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GB2143541A - Disperse methine dyes from 2-amino-5-carbothio-1,3,4-thiadiazole and aniline, tetrahydroquinoline, and benzomorpholine couplers - Google Patents

Disperse methine dyes from 2-amino-5-carbothio-1,3,4-thiadiazole and aniline, tetrahydroquinoline, and benzomorpholine couplers Download PDF

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Publication number
GB2143541A
GB2143541A GB08319571A GB8319571A GB2143541A GB 2143541 A GB2143541 A GB 2143541A GB 08319571 A GB08319571 A GB 08319571A GB 8319571 A GB8319571 A GB 8319571A GB 2143541 A GB2143541 A GB 2143541A
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alkyl
dyes
ch2ph
ch2ch2cn
alkoxy
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GB08319571A
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GB8319571D0 (en
GB2143541B (en
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Keith Hunt
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Kodak Ltd
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Kodak Ltd
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    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • 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
    • C09B23/14—Styryl dyes
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The title dyes of formulae (I)-(III) are new: <IMAGE> wherein R1-R10 are each H or specified substituents, R5 preferably being Me, Et, Ph, CH2Ph or CH2-CH = CH2. These dyes are useful for dyeing polyester fiber and its blends, and other synthetic fibers including cellulose acetate, cellulose triacetate, and acrylic fibres. They show marked improvement in one or more properties such as fastness to light, sublimation, crock, wash, ozone, and nitrogen oxide, and pH stability in the dyebath, and show little or no variation in shade or strength at different dyeing temperatures, e.g.. at 110 DEG C. and 130 DEG C dyeings on polyester. The dyes also show improved tinctorial strength over many commercially available dyes.

Description

SPECIFICATION Disperse methine dyes from 2-amino-5-carbothio-1 ,3,4-thiadiazole-2-acetonitrile and aniline, tetrahydroquinoline, and benzomorpholine couplers This invention concerns disperse methine dyes from 1 ,3,4-thiadiazole-2-acetonitrile containing a 5-position carbothio group such as ethylthio, and a coupler selected from the aniline, tetrahydroquinoline and benzomorpholine types which may be substituted. These dyes show marked improvement in the dyeing of polyester fiber and its blends, and other synthetic fibers including cellulose acetate, cellulose triacetate, and acrylic fibers.
The present dyes have the general formulae:
R5 is selected from alkyl, alkenyl of 3-6 carbons, phenyl, phenyl substituted with 1-3 of alkyl, alkoxy, halogen, CF3, OH, CN or NO2, and alkyl substituted with 1-3 of halogen, CF3, OH, CN, NO2, phenyl or alkoxy; Rl and R2 are independently selected from H, phenyl, alkyl, and said phenyl and alkyl substituted with 1-3 groups independently selected from hydroxyl, cyano, halogen, alkoxy, phenoxy, phthalimido (-NO2C8H4), succinimido (-NO2C4H4), alkanoyloxy, benzoyloxy, alkoxycarbonyl and phenoxycarbonyl; R3 and R4 are independently selected from H, halogen, alkanoylamino, alkyl and alkoxy;R6, R7, R8 and R9 are independently selected from H and alkyl; and R10 is hydrogen or 1 or 2 of alkyl, alkoxy, aryl, carbamoyl, alkylcarbamoyl, sulfamoyl, alkylsulfamoyl, alkylthio, arylthio, alkanoylamino, alkoxycarbonyl, alkanoyloxy, aryloxy or alkanoyl. All of the alkyl and alkylene moieties within the above definitions of the R1-R10 groups, e.g., the alkanoyl groups, contain 1-6 carbons, and the aryl moieties contain from 6-10 ring carbons.
Preferred dyes of the above formulae are those wherein R, is Et, Ph, n-Pr or i-Pr; R2 is selected from Et, Ph, n-Pr, CH2CH2CN, CH2CH2-succinimido, CH2CH2OPh, and the ester containing radicals CH2CH2OCOEt, CH2CH2OCOMe, CH2CH2OCO-Pr-n, CH2CH2OCO-Pr-i, CH2CH2OCO-Bu-n, CH2CH2OCOPh, and CH2CH2OCO-Bu-i wherein the -OCO-groups are either
0 0 II II -OC- or -CO-oriented; R3 and R4 are each H, Me or OMe; R5 is Me, Et, Ph, CH2Ph or CH2-CH = CH2; R6, R7, R8 and A9 are each H or Me; and A10 is hydrogen or 1 or 2 of alkyl, aryl, acylamino, alkoxy or phenoxy.
The present dyes can be used, for example, from an aqueous suspension in the presence of carriers at between 80 and 100"C., in the absence of carriers at between 1000"-130"C., or by the thermofixing process at 1 80-230 C.
The present dyes exhibit improvements over those disclosed, for example, in U.S. Patents 4,312,985 and 4,316,013 in one or more properties such as light, sublimation, crock, wash, ozone, and nitrogen oxide fastness, and pH stability in the dyebath, and show little or no variation in shade or strength between 11 0'C. and 1 30'C. dyeings on polyester. The present dyes also show improved tinctorial strength over many commercially available dyes.
The dyes of the present invention may be prepared by condensing the chosen 1,3,4thiadiazole-2-acetonitrile with an aldehyde substituted coupler according to the general equation:
NN NN R5-Su CH2 1 OHC-COUTN + R5 5t Sok k CN where COUPLER represents an aniline, tetrahydroquinoline or benzomorpholine coupler residue as defined above in the dye general formulae. The condensation may be effected in organic solvent solution in the presence of an organic base such as piperidine.
The following preparation illustrates the invention.
PREPARATION a) 5-thiobenzyl- 1, 3 ,4-thiadiazole-2-acetonitrile.
Carbon disulphide (31.2ml) was added dropwise to a stirred ice cold mixture of hydrazine hydrate (259), ethanol (1 25ml) and water (40ml), then stirred at 5"C for 1 hour. To the resulting suspension was added benzyl chloride (63.259) over a period of 1 hour with ice cooling. After addition was completed, the mixture was stirred without cooling for a further 1 1/2 hours, then filtered and the solid washed well with 1:1 aqueous ethanol and air dried to yield 549 of product, which was purified by recrystallisation from ethanol to give pure dithiocarbazinic acid, benzylester.
To an ice cold solution of malononitrile (3.39) in ethanol (5ml) and ethyl acetate (10ml) was added acetyl chloride (4.59) in ethylacetate (1 Oml) at such a rate that temperature remained less than 5'C. After 1 5 minutes at this temperature the reaction was stirred at room temperature for 5 hours. Dithiocarbazinic acid, benzyl ester (10g) and ethylacetate (40ml) was then added to the suspension of the imidate ester and warmed to 70'C for 2 hours. Upon cooling to 20'C, filtration and evaporation gave 10.29 of 5-thiobenzyl-1,3,4-thiadiazole-2-acetonitrile.
b) Dye from (a) and 4-formyl-N-ethyl-N-(ss-cyanoethyl)aniline.
The following procedure illustrates the preparation and use of the present dyes.
4-Formyl-Nethyl-N(ss-cyanoethyl) aniline (0.40 g; 0.002 mole) was dissolved in ethyl alcohol (10 ml). To this solution was added 5-benzylthio-1,3,4-thiadiazole-2-acetonitrile (0.5 g; 0.002 mole) and piperidine (0.1 ml.), and the mixture warmed on a steam bath for 1 5 minutes. After cooling overnight the orange crystalline dye of the formula
was collected by filtration and air dried. The dye was ball-milled in the presence of a lignin sulphonate dispersing agent for 24 hours and the resulting dispersion was applied to polyester fiber by dyeing from an aqueous bath at 1 30 C. for 1 hour. A deep yellow dyeing was produced of excellent color and fastness properties. Similar dyeings prepared in dyebaths buffered from pH 4-8 also gave deep dyeings indicating the dye had excellent pH stability in the dyebath.
The following tables further exemplify the dyes of the present invention.
TABLE I
Ex. R1 R2 R3 R4 R5 1 H H H H H 2 Et CH2CH2OOCC2H5 H H Me 3 Et CH2CH2OOCCH3 H H Me 4 Et CH2CH2OOC-C3H7-n H H Me 5 Et CH2CH2OOC-C3H7-i H H Me 6 Et CH2CH2OOC-C4H9-n H H Me 7 CH2CH2Cl H H H Me 8 Et CH2CH2OOC-C3H7-i H H Me 9 Ph Ph H H Me 10 Et CH2CH2COOCH3 H Me Me 11 Et CH2CH2COOC2H5 H Me Me 12 Et CH2CH2OOC-C3H7-i H Me Me 13 Et CH2CH2COO-C3H7-n H Me Me 14 Et CH2CH2OOC-C4H9-n H Me Me 15 Et CH2CH2OOC-C4H9-i Me Me Me 16 CH2CH2CN CH2CH2CN H Me n-Bu 17 Et CH2CH2-NO2C4H4* H Me i-Bu 18 n-Bu n-Bu OMe OMe Me 19 Ph Ph H H CH2Ph 20 Et CH2CH2CN H Me CH2Ph 21 CH2OPh CH2CH2-NO2C4H4 OEt NHCOCH3 CH2Ph 22 CH2OCH3 CH2OCH3 H H CH2Ph 23 H CH2CH2OOCPh H H CH2Ph 24 CH2CH2CN CH2CH2CN H H CH2Ph 25 H CH2CH2OPh H Me Et 26 H CH2CH2OC2H5 H H Et 27 Et CH2CH2OOC-C4H9-n H H Me 28 Et CH2CH2CN H H Et 29 Et CH2CH2-NO2C4H4 H Me Et 30 Et CH2CH2CN H Me Et * -NO2C4H4 represents succinimido 31 Et CH2OCH3 H H CH2-CH=CH2 32 Et Et H H Ph 33 Et Et H H Me 34 Et CH2CH2OCOPh H H Me 35 Ph Ph H H Me 36 Et CH2CH2OOCCH3 H H Me 37 Et CH2CH2OOCC2H5 H H Me 38 Et CH2CH2OOC-C3H7-i H Me Me 39 Et C6H4-p-OCH3 H OCH3 C6H3-o,p-di-NO2 40 C6H4-p-OPh C6H4-p-OC6H5 H OCH3 CH2OC2H5 41 Et C6H4-p-NO2C8H4 H OCH3 CH2CH2Cl 42 Et C6H4-p-NO2C4H4 H H CH2CF3 43 Et C6H4-p-OOCCH3 H H CH2CH2CH2OH 44 Et C6H4-p-OOCPh H H CH2CH2CN 45 Et CH2CH2OOC-C4H9-i H Me Me 46 Et CH2CH2CN H Me Me 47 Et CH2CH2-NO2C4H4 H Me Me 48 Me CH2CH2CN H H Et 49 Et Et -OMe -OMe Me 50 CH2CH2Cl CH2CH2Cl H H Et 51 Me CH2Br H H Et 52 Me CH2I H H Et 53 Me CH2F H H Et 54 CH2CH2OC2H5 CH2CH2OC2H5 H H Et 55 CH2OPh CH2OPh H H H 56 H CH2-NO2C8H4 H H H 57 H CH2-NO2C4H4 H H H 58 CH2OOCCH3 CH2OOCH3 H H H 59 CH2OOCPh CH2OOCPh H H H 60 CH2COOC2H5 CH2COOC2H5 H H Me 61 Et CH2NO2C4H4 H Me CH2Ph 62 H CH2CH2CHClCH2Cl H H Me 63 H C6H4-p-OH H H Me 64 CH2CH2OH CH2CH2OH H H Me 65 H CH2CH2CH2CH2OH H H Me 66 H C6H4-p-CH3 H H Me 67 Et Et H H CH2Ph 68 Et CH2CH2OOCPh H H CH2Ph 69 Et CH2CH2CN H H CH2Ph 70 Et CH2CH2OPh H Me Et 71 Et Et H H Et 72 Pr Pr H H Et 73 Et Et H H CH2CH=CH2 TABLE II
Ex.R2 R6 R7 R8 R5 R10 74 H H H H H H 75 CH2CH2OOCC2H5 H H H Me H 76 CH2CH2OOCCH3 H H H Me H 77 CH2CH2OOC-C3H7-n H H H Me 7-CH3 78 CH2CH2OOC-C3H7-i H H H Et 7-CH3 79 CH2CH2OOC-C4H9-n H H H Me 7-CH3 80 Et Et H H Me 7-CH3 81 CH2CH2OOCPh H Et H n-pR 7-OC2H5 82 CH2-NO2C8H4 H H n-Pr Me 5,7-di-CH3 83 CH2CH2COOCH3 Me Me Me Me 5,7-di-CH3 84 CH2CH2COOC2H5 Me Me Me Me 5,7-di-CH3 85 CH2CH2OOC-C3H7-i Me Me N-Bu Et 5,7-di-CH3 86 CH2CH2COO-C3H7-n H Me Me Me 7-OCH3 87 CH2CH2OOC-C4H9-n H Me Me Ph 7-NHCOCH3 88 CH2CH2OOC-C4H9-i H H Me Me 7-NHCOCH3 89 CH2CH2CN H Et Me n-Bu 7-C6H5 90 CH2CH2-NO2C4H4 H H Me i-Bu 7-CONH2 91 n-Bu Me Me Me Me 7-CONHC2H5 92 Ph H H Et CH2Ph 7-SO2NH2 93 CH2CH2CN H H Me CH2Ph 7-SO2NHCH3 94 CH2CH2-NO2C4R4 H H Me C6H4-p-C2H5 7-SC2H5 95 Et H H H CH2Ph 7-SC6H5 96 CH2CH2OOCPh H H H CH2Ph 7-NHCOCH3 97 CH2CH2CN H H H CH2Ph 98 CH2CH2OPh H Me Me Et 7-COOCH3 99 CH2CH2OC2H5 H H H CH2CH2Ph 7-OOCCH3 100 n-Pr H H H Et 101 CH2CH2CN H H H Et 7-OC6H5 102 CH2CH2-NO2C4H4 H Me Me Et 7-COCH3 103 CH2CH2CN H Me Me Et 7-CH3 104 CH2OCH3 H H H CH2-CH=CH2 5,7-di-OCH3 105 Et H H H Ph H 106 C6H4-p-OCH3 H Me Me C6H3-o,p-di-NO2 H 107 C6H4-p-OC6H5 H Me Me CH2OC2H5 H 108 C6H4-NO2C8H4 H Me Me CH2CH2Cl 7-CH3 109 C6H4-p-NO2C4H4 H Me Me CH2CF3 7-CH3 110 C6H4-p-OOCCH3 H Me Me CH2CH2CH2OH 7-CH3 111 C6H4-p-OOCPh H Me Me CH2CH2CN 7-CH3 112 CH2CH2CN H H H Et 7-CH3 113 CH2CH2Cl H H H Et 7-CH3 114 CH2Br H H H Et 7-CH3 115 CH2I H H H Et 7-CH3 116 CH2F H H H Et 7-C6H5 117 CH2CH2OC2H5 H H H Et 7-C6H5 118 CH2OPh H H H H 7-C6H5 119 CH2-NO2C8H4 H H H H 7-C6H5 120 CH2-NO2C4H4 H H H H 7-C6H5 121 CH2OOCCH3 H H H H 7-C6H5 122 CH2OOCPh H H H H 7-CH3 123 CH2COOCH3 H H H Me 7-CH3 124 CH2CH2CHClCH2Cl H H H Me 7-CH3 125 C6H4-p-OH H H H Me 7-CH3 126 CH2CH2OH H H H Me 7-CH3 127 CH2CH2CH2CH2OH H H H Me 7-CH3 128 C6H4-p-CH3 H H H Me 7-CH3 TABLE III
Ex. R2 R9 R5 R10 129 H H H H 130 CH2CH2OOCC2H5 H Me H 131 CH2CH2OOCC2H5 H Me H 132 CH2CH2OOCCH3 H Me H 133 CH2CH2OOC-C3H7-n H Me H 134 CH2CH2OOC-C3H7-i H Me 6-CH3 135 CH2CH2OOC-C4H90-n n-Pr Me 6-CH3 136 Et H Me 6-SC6H5 137 CH2CH2OOCPh H Me 6-SO2NH2 138 CH2-NO2C8H4 H Me 6-SO2NHCH3 139 CH2CH2COOCH3 Me Me 6-CONHC2H5 140 CH2CH2COC2H5 Me Me 6,8-di-CH3 141 CH2CH2OOC-C3H7-i Me Me 6,8-di-CH3 142 CH2CH2COO-C3H7-n Me Me 6,8-di-CH3 143 CH2CH2OOC-C4H9-n Me Me 6,8-di-CH3 144 CH2CH2OOC-C4H9-i Me Me H 145 CH2CH2CN Me Me H 146 CH2CH2-NO2C4H4 Me Me H 147 Et Me Me 6-OCH3 148 Ph n-Bu CH2Ph 6-OCH3 149 CH2CH2CN Me CH2Ph 6-NHCOCH3 150 CH2CH2-NO2C4H4 Me C6H4-p-C2H5 6-NHCOCH3 151 Et H CH2Ph 6-C6H5 152 CH2CH2OOCPh H CH2Ph 6-CONH2 153 CH2CH2CN H CH2Ph 6-SC2H5 154 CH2CH2OPh Me Et 6-SC2H5 155 CH2CH2OC2H5 H Et 6-COOCH3 156 n-Pr H CH2CH2Ph 6-CH3 157 CH2CH2CN H Et 6-CH3 158 CH2CH2-NO2C4H4 Me Et 6-CH3 159 CH2CH2CN Me Et 6-CH3 160 CH2OCH3 H CH2-CH=CH2 6-CH3 161 Et H Ph 6-CH3 162 C6H4-p-OCH3 H C6H3-o,p-di-NO2 6-CONHC2H5 163 C6H4-p-OC6H5 H CH2OC2H5 6-CONHC2H5 164 C6H4-p-NO2C8H4 H CH2CH2Cl 6-CONHC2H5 165 C6H4-p-NO2C4H4 H CH2CF3 H 166 C6H4-p-OOCCH3 H CH2CH2CH2OH H 167 C6H4-p-OOCPh H CH2CH2CN H 168 CH2CH2CN Me Et 6,8-di-SC2H5 169 CH2CH2Cl Me Et 5-OCH3 170 CH2Br Me Et H 171 CH2I Me Et H 172 CH2F Me Et H 173 CH2CH2OC2H5 H Et H 174 CH2OPh H H H 175 CH2-NO2C8H4 H H H 176 CH2-NO2C4H4 H H H 177 CH2OOCCH3 H H H 178 CH2OOCPh H H H 179 CH2COOCH3 H Me H 180 CH2CH2CHClCH2Cl H Me H 181 C6H4-p-OH H Me H 182 CH2CH2OH H Me H 183 CH2CH2CH2CH2OH H Me H 184 C6H4-p-CH3 H Me H

Claims (3)

1. A dye having one of the formulae
R5 is selected from H, alkyl, alkenyl of 3-6 carbon atoms, phenyl, phenyl substituted with 1-3 of alkyl, alkoxy, halogen, CF3, OH, CN or NO2, and alkyl substituted with 1-3 of halogen, CF3, OH, CN, NO2, phenyl or alkoxy; R, and R2 are independently selected from H, phenyl, alkyl, and said phenyl and alkyl substituted with 1-3 groups independently selected from hydroxyl cyano, halogen, alkoxy, phenoxy, phthalimido, succinimido, alkanoyloxy, benzoyloxy, alkoxycarbonyl and phenoxycarbonyl: R3 and R4 are independently selected from H, halogen, alkanoylamino, alkyl, and alkoxy:R6, R7, R8 and A9 are independently selected from H and alkyl; and R10 is hydrogen or 1 or 2 of alkyl, alkoxy, aryl, carbamoyl, alkylcarbamoyl, sulfamoyl, alkylsulfamoyl, alkylthio, arylthio, alkanoylamino, alkoxycarbonyl, alkanoyloxy, aryloxy or alkanoyl.
2. A dye according to Claim 1 wherein R, is H, Et, Ph, n-Pr or i-Pr; R2 is selected from Et, Ph, n-Pr, CH2CH2CN, CH2CH2-succinimido, CH2CH20Ph, and the ester containing radicals CH2CH2OCOEt, CH2CH2OCOMe, CH2CH2OCO-Pr-n, CH2CH20CO-Pr-i, CH2CH2OCO-Bu-n, CH2SH20COPh, and CH2CH2OCO-Bu-i wherein the -OCO-groups are either
Q o -OC- or -CO-oriented; R3 and R4 are each H, Me or OME; R5 is Me, Et, Ph, CH2Ph or CH2-CH = CH2; R6, R7, R8 and Rs are each H or Me; and R10 is hydrogen or 1 or 2 of alkyl, aryl, alkanoylamino, alkoxy or aryloxy.
3. The dye according to Claim 1 which has one of the formulae:
GB08319571A 1983-07-20 1983-07-20 Disperse methine dyes from 2-amino-5-carbothio-1,3,4-thiadiazole-2-acetonitrile and aniline, tetrahydroquinoline, and benzomorpholine couplers Expired GB2143541B (en)

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GB08319571A GB2143541B (en) 1983-07-20 1983-07-20 Disperse methine dyes from 2-amino-5-carbothio-1,3,4-thiadiazole-2-acetonitrile and aniline, tetrahydroquinoline, and benzomorpholine couplers

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GB08319571A GB2143541B (en) 1983-07-20 1983-07-20 Disperse methine dyes from 2-amino-5-carbothio-1,3,4-thiadiazole-2-acetonitrile and aniline, tetrahydroquinoline, and benzomorpholine couplers

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US5116530A (en) * 1988-10-17 1992-05-26 Canon Kabushiki Kaisha Mesomorphic compound, liquid crystal composition containing same and liquid crystal device using same
FR2921381A1 (en) * 2007-09-21 2009-03-27 Oreal HEMICYANINE STYRYLE THIOL / DISULFIDE DYE, TINCTORIAL COMPOSITION COMPRISING THE DYE, METHOD OF CLEANING KERATINIC MATERIALS FROM THAT COLORANT
US7717964B2 (en) 2007-09-21 2010-05-18 L'oreal S.A. Styryl thiol/disulfide compound with a hydroxy(cyclo)alkylamino unit, process for lightening keratin materials using same
US7744657B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Styrl tetrahydroquinolinium thiol/disulfide dye compound and method for lightening keratin materials using the same
US7744658B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Indole-derived styryl dye comprising an alkylene linker, a dye composition comprising this dye, and a process for lightening keratin materials using this dye
US7780743B2 (en) 2006-03-24 2010-08-24 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity, and method for lightening keratin materials using said at least one fluorescent entity
US8070830B2 (en) 2006-03-24 2011-12-06 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity comprising at least one heterocycle, with at least one internal cationic charge, and method for lightening keratin materials using said at least one fluorescent entity

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ATE508170T1 (en) 2006-03-24 2011-05-15 Oreal DYEING COMPOSITION COMPRISING A THIOL/DISULFIDE LUMINOUS DYE WITH AMINE GROUPS AND AN INTERNAL CATIONIC CHARGE AND METHOD FOR LIGHTENING KERATIN MATERIAL USING THIS DYE

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5116530A (en) * 1988-10-17 1992-05-26 Canon Kabushiki Kaisha Mesomorphic compound, liquid crystal composition containing same and liquid crystal device using same
US7780743B2 (en) 2006-03-24 2010-08-24 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity, and method for lightening keratin materials using said at least one fluorescent entity
US8070830B2 (en) 2006-03-24 2011-12-06 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity comprising at least one heterocycle, with at least one internal cationic charge, and method for lightening keratin materials using said at least one fluorescent entity
FR2921381A1 (en) * 2007-09-21 2009-03-27 Oreal HEMICYANINE STYRYLE THIOL / DISULFIDE DYE, TINCTORIAL COMPOSITION COMPRISING THE DYE, METHOD OF CLEANING KERATINIC MATERIALS FROM THAT COLORANT
EP2062945A3 (en) * 2007-09-21 2010-01-20 L'Oréal Hemicyanin styryl thiol/disulfide dye, dye composition comprising this dye, process for lightening keratin materials using this dye
US7717964B2 (en) 2007-09-21 2010-05-18 L'oreal S.A. Styryl thiol/disulfide compound with a hydroxy(cyclo)alkylamino unit, process for lightening keratin materials using same
US7727287B2 (en) 2007-09-21 2010-06-01 L'oreal S.A. Hemicyanin styryl thiol/disulfide dye, composition comprising hemicyanin styryl thoil/disulfide dye, and method for lightening keratin materials using hemicyanin styryl thiol/disulfide dye
US7744657B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Styrl tetrahydroquinolinium thiol/disulfide dye compound and method for lightening keratin materials using the same
US7744658B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Indole-derived styryl dye comprising an alkylene linker, a dye composition comprising this dye, and a process for lightening keratin materials using this dye

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GB2143541B (en) 1987-04-08

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