EP0708197A2 - Utilisation d'hydroxybenztriazoles pour l'augmentation de l'indice de protection solaire de matériaux fibreux cellulosiques - Google Patents

Utilisation d'hydroxybenztriazoles pour l'augmentation de l'indice de protection solaire de matériaux fibreux cellulosiques Download PDF

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Publication number
EP0708197A2
EP0708197A2 EP95810591A EP95810591A EP0708197A2 EP 0708197 A2 EP0708197 A2 EP 0708197A2 EP 95810591 A EP95810591 A EP 95810591A EP 95810591 A EP95810591 A EP 95810591A EP 0708197 A2 EP0708197 A2 EP 0708197A2
Authority
EP
European Patent Office
Prior art keywords
naphthyl
sulfo
substituted
alkyl
unsubstituted
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.)
Pending
Application number
EP95810591A
Other languages
German (de)
English (en)
Other versions
EP0708197A3 (fr
Inventor
Francesco Dr. Fuso
Gerhard Dr. Reinert
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 Geigy AG
Ciba Spezialitaetenchemie Holding 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 Geigy AG, Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Geigy AG
Publication of EP0708197A2 publication Critical patent/EP0708197A2/fr
Publication of EP0708197A3 publication Critical patent/EP0708197A3/fr
Pending legal-status Critical Current

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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
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358—Triazines
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/35—Heterocyclic compounds
    • 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
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds

Definitions

  • the present invention relates to the use of hydroxybenzotriazole compounds for improving the sun protection factor of cellulose-containing fiber materials by treating these fiber materials with certain compounds from the class of the hydroxybenzotriazoles.
  • R1 and R2 are independently hydrogen; C1-C4 alkyl; C1-C4 alkoxy; Halogen; Hydroxy; Nitro; Are sulfo or carboxy;
  • R3 is hydrogen; or is C1-C4-alkyl which is unsubstituted or substituted by C1-Coxy-alkoxy, halogen, hydroxy, sulfo, cyano, carboxy, C1-C4-alkoxycarbonyr, C1-C4-alkylcarbonyloxy, carbamoyl or sulfamoyl; A unsubstituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, halogen or sulfo; unsubstituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, halogen or sulfo naphthylene or unsubstituted or substitute
  • R1, R2, R3, R4, R5, R6 and R7 are as C1-C4-alkyl independently of one another methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
  • R1 and R2 are independently of one another as C1-C4 alkoxy e.g. Methoxy, ethoxy, propoxy, isopropoxy, isobutoxy or tert.butoxy.
  • R1 and R2 are independently halogen, e.g. Fluorine, chlorine or bromine.
  • R3, R5, R6 and R7 are, as C1-C4-alkoxy-C1-C4-alkyl, independently of one another, e.g. Methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl.
  • R3 as halogen-C1-C4-alkyl is e.g. Chloromethyl, chloroethyl, 2-chloroethyl, 2-bromoethyl, 3-chloropropyl, 3-bromopropyl, 4-chlorobutyl or 4-bromobutyl.
  • R3, R5, R6 and R7 are independently hydroxy-C1-C4-alkyl e.g. 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, 2,3-dihydroxypropyl or 3,4-dihydroxybutyl.
  • R3, R5, R6 and R7 are, as sulfo-C1-C4-alkyl independently of each other e.g. Sulfomethyl, 2-sulfoethyl, 3-sulfopropyl or 4-sulfobutyl.
  • R3 as cyano-C1-C4-alkyl is e.g. Cyanomethyl, 2-cyanoethyl or 3-cyanopropyl.
  • R3, R5, R6 and R7 are independently as carboxy-C1-C1-alkyl e.g. Carboxymethyl, 2-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl or 1,2-dicarboxyethyl.
  • R3 as C1-C4-alkoxycarbonyl-C1-C4-alkyl is, for example, methoxycarbonylmethyl, Ethoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 3-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl or 4-ethoxycarbonylbutyl.
  • R3 as C1-C4-alkylcarbonyloxy-C1-C4-alkyl is e.g. Methylcarbonyloxymethyl, ethylcarbonyloxymethyl, 2-methylcarbonyloxyethyl, 2-ethylcarbonyloxyethyl, 3-methylcarbonyloxypropyl, 3-ethylcarbonyloxypropyl, 4-methylcarbonyloxybutyl or 4-ethylcarbonyloxybutyl.
  • R3 as carbamoyl-C1-C4-alkyl is e.g. Carbamoylmethyl, 2-carbamoylethyl, 3-carbamoylpropyl or 4-carbamoylbutyl.
  • R3 as sulfamoyl-C1-C4-alkyl is e.g. Sulfamoylmethyl, 2-sulfamoylethyl, 3-sulfamoylpropyl or 4-sulfamoylbutyl.
  • R5, R6 and R7 are, as C1-C4-alkylphenyl, independently of one another, e.g. Tolyl, xylyl, mesityl, cumyl, ethylphenyl or butylphenyl.
  • R5, R6 and R7 are, as C1-C4-alkoxyphenyl, independently of one another, e.g. Methoxyphenyl, ethoxyphenyl, propoxyphenyl or butoxyphenyl.
  • R5, R6 and R7 are independently of one another as halophenyl, e.g. Chlorophenyl or bromophenyl.
  • R5, R6 and R7 are independently as C1-C4-alkyl-naphthyl e.g. Methylnapthyl, ethylnapthyl, propylnapthyl or butylnapthyl.
  • R5, R6 and R7 are, as C1-C4-alkoxy-naphthyl, independently of one another, e.g. Methoxynapthyl, ethoxynapthyl, propoxynapthyl or butoxynapthyl.
  • R5, R6 and R7 are, as C1-C4-alkyl-benzyl, independently of one another, e.g. Methylbenzyl, ethylbenzyl, propylbenzyl or butylbenzyl.
  • R5, R6 and R7 are as C1-C4 alkoxy-benzyl independently of one another, for example, methoxybenzyl, ethoxybenzyl, propoxybenzyl or butoxybenzyl.
  • R 'as C1-C6 alkyl is e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl.
  • a as C1-C4 alkyl phenylene is e.g. Tolylene, xylylene, mesitylene, cumylene, ethylphenylene or butylphenylene.
  • a as C1-C4 alkoxy phenyl is e.g. Methoxyphenylene, ethoxyphenylene, propoxyphenylene or butoxyphenylene.
  • a as halophenylene is e.g. Chlorophenylene or bromophenylene.
  • a as C1-C4 alkyl naphthylene is e.g. Methyl naphthylene, ethyl naphthylene, propyl naphthylene or butyl naphthylene.
  • a as C1-C4 alkoxy-naphthylene is e.g. Methoxy naphthylene, ethoxy naphthylene, propoxy naphthylene or butoxy naphthylene.
  • a as C1-C12 alkylene is e.g. Methylene, ethylene, propylene, tetramethylene, pentamethylene or hexamethylene.
  • A can be substituted one or more times as substituted phenylene by the substituents mentioned.
  • A can be substituted one or more times as substituted naphthylene by the substituents mentioned.
  • R 5, R6 or R7 are substituted phenyl
  • the phenyl radical can be substituted one or more times by the substituents mentioned.
  • R5, R6 or R7 are substituted naphthyl
  • the naphthyl radical can be substituted one or more times by the substituents mentioned.
  • R5, R6 or R7 stand for substituted benzyl
  • the benzyl radical in the phenyl ring can be substituted one or more times by the substituents mentioned.
  • the compounds of formula (1) as well as their preparation are e.g. known from JP Kokai Hei 3-239757 and JP Kokai Hei 3-241069.
  • Cellulose-containing fiber materials are understood to mean, for example, the natural cellulose fiber, such as cotton, linen and hemp, as well as cellulose and regenerated cellulose.
  • the compounds of formula (1) are also suitable for treating hydroxyl-containing fibers contained in blended fabrics, e.g. of mixtures of cotton with polyester fibers or polyamide fibers. Fiber materials with a density between 30 and 200 g / m are preferred.
  • the preferred cellulose-containing fiber material is cotton.
  • the fibers mentioned can be in various forms, e.g. Threads or yarns, or as a woven or knitted fabric.
  • the compounds of the formula (1) can be applied to the fiber material and fixed on the fiber in various ways customary in the textile industry, in particular in the form of aqueous solutions. They are suitable, for example, for the padding process or preferably for the exhaust process.
  • the extraction process is carried out at a temperature between 50 and 120 ° C, advantageously between 50 and 70 ° C in the presence of acid-binding additives such as sodium carbonate, sodium bicarbonate, sodium formate, potassium carbonate, sodium silicate, sodium trichloroacetate or sodium triphosphate, optionally in the presence of neutral salts such as Sodium sulfate or sodium chloride.
  • the liquor ratio in the exhaust process can be chosen within a wide range, for example 1: 3 to 1: 200, preferably 1:10 to 1:40.
  • the compounds of the formula (1) are used according to the invention in an amount of, for example, 0.005 to 10% by weight, preferably 0.05 to 2% by weight, based on the fiber material.
  • the compounds of the formula (1) can be applied to the fiber material in a separate treatment bath or else in the dye bath, before, during or after the dyeing.
  • the treatment bath or dye bath can optionally also contain other conventional auxiliaries, such as e.g. Wetting, venting and anti-foaming agents or penetration accelerators.
  • the cellulose fiber materials treated with the compounds of the formula (1) are distinguished by a very high sun protection factor.
  • the sun protection factor is defined as the quotient of the harmful UV radiation dose without sun protection and the harmful UV radiation dose with sun protection. Accordingly, a sun protection factor also represents a measure of the permeability of the untreated and treated with the hydroxybenzotriazoles used in this invention fiber materials for UV radiation.
  • the sun protection factor can be determined, for example, according to that of BL Diffey and J. Robson in J. Soc. Cosmet. Chem. 40 , 127-133 (March / June 1989).
  • a sample of 100 g of a bleached cotton tricot is treated at 60 ° C. for 20 minutes at a liquor ratio of 1:15.
  • the liquor contains 1 g of the compound of the formula and 75 g sodium sulfate.
  • 30 g of sodium carbonate are then added to the liquor and the cotton jersey is treated at 60 ° C. for a further 60 minutes.
  • the fiber material is removed from the liquor, washed several times with cold, warm and hot water and dried. You get a cotton jersey with an excellent sun protection factor.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)
EP95810591A 1994-09-29 1995-09-20 Utilisation d'hydroxybenztriazoles pour l'augmentation de l'indice de protection solaire de matériaux fibreux cellulosiques Pending EP0708197A3 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2952/94 1994-09-29
CH295294 1994-09-29
US08/534,523 US5811081A (en) 1994-09-29 1995-09-27 Use of hydroxybenzotriazoles for enhancing the sun protection factor of cellulosic fibre materials

Publications (2)

Publication Number Publication Date
EP0708197A2 true EP0708197A2 (fr) 1996-04-24
EP0708197A3 EP0708197A3 (fr) 1996-08-28

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP95810591A Pending EP0708197A3 (fr) 1994-09-29 1995-09-20 Utilisation d'hydroxybenztriazoles pour l'augmentation de l'indice de protection solaire de matériaux fibreux cellulosiques

Country Status (2)

Country Link
US (1) US5811081A (fr)
EP (1) EP0708197A3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6037280A (en) * 1997-03-21 2000-03-14 Koala Konnection Ultraviolet ray (UV) blocking textile containing particles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003272740A1 (en) * 2002-10-01 2004-04-23 Johnson & Johnson Pharmaceutical Research & Development, L.L.C. 4,6-diaminosubstituted-2-[oxy or aminoxy]-[1,3,5]triazines as protein tyrosine kinase inhibitors

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU631190B2 (en) * 1989-03-14 1992-11-19 Novartis Ag Ultraviolet absorbing lenses and methods of making the same
JP2808791B2 (ja) * 1990-02-15 1998-10-08 住友化学工業株式会社 反応染料混合物及びそれを用いるセルロース系繊維材料の染色または捺染方法
JP2946602B2 (ja) * 1990-02-15 1999-09-06 住友化学工業株式会社 ヒドロキシベンゾトリアゾール化合物およびそれを固着してなる汗耐光性の繊維材料染色物
DE69331830T3 (de) * 1992-08-12 2006-12-14 Clariant Finance (Bvi) Ltd., Road Town Verfahren zur erhöhung des sonnenschutzfaktors und verbindungen geeignet zur erhöhung des sonnenschutzfaktors von fasern und geweben

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6037280A (en) * 1997-03-21 2000-03-14 Koala Konnection Ultraviolet ray (UV) blocking textile containing particles

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Publication number Publication date
EP0708197A3 (fr) 1996-08-28
US5811081A (en) 1998-09-22

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