Coloring Agent Patents (Class 162/162)
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Patent number: 4686285Abstract: (i) Metal-free compounds of the formula ##STR1## (ii) tautomers thereof, (iii) 1:1 and 1:2 metal complexes of (i) and (ii),(iv) salts of (i), (ii), and (iii), and(v) mixtures of (i), (ii), (iii), and (iv),wherein the symbols are as defined in the Specification, are useful as dyes for, for example, polymers and copolymers of acrylonitrile, polyesters modified to contain acid groups, polyamides such as wool, leather, cotton, bast fibers such as hemp, flax, sisal jute, coir and straw, regenerated cellulose, glass fibers and paper (those wherein R.sub.o is other than hydrogen) or as intermediates for the synthesis of dyes.Type: GrantFiled: February 8, 1985Date of Patent: August 11, 1987Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4652632Abstract: Naphtholazo benzoylalkylene amines and salts thereof which are useful as dyes for acid-modified fibers, leather and paper, and which are represented by the formula ##STR1## wherein n is 0 or 1,A is an anion,R is C.sub.2 - to C.sub.4 -alkyleneR.sup.1 and R.sup.2 independently of one another are C.sub.1 - to C.sub.4 -alkyl, methoxyethyl, cyclohexyl, and R.sup.1 and R.sup.2 together are ##STR2## and R.sup.3 is methyl, ethyl or hydroxyethyl.Type: GrantFiled: April 1, 1985Date of Patent: March 24, 1987Assignee: BASF AktiengesellschaftInventor: Horst Colberg
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Patent number: 4629630Abstract: A check paper is being described which is protected against falsifications and forgeries. Crushable micro capsules are being embedded in check paper which contain on one hand a leuco ink and on the other hand a color acceptor. The color acceptor can also be stored in the body of the paper without the use of micro capsules. The leuco ink and the color acceptor react together under color development or color changes if the micro capsules burst through imprinting or other local pressure application to the paper surface. Thus, a character written on the paper surface becomes visible within the body of the paper and cannot be forged anymore.Type: GrantFiled: April 30, 1984Date of Patent: December 16, 1986Assignee: GAO Gesellschaft Fuer Automation und Organisation mbHInventor: Ludwig Devrient
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Patent number: 4623397Abstract: Compounds of the formula I ##STR1## in which each R.sub.1, independently, is hydrogen, C.sub.1-8 alkyl, C.sub.2-3 alkyl substituted by one or two substituents selected from the group consisting of halo, hydroxy, cyano, methoxy, ethoxy and (C.sub.1-2 alkoxy)carbonyl or cyclohexyl, and each R.sub.2 and R.sub.3, independently, is hydrogen, chlorine, bromine, methyl, methoxy or ethoxy, their production and use as pigments for the mass pigmentation of, for example, viscose, surface coatings such as oil and water base paints and lacquers and inks, pigment printing, textile coating and pigmenting paper in the mass.Type: GrantFiled: October 10, 1984Date of Patent: November 18, 1986Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4597912Abstract: A compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently of one another are unsubstituted or hydroxy substituted, C.sub.1 -C.sub.4 alkoxy substituted, cyano substituted, C.sub.1 -C.sub.4 alkoxycarbonyl substituted, di-C.sub.1 -C.sub.4 alkylamino substituted, (CH.sub.3)(C.sub.6 H.sub.5 CH.sub.2)NC.sub.2 H.sub.4 substituted, chlorine substituted or bromine substituted C.sub.1 -C.sub.4 -alkyl, cyclohexyl, benzyl, phenylethyl or phenyl, R.sup.1 and R.sup.2 together with the nitrogen are morpholino, pyrrolidino, piperidino or N-methylpiperazino;R.sup.3 is hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy or nitro;R.sup.4 and R.sup.5 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl or benzyl; X is oxygen or imino; A.sup.Type: GrantFiled: May 17, 1985Date of Patent: July 1, 1986Assignee: BASF AktiengesellschaftInventors: Manfred Eisert, Klaus Grychtol
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Patent number: 4579939Abstract: Yellow dyes from substituted 2-aminothiophene and acyclic active methylene coupling components are of particular interest for dyeing polyester fibers. The dyes have the formula: ##STR1## wherein: X is a group such as alkyl, allyloxy, alkoxy, aryl or the like; Y is hydrogen, alkyl, or aryl; Z is alkyl, aryl, alkylsulfonyl, cyano or COX where X is defined above; R is cyano, carbamyl, alkanoyl, aroyl, or the like; R.sub.1 is selected from the R groups and ##STR2## wherein R.sub.2 represents the atoms necessary to complete an azole radial selected from benzothiazole, benzimidazole, benzoxazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, and pyrazole; and wherein the hydrocarbon moieties of each of the above radicals or groups may be substituted with up to three of --OH, alkoxy, hydroxyalkoxy, alkylcarbamyl, or the like.Type: GrantFiled: March 16, 1984Date of Patent: April 1, 1986Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Clarence A. Coates, Jr.
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Patent number: 4562247Abstract: There are described azo compounds of the formula ##STR1## wherein D.sub.1 and D.sub.2 are each the radical of a diazo component, R is C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 alkyl substituted by C.sub.1 -C.sub.4 -alkoxy or halogen or is phenyl or phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 alkoxy, and Y is a basic or cationic group. These azo compounds can be used as dyes for dyeing and printing natural and synthetic, cationically dyeing substrates, particularly textile materials and paper.Type: GrantFiled: May 29, 1984Date of Patent: December 31, 1985Assignee: Ciba Geigy CorporationInventor: Visvanathan Ramanathan
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Patent number: 4558133Abstract: Novel dyestuffs of the general formula ##STR1## wherein R designates a lower alkyl or alkenyl radical andR.sup.1 and R.sup.2 designate lower alkyl or alkenyl radicals which, together with the nitrogen atom to which they are bonded, can form a 5-membered or 6-membered heterocyclic ring,and whereinR, R.sup.1 and R.sup.2 can be substituted by non-ionic radicals, and at least one of the radicals R, R.sup.1 and R.sup.2 is substituted by an aryl radical, directly or via a bridge, orone of the radicals R.sup.1 or R.sup.2 represents an aryl radical, the ring a can be substituted by 1 or 2 methyl or ethyl radicals,the ring b can be substituted by 1 or 2 methyl, ethyl, methoxy or ethoxy radicals or by 1 halogen atom andAn.sup.- represents an anion,are particularly suitable for dyeing paper.Type: GrantFiled: July 21, 1980Date of Patent: December 10, 1985Assignee: Bayer AktiengesellschaftInventor: Hermann Beecken
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Patent number: 4555568Abstract: When diazotizing lower alkyl esters of 3-nitro-4-aminobenzoic acid and coupling them onto 5-(2'-hydroxy-3'-naphthoylamino)-benzimidazolone-(2) which may be substituted in 6'-position by chlorine or bromine, in 1-position by methyl or ethyl and in the benzo-nucleus by chlorine, bromine, methyl, ethyl, methoxy or ethoxy, and such as further illustrated by a representative formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, X is hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, Y is hydrogen, methyl or ethyl, and Z is hydrogen, chlorine or bromine. Colorants are obtained which are especially useful for pigmenting plastics, spinning masses, printing inks, varnishes and paints. The dyeings obtained therewith are fast to light, weathering, solvents and migration, especially fast to overvarnishing and bleeding.Type: GrantFiled: June 23, 1980Date of Patent: November 26, 1985Assignee: Hoechst AktiengesellschaftInventor: Klaus Hunger
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Patent number: 4550158Abstract: Metal-free azo compounds of the formula ##STR1## wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification,R.sub.t is an arylazo group or a group of the formula -Y-Z,whereinY is a direct bond or a bridging radical, andZ is a basic amino or quaternary ammonium group, ##STR2## wherein each of the variables is as defined above or below, X is a direct bond or a bridging radical,x is hydrogen, hydroxy C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino or carboxy,ring B is further unsubstituted or further substituted,d is 0, 1 or 2, andn is 0 or 1,with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups,and 1:1 and 1:2 metal complexes thereof,which metal-free compounds and metal complexes are useful as dyes for leather and paper.Type: GrantFiled: August 18, 1982Date of Patent: October 29, 1985Assignee: Sandoz Ltd.Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
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Patent number: 4543157Abstract: The disclosure relates to process and apparatus for the production of variegated paper, especially including but not limited to paper used in the manufacture of simulated caning material. The process involves the indirect application of aqueous dye solutions to a wet paper web, after formation on the wire and passage of the web through the wet press section, but prior to drying. Multiple jet-like streams of a plurality of dye solutions are directed at the surface of a resilient transfer roller, while being oscillated transversely of the web in an asynchronous manner. Jet-like streams of dye solution apply a relatively wide flow pattern to the surface of the transfer roller, and also cause substantial desirable splattering of the dye solution on the roll surface for subsequent transfer to the wet web, as it passes through a pressure nip formed in part by the transfer roller.Type: GrantFiled: November 14, 1983Date of Patent: September 24, 1985Assignee: James River Pepperell, Inc.Inventors: Harold R. Jones, Karl F. Saila
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Patent number: 4540775Abstract: The compound of the formula, ##STR1## a pigment existing in a yellow (.alpha.) modification and an orange (.beta.) modification, the latter being obtained by treatment of the .alpha. form with boiling organic solvents, is useful for the mass pigmenting of synthetic plastics and resins, free from or containing solvents, such as viscose, cellulose acetate, polyethylene, polystyrene, polyvinyl chloride and synthetic leathers and rubbers, of surface coatings such as paints and lacquers and of inks and for pigment printing, textile coating and pigmenting paper in the mass.Type: GrantFiled: May 11, 1981Date of Patent: September 10, 1985Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4536570Abstract: This invention relates to novel mixtures consisting essentially of benzanilide bridged disazo compounds which are randomly substituted with x (N-substituted sulfonamido) groups, to acid-addition salts of said disazo compounds, useful as direct dyes particularly in the dyeing of cellulose, and to methods of preparation of said mixtures of (N-substituted sulfonamido) substituted disazo compounds.Type: GrantFiled: October 25, 1982Date of Patent: August 20, 1985Assignee: The Hilton-Davis Chemical Co.Inventor: Nathan N. Crounse
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Patent number: 4522429Abstract: Confidential information is printed, typed or otherwise applied to paper with a color having a reflection spectral response or less than about 10% for light with a wave-length below about 600 millimicrons. The color is sufficiently contrasting with the information to enable the information to be read by the human eye when the document is viewed under white light, but the document cannot be successfully photocopied.Type: GrantFiled: November 23, 1982Date of Patent: June 11, 1985Assignee: Nocopi Inc.Inventors: Norman A. Gardner, Michael P. Voticky
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Patent number: 4515599Abstract: A process for dyeing paper which comprises the use of dyes of the formula ##STR1## wherein R is hydrogen, hydroxyl or amino, X is the azoxy or azo group, and n is 1 or 2, and the bonds of the complexing oxygen atom in the .alpha.-position and of the azo group in the .beta.-position at the naphthalene nuclei are mutually interchangeable. Dyeings of good wetfastness and lightfastness are obtained.Type: GrantFiled: September 9, 1983Date of Patent: May 7, 1985Assignee: Ciba Geigy CorporationInventor: Adolf Kaser
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Patent number: 4486348Abstract: Cationic triazinyl dyestuffs of the formula ##STR1## wherein R.sub.11 and R.sub.12 independently of one another are H, Cl, Br, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.3 or C.sub.2 H.sub.5,X is a radical of the formula COCH.sub.3, CN, COOCH.sub.3, COOC.sub.2 H.sub.5, CONH.sub.2 or COC.sub.6 H.sub.5,Y and Z independently of one another are C.sub.2 -C.sub.5 -alkylene,R.sub.1 and R.sub.2 independently of one another are H, Cl, Br, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.3 or C.sub.2 H.sub.5,R.sub.3 and R.sub.4 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sub.5 -R.sub.10 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, .beta.- or .gamma.-hydroxy-C.sub.2 -C.sub.4 -alkyl, phenyl or benzyl, orR.sub.5 and R.sub.6, and/or R.sub.8 and R.sub.9 in each case together with the nitrogen, form a pyrrolidine, morpholine or piperidine ring, orR.sub.5, R.sub.6 and R.sub.7 and/or R.sub.8, R.sub.9 and R.sub.Type: GrantFiled: February 24, 1984Date of Patent: December 4, 1984Assignee: Bayer AktiengesellschaftInventor: Klaus Kunde
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Patent number: 4469555Abstract: Disclosed are novel organic pigments adapted particularly for use as fillers for paper. The organic pigments are finely divided particles obtained by graft copolymerizing an ethylenically unsaturated monomer, such as styrene, onto a water-soluble cationic prepolymer in an aqueous solution and in the presence of a free-radical polymerization initiator.Type: GrantFiled: December 30, 1981Date of Patent: September 4, 1984Assignee: Hercules IncorporatedInventors: William W. Maslanka, Gavin G. Spence
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Patent number: 4468348Abstract: Dyes of the formula ##STR1## and mixtures thereof, in which R signifies a radical of formula (a), (b), (c), (d), (e), (f), (g) or (h) ##STR2## in which R.sub.1 signifies an amino, anilino or toluidino radical, R.sub.2 signifies a hydroxy or amino radical, andeither R.sub.3 signifies hydrogen,or, where R.sub.1 and R.sub.2 signify amino, R.sub.3 signifies hydrogen, nitro, --SO.sub.3 M or C.sub.1-6 alkyl; ##STR3## in which R.sub.4 signifies a hydroxy, amino, anilino or toluidino radical, preferably a hydroxy or amino radical; ##STR4## in which R.sub.5 signifies a hydroxy radical, a C.sub.1-6 alkylsulphonyloxy radical, a phenylsulphonyloxy radical, an amino radical, a C.sub.1-6 alkylsulphonylamino radical or a phenysulphonylamino radical, preferably a hydroxy radical,R.sub.6 signifies a C.sub.1-6 alkyl, C.sub.1-6 alkoxy, acetyl, carboxyl or carbamoyl radical,R.sub.7 signifies hydrogen, an acyl radical or an unsubstituted or substituted C.sub.Type: GrantFiled: February 4, 1980Date of Patent: August 28, 1984Assignee: Sandoz Ltd.Inventor: Heinz Wicki
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Patent number: 4451398Abstract: Dyes of the formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkenyl, R.sup.2 and R.sup.3 independently of one another are hydrogen, C.sub.1 -C.sub.5 -alkyl or C.sub.2 -C.sub.5 -alkenyl, R.sup.4 is C.sub.1 -C.sub.12 -alkyl or hydroxy-C.sub.2 -C.sub.4 -alkyl, X.sup..crclbar. is one equivalent of an anion, mis from 0 to 5 and n is from 0 to 5, with 1.ltoreq.(m+n).ltoreq.5, and F is an (m+n)-valent radical of a monoazo dye, a disazo dye, a polyazo dye, a quinophthalone, a bis-dioxazine, a compound of the 5,6-arylo-2-pyrone series, a naphtholactam dye, a triphenylmethane dye, a xanthene dye, a phthalocyanine, an indigoid, an anthraquinone dye containing one or more phenyl or naphthyl groups, a more highly fused carbonyl-containing dye, a quinacridone, a perylene-3,4,9,10-tetracarboxylic acid diimide, an anthrapyrimidine, a pyrazoloanthrone, a diaminonaphthoquinone, a naphthazarine or a naphthalene-1,4,5,8-tetracarboxylic acid diimide.Type: GrantFiled: February 11, 1981Date of Patent: May 29, 1984Assignee: BASF AktiengesellschaftInventors: Manfred Patsch, Manfred Ruske
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Patent number: 4451530Abstract: Security papers with luminescing authenticity features worked into them or printed on them. The authenticity features used consist of a luminophore and one or more absorbing materials by which the emission and/or the excitation spectrum of the luminophore is changed in detectable fashion. The dyestuff can be present as an admixture to the luminophore, as a coating of a luminophore layer or as a coating on luminophore powder grains. For checking the authenticity of documents the emission spectrum of the luminophore is not used but the change generated by the technology used in the emission or excitation spectra.Type: GrantFiled: October 23, 1981Date of Patent: May 29, 1984Assignee: GAO Gesellschaft fur Automation und Organisation mbH.Inventors: Wittich Kaule, Gerhard Schwenk, Gerhard Stenzel
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Patent number: 4444959Abstract: Water-soluble benzylated polyamidoamines which contain from 0.1 to 0.9 mole of benzyl groups per equivalent of nitrogen, and onto which from 20 to 400 parts by weight of ethyleneimine or propyleneimine have been grafted per 100 parts by weight of polyamidoamine, processes for the preparation of the materials, and the use of the materials as cationic assistants in processes for coloring paper with acid dyes and/or direct dyes in an aqueous medium. The papers obtained show a high color strength, with substantially no two sidedness of the coloration.Type: GrantFiled: February 19, 1982Date of Patent: April 24, 1984Assignee: BASF AktiengesellschaftInventors: Guenter Frey, Werner Streit, Rolf Fikentscher, Hans-Juergen Degen, Wolf Guender
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Patent number: 4421601Abstract: A dyestuff of the formula ##STR1## wherein X.sub.1 denotes amino, cyanamino, acetylamino, guanidino, ureido or hydroxyl;Y.sub.1 and Z.sub.1 denote hydroxyl or amino, with the proviso that at most 2 of the 3 radicals X.sub.1, Y.sub.1 and Z.sub.1 denote hydroxyl;R.sub.1 represents hydrogen, nitro, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitrile, C.sub.1 -C.sub.4 -alkylsulphonyl, trifluoromethyl, phenylsulphonyl, benzylsulphonyl, phenoxy, carbo-C.sub.1 -C.sub.4 -alkoxy, carbophenoxy, carbonamido, C.sub.1 -C.sub.4 -alkylcarbonylamino, benzoylamino, sulphonamido, or carbonamido or sulfonamide mono-substituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, phenyl, or benzyl; andR.sub.2 and R.sub.3 represent hydrogen; chlorine C.sub.1 -C.sub.4 -alkyl, carbo-C.sub.1 -C.sub.4 -alkoxy, carbonamido; carbonamido mono-substituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, phenyl, or benzyl, or C.sub.1 -C.sub.4 -alkoxyand a process for coloring substrates using such dyestuff.Type: GrantFiled: January 3, 1978Date of Patent: December 20, 1983Assignee: Bayer AktiengesellschaftInventors: Gunter Stephan, Karl H. Schundehutte
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Patent number: 4416939Abstract: A heat-sensitive recording paper is disclosed having improved heat-transmission efficiency between a recording element and the heat-sensitive recording paper. The disclosed heat-sensitive recording paper includes a support base paper having an aqueous-sensitive developable layer coated thereon. In the base paper used, the value obtained by dividing Stockigt sizing degree by a square number of meter areal weight is 3.times.10.sup.-3 (S.m.sup.4 /g.sup.2) or more and Bekk smoothness of 90 seconds or more. The aqueous heat-sensitive developable layer coated on the surface of the base support includes a dispersion of particles having a volume average particle size of 8 .mu.m or less, said layer being coated on the surface of the base support to a thickness of 5 to 10 .mu.m.Type: GrantFiled: January 13, 1982Date of Patent: November 22, 1983Assignee: Fuji Photo Film Co., Ltd.Inventors: Akira Igarashi, Sukenori Nakamura
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Patent number: 4413131Abstract: Disclosed are compounds of formula I, ##STR1## in which the R.sub.1 's, independently, are chlorine or bromine, andR.sub.2 is fluorine, chlorine, bromine, methyl, ethyl, ethoxy or tri-fluoromethyl,their production and use as pigments.Type: GrantFiled: July 11, 1977Date of Patent: November 1, 1983Assignee: Sandoz Ltd.Inventor: Dimitrios Karanatsios
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Patent number: 4411669Abstract: Cationic azo dyestuffs of the formula ##STR1## wherein X.sup.(+) denotes an ammonium group, m denotes 0 or 1,R denotes hydrogen, halogen, C.sub.1 - to C.sub.4 -alkyl, C.sub.1 - to C.sub.4 -alkoxy, hydroxyl, amino, sulphonamido and carboxamido, or acylamino which is optionally substituted by halogen or a quaternary group, R.sup.1 denotes hydrogen, C.sub.1 - to C.sub.4 -alkyl, halogen or C.sub.1 - to C.sub.4 -alkoxy,R.sub.2 and R.sub.3 independently of one another denote hydrogen, C.sub.1 - to C.sub.4 -alkyl, C.sub.1 - to C.sub.4 -alkoxy or acylamino, andAn.sup.(-) denotes an anion, andwherein the azo group and hydroxyl group of ring a are located adjacent to one another and further carbocyclic or heterocyclic rings can be fused to ring a, are used for dyeing paper.Type: GrantFiled: February 26, 1982Date of Patent: October 25, 1983Assignee: Bayer AktiengesellschaftInventors: Peter Wild, Horst Nickel
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Patent number: 4394212Abstract: Bleed-fast, dyed cellulosics particularly absorbent papers have been obtained with a particular class of water-soluble, cationic dyes reacted with a water-soluble dialdehyde, preferably glyoxal or glutaraldehyde. An aqueous printing fluid containing the water-soluble cationic dye and the dialdehyde, upon drying, produces a water-resistant dyestuff having improved bleed fastness upon cellulosic fibers.Type: GrantFiled: November 9, 1981Date of Patent: July 19, 1983Assignee: Scott Paper CompanyInventor: Alex Pociluyko
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Patent number: 4383834Abstract: A process for coloring paper with an acid dye and/or direct dye in an aqueous medium in the presence of a water-soluble reaction product of an alkylating agent, possessing an aromatic substituent, with a cationic polyelectrolyte.The process gives papers with high color strength and substantially avoids cylinder twosidedness of the coloration.Type: GrantFiled: February 19, 1982Date of Patent: May 17, 1983Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Degen, Wolf Guender, Guenter Frey, Werner Streit, Rolf Fikentscher, Klaus Wulz
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Patent number: 4381185Abstract: Water-fast printing of paper stock using a colorant solution containing water-soluble polymeric dyes is accomplished by a three step process. Step 1 is selecting a paper stock characterized as containing at least 250 ppm by weight of cation, particularly a polyvalent metal cation (especially Ca.sup.2+ or Al.sup.3+). In step 2, a colorant solution is applied to the paper. This solution is water-based, containing up to 30 wt % of an organic paper-penetrating agent (such as an alkanol), and at least 500 ppm of one or more anionic group-possessing polymeric colorants. In step 3, the solvent is exhausted by either evaporation (which may be aided by the application of heat) or diffusion into the paper stock, or by a combination of both.Type: GrantFiled: June 9, 1981Date of Patent: April 26, 1983Assignee: DynapolInventors: Sally A. Swanson, Ned M. Weinshenker, Robert E. Wingard, Jr., Daniel J. Dawson
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Patent number: 4370443Abstract: Water-soluble triazine-nucleated polymeric quaternary ammonium compounds, which are prepared by the interaction of 2,4,6-trichloro-1,3,5-triazine with one molecular proportion of an aliphatic or cycloaliphatic diamine containing at least one tertiary nitrogen atom capable of being quaternized to effect polymerisation and then with a second molecular equivalent of the same diamine or a different amine, are useful as mordants for water-soluble dyestuffs on cellulosic fibers; as fixing agents for pigments on cellulosic fibers; as softening agents for fibers; and as surface active agents for effecting aqueous dispersions of pigments and of colorless dyestuff precursors for carbonless duplicating systems.Type: GrantFiled: January 11, 1982Date of Patent: January 25, 1983Assignee: Sterling Drug Inc.Inventor: Eugene P. Wesseler
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Patent number: 4348257Abstract: Disclosed are novel organic pigments adapted particularly for use as fillers for paper. The organic pigments are finely divided particles obtained by graft copolymerizing an ethylenically unsaturated monomer, such as styrene, onto a water-soluble cationic prepolymer in an aqueous solution and in the presence of a free-radical polymerization initiator.Type: GrantFiled: June 23, 1980Date of Patent: September 7, 1982Assignee: Hercules IncorporatedInventors: William W. Maslanka, Gavin G. Spence
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Patent number: 4344818Abstract: A method and apparatus especially adapted to produce a ply separable web requiring substantially less energy input for drying. The apparatus comprises a headbox having at least three stock flow channels, the outer channels being adapted to convey conventional aqueous stock solutions, with at least one inner channel adapted to convey airborne fibers. The resulting web, having a significant portion of the fibers in a dry state, requires less energy to dry, and the distinct layers provide shear zones therebetween which permit ply separation upon creping. Different fiber types may be provided in different layers depending upon product attributes desired, and the products may be conventionally dried or may be throughdried. An alternative embodiment requires the mixing of airborne fibers with an aqueous solution adjacent to or within the headbox, producing only surface wetting of the fibers and reduced interfiber bonding.Type: GrantFiled: May 4, 1981Date of Patent: August 17, 1982Assignee: Kimberly-Clark CorporationInventors: David A. Nuttall, Sung H. Hong
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Patent number: 4339238Abstract: The invention relates to formulations which are stable to metal ions and contain a stilbene fluorescent whitening agent which is substituted by sulfo groups, and an acid phosphoric acid ester of an oxyalkylated fatty amine of the formula ##STR1## wherein R is an aliphatic hydrocarbon radical of 8 to 22 carbon atoms, Y.sub.1 and Y.sub.2 are preferably hydrogen, X is the acid radical of phosphoric acid and the sum of n+m is 2 to 30, preferably 4 to 20. The formulations can additionally contain various assistants such as non-ionic or anionic surfactants and/or organic solvents or polar compounds. The formulations are used for whitening natural and synthetic fabrics, e.g. made from polyamide, cellulose and blended fabrics, as well as paper.Type: GrantFiled: January 7, 1981Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: Werner Fringeli, Alain Lauton
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Patent number: 4334015Abstract: A composition capable of forming colored complexes with transition metal salts is provided which comprises an aromatic substituted hydrazone carried in an organic cosolvent vehicle. When employed in the art of carbonless paper the aromatic substituted hydrazone and the transition metal salt complex to form yellow colored images. The invention provides means for producing dark, black, neutral images by the reaction of the aromatic substituted hydrazones and conventional dithiooxamide complexing compounds, both carried in an organic cosolvent vehicle, with transition metal salts.Type: GrantFiled: May 23, 1979Date of Patent: June 8, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventor: Dean R. Yarian
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Patent number: 4333990Abstract: A heat-sensitive recording paper containing in its color-developing layer aluminum hydroxide as fillers and a colorless or pale-colored chromogenic dyestuff and a phenolic substance as chromogenic elements. This heat-sensitive recording paper incorporates high image density and very preferable recording aptitude with less abrasiveness and less residues accumulated even for long time recording.Type: GrantFiled: December 31, 1980Date of Patent: June 8, 1982Assignee: Jujo Patper Co., Ltd.Inventors: Noboru Yamato, Tosimi Satake
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Patent number: 4328069Abstract: A process for the elimination of the fluorescence effect resulting from the treatment of fibrous materials with optical anionic agents is described which consists of treating the fibrous materials with a water soluble salt of a polymer containing the imidazoline ring of formula I ##STR1## wherein X is in the position meta or para with respect to the imidazoline ring and X is ##STR2## or --CO--NH-- The imidazoline-containing compounds prepared by reacting diethylenetriamine or triethylenetetramine with terephthalic or isophthalic acid followed by cyclization are reacted with dicyandiamide. The water soluble salt is an acid addition salt or a quaternary ammonium salt. The new polymers are described.Type: GrantFiled: May 1, 1980Date of Patent: May 4, 1982Assignee: Apital Produzioni Industriall S.p.A.Inventor: Giuseppe Raspanti
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Patent number: 4323362Abstract: Compounds of the general formulaA.sup.1 .dbd.CH--B--CH.dbd.A.sup.2where A.sup.1 and A.sup.2 are the radical of a quaternized methylene-active compound and B is a bridge member.The compounds according to the invention are very suitable for coloring ligneous and lignin-free paper stock.Type: GrantFiled: January 14, 1981Date of Patent: April 6, 1982Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Degen, Klaus Grychtol
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Patent number: 4314001Abstract: Water-soluble triazine-nucleated polymeric quaternary ammonium compounds, which are prepared by the interaction of 2,4,6-trichloro-1,3,5-triazine with one molecular proportion of an aliphatic or cycloaliphatic diamine containing at least one tertiary nitrogen atom capable of being quaternized to effect polymerization and then with a second molecular equivalent of the same diamine or a different amine, are useful as mordants for water-soluble dyestuffs on cellulosic fibers; as fixing agents for pigments on cellulosic fibers; as softening agents for fibers; and as surface active agents for effecting aqueous dispersions of pigments and of colorless dyestuff precursors for carbonless duplicating systems.Type: GrantFiled: March 3, 1980Date of Patent: February 2, 1982Assignee: Sterling Drug Inc.Inventor: Eugene P. Wesseler
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Patent number: 4310591Abstract: A security paper is provided in which identifying material is contained as an intercalary layer within the thickness of a bonded, nonwoven, polyethylene-film-fibril sheet having an opacity of at least 70% and a delamination resistance of at least 60 grams per centimeter. A process for making such paper includes forming an assembly of two unbonded, lightly consolidated, nonwoven, polyethylene film-fibril sheets containing identifying material between them, compressing the assembly in an unheated nip at 17 to 85 kilograms per centimeter of assembly width and then self-bonding the compressed assembly while under restraint by contact with a heated drum. Such security paper is useful for bank notes, stock certificates, paper currency and the like.Type: GrantFiled: August 28, 1980Date of Patent: January 12, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventors: Chi C. Lee, Richard E. Ludwig
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Patent number: 4287122Abstract: Valuable pigments are obtained by diazotizing 1-aminobenzene-2-(carboxylic acid methyl or ethyl ester)-5-(2',3'-dichloro-anilide) and coupling it onto 1-(2'-hydroxy-3'-naphthoylamino)-4-acetamino-benzene. The resulting pigments are then subjected to a thermal aftertreatment. These pigments show a high tinctorial strength, a pure shade, a high fastness to migration, especially to overlacquering, to light and weathering and a high heat stability.Type: GrantFiled: February 25, 1977Date of Patent: September 1, 1981Assignee: Hoechst AktiengesellschaftInventors: Klaus Hunger, Ernst Klappert, Konrad Lohe
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Patent number: 4285861Abstract: This invention relates to new compounds having the structure: ##STR1## wherein M is H, Na, K, Li, N(R).sub.3 H and R is H, lower alkyl or lower hydroxy alkyl and R.sub.1 is oxygen, sulfur, imino, lower alkylimino, cyanoimino and carbamoylimino moieties. The new compounds are useful as fluorescent greenish-yellow dyes for paper.Type: GrantFiled: August 17, 1979Date of Patent: August 25, 1981Assignee: Crompton & Knowles CorporationInventors: David A. Brode, Howard L. Smith
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Patent number: 4282060Abstract: Disclosed are novel organic pigments adapted particularly for use as fillers for paper. The organic pigments are finely divided particles obtained by graft copolymerizing an ethylenically unsaturated monomer, such as styrene, onto a water-soluble cationic prepolymer in an aqueous solution and in the presence of a free-radical polymerization initiator.Type: GrantFiled: August 29, 1979Date of Patent: August 4, 1981Assignee: Hercules IncorporatedInventors: William W. Maslanka, Gavin G. Spence
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Patent number: 4282000Abstract: Aqueous solutions of copper phthalocyanine-sulphonic acid salts of the formula ##STR1## in which Cu--Pc a copper phthalocyanine radical,m a number from 1.8 to 3.0,q a number from 1.0 to 2.0, with the proviso that the sum m+q is a number from 2.8 to 4.0, andM.sup..sym. a mixture of A.sub.n.sup..sym. and an ammonium ion of the formula ##STR2## wherein A.sup..sym. represents an alkali metal ion or NH.sub.4 ion,n represents a number from 0.8 to 2.0,m has the meaning indicated above,R.sub.1 and R.sub.2 designate hydrogen, C.sub.1 --C.sub.4 --alkyl or a radical --(CH.sub.2 --CH.sub.2 --O).sub.p --H andR.sub.3 designates the radical --(CH.sub.2 --CH.sub.2 --O).sub.p --H,whereinp is 1, 2, 3, 4, 5 or 6,process for the preparation of these solutions and their use for dyeing paper.Type: GrantFiled: January 25, 1980Date of Patent: August 4, 1981Assignee: Bayer AktiengesellschaftInventors: Manfred Groll, Friedhelm Muller
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Patent number: 4267319Abstract: Colored polymeric compounds of the general formula ##STR1## where A is the radical of a quaternized, methylene-active compound, R is unsubstituted or substituted alkyl, cycloalkyl or phenyl, R.sup.1 is hydrogen, chlorine, bromine, hydroxyl, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, T is alkylene which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 -alkoxy or hydroxyl, or is a radical of the formula ##STR2## M.sup..crclbar. is an anion and n is a number >1. The compounds according to the invention are particularly suitable for coloring paper stock.Type: GrantFiled: November 30, 1979Date of Patent: May 12, 1981Assignee: BASF AktiengesellschaftInventor: Hans-Juergen Degen
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Patent number: 4258182Abstract: Styryl dyestuffs of the formula ##STR1## wherein Q.sym. represents a grouping containing a quaternary nitrogen atom and A represents a bridge member,at least one of the radicals R and R.sub.1 denotes a carbocyclic or heterocyclic 5-membered or 6-membered ring optionally bonded via a linking member to the nitrogen atom, or, with the o-position of ring a, forms a heterocyclic structure of this type, and the second radical can also represent alkyl or alkenyl, orR and R.sub.1 together form a 5-membered or 6-membered ring, andA.crclbar. represents an anion,are suitable for dyeing, enscribing and printing paper and for dyeing and printing synthetic fibres, especially made of polyacrylonitrile, acid-modified polyesters or polyamides.Type: GrantFiled: March 30, 1978Date of Patent: March 24, 1981Assignee: Bayer AktiengesellschaftInventor: Hermann Beecken
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Patent number: 4252604Abstract: Bis-(triazinylamino)-stilbenesulphonic acids ##STR1## wherein X is optionally substituted NH.sub.2 ##STR2## Y is a radical of formula Z is --COOR.sub.4, --CO--C.sub.m H.sub.2m+1, --CN or ##STR3## R.sub.1 is H, halogen, alkyl or alkoxy, R.sub.2 is H or alkyl,R.sub.3 is H, optionally substituted alkyl, cycloalkyl or phenyl or ##STR4## R.sub.4 is optionally substituted alkyl, R.sub.3 and R.sub.6 are H, alkyl, hydroxyalkyl or form together with N a heterocyclem is a whole number from 1 to 5 andn is 1 or 2,are optical brighteners suitable for cellulosic fibres, polyamide and polyurethane fibres and paper.Type: GrantFiled: August 30, 1977Date of Patent: February 24, 1981Assignee: Sandoz Ltd.Inventors: Fritz Fleck, Hans R. Schmid
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Patent number: 4247318Abstract: A security paper is provided in which identifying material is contained in a plane within the thickness of a bonded, nonwoven polyethylene film-fibril sheet having an opacity of at least 70% and a determination resistance of at least 60 grams per centimeter. A process for making such paper includes forming an assembly of two unbonded, lightly consolidated, nonwoven, polyethylene film-fibril sheets containing identifying material between them, compressing the assembly in an unheated nip at 17 to 85 kilograms per centimeter of assembly width and then self-bonding the compressed assembly while under restraint by contact with a heated drum. Such security paper is useful for bank notes, stock certificates, paper currency and the like.Type: GrantFiled: January 30, 1979Date of Patent: January 27, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventors: Chi C. Lee, Richard E. Ludwig
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Patent number: 4245689Abstract: An improved dimensionally stable backing web is disclosed, especially for resilient flooring product and linoleum, comprising cellulosic fiber, a binder, antioxidant, fungicide and glass fiber, as well as optionally dyes or pigments, surfactants and vulcanizing agents. Also optionally present are calcium silicate mineral fiber or synthetic fiber, such as polyolefin, polyester, nylon, acrylic or modacrylic fiber, a cellulose acetate or mixtures thereof. The binder can be a natural rubber or synthetic rubber latex or mixtures thereof. The synthetic rubber latex is preferably selected from the following: styrene-butadiene; carboxylated styrene-butadiene, polyacrylic ester, polyvinyl acetate; polyisobutylene, a copolymer formed from vinyl acetate monomers and acrylic acid; polychloroprene, acrylonitrile-butadiene or carboxylated acrylonitrile-butadiene; polyurethane; a copolymer of ethylene and vinyl acetate; or other elastomeric copolymers.Type: GrantFiled: May 2, 1978Date of Patent: January 20, 1981Assignee: Georgia Bonded Fibers, Inc.Inventors: Henry P. Grard, Daniel LaVietes, Edmond M. Mergelsberg
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Patent number: 4238283Abstract: Humic acid-dyed paper suitable for use as wrappers for smoking articles is post treated with magnesium sulfate to fix or render the humic acid insoluble. Paper treated in this manner provides a product of acceptable brown color. Smoking articles wrapped in the treated paper evolve a reduced amount of carbon monoxide on smoking under normal conditions in comparison to currently available brown papers stained with humic acid.Type: GrantFiled: June 4, 1979Date of Patent: December 9, 1980Assignee: Philip Morris IncorporatedInventors: Randall K. Greene, Willard A. Geiszler, Jr.
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Patent number: 4212763Abstract: Bis-triazinylaminostilbene compounds of the formula ##STR1## in which R.sub.1 is alkyl, alkenyl, cyclohexyl or phenylalkyl, R.sub.2 is hydrogen, alkyl, cyclohexyl, benzyl, alkyl which is substituted by hydroxyl, cyano, sulpho or carbamoyl, alkoxyalkyl or hydroxyalkoxyalkyl or alkoxyalkoxyalkyl or mono- or di-alkylaminoalkyl, and R.sub.3 is hydrogen, alkyl, alkyl which is substituted by hydroxyl, cyano or sulpho, or alkoxyalkyl or hydroxyalkoxyalkyl or R.sub.2 and R.sub.3 together with the nitrogen atom to which they are bonded are a morpholine ring or a pyrrolidine, piperidine, hexamethyleneimine or piperazine ring which is unsubstituted or substituted by 1 or 2 alkyl groups, and M is hydrogen or an alkali metal, ammonium or amine ion, and, if R.sub.2 or R.sub.3 is hydroxyalkyl, R.sub.1 is methyl, cyclohexyl or alkenyl only, and their use as fluorescent brightening agents for organic material of high molecular weight are disclosed.Type: GrantFiled: June 26, 1978Date of Patent: July 15, 1980Assignee: Ciba-Geigy CorporationInventor: Werner Fringeli
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Patent number: RE31412Abstract: A heat or pressure sensitive copying paper is provided containing a fluoran compound as a color former, said color being developed in said heat or pressure sensitive copying paper through the application of heat or pressure, said fluoran compound being of the formula ##STR1## wherein R.sub.1 is halogen; R.sub.2 is hydrogen or methyl; R.sub.3 is hydrogen, methyl or ethyl; each of R.sub.4 is independently halogen or methyl; R.sub.5 is methyl or ethyl; and n is 0 or an integer from 1 to 4.Type: GrantFiled: May 27, 1980Date of Patent: October 11, 1983Assignee: Yamamoto Kagaku Gosei Kabushiki KaishaInventors: Yoshihiro Hatano, Kenji Yamamoto