WO2002066562A1 - Dye compounds - Google Patents

Dye compounds Download PDF

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Publication number
WO2002066562A1
WO2002066562A1 PCT/IB2002/000513 IB0200513W WO02066562A1 WO 2002066562 A1 WO2002066562 A1 WO 2002066562A1 IB 0200513 W IB0200513 W IB 0200513W WO 02066562 A1 WO02066562 A1 WO 02066562A1
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Prior art keywords
alkyl
aryl
halogen
substituted
alkoxyl
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PCT/IB2002/000513
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French (fr)
Inventor
Bansi Lal Kaul
Jean-Christophe Graciet
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Clariant International Ltd
Clariant Finance (Bvi) Limited
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Publication of WO2002066562A1 publication Critical patent/WO2002066562A1/en

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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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/08—Naphthalimide dyes; Phthalimide dyes
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
    • C09B69/102—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye containing a perylene dye
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes

Definitions

  • This invention relates to new fluorescent or non-fluorescent dye compounds having a terminal hydroxy, carboxylic acid/ester or amino group.
  • Colorants not covalently bond in a polymer matrix tend to agglomerate and to crystalize leading to inhomogeneous distribution of colorants within the matrix.
  • Fluorescent colorants in particular often loose their fluorescent properties by agglomeration of fluorescent sites (quenching). Furthermore with non covalently bond colorants, fading or bleeding of the colorant occurs.
  • US 6,103,006 discloses fluorescent polymeric pigments with increased lightfastness obtained by the polycondensation of dye monomers with at least two functional groups like diamine, dialcohol or dicarboxylic acid.
  • the functional groups for the polycondensation are directly located at the dye moiety as in the anhydride or diacid form of the BXDA fluorescent dye.
  • WO 99/21937 discloses a two phase interpenetrating polymer network system with a dye functionalized polymer in the second phase.
  • the optionally fluorescent dye is covalently bond to the polymer to slow migration and to enhance compatibility, e.g. a hydroxy functional dye (YGOH) is reacted into a polyurethane or an acrylate functional dye (YGOAcr) is reacted into a respective chain growth polymer.
  • YGOH hydroxy functional dye
  • YGOAcr acrylate functional dye
  • the hydroxy functionalized spacer is attached to the molecule in a condensation reaction strating from the anhydride of the dye molecule.
  • One objective of the present invention are new functionalized dye compounds having terminal hydroxy, carboxylic acid/ester or amino groups, which can be reacted into polyurethane, polyester or aminoformaldehyde networks.
  • a further objective is a process for the preparation of such new functionalized dye compounds, as well as a process for reacting these compounds into polyurethane, polyester or aminoformaldehyde networks.
  • the new dye compounds are of the general formula (I)
  • Ri is C ⁇ . 12 alkylene, C ⁇ . 12 alkoxylene C 6-! o arylene, (C 6-K) ) aryl-(C ⁇ -6 ) alkylene or (C ⁇ -6 ) alkyl-(C 6 - ⁇ o) arylene, the alkylene and/or arylene radicals optionally being substituted by hydroxy 1, C ⁇ - 6 alkoxyl, C 6 . t o aryloxy or halogen,
  • X is hydroxy, COOR' or NHR' with R' being hydrogen C ⁇ -6 alkyl, C 6- ⁇ 0 aryl, (C 6- , 0 ) aryl- (C ⁇ -6 ) alkyl or (C 1-6 ) aIkyl-(C 6 . ⁇ 0 ) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, C ⁇ -6 alkoxyl, C 6- ⁇ 0 aryloxy or halogen and A is a substituted or unsubstituted aromatic or heterocyclic ring system of the general formula (Ila) to (Va)
  • R" is hydrogen, C ⁇ -6 alkyl, C 6- ⁇ o aryl, (C 6- ⁇ o) aryl-(C 1-6 ) alkyl or (C 1-6 ) alkyl-(C 6-
  • aryl the alkyl and/or aryl radicals optionally being substituted by hydroxy 1, C ⁇ -6 alkoxyl, C 6 - ⁇ o aryloxy or halogen,
  • R 3 is hydrogen, halogen, NRjRs, l ⁇ O or R ⁇ S, in which Rt is hydrogen C !-6 alkyl, C 6 - ⁇ o aryl, (C ⁇ -io) aryl-(C ⁇ -6 ) alkyl or (C ⁇ -6 ) alkyl-(C 6-) o) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, C ⁇ -6 alkoxyl, C 6- ⁇ o aryloxy or halogen;
  • R 5 is C ⁇ -6 alkyl, C 6- ⁇ o aryl, (C 6- ⁇ 0 ) aryl-(C ⁇ -6 ) alkyl or (C 1-6 ) alkyl-(C 6- ⁇ o) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, C ⁇ -6 alkoxyl, C 6- ⁇ o aryloxy or halogen.
  • the ring labeled B is fused on in 1,2-, 2,3- or 3,4- position and is selected from the group consisting of the moieties (1) to (8)
  • R 7 and R 8 are, independently from each other, hydrogen, C ⁇ -8 alkyl, C 5-6 cycloalkyl, benzyl, benzanilide, phenyl or naphthyl whereby benzanilide, phenyl and naphthyl groups may be mono- or poly-substituted by radicals selected from the group halogen, nitro, C ⁇ -8 alkyl, C 5 .
  • R 9 is, independently from R 7 and R 8 , hydrogen, hydroxy, C ⁇ -8 alkyl, C 5-6 cycloalkyl, benzyl, benzanilide, phenyl or naphthyl whereby benzanilide, phenyl and naphthyl groups may be mono- or poly-substituted by radicals selected from the group halogen, nitro, C ⁇ -8 alkyl, C 5-6 cycloalkyl, benzyl, phenyl or naphthyl, COOalkyl, C ⁇ - 3 alkoxy or trifluoromethyl.
  • the Ring B is annelated in 3,4-position with a group of the formula - NR 7 (CO) n -NR 8 - or -O-CO-NR 7 - , n is 1 or 2, R 7 and R 8 are independently hydrogen, C ⁇ .
  • alkyl C 6- ⁇ o aryl, (C 6- ⁇ o) aryl-(C ⁇ - 6 )alkyl or (C ⁇ -6 )alkyl-(C 6- ⁇ 0 )aryl, the alkyl and/or aryl radicals optionally being substituted by amino, C ⁇ -6 alkylamino, C 6- ⁇ o cycloalkylamino, hydroxyl, C ⁇ -6 alkoxyl, C 6- ⁇ o aryloxy or halogen.
  • the preferred spacer Ri is a C M2 alkylene, more preferred C 3-8 alkylene, most preferably C 6 alkylene.
  • the dye compounds of formulae (I) are obtained by the reaction of the dye moiety functionalized with a leaving group (L), e.g. chlorine or bromine, with an amino alcohol, an amino acid ester or a diamine comprising the respective spacer.
  • L e.g. chlorine or bromine
  • Preferred dye compounds according to the invention are those of the general formulae (IV) and (V),
  • the hydroxy, carboxylic acid/ester or amino group on the free end of the spacer can be reacted into a polymer network, e.g. polyurethane, polyester or aminoformaldehyde resin.
  • a polymer network e.g. polyurethane, polyester or aminoformaldehyde resin.
  • the dye compound is mixed into a respective reactive mixture comprising isocyanates or formaldehyde and optionally other carboxy, hydroxy or amine functionalized compounds before the reaction is carried out.
  • a respective reactive mixture comprising isocyanates or formaldehyde and optionally other carboxy, hydroxy or amine functionalized compounds before the reaction is carried out.
  • the polyreactions to obtain polyurethane, polyester or aminoformaldehyde resins are well known in the art.
  • the dye compounds according to the invention are suitable for the mass pigmentation of synthetic resins, e.g. polyurethane masses, polyester or aminoformaldehyde resins.
  • the obtained resins according to the invention are suitable, as colorants in powders and powder coating materials, especially in triboelectrically or electrokinetically sprayable powder coating materials which are used for the surface coating of articles made, for example, from metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.
  • Powder coating resins that are typically employed are epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane resins and acrylic resins, together with customary hardeners. Combinations of resins are also used. For example, epoxy resins are frequently employed in combination with carboxyl- and hydroxyl-containing polyester resins.
  • Typical hardener components are, for example, acid anhydrides, imidazoles and also dicyanodiamide and its derivatives, blocked isocyanates, bisacylurethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
  • Example 1 4-bromonaphthalic anhydride (10 part) is suspended in N-methylpyrrolidone (30 parts) in presence of 1 part of -toluenesulfonic acid. 4 parts of ⁇ -diaminobenzene are added and the reaction mixture is stirred to 150°C. When the reaction is completed, the mixture is cooled to 25°C, filtered and washed with methanol. After drying under vacuum, 1 1 parts of a pale yellow powder are obtained (85% yield). This product is then suspended in 28 parts of methylamino-propylamine and the resulting suspension is heated to 130°C until reaction is completed. The mixture is cooled to 95°C and poured into water at 90°C. After stirring and cooloing to 25°C , the orange suspension is filterd and washed with water until no amine remains in the presscake. After drying, 10.7 parts of an orange-red powder are obtained (95% yield).

Abstract

This invention relates to new fluorescent or non-fluorescent dye compounds having a terminal hydroxy, carboxylic acid/ester or amino group and a process for their preparation. The invention further discloses a process of reacting said compounds into polyurethane, polyester or aminoformaldehyde resins. The dye compounds provide excellent properties, especially high temperature stability and easy applicability.

Description

DYE COMPOUNDS
This invention relates to new fluorescent or non-fluorescent dye compounds having a terminal hydroxy, carboxylic acid/ester or amino group.
Articles containing colorants are known to loose their colour when exposed to solar radiation for extended times. In particular, fluorescent colorants degrade more quickly than conventional colorants, often turning colourless on exposure to daily solar radiation within days or months.
Colorants not covalently bond in a polymer matrix tend to agglomerate and to crystalize leading to inhomogeneous distribution of colorants within the matrix. Fluorescent colorants in particular often loose their fluorescent properties by agglomeration of fluorescent sites (quenching). Furthermore with non covalently bond colorants, fading or bleeding of the colorant occurs.
US 6,103,006 (DiPietro) discloses fluorescent polymeric pigments with increased lightfastness obtained by the polycondensation of dye monomers with at least two functional groups like diamine, dialcohol or dicarboxylic acid. The functional groups for the polycondensation are directly located at the dye moiety as in the anhydride or diacid form of the BXDA fluorescent dye.
Figure imgf000002_0001
Besides the above mentioned polycondensation process the polyreaction of chain growth polymers can be utilised to react dye monomers into a polymer backbone.
WO 99/21937 (3M) discloses a two phase interpenetrating polymer network system with a dye functionalized polymer in the second phase. The optionally fluorescent dye is covalently bond to the polymer to slow migration and to enhance compatibility, e.g. a hydroxy functional dye (YGOH) is reacted into a polyurethane or an acrylate functional dye (YGOAcr) is reacted into a respective chain growth polymer. The hydroxy functionalized spacer is attached to the molecule in a condensation reaction strating from the anhydride of the dye molecule.
Figure imgf000003_0001
One objective of the present invention are new functionalized dye compounds having terminal hydroxy, carboxylic acid/ester or amino groups, which can be reacted into polyurethane, polyester or aminoformaldehyde networks.
A further objective is a process for the preparation of such new functionalized dye compounds, as well as a process for reacting these compounds into polyurethane, polyester or aminoformaldehyde networks.
These objectives are achieved by new dye compounds, having terminal hydroxy, carboxylic acid/ester or amino groups which are separated from the dye moiety by a spacer.
The new dye compounds are of the general formula (I)
A-N— R-X (I) π
wherein Ri is Cι.12 alkylene, Cι.12 alkoxylene C6-!o arylene, (C6-K)) aryl-(Cι-6) alkylene or (Cι-6) alkyl-(C6-ιo) arylene, the alkylene and/or arylene radicals optionally being substituted by hydroxy 1, Cι-6 alkoxyl, C6.to aryloxy or halogen,
X is hydroxy, COOR' or NHR' with R' being hydrogen Cι-6 alkyl, C6-ι0 aryl, (C6-,0) aryl- (Cι-6) alkyl or (C1-6) aIkyl-(C6.ι0) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, Cι-6 alkoxyl, C6-ι0 aryloxy or halogen and A is a substituted or unsubstituted aromatic or heterocyclic ring system of the general formula (Ila) to (Va)
Figure imgf000004_0001
(Ila) (Ilia) (IVa) (Va)
wherein R" is hydrogen, Cι-6 alkyl, C6-ιo aryl, (C6-ιo) aryl-(C1-6) alkyl or (C1-6) alkyl-(C6-
10) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxy 1, Cι-6 alkoxyl, C6-ιo aryloxy or halogen,
R3 is hydrogen, halogen, NRjRs, l^O or R^S, in which Rt is hydrogen C!-6 alkyl, C6-ιo aryl, (Cβ-io) aryl-(Cι-6) alkyl or (Cι-6) alkyl-(C6-)o) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, Cι-6 alkoxyl, C6- ιo aryloxy or halogen;
R5 is Cι-6 alkyl, C6-ιo aryl, (C6-ι0) aryl-(Cι-6) alkyl or (C1-6) alkyl-(C6-ιo) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, Cι-6 alkoxyl, C6-ιo aryloxy or halogen.
The ring labeled B is fused on in 1,2-, 2,3- or 3,4- position and is selected from the group consisting of the moieties (1) to (8)
Figure imgf000004_0002
Figure imgf000005_0001
wherein R7 and R8 are, independently from each other, hydrogen, Cι-8alkyl, C5-6 cycloalkyl, benzyl, benzanilide, phenyl or naphthyl whereby benzanilide, phenyl and naphthyl groups may be mono- or poly-substituted by radicals selected from the group halogen, nitro, Cι-8alkyl, C5.6cycloalkyl, benzyl, phenyl or naphthyl, COOalkyl, Cι-3 alkoxy or trifluoromethyl and R9 is, independently from R7 and R8, hydrogen, hydroxy, Cι-8alkyl, C5-6 cycloalkyl, benzyl, benzanilide, phenyl or naphthyl whereby benzanilide, phenyl and naphthyl groups may be mono- or poly-substituted by radicals selected from the group halogen, nitro, Cι-8alkyl, C5-6cycloalkyl, benzyl, phenyl or naphthyl, COOalkyl, Cι-3alkoxy or trifluoromethyl.
Preferred, the Ring B is annelated in 3,4-position with a group of the formula - NR7(CO)n-NR8- or -O-CO-NR7- , n is 1 or 2, R7 and R8 are independently hydrogen, C\. 6 alkyl, C6-ιo aryl, (C6-ιo) aryl-(Cι-6)alkyl or (Cι-6)alkyl-(C6-ι0)aryl, the alkyl and/or aryl radicals optionally being substituted by amino, Cι-6 alkylamino, C6-ιo cycloalkylamino, hydroxyl, Cι-6 alkoxyl, C6-ιo aryloxy or halogen.
The preferred spacer Ri is a CM2 alkylene, more preferred C3-8 alkylene, most preferably C6 alkylene.
The dye compounds of formulae (I) are obtained by the reaction of the dye moiety functionalized with a leaving group (L), e.g. chlorine or bromine, with an amino alcohol, an amino acid ester or a diamine comprising the respective spacer. The product is obtained in high yield.
A-L H2N- -R— X ^ A-N — Rr- X
-HL H wherein A, Ri and X are defined as above, L is a leaving group.
Preferred dye compounds according to the invention are those of the general formulae (IV) and (V),
Figure imgf000006_0001
(IV)
(V) wherein Ri and X are defined as above and R3 is hydrogen.
Other preferred dye compounds according to the invention are those of the general formula (III)
Figure imgf000006_0002
(III) wherein R\ and X are defined as above and the Ring B is annelated in 3,4-position with a group of the formula -NR7(CO)n-NR8-, n is 1 or 2, R7 and R8 are independently hydrogen or Cι-6 alkyl.
The hydroxy, carboxylic acid/ester or amino group on the free end of the spacer can be reacted into a polymer network, e.g. polyurethane, polyester or aminoformaldehyde resin.
To obtain such colored polymer resins, the dye compound is mixed into a respective reactive mixture comprising isocyanates or formaldehyde and optionally other carboxy, hydroxy or amine functionalized compounds before the reaction is carried out. The polyreactions to obtain polyurethane, polyester or aminoformaldehyde resins are well known in the art.
The dye compounds according to the invention are suitable for the mass pigmentation of synthetic resins, e.g. polyurethane masses, polyester or aminoformaldehyde resins.
The obtained resins according to the invention are suitable, as colorants in powders and powder coating materials, especially in triboelectrically or electrokinetically sprayable powder coating materials which are used for the surface coating of articles made, for example, from metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.
Powder coating resins that are typically employed are epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane resins and acrylic resins, together with customary hardeners. Combinations of resins are also used. For example, epoxy resins are frequently employed in combination with carboxyl- and hydroxyl-containing polyester resins. Typical hardener components (as a function of the resin system) are, for example, acid anhydrides, imidazoles and also dicyanodiamide and its derivatives, blocked isocyanates, bisacylurethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
The following examples illustrate the invention. Unless otherwise specified, parts and percentages used in the examples are on a weight to weight basis.
Example 1 4-bromonaphthalic anhydride (10 part) is suspended in N-methylpyrrolidone (30 parts) in presence of 1 part of -toluenesulfonic acid. 4 parts of ø-diaminobenzene are added and the reaction mixture is stirred to 150°C. When the reaction is completed, the mixture is cooled to 25°C, filtered and washed with methanol. After drying under vacuum, 1 1 parts of a pale yellow powder are obtained (85% yield). This product is then suspended in 28 parts of methylamino-propylamine and the resulting suspension is heated to 130°C until reaction is completed. The mixture is cooled to 95°C and poured into water at 90°C. After stirring and cooloing to 25°C , the orange suspension is filterd and washed with water until no amine remains in the presscake. After drying, 10.7 parts of an orange-red powder are obtained (95% yield).
Figure imgf000008_0001
Example 2
4-bromonaphthalic anhydride (10 parts) is suspended in N-methylpyrrolidone (40 parts) in presence of 1 part of p-toluenesulfonic acid. 6 parts of 1,4- diaminobenzimidazolone are added and the reaction mixture is stirred to 150°C under nitrogen atmosphere. When the reaction is completed, the mixture is cooled to 25°C, filtered and washed with methanol. After drying under vacuum, 10 parts of an orange- red powder are obtained (67% yield). This product is then suspended in 40 parts of methylamino-propylamine and the resulting suspension is heated to 130°C until reaction is completed. The mixture is cooled to 95°C and poured into water at 90°C. After stirring and cooling to 25°C , the red-orange suspension is filtered and washed with water until no amine remains in presscake. After drying, 8.6 parts of an orange-red powder are obtained (85% yield).
Figure imgf000008_0002
Example 3
4-bromonaphthalic anhydride (10 parts) is suspended in N-methylpyrrolidone (40 parts) in presence of 1 part of /?-toluenesulfonic acid. 6 parts of 1,8-diaminonaphthaIene are added and the reaction mixture is stirred to 150°C under nitrogen atmosphere. When the reaction is completed, the mixture is cooled to 25°C, filtered and washed with methanol. After drying under vacuum, 13.2 parts of a violet powder are obtained (94% yield). This product is then suspended in 40 parts of methylamino-propylamine and the resulting suspension is heated to 130°C until reaction is completed. The mixture is cooled to 95°C and poured into water at 90°C. After stirring and cooling to 25°C , the violet suspension is filterd and washed with water until no amine remains in presscake. After drying, 9.2 parts of a violet powder are obtained (71% yield).
Figure imgf000009_0001

Claims

Claims
A dye compound according to the general formula (I)
A-N- -R— X (I) H
wherein Ri is CM2 alkylene, Cι_ι2 alkyoxylene, C6-ιo arylene, (C6-ι0) aryl-(Cι-6) alkylene or (Cι-6) aIkyl-(C6-ιo) arylene, the alkylene and/or arylene radicals optionally being substituted by hydroxyl, C[-6 alkoxyl, C6-ιo aryloxy or halogen,
X is hydroxy, COOR' or NHR' with R' being hydrogen, Cι-6 alkyl, Cβ-io aryl, (C6-ιo) aryl-(Cι-6) alkyl or (Cι-6) alkyl-(C6-ιo) aryl, the alkyl and or aryl radicals optionally being substituted by hydroxyl, Cι-6 alkoxyl, Cβ-io aryloxy or halogen,
A is a substituted or unsubstituted aromatic or heterocyclic ring system of the general formulae (Ila), (Ilia), (IVa) or (Va)
Figure imgf000010_0001
(Ila) (Ilia) (IVa) (Va)
wherein R" is hydrogen, C)-6 alkyl, C6-ιo aryl, (C6-ιo) aryl-(C]-6) alkyl or (Cι-6) alkyl-(C6-ιo) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, Cι-6 alkoxyl, C6-to aryloxy or halogen, the Ring B is annelated in 3,4-position with a group of the formula -NR7(CO)n- NR8- or -O-CO-NR7- , n is 1 or 2, R7 and R8 are independently hydrogen, Cι-6 alkyl, C6-ιo aryl, (C6-[0) aryl-(C1-6)alkyl or (Cι-6)alkyl-(C6-ι0)aryl, the alkyl and/or aryl radicals optionally being substituted by amino, Q-6 alkylamino, C6-ιo cycloalkylamino, hydroxyl, Cι-6 alkoxyl, C6-ι0 aryloxy or halogen,
R3 is hydrogen, halogen, NR4R5, R}O or R4S, in which T is hydrogen Cι-6 alkyl, C6-ιo aryl, (C6-ιo) aryl-(Cι-6) alkyl or (Cι-6) alkyl-(C6- ιo) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, Cι-6 alkoxyl, C6-ι0 aryloxy or halogen;
R5 is Cι-6 alkyl, C6-ι0 aryl, (C6-ι0) aryl-(Cι-6) alkyl or (Cι-6) alkyl-(C6-ι0) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, Cι-6 alkoxyl, C6-ιo aryloxy or halogen.
2. A dye compound according to claim 1 characterized in that Ri has a chain lenght of C to , preferably of C6.
3. A process for the preparation of hydroxy, carboxylic acid/ester or amino functionalized dye compounds according to claims 1 or 2 characterized in that the respective dye moiety functionalized with a leaving group is reacted with an aminoalcohol an aminoacid/ester or a diamine comprising the respective spacer.
Use of a dye compound according to claim 1 or 2 as colorant.
A process of reacting a hydroxy, carboxylic acid, ester or amino functionalized dye compound according to claims 1 or 2 into a polyurethane, polyester or aminoformaldehyde resin, characterized in that the dye compound is mixed into the polyreaction mixture before the resin is formed.
PCT/IB2002/000513 2001-02-21 2002-02-20 Dye compounds WO2002066562A1 (en)

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WO2005075574A1 (en) * 2004-02-07 2005-08-18 Wella Aktiengesellschaft Neutral and cationic naphthalene derivatives and dyes containing said compounds for dyeing keratin fibers
FR2871160A1 (en) * 2004-06-08 2005-12-09 Oreal Particles dispersion in organic or non aqueous medium, useful as e.g. make-up product, comprises ethylinic polymer comprising skeleton insoluble in the medium and part soluble in the medium containing lateral chains in covalent manner
FR2871161A1 (en) * 2004-06-08 2005-12-09 Oreal Dispersion (solid particles), useful as e.g. make-up product, comprises ethylinic polymer comprising a structure (insoluble and partly soluble in the medium) containing lateral chains in covalent manner
WO2006005823A1 (en) * 2004-06-08 2006-01-19 L'oreal Dispersion of ethylene polymer particles, composition containing same and treatment method
WO2006005822A1 (en) * 2004-06-08 2006-01-19 L'oreal Dispersion of ethylene polymer particles, composition containing same and treatment method
CN102898860A (en) * 2012-09-26 2013-01-30 大连理工大学 Two-photon fluorescent dye taking isoquinolinone as parent, preparation method thereof and application
WO2021206059A1 (en) * 2020-04-07 2021-10-14 オリヱント化学工業株式会社 Colorant, master batch containing same, colored resin composition, and molded article

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WO2005075574A1 (en) * 2004-02-07 2005-08-18 Wella Aktiengesellschaft Neutral and cationic naphthalene derivatives and dyes containing said compounds for dyeing keratin fibers
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FR2871161A1 (en) * 2004-06-08 2005-12-09 Oreal Dispersion (solid particles), useful as e.g. make-up product, comprises ethylinic polymer comprising a structure (insoluble and partly soluble in the medium) containing lateral chains in covalent manner
WO2006005823A1 (en) * 2004-06-08 2006-01-19 L'oreal Dispersion of ethylene polymer particles, composition containing same and treatment method
WO2006005822A1 (en) * 2004-06-08 2006-01-19 L'oreal Dispersion of ethylene polymer particles, composition containing same and treatment method
CN102898860A (en) * 2012-09-26 2013-01-30 大连理工大学 Two-photon fluorescent dye taking isoquinolinone as parent, preparation method thereof and application
CN102898860B (en) * 2012-09-26 2014-04-30 大连理工大学 Two-photon fluorescent dye taking isoquinolinone as parent, preparation method thereof and application
WO2021206059A1 (en) * 2020-04-07 2021-10-14 オリヱント化学工業株式会社 Colorant, master batch containing same, colored resin composition, and molded article
CN115443313A (en) * 2020-04-07 2022-12-06 东方化学工业株式会社 Coloring agent, master batch containing coloring agent, coloring resin composition and molded object

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