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WO2003010229A1 - Procede de coloration en masse de materiaux synthetiques - Google Patents

Procede de coloration en masse de materiaux synthetiques Download PDF

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Publication number
WO2003010229A1
WO2003010229A1 PCT/EP2002/007987 EP0207987W WO03010229A1 WO 2003010229 A1 WO2003010229 A1 WO 2003010229A1 EP 0207987 W EP0207987 W EP 0207987W WO 03010229 A1 WO03010229 A1 WO 03010229A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen
carboxylic acid
alkylthio
arylthio
alkoxy
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.)
Ceased
Application number
PCT/EP2002/007987
Other languages
English (en)
Inventor
Peter Aeschlimann
Leonhard Feiler
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to EP02767226A priority Critical patent/EP1409578A1/fr
Priority to JP2003515587A priority patent/JP2004536200A/ja
Priority to US10/484,355 priority patent/US20040231073A1/en
Publication of WO2003010229A1 publication Critical patent/WO2003010229A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/06—Dyes
    • 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
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C08K5/3417—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
    • C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
    • 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
    • C09B57/06—Naphtholactam dyes

Definitions

  • the present invention relates to a method of mass-colouring synthetic materials with dyes based on naphtholactam.
  • the present invention accordingly relates to a method of mass-colouring synthetic materials based on terpolymers of acrylonitrile, butadiene and styrene (ABS terpolymers), which comprises using at least one dye of formula
  • R 2 is hydrogen, a carboxylic acid group or a carboxylic acid ester group
  • R 3 is hydrogen, halogen, alkoxy, aryloxy, alkylthio, arylthio, a carboxylic acid group or a carboxylic acid ester group, and
  • W is a radical of formula
  • R 4 , R 8 and Rn are each independently of the others hydrogen, alkyl, alkoxy, aryloxy, alkylthio or arylthio,
  • R 5 , R 7 and R 10 are each independently of the others hydrogen, alkoxy, aryloxy, alkylthio, arylthio, a carboxylic acid group or a carboxylic acid ester group
  • R 6 and R 9 are each independently of the other cyano, -CONR 12 R 13 or -SO 2 R 14 , wherein R ⁇ 2 and R 13 are each independently of the other hydrogen or C C 4 alkyl and R 1 is C 1 -C 4 alkyl, and
  • X is -NH-, -O- or -S-, or
  • R 5 and R 5 ' together form a phenyl or naphthyl radical.
  • R 4 , R 8 and Rn as alkyl are each independently of the others preferably C C alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
  • R 12 , R 13 and R 14 as C C 4 alkyl are each independently of the others methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
  • R 1( R 3 , R 4 , R 5 , R 7 , Rs, R 1 0 and Rn as alkoxy are each independently of the others preferably C ⁇ -C alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, it being possible for the carbon chain in alkoxy to be interrupted one or more times by oxygen.
  • Ri, R 3 , R , R 5 , R 7 , R 8 , R 1 0 and Rn as alkylthio are each independently of the others preferably CrC alkylthio, for example methylthio, ethylthio, propylthio or butylthio.
  • Ri, R3, R , R5, R 7 , Rs, R10 and Rn as aryloxy are each independently of the others preferably C 6 -C- ⁇ 2 aryloxy, for example phenoxy or naphthyloxy.
  • R , R3, R , R5, R7, Rs, R 1 0 and R as arylthio are each independently of the others preferably C 6 -C 12 arylthio, for example phenylthio or naphthylthio.
  • phenyl radicals in phenoxy can be unsubstituted or substituted by methyl, chlorine, d-C 4 alkylthio and/or by arylthio.
  • naphthyl radicals in naphthyloxy can be unsubstituted or substituted by methyl, chlorine, C ⁇ -C 4 alkylthio and/or by arylthio.
  • Halogen is, for example, chlorine or iodine and preferably bromine.
  • a carboxylic acid group is to be understood as being a -(CH 2 ) n -COOH radical wherein n is a number from 0 to 3. n is preferably 0.
  • a carboxylic acid ester group is preferably a -(CH ⁇ n-COOCrCealkyl radical wherein n is a number from 0 to 3. n is preferably 0.
  • C C ⁇ Alkyl is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert- butyl, pentyl or hexyl.
  • Ri is preferably hydrogen, halogen or C C 4 alkylthio.
  • R 2 is preferably hydrogen, -COOH or -COOd-Cealkyl.
  • R 3 is preferably hydrogen, -COOH or -COOC C 6 alkyl.
  • R 4 is preferably hydrogen, CrC 4 alkyl, C C 4 alkoxy, C 1 -C 4 alkylthio, C 6 -C 12 aryloxy or C 6 -C 12 - arylthio.
  • R 5 is preferably hydrogen, -COOH, -COOC ⁇ C-ealkyl, C C alkyl, C C alkoxy, C ⁇ -C 4 alkylthio, C 6 -C 12 aryloxy or C 6 -C 12 arylthio.
  • R 6 is preferably cyano.
  • R 9 is preferably cyano.
  • X is preferably -O- and -S-.
  • R 12 is hydrogen, a carboxylic acid group or a carboxylic acid ester group
  • R 13 is hydrogen or C 6 -C ⁇ 2 aryIthio
  • Rn is a carboxylic acid group or a carboxylic acid ester group
  • R 15 and R 16 are each independently of the other hydrogen, CrC 4 alkoxy, C 6 -C 12 aryloxy,
  • Rl7 hydrogen, a carboxylic acid group or a carboxylic acid ester group, R-I8 s hydrogen or halogen, Rl9 s hydrogen,
  • X is -O- or -S-.
  • the dyes of formula (1) used in accordance with the invention are known, for example, from DE-A-2 736914, DE-A-2607 869, DE-A-2 724 566 and DE-A-2724 567 or can be prepared according to generally known methods.
  • the dyes of formula (1) used in accordance with the invention are prepared, for example, by condensing a naphtholactam compound of formula wherein
  • R-i, R 2 and R 3 are as defined for formula (1), in the presence of an acid condensation agent, preferably phosphorus oxychloride, with a methylene-active compound of formula
  • the compounds of formulae (50) to (52) are known or can be prepared according to generally known methods.
  • the present invention relates also to the use of the dyes of formula (1) in the production of coloured plastics or polymeric colour particles, which comprises mixing together a high molecular weight organic material, which consists wholly or predominantly of ABS terpolymers or comprises ABS terpolymers, and a tinctorially effective amount of at least one dye of formula (1).
  • the colouring of such high molecular weight organic substances with the dye of formula (1) is carried out, for example, by mixing such a dye into those substrates using roll mills, mixing apparatus or grinding apparatus, with the result that the dye is dissolved or finely dispersed in the high molecular weight material.
  • the high molecular weight organic material with the admixed dye is then processed using processes known perse, for example calendering, compression moulding, extrusion, coating, spinning, casting or injection moulding, whereby the coloured material acquires its final form.
  • the admixing of the dye is carried out immediately prior to the actual processing step, for example by continuously feeding a solid, for example pulverulent, dye and, at the same time, a granulated or pulverulent high molecular weight organic material, and optionally also additional ingredients, e.g. additives, directly into the intake zone of an extruder, where mixing takes place just before processing.
  • a solid for example pulverulent, dye
  • a granulated or pulverulent high molecular weight organic material e.g. additives
  • additional ingredients e.g. additives
  • plasticisers In order to produce non-rigid mouldings or to reduce their brittleness, it is often desirable to incorporate so-called plasticisers into the high molecular weight compounds prior to shaping.
  • plasticisers for example, esters of phosphoric acid, phthalic acid or sebacic acid.
  • the plasticisers may be incorporated into the polymers before or after the incorporation of the colorant. It is also possible, in order to achieve different shades of colour, to add to the high molecular weight organic materials, in addition to the dye of formula (1), also further dyes, pigments or other colorants in any desired amounts, optionally together with further additives, e.g. fillers or siccatives.
  • thermoplastic plastics especially in the form of fibres or mouldings.
  • ABS terpolymer to be coloured comprises repeating monomer units of the formulae
  • the dyes used in accordance with the invention impart to the mentioned materials tinctorially strong, level red or orange colour shades having very good in-use fastness properties, especially good light fastness and good thermostability.
  • ABS acrylamide-butadiene-styrene terpolymer
  • the homogeneous mixture is extruded in an extruder (twin screw 25 mm from Collin,
  • the resulting yellowish-red-coloured ABS granules are stable to high temperatures and have good allround fastness properties, especially very good light fastness and high-temperature light fastness properties.
  • ABS acrylamide-butadiene-styrene terpolymer
  • the homogenous mixture is extruded in an extruder (twin screw 25 mm from Collin,
  • the resulting orange- to yellowish-red-coloured ABS granules are stable to high temperatures and have good allround fastness properties, especially very good light fastness and high-temperature light fastness properties.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Abstract

L'invention concerne un procédé de coloration en masse de matériaux synthétiques constitués de terpolymères d'acrylonitrile, de butadiène et de styrène, qui consiste à utiliser au moins un colorant de formule (1) dans laquelle R1 représente un hydrogène, un halogène, un groupe alcoxy, aryloxy, alkylthio ou arylthio, R2 représente un hydrogène, un groupe acide carboxylique ou ester d'acide carboxylique, R3 représente un hydrogène, un halogène, un groupe alcoxy, aryloxy, alkylthio, arylthio, un groupe acide carboxylique ou ester d'acide carboxylique, et W représente un radical de formules (2), (3), (4), (5), (6), dans lesquelles R4, R8 et R11 représentent, d'une manière indépendante les uns des autres, un hydrogène, un groupe alkyle, alcoxy, aryloxy, alkylthio ou arylthio, R5, R7 et R10 représentent, d'une manière indépendante les uns des autres, un hydrogène, un groupe alcoxy, aryloxy, alkylthio, arylthio, un groupe acide carboxylique ou ester d'acide carboxylique, R6 et R9 représentent, d'une manière indépendante l'un de l'autre un groupe cyano, -CONR12R13 ou -SO2R14, dans lesquels R12 et R13 représentent, d'une manière indépendante l'un de l'autre, un hydrogène ou un groupe C1-C4alkyle et R14 représente un groupe C1-C4alkyle, et X représente un groupe -NH-, -0- ou -S-, ou R5 et R5' forment ensemble un groupe phényle ou naphtyle.
PCT/EP2002/007987 2001-07-26 2002-07-18 Procede de coloration en masse de materiaux synthetiques Ceased WO2003010229A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP02767226A EP1409578A1 (fr) 2001-07-26 2002-07-18 Procede de coloration en masse de materiaux synthetiques
JP2003515587A JP2004536200A (ja) 2001-07-26 2002-07-18 合成材料を練り込み着色する方法
US10/484,355 US20040231073A1 (en) 2001-07-26 2002-07-18 Method of mass-colouring synthetic materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP01810736.7 2001-07-26
EP01810736 2001-07-26

Publications (1)

Publication Number Publication Date
WO2003010229A1 true WO2003010229A1 (fr) 2003-02-06

Family

ID=8184054

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/007987 Ceased WO2003010229A1 (fr) 2001-07-26 2002-07-18 Procede de coloration en masse de materiaux synthetiques

Country Status (4)

Country Link
US (1) US20040231073A1 (fr)
EP (1) EP1409578A1 (fr)
JP (1) JP2004536200A (fr)
WO (1) WO2003010229A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2415055A1 (de) * 1974-03-28 1975-10-02 Bayer Ag Metallkomplexfarbstoffe
US4009165A (en) * 1974-06-11 1977-02-22 Basf Aktiengesellschaft Naphtholactam dyes
US4256896A (en) * 1976-06-01 1981-03-17 Ciba-Geigy Aktiengesellschaft Naphtholactam dyestuffs

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH614229A5 (fr) * 1975-02-28 1979-11-15 Ciba Geigy Ag
US4180665A (en) * 1976-06-01 1979-12-25 Ciba-Geigy Aktiengesellschaft Substituted 3-benz(cd)indol-2-(1H)-ylidene-furo[2,3-b]quinoxalin-2(3H)one dyestuffs
US4246410A (en) * 1976-06-01 1981-01-20 Ciba -Geigy Aktiengesellschaft Naphtholactam dyestuffs
LU75606A1 (fr) * 1976-08-17 1978-04-13

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2415055A1 (de) * 1974-03-28 1975-10-02 Bayer Ag Metallkomplexfarbstoffe
US4009165A (en) * 1974-06-11 1977-02-22 Basf Aktiengesellschaft Naphtholactam dyes
US4256896A (en) * 1976-06-01 1981-03-17 Ciba-Geigy Aktiengesellschaft Naphtholactam dyestuffs

Also Published As

Publication number Publication date
EP1409578A1 (fr) 2004-04-21
JP2004536200A (ja) 2004-12-02
US20040231073A1 (en) 2004-11-25

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