CA2000411A1 - Carriers for the dyeing of polyester materials - Google Patents
Carriers for the dyeing of polyester materialsInfo
- Publication number
- CA2000411A1 CA2000411A1 CA002000411A CA2000411A CA2000411A1 CA 2000411 A1 CA2000411 A1 CA 2000411A1 CA 002000411 A CA002000411 A CA 002000411A CA 2000411 A CA2000411 A CA 2000411A CA 2000411 A1 CA2000411 A1 CA 2000411A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- alkyl
- dyeing
- carrier
- mol
- 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.)
- Abandoned
Links
Classifications
-
- 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
- D06P1/65118—Compounds containing hydroxyl groups
-
- 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
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
- D06P1/6498—Compounds containing -CONCO-, e.g. phthalimides, hydantoine; Compounds containing RCONHSO2R (R=H or hydrocarbon)
-
- 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
- D06P1/65125—Compounds containing ester groups
-
- 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
- D06P1/65131—Compounds containing ether or acetal groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Abstract
Carriers for the dyeing of polyester materials Abstract The carrier mixture contains N-alkylphthalimides and compounds of the general formula
Description
Z00~411 The invention relate~ to carrier~, thelr prepara-tions and processes Por the dyeing of polyester materials by means of dispersed dyestuffs in the presence of these carriers.
The known carriers used in textile practice for the dyeing of polyesters include halogenobenzenes, halogenotoluenes, N-alkylphthalimide~, aromatic carboxylic esters, methylnaphthalene, diphenyl, diphenyl ethers, naphthol ethers, phenol ethers and hydroxydi-phenyls. However, these compound~ have disadvantages. All compounds, with the exception of N-alkylphthalimides, have a strong characteristic odour. Methylnaphthalene and the hydroxydiphenyls adversely affect the light fastness of the dyeing. Diphenyl ether has the disadvantage that its efficiency as a carrier strongly depend3 on the structure of the dispersed dyestuff used and therefore often nonreproducib~e dyes are obtained. N-alkylphthalimides exhibit a strong decrea~e in their efficiency as carriers at dyeing temperatures below 98~, which restricts their use in the upper regions of open dyeing machines in which this temperature is not reached.
Phthalic esters and ben~oic ester3 have only limited efficiency as carriers and limited levelling properties and therefore require the use of large amounts.
The ob~ect of the present invention is to provide highly efficient halogen-free carriers which produce a level dyeing when used in small amounts. At the same time, the dyeing produced should meet high demands in ~, -.i-Le A 26 399 - 1 -,- "", ...
.. ~......... . .~ . -:- 2000~1~
terms of fastness properties and in the dyeing of mixed fibres no ~taining of the ad~acent fibres ~hould take pl~ce.
It has now been found that this ob~ect can be achieved by means of the c~rrlers according to the invention which contain a mixture of N-alkylphthalimides (I) and compounds of the general formula R~ ~)m ~ cO0 in which R i- C1-C7-~lkyl; ph-nyl, b-nzyl or ph-nyl-thyl, wh~ch can be ub~ti~ut~d by C1-C4-~lkyl, C1-C4--lkoxy or Cl-C4-alkoxycarbonyl, R1 i~ hydrog~n, C1-C4--lkyl, C1-C3-~lkylc~rbonyloxy, hydroxyl or Cl-C4-alkoxycarbonyl, m i5 0 or 1, n i~ O or 1, m and n not being O at the ~am- tim~ Th-se mixtures of active carrier cubstances exhibit a synergis-tic increase in the effect as dyeing accelerator, com- ~ -pared with the individual components.
- The preferred weight ratio of N-alkylphthalimides (T) to the compounds (II) i~ 0.5 - 12 : 1. --Since the carrier mixtures according to the invention are water-insoluble, they are preferably added (to the dye liquors) in the form of preparations which contain emulsifiers and disper~ants and, if desired, ~--solvents. ~--`
Preference is given to carrier mixtures ... ~
Le A 26 399 - 2 - -~-;-. ~ . , , . . ~ , . ~ : :. .
-ZOOQ41~
containing 1.) 40-90, in particular 45-80, ~ by welght of ~I), 2.) 8-58, in particular 10-45, % by weight of (II), 3.) 2-30, in particular 10-20, % by weight of an emul-sifier and 4.) 0-10% by weight of a solvent.
The components 1.) - 4.) can also be used as mixtures.
N-alkylphthalimides (I) are understood to mean in particular phthalimides, or mixtures of them, sub~tituted on the nitrogen by straight-chain or branched alkyl radicals (Cl-C6), which can be prepared, for example, by reaction of phthalicanamines hydride or of phthalic esters with a means. The carriers can therefore contain phthalimides and phthalic esters as a result of their preparation.
Example~ of compounds (II) are aromatic mono-carboxylic esters (for example esters of benzoic acid, methylbenzoic acid, salicylic acid), dicarboxylic esters (for example esters of terephthalic acid or phthalic acid), carbona~es (for example diphenyl carbonate~ and ethers (for example diphenyl ether or ditolyl ether). The alcohol components of the esters can be, for example, Cl-C6-alkanols, phenols and benzyl alcohol.
Nonionic and anionic emulsifiers are preferred as emulsifiers 3.).
Examples of suitable emulsifiers are mixtures of a) ethoxylated oils, such as castor oil or soya bean oil, ethoxylated alcohol~, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers, b) alkali metal salts, alkaline earth metal salts and/or ammonium salts Le A 26 399 - 3 -: ~. ' ' " , ~' ' ~:, " '' . : ' zoao4ll of organic sulfonic acids having at least 10 csrbon atoms, such as dodecylbenzenesulfonic acid, dii~obutyl-naphthalenesulfonic acid, alpha-~ulfo fatty acid~ and N-methylricinoleotauride.
Examples of suitable solvents 4.), which may improve the viscosity of the formulation, are alkanols, glycols, ketones, N-substituted caprolactams or ether~.
Particularly preferred carriers contain 1.) 50-75~ by weight of an N-alkylphthalimide which has a straight-chain or branched alkyl radical of 3-5 C
atoms, 2.) 10-40% by weight of a C,-C,-alkyl, phenyl or benzyl ester of benzoic, methylbenzoic, terephthalic, phthalic or 6alicylic acid or diphenyl carbonate, diphenyl ether lS or ditolyl ether and 3.) 5-20~ by weight of an addition product of 15-30 mol of ethylene oxide with castor oil or soya bean oil, or 5-S0 mol of ethylene oxide and/or propylene oxide with C,6-C22-fatty alcohols, octyl- or nonylphenol or phenylethyl-phenol, alkali metal salts, alkaline earth metal salts, ammonium salts or mono-, di- or triethanolamine salts of dodecylbenzenesulfonic acid.
Since the carrier mixtures according to the invention are very compatible with other carriers, they can also be used in a mixture with other known carriers.
The dispersed dyestuffs which are used for the dyeing are the dispersed dyestuffs customarily used for the dyeing of polyesters, such as described, for example, in ~Colour Index~ Vol. 2, p. 2483-2741, 3rd Edition, j(l971). The dyeing in the presence of the carriers Le A 26 399 - 4 -20()Q4~
according to the ~nvention is carried out by the batch-wi~e processes cu~tomary for the dyeing by me~n~ of di~persed dyestuff~; the~e include the cu~tomary proce~
operating at 98C and the high-temperature proce~.
The carrier mixtures according to the invention are also suitable for the dyeing of polyester/wool and polyester/cotton mixed fabrics, because, if they are used, the staining of the wool and cotton portions by the dispersed dyestuffs is avoided.
The use of the carrier mixtures makes it po~sible to dye structures, for example threads, fibres, woven fabrics, mixed fabrics, films and sheets made of poly-esters such as glycol polyterephthalate, or polyester mixed fabric by means of dispersed dyestuffs in deep shades and highly uniformly. The dyeing can be carried out at temperatures of 90-140C, the preferred use in industry taking place at 90-105C. An additional advantage of the carrier formulations described is the very good efficiency below the boiling temperature, which is not shown by pure N-alkylphthalimide carriers, for example at 95C, which is often not exceeded under practical con-ditions in the case of open dyeing temperatures (sic).
The amount of the mixture of carriers (I) and (II) required for carrying out the dyeing can be easily determined from ca~e to case by preliminary tests. In general, amounts of 1 to 7 g per litre of dye liquor at conventional liguor ratios of 5 : 1 to 40 : 1 has proven to be suitable.
The use of components (I) and (II) as carriers in the dyeing of polyesters is known.
Le A 26 399 - 5 -.. . .
~ i .
.
~ .
` Z00(~4~1 Thus, for example, the use of N-alkylphthalimide~
is descrlbed in German Patent Specification 1,769,210, the use of phthalic esters in US Patent Speclfication 4,032,291 and the use of benzoic esters in German Auslegeschrift 2,348,363. German Patent Specification 1,769,210 also discloses the use of mixtures of N-alkyl-phthalimide~ with disubstituted benzoic esters.
Surprisingly, it has now been found that the mixtures according to the invention have a higher ef-ficiency as dyeing accelerator~ than corre~ponds to the sum of the individual efficiencies. This synergistic increase in the efficiencies is not exhibited by the previou~ly known mixtures (for example the mixtures of N-alkylphthalimide~ with alkyl-containing salicylic acid compounds ~escribed in German Patent Specification 1,769,210). The mixing ratio at which the synergistic effect is at an optimum is dependent on the components of ~: ~
the carrier mixtures and can be easily determined in the ~- -individual case by preliminary tests.
Example 1 - -Yarns made of polyester fibres are introduced at a liguor ratio of 40 : 1 in to a bath heated to 60C which co~ains per litre 0.25 g of a dye of the formula ~Br J;
2 g of a condensation product of naphthalenesulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3 g -. -.:- - -Le A 26 39~ - 6 - ~
~i.~, .. .. ... ... . . . .
.
~, . . . , .; .. , . - -20()Q41~
of a carrier formulation of the followlng compo~itlon~
1.80 g of N-alkylphthalimlde~ (alkyl - 50% of n-butyl, 50% of n-propyl) 0.75 g of methyl 4-methylbenzoate S 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid The pH of the bath i8 ad~usted to 4.5 - 5 with acetic acid. The bath is then heated to 98C and main-tained at this temperature for 60 minutes. This give~ a uniform blue dyeing.
Examples 2-12 The dyeing is carried out as described in Example 15 1, using carrier formulations of the following composi-tions:
Example 2: 1.65 g of N-butylphthalimide 0.90 g of ethyl 4-methylbenzoate 0.20 g of calcium dodecylbenzenesulfonate (70% in butanol) 0.20 g of castor oil with about 30 mol of EO
0.05 g of ~tearyl hexaethylene glycol ether Example 3: 2.25 g of N-butylphthalimide 0.30 g of dimethyl terephthalate ester 0.25 g of tri(methylphen~lethyl)phenol with about 15 mol of EO
Le A 26 399 - 7 -:
.. . . .
:. . ~- .
20~ t~411 O.20 g of the monoethanolamine salt of dodecylbenzene~ulfonic ~cid Example 4: 1.50 g of N-butylphthalimide 1.05 g of methyl salicylate ester 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the monoethanolamine salt of do-decylbenzenesulfonic acid Example 5: 1.50 g of N-alkylphthalimides (alkyl = 50%
of n-butyl, 30% of propyl, 20% of ethyl) 1.05 g of benzyl benzoate ester 0.25 g of di(phenylethyl)phenol with about lO mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid Example 6: 1.80 g of N-alkylphthalimides (alkyl = 70-% of butyl, 30% of propyl) 0.75 g of n-butyl benzoate 0.30 g of castor oil with about 30 mol of EO
0.15 g of calcium ~odecylbenzenesulfonate (70~ in butanol) Example 7s 2.10 g of N-butylph~halLmide ~ ~.
2S 0.45 g of phenyl benzoate 0.30 g of di(methylphenylethyl)phenol with Le A 26 399 - 8 -- ~ - ~ ; .: . ,~ , : - : : -2~ 411 about 12 mol of EO
0.15 g of calcium dodecylbenzene sulfonate (70% in butanol) Example 8: 1.50 g of N-butylphthalimide 1.05 g of diphenyl ether 0.30 g of di(phenylethyl)phenol with about 10 mol of EO
0.15 g of the monoethanolamine salt of dodecylbenzenesulfonic acid Example 9: 1.90 g of N-alkylphthalimide (alkyl = 50% ~.
of butyl, 30% of propyl, 20% of ethyl) 0.65 g of diphenyl carbonate 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
O.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid Example 10: 2.10 g of N-butylphthalimide 0.45 g of butyl 2-methylbenzoate 0.25 ~ of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the monoethanolamine ~alt of dodecylbenzenesulfonic acid Example 11: 1.50 g of N-alkylphthalimid (alkyl = 60%
of n-butyl, 40% of n-propyl) -1.05 g of ethyl 3-methylbenzoate Le A 26 399 - 9 -: .
;: ,.:, , .. ~.. . ~ ~ : . .
200(~41i 0.25 g of tri(methylphenylethyl)phenol with about lS mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid Example 12: 1.50 g of N-butylphthalimide l.OS g of ditolyl ether 0.25 g of tri(methylphenylethyl~phenol with about 15 mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid In each case, a uniform blue dyeing is obtained.
The efficiency as carrier of the carrier mixture~ of Examples 1 - 12 is determined by comparison with the colour depth obtained. The table below lists the amount of carrier mixture and that of e~ter/ether (II) required for obtaining the same colour depth. The amount listed i6 based on the amount of N-alkylphthalimide (I) = 100. The small amount of the mixtures show that they have a more advantageous efficiency as carriers, compared with the individual components.
Le A 26 399 - 10 -.. ;, .: ~- . : -.; ~, ~, . .- . -- ZOO(~
Example % by weight of the Necessary amount of compounds in the mixture Mixture Components II
_ Le A 26 399 .,.- . ' . .' ' ' : ' .~ . . :
- 2()(J(~4~1 Example 13 (comDarative exam~le with respect to ~eEman Pa~ent~ co~ L~r~e~h9 Exam~le 1 Yarns made of polyester fibres are introduced at a liquor ratio of 40 s 1 into a bath heated to 60C which contain-R per litre 0.25 g of a dye of the formula OzN~N N~N,CH2-CH2 CN
2 g of a condensation product of naphthalenesulfonate and formaldehyde, 2 ~ of æodium dihydrogen phosphate and 3 g of a carrier formulation of the following composition:
1.80 g of N~alkylphthalimides (alkyl = 60% of butyl, 40%
of propyl) 0.75 g of ethyl o-cresotinate 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid The pH of the bath is ad~usted to 4.5 - 5 with acetic acid. The bath is ~hen heated to 98C and main-tained at this temperature for 60 minutes. This gives a uniform blue dyeing. The efficiency as carrier is deter-mined as described above ((I) = 100).
Le A 26 399 - 12 -. ~ , ~ ' !
"~ .' ' :
7, "~ ` ' ~, ' ' . ' ~ by weight of the Neces~ary ~mount of component in the mixture mlxture / e~ter -60 of I 100 100 25 of the ester according to German Patent Specification 1,769 210 In contrast to the carrier mixtures claimed, this mixture shows no synergistic increase of the efficiency as carrier, compared to the individual component~.
Example 14 Pieced goods consisting in weft and warp of polyester spin fi.bres are introduced at a liquor ratio of 40 : 1 into a bath heated to 50C which contains per litre 0.25 g of a ~ye of the formula ,CH2-CH2-CN
0 ~ N= ~
2 ~ \,cc~ `cH2-cH2-cooc2H5 2 g of a condensation product of naphthalenesulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 2.5 g of a carrier formulation of the following composition:
1.80 g of N-alkylphthalimides (alkyl = 60% of butyl, 40 of propyl) 0.75 g of methyl 4-methylbenzoate 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the jmonoethanolamine salt of ~' Le A 26 399 - 13 -.,, ~ ~ ~ ,..
~ -::; , . . . .
20n~4ll dodecylbenzenesulfonic acid The pH of the bath i8 ad~usted to 4.5 - 5 with acetic acid. The dye liquor i~ then brought to boiling temperature and maintained at this temperature for 1 hour. A full uniform red dyeing is obtained.
Example 15 Polyester spin fibres are introduced at a liquor ratio of 15 s 1 into a dye liquor containing per litre 1 g of a disperse dyestuff according to Example 14, 0.03 g of a dye according to Colour Index, 2nd Edition (1956) Volume 3, No. 12790, 2 g of a condensation product of naphthalenesulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3.5 g of a carrier formulation from Example 14. The pH of the bath is ad~usted to 4.5 -5 with acetic acid. The liquor i8 BlOWly heated to 98C
and the material is treated at this temperature for 1 hour. A dark red-brown dyeing ls obtained.
Le A 26 399 - 14 -
The known carriers used in textile practice for the dyeing of polyesters include halogenobenzenes, halogenotoluenes, N-alkylphthalimide~, aromatic carboxylic esters, methylnaphthalene, diphenyl, diphenyl ethers, naphthol ethers, phenol ethers and hydroxydi-phenyls. However, these compound~ have disadvantages. All compounds, with the exception of N-alkylphthalimides, have a strong characteristic odour. Methylnaphthalene and the hydroxydiphenyls adversely affect the light fastness of the dyeing. Diphenyl ether has the disadvantage that its efficiency as a carrier strongly depend3 on the structure of the dispersed dyestuff used and therefore often nonreproducib~e dyes are obtained. N-alkylphthalimides exhibit a strong decrea~e in their efficiency as carriers at dyeing temperatures below 98~, which restricts their use in the upper regions of open dyeing machines in which this temperature is not reached.
Phthalic esters and ben~oic ester3 have only limited efficiency as carriers and limited levelling properties and therefore require the use of large amounts.
The ob~ect of the present invention is to provide highly efficient halogen-free carriers which produce a level dyeing when used in small amounts. At the same time, the dyeing produced should meet high demands in ~, -.i-Le A 26 399 - 1 -,- "", ...
.. ~......... . .~ . -:- 2000~1~
terms of fastness properties and in the dyeing of mixed fibres no ~taining of the ad~acent fibres ~hould take pl~ce.
It has now been found that this ob~ect can be achieved by means of the c~rrlers according to the invention which contain a mixture of N-alkylphthalimides (I) and compounds of the general formula R~ ~)m ~ cO0 in which R i- C1-C7-~lkyl; ph-nyl, b-nzyl or ph-nyl-thyl, wh~ch can be ub~ti~ut~d by C1-C4-~lkyl, C1-C4--lkoxy or Cl-C4-alkoxycarbonyl, R1 i~ hydrog~n, C1-C4--lkyl, C1-C3-~lkylc~rbonyloxy, hydroxyl or Cl-C4-alkoxycarbonyl, m i5 0 or 1, n i~ O or 1, m and n not being O at the ~am- tim~ Th-se mixtures of active carrier cubstances exhibit a synergis-tic increase in the effect as dyeing accelerator, com- ~ -pared with the individual components.
- The preferred weight ratio of N-alkylphthalimides (T) to the compounds (II) i~ 0.5 - 12 : 1. --Since the carrier mixtures according to the invention are water-insoluble, they are preferably added (to the dye liquors) in the form of preparations which contain emulsifiers and disper~ants and, if desired, ~--solvents. ~--`
Preference is given to carrier mixtures ... ~
Le A 26 399 - 2 - -~-;-. ~ . , , . . ~ , . ~ : :. .
-ZOOQ41~
containing 1.) 40-90, in particular 45-80, ~ by welght of ~I), 2.) 8-58, in particular 10-45, % by weight of (II), 3.) 2-30, in particular 10-20, % by weight of an emul-sifier and 4.) 0-10% by weight of a solvent.
The components 1.) - 4.) can also be used as mixtures.
N-alkylphthalimides (I) are understood to mean in particular phthalimides, or mixtures of them, sub~tituted on the nitrogen by straight-chain or branched alkyl radicals (Cl-C6), which can be prepared, for example, by reaction of phthalicanamines hydride or of phthalic esters with a means. The carriers can therefore contain phthalimides and phthalic esters as a result of their preparation.
Example~ of compounds (II) are aromatic mono-carboxylic esters (for example esters of benzoic acid, methylbenzoic acid, salicylic acid), dicarboxylic esters (for example esters of terephthalic acid or phthalic acid), carbona~es (for example diphenyl carbonate~ and ethers (for example diphenyl ether or ditolyl ether). The alcohol components of the esters can be, for example, Cl-C6-alkanols, phenols and benzyl alcohol.
Nonionic and anionic emulsifiers are preferred as emulsifiers 3.).
Examples of suitable emulsifiers are mixtures of a) ethoxylated oils, such as castor oil or soya bean oil, ethoxylated alcohol~, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers, b) alkali metal salts, alkaline earth metal salts and/or ammonium salts Le A 26 399 - 3 -: ~. ' ' " , ~' ' ~:, " '' . : ' zoao4ll of organic sulfonic acids having at least 10 csrbon atoms, such as dodecylbenzenesulfonic acid, dii~obutyl-naphthalenesulfonic acid, alpha-~ulfo fatty acid~ and N-methylricinoleotauride.
Examples of suitable solvents 4.), which may improve the viscosity of the formulation, are alkanols, glycols, ketones, N-substituted caprolactams or ether~.
Particularly preferred carriers contain 1.) 50-75~ by weight of an N-alkylphthalimide which has a straight-chain or branched alkyl radical of 3-5 C
atoms, 2.) 10-40% by weight of a C,-C,-alkyl, phenyl or benzyl ester of benzoic, methylbenzoic, terephthalic, phthalic or 6alicylic acid or diphenyl carbonate, diphenyl ether lS or ditolyl ether and 3.) 5-20~ by weight of an addition product of 15-30 mol of ethylene oxide with castor oil or soya bean oil, or 5-S0 mol of ethylene oxide and/or propylene oxide with C,6-C22-fatty alcohols, octyl- or nonylphenol or phenylethyl-phenol, alkali metal salts, alkaline earth metal salts, ammonium salts or mono-, di- or triethanolamine salts of dodecylbenzenesulfonic acid.
Since the carrier mixtures according to the invention are very compatible with other carriers, they can also be used in a mixture with other known carriers.
The dispersed dyestuffs which are used for the dyeing are the dispersed dyestuffs customarily used for the dyeing of polyesters, such as described, for example, in ~Colour Index~ Vol. 2, p. 2483-2741, 3rd Edition, j(l971). The dyeing in the presence of the carriers Le A 26 399 - 4 -20()Q4~
according to the ~nvention is carried out by the batch-wi~e processes cu~tomary for the dyeing by me~n~ of di~persed dyestuff~; the~e include the cu~tomary proce~
operating at 98C and the high-temperature proce~.
The carrier mixtures according to the invention are also suitable for the dyeing of polyester/wool and polyester/cotton mixed fabrics, because, if they are used, the staining of the wool and cotton portions by the dispersed dyestuffs is avoided.
The use of the carrier mixtures makes it po~sible to dye structures, for example threads, fibres, woven fabrics, mixed fabrics, films and sheets made of poly-esters such as glycol polyterephthalate, or polyester mixed fabric by means of dispersed dyestuffs in deep shades and highly uniformly. The dyeing can be carried out at temperatures of 90-140C, the preferred use in industry taking place at 90-105C. An additional advantage of the carrier formulations described is the very good efficiency below the boiling temperature, which is not shown by pure N-alkylphthalimide carriers, for example at 95C, which is often not exceeded under practical con-ditions in the case of open dyeing temperatures (sic).
The amount of the mixture of carriers (I) and (II) required for carrying out the dyeing can be easily determined from ca~e to case by preliminary tests. In general, amounts of 1 to 7 g per litre of dye liquor at conventional liguor ratios of 5 : 1 to 40 : 1 has proven to be suitable.
The use of components (I) and (II) as carriers in the dyeing of polyesters is known.
Le A 26 399 - 5 -.. . .
~ i .
.
~ .
` Z00(~4~1 Thus, for example, the use of N-alkylphthalimide~
is descrlbed in German Patent Specification 1,769,210, the use of phthalic esters in US Patent Speclfication 4,032,291 and the use of benzoic esters in German Auslegeschrift 2,348,363. German Patent Specification 1,769,210 also discloses the use of mixtures of N-alkyl-phthalimide~ with disubstituted benzoic esters.
Surprisingly, it has now been found that the mixtures according to the invention have a higher ef-ficiency as dyeing accelerator~ than corre~ponds to the sum of the individual efficiencies. This synergistic increase in the efficiencies is not exhibited by the previou~ly known mixtures (for example the mixtures of N-alkylphthalimide~ with alkyl-containing salicylic acid compounds ~escribed in German Patent Specification 1,769,210). The mixing ratio at which the synergistic effect is at an optimum is dependent on the components of ~: ~
the carrier mixtures and can be easily determined in the ~- -individual case by preliminary tests.
Example 1 - -Yarns made of polyester fibres are introduced at a liguor ratio of 40 : 1 in to a bath heated to 60C which co~ains per litre 0.25 g of a dye of the formula ~Br J;
2 g of a condensation product of naphthalenesulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3 g -. -.:- - -Le A 26 39~ - 6 - ~
~i.~, .. .. ... ... . . . .
.
~, . . . , .; .. , . - -20()Q41~
of a carrier formulation of the followlng compo~itlon~
1.80 g of N-alkylphthalimlde~ (alkyl - 50% of n-butyl, 50% of n-propyl) 0.75 g of methyl 4-methylbenzoate S 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid The pH of the bath i8 ad~usted to 4.5 - 5 with acetic acid. The bath is then heated to 98C and main-tained at this temperature for 60 minutes. This give~ a uniform blue dyeing.
Examples 2-12 The dyeing is carried out as described in Example 15 1, using carrier formulations of the following composi-tions:
Example 2: 1.65 g of N-butylphthalimide 0.90 g of ethyl 4-methylbenzoate 0.20 g of calcium dodecylbenzenesulfonate (70% in butanol) 0.20 g of castor oil with about 30 mol of EO
0.05 g of ~tearyl hexaethylene glycol ether Example 3: 2.25 g of N-butylphthalimide 0.30 g of dimethyl terephthalate ester 0.25 g of tri(methylphen~lethyl)phenol with about 15 mol of EO
Le A 26 399 - 7 -:
.. . . .
:. . ~- .
20~ t~411 O.20 g of the monoethanolamine salt of dodecylbenzene~ulfonic ~cid Example 4: 1.50 g of N-butylphthalimide 1.05 g of methyl salicylate ester 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the monoethanolamine salt of do-decylbenzenesulfonic acid Example 5: 1.50 g of N-alkylphthalimides (alkyl = 50%
of n-butyl, 30% of propyl, 20% of ethyl) 1.05 g of benzyl benzoate ester 0.25 g of di(phenylethyl)phenol with about lO mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid Example 6: 1.80 g of N-alkylphthalimides (alkyl = 70-% of butyl, 30% of propyl) 0.75 g of n-butyl benzoate 0.30 g of castor oil with about 30 mol of EO
0.15 g of calcium ~odecylbenzenesulfonate (70~ in butanol) Example 7s 2.10 g of N-butylph~halLmide ~ ~.
2S 0.45 g of phenyl benzoate 0.30 g of di(methylphenylethyl)phenol with Le A 26 399 - 8 -- ~ - ~ ; .: . ,~ , : - : : -2~ 411 about 12 mol of EO
0.15 g of calcium dodecylbenzene sulfonate (70% in butanol) Example 8: 1.50 g of N-butylphthalimide 1.05 g of diphenyl ether 0.30 g of di(phenylethyl)phenol with about 10 mol of EO
0.15 g of the monoethanolamine salt of dodecylbenzenesulfonic acid Example 9: 1.90 g of N-alkylphthalimide (alkyl = 50% ~.
of butyl, 30% of propyl, 20% of ethyl) 0.65 g of diphenyl carbonate 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
O.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid Example 10: 2.10 g of N-butylphthalimide 0.45 g of butyl 2-methylbenzoate 0.25 ~ of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the monoethanolamine ~alt of dodecylbenzenesulfonic acid Example 11: 1.50 g of N-alkylphthalimid (alkyl = 60%
of n-butyl, 40% of n-propyl) -1.05 g of ethyl 3-methylbenzoate Le A 26 399 - 9 -: .
;: ,.:, , .. ~.. . ~ ~ : . .
200(~41i 0.25 g of tri(methylphenylethyl)phenol with about lS mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid Example 12: 1.50 g of N-butylphthalimide l.OS g of ditolyl ether 0.25 g of tri(methylphenylethyl~phenol with about 15 mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid In each case, a uniform blue dyeing is obtained.
The efficiency as carrier of the carrier mixture~ of Examples 1 - 12 is determined by comparison with the colour depth obtained. The table below lists the amount of carrier mixture and that of e~ter/ether (II) required for obtaining the same colour depth. The amount listed i6 based on the amount of N-alkylphthalimide (I) = 100. The small amount of the mixtures show that they have a more advantageous efficiency as carriers, compared with the individual components.
Le A 26 399 - 10 -.. ;, .: ~- . : -.; ~, ~, . .- . -- ZOO(~
Example % by weight of the Necessary amount of compounds in the mixture Mixture Components II
_ Le A 26 399 .,.- . ' . .' ' ' : ' .~ . . :
- 2()(J(~4~1 Example 13 (comDarative exam~le with respect to ~eEman Pa~ent~ co~ L~r~e~h9 Exam~le 1 Yarns made of polyester fibres are introduced at a liquor ratio of 40 s 1 into a bath heated to 60C which contain-R per litre 0.25 g of a dye of the formula OzN~N N~N,CH2-CH2 CN
2 g of a condensation product of naphthalenesulfonate and formaldehyde, 2 ~ of æodium dihydrogen phosphate and 3 g of a carrier formulation of the following composition:
1.80 g of N~alkylphthalimides (alkyl = 60% of butyl, 40%
of propyl) 0.75 g of ethyl o-cresotinate 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the monoethanolamine salt of dodecylbenzenesulfonic acid The pH of the bath is ad~usted to 4.5 - 5 with acetic acid. The bath is ~hen heated to 98C and main-tained at this temperature for 60 minutes. This gives a uniform blue dyeing. The efficiency as carrier is deter-mined as described above ((I) = 100).
Le A 26 399 - 12 -. ~ , ~ ' !
"~ .' ' :
7, "~ ` ' ~, ' ' . ' ~ by weight of the Neces~ary ~mount of component in the mixture mlxture / e~ter -60 of I 100 100 25 of the ester according to German Patent Specification 1,769 210 In contrast to the carrier mixtures claimed, this mixture shows no synergistic increase of the efficiency as carrier, compared to the individual component~.
Example 14 Pieced goods consisting in weft and warp of polyester spin fi.bres are introduced at a liquor ratio of 40 : 1 into a bath heated to 50C which contains per litre 0.25 g of a ~ye of the formula ,CH2-CH2-CN
0 ~ N= ~
2 ~ \,cc~ `cH2-cH2-cooc2H5 2 g of a condensation product of naphthalenesulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 2.5 g of a carrier formulation of the following composition:
1.80 g of N-alkylphthalimides (alkyl = 60% of butyl, 40 of propyl) 0.75 g of methyl 4-methylbenzoate 0.25 g of tri(methylphenylethyl)phenol with about 15 mol of EO
0.20 g of the jmonoethanolamine salt of ~' Le A 26 399 - 13 -.,, ~ ~ ~ ,..
~ -::; , . . . .
20n~4ll dodecylbenzenesulfonic acid The pH of the bath i8 ad~usted to 4.5 - 5 with acetic acid. The dye liquor i~ then brought to boiling temperature and maintained at this temperature for 1 hour. A full uniform red dyeing is obtained.
Example 15 Polyester spin fibres are introduced at a liquor ratio of 15 s 1 into a dye liquor containing per litre 1 g of a disperse dyestuff according to Example 14, 0.03 g of a dye according to Colour Index, 2nd Edition (1956) Volume 3, No. 12790, 2 g of a condensation product of naphthalenesulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3.5 g of a carrier formulation from Example 14. The pH of the bath is ad~usted to 4.5 -5 with acetic acid. The liquor i8 BlOWly heated to 98C
and the material is treated at this temperature for 1 hour. A dark red-brown dyeing ls obtained.
Le A 26 399 - 14 -
Claims (5)
1. Carrier mixture containing N-alkylphthalimides (1) and compounds of the general formula II
in which R is C1-C7-alkyl; phenyl, benzyl or phenylethyl, which can be substituted by C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl, R1 is hydrogen, C1-C4-alkyl, Cl-C4-alkylcarbonyloxy, hydroxyl or C1-C4-alkoxycarbonyl, m is 0 or 1, n is 0 or 1, m and n not being 0 at the same time.
in which R is C1-C7-alkyl; phenyl, benzyl or phenylethyl, which can be substituted by C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl, R1 is hydrogen, C1-C4-alkyl, Cl-C4-alkylcarbonyloxy, hydroxyl or C1-C4-alkoxycarbonyl, m is 0 or 1, n is 0 or 1, m and n not being 0 at the same time.
2. Carrier mixture according to Claim 1, containing components (I) and (II) in a weight ratio of 0.5 - 12 :
1.
1.
3. Carrier mixture according to Claim 1, containing 1.) 40-90% by weight of (I), 2.) 8-58% by weight of (II), 3.) 2-30% by weight of emulsifier and
4.) 0-10% by weight of a solvent.
4. Carrier mixture according to Claim 1, containing 1.) 50-75% by weight of an N-alkylphthalimide which has a straight-chain or branched alkyl radical of 3-5 C atoms, 2.) 10-40% by weight of a C1-C4-alkyl, phenyl or benzyl ester of benzoic, methylbenzoic, tereph-thalic, phthalic or salicylic acid or diphenyl carbonate, diphenyl ether or ditolyl ether and 3.) 5-20% by weight of an addition product of 15-30 mol of ethylene oxide with castor oil or soya bean oil, of 5-50 mol of ethylene oxide and/or propylene oxide with C16-C22-fatty alcohols, octylphenol or nonylphenol or phenylethylphenol, alkali metal salts, alkaline earth metal salts, ammonium salts or (di)ethanolamine salts of dodecylbenzenesulfonic acid.
4. Carrier mixture according to Claim 1, containing 1.) 50-75% by weight of an N-alkylphthalimide which has a straight-chain or branched alkyl radical of 3-5 C atoms, 2.) 10-40% by weight of a C1-C4-alkyl, phenyl or benzyl ester of benzoic, methylbenzoic, tereph-thalic, phthalic or salicylic acid or diphenyl carbonate, diphenyl ether or ditolyl ether and 3.) 5-20% by weight of an addition product of 15-30 mol of ethylene oxide with castor oil or soya bean oil, of 5-50 mol of ethylene oxide and/or propylene oxide with C16-C22-fatty alcohols, octylphenol or nonylphenol or phenylethylphenol, alkali metal salts, alkaline earth metal salts, ammonium salts or (di)ethanolamine salts of dodecylbenzenesulfonic acid.
5. Process for the dyeing of polyester materials with dispersed dyestuffs in the presence of carrier mixtures of Claim 1.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3834737A DE3834737A1 (en) | 1988-10-12 | 1988-10-12 | CARRIER FOR DYING POLYESTER MATERIALS |
DEP3834737.7 | 1988-10-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2000411A1 true CA2000411A1 (en) | 1990-04-12 |
Family
ID=6364951
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002000411A Abandoned CA2000411A1 (en) | 1988-10-12 | 1989-10-10 | Carriers for the dyeing of polyester materials |
Country Status (7)
Country | Link |
---|---|
US (1) | US4994089A (en) |
EP (1) | EP0364792B1 (en) |
JP (1) | JPH02169778A (en) |
AU (1) | AU615581B2 (en) |
CA (1) | CA2000411A1 (en) |
DE (2) | DE3834737A1 (en) |
PT (1) | PT91875B (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2037597B1 (en) * | 1990-08-27 | 1994-03-16 | Sandoz Ag | IMPROVEMENTS IN OR RELATED TO ORGANIC COMPOUNDS. |
WO1998038275A1 (en) * | 1997-02-28 | 1998-09-03 | Sybron Chemicals Inc. | Clay-containing textile material treating composition and method |
US5972049A (en) * | 1998-01-28 | 1999-10-26 | Sybron Chemicals Inc. | Clay-containing dispersing composition for carriers used in the disperse dyeing of hydrophobic textiles |
JP4721532B2 (en) * | 2001-02-21 | 2011-07-13 | 東レ株式会社 | Colored polyphenylene sulfide fiber and method for producing the same |
US6652602B2 (en) * | 2001-12-21 | 2003-11-25 | N.V. Bekaert S.A. | Color dyeing system for plastic films |
ATE270724T1 (en) * | 2002-03-19 | 2004-07-15 | Boehme Chem Fab Kg | USE OF ALKYL BENZOATES AS EVENING AGENT FOR DYEING POLYESTER FIBER MATERIALS |
DE50301260D1 (en) * | 2003-02-28 | 2006-02-09 | Boehme Chem Fab Kg | leveling agents |
US7035439B2 (en) * | 2003-07-30 | 2006-04-25 | Xerox Corporation | System and method for measuring and quantizing document quality |
JP4810224B2 (en) * | 2005-12-28 | 2011-11-09 | 共栄社化学株式会社 | Textile product cleaner |
US10202712B2 (en) | 2009-07-31 | 2019-02-12 | Basf Se | Producing spinnable and dyeable polyester fibers |
JP5629104B2 (en) * | 2010-03-24 | 2014-11-19 | 株式会社クラレ | Method for dyeing polyetherimide fiber and dyed product thereof |
US20130263384A1 (en) * | 2010-12-16 | 2013-10-10 | Masaru Harada | Processing agent for polyester fiber structure and production method for polyester fiber structure using same |
CN107541968B (en) * | 2016-06-29 | 2020-04-24 | 苏州联胜化学有限公司 | Polyester dyeing carrier and preparation method thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2881045A (en) * | 1954-06-17 | 1959-04-07 | American Cyanamid Co | Method of dyeing synthetic fibrous materials |
FR1140000A (en) * | 1955-01-05 | 1957-07-09 | Hoechst Ag | Process for dyeing articles made of polyester fibers with a high degree of polymerization |
DE1769210A1 (en) * | 1968-04-20 | 1970-12-17 | Bayer Ag | Printing and coloring processes |
US4032291A (en) * | 1976-01-12 | 1977-06-28 | Ciba-Geigy Corporation | Phenyl phthalate carriers in dyeing and printing synthetic fibers |
EP0033715A1 (en) * | 1980-01-31 | 1981-08-12 | Ciba-Geigy Ag | Auxiliary and its use in the dyeing or optical brightening of polyester fibre materials |
-
1988
- 1988-10-12 DE DE3834737A patent/DE3834737A1/en not_active Withdrawn
-
1989
- 1989-09-28 US US07/414,051 patent/US4994089A/en not_active Expired - Lifetime
- 1989-09-29 EP EP89118113A patent/EP0364792B1/en not_active Expired - Lifetime
- 1989-09-29 DE DE8989118113T patent/DE58903445D1/en not_active Expired - Fee Related
- 1989-10-02 PT PT91875A patent/PT91875B/en not_active IP Right Cessation
- 1989-10-10 CA CA002000411A patent/CA2000411A1/en not_active Abandoned
- 1989-10-11 AU AU42889/89A patent/AU615581B2/en not_active Ceased
- 1989-10-12 JP JP1264106A patent/JPH02169778A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
JPH02169778A (en) | 1990-06-29 |
DE58903445D1 (en) | 1993-03-18 |
EP0364792A3 (en) | 1991-08-14 |
AU615581B2 (en) | 1991-10-03 |
US4994089A (en) | 1991-02-19 |
PT91875A (en) | 1990-04-30 |
AU4288989A (en) | 1990-04-26 |
EP0364792B1 (en) | 1993-02-03 |
PT91875B (en) | 1995-07-06 |
EP0364792A2 (en) | 1990-04-25 |
DE3834737A1 (en) | 1990-04-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2000411A1 (en) | Carriers for the dyeing of polyester materials | |
US4229172A (en) | Disperse dyeing of polyester with benzalketo derivatives as carriers: benzalacetone, methyl cinnamate etc. | |
GB2191217A (en) | Waterless dip dye composition | |
US4311480A (en) | Dyeing composition | |
JPH07111031B2 (en) | Auxiliary mixture and its use in dyeing synthetic fiber materials | |
US4943299A (en) | Levelling agents for disperse dyeing of polyester: ethoxylate or propoxylate of substituted phenol, emulsifier and carrier | |
US4168142A (en) | Halogen-containing esters as pH regulators in textile finishing processes | |
US3236583A (en) | Polyester dyeing with a dye solution containing polyalkylene oxide ether of phenols and a fatty acid ester of polyalkylene oxides | |
JP2612945B2 (en) | Carrier for dyeing hydrophobic fiber materials | |
EP1469121B1 (en) | Levelling agent | |
US3765831A (en) | Treatment of polypeptide fibres | |
US4013405A (en) | Aqueous printing pastes for producing transfer printing papers by rotary screen printing | |
US20070204410A1 (en) | Method For Optical Brightening Of Synthetic Fibres Or Of Synthetic Fibres Mixed With Natural Fibres | |
US3830627A (en) | Dye bath with block copolymeric propylene and ethylene oxides as foam suppressants | |
US4516979A (en) | Polybenzoates as disperse dyeing assistants | |
EP0064030B1 (en) | Dyeing auxiliary mixture and its use in dyeing synthetic fibrous materials | |
US3897207A (en) | Carrier composition and process for dyeing and printing | |
EP0064029B1 (en) | Auxiliary mixture and its use as crease-proof agent for the dyeing or optical bleaching of textile materials containing polyester fibres | |
JP3224245B2 (en) | Dyeing aid for polyester fiber | |
DE3247400C2 (en) | ||
US4277247A (en) | Process for dyeing pre-cleaned cellulose fiber material | |
CA1051614A (en) | Process for dyeing materials which contain synthetic fibres | |
DE3246383C2 (en) | ||
US3561911A (en) | Process for the dyeing of shaped articles made of aromatic polyesters of cellulose triacetate | |
EP1347091B1 (en) | Dyeing assistant |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |