Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
  • C09B23/16—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
  • C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
  • C09B23/166—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing two or more nitrogen atoms
• • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/413—Indoanilines; Indophenol; Indoamines
• • 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
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
• • 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
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

• oxidation dyes or bases associated with dyeing modifiers or couplers which can be aromatic metadiamines or metaaminophenols, or pyrazolones or diketones.
• an oxidizing agent as hydrogen peroxide is added to the mixture of bases and couplers selected which has been previously alkalized.
• R is selected from the group consisting of hydrogen and lower alkyl having 1-4 carbon atoms, or R and R,,, taken together with the carbon atoms to which they are linked, form a benzene ring, a halogen-substituted benzene ring, a benzene ring substituted with lower alkyl having 14 carbon atoms, a benzene ring substituted with lower alkoxy having 14 carbon atoms or a nitrosubstituted benzene ring;
• B is selected from the group consisting of (i) a nitrogen-containing heterocycle different from the nitrogen containing heterocycle of A; (ii) a cycle of the formula wherein Y is a member selected from the group consisting of oxygen and wherein R and R each independently represent a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms and phenyl; and Z is an anion derived from
• the above-described hair dyeing compositions according to the present invention are aqueous solutions, to which most often have been added low molecular weight alcohols such as ethanol or isopropanol, or glycols such as propylene glycol or butylglycol, the alcohol or glycol facilitating the solution of the dye in the composition.
• alcohols such as ethanol or isopropanol
• glycols such as propylene glycol or butylglycol
• These solutions are easily prepared by dissolving one or more compounds of Formula I in water or in a water-alcohol mixture.
• the proportion of alcohol used is generally between and 70% by weight, while the proportion of glycol is generally between 1 and 6% by weight.
• the concentration of the dye or dyes of Formula I in the dyeing compositions according to the present invention can vary in broad limits, because of the great affinity of these compounds for keratinous fibers. This concentration is generally between about 0.001 and about 0.5% by weight and preferably between about 0.002 and about 2% by weight.
• the pH of the compositions according to the present invention is generally between about 2,5 and l0 and preferably between about 3 and 8.
• the pH is adjusted to the desired value by addition of an acid such as orthophosphoric acid, lactic acid or acetic acid or a base such as mono-, dior triethanolamine or ammonia.
• compositions according to the present invention can contain only one or more of the dyes of Formula I, in which case they make it possible to obtain on the hair shades rich in glints that go from yellow to blue, covering the light spectrum.
• the composition according to the invention can, however, contain other direct dyes, for example, azo or anthraquinone dyes, nitro dyes of the benzene series, indoanilines, indophenols or indamines.
• the hair-dyeing compositions according to the present invention can also contain various adjuvants and ingredients customarily used in capillary cosmetics, for example, wetting agents, dispersing agents, swelling agents, penetrating agents, thickeners, softeners or perfumes. They can also be packaged under pressure in aerosol bombs or containers, together with a conventional aerosol propellant such as dichlorodifluoromethane, trichloromonofluoromethane and their mixtures. Of course, other conventional aerosol propellants can be used.
• a conventional aerosol propellant such as dichlorodifluoromethane, trichloromonofluoromethane and their mixtures.
• other conventional aerosol propellants can be used.
• Dyeing of keratinous fibers, particularly human hair, with the dye compositions according to the invention can be performed in the usual way, by application at ambient temperature of the composition to the fibers to be dyed, the composition being left in contact for a period varying from 3 to 30 minutes. Following this application, the fibers are rinsed and, if desired, washed. Thereafter the treated fibers are dryed.
• the compounds of Formula I can be employed in the production of capillary setting lotions.
• These lotions comprise an aqueous dilute alcohol solution, at least one cosmetic resin and at least a compound of Formula I or a salt thereof as defined above.
• the setting lotions according to the invention generally contain from 20 to by weight of the total hairsetting lotion composition, of a low molecular weight alkanol such as ethanol or isopropanol and from i to 3% by weight of cosmetic resin.
• Representative cosmetic resins that can be employed in the hair-setting lotions of the present invention include, for instance, polyvinyl pyrrolidone having a molecular weight of 40,000-400,000, copolymer of crotonic acid and vinyl acetate, said copolymer having a molecular weight ranging from about 10,000 to 70,000, copolymer vinyl pyrrolidone and vinyl acetate, wherein the ratio of PVP to VA ranges between 50-70: 5030, said copolymer having a molecular weight ranging from about 30,000 to 200,000 and maleic anhydridebutylvinyl ether copolymers, a 1% solution of which is methylethyl ketone has a viscosity of 0.1-3.5 cps at 25C. These resins are used in a proportion of l to 3% by weight of the hair-setting lotion composition.
• the pH of the hair setting lotions according to the invention is generally between 3 and 8. As stated above, it is possible to regulate the pH to the desired value by using mono or di or triethanolamine and an acidifying agents, acetic acid or lactic acid.
• the setting lotions according to the invention can contain only the dyes of Formula I, in which case they constitute what is known as shading compositions.
• the hair-setting lotions of this invention can also contain other direct dyes such as anthraquinone dyes, nitro dyes of the benzene series and those mentioned above.
• the hair-setting lotions can also contain various ingredients usually'used in capillary cosmetics, for example, wetting agents, dispersing agents, swelling agents, penetrating agents, thickeners, softeners or perfumes, as mentioned above.
• the hair-setting lotions disclosed herein are used in the customary manner by applying at ambient temperature to wet hair that has been previously washed and rinsed, followed by rolling the hair up on curlers and drying of the hair.
• the dyes of Formula I can also be used in the production of hair lacquers.
• These lacquers contain in alcohol solution at least one cosmetic resin and at least a compound of Formula I.
• the alcohols suitable for the preparation of the hair lacquers according to the invention are low molecular weight alcohols, such as ethanol or isopropanol.
• resin there may be used one or more of polyvinyl pyrrolidone, copolymer of crotonic acid and. vinyl acetate, copolymer of vinyl pyrrolidone and vinyl acetate, copolymer of maleic anhydride and butylvinyl ether, all as described above.
• the amount of dye of Formula I ranges from about 0.00l to about 0.5% by weight and the amount of cosmetic resin used is between about 1 and 3% by weight.
• the hair lacquers of the present invention are conveniently packaged in pressurized containers or aerosol bombs of the type described above.
• the hair lacquers are conveniently applied directly to the hair, preferably in the form of a spray at ambient temperature.
• the present invention in the composition of matter aspect thereof, includes novel diazamerocyanines and salts thereof of the formula A N N B (1') wherein A is a nitrogen heterocycle as defined above and B is a residue corresponding to one of the following formulae:
• X represents an anion derived from an inorganic or organic acid
• R is selected from the group consisting of hydrogen or lower alkyl having 1-4 carbon atoms
• R is hydrogen, lower alkyl having 1-4 carbon atoms. lower alkyl having 14 carbon atoms substituted by an amine. lower alkyl having l-4 carbon atoms substituted by an amide, and
• W is selected from the group consisting of oxygen and sulfur. and R is selected from the group consisting of amino and lower alkyl of l-4 carbon atoms, R1, and R each independently represent a member selected from the group consisting of hydrogen and lower alkyl having 14 carbon atoms; Y represents a member selected from the group consisting of wherein R, and R each independently represent a member selected from the group consisting of hydrogen and lower alkyl having l-4 carbon atoms, and Z is an anion derived from an inorganic or organic acid. such as halide. perchlorate, fluoborate. acetate. bisullate and sulfate;
• R represents a member selected from the group consisting of hydrogen and wherein W represents a member selected from the group consisting of oxygen and sulfur, and R represents a member selected from the group consisting of amino and lower alkyl having 1-4 carbon atoms, R and R each independently represent a member selected from the group consisting of hydrogen, lower alkyl having l-4 carbon atoms and methoxy, provided that R represents hydrogen when R',, R and R,-, represent hydrogen, R and R together with the carbon and nitrogen atoms to which they are attached, represent a member selected from the group consisting of a saturated heterocycle containing 5 ring atoms, an unsaturated heterocycle containing 5 ring atoms, a saturated heterocycle containing 6 ring atoms, an unsaturated heterocycle containing 6 ring atoms, in which case R represents hydrogen and R represents a member selected from the group consisting of hydrogen and lower alkyl having l-4 carbon atoms;
• R and R together with the nitrogen atoms to which they are attached represent a member selected from the group consisting of a saturated heterocycle containing 5 ring atoms, an unsaturated heterocycle containing 5 ring atoms, a saturated heterocycle containing 6 ring atoms, an unsaturated heterocycle containing 6 ring atoms, in which case R represents hydrogen and R represents a member selected from the group consisting of hydrogen, lower alkyl having l-4 carbon atoms and acyl having 2 to 5 carbon atoms.
• Y designates a residue -NHR or kaline medium or an acid medium, in case it is desired to obtain a compound with a quaternary ammonium group.
• the acid used can be that corresponding to the desired salt, or a different acid, in which case the condensation is followed by an addition to the reaction medium ofa salt of the acid corresponding to the desired diazamerocyanine salt that is more soluble in water than said diazamerocyanine salt, which is then isolated by filtering.
• This method of preparation has been generally described by S. Hunig in Angewandte Chemie, International Edition, Volume 7, pages 335-344 (1968), the disclosure of which is hereby incorporated by reference.
• Example 2 In a manner similar to that of Example 1. but using 2,6-dimeth vl phenol for the 2-amino-6-methyl phenol, the above-indicated dye is obtained in form of a bright red solid with a melting point of236. Molecular weight was calculated in a similar manner as Example 1 and found by potentiometric determination to be 300 (theory: 297).
• a red product is obtained with a melting point of 238.
• a red product is obtained with a melting point of 240.
• a product with green glints is obtained with a melting point of 230.
• a product with green glints is obtained with a melting point of 242.
• the dye is obtained in the form of a reddish violet solid with a melting point of 180 (decomposition).
• ANN-116 is prepared in a manner identical with that of Example 9, except that 1,3-diamino 2.6-dimethyl phenol is cmployed.
• the dye is isolated in the form of a reddish violet solid with a melting point of 170 (decomposition).
• Example 2 is prepared in a manner identical with that of Example 1 1, except that 1,3-dimethyl 2,3-dihydro benzimidazolone hydrazone is employed.
• the dye is isolated in the form of a reddish orange product with a melting point of 268.
• EXAMPLE l3 1,2-dimethyl 2,3-dihydro 2:4'-azino indazole l'- phenyl 3'-methyl 4-pyrazolone of the below formula ii N 01/ Jana is prepared in a manner similar to that of-Example 11.
• the dye is obtained in the form of a brownish orange product with a melting point of 264.
• EXAMPLE l4 4-methyl 3-phenyl 2,3-dihydro 2:4-azino thiazole lphenyl 3-methyl 4'-ylidene 5-pyrazolone of the below formula is prepared in a manner as described by S. Huenig in Liebigs Annalen der Chemie,' Vol 636, p. 27, the disclosure of which is hereby incorporated by reference.
• a dye is obtained in the form of a deep violet solid with a melting point of 213.
• the dye is obtained in the form of a solid with green glints with a melting point of 225.
• N-CHa 2.12 g of 1,2-dimethyl 3-indaz0lone hydrazone hydrochloride are dissolved in cc ofwater. At ambient temperature a solution of 1.5] g of 6-hydroxy benzomorpholine in 80 cc of water is added, then, with stirring, in 15 minutes a solution of 4.56 g of ammonium persulfate and 12 cc of ammonia at 22Be is added. Stirring is continued for 30 minutes, followed by filtering, washing with cold water and drying of the precipitate thus obtained on phosphoric anhydride. The product obtained is a brownish red dye with a melting point of 230.
• Example 17 is prepared in a manner identical with that described in Example 17.
• the dye is obtained in the form ofa brown solid with green glints having a melting point of 184.
• Example 17 is prepared in a manner identical with that described in Example 17.
• the dye is obtained in the form of a brown solid with a melting point of 195.
• EXAMPLE 21 7 "-(6 hydroxy benzomorpholine) 2-az o 3-methyl benzothiazolium perchlorate'is obtained by dissolving of the chloride prepared in Example 20 in a suitable quantity of acetic acid and reprecipitation by sodium perchlorate.
• the melting point was found to be 240C (decomposition).
• EXAMPLE 22 3.45 g (0.01 mole) of 4-methyl 3-phenyl thiazolone benzene sulfonylhydrazone and 1.51 g (0.01 mole) of 6-hydroxy benzomorpholine are dissolved in cc of crystallizable acetic acid. Thereafter, in 15 minutes about 2.28 g (0.01 mole) of ammonium persulfate in 10 cc of water is added and the solution takes on a violet tint. The reaction mixture is stirred for 30 minutes, then 5 cc of sodium perchlorate dissolved in 20 cc of water are added. The reaction mixture is again stirred for 1 hour, then filtered and dried under vacuum on phosphoric anhydride.
• the product is purified by dissolving in a suitable quantity of dichlorethane, filtering of the insoluble material and reprecipitation by carbon tetrahydrochloride.
• a powder with green glints is obtained with a melting point of 230.
• the product is purified by dissolving in a sufficient quantity of dichlorethane and precipitation by carbon tetrachloride, there being obtained crystals with green glints with a melting point of C.
• EXAMPLE 24 25 10 g (0.04 mole) of N,N-dimethyl benzimidazolone hydrazone dihydrochloride and 6.04 g (0.04 mole) of -hydroxy benzomorpholine are dissolved in 250 cc of acetic acid. g of sodium acetate dissolved in 100 cc of acetic acid are added and then, in about 30 minutes, 30 18.24 g (0.08 mole) of ammonium persulfate dissolved in 100 cc of water are added. The mixture is allowed to react for 30 minutes, then the inorganic salts are separated by filtering and the product is precipitated by addition of 20 g of sodium perchlorate dissolved in 300 cc of water. 9 g of the product are collected, corresponding to a yield of 70%, which is purified by extraction with methanol and concentration. The melting point was found to be 240C.
• This hair-setting lotion when applied to hair dyed brown, imparts thereto a purplish brown shade.
• Example 7 0.1 g Vinyl acetate-crotonic acid copolymer (vinyl acetate-90% crotonic acid- 10 7!, molecular weight 45,000 50,000)
• Example 7 Vinyl pyrrolidone-vinyl acetate copolymer (vinyl pyrrolidone 7:, vinyl acetate 30 7:, molecular weight Ethyl alcohol, 96 titer 200 volume hydrogen peroxide Orthophosphoric acid, q.s.p.
• This hair-setting lotion is applied at ambient temperature to naturally light brown hair. After setting and drying, the hair is lightly brightened and imparts thereto a pearly glint,
• Dye of Example 7 0.0015 g Ethyl alcohol, 96 titer 50 cc 200 volume hydrogen peroxide 5 g Orthophosphoric acid, q.s.p. pH 3 Water, q.s.p. 100 cc This composition is applied to naturally dark blond hair. After setting and drying the hair is lightlybrightened up and the lotion imparts thereto anash rose glint.
• EXAMPLE 29 The following dyeing composition is prepared Dye of Example 1 0.0006 g Dye of Example 8 0.0006 g Vinyl acetate-crotonic acid copolymer (vinyl acetate /z. crotonic acid 10 7(, molecular weight 45,000 50,000) 2 g Ethyl alcohol, 96 titer 55 cc 200 volume hydrogen peroxide 5 g Orthophosphoric acid, q.s.p. pH 3 Water, q.s.p. 100 cc This lotion is applied to natural blond hair. After setting and drying, the hair is brightened and presents an ash pearly blond shade.
• EXAMPLE 30 The following dyeing composition suitable for packaging in an aerosol container is prepared:
• Example 4 Dye of Example 1 Vinyl pyrrolidone-vinyl acetate copolymer (vinyl pyrrolidone 60 vinyl acetate- 40 7:, molecular weight 45,000 60,000) 3 g Ethyl alcohol, 96 titer. q.s.p. 100 cc
• This composition packaged in an aerosol container with dichlorodifluoromethane as the propellant and 20 g of water are added to 20 g of the solution thus sprayed in the form of a lacquer gives natural blond prepared. A gel is obtained which, applied at ambient hair luminous golden glints.
• Dye of Example 1 I 0.005 g Dye of Example l 0.01 g Dye of Example 8 0.00] g Vinyl pyrrolidone-Vin l acetate copolymer (Vinyl pyrrolidone 7:, vinyl acetate 40 71, molecular weight Ethyl alcohol, 96 titer 50 cc Triethanolamine, q.s.p. pH 7 Water, q.s.p. I00 cc This hair-setting lotion when applied to freshly bleached hair, imparts thereto a light silvery shade EXAMPLE 32 The following dyeing composition is prepared:
• Dye of Example 17 0.2 Butylcellosolre 8 g Propylene glycol 8 g Alkylphenol polyethoxyether sold under the name "Remcopal 334" by the Gerland company 22 g Alkylphenol polyethoxyether sold under the name Remcopal 349- by the Gerland company 22 g Ammonia at 22Be 10 g Water. q.s.p. l00 g g g g 20 g of water are added to 20 g of the solution thus temperature for l0 minutes to previously bleached hair, imparts to the hair an iridescent blond shade.
• Example 24 0,0l0 g Vinyl pyrrolidone-vinyl acetate copolymer (vinyl pyrrolidone 7O 71, vinyl acetate 30 /t, molecular weight 35,000 45,000) 2.0 g Ethyl alcohol, 96 titer cc 45 Triethanolamine, q.s.p. pH 7 Water, q.s.p. 100 cc
• This hair-setting lotion when applied to hair dyed golden blond, imparts thereto a luminous and aesthetic 5O pearl glint.
• a gel is obtained which, applied to brown hair at ambient temperature for 15 minutes, imparts to the hair, after rinsing, a dark auburn brown shade.
• This hair-setting lotion when applied to bleached hair, imparts thereto a very luminous light pink blond shade.
• EXAMPLE 40 The following hair-setting lotion is prepared:
• Example 22 Dye of Example 22 i 0.010 g Vinyl pyrrolidone-vinyl acetate copolymer (vinyl pyrrolidone 70 7, vinyl acetate 30 molecular weight 35,000 45.000) 2.0 g Ethyl alcohol, 96 titer 50 cc Triethanolamine. q.s.p. pH 7 N-[(4'-amino 2-methoxy 3'.5-dintethyl) phenyl] 2.5-dimethyl benzoquinoneimine 0.010 g Water. q.s.p 100 cc This hair-setting lotion, when applied to light blond hair, imparts thereto a pearl ash shade.
• Example 23 Dye of Example 23 0.007 g N-(4'-amino 2-methoxy 3,5'-dimethyl) phenyl 2,5-dimethyl benzoquinoneimine 0.003 g N-(4'-hydroxy)phenyl 2.6-dimethyl benzoquinoneimine 0.003 g Vinyl pyrrolidone-vinyl acetate copolymer (vinyl pyrrolidone 60 /1. vinyl acetate 40 7:, molecular weight 45,000 60.000) 2.0 g Ethyl alcohol. 96 titer 50 cc Triethanolamine. q.s.p. pH 6 Water. q.s.p. 100 cc This hair-setting lotion when applied to hair dyed light blond, imparts thereto ash pearl glints.
• Dye of Example 22 0.0l0 g Nitroparaphenylenediamine 0.010 g Vinyl pyrrolidone-vinyl acetate copolymer (vinyl pyrrolidone 4 60 71, vinyl acetate 4O 7:, molecular weight Ethyl alcohol. 96 titer 60 cc Triethanolamine, q.s.p. pH 9 Water. q.s.p.
• This hair-setting lotion when applied to hair dyed light brown, imparts thereto golden copper glints.
• Crotonic acid-vinyl acetate copolymer Crotonic acid l0 /t. vinyl acetate 7:.
• Rg- X and l I RN where R is hydrogen or lower alkyl having 1-4 carbon atoms; or C(R)(R")-, where R each independently have the meaning above;
• R is hydrogen or lower alkyl having l-4 carbon atoms, or R; and R when taken together with the carbon atoms to which they are attached form a benzene ring, a halogen-substituted benzene ring, a benzene ring substituted with lower alkyl having l-4 carbon atoms, a benzene ring substituted with lower alkoxy having l-4 carbon atoms, or a nitrosubstituted benzene ring; and B is a member selected from the group consisting of where R and R, together with the ears mafia nitrogen atoms to which they are attached, form a morpholine group and R is hydrogen and R is hydrogen or lower alkyl having l-4 carbon atoms, or R and R together with the carbon and nitrogen atoms to which and they are attached, form a morpholine group, and E is hydrogen and R is hydrogen, lower alkyl having 14 carbon atoms and alkanoyl having 2 to 5 carbon
• X is a halide, fluorborate, perchlorate, sulfate, di-

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Citations (5)

• 1972
  • 1972-06-02 CH CH823472A patent/CH560539A5/xx not_active IP Right Cessation
  • 1972-06-02 CA CA143,789A patent/CA1021324A/fr not_active Expired
  • 1972-06-02 FR FR7219934A patent/FR2140205B1/fr not_active Expired
  • 1972-06-02 BE BE784359A patent/BE784359A/xx unknown
  • 1972-06-03 IT IT68758/72A patent/IT982408B/it active
  • 1972-06-05 US US259689A patent/US3869454A/en not_active Expired - Lifetime
  • 1972-06-05 DE DE19722227214 patent/DE2227214A1/de not_active Withdrawn
  • 1972-06-05 GB GB2620472A patent/GB1360562A/en not_active Expired

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