GB1218759A - Fluorine-containing alkanolamines - Google Patents
Fluorine-containing alkanolaminesInfo
- Publication number
- GB1218759A GB1218759A GB32968A GB32968A GB1218759A GB 1218759 A GB1218759 A GB 1218759A GB 32968 A GB32968 A GB 32968A GB 32968 A GB32968 A GB 32968A GB 1218759 A GB1218759 A GB 1218759A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen atom
- hydroxyalkylamines
- chr
- fluorine
- jan
- 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
Links
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title abstract 3
- 229910052731 fluorine Inorganic materials 0.000 title abstract 3
- 239000011737 fluorine Substances 0.000 title abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 150000001336 alkenes Chemical class 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- -1 fluoroalkyl bromides Chemical class 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 150000004694 iodide salts Chemical class 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/24—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
-
- 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
-
- 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
- D06M13/402—Amides imides, sulfamic acids
- D06M13/408—Acylated amines containing fluorine atoms; Amides of perfluoro carboxylic 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
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/26—Amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Abstract
1,218,759. Fluorine-containing hydroxyalkylamines; fluorinated alkenes. UGINE KUHLMANN. 2 Jan., 1968 [2 Jan., 1967; 15 Sept., 1967; 7 Nov., 1967], No. 329/68. Heading C2C. Novel fluorine - containing hydroxyalkylamines of the formula wherein a is 2 or 4, n is 4 to 20, each of R 2 and R 4 is a hydrogen atom or a C 1-3 alkyl group, Q is a -(CHR 3 )bradical, b being 1 to 10 and R 3 being a hydrogen atom or a C 1-3 alkyl radical, and R 1 is a hydrogen atom or a C 1-20 alkyl, C 3-10 alkenyl, C 3-12 cycloalkyl, C 5-12 cycloalkenyl, aryl, -(CHR 2 ) b OH or -(CR 2 R 4 ) a - C n F 2n+1 radical or R 1 and Q together represent a -(CHR 3 )pradical, p being 2 to 6, are obtained by condensing at 0‹ to 200‹ C. fluoroalkyl bromides or iodides, C n F 2n+1 -(CR 2 R 4 ) a Y, wherein Y is bromine or iodine, with alkanolamines H-NR 1 -Q-OH. The product may be obtained in the form of its hydroiodide. Hydroxyalkylamines of the formula may be obtained as by-products when R 1 in the starting material is a hydrogen atom. The compounds have surface-active properties and are useful as textile adjuvants. Fluorinated alkenes, C n F 2n+1 CH = CH 2 , are obtained as by-products of the above reactions when R 2 and R 4 are both hydrogen atoms and a is 2.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR89676A FR1532284A (en) | 1967-01-02 | 1967-01-02 | New fluorinated organic compounds |
FR121188A FR93170E (en) | 1967-01-02 | 1967-09-15 | New fluorinated organic compounds. |
FR127254A FR93239E (en) | 1967-01-02 | 1967-11-07 | New fluorinated organic compounds. |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1218759A true GB1218759A (en) | 1971-01-13 |
Family
ID=27243773
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32868A Expired GB1218758A (en) | 1967-01-02 | 1968-01-02 | Fluorine-containing acrylamides and methacrylamides |
GB32968A Expired GB1218759A (en) | 1967-01-02 | 1968-01-02 | Fluorine-containing alkanolamines |
GB32768A Expired GB1218757A (en) | 1967-01-02 | 1968-01-02 | Fluorine-containing acrylates and methacrylates |
GB34568A Expired GB1210842A (en) | 1967-01-02 | 1968-01-02 | Improvements in fluorine containing amines |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32868A Expired GB1218758A (en) | 1967-01-02 | 1968-01-02 | Fluorine-containing acrylamides and methacrylamides |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32768A Expired GB1218757A (en) | 1967-01-02 | 1968-01-02 | Fluorine-containing acrylates and methacrylates |
GB34568A Expired GB1210842A (en) | 1967-01-02 | 1968-01-02 | Improvements in fluorine containing amines |
Country Status (6)
Country | Link |
---|---|
BE (4) | BE708724A (en) |
DE (4) | DE1643561B2 (en) |
ES (4) | ES348858A1 (en) |
FR (1) | FR93239E (en) |
GB (4) | GB1218758A (en) |
NL (4) | NL6800011A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104356008A (en) * | 2014-09-16 | 2015-02-18 | 拉芳家化股份有限公司 | Preparation method and application of fluorine-containing quaternary ammonium surfactant |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH592604A5 (en) * | 1973-11-22 | 1977-10-31 | Ciba Geigy Ag | |
US4534978A (en) * | 1982-12-28 | 1985-08-13 | The Green Cross Corporation | Perfluorocycloamines |
DE3347378A1 (en) * | 1983-12-29 | 1985-07-11 | Hoechst Ag, 6230 Frankfurt | FLUORINATED QUATERNAIRE AMMONIUM COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF AS A FLOW ACCELERATOR |
JPS63198651A (en) * | 1987-02-13 | 1988-08-17 | Daikin Ind Ltd | Triperfluoroalkyl amine and production thereof |
CA2118544A1 (en) * | 1993-12-30 | 1995-07-01 | Henry W. Krautter | Reliability elastomeric keypads and method for making same |
-
1967
- 1967-11-07 FR FR127254A patent/FR93239E/en not_active Expired
- 1967-12-22 DE DE1967U0014529 patent/DE1643561B2/en active Granted
- 1967-12-22 DE DE19671668794 patent/DE1668794B2/en active Pending
- 1967-12-22 DE DE19671668795 patent/DE1668795A1/en active Pending
- 1967-12-22 DE DE19671668796 patent/DE1668796A1/en active Pending
- 1967-12-29 BE BE708724D patent/BE708724A/xx not_active IP Right Cessation
- 1967-12-29 BE BE708725D patent/BE708725A/xx not_active IP Right Cessation
- 1967-12-29 BE BE708723D patent/BE708723A/xx not_active IP Right Cessation
- 1967-12-29 BE BE708722D patent/BE708722A/xx not_active IP Right Cessation
- 1967-12-30 ES ES348858A patent/ES348858A1/en not_active Expired
- 1967-12-30 ES ES348856A patent/ES348856A1/en not_active Expired
- 1967-12-30 ES ES348859A patent/ES348859A1/en not_active Expired
- 1967-12-30 ES ES348857A patent/ES348857A1/en not_active Expired
-
1968
- 1968-01-02 GB GB32868A patent/GB1218758A/en not_active Expired
- 1968-01-02 NL NL6800011A patent/NL6800011A/xx unknown
- 1968-01-02 NL NL6800009A patent/NL6800009A/xx unknown
- 1968-01-02 GB GB32968A patent/GB1218759A/en not_active Expired
- 1968-01-02 NL NL6800010A patent/NL158170B/en not_active IP Right Cessation
- 1968-01-02 GB GB32768A patent/GB1218757A/en not_active Expired
- 1968-01-02 NL NL6800012A patent/NL6800012A/xx unknown
- 1968-01-02 GB GB34568A patent/GB1210842A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104356008A (en) * | 2014-09-16 | 2015-02-18 | 拉芳家化股份有限公司 | Preparation method and application of fluorine-containing quaternary ammonium surfactant |
Also Published As
Publication number | Publication date |
---|---|
DE1668794B2 (en) | 1973-01-18 |
GB1218758A (en) | 1971-01-13 |
GB1210842A (en) | 1970-11-04 |
GB1218757A (en) | 1971-01-13 |
ES348858A1 (en) | 1969-07-16 |
DE1668794A1 (en) | 1971-02-11 |
BE708724A (en) | 1968-07-01 |
ES348859A1 (en) | 1969-07-16 |
FR93239E (en) | 1969-02-28 |
DE1668796A1 (en) | 1971-10-07 |
DE1643561B2 (en) | 1976-11-11 |
NL6800011A (en) | 1968-07-03 |
ES348856A1 (en) | 1969-07-16 |
BE708722A (en) | 1968-07-01 |
NL6800010A (en) | 1968-07-03 |
ES348857A1 (en) | 1969-07-16 |
BE708725A (en) | 1968-07-01 |
NL6800009A (en) | 1968-07-03 |
DE1668795A1 (en) | 1971-08-26 |
BE708723A (en) | 1968-07-01 |
DE1643561A1 (en) | 1972-03-16 |
NL158170B (en) | 1978-10-16 |
NL6800012A (en) | 1968-07-03 |
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