991-01-30
DE68917195D1 (de) 1994-09-08
JP2664474B2 (ja) 1997-10-15
ES2056215T3 (es) 1994-10-01
GB8810820D0 (en) 1988-06-08
DE68917195T3 (de) 2003-04-03
JPH01318089A (ja) 1989-12-22
AU615740B2 (en) 1991-10-10
BR8902111A (pt) 1990-01-02
EP0341071A3 (en) 1990-07-11
DE68917195T2 (de) 1994-12-01
EP0341071A2 (fr) 1989-11-08
ES2056215T5 (es) 2003-05-01
CA1335876C (fr) 1995-06-13

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