US3765839A - Process for improving the wet fastness properties of dyeings on polyamide fibre material - Google Patents

Process for improving the wet fastness properties of dyeings on polyamide fibre material Download PDF

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Publication number
US3765839A
US3765839A US00174534A US3765839DA US3765839A US 3765839 A US3765839 A US 3765839A US 00174534 A US00174534 A US 00174534A US 3765839D A US3765839D A US 3765839DA US 3765839 A US3765839 A US 3765839A
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process according
fixing agent
percent
water
formaldehyde
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V Mueller
H Berendt
M Harris
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Novartis AG
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Ciba Geigy AG
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928—Solvents other than hydrocarbons
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/56—Condensation products or precondensation products prepared with aldehydes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/922—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
    • 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
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • 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
    • Y10S8/903—Triple mixture of anionic, cationic, and nonionic emulsifiers for dyeing

Definitions

  • ABSTRACT A process for improving the wet fastness properties of dyeings on synthetic polyamide fiber material is provided.
  • the process is characterized in that preparations are applied to the fiber material at temperatures of 20 to 120C, which contain a water-soluble 'fixing agent with affinity for the fiber, an organic solvent or solvent mixture and at most 10 percent of water, relative to the preparation, and also, optionally an organosoluble dispersing agent.
  • the fiber material thus treated shows very good fastness properties and no deterioration of handle.
  • the present invention therefore relates to a process for improving the wet fastness properties of dyeings on synthetic polyamide fibre material.
  • the process is characterised in that preparations are applied to the fibre material, at temperatures of 20 to 120C, which contain a water-soluble fixing agent with affinity for the fibre, an organic solvent or solvent mixture and at most l percent of water, relative to the preparation, and also, optionally, an organo-soluble dispersing agent.
  • Suitable solvents for the process according to the in vention are, for example, solvents which are immiscibleor of only restricted miscibility with water, such as the petrol hydrocarbons, for example petroleum ether, benzene and halogenated benzenes or benzenes substituted with low molecular alkyl groups, such as, for example, toluene, xylene, ethylbenzene, cumene, monochlorobenzene and dichlorobenzene; alicycliccompounds, such as, for example, tetralin and cyclohexane,
  • ether and diethylene glycol monomethyl ether or monoethyl ether and also pyridine, acetonitrile, diacetone-alcohol, ethylene carbonate, 'y-butyrolactone, N,N-dimethylformamide, N,N-dimethylacetamide, N- methylpyrrolidone, tetramethylurea, tetramethylenesulphone, dimethylsulphoxide and others. Mixtures of the solvents mentioned can also be used.
  • the fixing agents possessing fibre affinity which are applied, in order to improve the wet fastness properties, to the fibre material after the actual dyeing process, but can also be present in the dyebath and are then absorbed simultaneously with the dyestuff onto the substrate, are as a rule anionic water-soluble compounds. They should not possess an intrinsic colour and should at least not change the intrinsic colour of the fibre material which is to be treated.
  • Particularly suitable fixing agents are the watersoluble anionic polycondensation products of diarylsulphones possessing at least one phenolic hydroxyl group with formaldehyde.
  • Possible aromatic components are bicyclic, but above all mono-cyclic, compounds which possess at least one phenolic hydroxyl group.
  • halogenated hydrocarbons such as, for example, the solvents trichloroethylene and perchloroethylene which are used in the drycleaning industry, and also chloroform, methylene chloride, carbon tetrachloride, dibromoethylene and the chlorinated ethanes, such as l,l-dichloroethane, l,2-dichloroethane, l,l,l-trichloroethane and l,l,2,2- tetrachloroethane.
  • halogenated hydrocarbons such as, for example, the solvents trichloroethylene and perchloroethylene which are used in the drycleaning industry, and also chloroform, methylene chloride, carbon tetrachloride, dibromoethylene and the chlorinated ethanes, such as l,l-dichloroethane, l,2-dichloroethane, l,l,l-trichloroethane and
  • a further group consists of the solvents which are miscible with water, such as, for example, the aliphatic alcohols methanol, ethanol or the propanols; ketones, such as acetone, methyl ethyl ketone and cyclohexanone; ethers and acetals, such as diisopropyl ether, diphenylene oxide, dioxane and tetrahydrofurane; glycol derivatives, such as ethylene glycol monomethyl ether, monoethyl ether and monobutyl tion to the hydroxyl group, however, other substituents can also be present, such as sulphonic acid groups, halogen atoms or alkyl radicals, especially alkyl radicals with one to four carbon atoms.
  • the solvents which are miscible with water such as, for example, the aliphatic alcohols methanol, ethanol or the propanols; ketones, such as acetone, methyl ethyl
  • the compounds of the type of phenol, the monoalkylphenols or dialkylphenols, for example the cresols or xylenols, the monohalogenophenols or dihalogenophenols, for example the chlorophenols or dichlorophenols, resorcinol or pyrocatechol, may be mentioned.
  • the sulphones are manufactured from the phenolic compounds described above in accordance with methods which are in themselves known, for example by reaction with sulphuric acid at elevated temperature.
  • sulphones are subjected to polycondensation with formaldehyde, following methods which are in themselves known, for example in an acid or alkaline medium at elevated temperature.
  • the condensation need, however, not be carried out exclusively with sulphones but can also take place with mixtures of sulphones and sulphonic acids of the phenolic compounds described. If such is the case, the polycondensation product should contain at least 30, and preferably 40, mol per cent of sulphone. If, on the other hand, exclusively sulphones are subjected to poly-condensation, either the sulphones are sulphonated before the condensation, or the polycondensates are sulphonated.
  • Suitable representatives of such surface-active compounds belong to the following types of compounds:
  • Ethers of polyhydroxy compounds such as polyoxyalkylated fatty alcohols, polyoxallrylated polyols, polyoxalkylated mercaptans and aliphatic amines, polyalkylated allcylphenols and alkylnaphthols, polyoxalkylated allrylarylmercaptans and alkylarylamines; and also the corresponding esters of these compounds with polybasic acids, such as sulphuric acid or phosphoric acid, optionally also in the form of ammonium salts or amine salts.
  • polyhydroxy compounds such as polyoxyalkylated fatty alcohols, polyoxallrylated polyols, polyoxalkylated mercaptans and aliphatic amines, polyalkylated allcylphenols and alkylnaphthols, polyoxalkylated allrylarylmercaptans and alkylarylamines; and also the corresponding esters of these compounds with poly
  • N-Hydroxyalkyl-carbonamides polyoxalkylated carbonamides and sulphonamides.
  • the monoethanol-amine salt of the phosphoric acid ester of the addition product of oleyl alcohol and six mols of ethylene oxide may, for example, be mentioned: the monoethanol-amine salt of the phosphoric acid ester of the addition product of oleyl alcohol and six mols of ethylene oxide; the ammonium salt of the acid sulphuric acid ester of the addition product of 17 mols of ethylene oxide to oleyl alcohol; the addition product of four mols of ethylene oxide to nonylphenol; the addition product of eight mols of ethylene oxide to one mol of p-tert.-octylphenol; the addition product of 9 mols of ethylene oxide to nonylphenol; the addition product of 8 mols of ethylene oxide to cetyl alcohol or oleyl a1- cohol; the addition product of coconut fatty acid and 2 mols of diethanolamine; the addition product of or 6 mols of ethylene oxide to castor oil, the addition product of mols of ethylene oxide
  • the simultaneous application of the fixing agents with the dyestuff takes place from organic solvent liquors by the exhaustion process.
  • the improvement in the wet fastness properties in this case relates only to dyeings from organic solvents.
  • the dyeings can have been produced either in liquors of organic solvents or in aqueous baths.
  • the after-treatment can be carried out in the exhausted dyeing liquor or in a new liquor.
  • aqueous liquors it is advisable to effect an intermediate drying of the fibres.
  • the finishing with the fixing agent is always carried out from an organic solvent.
  • the temperature ranges for the application are between 20 and 120C, preferably between 40 and C.
  • the treatment times are approximately between one and 30 minutes, preferably between five and 15 minutes, in the case of the after-treatment, whilst this time corresponds to the dyeing time if the fixing agent is applied from the dyebath.
  • the pl-l values of the preparations can lie in the acid, neutral or alkaline range and approximately encompass a range of pH 4 to 9, preferably of pl-l 5 to 8.
  • the pH value is adjusted by, for example, low molecular organic acids, such as formic acid, acetic acid or monochloroacetic acid, or ammonia.
  • the amounts in which the fixing agent is used vary within wide limits and are 0.1 to 10 percent, relative to the impregnating liquor, in the case of the padding process, or 0.1 to 10 percent, preferably 0.5 to 5 percent, relative to the fibre material, if the exhaustion process is used.
  • the particular amount of dispersing agent required varies correspondingly, and preferably both components are proportional to one another, that is to say the amount of dispersing agent also increases with increasing amount of fixing agent.
  • the ratio of fixing agent to dispersing agent is appropriately between 1:100 and 1:2. Suitable liquor ratios are between 1:5 and 1:100, preferably between 1:20 and 1:50.
  • Fibre materials which are suitable according to the invention are mainly synthetic polyamide fibres, such as nylon .6, nylon 6,6, nylon 6,10 (from hexamethylenediamine and sebacic acid), nylon 11 or nylon 6,6/6 (copolymers of hexarnethylenediamine, adipic acid and s-caprolactam), and also mixed fabrics containing synthetic polyamide fibres.
  • the fibre material can be in any desired states of processing.
  • the fibre material is dyed in a homogeneous solubilised preparation or dispersion of the dyestuff in an organic solvent or solvent mixture.
  • dispersion dyestuffs, reactive dyestuffs and metal complex dyestuffs which are suitable for dyeing the synthetic polyarnide fibres belong, for example, to the known classes of the monoazo and disazo dyestuffs as well as of the anthraquinone, methine, azomethine, azostyryl and formazane dyestuffs.
  • These dyestuffs which are water-soluble or only dispersible in water, can be used individually or as mixtures. If desired, other suitable types of dyestuffs can also be used.
  • the polyamide fibre material is thus appropriately dyed according to the known exhaustion process.
  • the dye-stuffs can, for example, appropriately be prepared as follows: working the dyestufi into a paste with the dispersing agent, diluting with the desired amount of an organic solvent, and mixing this preparation with a preparation of the fixing agent which has been diluted with water or with an organic solvent. A different sequence is also possible.
  • the fibre substrates treated according to the invention show good to very good fastness properties and no deterioration of handle as compared to untreated material.
  • a id action mixture is diluted with a further 20 ml of wa- Blue 72 are added, the dyebath is heated to the boil ter, treated with g of 30 percent strength aqueover the course of 30 minutes, dyeing is carried out for 0H5 formaldehyde Solution and heated five one hour at this temperature, and the dyeing is then fmou to 05C It iS en allo ed o Cool ished by rinsing and drying. A violet dyeing is obtained.
  • 50 g of the nylon mixture is adjusted to 3 P value of 8 to with Helanca tricot dyed as above are treated in this liquor percent strength sodium hydroxide solution. for five or 15 minutes at 50 or 70C with or without the 7- A mixture of 3 g o 4,4-dihydroxy-3-methyladdition of acid (monochloroacetic acid, up to a pH diphenylsulphone and 150.5 g of l-hydroxy-Z- value of about 4).
  • methylbenzene-4-sulphonic acid in 100 ml of water Fixing Agents is rendered alkaline with 463 g of 30 percent 1.
  • Manufacture of the fixing agent g of concen- 30 strength aqueous sodium hydroxide solution.
  • the finished fabric is treated at 60C viscous condensation product until a pH value of 7 with a solution containing 2 g of Sodium Car is reached.
  • the resulting product can be diluted hy r )ll and 5 g of soap/l 30 minutes, liquor ratio with water as desired. 1:50.
  • Condensation product of a sulphone mixture (4,4'- SNV 195,819: The finished fabric is wetted in water dihydroxy-dipheny1su1phone and 4,2 -dihydroxybetween 2 undyed fabrics. After pouring off the excess diphenylsulphone), phenolsulphonic acid and water, the test specimen is subjected to a certain load formaldehyde. in a suitable apparatus. Time; four hours,temperature 3. Condensation product of a sulphone mixture (4,4'- 37C.
  • test specimen is then separated from the surdihydroxy-diphenylsulphone and 4,2 '-dihydroxyface-dyed accompanying fabric and the fabrics are sepdiphenylsulphone), sulphuric acid and formaldearately dried.
  • the colour change and the bleeding are hyde. assessed.
  • Table 11 contains i 2 2:: g g the values of the wet fastness properties of the dyeing 5 1:; g achieved by the treatment with the fixing agent.
  • EXAMPLE 5 40 g of nylon-6,6 woven tricot are dyed, using a 1iquor ratio of 1:25, in a perchloroethylene liquor which contains 1.32 g of a dyestuff of the formula 1 l I SOaI-I The system is heated from 30C to 165 C over the course of 30 minutes and is kept at this temperature for 1 g of the fixing agent 2 are mixed with 25 ml of water. 1.65 g of the dyestuff of the forrnula NH: NH;
  • the depth of colour obtained corresponds to that obtained in a comparison dyeing without fixing agent, but otherwise under the same conditions.
  • EXAMPLE 6 g of nylon 6,6 woven tricot are dyed for one hour at 100C, using a liquor ratio of 1:50, in a perchloroethylene liquor which contains 0.66 g of the dyestuff of the formula orange HNCOCHCH2 Br Br thereafter the solvent is centrifuged off and the fabric is dried with warm air.
  • the amount of fixing agent applied to the fibre material is 5 percent at a liquor ratio of 1:50. A good improvement in the wet fastness properties of the fibre material dyed and finished in this way is achieved.
  • EXAMPLE 7 a A nylon-6,6 Helanca tricot is dyed in a perchloroethylene liquor which contains 1.825 g of the dyestuff of the formula blue 10 g/l of the addition product of 9 mols of ethylene oxide to nonylphenol and 15 ml/l of water. The liquor ratio is 1:40.
  • the fabric is introduced into the liquor at 40C, the system is heated to C over the course of 30 minutes, and dyeing takes place for 30 minutes at this temperature. The dyeing takes place for 30 minutes at this temperature. The dyeing is finished by centrifuging off the solvent and drying with warm air.
  • Table 5 contains the fastness properties of the dyeings (a) to (e).
  • Process for improving the wet fastness properties of dyeings on synthetic polyamide fibres which comprises applying to the fibres at temperature of 20 to C a) simultaneously with the dyestuffs in organic solvent, or b) as after-treating of dyeings produced in organic solvent or aqueous liquors, a preparation which contains as fixing agents water-soluble anionic polycondensation products of arylsulphonic acids and/or diarylsulphones with formaldehyde, an organic solvent or solvent mixture and at most percent of water, relative to the preparation.
  • the fixing agents are condensation products of diarylsulphones, possessing at least one phenolic hydroxyl group, with formaldehyde.
  • organic solvents are l,l,l-trichloroethane, trichloroethylene and/or perchloroethylene.
  • dispersing agents aresurface-active, organo-soluble non-ionic or anionic compounds, which in particular are obtained by addition of ethylene oxide to long-chain amines, alcohols, phenols or fatty acid esters.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
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US00174534A 1970-09-03 1971-08-24 Process for improving the wet fastness properties of dyeings on polyamide fibre material Expired - Lifetime US3765839A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1314570A CH541018A (de) 1970-09-03 1970-09-03 Verfahren zur Verbesserung der Nassechtheiten von Färbungen auf Polyamidfasermaterial

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US (1) US3765839A (enrdf_load_stackoverflow)
AT (1) AT329009B (enrdf_load_stackoverflow)
BE (1) BE772082A (enrdf_load_stackoverflow)
CA (1) CA980510A (enrdf_load_stackoverflow)
CH (2) CH541018A (enrdf_load_stackoverflow)
CS (1) CS152404B2 (enrdf_load_stackoverflow)
DE (1) DE2143667C3 (enrdf_load_stackoverflow)
ES (1) ES394745A1 (enrdf_load_stackoverflow)
FR (1) FR2105217B1 (enrdf_load_stackoverflow)
GB (1) GB1349176A (enrdf_load_stackoverflow)
NL (1) NL7112089A (enrdf_load_stackoverflow)
PL (1) PL81815B1 (enrdf_load_stackoverflow)
ZA (1) ZA715654B (enrdf_load_stackoverflow)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3936268A (en) * 1974-11-07 1976-02-03 Diamond Shamrock Corporation Method of reducing barre in synthetic polymide textiles dyed with acid dyes
US4302203A (en) * 1979-11-23 1981-11-24 Apex Chemical Company, Inc. Process for modifying wool to render it flame resistant
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
EP0235980A1 (en) * 1986-02-14 1987-09-09 E.I. Du Pont De Nemours And Company Textiles having stain resistance
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
US5178788A (en) * 1990-11-08 1993-01-12 Texaco Chemical Company Co-solvent system for removing cured fiberglass resin and cured flexible or rigid urethane foams from substrates
US5182154A (en) * 1983-12-16 1993-01-26 Monsanto Company Stain resistant nylon carpets

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US27386A (en) * 1860-03-06 Mill-spindle
US3118723A (en) * 1961-02-08 1964-01-21 Arthur J I Harding Process for dyeing nylon to produce multi-colored dyeings
US3524718A (en) * 1965-07-09 1970-08-18 Geigy Ag J R Processes for the continuous dyeing and printing of cellulose ester fiber material
US3663157A (en) * 1966-06-03 1972-05-16 Ciba Ltd Disperse or monosulfonated acid dye printed nylon resisted with hydroxy diaryl sulfone-formaldehyde condensate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB715919A (en) * 1952-03-24 1954-09-22 Ici Ltd Process for improving the fastness of dyeings
CH378849A (de) * 1962-07-31 1964-03-13 Geigy Ag J R Verfahren zur Fertigstellung von Färbungen und Drucken mit Reaktivfarbstoffen auf natürlichen oder synthetischen Polyamidfasern
BE637209A (enrdf_load_stackoverflow) * 1962-09-18
FR1535352A (fr) * 1966-09-01 1968-08-02 Henkel & Cie Gmbh Procédé de teinture d'une matière fibreuse dans des solvants organiques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US27386A (en) * 1860-03-06 Mill-spindle
US3118723A (en) * 1961-02-08 1964-01-21 Arthur J I Harding Process for dyeing nylon to produce multi-colored dyeings
US3524718A (en) * 1965-07-09 1970-08-18 Geigy Ag J R Processes for the continuous dyeing and printing of cellulose ester fiber material
US3663157A (en) * 1966-06-03 1972-05-16 Ciba Ltd Disperse or monosulfonated acid dye printed nylon resisted with hydroxy diaryl sulfone-formaldehyde condensate

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3936268A (en) * 1974-11-07 1976-02-03 Diamond Shamrock Corporation Method of reducing barre in synthetic polymide textiles dyed with acid dyes
US4302203A (en) * 1979-11-23 1981-11-24 Apex Chemical Company, Inc. Process for modifying wool to render it flame resistant
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
EP0235980A1 (en) * 1986-02-14 1987-09-09 E.I. Du Pont De Nemours And Company Textiles having stain resistance
US4680212A (en) * 1986-03-06 1987-07-14 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
USRE33365E (en) * 1986-03-06 1990-10-02 Monsanto Company Stain resistant nylon fibers
US4800118A (en) * 1987-11-04 1989-01-24 West Point Pepperell Compositions and methods for imparting stain resistance to textile articles
US5178788A (en) * 1990-11-08 1993-01-12 Texaco Chemical Company Co-solvent system for removing cured fiberglass resin and cured flexible or rigid urethane foams from substrates

Also Published As

Publication number Publication date
ES394745A1 (es) 1974-02-16
BE772082A (fr) 1972-03-02
CS152404B2 (enrdf_load_stackoverflow) 1973-12-19
DE2143667C3 (de) 1974-07-18
ZA715654B (en) 1972-07-26
ATA766871A (de) 1975-07-15
CH541018A (de) 1973-01-31
NL7112089A (enrdf_load_stackoverflow) 1972-03-07
CH1314570A4 (enrdf_load_stackoverflow) 1973-01-31
FR2105217B1 (enrdf_load_stackoverflow) 1974-04-05
DE2143667A1 (de) 1972-03-09
GB1349176A (en) 1974-03-27
FR2105217A1 (enrdf_load_stackoverflow) 1972-04-28
DE2143667B2 (de) 1973-12-20
PL81815B1 (enrdf_load_stackoverflow) 1975-08-30
AT329009B (de) 1976-04-26
CA980510A (en) 1975-12-30

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