GB973919A - New heterocyclic-aromatic hydroxy ketones - Google Patents
New heterocyclic-aromatic hydroxy ketonesInfo
- Publication number
- GB973919A GB973919A GB3231862A GB3231862A GB973919A GB 973919 A GB973919 A GB 973919A GB 3231862 A GB3231862 A GB 3231862A GB 3231862 A GB3231862 A GB 3231862A GB 973919 A GB973919 A GB 973919A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- group
- hydroxy
- compounds
- alkyl group
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
- C09K15/14—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen containing a phenol or quinone moiety
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/09—Sulfur-containing compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
- G03C1/8155—Organic compounds therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Textile Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises the heterocyclic-aromatic hydroxy ketones of the formula <FORM:0973919/C1/1> where X represents hydrogen, an alkyl group with 1-4 carbon atoms, a phenyl or a halogenated phenyl group, Y represents a free or etherified hydroxyl group and Z1 and Z2 may be identical or different and each represents a hydrogen atom or an alkyl group containing 1-4 carbon atoms. The compounds are prepared by known methods, e.g. from the corresponding thiophene carboxylic acid or acid halide and the appropriate m-dialkoxy-benzene using a specified catalyst or by esterifying the m-alkoxyphenol with the thiophene carboxylic acid or acid halide and subsequently rearranging the ester to the o-hydroxy ketone by treatment with a Friedel-Crafts catalyst. When the m-dialkoxy benzenes are used the reaction conditions are usually such that both the etherified hydroxyl groups are split off. The resulting d-hydroxy ketone can be etherified by conventional methods, e.g. with alkyl halides. When the acid halides are used in the first of the above methods any Friedel-Crafts catalyst can be employed, but for the reaction of the free acids with the di-alkoxy-benzenes borofluorine compounds, especially borontrifluoride, are necessary. The compounds of the invention can be used as dye intermediates, but are most useful as light filters to protect a wide variety of materials from U.V. radiation (see Divisions A5, B5, C3, D1, D2 and G2). Examples 1-7 describe the preparation of compounds of the above formula in which Z1, Z2 and X are hydrogen and Y is an hydroxy, propoxy, isoamoxy or octoxy group, where Z1 and Z2 are hydrogen, Y is a hydroxy group and X is phenyl or 2, 5-dichlorophenyl and where Z1 is hydrogen, Z2 and X are methyl groups and Y is a hydroxyl group, the etherified compounds being obtained by alkylation of the corresponding free hydroxy compounds.ALSO:Macromolecular compounds are protected from U-V radiation by incorporation of a hydroxyketone of the formula <FORM:0973919/C3/1> wherein X represents hydrogen, a C1-C4 alkyl group, a phenyl or halogenated phenyl group, Y represents a free or etherified hydroxyl group and Z1 and Z2 are the same or different and each can represent hydrogen or a C1-C4 alkyl group. Protection may be effected by incorporating the light filter in the addition or condensation polymer before, during or after polymerization. Numerous specified materials include cellulose derivatives, addition polymers, e.g., polyvinyl chloride, polypropylene, polyethylene and polyacrylonitrile, condensation polymers, e.g. polyamides, polyesters, and phenol, urea and melamine-formaldehyde resins, natural and synthetic resins, e.g. epoxy, vinyl, and natural and synthetic rubbers, e.g. balata, guttapercha, polychloroprene, olefinic polysulphides, polybutadiene and its co-polymers. Example (10) describes the treatment of a hexamethylenediamine adipate polyamide mixed with titanium dioxide with a hydroxy ketone in which X, Z1 and Z2 are hydrogen and Y is a propoxy group and Z2 are hydrogen and Y is a propoxy group or Z1 and Z2 are hydrogen, Y is hydroxy and X is a 2, 5-dichlorophenyl group and extrusion of the resulting mixture. In Example 11 the hydroxy ketone in which X, Z1 and Z2 are hydrogen and Y is an octoxy group is added to a paste of polyvinylchloride and dioctyl phthalate prior to forming a foil.ALSO:Compounds which are light filters and which may be incorporated in cosmetics, e.g. perfumes, bath salts, skin and face creams, powders, insect repellants and especially suntan oils and creams, to give protection against U.V. radiation, comprise hydroxy ketones of the formula <FORM:0973919/A5-A6/1> wherein X represents hydrogen, a C1-C4 alkyl group or a phenyl or halogenated phenyl group, Y represents a free or etherified hydroxyl group and Z1 and Z2 are the same or different and represent hydrogen or a C1-C4 alkyl group.ALSO:Textile materials, paper, paper stock and wood are protected from U.V. radiation by the incorporation of 0.1-5% of a hydroxy-ketone of the general formula <FORM:0973919/D1-D2/1> where X represents hydrogen, an alkyl group containing up to 4 carbon atoms, a phenyl or halogenated phenyl group, Y represents a free or etherified hydroxyl group and Z1 and Z2 may be identical or different and each can represent hydrogen or an alkyl group containing up to 4 carbon atoms. The textiles may be in any desired form, e.g. filaments, fibres, yarns, woven, knitted or felt and may consist of natural materials such as wool, silk, cotton, hemp, linen, jute or ramie, semisynthetic materials, e.g. rayon, including spun rayon, viscoses or regenerated cellulose or they may be synthetic textiles obtained from addition polymers, e.g. polyacrylonitrile, polyethylene or polypropylene or from polycondensates such as polyesters or polyamides. The light filter can also be incorporated in coating and dressing agents such as those based on starch and casein. In Example 9 a fabric of polyamide fibres, prepared from hexamethylenediamine and adipic acid, is treated in a water/ethanol solution containing the adduct of 35 mols. ethylene oxide to 1 mol. stearyl alcohol with a hydroxy ketone in which X1 Z1 and Z2 are hydrogen and Y is a propoxy group. In Example 12 a fancy paper prepared from a stock containing bleached sulphite or sulphate cellulose, zinc sulphide, aluminium sulphate, a paste containing an azo dye and water is covered with an untreated tissue or overlay paper and immersed in a bath consisting of a condensation product of melamine and formaldehyde and a solution of the hydroxy ketone, in which X, Z1 and Z2 are hydrogen and Y is a hydroxyl group, in dimethylformamide and water. After removing excess resin and drying the paper is pressed together with a phenol paper and blocking sheets impregnated with melamine resin to give a laminate with improved fastness to light.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1046861A CH428728A (en) | 1961-09-08 | 1961-09-08 | Use of heterocyclic aromatic oxyketones as protective agents against ultraviolet radiation |
Publications (1)
Publication Number | Publication Date |
---|---|
GB973919A true GB973919A (en) | 1964-11-04 |
Family
ID=4363550
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3231862A Expired GB973919A (en) | 1961-09-08 | 1962-08-22 | New heterocyclic-aromatic hydroxy ketones |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE622243A (en) |
CH (1) | CH428728A (en) |
ES (1) | ES280614A1 (en) |
GB (1) | GB973919A (en) |
NL (1) | NL282996A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0046337A2 (en) * | 1980-08-20 | 1982-02-24 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
US5290952A (en) * | 1991-07-03 | 1994-03-01 | Ciba-Geigy Corporation | Phenylthiophenyl ketones |
US20120203012A1 (en) * | 2009-12-28 | 2012-08-09 | Canon Kabushiki Kaisha | Heteroaromatic-containing compound, optical material and optical element |
-
0
- NL NL282996D patent/NL282996A/xx unknown
- BE BE622243D patent/BE622243A/xx unknown
-
1961
- 1961-09-08 CH CH1046861A patent/CH428728A/en unknown
-
1962
- 1962-08-22 GB GB3231862A patent/GB973919A/en not_active Expired
- 1962-09-07 ES ES280614A patent/ES280614A1/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0046337A2 (en) * | 1980-08-20 | 1982-02-24 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
EP0046337A3 (en) * | 1980-08-20 | 1982-09-15 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
US5290952A (en) * | 1991-07-03 | 1994-03-01 | Ciba-Geigy Corporation | Phenylthiophenyl ketones |
US20120203012A1 (en) * | 2009-12-28 | 2012-08-09 | Canon Kabushiki Kaisha | Heteroaromatic-containing compound, optical material and optical element |
US8609869B2 (en) * | 2009-12-28 | 2013-12-17 | Canon Kabushiki Kaisha | Heteroaromatic-containing compound, optical material and optical element |
Also Published As
Publication number | Publication date |
---|---|
CH428728A (en) | 1967-01-31 |
NL282996A (en) | |
ES280614A1 (en) | 1963-03-01 |
BE622243A (en) |
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