US3276839A - Process of treating synthetic polyamide textile materials with unsubstituted polyvalent phenols - Google Patents

Process of treating synthetic polyamide textile materials with unsubstituted polyvalent phenols Download PDF

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Publication number
US3276839A
US3276839A US331130A US33113063A US3276839A US 3276839 A US3276839 A US 3276839A US 331130 A US331130 A US 331130A US 33113063 A US33113063 A US 33113063A US 3276839 A US3276839 A US 3276839A
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US
United States
Prior art keywords
phenol
anion
textile materials
aliphatic
bath
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
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US331130A
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English (en)
Inventor
Fruh Georg
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.)
Glanzstoff AG
Vereinigte Glanzstoff Fabriken AG
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Glanzstoff AG
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Publication of US3276839A publication Critical patent/US3276839A/en
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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
    • D06P1/44—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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65118—Compounds containing hydroxyl groups
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/152—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • Y10S8/91—Soap
    • Y10S8/911—Sulfonated
    • 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
    • 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
    • Y10S8/93—Pretreatment before dyeing

Definitions

  • the present invention is directed to a finishing and dyeing process for textile materials. More particularly, the subject invention delates to a finishing and dyeing process for threads, yarns, woven and knit-ted products which are made from synthetic polyarnides.
  • Textile materials commonly are not only dyed but are also subjected to other finishing operations in order to improve the feel, appearance, and wearing ability of such materials.
  • stockings which are made from polyamides, such as nylon, customarily are fixed with saturated steam or hot air to preserve their shape and to make the stockings soft to the touch.
  • the softness and feel of such products can be improved even more by the use of particular softening agents.
  • Organic swelling agents such as phenols or their aqueous solutions also improve the surface properties and increase the dye absorption of synthetic polyamides.
  • the present invention comprises the discovery that polyamide products having excellent properties can be produced if an unsubstituted polyvalent phenol and an aliphatic, anion-active compound is present in the finishing or dyeing bath and if the dyeing or finishing operation is carried out in an alkaline medium.
  • the simultaneous presence of the phenol and the anion-active compound is of critical importance. If the textile materials are finished and dyed in successive steps, it is satisfactory to add the phenol .and the aliphatic, anion-active compound only to the finishing bath. In this case the finishing operation prepares the textile material in such a manner that under ordinary dyeing conditions and without other special components being present, unobjectionable dyeing takes place and the finished product has a satisfactory feel and appearance.
  • anion-active compound in an alkaline medium not only have a uniform color but also demonstate other valuable properties which distinguish such products from those treated only with a phenol.
  • knitted articles of polyamide thread particularly ladies hose, when treated with a solution containing an unsubstituted polyvalent phenol and a hard soap at a pH of between 7 and 8 maintain their silklike feel and sheen after repeated washings. Furthermore, the appearance of such products gives the impression that they have been treated with a softener. The danger of runs or snags in the case of knitted articles is also reduced by about one-third.
  • Another manufacturing advantage which is realized with respect to stockings treated with the phenol and aliphatic, anion-active compound in an alkaline medium is that such stockings can be removed from their forms without difficulty and without the use of a particular softener. This advantage is not obtain-able using phenol alone. For this reason the forming and fixing of the stockings may advantageously take place at the end of the manufacturing process as so-called postboa-rding.
  • the possibility of combining the finishing and the dyeing steps simplifies the manufacture of the products and ofiers economic advantages in comparison with prior art processes in which the woven or knitted articles are especially treated after dyeing in order to make them suitable for sale and wear.
  • Textile materials of synthetic polyamides which are finished or dyed in accordance with this invention have particularly advantageous properties when they are treated in the presence of ortho, meta and para-dihyd-roxy benzenes.
  • the heat resistance of such materials is greatly increased.
  • Threads of hexamet-hylene diamine-adipic acid-polycondensation products or of polycaprolactam which are finished in the presence of ortho-dihydroxy benzene demonstrate little, if .any, decrease in tensile strength after heating for one hour at 200 C.
  • the tensile strength of untreated threads of the same type drop from 20% to 40% of the original tensile strength when subjected to the same heat conditions.
  • the method of carrying out the subject process is quite simple, especially when the finishing step is combined with the dyeing s-tep.
  • stockings made of polyamide threads, after p-resetting (steaming) and sewing can be boiled for one hour in a solution of 10 grams per liter of phenol and 2.5 grams per liter of soap after which they are rinsed and dyed in a fresh bath.
  • the operation is carried out at an alkaline pH of between 7 and 8 which is the value of the solution if alkali metal salts of higher fatty acids are used as the aliphatic, anionactive compound. If another aliphatic, anion-active compound is used, such .as a .sulfated fatty alcohol, however, the proper pH value is obtained by adding a caustic sodium solution or soda to the treating agent.
  • the subject process is suitable for use in connection with dispersion dyes, 2:1 complex dyes, acid dyes, or substantive dyes.
  • dispersion dyes 2:1 complex dyes, acid dyes, or substantive dyes.
  • the use of such dyes in connection with polyamides is well known in the art.
  • Unsubstituted polyvalent phenols which can be used in the subject process include pyrocatechol, resorcinol, and hydroquinone which are also known as ortho, meta and para-dihydroxy benzenes, as well as pyrogallol and phloroglucinol.
  • My preferred materials are ortho, meta and para-dihydroxy benzenes and the most preferred material is ortho-dihydroxy benzene.
  • anionic compounds can be used in the subject invention.
  • Surface active agents are placed in one of three categories. These agents are either anionic, cationic, or nonionic in character. If the elongated, low afiinity portion of the molecule of the compound is included in the anion in aqueous solution, the substance is termed anion-active or anionic.
  • the most common anionic aliphatic compounds are soaps such as the alkali metal salts of fatty acids. Such soaps are formed from fatty acids containing from 8 to 22 carbon atoms and preferably from 12 to 18 carbon atoms. The fatty acids can be both saturated and unsaturated. Illustrative examples of soaps would include sodium and potassium, laurate, myristate, palmitate, stearate, and oleate.
  • anion-active aliphatic compounds include sulfated fatty acids containing from 8 to 22 carbon atoms, and preferably from 12 to 18 carbon atoms, sulfated fatty alcohols containing from 8 to 22 carbon atoms, and preferably from '12 to 18 carbon atoms.
  • anion-active aliphatic compounds can include the sulfates or sulfona-tes of lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, dodecyl alcohol, tetradecyl alcohol, cetyl alcohol, octadecyl alcohol, oleyl alcohol, and mixtures thereof.
  • Example in this example 60 denier polyamide threads in the hank were dyed in a bath containing grams per liter pyrocatechol (brenzcatechin) 2.5 grams per liter hard soap (sodium stearate) 1% Cibalan grey BL The temperature of the bath was raised from room temperature to boiling and was held at this temperature for one hour. Thereafter the threads were rinsed in the customary manner. The threads had .a silklike and subof from about to 30 C. is brought to a boil in the course of from about 30 to 60 minutes, and is maintained at that temperature for from one-half to two hours.
  • the pH of the bath should be between about 7 and 8. If soaps are used as the treating agent, the pH of the bath will be maintained within this range without the addition of other materials. If sulfated alcohols, or the like, are used, however, it may be necessary to adjust the pH of the bath by the addition of caustic soda or some other alkaline compound.
  • the finishing or dye bath should contain from about 9 to 11 grams per liter of phenol, and preferably 10 grams per liter of phenol, and should contain from about 1.5 to 3 grams per liter of the anion-active aliphatic compound, and preferably from 2 to 2.5 grams per liter of the anion-active aliphatic compound.
  • the important features of the invention arethe simultaneous use of thephenol and aliphatic, anion-active compound in treating synthetic polyamide, and the fact that the treating bath should be maintained at a pH of between about 7 and 8.
  • Any anionic aliphatic compound bearing .a hydrocarbon chain of from 8 to 22 carbon atoms, and perferably from 12 to 18 carbon atoms, can be used in the process.
  • the hydrocarbonchain can either be saturated or olefinically unsaturated.
  • a process for finishing textile materials of synthetic polyamides which comprises: contacting said polyamide with a 'boilingbath containing an unsubstituted p'olyvalent phenol and an aliphatic anion-active compound, at a pH of between about 7 and 8.
  • a process for finishing textile materials of synthetic polyamides which comprises: contacting said polyamide with a boiling bath containing an unsubstituted polyvalent phenol selected from the group consisting of pyrocatechol, resorcinol, :hydroquinone, pyrogallol, and phloroglucinol, and an aliphatic anion-active compound selectedfrom the group consisting of alkali metal salts of fatty acids containing from 8 to 22 carbon atoms, sulfated fatty acids containing from 8 to 22 carbon atoms, and sulfated fatty alcohols containing from 8 to 22 carbon atoms.
  • an unsubstituted polyvalent phenol selected from the group consisting of pyrocatechol, resorcinol, :hydroquinone, pyrogallol, and phloroglucinol
  • an aliphatic anion-active compound selectedfrom the group consisting of alkali metal salts of fatty acids containing from 8 to 22 carbon

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US331130A 1960-08-24 1963-12-17 Process of treating synthetic polyamide textile materials with unsubstituted polyvalent phenols Expired - Lifetime US3276839A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEV19239A DE1200784B (de) 1960-08-24 1960-08-24 Verfahren zum Faerben und Veredeln von Textilien aus synthetischen Polyamiden

Publications (1)

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US3276839A true US3276839A (en) 1966-10-04

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US331130A Expired - Lifetime US3276839A (en) 1960-08-24 1963-12-17 Process of treating synthetic polyamide textile materials with unsubstituted polyvalent phenols

Country Status (5)

Country Link
US (1) US3276839A (de)
BE (1) BE606961A (de)
CH (1) CH376468A (de)
DE (1) DE1200784B (de)
GB (1) GB923468A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3736097A (en) * 1971-01-05 1973-05-29 Johnson & Johnson Process employing aqueous media in the treatment of fibrous materials

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB760205A (en) * 1953-12-30 1956-10-31 Louis Marie Philippe Maurice L Improvements in the methods for producing threads of a woolly character and threads obtained through said methods
FR1122759A (fr) * 1954-04-29 1956-09-12 Ciba Geigy Procédé de teinture de fibres en superpolyamides se teignant avec formation de stries

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3736097A (en) * 1971-01-05 1973-05-29 Johnson & Johnson Process employing aqueous media in the treatment of fibrous materials

Also Published As

Publication number Publication date
GB923468A (en) 1963-04-10
DE1200784B (de) 1965-09-16
CH376468A (de) 1963-12-31
BE606961A (fr) 1961-12-01

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