ES366867A1 - Vapour phase oxidation of hydroxy compounds - Google Patents
Vapour phase oxidation of hydroxy compoundsInfo
- Publication number
- ES366867A1 ES366867A1 ES366867A ES366867A ES366867A1 ES 366867 A1 ES366867 A1 ES 366867A1 ES 366867 A ES366867 A ES 366867A ES 366867 A ES366867 A ES 366867A ES 366867 A1 ES366867 A1 ES 366867A1
- Authority
- ES
- Spain
- Prior art keywords
- glyoxal
- glycol
- present
- formaldehyde
- oxidation
- 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
- 230000003647 oxidation Effects 0.000 title abstract 4
- 238000007254 oxidation reaction Methods 0.000 title abstract 4
- 150000002440 hydroxy compounds Chemical class 0.000 title abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 14
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 229940015043 glyoxal Drugs 0.000 abstract 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 4
- 239000007789 gas Substances 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 abstract 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- YLVACWCCJCZITJ-UHFFFAOYSA-N 1,4-dioxane-2,3-diol Chemical compound OC1OCCOC1O YLVACWCCJCZITJ-UHFFFAOYSA-N 0.000 abstract 1
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 abstract 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- -1 aliphatic alcohols Chemical class 0.000 abstract 1
- 239000000956 alloy Substances 0.000 abstract 1
- 229910045601 alloy Inorganic materials 0.000 abstract 1
- 239000003957 anion exchange resin Substances 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910052785 arsenic Inorganic materials 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 abstract 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 239000008246 gaseous mixture Substances 0.000 abstract 1
- 229910052737 gold Inorganic materials 0.000 abstract 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 abstract 1
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 238000010926 purge Methods 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
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)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Paper (AREA)
Abstract
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.
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 |
|---|---|
| ES366867A1 true ES366867A1 (en) | 1971-06-16 |
Family
ID=10162679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES366867A Expired ES366867A1 (en) | 1968-05-06 | 1969-05-06 | 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) | DE1967147C2 (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) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4258216A (en) * | 1975-07-31 | 1981-03-24 | American Cyanamid Company | Vapor phase oxidation process for glyoxal |
| CA1064963A (en) * | 1975-07-31 | 1979-10-23 | American Cyanamid Company | Vapor phase oxidation process for glyoxal |
| 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 |
| DE2832405A1 (en) * | 1978-07-24 | 1980-02-14 | Basf Ag | METHOD FOR PRODUCING GLYOXAL FROM AETHYLENE GLYCOL |
| DE2922599A1 (en) * | 1979-06-02 | 1980-12-04 | Basf Ag | METHOD FOR THE CONTINUOUS PRODUCTION OF GLYOXAL |
| DE3012004A1 (en) * | 1980-03-28 | 1981-10-15 | Hoechst Ag, 6000 Frankfurt | METHOD FOR PRODUCING METHYLGLYOXAL |
| JPS5838227A (en) * | 1981-09-01 | 1983-03-05 | Mitsui Toatsu Chem Inc | Preparation of aldehyde |
| DE3213227A1 (en) * | 1982-04-08 | 1983-10-13 | Basf Ag, 6700 Ludwigshafen | METHOD 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 |
| 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 |
| DE3643469A1 (en) * | 1986-12-19 | 1988-06-30 | Basf Ag | METHOD FOR PRODUCING CARBONYL COMPOUNDS |
| DE3712856A1 (en) * | 1987-04-15 | 1988-11-03 | Basf Ag | METHOD FOR PRODUCING CARBONYL COMPOUNDS |
| RU2321577C2 (en) * | 2006-04-25 | 2008-04-10 | Институт органического синтеза УрО РАН | Method for preparing glyoxal-containing products |
| 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 |
| JP2009537479A (en) * | 2006-05-17 | 2009-10-29 | ビーエーエスエフ ソシエタス・ヨーロピア | Temperature control in the performance of hydrocarbon oxidation reactions. |
| DE102008018480B4 (en) | 2007-04-13 | 2020-10-15 | Basf Se | Process for the preparation of vicinal dioxo compounds by oxidation of vicinal dihydroxy compounds |
| 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 |
| RU2392170C1 (en) * | 2008-10-06 | 2010-06-20 | Геращенко Григорий Аркадьевич | Air boat lines element (versions) |
| EP2382175B1 (en) | 2008-12-29 | 2015-02-25 | Basf Se | Process for purifying aqueous glyoxal solutions |
| US8461396B2 (en) | 2010-10-01 | 2013-06-11 | Basf Se | Process for purifying aqueous glyoxal solutions |
| CN103153929B (en) | 2010-10-01 | 2015-06-03 | 巴斯夫欧洲公司 | Process for purifying aqueous glyoxal solutions |
| EP4214185B1 (en) | 2020-09-17 | 2024-07-17 | Basf Se | Process for the production of glyoxal |
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 FR FR6914418A patent/FR2007925A1/fr active Pending
- 1969-05-06 BE BE732584D patent/BE732584A/xx not_active IP Right Cessation
- 1969-05-06 ES ES366867A patent/ES366867A1/en not_active Expired
- 1969-05-06 DE DE19691967147 patent/DE1967147C2/en not_active Expired
- 1969-05-06 BR BR20855169A patent/BR6908551D0/en unknown
- 1969-05-06 DE DE19691923048 patent/DE1923048C3/en not_active Expired
-
1972
- 1972-08-14 JP JP8137872A patent/JPS4930807B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1923048B2 (en) | 1979-07-19 |
| DE1967147B1 (en) | 1979-06-13 |
| DE1923048C3 (en) | 1980-06-19 |
| GB1272592A (en) | 1972-05-03 |
| DE1923048A1 (en) | 1969-11-20 |
| CH535193A (en) | 1973-03-31 |
| FR2007925A1 (en) | 1970-01-16 |
| SE363816B (en) | 1974-02-04 |
| NO133034B (en) | 1975-11-17 |
| DE1967147C2 (en) | 1980-02-14 |
| BR6908551D0 (en) | 1973-01-04 |
| NL168487C (en) | 1982-04-16 |
| JPS4930807B1 (en) | 1974-08-16 |
| NO133034C (en) | 1976-02-25 |
| NL6906866A (en) | 1969-11-10 |
| BE732584A (en) | 1969-11-06 |
| NL168487B (en) | 1981-11-16 |
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