CA2214918A1 - Use of aryloxypolyglycol ethers as levelling and dispersing agents - Google Patents
Use of aryloxypolyglycol ethers as levelling and dispersing agents Download PDFInfo
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- CA2214918A1 CA2214918A1 CA002214918A CA2214918A CA2214918A1 CA 2214918 A1 CA2214918 A1 CA 2214918A1 CA 002214918 A CA002214918 A CA 002214918A CA 2214918 A CA2214918 A CA 2214918A CA 2214918 A1 CA2214918 A1 CA 2214918A1
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- aryloxypolyglycol
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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
- 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
- D06P1/667—Organo-phosphorus compounds
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
-
- 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
- D06P1/60—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 polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
- D06P1/6135—Addition products of hydroxyl groups-containing compounds with oxiranes from aromatic alcohols or from phenols, naphthols
-
- 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
- D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/621—Compounds without nitrogen
- D06P1/622—Sulfonic acids or their salts
- D06P1/623—Aliphatic, aralophatic or cycloaliphatic
-
- 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
Abstract
Use of aryloxypolyglycol ethers as leveling and dispersing agents Compounds of the formula (see fig. I) in which R is hydrogen or a group of the formulae (see fig. II) where sulfonic acid esters are used only in the pH range from 7.1 to 12, and the other symbols have the meaning given in the description, are employed asleveling and dispersing agents in dyebaths and padding baths and in disperse dyestuffs.
Description
CLARIANT GMBH HOE 96/F 251 Dr. OT/we Description 5 Use of aryloxypolyglycol ethers as leveling and dispersing agents It is known to use ligninsulfonates for formulation of disperse dyestuffs. However, these ligninsulfonates are not effective with all disperse dyestuffs, since these differ 10 considerably in their chemical structure and in their properties such as particle size, particle size distribution, hydrophilicity and - although relatively low- solubility in water. Another disadvantage of ligninsulfonates is that they stain polyester fibers severely during the dyeing process. This manifests itself in a particularly troublesome manner in the case of pale hues or brilliant color shades. Furthermore, 15 these ligninsulfonates have the properties of reducing sensitive azo dyestuffs during the dyeing operation, to an increased extent in an alkaline dyebath; i.e. greatly reduced color yields are obtained when dyeing in such cases.
Dyeing in an alkaline bath at pH 7.1 to pH 12, preferably at pH 8.5 to 10, however, 20 is advantageous because oligomers from the polyester fiber are not deposited or are deposited hardly at all on the fiber surface in the form of crystals. This is a great advantage during further processing of polyester fibers, because a hot alkaline treatment to remove the oligomers, which is carried out with sodium hydroxide solution and sodium dithionite at 80 to 100~~, can be omitted. The oligomers are-25 still not removed completely enough by this treatment, and in addition an undesirable shift in the hue of the dyeing can take place.
Furthermore, during dyeing in an alkaline pH range at temperatures of 90 to 140~C, commercially available leveling and dispersing agents are often split by hydrolysis 30 and therefore become ineffective. It has been found, surprisingly, that the auxiliaries described below are effective as leveling and dispersing agents in an alkaline dyebath, and that dyeings are obtained without differences in respect of color strength and without color shade differences in combination dyeings, regardless of whether the dyeings are on sheet-like structures, yarns, threads or non-spun - CA 022l49l8 l997-09-09 material.
The invention relates to the use of aryloxypolyglycol ethers of the formula (R )3 R4 ~ o- (CH - CH2 - ~) x~ R
10 in which R is hydrogen or a group of the formulae o o ~
P--R . --P--OM, --p OM or ~ OM
R 2 1 2 OM o where sulfonic acid esters are used only in the pH range from 7.1 to 12, the R1 independently of one another are hydrogen, C1-C24-alkyl, C5-C15-cycloalkyl~ C6-C24-aryl, C7-C24-alkaryl or (CH2)zaryl, the R2 independently of one another are -OH, -O-C1-C24-alkyl, -O-C5-C,5-cycloalkyl, -O-C6-C18-aryl or a group of the formula (R1)3 R4 ~ O - (CH - CH2-O)X-M is an alkali metal ion, alkaline earth metal ion or ammonium ion of the formula N(R3)4, the R3 independently of one another are hydrogen, C1-C4-alkyl, C5-C15-cycloalkyl, C6-C18-aryl or a group of the formula -(CH2)zOH, R4 is hydrogen or methyl, x is a number from 1 to 100 and z is a number from 1 to 10, as leveling and dispersing agents.
The radicals R1, R2 and R3 are optionally substituted. Suitable substituents arehalogen, such as bromine and chlorine, a hydroxyl group, a nitro group, an aminogroup, a carboxyl group, a sulfonic acid group or an ester group thereof.
Compounds described above which are preferably used are those in which the R
independently of one another are C1-C12-alkyl, C5-C10-cycloalkyl, C6-C12-aryl orC7-C13-alkaryl, in particular C1- to C3- substituted phenyl, the R2 independently of one another are -O-C1-C12-alkyl, -O-C5-C10-cycloalkyl or -O-C6-C12-aryl, the R3 independently of one another are hydrogen, C1-C2-alkyl, C5-C10-cycloalkyl or C6-C12-aryl, x is a number from 1 to 50 and z is a number from 1 to 8, It is particularly preferable to use compounds of the above formula in which R1 is C1-C6-alkyl, phenyl, naphthyl, benzyl, diphenyl, styryl or 1-phenylethyl, R2 is C1-C6-alkyl or phenyl and M is an alkali metal ion, mono-, di- or triethylammonium ion or triethanolammonium ion, x is a number from 3 to 10 and z is a number from 1 to 5.
The compounds described above can be used in the pure form or in mixtures of several such compounds.
- . CA 02214918 1997-09-09 The acyloxyalkylene group -(CHR4-CH2o)X- can be an oxyethylene or an oxypropylene group, as well as mixtures of oxyethylene and oxypropylene groups. In this case, the polyoxyalkylene group can contain the oxyethylene and oxypropylene units in random distribution, and closed blocks of oxyethylene and oxypropylene 5 units are also possible. The mixtures of the above formula in general comprise 0 to 50 oxyethylene units and 0 to 50 oxypropylene units, in which x is in each case at least 1. They preferably contain 0 to 25 oxyethylene units and 0 to 25 oxypropylene units, in particular 3 to 10 oxyethylene units and 3 to 10 oxypropylene units.
The compounds of the above formula are known from WO-94/10839 and from the other publications mentioned therein. The subject matter of this prior art is the use of the aryloxypolyglycol ethers in question as auxiliaries in plant protection formulations.
15 The abovementioned compounds can be employed by themselves or together with other leveling and dispersing agents or with other surfactants, builders and other customary additives and auxiliaries in dyebaths, padding baths and printing pastes for printing textiles and paper. The action of the compounds can be utilized in respect of the leveling action, the dispersing action or both actions. The two effects 20 together are of importance for the fastness and uniformity of the dyeing, for example on polyester, acetate, triacetate or polyamide fiber materials. The compounds can also be admixed during preparation of disperse dyestuffs, in order to comply with particularly high demands on fine division and stability of the dyestuff dispersions during dyeing in an alkaline medium.
As a liquid medium, the dyebaths and padding baths comprise, in particular, water, or if appropriate also organic solvents which boil at between 100~C and 290~C.
Solvents which may be mentioned as preferred are aromatic hydrocarbons, such as xylene, toluene, ethylbenzene and alkylated benzenes having on average 9 carbon 30 atoms, such as the solvent types known under the name ~DSolvesso (Esso Chemie GmbH) and dimethylnaphthalene, and furthermore halogenated aromatic hydrocarbons, such as chlorobenzenes, and in addition alcohols and ketones, suchas n-butanol, n-hexanol, iso-hexanol, n-octanol, cyclohexanol, benzyl alcohol and di-n-butyl ketone, and also ethers and esters.
As coloring agents, the dyebaths, padding baths and pastes comprise the compounds usually used and known for this purpose, in particular disperse 5 dyestuffs, or else optical brighteners. The amount of aryloxypolyglycol ether is 0.01 to 10 % by weight, based on the synthetic fiber. Mixtures of the aryloxypolyglycol ethers which differ in the nature of the radical R can also be used. The weight ratio of the two aryloxypolyglycol ethers in such mixtures can be 1:19 to 19:1, preferably 1 :4 to 4: 1 .
The dispersing and leveling agents of the present invention also show a reliabledispersing action in the pH range from pH 7.1 to 12, and are not impaired in their activity as dispersing and leveling auxiliaries by the alkali and by the heat (up to 140~C) of the treatment baths and dyebaths during the customary dyeing time of up 15 to 120 minutes.
The aryloxypolyglycol ethers described above can be diluted with water and as a result are also particularly suitable for the preparation of highly concentrated free-flowing dispersions of organic and inorganic coloring agents. Suitable coloring 20 agents are all sparingly soluble dyestuffs and pigments, such as vat dyestuffs and azo dyestuffs, but in particular disperse dyestuffs. These coloring agents are stirred, as press-cakes or in individual cases also in dried form, with the aryloxypolyglycol ethers of the invention or an aqueous solution thereof with as little water as possible in a dissolver (high-speed stirrer with a sawtooth disc) to give a pumpable 25 suspension, and if necessary the mixture is homogenized via a corundum disk mill or similar colloid mills, and is then in general ground to the desired fine division in a continuous stirrer mill with quartzite beads of 1 to 3 mm diameter, possibly in several passes. After grinding, as is also the case during stirring, further additions of bactericides, standardizing agents, such as, for example, sugar, further dispersing 30 agents and water for formulation of a paste can be made. To prepare a powder, a suitable paste is dried in a spray tower and then brought to the desired dry content.
The ratio of dispersing agent to coloring agent powder can vary within wide limits and is in general 0.3 to 10, preferably 0.5 to 2 parts by weight of dispersing agent per part of dyestuff powder.
5 Example 1:
Dyeing by the exhaust process Threads of polyester continuous material are wound onto dyeing centers and 10 treated in a dyebath in a package dyeing apparatus. The dyeing apparatus contains 10 1 of water per 1 kg of goods for dyeing. This bath comprises 3 9/l of sodium tetraborate 1 0-hydrate and 1 9/l of the leveling and dispersing agent of the formula /cH2-c6Hs CH3 o C6Hs-CH2 ~ 0--(CH2CH20)3--(CHCH20)3 p o K
CH2-C6Hs This treatment bath is pumped alternately from the inside outward and from the 15 outside inward through the packages at 60~C for a total of 10 minutes. This alternating direction of the dye liquor is maintained through the entire process, as long as the apparatus is filled. A uniform distribution of the auxiliary and thechemicals in the bath and in the goods to be dyed results from this initial running.
20 After this initial running, 2 % of the dyestuff (Color Index Disperse Yellow 160), calculated with respect to the weight of the threads, of the formula HO \~
is added to the treatment bath. For uniform distribution of the dyestuff, treatment is carried out with an alternating liquor direction, as described above, for 10 minutes.
S Thereafter, the treatment bath is heated up to 1 30~C at 0.5~C per minute by indirect heating. Dyeing is carried out at 1 30~C for 30 minutes, followed by cooling to 80~C
at 2~C per minute. The treatment bath is drained off at 80~C. The dyeing on the goods to be dyed is uniform and fast to rubbing. No dyestuff deposits occur on the metal components of the dyeing apparatus which come into contact with the 10 treatment bath or on the centers. Without the dispersing action of the auxiliary, a dyeing which is not fast to rubbing and deposits of the dyestuff on the metal components result. The dyeing on the goods to be dyed is furthermore uniform, ascan be seen by knitting the yarn on a knitting machine. No streaks or spots which could originate from weaker or stronger dyeing of the yarn occur. The threads show 15 no deposits of oligomers on the fiber surface. No after-cleaning at 80~C with dilute sodium hydroxide solution and sodium dithionite is necessary.
Example 2 20 Dyeing by the exhaust process in the presence of a lubricant.
50 kg of a woven fabric of polyester staple fiber yarn in the warp and weft, which has been cleaned from adhering size and spinning preparation by an industrial washing process, dried and fixed for 45 seconds at 1 80~C with hot air on a stenter, is loaded 25 into a dyeing machine for woven fabric. Thereafter, the start and end of the web of goods are sewn to one another, so that a continuous belt results. The dyeing machine contains 8 1 of water per 1 kg of goods to be dyed. The woven fabric is agitated in the dyeing machine by means of this dyebath, which is heated at 60~C, with the aid of a Venturi nozle. 1 g/l of a lubricating auxiliary as described in DE~A-2542051 (tradename: ~Emigen DPR), 5 g/l of calcined soda and 0.3 cm3/l of sodiumhydroxide solution (about pH 9.5) as well as 1 % of the auxiliary of the formula C6H5--CH2~0-(CH2CH20)3 1--o NH(c2Hs)3 ~(~) CH2-C6Hs 0~ NH(c2Hs)3 are added to this bath successively or simultaneously, as desired.
This treatment bath is agitated together with the woven fabric at 60~C for 10 minutes. Agitation of the woven fabric by the bath is maintained throughout the entire process, as long as the dyeing machine is filled. A uniform distribution of the auxiliary and the chemicals in the bath and in the goods to be dyed results from this initial running.
After this initial running, 0.75% of the dyestuff (Color Index Disperse Blue 60), calculated with respect to the weight of the woven fabric, of the formula .
~ ~ ~ O-CH3 is added to the treatment bath. The woven fabric is agitated by means of the liquor for 10 minutes, as described above, for uniform distribution of the dyestuff.
Thereafter, the treatment bath is heated up to 1 30~C at 1 .0~C per minute by indirect heating. Dyeing is carried out at 130~C for 30 minutes, followed by cooling to 60~C
at 2~C/minute. The treatment bath is drained off at 60~C. The dyeing on the goods 5 to be dyed is uniform and fast to rubbing. No weaker or stronger dyeings of the woven fabric in the warp and weft directions occur.
Example 3:
10 Dyeing of the polyester fiber portion of blend fabrics by the exhaust process A woven fabric with a weight of 40 kg of a yarn in the warp and weft which comprises a mixture of 50 percent by weight of polyester staple fiber and 50 percent by weight of cotton was used. The woven fabric was subjected to an industrial 15 washing and bleaching process to remove adhering size, spinning preparations and the naturally occurring concomitant substances of cotton. Thereafter, it was dried and fixed for 60 seconds at 1 70~C with hot air on a stenter. For dyeing, the blend fabric was loaded into a dyeing machine and the start was sown to the end of theweb of goods so that a continuous belt results. The dyeing machine contained 81 of 20 water per 1 kg of goods to be dyed. The woven fabric was agitated in the dyeing machine by means of this dyebath, which was heated at 60~C, with the aid of a Venturi nozle. 1 percent by weight, calculated with respect to the weight of thewoven fabric, of a lubricant from Hoechst AG (E9Humectol C) and 0.02 g/l of - trisodium phosphate 12-hydrate and 2 g/l of disodium hydrogen phosphate 12-25 hydrate (about pH 9.5) as well as 1% of the auxiliary of the formula given inExample 1 were added to this bath successively or simultaneously, as desired.
This treatment bath was agitated in the dyeing machine together with the woven fabric for 10 minutes at 60~C. The agitation of the woven fabric by the bath was30 maintained throughout the entire process, as long as the dyeing machine is filled. A
uniform distribution of the auxiliary and of the chemicals in the bath and in the goods to be dyed results from this initial running.
- . CA 02214918 1997-09-09 After this initial running, 0.5 % of the dyestuff, calculated with respect to the weight of the woven fabric, of the formula from Example 1 was added to the treatment bath.
For uniform distribution of the dyestuff, the woven fabric was agitated by means of the liquor for 10 minutes, as described above. Thereafter, the treatment bath was S heated up to 125~C at 1~C per minute by indirect heating, and dyeing was carried out at 125~C for 60 minutes, followed by cooling to 60~C at 2~C per minute. The treatment bath was drained off at 60~C. The dyeing on the woven fabric is uniform and fast to rubbing on the polyester fiber portion, and the cotton fiber is free of dyestuff.Example 4 31 parts by weight of the dyestuff of the formula J ~ J = OCH3 (Color Index Disperse Blue 73) in the form of an aqueous press-cake are ground 15 with 18 parts by weight of sodium dinaphthylmethanesulfonate (Tamol NNO), 0.3 part by weight of a biocide, 6 parts by weight of the auxiliary according to the invention from Example 1 and 50.7 parts by weight of water (minus the varying residual amount of water of the aqueous press-cake) in a bead mill until the particle size is below 1 ,um. The formulation has low viscosity and is stable on storage. In 20 the dyeing of wound packages, a uniform dyeing with good fastness to rubbing and without dyestuff filter effect is obtained.
Example 5:
Dyeing by the exhaust process 5 Threads of polyester continuous material are wound on dyeing centers and treated in a dyebath in a package dyeing apparatus. The dyeing apparatus contains 101 ofwater per 1 kg of goods to be dyed. This bath comprises 3 g/l of sodium tetraborate 10-hydrate and 1 g/l of the leveling and dispersing agent of the formula C6H5-CH2 ~ ~ (CH2CH20)3 (CHCH20)3 P-O K
cH2-c6H5 ~ ) c3 K
10 This treatment bath is pumped alternately from the inside outward and from the outside inward through the packages at 60~C for a total of 10 minutes. This alternating direction of the dye liquor is maintained throughout the entire process, as long as the apparatus is filled. A uniform distribution of the auxiliary and thechemicals in the bath and in the goods to be dyed results from this initial running.
After this initial running, 2 % of the dyestuff (Color Index Disperse Yellow 160), calculated with respect to the weight of the threads, of the formula Br ~'4~
,V~
HO Q.~
is added to the treatment bath. For uniform distribution of the dyestuff, treatment is carried out with an alternating liquor direction for 10 minutes, as described above.
Thereafter, the treatment bath is heated up to 1 30~C at 0.5~C per minute by indirect heating. Dyeing is carried out at 1 30~C for 30 minutes, followed by cooling to 80~C
5 at 2~C per minute. The treatment bath is drained off at 80~C. The dyeing on the goods to be dyed is uniform and fast to rubbing. No dyestuff deposits occur on the metal components of the dyeing apparatus which come into contact with the treatment bath or on the centers. Without the dispersing action of the auxiliary, a dyeing which is not fast to rubbing and deposits of the dyestuff on the metal 10 components result. Furthermore, the dyeing on the goods to be dyed is uniform, as can be seen by knitting the yarn on a knitting machine. No streaks or spots which could originate from weaker or stronger dyeing of the yarn occur. The threads show no deposits of oligomers on the fiber surface. After-cleaning at 80~C with dilute sodium hydroxide solution and sodium dithionite is not necessary.
Dyeing in an alkaline bath at pH 7.1 to pH 12, preferably at pH 8.5 to 10, however, 20 is advantageous because oligomers from the polyester fiber are not deposited or are deposited hardly at all on the fiber surface in the form of crystals. This is a great advantage during further processing of polyester fibers, because a hot alkaline treatment to remove the oligomers, which is carried out with sodium hydroxide solution and sodium dithionite at 80 to 100~~, can be omitted. The oligomers are-25 still not removed completely enough by this treatment, and in addition an undesirable shift in the hue of the dyeing can take place.
Furthermore, during dyeing in an alkaline pH range at temperatures of 90 to 140~C, commercially available leveling and dispersing agents are often split by hydrolysis 30 and therefore become ineffective. It has been found, surprisingly, that the auxiliaries described below are effective as leveling and dispersing agents in an alkaline dyebath, and that dyeings are obtained without differences in respect of color strength and without color shade differences in combination dyeings, regardless of whether the dyeings are on sheet-like structures, yarns, threads or non-spun - CA 022l49l8 l997-09-09 material.
The invention relates to the use of aryloxypolyglycol ethers of the formula (R )3 R4 ~ o- (CH - CH2 - ~) x~ R
10 in which R is hydrogen or a group of the formulae o o ~
P--R . --P--OM, --p OM or ~ OM
R 2 1 2 OM o where sulfonic acid esters are used only in the pH range from 7.1 to 12, the R1 independently of one another are hydrogen, C1-C24-alkyl, C5-C15-cycloalkyl~ C6-C24-aryl, C7-C24-alkaryl or (CH2)zaryl, the R2 independently of one another are -OH, -O-C1-C24-alkyl, -O-C5-C,5-cycloalkyl, -O-C6-C18-aryl or a group of the formula (R1)3 R4 ~ O - (CH - CH2-O)X-M is an alkali metal ion, alkaline earth metal ion or ammonium ion of the formula N(R3)4, the R3 independently of one another are hydrogen, C1-C4-alkyl, C5-C15-cycloalkyl, C6-C18-aryl or a group of the formula -(CH2)zOH, R4 is hydrogen or methyl, x is a number from 1 to 100 and z is a number from 1 to 10, as leveling and dispersing agents.
The radicals R1, R2 and R3 are optionally substituted. Suitable substituents arehalogen, such as bromine and chlorine, a hydroxyl group, a nitro group, an aminogroup, a carboxyl group, a sulfonic acid group or an ester group thereof.
Compounds described above which are preferably used are those in which the R
independently of one another are C1-C12-alkyl, C5-C10-cycloalkyl, C6-C12-aryl orC7-C13-alkaryl, in particular C1- to C3- substituted phenyl, the R2 independently of one another are -O-C1-C12-alkyl, -O-C5-C10-cycloalkyl or -O-C6-C12-aryl, the R3 independently of one another are hydrogen, C1-C2-alkyl, C5-C10-cycloalkyl or C6-C12-aryl, x is a number from 1 to 50 and z is a number from 1 to 8, It is particularly preferable to use compounds of the above formula in which R1 is C1-C6-alkyl, phenyl, naphthyl, benzyl, diphenyl, styryl or 1-phenylethyl, R2 is C1-C6-alkyl or phenyl and M is an alkali metal ion, mono-, di- or triethylammonium ion or triethanolammonium ion, x is a number from 3 to 10 and z is a number from 1 to 5.
The compounds described above can be used in the pure form or in mixtures of several such compounds.
- . CA 02214918 1997-09-09 The acyloxyalkylene group -(CHR4-CH2o)X- can be an oxyethylene or an oxypropylene group, as well as mixtures of oxyethylene and oxypropylene groups. In this case, the polyoxyalkylene group can contain the oxyethylene and oxypropylene units in random distribution, and closed blocks of oxyethylene and oxypropylene 5 units are also possible. The mixtures of the above formula in general comprise 0 to 50 oxyethylene units and 0 to 50 oxypropylene units, in which x is in each case at least 1. They preferably contain 0 to 25 oxyethylene units and 0 to 25 oxypropylene units, in particular 3 to 10 oxyethylene units and 3 to 10 oxypropylene units.
The compounds of the above formula are known from WO-94/10839 and from the other publications mentioned therein. The subject matter of this prior art is the use of the aryloxypolyglycol ethers in question as auxiliaries in plant protection formulations.
15 The abovementioned compounds can be employed by themselves or together with other leveling and dispersing agents or with other surfactants, builders and other customary additives and auxiliaries in dyebaths, padding baths and printing pastes for printing textiles and paper. The action of the compounds can be utilized in respect of the leveling action, the dispersing action or both actions. The two effects 20 together are of importance for the fastness and uniformity of the dyeing, for example on polyester, acetate, triacetate or polyamide fiber materials. The compounds can also be admixed during preparation of disperse dyestuffs, in order to comply with particularly high demands on fine division and stability of the dyestuff dispersions during dyeing in an alkaline medium.
As a liquid medium, the dyebaths and padding baths comprise, in particular, water, or if appropriate also organic solvents which boil at between 100~C and 290~C.
Solvents which may be mentioned as preferred are aromatic hydrocarbons, such as xylene, toluene, ethylbenzene and alkylated benzenes having on average 9 carbon 30 atoms, such as the solvent types known under the name ~DSolvesso (Esso Chemie GmbH) and dimethylnaphthalene, and furthermore halogenated aromatic hydrocarbons, such as chlorobenzenes, and in addition alcohols and ketones, suchas n-butanol, n-hexanol, iso-hexanol, n-octanol, cyclohexanol, benzyl alcohol and di-n-butyl ketone, and also ethers and esters.
As coloring agents, the dyebaths, padding baths and pastes comprise the compounds usually used and known for this purpose, in particular disperse 5 dyestuffs, or else optical brighteners. The amount of aryloxypolyglycol ether is 0.01 to 10 % by weight, based on the synthetic fiber. Mixtures of the aryloxypolyglycol ethers which differ in the nature of the radical R can also be used. The weight ratio of the two aryloxypolyglycol ethers in such mixtures can be 1:19 to 19:1, preferably 1 :4 to 4: 1 .
The dispersing and leveling agents of the present invention also show a reliabledispersing action in the pH range from pH 7.1 to 12, and are not impaired in their activity as dispersing and leveling auxiliaries by the alkali and by the heat (up to 140~C) of the treatment baths and dyebaths during the customary dyeing time of up 15 to 120 minutes.
The aryloxypolyglycol ethers described above can be diluted with water and as a result are also particularly suitable for the preparation of highly concentrated free-flowing dispersions of organic and inorganic coloring agents. Suitable coloring 20 agents are all sparingly soluble dyestuffs and pigments, such as vat dyestuffs and azo dyestuffs, but in particular disperse dyestuffs. These coloring agents are stirred, as press-cakes or in individual cases also in dried form, with the aryloxypolyglycol ethers of the invention or an aqueous solution thereof with as little water as possible in a dissolver (high-speed stirrer with a sawtooth disc) to give a pumpable 25 suspension, and if necessary the mixture is homogenized via a corundum disk mill or similar colloid mills, and is then in general ground to the desired fine division in a continuous stirrer mill with quartzite beads of 1 to 3 mm diameter, possibly in several passes. After grinding, as is also the case during stirring, further additions of bactericides, standardizing agents, such as, for example, sugar, further dispersing 30 agents and water for formulation of a paste can be made. To prepare a powder, a suitable paste is dried in a spray tower and then brought to the desired dry content.
The ratio of dispersing agent to coloring agent powder can vary within wide limits and is in general 0.3 to 10, preferably 0.5 to 2 parts by weight of dispersing agent per part of dyestuff powder.
5 Example 1:
Dyeing by the exhaust process Threads of polyester continuous material are wound onto dyeing centers and 10 treated in a dyebath in a package dyeing apparatus. The dyeing apparatus contains 10 1 of water per 1 kg of goods for dyeing. This bath comprises 3 9/l of sodium tetraborate 1 0-hydrate and 1 9/l of the leveling and dispersing agent of the formula /cH2-c6Hs CH3 o C6Hs-CH2 ~ 0--(CH2CH20)3--(CHCH20)3 p o K
CH2-C6Hs This treatment bath is pumped alternately from the inside outward and from the 15 outside inward through the packages at 60~C for a total of 10 minutes. This alternating direction of the dye liquor is maintained through the entire process, as long as the apparatus is filled. A uniform distribution of the auxiliary and thechemicals in the bath and in the goods to be dyed results from this initial running.
20 After this initial running, 2 % of the dyestuff (Color Index Disperse Yellow 160), calculated with respect to the weight of the threads, of the formula HO \~
is added to the treatment bath. For uniform distribution of the dyestuff, treatment is carried out with an alternating liquor direction, as described above, for 10 minutes.
S Thereafter, the treatment bath is heated up to 1 30~C at 0.5~C per minute by indirect heating. Dyeing is carried out at 1 30~C for 30 minutes, followed by cooling to 80~C
at 2~C per minute. The treatment bath is drained off at 80~C. The dyeing on the goods to be dyed is uniform and fast to rubbing. No dyestuff deposits occur on the metal components of the dyeing apparatus which come into contact with the 10 treatment bath or on the centers. Without the dispersing action of the auxiliary, a dyeing which is not fast to rubbing and deposits of the dyestuff on the metal components result. The dyeing on the goods to be dyed is furthermore uniform, ascan be seen by knitting the yarn on a knitting machine. No streaks or spots which could originate from weaker or stronger dyeing of the yarn occur. The threads show 15 no deposits of oligomers on the fiber surface. No after-cleaning at 80~C with dilute sodium hydroxide solution and sodium dithionite is necessary.
Example 2 20 Dyeing by the exhaust process in the presence of a lubricant.
50 kg of a woven fabric of polyester staple fiber yarn in the warp and weft, which has been cleaned from adhering size and spinning preparation by an industrial washing process, dried and fixed for 45 seconds at 1 80~C with hot air on a stenter, is loaded 25 into a dyeing machine for woven fabric. Thereafter, the start and end of the web of goods are sewn to one another, so that a continuous belt results. The dyeing machine contains 8 1 of water per 1 kg of goods to be dyed. The woven fabric is agitated in the dyeing machine by means of this dyebath, which is heated at 60~C, with the aid of a Venturi nozle. 1 g/l of a lubricating auxiliary as described in DE~A-2542051 (tradename: ~Emigen DPR), 5 g/l of calcined soda and 0.3 cm3/l of sodiumhydroxide solution (about pH 9.5) as well as 1 % of the auxiliary of the formula C6H5--CH2~0-(CH2CH20)3 1--o NH(c2Hs)3 ~(~) CH2-C6Hs 0~ NH(c2Hs)3 are added to this bath successively or simultaneously, as desired.
This treatment bath is agitated together with the woven fabric at 60~C for 10 minutes. Agitation of the woven fabric by the bath is maintained throughout the entire process, as long as the dyeing machine is filled. A uniform distribution of the auxiliary and the chemicals in the bath and in the goods to be dyed results from this initial running.
After this initial running, 0.75% of the dyestuff (Color Index Disperse Blue 60), calculated with respect to the weight of the woven fabric, of the formula .
~ ~ ~ O-CH3 is added to the treatment bath. The woven fabric is agitated by means of the liquor for 10 minutes, as described above, for uniform distribution of the dyestuff.
Thereafter, the treatment bath is heated up to 1 30~C at 1 .0~C per minute by indirect heating. Dyeing is carried out at 130~C for 30 minutes, followed by cooling to 60~C
at 2~C/minute. The treatment bath is drained off at 60~C. The dyeing on the goods 5 to be dyed is uniform and fast to rubbing. No weaker or stronger dyeings of the woven fabric in the warp and weft directions occur.
Example 3:
10 Dyeing of the polyester fiber portion of blend fabrics by the exhaust process A woven fabric with a weight of 40 kg of a yarn in the warp and weft which comprises a mixture of 50 percent by weight of polyester staple fiber and 50 percent by weight of cotton was used. The woven fabric was subjected to an industrial 15 washing and bleaching process to remove adhering size, spinning preparations and the naturally occurring concomitant substances of cotton. Thereafter, it was dried and fixed for 60 seconds at 1 70~C with hot air on a stenter. For dyeing, the blend fabric was loaded into a dyeing machine and the start was sown to the end of theweb of goods so that a continuous belt results. The dyeing machine contained 81 of 20 water per 1 kg of goods to be dyed. The woven fabric was agitated in the dyeing machine by means of this dyebath, which was heated at 60~C, with the aid of a Venturi nozle. 1 percent by weight, calculated with respect to the weight of thewoven fabric, of a lubricant from Hoechst AG (E9Humectol C) and 0.02 g/l of - trisodium phosphate 12-hydrate and 2 g/l of disodium hydrogen phosphate 12-25 hydrate (about pH 9.5) as well as 1% of the auxiliary of the formula given inExample 1 were added to this bath successively or simultaneously, as desired.
This treatment bath was agitated in the dyeing machine together with the woven fabric for 10 minutes at 60~C. The agitation of the woven fabric by the bath was30 maintained throughout the entire process, as long as the dyeing machine is filled. A
uniform distribution of the auxiliary and of the chemicals in the bath and in the goods to be dyed results from this initial running.
- . CA 02214918 1997-09-09 After this initial running, 0.5 % of the dyestuff, calculated with respect to the weight of the woven fabric, of the formula from Example 1 was added to the treatment bath.
For uniform distribution of the dyestuff, the woven fabric was agitated by means of the liquor for 10 minutes, as described above. Thereafter, the treatment bath was S heated up to 125~C at 1~C per minute by indirect heating, and dyeing was carried out at 125~C for 60 minutes, followed by cooling to 60~C at 2~C per minute. The treatment bath was drained off at 60~C. The dyeing on the woven fabric is uniform and fast to rubbing on the polyester fiber portion, and the cotton fiber is free of dyestuff.Example 4 31 parts by weight of the dyestuff of the formula J ~ J = OCH3 (Color Index Disperse Blue 73) in the form of an aqueous press-cake are ground 15 with 18 parts by weight of sodium dinaphthylmethanesulfonate (Tamol NNO), 0.3 part by weight of a biocide, 6 parts by weight of the auxiliary according to the invention from Example 1 and 50.7 parts by weight of water (minus the varying residual amount of water of the aqueous press-cake) in a bead mill until the particle size is below 1 ,um. The formulation has low viscosity and is stable on storage. In 20 the dyeing of wound packages, a uniform dyeing with good fastness to rubbing and without dyestuff filter effect is obtained.
Example 5:
Dyeing by the exhaust process 5 Threads of polyester continuous material are wound on dyeing centers and treated in a dyebath in a package dyeing apparatus. The dyeing apparatus contains 101 ofwater per 1 kg of goods to be dyed. This bath comprises 3 g/l of sodium tetraborate 10-hydrate and 1 g/l of the leveling and dispersing agent of the formula C6H5-CH2 ~ ~ (CH2CH20)3 (CHCH20)3 P-O K
cH2-c6H5 ~ ) c3 K
10 This treatment bath is pumped alternately from the inside outward and from the outside inward through the packages at 60~C for a total of 10 minutes. This alternating direction of the dye liquor is maintained throughout the entire process, as long as the apparatus is filled. A uniform distribution of the auxiliary and thechemicals in the bath and in the goods to be dyed results from this initial running.
After this initial running, 2 % of the dyestuff (Color Index Disperse Yellow 160), calculated with respect to the weight of the threads, of the formula Br ~'4~
,V~
HO Q.~
is added to the treatment bath. For uniform distribution of the dyestuff, treatment is carried out with an alternating liquor direction for 10 minutes, as described above.
Thereafter, the treatment bath is heated up to 1 30~C at 0.5~C per minute by indirect heating. Dyeing is carried out at 1 30~C for 30 minutes, followed by cooling to 80~C
5 at 2~C per minute. The treatment bath is drained off at 80~C. The dyeing on the goods to be dyed is uniform and fast to rubbing. No dyestuff deposits occur on the metal components of the dyeing apparatus which come into contact with the treatment bath or on the centers. Without the dispersing action of the auxiliary, a dyeing which is not fast to rubbing and deposits of the dyestuff on the metal 10 components result. Furthermore, the dyeing on the goods to be dyed is uniform, as can be seen by knitting the yarn on a knitting machine. No streaks or spots which could originate from weaker or stronger dyeing of the yarn occur. The threads show no deposits of oligomers on the fiber surface. After-cleaning at 80~C with dilute sodium hydroxide solution and sodium dithionite is not necessary.
Claims (5)
1. The use of an aryloxypolyglycol ether of the formula in which R is hydrogen or a group of the formulae , , or where sulfonic acid esters are used only in the pH range from 7.1 to 12, the R1 independently of one another are hydrogen, C1-C24-alkyl, C5-C15 cycloalkyl, C6-C24-aryl, C7-C24-alkaryl or (CH2)z aryl, the R2 independently of one another are -OH, -O-C1-C24-alkyl, -O-C5-C15-cycloalkyl, -O-C6-C18-aryl or a group of the formula M is an alkali metal ion, alkaline earth metal ion or ammonium ion of the formula N(R3)4, the R3 independently of one another are hydrogen, C1-C4-alkyl, C5-C15-cycloalkyl, C6-C18-aryl or a group of the formula -(CH2)zOH, R4 is hydrogen or methyl, x is a number from 1 to 100 and z is a number from 1 to 10, as leveling and dispersing agent.
2. The use of an aryloxypolyglycol ether as claimed in claim 1, in which the R1 independently of one another are C1-C12-alkyl, C5-C10-cycloalkyl, C6-C12-aryl or C7-C13-alkaryl, the R2 independently of one another are -O-C1-C12-alkyl, -O-C5-C10-cycloalkyl or-O-C6-C12-aryl, the R3 independently of one another are hydrogen, C1-C2-alkyl, C5-C10-cycloalkyl or C6-C12-aryl, x is a number from 1 to 50 and z is a number from 1 to 8.
3. The use of an aryloxypolyglycol ether as claimed in one of claims 1 or 2, in which the R1 independently of one another are C1-C6-alkyl, phenyl, naphthyl, benzyl, diphenyl, styryl, 1-phenylethyl or C1- to C3-substituted phenyl, the R2 independently of one another are -O-C1-C6-alkyl or-O-phenyl, and M is a potassium ion, mono-, di- or triethylammonium ion or a triethanolammonium ion, x is a number from 3 to 10 and z is a number from 1 to 5.
4. The use of an aryloxypolyglycol ether as claimed in one or more of claims 1 to 3, wherein a mixture of aryloxypolyglycol ethers is used.
5. A dyebath, padding bath or paste for printing textiles and printing paper, comprising an aryloxypolyglycol ether as claimed in one or more of claims 1 to 3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19638566.0 | 1996-09-20 | ||
| DE19638566A DE19638566A1 (en) | 1996-09-20 | 1996-09-20 | Use of aryloxypolyglycol ethers as leveling and dispersing agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2214918A1 true CA2214918A1 (en) | 1998-03-20 |
Family
ID=7806334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002214918A Abandoned CA2214918A1 (en) | 1996-09-20 | 1997-09-09 | Use of aryloxypolyglycol ethers as levelling and dispersing agents |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0831167A3 (en) |
| JP (1) | JPH10121380A (en) |
| KR (1) | KR19980024724A (en) |
| AR (1) | AR008441A1 (en) |
| AU (1) | AU3754497A (en) |
| BR (1) | BR9704754A (en) |
| CA (1) | CA2214918A1 (en) |
| DE (1) | DE19638566A1 (en) |
| ID (1) | ID18310A (en) |
| TR (1) | TR199700980A2 (en) |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1469603A1 (en) * | 1964-06-11 | 1969-08-28 | Basf Ag | Process for drying and fixing of basic dyes padded onto fibers containing acrylonitrile polymers or consisting thereof, using dry heat |
| DE1619658A1 (en) * | 1967-02-15 | 1971-02-25 | Basf Ag | Aid for printing flat fiber material |
| JPS5058376A (en) * | 1973-09-22 | 1975-05-21 | ||
| JPS50148679A (en) * | 1974-05-23 | 1975-11-28 | ||
| US4192648A (en) * | 1977-09-12 | 1980-03-11 | Gaf Corporation | Cationic dye carrier and selective process for dyeing polyesters |
| DE2745449C2 (en) * | 1977-10-08 | 1979-10-25 | Basf Ag, 6700 Ludwigshafen | Stable finely divided aqueous preparations of disperse dyes and optical brighteners and their use |
| GB2090876A (en) * | 1981-01-14 | 1982-07-21 | Ici Plc | Aqueous Dispersions for Textile Dyeing |
| DE3133739A1 (en) * | 1981-08-26 | 1983-03-10 | Bayer Ag, 5090 Leverkusen | Carrier formulations and use thereof in the single-bath dyeing of polyester- and cellulose-containing materials |
| DE59006864D1 (en) * | 1989-02-08 | 1994-09-29 | Ciba Geigy Ag | Auxiliary mixture and its use in dyeing synthetic fiber materials. |
| EP0414631A1 (en) * | 1989-02-22 | 1991-02-27 | Ciba-Geigy Ag | Auxiliary agent mixture and its use in dyeing polyester fibre materials |
| DE4317075A1 (en) * | 1993-05-21 | 1994-11-24 | Bayer Ag | Dyeing aids containing lithium for dyeing and printing |
-
1996
- 1996-09-20 DE DE19638566A patent/DE19638566A1/en not_active Withdrawn
-
1997
- 1997-09-09 CA CA002214918A patent/CA2214918A1/en not_active Abandoned
- 1997-09-12 AU AU37544/97A patent/AU3754497A/en not_active Abandoned
- 1997-09-15 EP EP97116005A patent/EP0831167A3/en not_active Withdrawn
- 1997-09-18 JP JP9253659A patent/JPH10121380A/en not_active Withdrawn
- 1997-09-18 AR ARP970104289A patent/AR008441A1/en unknown
- 1997-09-18 TR TR97/00980A patent/TR199700980A2/en unknown
- 1997-09-18 ID IDP973222A patent/ID18310A/en unknown
- 1997-09-19 BR BR9704754A patent/BR9704754A/en not_active Application Discontinuation
- 1997-09-19 KR KR1019970047634A patent/KR19980024724A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR008441A1 (en) | 2000-01-19 |
| ID18310A (en) | 1998-03-26 |
| EP0831167A3 (en) | 1998-08-12 |
| JPH10121380A (en) | 1998-05-12 |
| TR199700980A2 (en) | 1998-04-21 |
| EP0831167A2 (en) | 1998-03-25 |
| DE19638566A1 (en) | 1998-03-26 |
| BR9704754A (en) | 1998-11-10 |
| KR19980024724A (en) | 1998-07-06 |
| AU3754497A (en) | 1998-03-26 |
| MX9707165A (en) | 1998-12-31 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |