GB1272592A - Vapour phase oxidation of hydroxy compounds - Google Patents
Vapour phase oxidation of hydroxy compoundsInfo
- Publication number
- GB1272592A GB1272592A GB2142268A GB2142268A GB1272592A GB 1272592 A GB1272592 A GB 1272592A GB 2142268 A GB2142268 A GB 2142268A GB 2142268 A GB2142268 A GB 2142268A GB 1272592 A GB1272592 A GB 1272592A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glyoxal
- glycol
- compounds
- present
- formaldehyde
- 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
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/835—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with germanium, tin or lead
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/843—Arsenic, antimony or bismuth
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/39—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a secondary hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/185—Saturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Paper (AREA)
Abstract
1,272,592. Oxidizing hydroxy compounds to carbonyl compounds. LAPORTE CHEMICALS Ltd. 6 Aug., 1969 [6 May, 1968], No. 21422/68. Heading C2C. Carbonyl compounds are prepared by the vapour phase oxidation of corresponding hydroxy compounds by contacting at elevated temperature a gaseous mixture containing oxygen and the hydroxy compound with a catalyst containing as essential constituents one or more of Cu and Ag with P as a promoter. Au, As, Sb and/or Sn may also be present. The catalyst may be a mixture of particulate ingredients or may be an alloy, the surface of which may be oxidized prior to use. It may be supported. The oxygen may be introduced at more than one point along the reaction. A diluent gas may be present. The reaction product after removal of readily condensable products may be recycled. Examples oxidize ethylene glycol to glyoxal with some glycollic aldehyde, glycollic acid and formaldehyde, propylene - 1,2 - glycol to methylglyoxal and acetol, butene-2,3-diol to diacetyl and acetoin, and cyclohexan - 1,2 - diol to cyclohexan - 1,2- dione. Reference is also made to the oxidation of C 1-6 aliphatic alcohols, cyclohexanol and benzyl alcohol. In the oxidation of ethylene glycol to glyoxal, unreacted glycol may be removed by cooling the reaction gases to a temperature below the condensation point of ethylene glycol but above that of glyoxal. The glycol reacts with some of the glyoxal to give 2,3-dihydroxydioxan. After separating the condensed material, which may be recycled, an aqueous solution of glyoxal may be formed from the remaining reaction gases. Formaldehyde may be removed from this solution by purging with a gas at elevated temperature and acidic impurities, mainly glycollic acid, by treatment with a weakly basic anion exchange resin in the free base form. Glyoxal prepared as above may be reacted with urea to give 4, 5-dihydroxy-2-ketoimidazolidine. If formaldehyde is also present the 1- and 1,3 - methylol - 4,5 - dihydroxy - 2 - ketoimidazolidines are formed or if an alkanol is also present the 0-alkylmethylol compounds.
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2142268A GB1272592A (en) | 1968-05-06 | 1968-05-06 | Vapour phase oxidation of hydroxy compounds |
NO184469A NO133034C (en) | 1968-05-06 | 1969-05-05 | |
NL6906866A NL168487C (en) | 1968-05-06 | 1969-05-05 | METHOD FOR OXIDIZING DIOLS IN THE VAPOR PHASE TO THE COMPATIBLE DICARBONYL COMPOUNDS. |
CH684269A CH535193A (en) | 1968-05-06 | 1969-05-05 | Process for the preparation of carbonyl compounds |
BE732584D BE732584A (en) | 1968-05-06 | 1969-05-06 | |
FR6914418A FR2007925A1 (en) | 1968-05-06 | 1969-05-06 | |
DE19691967147 DE1967147C2 (en) | 1968-05-06 | 1969-05-06 | Process for the production of glyoxal by vapor phase oxidation of ethylene glycol |
SE637769A SE363816B (en) | 1968-05-06 | 1969-05-06 | |
BR20855169A BR6908551D0 (en) | 1968-05-06 | 1969-05-06 | A CATALYTIC OXIDATION PROCESS OF HYDROXY COMPOUNDS |
ES366867A ES366867A1 (en) | 1968-05-06 | 1969-05-06 | Vapour phase oxidation of hydroxy compounds |
DE19691923048 DE1923048C3 (en) | 1968-05-06 | 1969-05-06 | Process for the preparation of dicarbonyl compounds by vapor phase oxidation of an aliphatic diol or of cyclohexane-1,2-diol |
JP8137872A JPS4930807B1 (en) | 1968-05-06 | 1972-08-14 | |
US05/451,228 US3948997A (en) | 1968-05-06 | 1974-03-14 | Vapour phase oxidation process |
NLAANVRAGE8104458,A NL175291C (en) | 1968-05-06 | 1981-09-29 | METHOD FOR OXIDIZING DIOLS IN THE VAPOR PHASE TO THE COMPATIBLE DICARBONYL COMPOUNDS. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2142268A GB1272592A (en) | 1968-05-06 | 1968-05-06 | Vapour phase oxidation of hydroxy compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1272592A true GB1272592A (en) | 1972-05-03 |
Family
ID=10162679
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2142268A Expired GB1272592A (en) | 1968-05-06 | 1968-05-06 | Vapour phase oxidation of hydroxy compounds |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS4930807B1 (en) |
BE (1) | BE732584A (en) |
BR (1) | BR6908551D0 (en) |
CH (1) | CH535193A (en) |
DE (2) | DE1923048C3 (en) |
ES (1) | ES366867A1 (en) |
FR (1) | FR2007925A1 (en) |
GB (1) | GB1272592A (en) |
NL (1) | NL168487C (en) |
NO (1) | NO133034C (en) |
SE (1) | SE363816B (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2634439A1 (en) * | 1975-07-31 | 1977-02-10 | American Cyanamid Co | METHOD FOR MANUFACTURING GLYOXAL |
EP0007570A1 (en) * | 1978-07-24 | 1980-02-06 | BASF Aktiengesellschaft | Process for the preparation of glyoxal from ethylene glycol |
US4258216A (en) * | 1975-07-31 | 1981-03-24 | American Cyanamid Company | Vapor phase oxidation process for glyoxal |
JPS5838227A (en) * | 1981-09-01 | 1983-03-05 | Mitsui Toatsu Chem Inc | Preparation of aldehyde |
EP0091060A2 (en) * | 1982-04-08 | 1983-10-12 | BASF Aktiengesellschaft | Process for producing formaldehyde |
US4439625A (en) * | 1982-09-29 | 1984-03-27 | E. I. Du Pont De Nemours And Company | Production of formaldehyde |
US4503261A (en) * | 1982-07-22 | 1985-03-05 | Basf Aktiengesellschaft | Preparation of glyoxal |
US4511739A (en) * | 1979-06-02 | 1985-04-16 | Basf Aktiengesellschaft | Continuous preparation of glyoxal |
US4555583A (en) * | 1982-08-30 | 1985-11-26 | Mitsui Toatsu Chemicals, Incorporated | Preparation process for glyoxal |
US4599459A (en) * | 1984-08-31 | 1986-07-08 | Masanao Hirose | Method for the ultrasonic treatment of a dilute alcoholic solution |
US4851584A (en) * | 1987-04-15 | 1989-07-25 | Basf Aktiengesellschaft | Preparation of carbonyl compounds |
WO2007132011A1 (en) * | 2006-05-17 | 2007-11-22 | Basf Aktiengesellschaft | Method for producing vicinal dioxo compounds by oxidation of vicinal dihydroxy compounds on a structured catalyst packing |
DE102008002535A1 (en) | 2007-06-25 | 2009-01-02 | Basf Se | Producing vicinal dioxo compounds, preferably glyoxal, useful as cross linker functionalized polymers, comprises gas phase oxidation of vicinal dihydroxy compounds in presence of gases containing oxygen on a catalyst comprising e.g. gold |
US8461396B2 (en) | 2010-10-01 | 2013-06-11 | Basf Se | Process for purifying aqueous glyoxal solutions |
WO2022058188A1 (en) | 2020-09-17 | 2022-03-24 | Basf Se | Process for the production of glyoxal |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5490109A (en) * | 1977-12-24 | 1979-07-17 | Basf Ag | Manufacture of fatty hydroxycarbonyl compound etherified with fatty group |
DE2803318A1 (en) * | 1978-01-26 | 1979-08-09 | Basf Ag | METHOD FOR MANUFACTURING GLYOXAL |
DE3012004A1 (en) * | 1980-03-28 | 1981-10-15 | Hoechst Ag, 6000 Frankfurt | METHOD FOR PRODUCING METHYLGLYOXAL |
DE3643469A1 (en) * | 1986-12-19 | 1988-06-30 | Basf Ag | METHOD FOR PRODUCING CARBONYL COMPOUNDS |
CN101472873A (en) * | 2006-05-17 | 2009-07-01 | 巴斯夫欧洲公司 | Temperature adjustment in oxidation reactions of hydrocarbons |
DE102008018480B4 (en) | 2007-04-13 | 2020-10-15 | Basf Se | Process for the preparation of vicinal dioxo compounds by oxidation of vicinal dihydroxy compounds |
CN102272084A (en) | 2008-12-29 | 2011-12-07 | 巴斯夫欧洲公司 | Method for cleaning aqueous glyoxal solutions |
EP2621878B1 (en) | 2010-10-01 | 2016-06-01 | Basf Se | Process for purifying aqueous glyoxal solutions |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1497817A (en) * | 1918-08-13 | 1924-06-17 | Seth B Hunt | Process of making acetone and other ketones |
US2051266A (en) * | 1935-03-23 | 1936-08-18 | Shell Dev | Catalytic oxidation of polyhydric alcohols |
US2462107A (en) * | 1943-05-03 | 1949-02-22 | Ninol Dev Co | Process for preparation of diacetyl |
FR1060331A (en) * | 1951-08-02 | 1954-04-01 | Basf Ag | Process for obtaining ureins from ethanedial |
US3049446A (en) * | 1960-02-05 | 1962-08-14 | Sun Chemical Corp | Process for the manufacture of urea, glyoxal and formaldehye reaction product useful for improving cellulosic textile materials |
-
1968
- 1968-05-06 GB GB2142268A patent/GB1272592A/en not_active Expired
-
1969
- 1969-05-05 NO NO184469A patent/NO133034C/no unknown
- 1969-05-05 NL NL6906866A patent/NL168487C/en not_active IP Right Cessation
- 1969-05-05 CH CH684269A patent/CH535193A/en not_active IP Right Cessation
- 1969-05-06 SE SE637769A patent/SE363816B/xx unknown
- 1969-05-06 BE BE732584D patent/BE732584A/xx not_active IP Right Cessation
- 1969-05-06 FR FR6914418A patent/FR2007925A1/fr active Pending
- 1969-05-06 DE DE19691923048 patent/DE1923048C3/en not_active Expired
- 1969-05-06 BR BR20855169A patent/BR6908551D0/en unknown
- 1969-05-06 DE DE19691967147 patent/DE1967147C2/en not_active Expired
- 1969-05-06 ES ES366867A patent/ES366867A1/en not_active Expired
-
1972
- 1972-08-14 JP JP8137872A patent/JPS4930807B1/ja active Pending
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2634439A1 (en) * | 1975-07-31 | 1977-02-10 | American Cyanamid Co | METHOD FOR MANUFACTURING GLYOXAL |
US4258216A (en) * | 1975-07-31 | 1981-03-24 | American Cyanamid Company | Vapor phase oxidation process for glyoxal |
EP0007570A1 (en) * | 1978-07-24 | 1980-02-06 | BASF Aktiengesellschaft | Process for the preparation of glyoxal from ethylene glycol |
US4282374A (en) * | 1978-07-24 | 1981-08-04 | Basf Aktiengesellschaft | Preparation of glyoxal from ethylene glycol |
US4511739A (en) * | 1979-06-02 | 1985-04-16 | Basf Aktiengesellschaft | Continuous preparation of glyoxal |
JPS5838227A (en) * | 1981-09-01 | 1983-03-05 | Mitsui Toatsu Chem Inc | Preparation of aldehyde |
EP0091060A2 (en) * | 1982-04-08 | 1983-10-12 | BASF Aktiengesellschaft | Process for producing formaldehyde |
EP0091060A3 (en) * | 1982-04-08 | 1986-07-23 | Basf Aktiengesellschaft | Process for producing formaldehyde |
US4503261A (en) * | 1982-07-22 | 1985-03-05 | Basf Aktiengesellschaft | Preparation of glyoxal |
US4555583A (en) * | 1982-08-30 | 1985-11-26 | Mitsui Toatsu Chemicals, Incorporated | Preparation process for glyoxal |
EP0104666A2 (en) * | 1982-09-29 | 1984-04-04 | E.I. Du Pont De Nemours And Company | Production of formaldehyde |
EP0104666A3 (en) * | 1982-09-29 | 1985-10-23 | E.I. Du Pont De Nemours And Company | Production of formaldehyde |
US4439625A (en) * | 1982-09-29 | 1984-03-27 | E. I. Du Pont De Nemours And Company | Production of formaldehyde |
US4599459A (en) * | 1984-08-31 | 1986-07-08 | Masanao Hirose | Method for the ultrasonic treatment of a dilute alcoholic solution |
US4851584A (en) * | 1987-04-15 | 1989-07-25 | Basf Aktiengesellschaft | Preparation of carbonyl compounds |
WO2007132011A1 (en) * | 2006-05-17 | 2007-11-22 | Basf Aktiengesellschaft | Method for producing vicinal dioxo compounds by oxidation of vicinal dihydroxy compounds on a structured catalyst packing |
DE102008002535A1 (en) | 2007-06-25 | 2009-01-02 | Basf Se | Producing vicinal dioxo compounds, preferably glyoxal, useful as cross linker functionalized polymers, comprises gas phase oxidation of vicinal dihydroxy compounds in presence of gases containing oxygen on a catalyst comprising e.g. gold |
US8461396B2 (en) | 2010-10-01 | 2013-06-11 | Basf Se | Process for purifying aqueous glyoxal solutions |
WO2022058188A1 (en) | 2020-09-17 | 2022-03-24 | Basf Se | Process for the production of glyoxal |
Also Published As
Publication number | Publication date |
---|---|
JPS4930807B1 (en) | 1974-08-16 |
DE1923048C3 (en) | 1980-06-19 |
CH535193A (en) | 1973-03-31 |
DE1923048A1 (en) | 1969-11-20 |
NO133034C (en) | 1976-02-25 |
DE1923048B2 (en) | 1979-07-19 |
DE1967147B1 (en) | 1979-06-13 |
NL168487C (en) | 1982-04-16 |
DE1967147C2 (en) | 1980-02-14 |
NL6906866A (en) | 1969-11-10 |
BE732584A (en) | 1969-11-06 |
BR6908551D0 (en) | 1973-01-04 |
ES366867A1 (en) | 1971-06-16 |
NO133034B (en) | 1975-11-17 |
SE363816B (en) | 1974-02-04 |
FR2007925A1 (en) | 1970-01-16 |
NL168487B (en) | 1981-11-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PE20 | Patent expired after termination of 20 years |