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 PDFInfo
- 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
Links
Classifications
-
- 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.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Paper (AREA)
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)
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)
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)
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 |
-
1966
- 1966-06-03 CH CH808866A patent/CH464141A/de unknown
-
1967
- 1967-05-26 DE DE1967C0042435 patent/DE1619667B2/de active Granted
- 1967-05-31 US US642304A patent/US3663157A/en not_active Expired - Lifetime
- 1967-06-01 GB GB25406/67A patent/GB1137785A/en not_active Expired
- 1967-06-02 SE SE07738/67A patent/SE335712B/xx unknown
- 1967-06-02 NL NL6707730A patent/NL6707730A/xx unknown
Patent Citations (3)
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)
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 |
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