EP2373744A2 - Farbstoffe für polymerfärbung, ihre herstellung und verwendung - Google Patents

Farbstoffe für polymerfärbung, ihre herstellung und verwendung

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Publication number
EP2373744A2
EP2373744A2 EP09756742A EP09756742A EP2373744A2 EP 2373744 A2 EP2373744 A2 EP 2373744A2 EP 09756742 A EP09756742 A EP 09756742A EP 09756742 A EP09756742 A EP 09756742A EP 2373744 A2 EP2373744 A2 EP 2373744A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
amino
mono
carbamoyl
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09756742A
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English (en)
French (fr)
Inventor
Roxana Barbieru
Carsten Harfmann
Werner Russ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dystar Colours Distribution GmbH
Original Assignee
Dystar Colours Deutschland GmbH
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Filing date
Publication date
Application filed by Dystar Colours Deutschland GmbH filed Critical Dystar Colours Deutschland GmbH
Priority to EP09756742A priority Critical patent/EP2373744A2/de
Publication of EP2373744A2 publication Critical patent/EP2373744A2/de
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/005—Di-anthraquinonyl and derivative compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments

Definitions

  • Polymers can be colored with dyes in various ways.
  • One way is mass coloration of polymers whereby for example a pigment or a dye is mixed with the polymer and the polymer is melted to transport the dye into the polymer matrix.
  • Other processes involve the polymer being colored, or to be more precise dyed, by the dyes diffusing into the polymer from a solution or dispersion, examples being the dyeing of polymeric fibers composed of polyester, polyacrylonitrile, polyurethane, cellulose or polyamide for example with, for example, disperse dyes, cationic dyes, acid dyes, metallized dyes or reactive dyes.
  • the use of reactive dyes results in a covalent bond being formed between the dye and the substrate, conferring particularly high fastnesses on the dyeings/colorations.
  • Another way to color a polymer is to add the dye to the polymer's monomers or oligomers, before the polymer is formed or as it is being formed. Dyes capable of forming covalent bonds with the polymer scaffold may likewise result in colorations of high fastness being obtained. For this, the dyes used, or to be more precise their chromophores, have to be sufficiently stable under the conditions of the polymerization.
  • EP 0 423 068 A1 , EP 0648 817 A1 and JP 2003-43680 describe dianthraquinonyl dyes which meet the above-recited requirements to some extent.
  • the dyes mentioned give only a limited palette of hues and also only a limited degree of saturation when high bleed fastness is desired.
  • dianthraquinonyl dyes which are substituted by two triazine rings constitute useful dyes for the coloration of polyolefins and other substrates. They have high stability under application conditions, are readily soluble in the polymer, or miscible with suitable organic solvents, and afford highly transparent colorations having very good fastnesses.
  • the present invention thus provides dyes of formula (I)
  • X and T each independently represent a group of formula (1 ) to (3)
  • Y and Z each independently have one of the meanings G 1 or G 2 ;
  • G 1 represents Ar; cyclo-(C 3 -C 8 )-alkyl; (Ci-C 35 )-alkyl; (C 2 -C 35 )-alkyl interrupted by one or more hetero atoms; (Ci-C3 5 )-alkyl substituted by one or more of the substituents G 3 to G 6 ; or (C 2 -C 3 5)-alkyl interrupted by one or more hetero atoms and substituted by one or more of the substituents G 3 to G 6 ;
  • G 3 represents trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; Ar; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (Ci-C3 5 )-alkoxy; Ar-oxy; (C2-C3 5 )-acyl; Ar-carbonyl, (C2-C3 5 )-acyloxy; Ar-carbonyloxy; (C2-C3 5 )-acylamino; (Ci-C3 5 )-alkylsulfonylamino; Ar-sulfonylamino; Ar-carbonylamino; carbamoyl; N-monocyclo-(C3-C8)-alkyl- carbamoyl; N-mono-(Ci-C3 5 )-alkyl-carbamoyl; N,N-dicyclo-(C3-C8)-alkyl-carbamoyl; N,N-di
  • G 4 represents (C2-C3 5 )-alkoxy; (C2-C3 5 )-acyl; (C2-C3 5 )-acyloxy; (C2-C3 5 )-acylamino; (C 2 -C35)-alkylsulfonylamino; N-mono-(C2-C35)-alkyl-carbamoyl; N,N-Di-(C 2 -C 3 5)-alkyl- carbamoyl; N-mono-(C2-C35)-alkyl-N-monoarylcarbamoyl; (C 2 -C 3 5)-alkoxycarbonyl; mono-(C2-C35)-alkyl-amino; di-(C 2 -C35)-alkyl-amino; ITiOnO-(C 2 -C 3 S)- alkylmonoarylamino; N-mono-(C2-C35)-alkyl-sulfamo
  • G 5 represents cyclo-(C3-C8)-alkyl; heterocycloalkyl; (Ci-C3 5 )-alkoxy; (C2-C3 5 )-acyl; (C 2 -C 3 5)-acyloxy; (C 2 -C 3 5)-acylamino; (Ci-C 3 5)-alkylsulfonylamino; N-monocyclo-(C 3 - C 8 )-alkyl-carbamoyl; N-mono-(Ci-C 3 5)-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl- carbamoyl; N,N-di-(Ci-C 3 5)-alkyl-carbamoyl; N-monocyclo-(C3-C 8 )-alkyl-N-monoAr- carbamoyl; N-mono-(Ci-C 3
  • G 6 represents G 4 where the alkyl radical is substituted by a G 7 radical;
  • G 7 represents trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (Ci-C3 5 )-alkoxy; aryloxy; (C2-C3 5 )-acyl; arylcarbonyl, (C2-C3 5 )-acyloxy; arylcarbonyloxy; (C2-C3 5 )-acylamino; (Ci-C3 5 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C3-C8)-alkyl- carbamoyl; N-mono-(Ci-C35)-alkyl-carbamoyl; N,N-
  • G 2 represents (Ci-C3 5 )-alkyl or (C2-C3 5 )-alkyl interrupted by one or more heteroatoms, where the alkyl group is in each case substituted by a group of formula (4)
  • R 1 represents hydrogen; aryl; (Ci-C 35 )-alkyl; (C 2 -C 35 )-alkyl interrupted by one or more hetero atoms; (C 2 -C 35 )-acyl; cyclo(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 1 -C 35 )- alkoxycarbonyl; aryloxycarbonyl; (Ci-C 35 )-alkylsulfonyl, arylsulfonyl; monohydroxy-
  • (Ci-C 35 )-alkyl (Ci-C 35 )-alkyl; polyhydroxy-(C 2 -C 35 )-alkyl; (Ci-C 35 )-alkoxyalkyl or aryloxy-(Ci-C 35 )- alkyl;
  • R 2 represents hydrogen, (Ci-C 35 )-alkyl, singly or multiply oxygen-interrupted (C 2 -C 35 )- alkyl, aryl, aryl-(Ci-C 35 )-alkyl, (Ci-C 35 )-alkyl-aryl, aryloxy, (Ci-C 35 )-alkoxy, monohydroxy-(Ci-C 35 )-alkyl or polyhydroxy-(C 2 -C 35 )-alkyl; and has identical or different meanings within a molecule of formula (I);
  • v represents a number from 1 to 35;
  • t represents a rational number from 0 to 200 and has identical or different meanings within a molecule of formula (I);
  • R 3 and R 4 each independently represent hydrogen, (Ci-C 35 )-alkyl, singly or multiply oxygen-interrupted (C 2 -C 3 5)-alkyl, aryl, aryloxy, (Ci-C 3 5)-alkoxy, monohydroxy- (Ci-C 35 )-alkyl or polyhydroxy-(C 2 -C 35 )-alkyl; where R 3 and R 4 each have identical or different meanings within a molecule of formula (I); and where when R 3 and R 4 have different meanings within a molecule of formula (I) these different meanings are randomly distributed or regions of respectively identical meanings follow each other;
  • U represents hydrogen, hydroxyl, amino, mono-(Ci-C3 5 )-alkylamino, bis-(Ci-C3 5 )- alkylamino, (Ci-C 35 )-alkyl, aryl, aryloxy, (Ci-C 35 )-alkoxy, monohydroxy-(Ci-C 35 )-alkyl, polyhydroxy-(C 2 -C 35 )-alkyl or (Ci-C 35 )-alkyl-aryloxy;
  • Ar represents a group of formula (6) or (7)
  • R 5 to R 11 each independently have one of the meanings G 8 to G 11 or represent a group of formula (8)
  • W represents a group of formula (1 ), (3) or (9)
  • R 12 represents hydrogen, aryl, (Ci-C 35 )-alkyl, (C 2 -C 35 )-alkyl interrupted by one or more hetero atoms, (C 2 -C 3 5)-acyl; cyclo(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (Ci-C 35 )- alkoxycarbonyl; aryloxycarbonyl; (Ci-C 35 )-alkylsulfonyl, arylsulfonyl monohydroxy- (Ci-C 35 )-alkyl, polyhydroxy-(C 2 -C 35 )-alkyl, (Ci-C 35 )-alkoxyalkyl or aryloxy-(Ci-C 35 )- alkyl;
  • R 13 represents hydrogen, (Ci-Ci 5 )-alkyl, singly or multiply oxygen-interrupted (C 2 -Ci 5 )-alkyl, aryl, aryl-(Ci-Ci 5 )-alkyl, (Ci-Ci 5 )-alkyl-aryl, aryloxy, (Ci-Ci 5 )-alkoxy, monohydroxy-(Ci-Ci 5 )-alkyl or polyhydroxy-(C 2 -Ci 5 )-alkyl and can have identical or different meanings within a molecule of formula (I);
  • V represents hydrogen, hydroxyl, amino, mono-(Ci-C35)-alkylamino, bis-(Ci-C3 5 )- alkylamino, (Ci-C 35 )-alkyl, aryl, aryloxy, (Ci-C 35 )-alkoxy, monohydroxy-(Ci-C 35 )-alkyl, polyhydroxy-(C 2 -C 35 )-alkyl or (Ci-C 35 )-alkyl-aryloxy;
  • R 14 and R 15 each independently represent hydrogen, (Ci-C 35 )-alkyl, singly or multiply oxygen-interrupted (C2-C3 5 )-alkyl, aryl, aryloxy, (Ci-C3 5 )-alkoxy, monohydroxy-(Ci- C 35 )-alkyl or polyhydroxy-(C 2 -C 35 )alkyl and have identical or different meanings within a molecule of formula (I) and where when R 14 and R 15 have different meanings within a molecule of formula (I) these different meanings are randomly distributed or regions of respectively identical meanings follow each other;
  • r represents a rational number from 0 to 200 and has identical or different meanings within a molecule of formula (I);
  • G 8 represents hydrogen, (Ci-C 35 )-alkyl; thfluoromethyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (Ci-C3 5 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; cyclo-(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 2 -C 35 )-acyloxy; arylcarbonyloxy; (C 2 -C 3 5)-acylamino; (Ci-C 3 5)-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C3-C 8 )-alkyl-carbamoyl; N-mono-(Ci-
  • G 9 represents (C 2 -C 35 )-alkyl; (C 2 -C 35 )-alkoxy; (C 2 -C 35 )-acyl; (C 2 -C 35 )-acyloxy; (C 2 - C3 5 )-acylamino; (C 2 -C3 5 )-alkylsulfonylamino; N-mono-(C 2 -C35)-alkyl-carbamoyl; N 1 N- di-(C 2 -C3 5 )-alkyl-carbamoyl; N-mono-(C 2 -C35)-alkyl-N-monoarylcarbamoyl; (C 2 -Cs 5 )- alkoxycarbonyl; mono-(C 2 -C35)-alkyl-amino; di-(C 2 -C3 5 )-alkyl-amino; mono-(C 2 -C3 5 )- alky
  • G 10 represents (Ci-C 35 )-alkyl; cyclo-(C 3 -C 8 )-alkyl; heterocycloalkyl; (Ci-C 35 )-alkoxy; (C 2 -C3 5 )-acyl; cyclo-(C3-C8)-alkylcarbonyl; (C 2 -C3 5 )-acyloxy; (C 2 -C3 5 )-acylamino; (d- C3 5 )-alkylsulfonylamino; N-monocyclo-(C3-C8)-alkyl-carbamoyl; N-mono-(Ci-C3 5 )- alkyl-carbamoyl; N,N-dicyclo-(C3-C8)-alkyl-carbamoyl; N,N-di-(Ci-C3 5 )-alkyl- carbamoyl; N-monocyclo-(C3-C
  • G 11 represents G 9 where the alkyl radical is substituted by one or more G 7 substituents; where, in the groups G 7 to G 11 , aryl represents a group of formula (11 ) or (12)
  • R 16 to R 22 each independently represent the G 12 group; and G 12 represents hydrogen; (Ci-Ci 8 )-alkyl; monohydroxy-(Ci-Ci 8 )-alkyl; polyhydroxy- (C 2 -Ci 8 )-alkyl; (C 2 -Cis)-alkyl interrupted by one or more oxygen atoms; trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (Ci-Ci8)-alkoxy; (C2-Cis)-acyl; cyclo-(C3-C8)-alkylcarbonyl, (C2-Ci8)-acyloxy; (C2-Ci8)-acylamino; (Ci-Ci8)-alkylsulfonylamino; carbamoyl; N-monocyclo-(C3-C8)- alkyl-carbamoyl;
  • Y and Z do not both represent (Ci-C 3 5)-alkyl; a group of formula (6) where R 5 , R 6 and
  • R 7 each independently represent hydrogen, halogen, nitro, (Ci-C 3 5)-alkyl, (C1-C35)- alkoxy; mono-(Ci-C3 5 )-alkylamino, di-(Ci-C3 5 )-alkylamino, (Ci-C3 5 )-alkylthio, (C2-
  • R 4 , R 5 and R 6 each independently represent hydrogen, halogen, nitro, (Ci-C 35 )-alkyl, (Ci-C 35 )-alkoxy; mono-(Ci-C 35 )- alkylamino, di-(Ci-C 3 5)-alkylamino or (Ci-C 3 5)-alkylthio; and it is not the case that one of Y and Z represents (Ci-C3 5 )-alkyl and the other represents hydrogen; and when X and T both represent a group of formula (2),
  • Y and Z do not both represent (Ci-C 35 )-alkyl; (Ci-C 35 )-alkyl substituted by halogen, (Ci-C 35 )-alkylsulfonyl, substituted or unsubstituted benzenesulfonyl, or a group of formula (6) where R 5 , R 6 and R 7 independently represent hydrogen, halogen, (Cr C3 5 )-alkyl or (Ci-C3 5 )-alkoxy; a group of formula (6) where R 5 , R 6 and R 7 each independently represent hydrogen, halogen, nitro, cyano, (Ci-C 3 5)-alkyl, (C1-C35)- alkoxy or aryl; or substituted or unsubstituted benzoyl; and
  • Y and Z do not both represent a group of formula (6) where R 5 , R 6 and R 7 each independently represent hydrogen, halogen, nitro, (Ci-C 35 )-alkyl, (Ci-C 35 )-alkoxy; (C2-C3 5 )-acyl, benzoylamino or benzenesulfonylamino.
  • alkyl groups may be straight chain or branched and be for example methyl, ethyl, n-propyl, isopropyl, n-butyl or isobutyl, but also hexyl, such as n-hexyl, heptyl, such as n-heptyl, octyl, such as n-octyl and isooctyl, nonyl, such as n-nonyl, decyl, such as n-decyl, dodecyl, such as n-dodecyl, hexadecyl, such as n-hexadecyl, or octadecyl, such as n-octadecyl.
  • decyl such as n-decyl
  • dodecyl such as n-dodecyl
  • hexadecyl such as n-he
  • hetero atoms are oxygen, sulfur, sulfonyl, carboxyl and also the group -NR 23 , where R 23 represents
  • Cycloalkyl groups are in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Heterocycloalkyl has in particular 3 to 8 ring members and preferably represents pyrrolidine, piperidine, morpholine or piperazine.
  • Heteroaryl has in particular 5 or 6 ring members and is preferably pyridine, pyrimidine, pyhdazine, pyrazine, pyrrole, imidazole, pyrazole, 1 ,2,4-thiadiazole, 1 ,2,4- triazole, tetrazole, thiophene, thiazole, isothiazole, 1 ,3,4-thiadiazole, furan, oxazole or isoxazole.
  • Halogen is in particular fluorine, chlorine or bromine.
  • Y 1 and Z 1 each independently represent Ar 1 ; cyclo-(C 3 -C 8 )-alkyl; (Ci-C 35 )-alkyl; (C 2 - C 35 )-alkyl interrupted by one or more oxygen or sulfur atoms; (Ci-C 35 )-alkyl substituted by one or more G 13 to G 16 substituents; (C 2 -C 35 )-alkyl interrupted by one or more oxygen or sulfur atoms and substituted by one or more G 13 to G 16 substituents;
  • G 13 represents cyclo-(C 5 -C 6 )-alkyl; aryl; heterocycloalkyl having 5 or 6 ring members; halogen; cyano; hydroxyl; (Ci-Ci8)-alkoxy; aryloxy; (C2-Ci8)-acyl, arylcarbonyl; (C 2 - C 35 )-acylamino; (Ci-C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(Ci-C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )- alkyl-amino; di-(Ci-C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 - Cs
  • G 14 represents (C 2 -Cis)-alkoxy; (C 2 -Ci8)-acyl, (C 2 -C 35 )-acylamino; (C 2 -C 35 )- alkylsulfonylamino; mono-(C 2 -C 35 )-alkyl-amino; di-(C 2 -C 35 )-alkyl-amino; mono-(C 2 - C 35 )-alkylmonoaryl-amino; (C 2 -C 35 )-alkylthio; or (C 2 -C 35 )-alkylsulfonyl where the alkyl radical is interrupted by one or more heteroatoms;
  • G 15 represents cyclo-(C 5 -C 6 )-alkyl; aryl; heterocycloalkyl having 5 or 6 ring members; (Ci-Ci8)-alkoxy; (C 2 -Ci8)-acyl, (C 2 -C 35 )-acylamino; (Ci-C 35 )-alkylsulfonylamino; monocyclo-(C 3 -C8)-alkyl-amino; mono-(Ci-C 35 )-alkyl-amino; di(cyclo)-(C 3 -C8)-alkyl- amino; di-(Ci-C 35 )-alkyl-amino; monocyclo-(C 3 -C8)-alkylmonoarylamino; mono-(Ci- C 3 5)-alkylnnonoaryl-annino; (Ci-C 3 5)-alkylthio; or (Ci-C 3 5)-alkylsul
  • G » 16 represents G » 14 where the alkyl radical is substituted by a G 17 radical
  • G 17 represents trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (Ci-C 35 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; arylcarbonyl, (C 2 -C 35 )-acyloxy; arylcarbonyloxy; (C 2 -C 3 5)-acylamino; (Ci-C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl- carbamoyl; N-mono-(Ci-C 3 5)-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C8)-alkyl-carb
  • Ar 1 represents a group of formula (6a) or (7a)
  • R 5 to R 11 each independently represent hydrogen; (Ci-C 35 )-alkyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (Ci-C 35 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; cyclo-(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 2 -C 35 )-acyloxy; arylcarbonyloxy; (C2-C3 5 )-acylannino; (Ci-CssJ-alkylsulfonylannino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C3-C8)-alkyl-carbamoyl; N-mono-(Ci- C3 5
  • R 12 represents hydrogen, (C 2 -C 35 )-acyl; cyclo(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (Ci- C 35 )-alkylsulfonyl or arylsulfonyl;
  • R 13 represents hydrogen or (Ci-Ci 5 )-alkyl and has identical or different meanings within a molecule of formula (Ia);
  • x' represents a number from 1 to 10
  • V 1 represents hydrogen, (Ci-C 35 )-alkyl, aryl, aryloxy, (Ci-C 35 )-alkoxy or (Ci-C 35 )-alkyl- aryloxy;
  • Q 1 represents a group of formula (10a)
  • R 14 and R 15 each independently represent hydrogen or (Ci-C 35 )-alkyl and have identical or different meanings within a molecule of formula (Ia) and where when R 14 and R 15 have different meanings within a molecule of formula (Ia) these different meanings are randomly distributed or regions of respectively identical meanings follow each other;
  • r' represents a rational number from 0 to 100 and has identical or different meanings within a molecule of formula (Ia);
  • aryl is as defined above.
  • Y 1 and Z 1 each independently represent (C 8 -C 2 o)-alkyl; cyclopentyl; cyclohexyl or (Ci-C 4 )-alkyl substituted by a substituent selected from the group consisting of chlorine, cyclopentyl, cyclohexyl, (Ci-C 4 )- alkoxy, (C6-C2o)-alkylamino, (C6-C2o)-alkylamino interrupted by an S or an O, (CrC 4 )- alkylamino where the alkyl radical is substituted by (Ci-Ci8)-alkylsulfonyl whose alkyl group is interrupted by an NH group, (C6-C2o)-alkylthio, cyclohexyl-(Ci-C 4 )- alkylamino, phenyl-(Ci-C 4 )-alkoxy, phen
  • A represents -O-, -S-, -NH- or -NHCH 2 CH 2 -;
  • D represents hydrogen; (Ci-Ci 8 )-alkyl; a group of formula -O-(CH 2 ) n -SO 2 -(CH 2 ) m -OH where n and m each independently represent a whole number from 1 to 4; a group of formula -SO2-CH2CH2OH; and a group of formula (6a 1 )
  • R 13 represents hydrogen or methyl
  • V 1 represents hydrogen or (Ci-C 4 )-alkoxy; x" represents a number from 1 to 12;
  • Q 1 represents a group of formula (1Oa')
  • R 14 and R 15 each independently represent hydrogen or methyl; and r" represents a number from 0 to 10; or
  • Y 1 and Z 1 each independently represent phenyl; naphthalene; or phenyl substituted by phenyl, phenyl-(Ci-C 4 )-alkoxy or (Ci-C 35 )-alkylsulfonyl whose alkyl group is interrupted by an NH group or an NH group and 2 to 12 oxygen atoms.
  • dyes of formula (Ia) are the dyes of formulae (Ia1 ) to (Ia39)
  • Y 2 and Z 2 each independently represent (Ci-C 35 )-alkyl or (C 2 -C 35 )-alkyl interrupted by one or more heteroatoms, where in each case the alkyl group is substituted by a group of formula (4a) where
  • R 1 represents hydrogen or (Ci-C 35 )-alkyl
  • R 2 represents hydrogen or (Ci-C3 5 )-alkyl and has identical or different meanings within a molecule of formula (Ib); v' represents a number from 1 to 10;
  • S 1 represents a group of formula (5a):
  • R 3 and R 4 each independently represent hydrogen or (Ci-C 35 )-alkyl
  • R 4 each have identical or different meanings within a molecule of formula (Ib); and where when R 3 and R 4 have different meanings within a molecule of formula (Ib) these different meanings are randomly distributed or regions of respectively identical meanings follow each other; and
  • U 1 represents hydrogen, (Ci-C 3 5)-alkyl, aryl, aryloxy, (Ci-C 3 5)-alkoxy, or (C1-C35)- alkyl-aryloxy.
  • Y 2 and Z 2 each independently represent
  • R 1 represents hydrogen
  • R 3 and R 4 each independently represent hydrogen or methyl; where R 3 and R 4 each have identical or different meanings within a molecule of formula (Ib); and where when R 3 and R 4 have different meanings within a molecule of formula (Ib), these different meanings are randomly distributed or regions of respectively identical meanings follow each other; and U 1 represents (Ci-Ci2)-alkoxy or phenoxy substituted by (C 5 -Cio)-alkyl.
  • dyes of formula (Ib) are the dyes of formulae (Ib1 ) to (Ib4)
  • Y 1 and Z 1 each independently represent phenyl substituted by acetylamino, (Ci-C ⁇ J-alkyl, (CrC 4 )-alkoxy, trifluoromethyl or phenyl; (Ci-Cio)-alkyl; cyclohexyl; or (Ci-C 4 )-alkyl substituted by phenyl, (C 4 -Cis)- alkylamino, (Ci-C 4 )-alkoxy-phenoxy or by a group of formula (4a)
  • R 1 represents hydrogen
  • S 1 represents a group of formula (5a):
  • t' represents a number from 1 to 20;
  • R 3 and R 4 each independently represent hydrogen or methyl; where R 3 and R 4 each have identical or different meanings within a molecule of formula (Ic); and where when R 3 and R 4 have different meanings within a molecule of formula (Ic), these different meanings are randomly distributed or regions of respectively identical meanings follow each other; and
  • U 1 represents (Ci-Ci 2 )-alkoxy.
  • dyes of formula (Ic) are the dyes of formulae (Id ) to (Id 3):
  • Y 3 and Z 3 each independently represent naphthyl; (Ci-C 35 )-alkyl substituted by one or more of the G 18 substituents; or (C 2 -C 3 5)-alkyl interrupted by one or more oxygen or sulfur atoms and substituted by one or more of the G 18 substituents;
  • G 18 represents cyclo-(C 3 -C 8 )-alkyl; aryl; halogen; cyano; (Ci-C 3 5)-alkoxy; aryloxy; (C2-C3 5 )-acyl; arylcarbonyl, (C2-C3 5 )-acylamino; (Ci-CssJ-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; amino; monocyclo-(C3-C8)-alkyl-amino; mono- (Ci-C3 5 )-alkyl-amino; di(cyclo
  • Y 3 and Z 3 each independently represent naphthyl or (d-C ⁇ J-alkyl substituted by (Cio-C 2 o)-thioalkyl, (Cio-C 2 o)-alkylamino, chlorophenyl, phenyl-(Ci-C 4 )-alkoxy, fluorine, one, two or three chlorines or by a group of formula (4a)
  • R 1 represents hydrogen
  • S 1 represents a group of formula (5a):
  • R 3 and R 4 each independently represent hydrogen or methyl; where R 3 and R 4 each have identical or different meanings within a molecule of formula (Id); and where when R 3 and R 4 have different meanings within a molecule of formula (Id), these different meanings are randomly distributed or regions of respectively identical meanings follow each other; and U 1 represents (Ci-Ci 2 )-alkoxy.
  • dyes of formula (Id) are the dyes of formulae (Id1 ) to (Id15) (Id5) (Id6)
  • the dyes of formula (I) are obtainable by reacting the compound of formula (II)
  • reaction is particularly carried out at a temperature of 50-200 0 C, more preferably of 50-180 0 C, in the absence or presence of a base such as pyridine, pipehdine, sodium acetate, potassium carbonate or aluminum chloride and preferably in the absence of moisture and with a nitrogen stream.
  • the reaction medium used is preferably an inert solvent or a mixture of inert solvents.
  • Useful solvents include chlorinated solvents such as chlorobenzene or 1 ,2-dichlorobenzene, alcohols such as for example n-pentanol, 1 -methoxy-2-propanol, 2-ethylhexanol, 2-methyl-1 - butanol, isoamyl alcohol, benzyl alcohol, cyclohexanol, glycols and derivatives thereof such as for example ethylene glycol diethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, ethylene glycol, diethylene glycol monoethyl ether, dipropylene glycol, ethers such as for example dibutyl ether, diisobutyl ether, diisoamyl ether, di
  • the compounds of formulae (III) and (IV) can be reacted with the compound of formula (II) as a mixture.
  • the condensation reactions can be carried out in succession with or without intervening isolation of the intermediates formed.
  • Certain dyes of formula (I), for example those of formula (Ib), are preferably prepared by following an alternative, two-stage process.
  • the first step comprises reacting the compound of formula (II) with the compounds of formulae (III) and (IV) as indicated above, although the group Y or Z contains a functional group, for example a chlorine atom.
  • the dye obtained can then be reacted with a nucleophile to form further dyes of formula (I).
  • Suitable nucleophiles are for example amine and mercaptan derivatives. Such derivatives are known and commercially available.
  • Preferred amine derivatives are in particular the compounds sold by Huntsman, The Woodlands, TX, USA under the brand name of Jeffamine ® .
  • Examples are Jeffamine M-600, Jeffamine M-2005, Jeffamine M-2070, Jeffamine M-1000, Jeffamine D-230, Jeffamine D-400, Jeffamine D-2000, Jeffamine D-4000, Jeffamine HK-511 , Jeffamine ED-600, Jeffamine ED-900, Jeffamine ED-2003, Jeffamine ED-2001 , Jeffamine EDR- 148, Jeffamine EDR-176, Jeffamine T-403, Jeffamine M-3000, Jeffamine T-5000, Jeffamine XTJ-435 and Jeffamine XTJ-436.
  • the resulting dyes of formula (I) form statistical polymeric mixtures.
  • the compound of formula (II) is known as Colour Index dye C.I. Pigment Red 177 and commercially available.
  • the dyes of formula (I) can be isolated by filtration, extraction or evaporation and, if necessary, drying. However, they can also be used without further workup.
  • the dyes of formula (I) according to the present invention can be used directly for polymer coloration, or they are subjected to a finishing (conditioning) operation to convert them into a saleable dye preparation.
  • Finishing can be effected proceeding from a single dye of formula (I) or from a mixture of two or more dyes of formula (I) or mixtures of one or more of the dyes of formula (I) and dyes of other dye classes, for example pigments or solvent dyes, if appropriate with the assistance of auxiliaries, for example surface modifiers and dispersants, by dispersing, suspending or dissolving in a liquid or solid carrier material and also if appropriate standardizing to a desired color strength and a desired hue and if appropriate drying the preparation thus obtained.
  • auxiliaries for example surface modifiers and dispersants
  • Preparations comprising dyes of formula (I) may further comprise auxiliaries for modifying viscosity/flowability.
  • auxiliaries of this kind are described for example in US 6,605,126.
  • Preferred examples are ethylene glycols, propylene glycols, polyether polyols, polyester polyols, lactones and carbonic esters.
  • the present invention accordingly also provides dye preparations comprising one or more dyes of formula (I) and also one or more auxiliaries for modifying viscosity/flowability.
  • These dye preparations preferably contain one or more dyes of formula (I) in amounts of 5% to 100% by weight and one or more auxiliaries for modifying viscosity/flowability in amounts of 0% to 95% by weight, all based on the dye preparation.
  • the present invention further provides for the use of the dyes of formula (I) for coloring a polymer.
  • dyes of formula (I) can also be used in the form of masterbatches.
  • Masterbatches are dye concentrates consisting of carrier materials and colorants, the colorants being present in higher concentration than in the final use and the carrier materials being constituted such that they have compatibility with the materials to be colored.
  • the carrier materials used can be polymers, for example polyolefins, polyurethane, polyvinyl chloride, polyesters, polyamides, polycarbonates or polystyrene.
  • Preferred polymers are polyolefins, for example polyethylene or polypropylene and copolymers with polyolefins.
  • Useful carrier materials further include paraffin oils and polyglycols.
  • the dye masterbatches are characterized in particular in that they contain one or more dyes of formula (I) according to the present invention in amounts of 5% to 60% by weight and one or more carrier materials in amounts of 40% to 95% by weight.
  • the dyes of formula (I) have advantages in bleed/migration fastness in polyolefin mass coloration in particular, compared with commercially available solvent dyes. These advantages are particularly noticeable in the coloration of polypropylene, polypropylene copolymers and polypropylene blends. To achieve good bleed fastnesses for the colored polymer, it is preferable to use compounds of formula (I) that have sufficiently high molar mass.
  • Example 1 A mixture of 7.12 parts of the compound of formula (II), 75 parts of chlorobenzene and 8.73 parts of 3-cyclohexylpropionyl chloride (from Acros) is stirred under reflux at the boiling temperature of the mixture for 3 hours, cooled down and admixed with methanol. The isolated precipitate is stirred out with dilute aqueous sodium hydroxide solution, filtered off, washed neutral with water and dried to leave the dye of formula (Ia7).
  • Example 2 a) A mixture of 14.24 parts of compound of formula (II), 125 parts of 1 ,2- dichlorobenzene and 14.36 parts of 3-cyclohexanecarbonyl chloride (from Aldrich) is stirred at 180 0 C for 1 hour, cooled down and admixed with methanol. The isolated precipitate is stirred out with dilute aqueous sodium hydroxide solution, filtered off, washed neutral with water and dried to leave the dye of formula (Ia24).
  • Example 8 a A mixture of 7.12 parts of compound of formula (II), 75 parts of chlorobenzene and 8.38 parts of 3-cyclopentylpropionyl chloride (from Aldrich) is stirred 180 0 C for 2 hours, cooled down and filtered. The isolated precipitate is purified with warm methanol and dried to leave the dye of formula (Ia8).

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
EP09756742A 2008-12-04 2009-11-24 Farbstoffe für polymerfärbung, ihre herstellung und verwendung Withdrawn EP2373744A2 (de)

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EP08170681 2008-12-04
PCT/EP2009/065681 WO2010063606A2 (en) 2008-12-04 2009-11-24 Dyes for polymer coloration, their preparation and their use
EP09756742A EP2373744A2 (de) 2008-12-04 2009-11-24 Farbstoffe für polymerfärbung, ihre herstellung und verwendung

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JPS491289B1 (de) * 1970-12-04 1974-01-12
BE790055A (fr) * 1971-10-14 1973-04-13 Ciba Geigy Procede de preparation de 1,1'-dianthraquinonyles
US5238984A (en) * 1989-10-10 1993-08-24 Ciba-Geigy Corporation Dianthraquinonyl compounds
EP0423068B1 (de) * 1989-10-10 1994-11-30 Ciba-Geigy Ag Neue Dianthrachinonylverbindungen
DE59408909D1 (de) * 1993-10-13 1999-12-16 Ciba Sc Holding Ag Neue Fluoreszenzfarbstoffe
DE59802184D1 (de) * 1997-02-13 2002-01-03 Bayer Ag Verbrückte Anthrachinone
JP4089180B2 (ja) * 2001-07-30 2008-05-28 東洋インキ製造株式会社 カラーフィルタ用着色組成物およびカラーフィルタ
JP2004067714A (ja) * 2002-08-01 2004-03-04 Toray Ind Inc 顔料分散液、着色剤組成物、カラーフィルター、及び液晶表示パネル
TW200613452A (en) * 2004-06-25 2006-05-01 Clariant Int Ltd Bridged bisanthraquinone dye derivatives
JP5114020B2 (ja) * 2006-05-26 2013-01-09 東洋インキＳｃホールディングス株式会社 顔料組成物の製造方法
JP2009542876A (ja) * 2006-07-10 2009-12-03 チバ ホールディング インコーポレーテッド 有機材料を光から保護する方法
JP5497991B2 (ja) * 2008-03-13 2014-05-21 富士フイルム株式会社 顔料微粒子の製造方法

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WO2010063606A2 (en) 2010-06-10

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