Patents Assigned to Toms River Chemical Corporation
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Patent number: 4405785Abstract: Useful vat dyestuffs can be prepared by reacting a mixture of aminoanthraquinones containing 65-80% 1-aminoanthraquinone and 20-35% of a mixture containing 2-aminoanthraquinone and 1,5- and 1,8-diaminoanthraquinones with, for example, a halogenated benzanthrone or anthraquinone. The mixture of aminoanthraquinones can be obtained by nitrating anthraquinone in sulfuric acid and thereafter reducing the resulting nitroanthraquinones.Type: GrantFiled: October 15, 1980Date of Patent: September 20, 1983Assignee: Toms River Chemical CorporationInventors: Joseph W. Fitzpatrick, Harold N. Schmidt
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Patent number: 4377519Abstract: Water-soluble dyes of the structure ##STR1## wherein D is a benzene group or a naphthylene group,A is H, Cl, Br, lower alkyl, or lower alkoxyB is H, lower alkyl, or lower alkoxy,B.sub.1 is lower alkyl or lower alkoxy,R is H, Cl, Br, lower alkyl, or lower alkoxy, andM and M.sub.1 are H, Na, K, NH.sub.4, or Li.The dyes have good affinity for natural and synthetic polyamide fibers, including wool, silk and nylon, which they dye from neutral or weakly acid dye baths in strong navy blue shades with good fastness properties. These dyes are also valuable in combination with certain orange dyes to produce black shades on polyamide fibers that possess good fastness properties.Type: GrantFiled: September 11, 1980Date of Patent: March 22, 1983Assignee: Toms River Chemical CorporationInventor: Hans A. Stingl
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Patent number: 4283556Abstract: A process for the manufacture of a substantially isomerically pure acylanilide of the structure ##STR1## where R is hydrogen, lower alkyl, hydroxy-lower alkyl or lower alkoxy-lower alkyl;R.sub.1 is lower alkyl, phenyl, lower alkylphenyl, lower alkoxy, lower alkoxyphenyl, chlorophenyl, nitrophenyl, dichlorophenyl, chloro-lower alkyl, cyano-lower alkyl, lower alkyl amino, sulfamoylphenyl, carbamoylphenyl or lower alkoxy-lower alkyl; andX is --CO-- or --SO.sub.2 --;comprising the step of treating an alcohol solution of a diamino compound of the structure ##STR2## with an acylating agent, to give an alcohol solution of the acylanilide, wherein substantially equivalent amounts of the acylating agent and the diamino compound are used and wherein the treatment is carried out by the slow, drop-wise addition of the acylating agent at a temperature in the range of about 0.degree. to 5.degree. C.Type: GrantFiled: February 7, 1980Date of Patent: August 11, 1981Assignee: Toms River Chemical CorporationInventor: Philip C. Lang
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Patent number: 4255342Abstract: A method of synthesizing phenoxyanthraquinones in the absence of excess phenol, water-miscible alcohols or polar aprotic solvents. Phenoxyanthraquinones are synthesized in high yield and purity by treatment of the corresponding chloro- or nitroanthraquinone with an equivalent of alkali metal phenoxide, particularly potassium phenoxide in a liquid aromatic solvent which is a chloro-substituted benzene, a lower alkyl-substituted benzene, or a loweralkyl-chloro-substituted benzene. The use of the inventive solvents results in high yields of readily isolable, substantially pure product. The used solvent is readily recoverable without the pollution potential of excess phenol or difficultly recoverable water-miscible solvents.Type: GrantFiled: April 2, 1979Date of Patent: March 10, 1981Assignee: Toms River Chemical CorporationInventor: Arthur D. Olin
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Patent number: 4199318Abstract: Compounds of the formula ##STR1## in which A.sub.1 and A.sub.2 may be hydrogen, alkyl, alkoxy, hydroxy, halo, trifluoromethyl, alkoxyalkoxy, hydroxyalkyl, hydroxyalkoxy, alkoxyalkyl, sulfamoyl, N-alkylsulfamoyl, carboxylic acyl or carboxylic acylamino, B.sub.1 and B.sub.2 are each hydrogen, lower alkoxy, lower alkyl, chloro, bromo, trifluoromethyl, alkoxyalkoxy, hydroxyalkyl, hydroxyalkoxy, or alkoxyalkyl, wherein at least one of A.sub.1, A.sub.2, B.sub.1, or B.sub.2 is alkoxy, and D represents a hydroxy or amino naphthyl or a benzylamino substituted phenyl group, are valuable dyestuffs for natural and synthetic polyamide fibers giving substantially complete exhaustion from neutral or acid aqueous dyebaths without further addition of chemical agents.Type: GrantFiled: November 20, 1978Date of Patent: April 22, 1980Assignee: Toms River Chemical CorporationInventor: Hans A. Stingl
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Patent number: 4173565Abstract: Dyes of the formula ##STR1## wherein B and D are each independently 1,4-phenylene or 1,4-naphthylene; M is hydrogen, lithium, sodium, potassium or ammonium;A.sub.1 is hydrogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, trifluoromethyl, nitro, chloro, bromo, cyano, or hydroxy;B.sub.1 and B.sub.2 are each hydrogen, C.sub.1-3 alkoxy, C.sub.1-3 alkyl, chloro or bromo;D.sub.1 is hydrogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, or chloro;D.sub.2 is hydrogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, chloro, bromo, fluoro, or acylamino, acyl being C.sub.1-5 alkanoyl, C.sub.1-5 alkylsulfonyl, benzoyl or benzenesulfonyl, each acyl unsubstituted or substituted with 1 to 3 of C.sub.1-2 alkyl, C.sub.1-2 alkoxy, chloro, bromo, cyano, or hydroxy; andR.sub.1 and R.sub.2 are each C.sub.1-6 alkyl, C.sub.1-6 chloro or bromoalkyl, C.sub.2-6 hydroxy- or dihydroxyalkyl, C.sub.2-6 alkoxyalkyl, C.sub.1-6 cyanoalkyl, or phenyl-C.sub.1-2 alkyl (phenyl unsubstituted or substituted with 1 to 3 of C.sub.1-2 alkyl, C.sub.Type: GrantFiled: December 23, 1977Date of Patent: November 6, 1979Assignee: Toms River Chemical CorporationInventor: Hans A. Stingl
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Patent number: 4143035Abstract: Compounds of the formula ##STR1## in which A.sub.1 and A.sub.2 may be hydrogen, alkyl, alkoxy, hydroxy, halo, trifluoromethyl, alkoxyalkoxy, hydroxyalkyl, hydroxyalkoxy, alkoxyalkyl, sulfamoyl, N-alkylsulfamoyl, carboxylic acyl or carboxylic acylamino, B.sub.1 and B.sub.2 are each hydrogen, lower alkoxy, lower alkyl, chloro, bromo, trifluoromethyl, alkoxyalkoxy, hydroxyalkyl, hydroxyalkoxy, or alkoxyalkyl, wherein at least one of A.sub.1, A.sub.2, B.sub.1, or B.sub.2 is alkoxy, and D represents a hydroxy or amino naphthyl or a benzylamino substituted phenyl group, are valuable dyestuffs for natural and synthetic polyamide fibers giving substantially complete exhaustion from neutral or acid aqueous dyebaths without further addition of chemical agents.Type: GrantFiled: June 7, 1976Date of Patent: March 6, 1979Assignee: Toms River Chemical CorporationInventor: Hans A. Stingl
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Patent number: 4110072Abstract: A composition comprising two or more benzensulfonamido anthraquinone dyes, selected from those of the formula: ##STR1## wherein R is methyl, ethyl, hydroxyethyl, .beta.-methoxyethyl or .beta.-ethoxyethyl,R.sub.1 is hydrogen or methyl andR.sub.2 is hydrogen, methyl or methoxy, provided that in at least one of the selected dyes, R.sub.1 and R.sub.2 are both hydrogen. The mixture of dyes gives improved dye strength and brightness of shade and is useful for dyeing linear polyester material, particularly textile material, in shades of red, with excellent leveling and fastness properties.Type: GrantFiled: May 31, 1977Date of Patent: August 29, 1978Assignee: Toms River Chemical CorporationInventors: Joseph W. Fitzpatrick, Arthur D. Olin
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Patent number: 4092103Abstract: Compounds of the formula ##STR1## wherein A is hydrogen, lower alkyl, such as methyl, ethyl, butyl or lower alkoxy, such as methoxy, ethoxy, butoxy, or chlorine; B is hydrogen, lower alkyl such as methyl, ethyl or butyl or lower alkoxy, such as methoxy, ethoxy or butoxy; B.sup.1 is lower alkoxy such as methoxy, ethoxy or butoxy; E.sub.1 is hydrogen, lower alkyl such as methyl, ethyl, butyl or lower alkoxy such as methoxy, ethoxy or butoxy, E.sub.2 is hydrogen, lower alkyl such as methyl or ethyl, lower alkoxy such as methoxy or ethoxy; R is lower alkyl of 1 to 4 carbon atoms, such as methyl, ethyl, propyl or butyl and OR is either ortho or para to the azo linkage; and --SO.sub.3 H is either meta or para to A, provide yellow to scarlet dyeings of very good fastness and dyeing properties and excellent leveling characteristics on natural and synthetic polyamide fibers.Type: GrantFiled: March 26, 1976Date of Patent: May 30, 1978Assignee: Toms River Chemical CorporationInventor: Hans Alfred Stingl
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Patent number: 4058515Abstract: Metallized azo dyes of the formula ##STR1## wherein A is a sulfonyl, sulfonamido or carboxamido group, D is the residue of a phenol or naphthol, E is the residue of acetoacetanilide, a phenyl or naphthyl pyrazolone or the residue of a naphthol and M is a cation. The dyes are suitable for dyeing natural and synthetic polyamides, demonstrating good all-around fastness properties.Type: GrantFiled: May 31, 1974Date of Patent: November 15, 1977Assignee: Toms River Chemical CorporationInventors: Hans Alfred Stingl, John Elliott
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Patent number: 3991043Abstract: A process for the manufacture of water soluble dyestuffs of the formula ##SPC1##WhereinR.sub.1 and R.sub.2 are independently selected from the group consisting of lower alkyl, hydroxy lower alkyl, cyano lower alkyl and phthalimide lower alkyl or R.sub.1 and R.sub.2 taken together with the attached nitrogen are morpholino;R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen, halogen, lower alkyl and lower alkoxy;X.sub.3 is lower alkyl; andA.sup.- is an anionIncluding the step of treating the corresponding non-quaternized benzthiazole-azo compound with a di-lower alkyl sulfate in an alkaline aqueous medium, including the improvement of using a large excess of the di-lower alkyl sulfate. The dyestuffs are obtained in good yield by the inventive process and are valuable blue dyestuffs, particularly useful for coloring acrylic fibers.Type: GrantFiled: November 27, 1974Date of Patent: November 9, 1976Assignee: Toms River Chemical CorporationInventor: Hugo Illy
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Patent number: 3983145Abstract: Alpha-dihydroxyanthraquinones used as intermediates in the synthesis of many dyestuffs, such as the Alizarin Saphirols (e.g. Color Constitution No. 63000, 63005, 63010, 63011, 63315 and 63610) can be replaced on an equimolar basis by alpha-di(lower alkoxy)anthraquinones. The alpha-di(lower alkoxy) anthraquinones can be converted in a single step, by treatment with oleum, to the corresponding alpha-dihydroxyanthraquinone-beta-disulfonic acids in almost quantitative yield. The corresponding diamine is obtained by dinitrating followed by reduction of the nitro groups. The known intermediate, leuco 1,4,5,8-tetrahydroxyanthraquinone (see C.I. No. 62500) can be obtained either by reduction of the diamine or by reduction of the dinitro compound. In one embodiment, the alpha-di(lower alkoxy)anthraquinone is obtained from dinitroanthraquinone by treatment thereof with methanol and KOH.Type: GrantFiled: November 1, 1973Date of Patent: September 28, 1976Assignee: Toms River Chemical CorporationInventors: David L. White, Joseph W. Fitzpatrick