US3663157A - Disperse or monosulfonated acid dye printed nylon resisted with hydroxy diaryl sulfone-formaldehyde condensate - Google Patents

Disperse or monosulfonated acid dye printed nylon resisted with hydroxy diaryl sulfone-formaldehyde condensate Download PDF

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US3663157A
US3663157A US642304A US3663157DA US3663157A US 3663157 A US3663157 A US 3663157A US 642304 A US642304 A US 642304A US 3663157D A US3663157D A US 3663157DA US 3663157 A US3663157 A US 3663157A
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process according
fibers
water
dyestuffs
acid
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Heinz Gilgien
Gerhard Koegel
Melvin Harris
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BASF Schweiz AG
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Ciba AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/41—Phenol-aldehyde or phenol-ketone resins
    • D06M15/412—Phenol-aldehyde or phenol-ketone resins sulfonated
    • 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/12—Reserving parts of the material before dyeing or printing ; Locally decreasing dye affinity by chemical means
    • 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
    • Y10S8/924—Polyamide fiber

Definitions

  • Nitrogenous fibers suitable for printing by the present process are above all those of synthetic origin. Particularly good results are obtained on synthetic polyamides, such as condensation products from adipic acid and hexamethylenediamine, polycondensates of e-caprolactam or of w-aminoundecanoic acid.
  • the fibers may be in any desired stage of their processing, that is to say they may in the form of filaments, staple fibers, textured fibers, combings, fabrics or hosiery.
  • the dyestuffs must be soluble or at least dispersible in water. Particularly valuable are the water-soluble dyestuffs, for example substantive dyestuffs, I:l-metal complex dyestuffs, and especially metal-free acid wool dyes and 1:2- metal complex dyestuffs. As dyestuffs that are only dispersible in water there are suitable, above all, the so-called disperse dyestuffs, for example those of the type of the 1:2-metal complex dyestuffs.
  • disperse dyestuffs refers to those organic, coloured compounds of which at most traces are soluble in water so that they must be applied in the form of fine dispersions.
  • the printing pastes used for the application of the dyestuffs defined above contain the conventional additives, such, for example, as thickeners, hydrotropic agents, solution promoters and the like.
  • the dyestuffs are fixed by steaming.
  • Fiber-affinic resists for synthetic polyamide fibers are compounds that prevent the fibers being stained by the dyestuff, either during dyeing or during washing.
  • Such compounds are as a rule water-soluble, anionic and as such known. They should have no color of their own, or at least they should not change the color of the fibrous material under treatment.
  • a list of such compounds will be found in 'Vor opposition und Fa'rben von synthetician Fasern" by H.U. Schmidlin, 1958, but this list of course does not claim to be complete, and the present invention is not limited to the use of the compounds listed.
  • water-soluble anionic polycondensates of formaldehyde with diarylsulphones that contain at least one phenolic hydroxyl group.
  • aromatic components there are suitable dicyclic and especially monocyclic compounds containing at least one phenolic hydroxyl group.
  • other substitutents may be present, such as sulphonic acid groups, halogen atoms or alkyl radicals, especially alkyls containing one to four carbon atoms.
  • the sulphones are prepared from the phenolic compounds referred to above by known methods, for example by reaction with sulphuric acid at an elevated temperature. In this connection it is also possible to use mixtures of the aromatic components defined above.
  • sulphones are subjected to polycondensation with formaldehyde in known manner, for example in an acidic or alkaline medium at an elevated temperature.
  • formaldehyde in known manner, for example in an acidic or alkaline medium at an elevated temperature.
  • the sulphones are sulphonated either before the condensation or after it in the form of the polycondensates.
  • the fibrous material thus treated is then dried.
  • the pH values of the aqueous preparations may be in the acid, neutral or alkaline region, but preferably they are acid, in fact in the pH region from 3 to 5, or neutral.
  • the acid pH value is produced by adding inorganic, or preferably organic, acids of low molecular weight.
  • the amount of resist to be used varies within wide limits and is in the padding process 0.1 to 10 percent referred to the padding liquor, or 0.1 to 10 percent, preferably 0.5 to 3 percent, referred to the fibrous material when working by the exhaustion method.
  • the preparation may also contain optical brighteners, bleaches, for example reducing agents, or other usual additives.
  • the advantage of the present process is that owing to the pretreatment a smaller quantity of resist is needed than when the resist is added to the washing liquor. As a result of this addition the white ground of the fibers is not stained by unfixed dyestuff during the washing operation.
  • EXAMPLE 1 Textured hosiery from an adipic acidlhexamethylenediamine condensate is treated. The treatment takes 30 minutes. The liquor has a goods-to-liquor ratio of l 40, a temperature of 80 C., a pH value of 3.5 (adjusted with acetic acid) and contains 2 percent, referred to the weight of the fibers, of the polycondensate, described below, of a phenol/sulphuric acid reaction product with formaldehyde. The material is then rinsed for a short time and dried.
  • the goods thus pretreated are then printed with a printing paste consisting of 30 parts of the dyestufi c.l. Acid Orange 47 of the formula SO H 6-011.
  • the printed material is dried and steamed for 20 minutes in a conventional ager at 102 C., then rinsed in cold water,
  • a product having similar, good properties is obtained with a suspension of 200 g. of 4,4-dihydroxydiphenylsulphone in 100 g. of acetic anhydride is sulphonated with 100 g. of concentrated sulphuric acid, 300 ml. of water are added and 283 m1. of liquid are distilled off.
  • this reaction mixture is mixed with the reaction mixture obtained in the manufacture of ortho-cresol-4-sulphonic acid from 21.6 g. of ortho-cresol in 25 g. of acetic anhydride with 25 g. of concentrated sulphuric acid, and the two components are condensed with 80 g. of 30 percent aqueous formaldehyde solution, a product is obtained of which 80 mol percent consist of sulphone.
  • EXAMPLE 2 Textured hosiery from polyamide 6.6 is impregnated on a padder to a weight increase after squeezing of about 90 percent with a preparation containing in 1,000 parts of water 20 parts of the resist described below, and the material is then dried at 80 C.
  • the material thus pretreated and dried is then printed with a printing paste consisting of 30 parts of the 1:2-chromium complex of the dyestufi,
  • the residual reaction mixture is diluted with another 20 ml. of water, mixed with 20 g. of 30 percent aqueous formaldehyde solution and the whole is heated for 5 hours at to C., then allowed to cool, and 30 percent sodium hydroxide solution is added to the thickly 1i uid condensation product until a pH value of 7 has been reac ed.
  • the resulting product can be diluted with water in any desired proportion.
  • a product having similar properties is obtained when the reaction mixture is adjusted to a pH value from 8 to 8.5 by means of 30 percent sodium hydroxide solution before the formaldehyde is added.
  • a process for printing synthetic nitrogenous fibers with dyestuffs with no more than one sulfonate group, which dyestuffs are soluble or dispersible in water which comprises pretreating the fibers to be printed with an aqueous preparation consisting substantially of at least one fiber-substantive, water-soluble, anionic resist for synthetic polyamide fibers selected from the group consisting of polycondensates of diarysulfones containing at least one phenolic hydroxy group with formaldehyde, whereupon the fibers so treated are dried and then printed under textile printing conditions with the printing paste containing the dyestuff.
  • diarylsulfone is made from monocyclic hydroxyaryl compounds.
  • diarylsulfone is a dihydroxydiphenylsulfone.
  • polycondensates consist of dihydroxydiphenylsulfones and hydroxybenzene sulfonic acid the content of sulfone being at least 30 mol percent.

Abstract

A process for printing synthetic nitrogenous fibers with dyestuff that are soluble or dispersible in water is disclosed. The fibers to be printed are pretreated with an aqueous preparation consisting substantially of at least one fiber, substantive water-soluble, anionic resist for synthetic polyamide fibers selected from the group consisting of polycondensates of diarylsulfones containing at least one phenolic hydroxy group with formaldehyde. The fibers so pretreated are then dried and then printed with the printing paste containing the dyestuff.

Description

United States Patent Gilgien et al.
[ 1 May 16,1972
[54] DISPERSE OR MONOSULFONATED ACID DYE PRINTED NYLON RESISTED WITH HYDROXY DIARYL SULFONE- FORMALDEHYDE CONDENSATE [72] lnventors: Heinz Gilgien, Riehen; Gerhard Koegel, Reinach; Melvin Harris, Arlesheim, all of Switzerland [73] Assignee: Ciba Limited, Basel, Switzerland [22] Filed: May 31, 1967 [21] Appl. No.2 642,304
[30] Foreign Application Priority Data June 3, 1966 Switzerland ..8088/66 521 US. Cl
[51] Int. Cl. ..D06p 5/12 [58] Field otsearch ..8/15, 65, 73,21
[56] References Cited UNITED STATES PATENTS 2,623,806 12/1952 Fuchs ..8/21
3,352,624 ll/l967 Harding ..8/15
FOREIGN PATENTS OR APPLICATIONS 759,595 10/ 1956 Great Britain Primary Examiner-Donald Levy Attorney-Harry Goldsmith, Joseph G. Kolodny and Bryant W. Brennan [57] ABSTRACT 10 Claims, No Drawings DISPERSE OR MONOSULFONATED ACID DYE PRINTED NYLON RESISTED WITH HYDROXY DlARYL SULFONE- FORMALDEHYDE CONDENSATE The present invention provides a process for printing nitorgenous fibers with dyestuffs that are soluble or only dispersible in water. According to the present process the fibrous material is pre-treated with an aqueous preparation containing at least one fiber-substantine resist for synthetic polyamide fibers. The impregnated material is then dried and printed in the usual manner.
Nitrogenous fibers suitable for printing by the present process are above all those of synthetic origin. Particularly good results are obtained on synthetic polyamides, such as condensation products from adipic acid and hexamethylenediamine, polycondensates of e-caprolactam or of w-aminoundecanoic acid. The fibers may be in any desired stage of their processing, that is to say they may in the form of filaments, staple fibers, textured fibers, combings, fabrics or hosiery.
The dyestuffs must be soluble or at least dispersible in water. Particularly valuable are the water-soluble dyestuffs, for example substantive dyestuffs, I:l-metal complex dyestuffs, and especially metal-free acid wool dyes and 1:2- metal complex dyestuffs. As dyestuffs that are only dispersible in water there are suitable, above all, the so-called disperse dyestuffs, for example those of the type of the 1:2-metal complex dyestuffs. The term disperse dyestuffs refers to those organic, coloured compounds of which at most traces are soluble in water so that they must be applied in the form of fine dispersions.
The printing pastes used for the application of the dyestuffs defined above contain the conventional additives, such, for example, as thickeners, hydrotropic agents, solution promoters and the like. As a rule, the dyestuffs are fixed by steaming.
Fiber-affinic resists for synthetic polyamide fibers are compounds that prevent the fibers being stained by the dyestuff, either during dyeing or during washing. Such compounds are as a rule water-soluble, anionic and as such known. They should have no color of their own, or at least they should not change the color of the fibrous material under treatment. Thus, for example, a list of such compounds will be found in 'Vorbehandlung und Fa'rben von synthetischen Fasern" by H.U. Schmidlin, 1958, but this list of course does not claim to be complete, and the present invention is not limited to the use of the compounds listed.
Of special value are water-soluble anionic polycondensates of formaldehyde with diarylsulphones that contain at least one phenolic hydroxyl group. As aromatic components there are suitable dicyclic and especially monocyclic compounds containing at least one phenolic hydroxyl group. However, in addition to the hydroxyl group other substitutents may be present, such as sulphonic acid groups, halogen atoms or alkyl radicals, especially alkyls containing one to four carbon atoms. Particularly suitable are compounds of the type of the phenol, of the mono-alkylphenols or dialkylphenols, for example of the cresols or xylenols, of the monoor dihalogenophenols, for example of the chlorophenols or dichlorophenols, or resorcinol or of pyrocatechol.
The sulphones are prepared from the phenolic compounds referred to above by known methods, for example by reaction with sulphuric acid at an elevated temperature. In this connection it is also possible to use mixtures of the aromatic components defined above.
These sulphones are subjected to polycondensation with formaldehyde in known manner, for example in an acidic or alkaline medium at an elevated temperature. However, it is not necessary to perform the condensation exclusively with sulphones and it may be performed also with mixtures of sulphones and sulphonic acids of the phenolic compounds described above. If this is the case, the polycondensate should contain at least 30, preferably at least 40, mol percent of sulphone. When, on the other hand, exclusively sulphones are subjected to the polycondensation, the sulphones are sulphonated either before the condensation or after it in the form of the polycondensates. In this reaction it is possible to introduce sulphonic acid groups either before or after the condensation with formaldehyde. The polycondensates of sulphones, whose aromatic hydroxy compounds are phenol, cresols or xylenols, are specially preferred because of their accessibility and their potency.
These resists are applied during the pretreatment according to the padding or preferably the exhaustion method, using temperatures from 10 to 130 C., preferably from to l00 C. The fibrous material thus treated is then dried. The pH values of the aqueous preparations may be in the acid, neutral or alkaline region, but preferably they are acid, in fact in the pH region from 3 to 5, or neutral. The acid pH value is produced by adding inorganic, or preferably organic, acids of low molecular weight.
The amount of resist to be used varies within wide limits and is in the padding process 0.1 to 10 percent referred to the padding liquor, or 0.1 to 10 percent, preferably 0.5 to 3 percent, referred to the fibrous material when working by the exhaustion method.
Apart from the resist the preparation may also contain optical brighteners, bleaches, for example reducing agents, or other usual additives.
The advantage of the present process is that owing to the pretreatment a smaller quantity of resist is needed than when the resist is added to the washing liquor. As a result of this addition the white ground of the fibers is not stained by unfixed dyestuff during the washing operation.
Parts in the following Examples are by weight.
EXAMPLE 1 Textured hosiery from an adipic acidlhexamethylenediamine condensate is treated. The treatment takes 30 minutes. The liquor has a goods-to-liquor ratio of l 40, a temperature of 80 C., a pH value of 3.5 (adjusted with acetic acid) and contains 2 percent, referred to the weight of the fibers, of the polycondensate, described below, of a phenol/sulphuric acid reaction product with formaldehyde. The material is then rinsed for a short time and dried.
The goods thus pretreated are then printed with a printing paste consisting of 30 parts of the dyestufi c.l. Acid Orange 47 of the formula SO H 6-011.
O 3 H 5( J z I 50 parts of thiourea 50 parts of thiodiethyleneglycol 5 l 0 parts of water 300 parts of a 12 percent aqueous solution of a commercial,
modified locust bean gum 60 parts of ammonium tartrate solution of 15 Be.
The printed material is dried and steamed for 20 minutes in a conventional ager at 102 C., then rinsed in cold water,
washed in a bath heated at 50 C., containing in 1,000 parts of water 2 parts of any desired synthetic detergent, and once more rinsed for a short time in cold water. A brilliant orange print is obtained. The unprinted areas remain white, whereas when a print that has not been pretreated is washed, the white areas display a distinct, undesirable coloration.
PREPARATION OF THE RESIST 50 Grams of concentrated sulphuric acid are stirred dropwise at room temperature into a suspension of g. of 4,4- dihydroxydiphenylsulphone in 50 g. of acetic anhydride. The temperature is then raised to about 100 C., and after 6 hours 300 ml. of water are added portionwise, while at the same time 311 ml. of liquid are distilled off under reduced pressure. The residual reaction mixture is mixed with a reaction mixture obtained in the manufacture of ortho-cresol-4-sulphonic acid from 64.9 g. of ortho-cresol in 75 g. of acetic anhydride with 75 g. of concentrated sulphuric acid. Then 80 g. of 30 percent aqueous formaldehyde solution are added to the mixture of these two reaction mixtures. The whole is heated for 5 hours at 100 to 105 C. and then allowed to cool. The thickly liquid condensation product, 40 mol percent of which consist of 4,4-dihydroxydiphenylsulphone-3 -sulphonic acid and 60 mol percent of ortho-cresol-4-sulphonic acid, is then treated with 30 percent sodium hydroxide solution until a pH value of 7 has been reached. The resulting product can be diluted with water in any desired proportion.
A product having similar, good properties is obtained with a suspension of 200 g. of 4,4-dihydroxydiphenylsulphone in 100 g. of acetic anhydride is sulphonated with 100 g. of concentrated sulphuric acid, 300 ml. of water are added and 283 m1. of liquid are distilled off. When this reaction mixture is mixed with the reaction mixture obtained in the manufacture of ortho-cresol-4-sulphonic acid from 21.6 g. of ortho-cresol in 25 g. of acetic anhydride with 25 g. of concentrated sulphuric acid, and the two components are condensed with 80 g. of 30 percent aqueous formaldehyde solution, a product is obtained of which 80 mol percent consist of sulphone.
EXAMPLE 2 Textured hosiery from polyamide 6.6 is impregnated on a padder to a weight increase after squeezing of about 90 percent with a preparation containing in 1,000 parts of water 20 parts of the resist described below, and the material is then dried at 80 C.
The material thus pretreated and dried is then printed with a printing paste consisting of 30 parts of the 1:2-chromium complex of the dyestufi,
prepared according to U. S. Pat. No. 2,565,895, and of the formula 50 parts of thiourea 50 parts of thiodiethyleneglycol 510 parts of water MANUFACTURE OF THE RESIST Thirty-five grams of concentrated sulphuric acid are stirred at room temperature dropwise into a suspension of 70 g. of 4.4-dihydroxydiphenylsulphone in 35 g. of acetic anhydride. The temperature is then raised to 98 to 100 C. and maintained at this value for 6 hours. 75 ml of water are then added portion wise under a pressure of 30 to 50 mm. Hg, and at the same time 88 ml. of liquid are distilled out of the reaction mixture. The residual reaction mixture is diluted with another 20 ml. of water, mixed with 20 g. of 30 percent aqueous formaldehyde solution and the whole is heated for 5 hours at to C., then allowed to cool, and 30 percent sodium hydroxide solution is added to the thickly 1i uid condensation product until a pH value of 7 has been reac ed. The resulting product can be diluted with water in any desired proportion.
A product having similar properties is obtained when the reaction mixture is adjusted to a pH value from 8 to 8.5 by means of 30 percent sodium hydroxide solution before the formaldehyde is added.
EXAMPLE 3 formula II 0 011 1 1 CN or. 18760 plnk 0r HO;S- N=N-C f 30 parts of the 1:2-chromium complex of the dyestuff of the formula 0 H H 0 G1 I I 1 Cl. Acid Blue HzNS O 2 We claim:
1. A process for printing synthetic nitrogenous fibers with dyestuffs with no more than one sulfonate group, which dyestuffs are soluble or dispersible in water which comprises pretreating the fibers to be printed with an aqueous preparation consisting substantially of at least one fiber-substantive, water-soluble, anionic resist for synthetic polyamide fibers selected from the group consisting of polycondensates of diarysulfones containing at least one phenolic hydroxy group with formaldehyde, whereupon the fibers so treated are dried and then printed under textile printing conditions with the printing paste containing the dyestuff.
2. A process according to claim 1, wherein synthetic polyamide fibers are printed.
3. A process according to claim 1, wherein the fibers are pretreated by the exhaustion method in an acid bath having a temperature of 80 to 100 C.
4. A process according to claim 3, wherein the pH-value is from 3 to 5.
5. Process according to claim 1, wherein the diarylsulfone is made from monocyclic hydroxyaryl compounds.
6. Process according to claim 5, wherein the diarylsulfone is a dihydroxydiphenylsulfone.
7. Process according to claim 1, wherein the polycondensates consist of dihydroxydiphenylsulfones and hydroxybenzene sulfonic acid the content of sulfone being at least 30 mol percent.
8. Process according to claim 1, wherein the polycondensates consist of sulfonic acids of dihydroxydiphenylsulfones.
9. Process according to claim 1, wherein the dyestuffs are acid, metal-free wool dyes.
10. Process according to claim 1, wherein the dyestuffs are water-soluble 1:2-metal complex dyestuffs.
g g g UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3 3 57 Dated May- 16, 1972 Inventor s HEINZ GILGIEN ET AL It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
Cover page, under "[73] after "Assigneez" delete "CIBA LIMITED" and substitute CIBA- GEIGY AG Signed and sealed this 2nd day of. April 19m.
(SEAL) Attest:
EDWARD M.FLETCHER,JR. C. MARSHALL DANN Attesting Officer Commissioner of Patents

Claims (9)

  1. 2. A process according to claim 1, wherein synthetic polyamide fibers are printed.
  2. 3. A process according to claim 1, wherein the fibers are pretreated by the exhaustion method in an acid bath having a temperature of 80* to 100* C.
  3. 4. A process according to claim 3, wherein the pH-value is from 3 to 5.
  4. 5. Process according to claim 1, wherein the diarylsulfone is made from monocyclic hydroxyaryl compounds.
  5. 6. Process according to claim 5, wherein the diarylsulfone is a dihydroxydiphenylsulfone.
  6. 7. Process according to claim 1, wherein the polycondensates consist of dihydroxydiphenylsulfones and hydroxybenzene sulfonic acid the content of sulfone being at least 30 mol percent.
  7. 8. Process according to claim 1, wherein the polycondensates consist of sulfonic acids of dihydroxydiphenylsulfones.
  8. 9. Process according to claim 1, wherein the dyestuffs are acid, metal-free wool dyes.
  9. 10. Process according to claim 1, wherein the dyestuffs are water-soluble 1:2-metal complex dyestuffs.
US642304A 1966-06-03 1967-05-31 Disperse or monosulfonated acid dye printed nylon resisted with hydroxy diaryl sulfone-formaldehyde condensate Expired - Lifetime US3663157A (en)

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CH808866A CH464141A (en) 1966-06-03 1966-06-03 Process for printing textile material made of synthetic polyamide fibers

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CH (1) CH464141A (en)
DE (1) DE1619667B2 (en)
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SE (1) SE335712B (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3765839A (en) * 1970-09-03 1973-10-16 Ciba Geigy Ag Process for improving the wet fastness properties of dyeings on polyamide fibre material
US3790344A (en) * 1969-12-03 1974-02-05 Bayer Ag Agents for improving the fastness to wet processing
US3999940A (en) * 1975-01-02 1976-12-28 Congoleum Corporation Multicolored pile materials and processes for making the same
US4215988A (en) * 1977-10-20 1980-08-05 Meisei Chemical Works, Ltd. Resist printing method
US4411666A (en) * 1980-04-25 1983-10-25 Sumitomo Chemical Company, Limited Process for dyeing polyolefin fiber materials
US4592940A (en) * 1983-12-16 1986-06-03 Monsanto Company Stain-resistant nylon carpets impregnated with condensation product of formaldehyde with mixture of diphenolsulfone and phenolsulfonic acid
US4619853A (en) * 1983-12-21 1986-10-28 Monsanto Company Easy-clean carpets which are stain resistant and water impervious
US4680212A (en) * 1986-03-06 1987-07-14 Monsanto Company Stain resistant nylon fibers
US4780099A (en) * 1986-08-26 1988-10-25 E. I. Du Pont De Nemours And Company Method for producing stain resistant polyamide fibers
US4800118A (en) * 1987-11-04 1989-01-24 West Point Pepperell Compositions and methods for imparting stain resistance to textile articles
US4839212A (en) * 1986-03-06 1989-06-13 Monsanto Company Stain resistant nylon carpets
US4879180A (en) * 1986-03-06 1989-11-07 Monsanto Company Stain-resistant nylon fibers
US5131918A (en) * 1990-12-13 1992-07-21 Hoechst Celanese Corporation Process for dyeing mixed anionic/cationic polyamide substrates with a specific type of vinyl sulfone dye
US5131914A (en) * 1990-12-13 1992-07-21 Hoechst Celanese Corporation Process for preparing multi-colored dyed polyamide substrates including the application of a reactive vinyl sulfone dye and a resist agent
US5182154A (en) * 1983-12-16 1993-01-26 Monsanto Company Stain resistant nylon carpets

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0242495B1 (en) * 1983-12-16 1990-07-25 Monsanto Company Stain-resistant nylon carpets
US4865885A (en) * 1987-06-19 1989-09-12 Crompton & Knowles Corporation Food color stain blocking fiber agents
DE4014977A1 (en) * 1990-05-10 1991-11-14 Basf Ag CONDENSATION PRODUCTS OF PHENOLMONOSULPHONIC ACIDS, DIHYDROXYDIPHENYL SULPHONES, UREA AND FORMALDEHYDE

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US2623806A (en) * 1952-12-30 Reserved polyamide fibers and a
GB759595A (en) * 1952-12-22 1956-10-24 Bradford Dyers Ass Ltd Textile and film ornamentation
US3352624A (en) * 1967-11-14 Swf ci

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2623806A (en) * 1952-12-30 Reserved polyamide fibers and a
US3352624A (en) * 1967-11-14 Swf ci
GB759595A (en) * 1952-12-22 1956-10-24 Bradford Dyers Ass Ltd Textile and film ornamentation

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3790344A (en) * 1969-12-03 1974-02-05 Bayer Ag Agents for improving the fastness to wet processing
US3765839A (en) * 1970-09-03 1973-10-16 Ciba Geigy Ag Process for improving the wet fastness properties of dyeings on polyamide fibre material
US3999940A (en) * 1975-01-02 1976-12-28 Congoleum Corporation Multicolored pile materials and processes for making the same
US4215988A (en) * 1977-10-20 1980-08-05 Meisei Chemical Works, Ltd. Resist printing method
US4411666A (en) * 1980-04-25 1983-10-25 Sumitomo Chemical Company, Limited Process for dyeing polyolefin fiber materials
US4592940A (en) * 1983-12-16 1986-06-03 Monsanto Company Stain-resistant nylon carpets impregnated with condensation product of formaldehyde with mixture of diphenolsulfone and phenolsulfonic acid
US5182154A (en) * 1983-12-16 1993-01-26 Monsanto Company Stain resistant nylon carpets
US4619853A (en) * 1983-12-21 1986-10-28 Monsanto Company Easy-clean carpets which are stain resistant and water impervious
USRE33365E (en) * 1986-03-06 1990-10-02 Monsanto Company Stain resistant nylon fibers
US4839212A (en) * 1986-03-06 1989-06-13 Monsanto Company Stain resistant nylon carpets
US4879180A (en) * 1986-03-06 1989-11-07 Monsanto Company Stain-resistant nylon fibers
US4680212A (en) * 1986-03-06 1987-07-14 Monsanto Company Stain resistant nylon fibers
US4780099A (en) * 1986-08-26 1988-10-25 E. I. Du Pont De Nemours And Company Method for producing stain resistant polyamide fibers
US4800118A (en) * 1987-11-04 1989-01-24 West Point Pepperell Compositions and methods for imparting stain resistance to textile articles
US5131918A (en) * 1990-12-13 1992-07-21 Hoechst Celanese Corporation Process for dyeing mixed anionic/cationic polyamide substrates with a specific type of vinyl sulfone dye
US5131914A (en) * 1990-12-13 1992-07-21 Hoechst Celanese Corporation Process for preparing multi-colored dyed polyamide substrates including the application of a reactive vinyl sulfone dye and a resist agent

Also Published As

Publication number Publication date
CH464141A (en) 1968-07-15
DE1619667A1 (en) 1971-03-25
GB1137785A (en) 1968-12-27
NL6707730A (en) 1967-12-04
DE1619667B2 (en) 1976-11-11
SE335712B (en) 1971-06-07

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