DE1966959A1 - 2-hydroxypropyl-perfluoralkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung zum ausruesten von textilgut - Google Patents

2-hydroxypropyl-perfluoralkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung zum ausruesten von textilgut

Info

Publication number
DE1966959A1
DE1966959A1 DE19691966959 DE1966959A DE1966959A1 DE 1966959 A1 DE1966959 A1 DE 1966959A1 DE 19691966959 DE19691966959 DE 19691966959 DE 1966959 A DE1966959 A DE 1966959A DE 1966959 A1 DE1966959 A1 DE 1966959A1
Authority
DE
Germany
Prior art keywords
general formula
water
perfluoroalkyl
radical
compound
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.)
Pending
Application number
DE19691966959
Other languages
German (de)
English (en)
Inventor
Masayuki Asaoka
Shoshin Fujui
Iwao Hisamaoto
Masayuki Iwatani
Atsuo Katsushima
Chiki Maeda
Hiroyuki Shinkai
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.)
Daikin Industries Ltd
Original Assignee
Daikin Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP9351368A external-priority patent/JPS5011347B1/ja
Priority claimed from JP9351468A external-priority patent/JPS4724000B1/ja
Priority claimed from JP1841169A external-priority patent/JPS5020200B1/ja
Application filed by Daikin Industries Ltd filed Critical Daikin Industries Ltd
Publication of DE1966959A1 publication Critical patent/DE1966959A1/de
Pending 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
    • C08G18/3804—Polyhydroxy compounds
    • C08G18/3812—Polyhydroxy compounds having fluorine atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
    • C08G18/4607—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen having halogens
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/68—Unsaturated polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
    • C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
    • 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
    • D06M13/10—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 oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/10—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 oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
    • D06M13/21—Halogenated carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/213—Perfluoroalkyl carboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/10—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 oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D06M13/236—Esters of carboxylic acids; Esters of carbonic acid containing halogen atoms
    • 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
    • D06M13/325—Amines
    • D06M13/328—Amines the amino group being bound to an acyclic or cycloaliphatic carbon atom
    • D06M13/33—Amines the amino group being bound to an acyclic or cycloaliphatic carbon atom containing halogen atoms
    • 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
    • D06M13/368—Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases
    • 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
    • D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Detergent Compositions (AREA)
DE19691966959 1968-11-18 1969-11-18 2-hydroxypropyl-perfluoralkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung zum ausruesten von textilgut Pending DE1966959A1 (de)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP8427668 1968-11-18
JP8925268 1968-12-05
JP9351368A JPS5011347B1 (enExample) 1968-12-19 1968-12-19
JP9351468A JPS4724000B1 (enExample) 1968-12-19 1968-12-19
JP952469 1969-02-07
JP1841169A JPS5020200B1 (enExample) 1969-03-10 1969-03-10
JP7414669 1969-09-18

Publications (1)

Publication Number Publication Date
DE1966959A1 true DE1966959A1 (de) 1976-01-02

Family

ID=27563512

Family Applications (2)

Application Number Title Priority Date Filing Date
DE19691966959 Pending DE1966959A1 (de) 1968-11-18 1969-11-18 2-hydroxypropyl-perfluoralkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung zum ausruesten von textilgut
DE1958012A Expired DE1958012C3 (de) 1968-11-18 1969-11-18 2-Hydroxypropylperfluoralkyldicarbonsäureester und ihre Verwendung

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE1958012A Expired DE1958012C3 (de) 1968-11-18 1969-11-18 2-Hydroxypropylperfluoralkyldicarbonsäureester und ihre Verwendung

Country Status (6)

Country Link
US (2) US3870748A (enExample)
BE (1) BE741860A (enExample)
CH (4) CH520812A (enExample)
DE (2) DE1966959A1 (enExample)
FR (1) FR2023562A1 (enExample)
GB (1) GB1301480A (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4165338A (en) * 1968-11-18 1979-08-21 Daikin Kogyo Co., Ltd. 2-Hydroxy-1,1,2,3,3-pentahydro-perfluoroalkyl derivatives, their production and use

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1966959A1 (de) * 1968-11-18 1976-01-02 Daikin Ind Ltd 2-hydroxypropyl-perfluoralkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung zum ausruesten von textilgut
CH576936A5 (enExample) * 1972-11-28 1976-06-30 Ciba Geigy Ag
US4209610A (en) * 1975-06-30 1980-06-24 Frank Mares Partially fluorinated esters or amide/esters of benzene polycarboxylic acids, and dyeable pet and nylon fibers incorporating the same and process of making such fibers
US4029585A (en) * 1975-07-26 1977-06-14 E. I. Du Pont De Nemours And Company Aqueous dispersions of perfluoroalkyl esters for treating textiles
US4046944A (en) * 1976-04-06 1977-09-06 Ciba-Geigy Corporation Fluorinated condensation polymers and their use as soil release agents
US4219625A (en) * 1977-12-16 1980-08-26 Allied Chemical Corporation Fluorinated polyol esters
US4473371A (en) * 1981-09-04 1984-09-25 Hoechst Aktiengesellschaft Perfluoroalkyl esters, a process for their preparation and their use as a soil-repellant agent
US4426476A (en) 1982-02-03 1984-01-17 Minnesota Mining And Manufacturing Company Textile treatments
US4472466A (en) * 1982-03-08 1984-09-18 American Hoechst Corporation Soil repellent fluorinated esters of multi-ring anhydride systems
US4395566A (en) * 1982-03-08 1983-07-26 American Hoechst Corporation Solvent-free esterification of carboxyaromatics
US4550189A (en) * 1982-08-23 1985-10-29 American Hoechst Corporation Soil repellents derived from fluorinated acrylates and aromatic amines
US4537728A (en) * 1982-09-30 1985-08-27 Allied Corporation Fluorinated and non-fluorinated terminally halogenated alkyl pyromellitates
DE3622534A1 (de) * 1986-07-04 1988-01-07 Hoechst Ag Neue polyfluorierte cyclische carbonate, verfahren zu ihrer herstellung und ihrer verwendung
US5032666A (en) * 1989-06-19 1991-07-16 Becton, Dickinson And Company Amine rich fluorinated polyurethaneureas and their use in a method to immobilize an antithrombogenic agent on a device surface
US5068397A (en) * 1990-08-15 1991-11-26 Ciba-Geigy Corporation Tris-perfluoroalkyl terminated neopentyl alcohols and derivatives therefrom
US5266724A (en) * 1990-09-04 1993-11-30 Matsushita Electric Industrial Co., Ltd. Fluorine-containing compounds
US5188747A (en) * 1990-09-04 1993-02-23 Matsushita Electric Industrial Co., Ltd. Fluorine-containing lubricant compounds
US5690949A (en) * 1991-10-18 1997-11-25 Minnesota Mining And Manufacturing Company Microporous membrane material for preventing transmission of viral pathogens
MX9205964A (es) * 1991-10-18 1993-12-01 Minnesota Mining & Mfg Material de membrana microporosa y metodo para prevenir la transmision de patogenos virales utilizando dicho material.
US5981038A (en) * 1991-10-18 1999-11-09 3M Innovative Properties Company Minnesota Mining And Manufacturing Co. Laminate preventing transmissions of viral pathogens
JP2884900B2 (ja) * 1992-04-08 1999-04-19 日本電気株式会社 磁気記憶体
US5380778A (en) * 1992-09-30 1995-01-10 Minnesota Mining And Manufacturing Company Fluorochemical aminoalcohols
US6610917B2 (en) 1998-05-15 2003-08-26 Lester F. Ludwig Activity indication, external source, and processing loop provisions for driven vibrating-element environments
FR2785531B1 (fr) * 1998-11-09 2000-12-15 Oreal Composition de vernis a ongles comprenant un citrate fluore

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057890A (en) * 1958-04-17 1962-10-09 Petrolite Corp Certain polyoxyalkylene glycol esters
US3385904A (en) * 1962-10-30 1968-05-28 Minnesota Mining & Mfg Decyclization of fluorinated cyclic ethers to perfluorinated tertiary alcohols
US3459788A (en) * 1964-02-25 1969-08-05 Nippon Soda Co Process for preparation of bis-(beta-hydroxyethyl)-benzene dicarboxylate
FR1408874A (fr) * 1964-07-08 1965-08-20 Rhone Poulenc Sa Procédé de préparation de téréphtalate d'hydroxyéthyle
US3433824A (en) * 1965-07-19 1969-03-18 Dow Chemical Co Process for making glycol esters
JPS5242784B1 (enExample) * 1968-05-30 1977-10-26
DE1966959A1 (de) * 1968-11-18 1976-01-02 Daikin Ind Ltd 2-hydroxypropyl-perfluoralkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung zum ausruesten von textilgut
US3624139A (en) * 1969-01-02 1971-11-30 Basf Wyandotte Corp Acrylic acid esters
US3504016A (en) * 1969-02-28 1970-03-31 Du Pont Fluorinated polyesters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4165338A (en) * 1968-11-18 1979-08-21 Daikin Kogyo Co., Ltd. 2-Hydroxy-1,1,2,3,3-pentahydro-perfluoroalkyl derivatives, their production and use

Also Published As

Publication number Publication date
FR2023562A1 (enExample) 1970-08-21
DE1958012A1 (de) 1970-06-04
BE741860A (enExample) 1970-05-04
US3870748A (en) 1975-03-11
CH285170A4 (enExample) 1971-09-30
CH527163A (de) 1972-08-31
CH520812A (de) 1972-03-31
DE1958012B2 (de) 1980-04-30
CH528471A (de) 1972-09-30
US4084059A (en) 1978-04-11
DE1958012C3 (de) 1981-02-26
GB1301480A (enExample) 1972-12-29

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