CA1153510A - Fabric softeners - Google Patents

Fabric softeners

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Publication number
CA1153510A
CA1153510A CA000356977A CA356977A CA1153510A CA 1153510 A CA1153510 A CA 1153510A CA 000356977 A CA000356977 A CA 000356977A CA 356977 A CA356977 A CA 356977A CA 1153510 A CA1153510 A CA 1153510A
Authority
CA
Canada
Prior art keywords
alkyl
methyl
weight
iii
carbon atoms
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
Application number
CA000356977A
Other languages
French (fr)
Inventor
Adolf May
Hans-Walter Bucking
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.)
Hoechst AG
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Application granted granted Critical
Publication of CA1153510A publication Critical patent/CA1153510A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic
    • 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
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • D06M13/473—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having five-membered heterocyclic rings
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • D06M2101/08—Esters or ethers of cellulose
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/10—Animal fibres
    • D06M2101/12—Keratin fibres or silk
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/18—Synthetic fibres consisting of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/18—Synthetic fibres consisting of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/26—Polymers or copolymers of unsaturated carboxylic acids or derivatives thereof
    • D06M2101/28—Acrylonitrile; Methacrylonitrile
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/32—Polyesters
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/34—Polyamides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

FABRIC SOFTENER
Abstract of the disclosure:
Fabric softeners in the form of an aqueous solution or dispersion, which contain from 1 to 15 % by weight of one or several compounds of formulae I to III

I

II
III

in which R1 is alkyl or alkenyl each with 10 to 30 carbon atoms, R2 is alkyl of from 1 to 4 carbon atoms, R3 is methyl or hydrogen, m is a number of from 1 to 15, and A is an anion,and from 0.01 to 4 % by weight of a fatty acid ethanolamide polyglycol ether of formula IV

IV

in which R4 is C4-C20-alkyl, n is a number of from 2 to 20, x and y represent hydrogen or methyl, but are not methyl at the same time, and further common auxiliaries and additives.

Description

~JV~A.
- 2 - ~IOE 79/F 203 It is known tha-t textiles W}li ch have been washed, especially in an au-tomatic washer, and partlcularly those made from cellulcse ibers, are in an unpleasant hardene-1 state aEter drying. This undes:irably hardened feel can be overcome by treating the te~tiles af-ter washing in a rinsing bath with cationic substances which contain at least two long-chain aliphatic radicals in the molecule.
Especially the dialkyl-dimethylammonium salts dispersible in water have proved in practice to be suitable for this application. However, on overdosage, these products have the disadvantage of ma~ing the treated fabric hydro-phobic, thus retaxding rewetting.
It has now been found~that these disadvantages are overcome by combining the quaternary ammonium compounds used as fabric softeners with a fatty acid ethanolamide po]yglycol ether. ~ubjec-t of the invention are therefore fabric softeners in -the form of an aqueous solution or dispersion which contain from 1 to 15, preferably 2 to 6, % by weiyht of one or more compounds of formu]ae I to III

' \ a / 2 l A~ X

-R~ C N-~ 2 l A II
~----^-C~I~
~ .
R2 CH2 Cll2 NH C R~

R1 \ / R2 l III

R1 \ (CII~C'.I~ H ~ A

~153S~O

in which Rl is alkyl or alkenyl each with 10 to 30 carbon atoms, preferably from 8 to 14 carbon atoms, R2 is alkyl of from 1 to 4 carbon atoms, preferably methyl, R3 is methyl or hydrogen, m is a number of from 1 to 15, preferably 1, and A is an anion, such as Cl( ), Br( ), R20S03( ) or R20P03( ), and from 0.01 to less than 3, preferably from 0.5 to 2.5, % by weight of a fatty acid ethanolamide polyglycol ether of formula IV
R4-C0-NH-(CH-ICHO)nH IV, x y in which R4 is C4-C20-alkyl, preferably C8-Cl6-alkyl, n is a number of from 2 to 20, preferably from 2 to 6, x and y represent hydrogen or methyl, but are not methyl at the same time.
This combination of compounds I, II or III with a compound of formula IV imparts a pleasant and soft feel to any textile material, especially those made from natural or regenerated cellulose, wool, cellulose acetate, cellulose triacetate, polyamide, polyacrylonitrile, polyesters, or polypropylene.
Especially advantageous is its use for the after-treatment of terry fabrics and underwear made of cotton. The fabric softeners of the invention are prepared by simply mixing or dispersing the individual components in water. They may contain one compound each of formulae I to III, or a mixture of two or more compounds of these formulae within the ranges as indicated. In the case of a mixture of two or more compounds of formulae I to III, the mixing ratio thereof with one another is not at all critical and may have any value.
The fabric softeners of the invention may also contain further substances and auxiliaries which are either mixed already with the concentrate of the fabric softener or are added separately to the ready-to-use dilute composition. These are substances or auxiliaries which are conventionally used in softening compositions;

they include, for example, cationic and nonionic sur-face-actlve substances, electrolytesl neutralizing agents, organic complexing agents, optical brighteners and solubilizers, as well as dyestuffs and perfumes.
Additives of this kind serve, for example, to further influence the feel of the fabric or other properties of the tex~ile goods to be treated, or the adjustment of the viscosity or pH or further promote the stability of the solutions at low temperatures.
The fabric softeners are applied as usual, that is, they are added to the last rinsing water after the washing operations are complete. The textiles so treated are subsequently dried, the rewettability of the textile material thus being markedly improved as compared with commercial agents.
In the following Examples, some fabric softeners of the invention have been described. The percentages are in all cases per cent by weight. These fabric softeners are in all cases prepared by simply mixing aqueous solutions of the individual components with ayitation in the cold.
E X A M P L E
Distearyldimethylammonium chloride~ %
Coconut fatty acid ethanolamide +2 %
25 S ethylene oxide units Dyestuff, perfume, water remainder ad 100 %

Di-tallow fatty alkyl-dimethylammonium chloride S.3 %
Coconut fatty acid ethanolamide + 5 EO 2 30 Dyestuff, perfume, water remainderad 100 %

DialkyJ imida~oline derivative of formula IL~
R C -C -alkenyl, R2=CH3, A 3 3 Coconut- fatty acid ethanolamide + 5 EO 2 %
35 Dyestuff~ pexfume and water remainder ad 100 %

~53S~O

Comparative formulation Distearyldimethylammonium chloride6 %
Non-ionic surfactant nonylpheno] oxethylate 1 %
+ 10 ethylene oxide units Dyestuff, perfume and water remainder ad 100 %.
These fabric softeners were tested for their influence on the rewettabilit~ according to the method of capillary rise (German Industrial Standard DIN 53 924).
Smooth cotton fabrics are treated with the mi.xtures of the invention. A commercial softener (Example 4) was used for comparison. According to this test method, the results listed in the following Table were obtained for the mixtures of Examples 1 to 4. The rise of unfinished fabrics is defined as being 100 %.

Rise in %
1 g of FS/kg of fabric ___ _ 20 Example 1 73 %
Example 2 70 %
Example 3 71 %
Example 4 (Comparative formulati.on) 50 %

The results show that the fabric softener comh.inati.ons of the invention havc an improved absorption capaci.ty as compared against a commercial product.

Claims (3)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A fabric softener in the form of an aqueous solution or dispersion, which contains from 1 to 15 % by weight of one or more compounds of formulae I to III

I

II

III, in which Rl is alkyl or alkenyl of from 10 to 30 carbon atoms, R2 is alkyl of from 1 to 4 carbon atoms, R3 is methyl or hydrogen, m is a number of from 1 to 15, and A is an anion, and from 0.01 to less than 3 % by weight of a fatty acid ethanolamide polyglycol ether of formula IV
IV, in which R4 is C4-C20-alkyl, n is a number of from 2 to 20 x and y represent hydrogen or methyl, but are not methyl at the same time.
2. A fabric softener as claimed in claim 1 which contains from 1 to 15 % by weight of one or more compounds of formulae I to III in which Rl is alkyl or alkenyl each with 8 to 14 carbon atoms, R2 is methyl, R3 is methyl or hydrogen, m is 1 and A is Cl.THETA., Br.THETA., R2OSO3.THETA. or R2OPO3e and from 0.5 to 2.5 % by weight of a fatty acid ethanolamide polyglycol ether of formula IV in which R4 is C8-C16-alkyl, n is a number of from 2 to 6 and x and y are as defined in claim 1.
3. A fabric softener as claimed in claim 1, which contains from 2 to 6 % by weight of one or more compounds of formulae I, II or III and from O.S to 2.5 % by weight of a fatty acid ethanolamide polyglycol ether of formula IV.
CA000356977A 1979-07-25 1980-07-24 Fabric softeners Expired CA1153510A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19792930061 DE2930061A1 (en) 1979-07-25 1979-07-25 SOFT SOFTENER
DEP2930061.6 1979-07-25

Publications (1)

Publication Number Publication Date
CA1153510A true CA1153510A (en) 1983-09-13

Family

ID=6076677

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000356977A Expired CA1153510A (en) 1979-07-25 1980-07-24 Fabric softeners

Country Status (6)

Country Link
EP (1) EP0023334B1 (en)
JP (1) JPS5620677A (en)
AT (1) ATE5662T1 (en)
BR (1) BR8004626A (en)
CA (1) CA1153510A (en)
DE (2) DE2930061A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6635607B2 (en) 2001-05-15 2003-10-21 Ici Americas Inc. Mixed polyalkylene glycol hydroxyalkyl isostearamides as rheology adjuvants

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4439335A (en) * 1981-11-17 1984-03-27 The Procter & Gamble Company Concentrated fabric softening compositions
DE3150179A1 (en) * 1981-12-18 1983-06-23 Hoechst Ag, 6230 Frankfurt CONCENTRATED PRE-MIXTURES OF SOFT SOFTENER
DE3150178A1 (en) * 1981-12-18 1983-06-30 Hoechst Ag, 6230 Frankfurt "CONCENTRATED SOFT SOFT DETERGENT"
JPS58144175A (en) * 1982-02-23 1983-08-27 ライオン株式会社 Article for treating fiber product
US4497716A (en) * 1982-12-23 1985-02-05 Lever Brothers Company Fabric softening composition
GB8410319D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous fabric softening composition
GB8410321D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous concentrated fabric softening composition
GB8410320D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous fabric softening composition
GB8430301D0 (en) * 1984-11-30 1985-01-09 Swan Thomas & Co Ltd Compositions of matter for fabric softeners
DE69533466T2 (en) * 1994-10-14 2005-09-22 Kao Corp. Liquid fabric softener composition
GB2319180B (en) * 1996-11-12 2001-01-17 Reckitt & Colman Inc Mycobacterial compositions
DE19651447C1 (en) * 1996-12-11 1997-10-02 Henkel Kgaa Textile or hair conditioners having improved performance
DE19708133C1 (en) * 1997-02-28 1997-12-11 Henkel Kgaa Conditioner for textile and keratin fibres useful as e.g. laundry or hair conditioner
JP7415563B2 (en) 2020-01-07 2024-01-17 富士フイルムビジネスイノベーション株式会社 Information processing device and program

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE545267A (en) *
US3451927A (en) * 1964-07-08 1969-06-24 Lever Brothers Ltd Fabric conditioner
DE2605502A1 (en) * 1976-02-12 1977-08-18 Exquisit Kosmetik Gmbh Washing and rinsing composition for softening textiles - nonionic surfactant, softening agent and polyglycol difatty acid ester

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6635607B2 (en) 2001-05-15 2003-10-21 Ici Americas Inc. Mixed polyalkylene glycol hydroxyalkyl isostearamides as rheology adjuvants

Also Published As

Publication number Publication date
EP0023334A1 (en) 1981-02-04
JPS6338470B2 (en) 1988-07-29
JPS5620677A (en) 1981-02-26
BR8004626A (en) 1981-02-03
EP0023334B1 (en) 1983-12-21
DE3065943D1 (en) 1984-01-26
ATE5662T1 (en) 1984-01-15
DE2930061A1 (en) 1981-02-19

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