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

Info

Publication number
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
Authority
US
United States
Prior art keywords
process according
fibers
water
dyestuffs
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US642304A
Other languages
English (en)
Inventor
Heinz Gilgien
Gerhard Koegel
Melvin Harris
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba AG filed Critical Ciba AG
Application granted granted Critical
Publication of US3663157A publication Critical patent/US3663157A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/41Phenol-aldehyde or phenol-ketone resins
    • D06M15/412Phenol-aldehyde or phenol-ketone resins sulfonated
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/12Reserving parts of the material before dyeing or printing ; Locally decreasing dye affinity by chemical means
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/924Polyamide 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.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Paper (AREA)
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)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH808866A CH464141A (de) 1966-06-03 1966-06-03 Verfahren zum Bedrucken von Textilmaterial aus synthetischen Polyamidfasern

Publications (1)

Publication Number Publication Date
US3663157A true US3663157A (en) 1972-05-16

Family

ID=4334970

Family Applications (1)

Application Number Title Priority Date Filing Date
US642304A Expired - Lifetime US3663157A (en) 1966-06-03 1967-05-31 Disperse or monosulfonated acid dye printed nylon resisted with hydroxy diaryl sulfone-formaldehyde condensate

Country Status (6)

Country Link
US (1) US3663157A (de)
CH (1) CH464141A (de)
DE (1) DE1619667B2 (de)
GB (1) GB1137785A (de)
NL (1) NL6707730A (de)
SE (1) SE335712B (de)

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 (de) * 1983-12-16 1990-07-25 Monsanto Company Fleckenabweisende Nylonteppiche
US4865885A (en) * 1987-06-19 1989-09-12 Crompton & Knowles Corporation Food color stain blocking fiber agents
DE4014977A1 (de) * 1990-05-10 1991-11-14 Basf Ag Kondensationsprodukte aus phenolmonosulfonsaeuren, dihydroxydiphenylsulfonen, harnstoff und formaldehyd

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

Similar Documents

Publication Publication Date Title
US3663157A (en) Disperse or monosulfonated acid dye printed nylon resisted with hydroxy diaryl sulfone-formaldehyde condensate
EP0118983B1 (de) Textilbehandlung
US4455147A (en) Transfer printing
US3669611A (en) Production of ornamental multitone effect on polyamide textile materials
US3765839A (en) Process for improving the wet fastness properties of dyeings on polyamide fibre material
US3288551A (en) Process for the coloring of fiber blends of polyester and native or regenerated cellulose
US2726133A (en) Effect threads
EP1592837B1 (de) Nicht vergilbende aldehydkondensationsprodukte
US3824076A (en) Liquid ammonia-caustic dye solution and dyeing therewith
US2999731A (en) Dyeing of normal wool
US3352624A (en) Swf ci
US5417724A (en) Method of treating acid dyed nylon fibers to enhance colorfastness
CA1053411A (en) Process for printing or pad-dyeing cellulose/polyester mixed fabrics
US4289496A (en) Finishing process
US3841831A (en) Process for dyeing polyester fiber
US4622045A (en) Method of dyeing wool with acid dyestuffs
US3989453A (en) Multicoloring polyester textile materials with acid dyes
US3199942A (en) Divinyl sulfone, diisocyanate, dicarboxylic acid or dihydroxysulfide reaction products with polyethylene ethers in high temperature pad dyeing and printing
US3802837A (en) Polyamide dyeing with a reaction product of a reactive dye-n-alkylamine alkyl carboxylic or sulfonic acid or salt thereof
US4661116A (en) Continuous dyeing of cationic dyeable polyester fibers
AU609460B2 (en) Dyeing and printing fibres
US5342417A (en) Method of treating cationic dyeable nylon fibers to inhibit cold water bleed
US3894842A (en) Process for preparing dyeings and prints fast to light on synthetic fibers
US5174791A (en) Process for dyeing and printing blend fabrics of polyester and natural fibre materials with disperse dye and polyether-polyester to inhibit soilins with disperse dye
US2743190A (en) Method for producing effects on fabrics