US3561911A - Process for the dyeing of shaped articles made of aromatic polyesters of cellulose triacetate - Google Patents

Process for the dyeing of shaped articles made of aromatic polyesters of cellulose triacetate Download PDF

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US3561911A
US3561911A US689769A US3561911DA US3561911A US 3561911 A US3561911 A US 3561911A US 689769 A US689769 A US 689769A US 3561911D A US3561911D A US 3561911DA US 3561911 A US3561911 A US 3561911A
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Prior art keywords
dyeing
cellulose triacetate
aromatic polyesters
naphthalene
formula
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US689769A
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Karl Fuhr
Hans Rudolph
Ernst Robert Fritze
Otto Schneider
Walter Hees
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Bayer AG
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Bayer AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/36—Material containing ester groups using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/38—Preparing azo dyes on the material

Definitions

  • the present invention relates to a process for the dyeing of shaped articles made of aromatic polyesters or cellulose triacetate in an aqueous medium with disperse or ingrain dyestuffs. More particularly it concerns a process wherein the dyeing is carried out in the presenc of carriers which are naphthalene derivatives of the general formula R CH OR (I) in which R, represent a naphthyl radical or tetrahydronaphthyl radical which may be substituted by alkyl groups with 1-4 carbon atoms and/or by halogen atoms and R stands for an alkyl or acyl radical with 1-4 carbon atoms.
  • carriers which are naphthalene derivatives of the general formula R CH OR (I) in which R, represent a naphthyl radical or tetrahydronaphthyl radical which may be substituted by alkyl groups with 1-4 carbon atoms and/or by halogen atoms and R stands for an alkyl or acy
  • Compounds of the Formula I can be obtained in a simple manner, for example, from chloromethyl-naphthalenes or 1,2,3,4 tetrahydro-6-chloromethyl-naphthalenes by reaction with alcoholates or salts of carboxylic acids in an alcoholic solution.
  • naphthalene derivatives are particularly effective in the Formula I of which R stands for a radical which contains only one or two carbon atoms, for example 1-methoxymethyl-naphthalene, l-ethoxymethyl naphthalene, 1,2,3,4-tetrahydro-6-methoxymethyl naphthalene as well as the formyl and acetyl derivatives of 1-hydroxymethyl-naphthalene and 1,2,3,4 tetrahydro-6-hydroxymethyl-naphthalene.
  • R stands for a radical which contains only one or two carbon atoms
  • the process according to the invention enables shaped articles, for example, filaments, fibres, foils and fabrics Patented Feb. 9, 1971 of aromatic polyesters, e.g. those of polyethylene glycol terephthalate or condensation products obtained from terephthalic acid and 1,4-bis-hydroxymethyl-cyclohexane, or of cellulose triacetate to be dyed with disperse or ingrain dyestuffs in deep shades with a substantial acceleration of the dyestuff absorption.
  • aromatic polyesters e.g. those of polyethylene glycol terephthalate or condensation products obtained from terephthalic acid and 1,4-bis-hydroxymethyl-cyclohexane
  • cellulose triacetate e.g. those of polyethylene glycol terephthalate or condensation products obtained from terephthalic acid and 1,4-bis-hydroxymethyl-cyclohexane
  • the compounds of the Formula I are water insoluble, care'must be taken that they are present in the dyebath in emulsified form.
  • they can be added in the form of solutions in organic solvents, e.g. isopropyl alcohol, to the dyebaths containing an emulsifier or an emulsifier mixture.
  • organic solvents e.g. isopropyl alcohol
  • mixtures of compounds of the Formula I, optionally in combination with known carriers, and emulsifiers to the dyebath.
  • Suitable emulsifiers are primarily anionactive and/ or non-ionic compounds. In general amounts of emulsifiers of 15 to 30%, preferably 25%, referred to the weight of the used compounds of the Formula I or the used mixtures of the compounds of the Formula I and other carriers have proved.
  • Disperse and ingrain dystuifs which are suitable for the process according to the invention are described, for
  • the dyeing of the shaped articles made of aromatic polyesters or cellulose triacetate with dispersion or ingrain dyestuffs in the presence of the compounds of the Formula I is usually performed in a long bath at temperatures of about C.
  • the compounds of the Formula I are liquid, even at temperatures below 0 C. Difficulties as are encountered in the use of crystalline products do therefore not occur. Further remarkable features are the low steam volatility, the absence of annoyance through odour and the nontoxicity.
  • Fibres of polyethylene glycol terephthalate are introduced in a liquor ratio of 1:40 into an aqueous bath containing, per litre, 0.75 g. of the disperse dyestuif l-hydroxy-4-(p-tolylamino)-anthraquin0ne and 2 g. sodium oleyl-methyl-tauride.
  • 4 g. 1-methoxymethyl-naphthalene which were previously mixed with hot isopropyl alcohol are then added with stirring and dyeing is carried out at 96-98 C. for 2 hours. The material is subsequently rinsed and dried. A blue dyeing of very good fastness to light is obtained.
  • Fibres of cellulose triacetate are introduced in a liquor ratio of 1:40 into an aqueous bath containing, per litre, 0.75 g. of the disperse dyestuff 1-amino-4-hydroxy-2- bromo-anthraquinone and 2 g. sodium dina'phthyl-me'thane disulphonate. 4 g. 1-methoxymethyl-naphthal ne which were previously mixed with hot isopropyl alcoho are added with stirring. After the usual dyeing time of 2 hours, a red dyeing of very good fastness to light is obtained.
  • EXAMPLE 3 The procedure is as described in Example 1, but with the difference that the carrier is applied in the form of the mixture described below, which is added to the hot dyebath in an amount of g. per litre.
  • the mixture consists of 80 parts 1-methoxymethyl-naphthalene, 12 parts of the monoethanolamine salt of tetrapropylene-benzenesulphonic acid and 8 parts of the reaction product of one mole o-benzylphenylphenol with 16 moles ethylene oxide. A deep blue dyeing of very good fastness to light is obtained.
  • EXAMPLE 4 The procedure is as described in Example 1, but with the difference that the carrier is applied in the form of the mixture described below, which is added to the hot dyebath in an amount of 5 g. per litre.
  • the mixture consists of 40 parts 1-methoxymethyl-naphthalene, 40 parts 1-acetoxymethyl-naphthalene, 12 parts of the monoethanolamine salt of tetrapropylene-benzenesulphonic acid and 8 parts of the reaction product of one mole o-benzylphenylphenol with 16 moles ethylene oxide. A deep blue dyeing of very good fastness to light is obtained.
  • EXAMPLE 5 The procedure is as described in Example 1, but with the difference that the carrier is applied in the form of the mixture described below, which is added to the hot dyebath in an amount of 5 g. per litre.
  • the mixture consists of 40 parts 1-methoxymethyl-naphthalene, 20 parts benzylphenyl ether, 20 parts diphenyl ether, 12 parts of the monoethanolamine salt of tetrapropylene-benzenesulphonic acid and 8 parts of the reaction product of one mole o-benzylphenylphenol with 16 moles ethylene oxide. A deep blue dyeing of very good fastness to light is obtained.
  • Process according to claim 1 characterised in that as carrier is used a mixture of 1-methoxymethyl-naphthalene and 1-acetoxymethyl-naphthalene.
  • Process according to claim 1 characterised in that as carrier is used a mixture of 1-methoxymethyl-naphtha lene and diphenyl ether.
  • Process according to claim 1 characterised in that as carrier is used a mixture of l-methoxymethyl-naphthalene, benzyl-phenyl ether and diphenyl ether.
  • An aqueous dyeing bath adapted for use in dyeing shaped articles made of aromatic polyesters or cellulose triacetate containing disperse or ingrain dyestuffs and carriers characterised in that as a carrier naphthalene derivatives of the formula R CH OR References Cited FOREIGN PATENTS 915,342 l/l963 Great Britain 8175 985,143 3/1965 Great Britain 8173 1,000,407 8/1965 Great Britain -173 GEORGE F. LESMES, Primary Examiner T. J. HERBERT, 111., Assistant Examiner US. Cl. X.R. 8-l73, 179

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)

Abstract

A PROCESS AND COMPOSITION FOR DYEING AROMATIC POLYESTERS OR CELLULOSE TRIACETATE IN AN AQUEOUS BATH WITH DISPERSE OR INGRAIN DYESTUFF WHEREIN AN IMPROVED CARRIER IS USED COMPRISING NAPHTHALENE DERIVATIVES OF THE FORMULA

R1CH2OR2

WHERE R1 IS NAPHTHYL OR TETRAHYDRO NAPHTHYL WHICH MAY CONTAIN SUBSTITUENTS AND R2 IS ALKYL OR ACYL.

Description

United States Patent Oifice PROCESS FOR THE DYEING OF SHAPED ARTI- CLES MADE OF AROMATIC POLYESTERS OF CELLULOSE TRIACETATE Karl Fuhr and Hans Rudolph, Krefeld-Bockum, Ernst- Robert Fritze and Otto Schneider, Cologne-Flittard, and Walter Hees, Cologne-Hohenberg, Germany, assignors to Farbenfabriken Bayer Aktiengesellschaft, Le'verkusen, Germany, a corporation of Germany No Drawing. Filed Dec. 12, 1967, Ser. No. 689,769 Claims priority, application Germany, Dec. 17, 1966,
Int. Cl. D06p 3/54 US. Cl. 8-4 6 Claims ABSTRACT OF THE DISCLOSURE A process and composition for dyeing aromatic polyesters or cellulose triacetate in an aqueous bath with disperse or ingrain dyestuif 'wherein an improved carrier is used comprising naphthalene derivatives of the formula R CH OR where R is naphthyl or tetrahydro naphthyl which may contain substituents and R is alkyl or acyl.
The present invention relates to a process for the dyeing of shaped articles made of aromatic polyesters or cellulose triacetate in an aqueous medium with disperse or ingrain dyestuffs. More particularly it concerns a process wherein the dyeing is carried out in the presenc of carriers which are naphthalene derivatives of the general formula R CH OR (I) in which R, represent a naphthyl radical or tetrahydronaphthyl radical which may be substituted by alkyl groups with 1-4 carbon atoms and/or by halogen atoms and R stands for an alkyl or acyl radical with 1-4 carbon atoms.
Examples of the compounds of Formula -I are:
Compounds of the Formula I can be obtained in a simple manner, for example, from chloromethyl-naphthalenes or 1,2,3,4 tetrahydro-6-chloromethyl-naphthalenes by reaction with alcoholates or salts of carboxylic acids in an alcoholic solution.
Within the scope of the process according to the invention those naphthalene derivatives are particularly effective in the Formula I of which R stands for a radical which contains only one or two carbon atoms, for example 1-methoxymethyl-naphthalene, l-ethoxymethyl naphthalene, 1,2,3,4-tetrahydro-6-methoxymethyl naphthalene as well as the formyl and acetyl derivatives of 1-hydroxymethyl-naphthalene and 1,2,3,4 tetrahydro-6-hydroxymethyl-naphthalene.
The process according to the invention enables shaped articles, for example, filaments, fibres, foils and fabrics Patented Feb. 9, 1971 of aromatic polyesters, e.g. those of polyethylene glycol terephthalate or condensation products obtained from terephthalic acid and 1,4-bis-hydroxymethyl-cyclohexane, or of cellulose triacetate to be dyed with disperse or ingrain dyestuffs in deep shades with a substantial acceleration of the dyestuff absorption.
The necessary amounts of compounds of the Formula I to be used according to the invention can easily be established for each case by preliminary experiments. In general dependant upon the desired depth of the dyeing by applying the usual liquor ratios of 1:4-40 amounts of l-5 g. per litre of dyebath will prove sufiicient.
It is also possible to use compounds of the Formula I in combination with known carriers, such as aromatic hydrocarbons, halogenated hydrocarbons, phenols, esters and ethers, for example, l-methyl-nap-hthalene, trichlorobenzene, o-hydroxydiphenyl, benzoic acid phenyl ester, benzylphenyl ether and diphenyl ether.
Since the compounds of the Formula I are water insoluble, care'must be taken that they are present in the dyebath in emulsified form. For this purpose, they can be added in the form of solutions in organic solvents, e.g. isopropyl alcohol, to the dyebaths containing an emulsifier or an emulsifier mixture. However, it is also possible to add mixtures of compounds of the Formula I, optionally in combination with known carriers, and emulsifiers to the dyebath. Suitable emulsifiers are primarily anionactive and/ or non-ionic compounds. In general amounts of emulsifiers of 15 to 30%, preferably 25%, referred to the weight of the used compounds of the Formula I or the used mixtures of the compounds of the Formula I and other carriers have proved.
Disperse and ingrain dystuifs which are suitable for the process according to the invention are described, for
' example, in Diserens Die neuesten Fortschritte in der Anwendung der 'Farbstoife, vol. 2, 2nd ed. (1949) et seq. and vol. 1, 2nd ed. (1946), pp. 304 et seq.
The dyeing of the shaped articles made of aromatic polyesters or cellulose triacetate with dispersion or ingrain dyestuffs in the presence of the compounds of the Formula I is usually performed in a long bath at temperatures of about C.
The compounds of the Formula I are liquid, even at temperatures below 0 C. Difficulties as are encountered in the use of crystalline products do therefore not occur. Further remarkable features are the low steam volatility, the absence of annoyance through odour and the nontoxicity.
The parts given in the examples are parts by weight.
EXAMPLE 1 Fibres of polyethylene glycol terephthalate are introduced in a liquor ratio of 1:40 into an aqueous bath containing, per litre, 0.75 g. of the disperse dyestuif l-hydroxy-4-(p-tolylamino)-anthraquin0ne and 2 g. sodium oleyl-methyl-tauride. 4 g. 1-methoxymethyl-naphthalene which were previously mixed with hot isopropyl alcohol are then added with stirring and dyeing is carried out at 96-98 C. for 2 hours. The material is subsequently rinsed and dried. A blue dyeing of very good fastness to light is obtained.
EXAMPLE 2 Fibres of cellulose triacetate are introduced in a liquor ratio of 1:40 into an aqueous bath containing, per litre, 0.75 g. of the disperse dyestuff 1-amino-4-hydroxy-2- bromo-anthraquinone and 2 g. sodium dina'phthyl-me'thane disulphonate. 4 g. 1-methoxymethyl-naphthal ne which were previously mixed with hot isopropyl alcoho are added with stirring. After the usual dyeing time of 2 hours, a red dyeing of very good fastness to light is obtained.
3 EXAMPLE 3 The procedure is as described in Example 1, but with the difference that the carrier is applied in the form of the mixture described below, which is added to the hot dyebath in an amount of g. per litre. The mixture consists of 80 parts 1-methoxymethyl-naphthalene, 12 parts of the monoethanolamine salt of tetrapropylene-benzenesulphonic acid and 8 parts of the reaction product of one mole o-benzylphenylphenol with 16 moles ethylene oxide. A deep blue dyeing of very good fastness to light is obtained.
EXAMPLE 4 The procedure is as described in Example 1, but with the difference that the carrier is applied in the form of the mixture described below, which is added to the hot dyebath in an amount of 5 g. per litre. The mixture consists of 40 parts 1-methoxymethyl-naphthalene, 40 parts 1-acetoxymethyl-naphthalene, 12 parts of the monoethanolamine salt of tetrapropylene-benzenesulphonic acid and 8 parts of the reaction product of one mole o-benzylphenylphenol with 16 moles ethylene oxide. A deep blue dyeing of very good fastness to light is obtained.
EXAMPLE 5 The procedure is as described in Example 1, but with the difference that the carrier is applied in the form of the mixture described below, which is added to the hot dyebath in an amount of 5 g. per litre. The mixture consists of 40 parts 1-methoxymethyl-naphthalene, 20 parts benzylphenyl ether, 20 parts diphenyl ether, 12 parts of the monoethanolamine salt of tetrapropylene-benzenesulphonic acid and 8 parts of the reaction product of one mole o-benzylphenylphenol with 16 moles ethylene oxide. A deep blue dyeing of very good fastness to light is obtained.
We claim:
1. Process for the dyeing of shaped articles made of aromatic polyesters or cellulose triacetate in an aqueous bath with disperse or ingrain dyestuffs in the presence of carriers, characterised in that as carrier naphthalene derivatives of the formula R CH OR 4 in which R denotes a naphthyl radical or tetrahydronaphthyl radical which may be substituted by alkyl groups with 1-4 carbon atoms and/or by halogen atoms and R stands for an alkyl or alkanoyl radical with 1-4 carbon atoms, are used.
2. Process according to claim 1, characterised in that as carrier is used 1-methoxymethyl-naphthalene.
3. Process according to claim 1, characterised in that as carrier is used a mixture of 1-methoxymethyl-naphthalene and 1-acetoxymethyl-naphthalene.
4. Process according to claim 1, characterised in that as carrier is used a mixture of 1-methoxymethyl-naphtha lene and diphenyl ether.
5. Process according to claim 1, characterised in that as carrier is used a mixture of l-methoxymethyl-naphthalene, benzyl-phenyl ether and diphenyl ether.
6. An aqueous dyeing bath adapted for use in dyeing shaped articles made of aromatic polyesters or cellulose triacetate containing disperse or ingrain dyestuffs and carriers characterised in that as a carrier naphthalene derivatives of the formula R CH OR References Cited FOREIGN PATENTS 915,342 l/l963 Great Britain 8175 985,143 3/1965 Great Britain 8173 1,000,407 8/1965 Great Britain -173 GEORGE F. LESMES, Primary Examiner T. J. HERBERT, 111., Assistant Examiner US. Cl. X.R. 8-l73, 179
US689769A 1966-12-17 1967-12-12 Process for the dyeing of shaped articles made of aromatic polyesters of cellulose triacetate Expired - Lifetime US3561911A (en)

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US (1) US3561911A (en)
BE (1) BE707970A (en)
CH (2) CH487295A (en)
DE (1) DE1619497A1 (en)
FR (1) FR1562876A (en)
GB (1) GB1139108A (en)
NL (1) NL6717037A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2310444A1 (en) * 1973-01-26 1976-12-03 Ciba Geigy Ag PROCESS FOR COLORING HYDROPHOBIC SYNTHETIC FIBERS
US4310330A (en) * 1979-06-21 1982-01-12 Nippon Sheet Glass Co., Ltd. Method for the manufacture of a colored nonfogging article

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2310444A1 (en) * 1973-01-26 1976-12-03 Ciba Geigy Ag PROCESS FOR COLORING HYDROPHOBIC SYNTHETIC FIBERS
US4310330A (en) * 1979-06-21 1982-01-12 Nippon Sheet Glass Co., Ltd. Method for the manufacture of a colored nonfogging article

Also Published As

Publication number Publication date
CH1764167A4 (en) 1969-11-28
BE707970A (en) 1968-06-14
CH487295A (en) 1969-11-28
GB1139108A (en) 1969-01-08
FR1562876A (en) 1969-04-11
NL6717037A (en) 1968-06-18
DE1619497A1 (en) 1971-06-03

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