Patents by Inventor Herbert Klier
Herbert Klier has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 8562694Abstract: Reactive dyes of the formula (1) wherein B is an aliphatic bridging member, G is a sulfo naphthalene group or a sulfo benzene group of the formula (2a) or a pyridone radical of the formula (2b), R1, R2, R3 and R4 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, (R5)h denotes h identical or different substituents selected from the group sulfo, C1-C4alkyl and C1-C4alkoxy, R6 is hydrogen, sulfo, halogen, carboxy, C1-C4alkyl, C1-C4alkoxy or a fiber-reactive group Z1 of the formula —SO2—Y (3a), —NH—CO—(CH2)1—SO2—Y (3b), —CONH—(CH2)m—SO2—Y (3c), —NH—CO—CH(Hal)-CH2-Hal (3d) or —NH—CO—C(Hal)=CH2 (3e), R7 is amino, C1-C4alkyl or a fiber-reactive group Z2 of the formula —NH—(CH2)n—SO2—Y (3a), (R8)j denotes j identical or different substituents selected from the group sulfo, C2-C4alkanoylamino, ureido, C1-C4alkyl and C1-C4alkoxy, R9 is hydrogen, C1-C4alkyl or C1-C4alkoxy, R10 is hydrogen or C1-C4alkyl, R11 is hydrogen, cyano, carbamoyl or sulfomethyl, and R12 is hydrogen, C1-C4alType: GrantFiled: June 30, 2010Date of Patent: October 22, 2013Assignee: Huntsman International LLCInventors: Athanassios Tzikas, Herbert Klier, Georg Roentgen
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Publication number: 20120117737Abstract: Reactive dyes of the formula (1) wherein B is an aliphatic bridging member, G is a sulfo naphthalene group or a sulfo benzene group of the formula (2a) or a pyridone radical of the formula (2b), R1, R2, R3 and R4 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, (R5)h denotes h identical or different substituents selected from the group sulfo, C1-C4alkyl and C1-C4alkoxy, R6 is hydrogen, sulfo, halogen, carboxy, C1-C4alkyl, C1-C4alkoxy or a fibre-reactive group Z1 of the formula —SO2—Y (3a), —NH—CO—(CH2)l—SO2—Y (3b), —CONH—(CH2)m—SO2—Y (3c), —NH—CO—CH(Hal)-CH2-Hal (3d) or —NH—CO—C(Hal)=CH2 (3e), R7 is amino, C1-C4alkyl or a fibre-reactive group Z2 of the formula —NH—(CH2)nSO2—Y (3a), (R8)j denotes j identical or different substituents selected from the group sulfo, C2-C4alkanoylamino, ureido, C1-C4alkyl and C1-C4alkoxy, R9 is hydrogen, C1-C4alkyl or C1-C4alkoxy, R10 is hydrogen or C1-C4alkyl, R11 is hydrogen, cyano, carbamoyl or sulfomethyl, and R12 is hydrogen, C1-C4alkType: ApplicationFiled: June 30, 2010Publication date: May 17, 2012Applicant: Huntsman Advanced Materials (Switzerland) GNBHInventors: Athanassios Tzikas, Herbert Klier, Georg Roentgen
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Patent number: 7553340Abstract: Reactive dyes of formula (1) wherein R1 is hydrogen or unsubstituted or substituted C1-C4alkyl, R2 is hydrogen; C1-C4alkyl; C1-C4alkoxy unsubstituted or substituted by sulfato, hydroxy or by C1-C4alkoxy; halogen; carboxy or sulfo, R3 is hydrogen; C1-C4alkyl; C1-C4alkoxy unsubstituted or substituted by sulfato, hydroxy or by C1-C4alkoxy; halogen; nitro; C2-C4alkanoylamino; ureido; carboxy or sulfo, (R4)k denotes k identical or different substituents selected from the group halogen, C1-C4-alkyl, C1-C4alkoxy, carboxy and sulfo, X is halogen and V is a radical of formula (2a), 2(b) wherein R5 is unsubstituted or substituted C1-C4alkyl, (R6)I denotes I identical or different substituents from the group C1-C4alkyl, C1-C4alkoxy and sulfo, and I is the number 0, 1 or 2, Y is vinyl or a —CH2—CH2—U radical and U is a group that is removable under alkaline conditions, Q is a —CH(HaI)-CH2-HaI or —C(HaI)=CH2 group, Hal is halogen and k is the number 0, 1 , 2 or 3, are suitable especially for dyeing cotton and yield dyeingType: GrantFiled: November 2, 2005Date of Patent: June 30, 2009Assignee: Huntsman International, LLCInventors: Athanassios Tzikas, Georg Roentgen, Herbert Klier
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Publication number: 20070294842Abstract: Reactive dyes of formula (1) wherein R1 is hydrogen or unsubstituted or substituted C1-C4alkyl, R2 is hydrogen; C1-C4alkyl; C1-C4alkoxy unsubstituted or substituted by sulfato, hydroxy or by C1-C4alkoxy; halogen; carboxy or sulfo, R3 is hydrogen; C1-C4alkyl; C1-C4alkoxy unsubstituted or substituted by sulfato, hydroxy or by C1-C4alkoxy; halogen; nitro; C2-C4alkanoylamino; ureido; carboxy or sulfo, (R4)k denotes k identical or different substituents selected from the group halogen, C1-C4-alkyl, C1-C4alkoxy, carboxy and sulfo, X is halogen and V is a radical of formula (2a), 2(b) wherein R5 is unsubstituted or substituted C1-C4alkyl, (R6)l denotes I identical or different substituents from the group C1-C4alkyl, C1-C4alkoxy and sulfo, and I is the number O, 1 or 2, Y is vinyl or a —CH2—CH2—U radical and U is a group that is removable under alkaline conditions, Q is a —CH(Hal)-CH2-Hal or —C(Hal)?CH2 group, Hal is halogen and k is the number O, 1 , 2 or 3, are suitable especially for dyeing cotton and yield dyeingType: ApplicationFiled: November 2, 2005Publication date: December 27, 2007Inventors: Athanassios Tzikas, Georg Roentgen, Herbert Klier
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Publication number: 20060191082Abstract: Dye mixtures comprising a reactive dye having at least one structural unit of formula (1) together with a reactive dye of formula (2), wherein (Q1)0-3 and (Q2)0-3 each independently of the other denote from 0 to 3 identical or different substituents selected from the group halogen, C1-C4alkyl, C1-C4alkoxy, carboxy and sulfo, Z1 and Z2 are each independently of the other a fibre-reactive radical, at least one fibre-reactive radical being contained in the dye of formula (1) and the dye of formula (2) containing at least one fibre-reactive radical Z1 or Z2, are suitable for dyeing cellulosic or nitrogen-containing fibre materials.Type: ApplicationFiled: January 27, 2004Publication date: August 31, 2006Inventors: Athanassios Tzikas, Georg Roentgen, Herbert Klier
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Patent number: 6953845Abstract: Reactive dyes of formula wherein A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, R1, R2 and R3 are each hydrogen or unsubstituted or substituted C1-C4alkyl, X1 and X2 are halogen, B is an organic bridging member, T is a reactive radical as defined herein and V1 and V2 are each independently of the other N, C—H, C—Cl or C—F, give prints that are distinguished by brilliant color shades and good all-round properties.Type: GrantFiled: July 14, 2003Date of Patent: October 11, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Hans Reichert, Herbert Klier
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Publication number: 20040055098Abstract: Reactive dyes of formula 1Type: ApplicationFiled: July 14, 2003Publication date: March 25, 2004Inventors: Athanassios Tzikas, Hans Reichert, Herbert Klier
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Patent number: 6630005Abstract: Dye mixtures, which comprise at least one dye of formula (1) together with at least one dye of formula (2), wherein R1, R2, R4 and R5 are each independently of one another hydrogen or unsubstituted or substituted C1-C4alkyl, (R3)0-2 is 0 to 2 identical or different substituents selected from the group consisting of C2-C4halogen alkanoylamino, C1-C4alkyl or C1-C4alkoxy, A1 and A2 are each independently of the other an unsubstituted or substituted phenylene radical or a C1-C8alkylene radical which may be interrupted by oxygen, D is a radical of formula (3) or (4) wherein is (R6)0-2 0 to 2 identical or different substituents selected from the group consisting of halogen, C2-C4alkanoylamino, C1-C4alkyl and C1-C4alkoxy, X1 and X2 are halogen, and Y1 and Y2 are each independently of the other a fiber-reactive radical of formula: —SO2—Z (5a): —CONH—(CH2)m—SO2—Z (5b); —NH—CO—CH(Hal)—CH2—Hal (5c).Type: GrantFiled: May 3, 2001Date of Patent: October 7, 2003Assignee: Giba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Urs Lehmann, Herbert Klier
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Patent number: 6623533Abstract: A method of printing cellulosic fiber materials in which the fiber material is brought into contact with reactive dyes of formula: wherein A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, R1, R2 and R3 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, X1 and X2 are halogen, B is an organic bridging member, T is a reactive radical of formula: R4 is hydrogen, C1-C4alkyl unsubstituted or substituted by hydroxy, sulfo, sulfato, carboxy or by cyano, or a radical wherein R5 is as defined hereinbelow, R5 is hydrogen, hydroxy, sulfo, sulfato, carboxy, cyano, halogen, C1-C4alkoxycarbonyl, C1-C4alkanoyloxy, carbamoyl or a group —SO2—Y, R6 is hydrogen or C1-C4alkyl, alk and alk1 are each independently of the other linear or branched C1-C6alkylene, arylene is an unsubstituted or sulfo-, carboxy-, hydroxy-, C1-C4alkyl-, C1-C4alType: GrantFiled: July 5, 2001Date of Patent: September 23, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Hans Reichert, Herbert Klier
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Patent number: 6537332Abstract: Dyes of formula (1) wherein R1 and R2 are each independently of the other hydrogen or C1-C4alkyl, and D1 and D2 are each independently of the other a radical of formula (2) wherein (R3)0-3 denotes from 0 to 3 identical or different substituents selected from the group halogen, C1-C4alkyl, C1-C4alkoxy, carboxy, nitro and sulfo, and X1 is a radical of formula (3a), (3b), (3c), (3d), (3e) or (3f) —SO2—Z (3a), —NH—CO—(CH2)m—SO2—Z (3b), —CONH—(CH2)n—SO2—Z (3c), —NH—CO—CH(Hal)-CH2-Hal (3d), —NH—CO—C(Hal)=CH2 (3e) or wherein Y is halogen, T independently thereof has a meaning given for Y or is a non-fiber-reactive substituent or is a fiber-reactive radical of formula (4a), (4b), (4c), (4d) or (4e) —NH—(CH2)2-3—SO2—Z (4a), —NH—(CH2)Type: GrantFiled: January 24, 2001Date of Patent: March 25, 2003Assignee: Ciba Speciality Chemicals CorporationInventors: Athanassios Tzikas, Herbert Klier
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Patent number: 6392021Abstract: Reactive dyes of formula (1) wherein b is the number 1 or 2, A is the radical of formula (2) or (3) D1, D2, R1, R2, X1, Y, l, m and n are as defined in the specification, are especially suitable for dyeing cotton and wool and yield dyeings having good all round properties.Type: GrantFiled: September 24, 2001Date of Patent: May 21, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Rolf Deitz, Herbert Klier
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Publication number: 20020032318Abstract: A method of printing cellulosic fiber materials in which the fiber material is brought into contact with reactive dyes of formula 1Type: ApplicationFiled: July 5, 2001Publication date: March 14, 2002Inventors: Athanassios Tzikas, Hans Reichert, Herbert Klier
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Patent number: 6353094Abstract: Dyes of the formula in which Me, R1, X1, A, u and q are as defined in the specification are particularly suitable for dyeing cotton and produce dyeings with good all-round properties.Type: GrantFiled: March 15, 2000Date of Patent: March 5, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Herbert Klier
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Patent number: 6323327Abstract: Reactive dyes of formula (1) wherein b is the number 1 or 2, A is the radical of formula (2) or (3) D1 is a radical off formula or the radical of an azo dye when b is the number 1 or the radical of an aromatic tetraazo component when b is the number 2, D2 is the radical of a diazo component, of the benzene or naphthalene series, R1 and R2 are each independently of the other hydrogen or C1-C4alkyl, (R3)0-2 denotes from 0 to 2 substituents selected from the group C1-C4alkyl, C1-C4alkoxy, halogen and sulfo, X1 is fluorine or chlorine, Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, l is the number 2, 3, 4, 5 or 6, and m and n are each independently of the other the number 0 or 1, wherein when A is a radical of formula (3) and D1 is the radical of an azo dye, at least one of the radicals D1 and D2 contains a fibre-reactive radical of formula (2) with the proviso that A is a radical of fType: GrantFiled: November 2, 2000Date of Patent: November 27, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Rolf Deitz, Herbert Klier
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Patent number: 5984978Abstract: There are described reactive dyes of formula ##STR1## wherein the variables are as defined in the claims. The reactive dyes of formula (1) are suitable especially for dyeing or printing cellulosic fiber materials.Type: GrantFiled: February 6, 1998Date of Patent: November 16, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Herbert Klier, Athanassios Tzikas
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Patent number: 5964900Abstract: A process for dyeing or printing cellulosic fiber materials, which comprises using at least one reactive dye of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, halogen, sulfo, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy,R.sub.5 and R.sub.6 are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkanoylamino, ureido, or C.sub.1 -C.sub.4 alkoxy which is unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfato or C.sub.1 -C.sub.4 alkoxy,Z.sub.1 and Z.sub.2 are each independently of the other vinyl or the radical --CH.sub.2 --CH.sub.2 --U, andU is a leaving group.Type: GrantFiled: June 17, 1998Date of Patent: October 12, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Edmond Ruhlmann, Athanassios Tzikas, Herbert Klier
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Patent number: 5936072Abstract: A description is given of reactive dyes of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, sulfo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen,X is fluoro or chloro, andY is a --CHT--CH.sub.2 T or --CT.dbd.CH.sub.2 group, and T is bromo or chloro. The reactive dyes of formula (1) are particularly suitable for dyeing or printing cellulosic fiber materials.Type: GrantFiled: March 12, 1998Date of Patent: August 10, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Herbert Klier
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Patent number: 5837827Abstract: Compounds of the formula ##STR1## in which the variables have the meaning given in the claims, which are suitable as fibre-reactive dyes for dyeing or printing widely varying fibre materials are described.Type: GrantFiled: November 12, 1996Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Hans Reichert, Herbert Klier
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Patent number: 5684138Abstract: Reactive dyes of the formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl,B is an aliphatic bridge member,Y.sub.1 and Y.sub.2 independently of one another are halogen or carboxypyridinium,A.sub.1 is the radical of an anthraquinone, phthalocyanine, dioxazine, formazan or disazo dye or a radical of the formulae (2a) to (2h) defined in claim 1 andA.sub.2 is as defined above for A.sub.1 or is a radical of the formulae (2i) to (2m),where A.sub.1 and A.sub.2 have different meanings to one another, are particularly suitable for dyeing or printing fibre materials containing hydroxyl groups or containing nitrogen. Dyeings having good fastness properties coupled with a high tinctorial yield are obtained.Type: GrantFiled: May 29, 1996Date of Patent: November 4, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Herbert Klier, Bernhard Muller, Edmond Ruhlmann, Athanassios Tzikas
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Patent number: 5552532Abstract: Reactive dyes of the formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl,B is an aliphatic bridge member,Y.sub.1 and Y.sub.2 independently of one another are halogen or carboxypyridinium,A.sub.1 is the radical of an anthraquinone, phthalocyanine, dioxazine, formazan or disazo dye or a radical of the formulae (2a) to (2h) defined in claim 1 andA.sub.2 is as defined above for A.sub.1 or is a radical of the formulae (2i) to (2m),where A.sub.1 and A.sub.2 have different meanings to one another, are particularly suitable for dyeing or printing fibre materials containing hydroxyl groups or containing nitrogen. Dyeings having good fastness properties coupled with a high tinctorial yield are obtained.Type: GrantFiled: May 13, 1994Date of Patent: September 3, 1996Assignee: Ciba-Geigy CorporationInventors: Herbert Klier, Bernhard M uller, Edmond Ruhlmann, Athanassios Tzikas