US3362780A - Process for dyeing textile materials - Google Patents

Process for dyeing textile materials Download PDF

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US3362780A
US3362780A US350685A US35068564A US3362780A US 3362780 A US3362780 A US 3362780A US 350685 A US350685 A US 350685A US 35068564 A US35068564 A US 35068564A US 3362780 A US3362780 A US 3362780A
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mol
dyeing
dyestuffs
textile materials
acid
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US350685A
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Robert Kuth
Otto Schneider
Mathieu Quaedvlieg
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/70—Material containing nitrile groups
    • D06P3/72—Material containing nitrile groups using dispersed dyestuffs

Definitions

  • the present invention relates to a process wherein textile materials are dyed in such a manner that the dyestufis are padded or printed in the form of solutions or suspensions and subsequently fixed by heating; reference may be made, for example, to the Thermosol process described in American Dyestuff Reporter, 1949, page 593. More particularly the present invention concerns a process wherein such a padding or printing of textile materials is carried out in the presence of water-soluble reaction products of aromatic, hydroaromatic or aliphatic monoor poly-isocyanates with high-molecular hydroxy-alkylation products of compounds which contain at least 8 carbon atoms and possess only one single hydrogen atom capable of reacting with alkylene oxides.
  • reaction products to be used according to the invention contain at least once the grouping wherein R means an alkylene radical containing two to four carbon atoms, and X stands for the radical of a compound which contains at least 8 carbon atom and possesses only one single hydrogen atom capable of reacting with alkylene oxides, while n is a number between and 200.
  • Suitable reaction products can be obtained, for example, by reacting at about 5070 C. ethyl isocyanate, stearyl isocyanate, phenyl isocyanate, toluylene diisocyanate, hexamethylene diisocyanate, l,4-diisocyanato-cyclohexane, 4,4-diisocyanato-dicyclohexylmethane, 4,4'-diisocyanato-diphenylmethane, w,w' diisocyanato-dimethylbenzene or 4,4',4"-triisocyanato-triphenylmethane with hydroxy-alkylation products which are prepared by the addi.
  • alklene oxides such as ethylene oxide or propylene oxide
  • monohydric alcohols or carboxylic acids containing at least 8 carbon atoms such as especially lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, hydroabietyl alcohol or lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, abietic acid and naphthenic acids, furthermore isohexyl phenol, heptyl phenol, nonyl phenol, dodecyl phenol or dodecyl mercaptan as well as secondary monoarnines, such as methyl stearyl amine.
  • the textile materials which are to be dyed or printed by the process according to the invention may be based on the most varied synthetic products, for example polyarnides, such as polycaprolactam, polyadipic acid, furamethylene diamide and polyamino-undecanic acid, furthermore polyurethanes or polyesters, such as those from terephthalic acid and ethylene glycol or 1,4-dimethylol cyclohexane, as well as especially polyacrylonitrile and copolymers of acrylonitrile with other vinyl compounds, for example acrylic acid esters, acrylic acid amides, vinylpyridine, vinyl chloride and vinylidene chloride.
  • polyarnides such as polycaprolactam, polyadipic acid, furamethylene diamide and polyamino-undecanic acid
  • polyurethanes or polyesters such as those from terephthalic acid and ethylene glycol or 1,4-dimethylol cyclohexane
  • the process according to the present invention comprises the dyeing or printing of those textile materials which are produced from cellulose esters, for example from cellulose triacetate or butyrate.
  • the process according to the present invention can also be applied to mixed fabrics of synthetic fibers or to mixed fabrics of synthetic fibers with fibers of native origin, such as wool or cotton, for example.
  • dyestuffs can also be employed in the present case, for example dispersion dyestuffs, vat dyestuffs, acid wool dyestuffs, metal complex dyestutfs or basic dyestuffs.
  • Mixed fabrics can be dyed, with a suitable choice of dyestuffs, according to a single or multiple bath process possibly with insertion of an exhaust process, or selectively, if desired.
  • reaction products to be used according to the invention are in general employed in amounts of 01-10%, preferably in amounts of 0.25.0%, referred to the dye liquor or printing paste, in the form of solutions or dispersions; they may, however, also be admixed in suitable concentrations to the dyestuffs.
  • nonionic emulsifiers such as hydroxy-alkylation products of fatty alcohols, fatty acids, naphthenic acids, of abietic acid or polyaryl-, alkylaryland alkylphenols, as well as ionic emulsifiers such as alkylaryl or alkyl sulphonates, can be used as dispersing agents.
  • the reaction products to be employed according to the present invention ensure an even distribution of the dyestuffs before and after fixation; they prevent two-sidedness and selvedge runnings of the dyeings and impart a pleasant handle to the textile materials; moreover they substantially increase the dyestufi yield, render a satisfactory dyeing possible even when several dyestuffs are used and enable the fixation temperature to be kept lower by 10- 20 C. or the duration of fixing correspondingly shorter than is customary with the Thermosol process mentioned in the beginning.
  • the use of thickening agents otherwise necessary which may cause the machine aggregates to become sticky can be dispensed with.
  • other assistants may also be added to the dye liquors, e.g., softening agents, carriers, antistatic compounds and also hydrotopic agents for increasing the solubility of the dyestuffs.
  • reaction products to be used according to the present invention are distinguished by the fact that a still higher dyestulf yield can be achieved by their use.
  • EXAMPLE 1 A fabric of polyacrylonitrile threads is impregnated on the foulard with a liquor which contains per litre 20 g. of the dyestuff (a) and 20 g. of the product obtained by reaction of 1 mol of 2,4-toluylene diisocyanate with 1 mol each of the hydroxy-alkylation products which were produced by the addition of mol of ethylene oxide on 1 mol of stearyl alcohol and by the addition of 170 mol of ethylene oxide on 1 mol of stearic acid.
  • the fabric is then squeezed off to a weight increase of about 80% and dried at 80140 C.
  • the fabric is subsequently treated in a tenter frame at ISO- C. for 45 seconds with hot air, then rinsed, washed and dried.
  • the brilliant yellow dyeing 3 obtained on the fabric is distinguished by excellent levelness, a very high efiiciency of the dyestufi and outstanding fastness.
  • a liquor which contains, instead of g. of the polymethine dyestuff (a), 20 g. of the azo dyestufi (b) or 20 g. of the anthraquinone dyestuflf (c), a red dyeing or a blue dyeing of similar properties is obtained.
  • EXAMPLE 2 A fabric of polycaprolactam is dyed, as described in Example 1, with a liquor which contains per litre 50 g. of the acid dyestutf (d) and, 20 g. of the product obtained by the reaction of 1 mol of 1,4-diisocyanato-cyclohexane with 1 mol each of the hydroxy-alkylation products prepared by the addition of 130 mol of ethylene oxide on 1 mol of stearyl alcohol and by the addition of mol of ethylene oxide on 1 mol of abietic acid. With a high efficiency of the dyestuii a uniform blue dyeing is obtained.
  • EXAMPLE 3 Knitted material of polycaprolactam or nylon is dyed, as described in Example 1, with a liquor containing per litre g. of the chromium complex of the dyestuff (e) and 20 g. of the product which was obtained by reacting at C. 1 mol of 4,4-diisocyanato-dicyclohexyl methane with 1 mol each of the hydroxy-alkylation products produced by the addition of 130 mol of ethylene oxide on 1 mol of oleyl alcohol and by the addition of 130 mol of ethylene oxide on 1 mol of oleic acid.
  • the red dyeing obtained is distinguished by excellent general fastness properties. Dyeings of similar properties in yellow and blue shades are obtained by employing, instead of the dyestuff (e), the chromium complexes of the dyestuffs (f) or (g).
  • EXAMPLE 4 A fabric of polycaprolactam fibers is treated, as described in Example 1, with 'a liquor which contains per litre 40 g. of the dispersion dyestufi (h) and 10g. of the product obtained by the reaction of 1 mol of 2,4-toluylene diisocyanate with 1 mol each of the hydroxy-alkylation products produced by the addition of 130 mol of ethylene oxide on 1 mol of nonylphenol and by the addition of mol of ethylene oxide on 1 mol of lauric acid. A brilliant blue dyeing with good fastness properties and good levelness is obtained.
  • EXAMPLE 5 A fabricg of polyethylene terephthalate fibers is dyed according to the instructions of Example 1 with a liquor which contains per litre 20 g. of the dyestuif (h) and 20 g. of one of the products obtained by the reaction of 1 mol of 2,4-toluylene diisocyanate with 1 or 2 mol of the hydroxy-alkylation product obtained by the addition of mol of ethylene oxide on 1 mol of oleyl alcohol.
  • a uniform blue dyeing is obtained with a dyestuif efiiciency of more than 92% If, under otherwise equal conditions, the dispersion dyestuif (i) is employed instead of the dyestufi (h), then a red dyeing is obtained which is distinguished by a high levelncss and fastness to sublimation.
  • reaction product is the product obtained by reacting (a) a first component selected from the group consisting of alkyl isocyanate, phenyl isocyanate, toluylene diisocyanate, hexamethylene diisocyanate, 1,4-diisocyanate-cyclohexane, 4,4-diisocyanate-dicyclohexylmethane, 4,4'-diisocyanate diphenylmethane, w,w'-diisocyanate-dimethylbenzene and triisocyanate-triphenylmethane with (b) the reaction product of allrylene oxide with a monohydric alcohol, alkyl phenol, alkyl mercaptan or secondary monoamine effecting the reaction of (a) and (b) at a temperature of about 5070 C.
  • a first component selected from the group consisting of alkyl isocyanate, phenyl isocyanate, toluylene diisocyanate, he

Description

United States Patent PROCESS FOR DYEING TEXTILE MATERIALQ Robert Kuth, Cologne-Snlz, Otto Schneider, Cologne-Flrttard, and Mathieu Quaedvlieg, Leverkusen, Germany, assignors to Farbenfabriken Bayer Aktiengesellschaft, Leverirusen, Germany, a German corporation No Drawing. Filed Mar. 10, 1964, Ser. No. 350,685 Claims riority, application Germany, Mar. 16, 1963,
4 Claims. (Cl. 8-42) The present invention relates to a process wherein textile materials are dyed in such a manner that the dyestufis are padded or printed in the form of solutions or suspensions and subsequently fixed by heating; reference may be made, for example, to the Thermosol process described in American Dyestuff Reporter, 1949, page 593. More particularly the present invention concerns a process wherein such a padding or printing of textile materials is carried out in the presence of water-soluble reaction products of aromatic, hydroaromatic or aliphatic monoor poly-isocyanates with high-molecular hydroxy-alkylation products of compounds which contain at least 8 carbon atoms and possess only one single hydrogen atom capable of reacting with alkylene oxides.
The reaction products to be used according to the invention contain at least once the grouping wherein R means an alkylene radical containing two to four carbon atoms, and X stands for the radical of a compound which contains at least 8 carbon atom and possesses only one single hydrogen atom capable of reacting with alkylene oxides, while n is a number between and 200.
Suitable reaction products can be obtained, for example, by reacting at about 5070 C. ethyl isocyanate, stearyl isocyanate, phenyl isocyanate, toluylene diisocyanate, hexamethylene diisocyanate, l,4-diisocyanato-cyclohexane, 4,4-diisocyanato-dicyclohexylmethane, 4,4'-diisocyanato-diphenylmethane, w,w' diisocyanato-dimethylbenzene or 4,4',4"-triisocyanato-triphenylmethane with hydroxy-alkylation products which are prepared by the addi. tion of alklene oxides, such as ethylene oxide or propylene oxide, in a molecular ratio of 20-200z1, on monohydric alcohols or carboxylic acids containing at least 8 carbon atoms, such as especially lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, hydroabietyl alcohol or lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, abietic acid and naphthenic acids, furthermore isohexyl phenol, heptyl phenol, nonyl phenol, dodecyl phenol or dodecyl mercaptan as well as secondary monoarnines, such as methyl stearyl amine.
The textile materials which are to be dyed or printed by the process according to the invention may be based on the most varied synthetic products, for example polyarnides, such as polycaprolactam, polyadipic acid, furamethylene diamide and polyamino-undecanic acid, furthermore polyurethanes or polyesters, such as those from terephthalic acid and ethylene glycol or 1,4-dimethylol cyclohexane, as well as especially polyacrylonitrile and copolymers of acrylonitrile with other vinyl compounds, for example acrylic acid esters, acrylic acid amides, vinylpyridine, vinyl chloride and vinylidene chloride. Furthermore, the process according to the present invention comprises the dyeing or printing of those textile materials which are produced from cellulose esters, for example from cellulose triacetate or butyrate. The process according to the present invention can also be applied to mixed fabrics of synthetic fibers or to mixed fabrics of synthetic fibers with fibers of native origin, such as wool or cotton, for example.
As in the aforesaid known dyeing process, the greatest variety of dyestuffs can also be employed in the present case, for example dispersion dyestuffs, vat dyestuffs, acid wool dyestuffs, metal complex dyestutfs or basic dyestuffs. Mixed fabrics can be dyed, with a suitable choice of dyestuffs, according to a single or multiple bath process possibly with insertion of an exhaust process, or selectively, if desired.
It is also possible by the process according to the invention to dye synthetic fiber materials in a satisfactory manner with dyestuffs with which they could hitherto be dyed only according to the exhaust process or not at all. Thus, for example, it is now possible to dye or print polyamide fibers with 2:1-metal-chromium complex dyestuffs, or polyacrylonitrile fibers with dispersion dyestuffs.
The reaction products to be used according to the invention are in general employed in amounts of 01-10%, preferably in amounts of 0.25.0%, referred to the dye liquor or printing paste, in the form of solutions or dispersions; they may, however, also be admixed in suitable concentrations to the dyestuffs. If the reaction products are not sufficiently soluble from the start, nonionic emulsifiers, such as hydroxy-alkylation products of fatty alcohols, fatty acids, naphthenic acids, of abietic acid or polyaryl-, alkylaryland alkylphenols, as well as ionic emulsifiers such as alkylaryl or alkyl sulphonates, can be used as dispersing agents.
The reaction products to be employed according to the present invention ensure an even distribution of the dyestuffs before and after fixation; they prevent two-sidedness and selvedge runnings of the dyeings and impart a pleasant handle to the textile materials; moreover they substantially increase the dyestufi yield, render a satisfactory dyeing possible even when several dyestuffs are used and enable the fixation temperature to be kept lower by 10- 20 C. or the duration of fixing correspondingly shorter than is customary with the Thermosol process mentioned in the beginning. In addition, the use of thickening agents otherwise necessary which may cause the machine aggregates to become sticky can be dispensed with.
If desired, other assistants may also be added to the dye liquors, e.g., softening agents, carriers, antistatic compounds and also hydrotopic agents for increasing the solubility of the dyestuffs.
As compared with the polyethers or amides which have already been proposed as auxiliary agents for the Thermosol process, for example in Belgian patent specifications Nos. 615,102 and 615,207, the reaction products to be used according to the present invention are distinguished by the fact that a still higher dyestulf yield can be achieved by their use.
The following examples serve to illustrate the invention without, however, limiting the scope thereof. The dye-' stufis designated by (a) to (i) are specified in the list given at the end of the description.
EXAMPLE 1 A fabric of polyacrylonitrile threads is impregnated on the foulard with a liquor which contains per litre 20 g. of the dyestuff (a) and 20 g. of the product obtained by reaction of 1 mol of 2,4-toluylene diisocyanate with 1 mol each of the hydroxy-alkylation products which were produced by the addition of mol of ethylene oxide on 1 mol of stearyl alcohol and by the addition of 170 mol of ethylene oxide on 1 mol of stearic acid. The fabric is then squeezed off to a weight increase of about 80% and dried at 80140 C. The fabric is subsequently treated in a tenter frame at ISO- C. for 45 seconds with hot air, then rinsed, washed and dried. The brilliant yellow dyeing 3 obtained on the fabric is distinguished by excellent levelness, a very high efiiciency of the dyestufi and outstanding fastness.
When a liquor is employed which contains, instead of g. of the polymethine dyestuff (a), 20 g. of the azo dyestufi (b) or 20 g. of the anthraquinone dyestuflf (c), a red dyeing or a blue dyeing of similar properties is obtained.
EXAMPLE 2 A fabric of polycaprolactam is dyed, as described in Example 1, with a liquor which contains per litre 50 g. of the acid dyestutf (d) and, 20 g. of the product obtained by the reaction of 1 mol of 1,4-diisocyanato-cyclohexane with 1 mol each of the hydroxy-alkylation products prepared by the addition of 130 mol of ethylene oxide on 1 mol of stearyl alcohol and by the addition of mol of ethylene oxide on 1 mol of abietic acid. With a high efficiency of the dyestuii a uniform blue dyeing is obtained.
EXAMPLE 3 Knitted material of polycaprolactam or nylon is dyed, as described in Example 1, with a liquor containing per litre g. of the chromium complex of the dyestuff (e) and 20 g. of the product which was obtained by reacting at C. 1 mol of 4,4-diisocyanato-dicyclohexyl methane with 1 mol each of the hydroxy-alkylation products produced by the addition of 130 mol of ethylene oxide on 1 mol of oleyl alcohol and by the addition of 130 mol of ethylene oxide on 1 mol of oleic acid. The red dyeing obtained is distinguished by excellent general fastness properties. Dyeings of similar properties in yellow and blue shades are obtained by employing, instead of the dyestuff (e), the chromium complexes of the dyestuffs (f) or (g).
EXAMPLE 4 A fabric of polycaprolactam fibers is treated, as described in Example 1, with 'a liquor which contains per litre 40 g. of the dispersion dyestufi (h) and 10g. of the product obtained by the reaction of 1 mol of 2,4-toluylene diisocyanate with 1 mol each of the hydroxy-alkylation products produced by the addition of 130 mol of ethylene oxide on 1 mol of nonylphenol and by the addition of mol of ethylene oxide on 1 mol of lauric acid. A brilliant blue dyeing with good fastness properties and good levelness is obtained.
EXAMPLE 5 A fabricg of polyethylene terephthalate fibers is dyed according to the instructions of Example 1 with a liquor which contains per litre 20 g. of the dyestuif (h) and 20 g. of one of the products obtained by the reaction of 1 mol of 2,4-toluylene diisocyanate with 1 or 2 mol of the hydroxy-alkylation product obtained by the addition of mol of ethylene oxide on 1 mol of oleyl alcohol. A uniform blue dyeing is obtained with a dyestuif efiiciency of more than 92% If, under otherwise equal conditions, the dispersion dyestuif (i) is employed instead of the dyestufi (h), then a red dyeing is obtained which is distinguished by a high levelncss and fastness to sublimation.
No. 666,081, Example 1.
(b) Quaternized dyestufi according to line 5 of the table of Example 6 of French patent specification No. 1,158,839.
benzeneN-bis-acetoxyethyl-aniline.
We claim:
1. In the process for the dyeing of textile materials of synthetic hydrophobic fibers, wherein the dyestuffs are padded or printed in the form of solutions or suspensions and subsequently fixed by dry heating, the improvement whereby the padding or printing is carried out in the presence of a water-soluble reaction product of aromatic hydrocarbon, hydroaromatic hydrocarbon or alkylene monoor polyisocyanates with high-molecular hydroxy- -=alkylation products of hydrocarbyl compounds which contain at least 8 carbon atoms and possess only one single hydrogen atom capable of reacting with alkylene oxides, the resulting reaction product containing the radicals of the formula wherein R is alkylene of 2-4 carbon atoms; X is an organic radical of the compounds which contain at least 8 carbon atoms; and n is an integer of 20-200.
2. The process of claim 1 wherein the dyeing step is effected with disperse dyes, acid dyes, basic dyes and metalized azo dyes on hydrophobic synthetic polymeric fibers by dry heating.
3. The process of claim 1 wherein about .110% by weight of water soluble reaction product is utilized in the dyeing process.
4. The process of claim 3 wherein the reaction product is the product obtained by reacting (a) a first component selected from the group consisting of alkyl isocyanate, phenyl isocyanate, toluylene diisocyanate, hexamethylene diisocyanate, 1,4-diisocyanate-cyclohexane, 4,4-diisocyanate-dicyclohexylmethane, 4,4'-diisocyanate diphenylmethane, w,w'-diisocyanate-dimethylbenzene and triisocyanate-triphenylmethane with (b) the reaction product of allrylene oxide with a monohydric alcohol, alkyl phenol, alkyl mercaptan or secondary monoamine effecting the reaction of (a) and (b) at a temperature of about 5070 C.
References Cited UNITED STATES PATENTS 2,085,706 6/1937 Schoeller et al. 25289 3,288,551 11/1966 Raflf 821 I. TRAVIS BROWN, Acting Primary Examiner.
DONALD LEVY, Assistant Examiner.

Claims (1)

1. IN THE PROCESS FOR THE DYEING OF TEXTILE MATERIALS OF SYNTHETIC HYDROPHOBIC FIBERS, WHEREIN THE DYESTUFFS ARE PADDED OR PINNED IN THE FORM OF SOLUTIONS OR SUSPENSIONS AND SUBSEQUENTLY FIXED BY DRY HEATING, THE IMPROVEMENT WHEREBY THE PADDING OR PRINTING IS CARRIED OUT IN THE PRESENCE OF A WATER-SOLUBLE REACTION PRODUCT OF AROMATIC HYDROCARBON, HYDROAROMATIC HYDROCARBON OR AROMATIC MONO- OR POLYISOCYANATES WITH HIGH-MOLECULAR HYDROXYALKYLATION PRODUCTS OF HYDROCARBYL COMPOUNDS WHICH CONTAIN AT LEAST 8 CARBON ATOMS AND POSSESS ONLY ONE SINGLE HYDROGEN ATOM CAPABLE OF REACTING WITH ALKYLENE OXIDES, THE RESULTING REACTION PRODUCT CONTAINING THE RADICALS OF THE FORMULA
US350685A 1963-03-16 1964-03-10 Process for dyeing textile materials Expired - Lifetime US3362780A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3462236A (en) * 1965-03-26 1969-08-19 Sandoz Ag Process for dyeing,padding or printing
US3477800A (en) * 1964-10-07 1969-11-11 Sandoz Ag Process for dyeing or printing of polyamide fibres
US4049378A (en) * 1974-02-18 1977-09-20 Bayer Aktiengesellschaft Dyestuff preparations
US4329146A (en) * 1971-11-09 1982-05-11 Ciba-Geigy Corporation Process for the dyeing of fibre material
US5594087A (en) * 1993-08-16 1997-01-14 Bayer Aktiengesellschaft Polyurethane thickeners and their use for thickening aqueous systems
US5936019A (en) * 1996-08-19 1999-08-10 Bayer Aktiengesellschaft Polyurethane-based thickener compositions and their use for thickening aqueous compositions
US6090876A (en) * 1996-10-29 2000-07-18 Borchers Gmbh Aqueous polyurethane thickener compositions having improved viscosity and rheological properties
US6177481B1 (en) 1996-06-12 2001-01-23 Bayer Aktiengesellschaft Defoamer mixtures, a process for the production thereof and the use thereof
US20020183442A1 (en) * 2001-03-12 2002-12-05 Christian Wamprecht New polyurethanes and their use for the thickening of aqueous systems
US6642302B2 (en) 2001-03-12 2003-11-04 Bayer Aktiengesellschaft Polyurethanes and their use for the thickening of aqueous systems
US6916876B2 (en) 2001-03-12 2005-07-12 Borchers Gmbh Powdered thickener preparations based on polyurethane and their use for thickening aqueous systems

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3630319A1 (en) * 1986-09-05 1988-03-10 Akzo Gmbh THICKENING AGENT
DE19503281A1 (en) 1995-02-02 1996-08-08 Bayer Ag Polyurethanes suitable as thickeners for aqueous systems

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2085706A (en) * 1930-11-29 1937-06-29 Ig Farbenindustrie Ag Derivatives of carboxylic acid amides
US3288551A (en) * 1963-08-08 1966-11-29 Ciba Geigy Corp Process for the coloring of fiber blends of polyester and native or regenerated cellulose

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2085706A (en) * 1930-11-29 1937-06-29 Ig Farbenindustrie Ag Derivatives of carboxylic acid amides
US3288551A (en) * 1963-08-08 1966-11-29 Ciba Geigy Corp Process for the coloring of fiber blends of polyester and native or regenerated cellulose

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3477800A (en) * 1964-10-07 1969-11-11 Sandoz Ag Process for dyeing or printing of polyamide fibres
US3462236A (en) * 1965-03-26 1969-08-19 Sandoz Ag Process for dyeing,padding or printing
US4329146A (en) * 1971-11-09 1982-05-11 Ciba-Geigy Corporation Process for the dyeing of fibre material
US4049378A (en) * 1974-02-18 1977-09-20 Bayer Aktiengesellschaft Dyestuff preparations
US5594087A (en) * 1993-08-16 1997-01-14 Bayer Aktiengesellschaft Polyurethane thickeners and their use for thickening aqueous systems
US6177481B1 (en) 1996-06-12 2001-01-23 Bayer Aktiengesellschaft Defoamer mixtures, a process for the production thereof and the use thereof
US5936019A (en) * 1996-08-19 1999-08-10 Bayer Aktiengesellschaft Polyurethane-based thickener compositions and their use for thickening aqueous compositions
US6090876A (en) * 1996-10-29 2000-07-18 Borchers Gmbh Aqueous polyurethane thickener compositions having improved viscosity and rheological properties
US20020183442A1 (en) * 2001-03-12 2002-12-05 Christian Wamprecht New polyurethanes and their use for the thickening of aqueous systems
US6642302B2 (en) 2001-03-12 2003-11-04 Bayer Aktiengesellschaft Polyurethanes and their use for the thickening of aqueous systems
US20040054117A1 (en) * 2001-03-12 2004-03-18 Christian Wamprecht New polyurethanes and their use for the thickening of aqueous systems
US6916876B2 (en) 2001-03-12 2005-07-12 Borchers Gmbh Powdered thickener preparations based on polyurethane and their use for thickening aqueous systems

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GB1016086A (en) 1966-01-05
DE1444243A1 (en) 1968-10-24
BE645233A (en) 1964-07-16

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