Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
  • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
  • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
  • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
  • C07D263/57—Aryl or substituted aryl radicals
• • 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
• • 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
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
  • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
• • 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
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
  • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
  • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
• • 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
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • 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
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
  • C08K5/3445—Five-membered rings
  • C08K5/3447—Five-membered rings condensed with carbocyclic rings
• • 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
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen 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
  • C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B5/00—Preserving by using additives, e.g. anti-oxidants
  • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
  • C11B5/0064—Heterocyclic compounds containing nitrogen in the ring
• • 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
  • D06M13/35—Heterocyclic compounds
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts 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
  • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
  • D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments

Definitions

• the present invention provides new phenylbenzazoles which, like, for example, the compound of the formula O -OH3 (1 are substituted by at least one branched alkyl group.
• 2- phenylbenzazoles includes 2-pheny-lbenzoxazoles, 2-phenyl-benzthiazoles and Z-phenylbenzimidazoles.
• the new phenyl-benzazoles containing at least one branched alkyl group are suitable for use as agents affording protection from ultra-violet rays, more especially to the skin.
• the products of the present invention contain at least one branched alkyl group which may contain one or several branchings and 3, up to for example 12, carbon atoms.
• the molecule of the phenylbenzazole contains only one branched alkyl group, the latter may be bound either to the phenyl radical in position 2 or to the benzene radical condensed with the azole ring.
• Azole compounds containing 2 branched alkyl groups may contain, for example, one of them in the phenyl radical and the other in the benzene radical condensed with the azole ring.
• the branching may be in any desired position of the alkyl radical.
• the branching begins immediately with the carbon atom of the alkyl group bound to the benzene nucleus so that it is either secondary [CH a1kyl) or preferably tertiary [-C(alkyl)
• the alkyl radical is an isopropyl group [CH(CH)
• branched radicals may be mentioned, for example, isobutyl or isoamyl radicals, the branched octyl radical of the formula and more especially the tertiary butyl radical of the formula
• 2-phenylazole compounds contain in addition to one or if desired more than one branched alkyl radical as further substituents in the benzene nuclei at most only unbranched alkyl groups and/or chlorine atoms.
• unbranched alkyl groups there may be mentioned above all the lower groups with 1 to 4 carbon atoms, more especially the methyl and ethyl groups.
• These azole compounds correspond to the formula in which R represents a benzene radical in which two vicinal cyclic carbon atoms are at the same time also members of the azole ring, R represents a benzene radical 3,95,422 Patented June 25, 1963 ice and X the complement to the azole ring, with the molecule containing as substituent at least one branched alkyl group and the benzene nuclei R and R contain as further substituents at most only unbranched alkyl groups and/ or chlorine atoms.
• 3 and 4 X represents the complement to the azole ring, that is to say in the case of the oxazoles an oxygen atom, in the case of the thiazoles a sulfur atom, and in the case of the imidazoles a nitrogen atom which has in addition to the two cyclic bonds also a bond to a hydrogen atom or to a substituent.
• the 2-phenyl-benzimidazoles correspond preferably to the formula in which R and R have the meanings shown above in connection with the Formula 2 and Y represents an alkyl group such as a methyl or ethyl group, or a hydroxyalkyl group such as a ,Bw-dihydroxypropyl or fi-hydroxypropyl group, or a benzyl radical, or preferably a hydrogen atom.
• R and R have the meanings shown above in connection with the Formula 2 and Y represents an alkyl group such as a methyl or ethyl group, or a hydroxyalkyl group such as a ,Bw-dihydroxypropyl or fi-hydroxypropyl group, or a benzyl radical, or preferably a hydrogen atom.
• acyl compound derived on one hand from a benzenecarboxylic acid and on the other hand from 'an ortho-aminohydroxybenzene, ortho-aminomer- 3 captolbenzene or ortho-diaminobenzene of which one amino group is primary and the other at most secondary, said acyl compound being substituted by at least one branched alkyl group, water is eliminated by heating and/or treatment with a water-eliminating agent, for example
• the acyl compounds required as starting materials for this reaction can be prepared by reacting an orthoaminohydroxybenzene, ortho-aminomercaptobenzene or ortho-diaminobenzene of the indicated type with a henzenecarboxylic acid halide, preferably an acid chloride, at least one of the two starting materials being substituted by a branched alkyl group.
• the elimination of water from the acyl compound can be accomplished, tor example, by simple heating, or more advantageously with the aid of a
• acyl compound derived on one hand from a benzene carboxylic acid and on the other hand from an ortho-nitrohydroxybenzene, ortho-nitromercaptobenzene o-r 'ortho-nitroaminobenzene containing an amino group which is at most secondary, which acyl compound contains at least one branched alkyl group, is treatedwith a water-eliminating reducing agent, for example at 90- 100 C. with tin and hydrochloric acid.
• the acyl compounds (esters, thioesters or amides) required as starting materials can be prepared from the nitro compounds of the specified kind and benzenecarboxylic acid halides.
• method A, B or C When it is desired to manufacture Z-phenylbenzimidazoles substituted at one of the imidazole nitrogen atoms by a branched alkyl group, method A, B or C may be employed, using as starting material a suitable l-aminoor 1-nitro-2-N-alkylbenzoylaminobenzene or l-amino-Z- alkylaminobenzene.
• a 2-phenylbenzimidazole containing an imidazole ring nitrogen atom bound to a hydrogen atom may be reacted with an alkylating agent containing a branched alkyl group, for example G- Q hydrogen halide This reaction is advantageously carried out in the presence of an acid acceptor.
• the light filter is incorporated in a substratumfor the purpose of protecting the latter from the attack by manufacture of the latter or subsequently by way of a suitable operation, for example by a fixation process similar to a dyeing process.
• the light filter is incorporated in a substratum to protect one or several other substances incorporated in the substratum such, for example, as dyestuffs or assistants, and this may be accompanied by the'protection of the-substratum mentioned under A above.
• the light filter is incorporated in a filter layer for the purpose of protecting an underlying substratum or a substratum which is at some distance from the filter layer (-for example in a shop window) from the attack of the ultra-violet rays;
• the filter layer may be solid (a film, foil or dressing) or it may be semi-solid (a cream, oil or wax).
• Textile materials quite generally which may be in any desired form, for example in the form of fibers, filaments, yarns, woven or knitted fabrics or felt, and all products made therefrom.
• Such textile materials may consist of'na-tural materials of animal origin such as wool or silk, or of vegetableorigin such as cellulosic .materials of cotton hemp, flax, linen, jute'or ramie;
• semi-synthetic materials such as regenerated cellulose, for example rayon, viscose rayon, including spun rayon, or fully synthetic materials accessible by polymerization or copolymerization, for example polyacrylonitrile, or products obtained by polycondensation such as polyesters and above all polyarnides.
• semi-synthetic materials it is of advantage to add the light filter to the spinning solution, for example a viscose spinning solution, acetyl cellulose (including cellulose triacetate) spinning composition; in the case of masses destined for the manufacture of fully synthetic fibers, such :as polyamide melts or polyacrylonitrile spinning compositions, it is of advantage to incorporate the light filter before, during or after the polycondensation or polymerization respectively.
• Fibrous materials of a different nature not being textile materials, which may be of animal origin such as feathers, hairs, skins and hides and leathers made from the latter by natural or chemical tanning, as well as products made therefrom; or they may be of vegetable origin such as straw, wood, Wood pulp or materials made from densified fibers such as paper, cardboard or hardboard, as well as materials made therefrom; furthermore paper pulp (for example hollander pulp) used for the manufacture of paper.
• animal origin such as feathers, hairs, skins and hides and leathers made from the latter by natural or chemical tanning, as well as products made therefrom
• they may be of vegetable origin such as straw, wood, Wood pulp or materials made from densified fibers such as paper, cardboard or hardboard, as well as materials made therefrom; furthermore paper pulp (for example hollander pulp) used for the manufacture of paper.
• Coating and dressing materials for textiles and papers for example those based on starch or casein or on synthetic resins, for example of vinyl acetate or derivatives of acrylic acid.
• Lacquers and films of various compositions for example consisting of acetyl cellulose, cellulose propio nate, cellulose butyrate and cellulose mixtures such, for example, as cellulose acetate-butyrate and cellulose acetate-propionate; also nitrocellulose, vinyl acetate, polyvinyl chloride, copolymers of vinyl chloride and vinylidene chloride, alkyl resins, polyethylene, polyamides, polyacrylonitrile and polyesters.
• the azole compounds are of special importance for incorporation in wrapping materials, more especially in the known transparent foils of regenerated cellulose (viscose) or acetyl cellulose. In this case it is as a rule of advantage to add the light filter to the mass from which such foils are manufactured.
• Natural or synthetic resins for example epoxy resins, polyester resins, vinyl resins, polystyrene resins, alkyl resins, aldehyde resins such as condensation products of formaldehyde With phenol, urea or melamine; as Well as emulsions of synthetic resins (for example oil-in- Water or water-in-oil emulsions).
• synthetic resins for example oil-in- Water or water-in-oil emulsions.
• the light filter is advantageously applied before or during the polymerization or polycondensation respectively.
• Mention may also be made of synthetic resins reinforced with glass fibers and laminates made therefrom.
• Hydrophobic substances containing oils, fats or waxes such as candles, floor polishes, floor stains or other wood stains, furniture polishes, more especially those to be used for treating pale-colored, if desired bleached, wood surfaces.
• Natural rubber-like materials such as rubber, balata, gutta percha or synthetic vulcanizable materials such as polychloroprene, olefinic polysulfides, polybutadiene or copolymers of butadiene and styrene (for example Buna S) or butadiene and acrylonitrile (for example Buna N), which may additionally contain fillers, pigments, vulcanization accelerators and other assistants and in which the addition of the azole compounds of the invention is intended to delay the ageing and the attendant deterioration of the plasticity properties and embrittlement.
• synthetic vulcanizable materials such as polychloroprene, olefinic polysulfides, polybutadiene or copolymers of butadiene and styrene (for example Buna S) or butadiene and acrylonitrile (for example Buna N), which may additionally contain fillers, pigments, vulcanization accelerators and other assistants and in which the
• the light filters are suitable not only for use with undyed but also with dyed or pigmented materials.
• the protection extends also to the dyestuffs so that in some cases a very substantial improvement of the fastness to light is 6 achieved.
• the treatment with the light filter may be combined with the dyeing or pigmenting operation.
• the amount of light filter to be incorporated in the material concerned may vary within relatively wide limits, for example from about 0.01 to 10%, preferably from 0.1 to 2%, of the material that is to be protected directly from the ultra-violet rays.
• the phenylbenzazoles are particularly suitable for protecting the skin from ultra-violet rays. They can be made up in the usual manner into stable cosmetics ready for application. Advantageously, they are mixed, emulsified or preferably dissolved in a suitable vehicle.
• a suitable vehicle may be liquid or semisolid.
• Relevant compounds are liquid organic diluents, for example organic solvents such as alcohols and ketones, for example ethanol, isopropanol, glycerol, cyclohexanol, methylcyclohexanol; furthermore trichloroethylene, petroleum products, esters of vegetable or animal origin such as vegetable or animal oils and fats, for example groundnut oil, cocoa butter and lanolin.
• mineral solvents such as paraffin oil, white mineral oil, or white petroleum jelly.
• the latter can be finely dispersed directly in water with the aid of a suitable dispersant or completely or partially dissolved in one of the aforementioned organic vehicles and then dispersed or emulsified in water.
• a suitable dispersant or completely or partially dissolved in one of the aforementioned organic vehicles and then dispersed or emulsified in water.
• Such mixtures and preparations may also contain further substances, for example skin creams, insect repellants, deodorants, aromatic substances and dyestuffs.
• the Z-phenylbenzazoles to be used as protective agents according to the present invention are particularly suitable for use as skin protectives because, on one hand, they are readily soluble in such organic solvents as are used for cosmetic purposes and, on the other hand, they absorb extensively ultra-violet rays of a wavelength up to about 320 m which redden the skin, While they have no influence on rays of a higher wavelength (320 to about 400 m which tan the skin, as is generally desirable.
• Example 1 35 .6 parts of para-tertiary butylbenzoic acid, 21.6 parts of 1:2-diaminobenzene and 0.6 part of boric acid are stirred under nitrogen for 2 hours at 205-21 O C., and the water formed is continuously distilled oil. The melt is cooled to C. and 2 00 parts of dimethyl formamide are added dropwise, whereupon a dark brown solution is formed.
• the product can be used as a substance aifording protection from ultra-violet rays, more especially as a skin protective.
• Other compounds, shown in the following table, can be produced in the manner described above and used for the indicated purpose.
• Example 2 lizations from aqueous alcohol, melts at 113-1135 C.
• Example 1 When in Example 1 1:2-diaminobenzene is replaced by an equivalent amount of l-hydroxy-Z-aminobenzene there is obtained the product of the formula Example 3 8.3 parts of 1-hydroxy-2-amino-4-tertiary butylbenzene,
• .of adipic acid isopropyl tetrahydrofurfuryl ester and 1 part of glycerol monostearate are dissolved in 84 parts of ethanol.
• the solution affords protection from sunrays and repels insects and isvexcellently suitable for rubbing into exposed parts of thebody.
• one of the compounds (9) to (15) can be used with asimilar Example 5
• a solution of 4 parts of the compound of the Formula 1' in 96 parts of ethanol is treated with 0.5 part of essential oils. 40 parts of the resulting solution, together with 60 partsof a mixture of equal parts of trichloromono- Example 6 10 parts of adipic acid ,isopropyl tetrahydrofurfuryl ester, 5 parts of benzoic acid diethylamide, 8 parts of phthalic acid, dimethyl ester and '5 parts of one.
• of the compounds of the Formulae 1 or 9 to 15 are dissolved m a mixture of 3 6 parts of groundnut oil and 36 parts ofparafiin oil.
• the resulting product isa sunburn preparation which also repels insects.
• Example 7 An intimate mixture is prepared from 4 parts of one of the compounds of the Formulae 1 or 9 to 15, 10 parts of glycerol monostearate, 4 parts of cetyl alcohol, 1 part of sodium cetyl sulfate, 1 part of stearic acid and 5 parts of glycerol and emulsified in 75 parts of water.
• the resulting emulsion is a very efficient non-greasy skin cream and protects the skin treated with it from sunburn.
• Example 8 An intimate mixture is prepared from 5 parts of adipic acid isopropyl tetrahydrofurfuryl ester, 5 parts of toluylic acid diethylamide, 3 parts of one of the compounds of the Formulae 1 or 9 to 15, 6 parts of cetyl alcohol, 14 parts of paraffin oil, 10 parts of white beeswax, 14 parts of lanoline, 3 parts of cocoa butter, 39.7 parts of water and 0.3 part of sodium benzoate. The resulting cream protects the skin from sunburn and repels insects.
• Example 9 A film of a thickness of about 40 is prepared from a solution in acetone of 10% strength of acetyl cellulose containing 1% of the compound of the Formula 14 calculated on acetyl cellulose. After having been dried, part of the resulting film is exposed for 100 hours in a fadeometer. The following values of permeability in percent are found:
• the oil phase A is melted, heated to 70 C. and vigorously stirred into the aqueous phase B which is heated at 75 C.
• the emulsion is rinsed cold and perfumed (0.3 part of perfume).
• Example 1 1 A solution is prepared in the usual manner from Parts Compound of one of the Formulae 1 or 9 to 15 3 Polyethylene glycol, molecular weight 300 40 Propylene glycol 25 Isopropyl myrist 2.5 Ethanol 29.2 Perfume 0.3
• This solution protects the skin from ultra-violet rays. It is advantageously applied to the skin with the aid of a suitable sprayer.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Polymers & Plastics (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Medicinal Chemistry (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Wood Science & Technology (AREA)
• Microelectronics & Electronic Packaging (AREA)
• Physics & Mathematics (AREA)
• Condensed Matter Physics & Semiconductors (AREA)
• General Physics & Mathematics (AREA)
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• Computer Hardware Design (AREA)
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• Power Engineering (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Materials Engineering (AREA)
• Textile Engineering (AREA)
• Treatment And Processing Of Natural Fur Or Leather (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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• 1959
  • 1959-09-23 CH CH317661A patent/CH483276A/de not_active IP Right Cessation
• 1960
  • 1960-09-12 US US55122A patent/US3095422A/en not_active Expired - Lifetime
  • 1960-09-14 GB GB19727/60A patent/GB946728A/en not_active Expired
  • 1960-09-14 GB GB31716/60A patent/GB941990A/en not_active Expired
  • 1960-09-16 FR FR838732A patent/FR1279273A/fr not_active Expired
  • 1960-09-22 DE DEC22392A patent/DE1201953B/de active Pending
  • 1960-09-22 NL NL256123D patent/NL256123A/xx unknown

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