US20050120490A1 - Process for improving the sun protection factor of cellulosic fibre material - Google Patents

Process for improving the sun protection factor of cellulosic fibre material Download PDF

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Publication number
US20050120490A1
US20050120490A1 US10/507,954 US50795404A US2005120490A1 US 20050120490 A1 US20050120490 A1 US 20050120490A1 US 50795404 A US50795404 A US 50795404A US 2005120490 A1 US2005120490 A1 US 2005120490A1
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US
United States
Prior art keywords
formula
alkyl
process according
compound
cellulosic fibre
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.)
Abandoned
Application number
US10/507,954
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English (en)
Inventor
Georges Metzger
Fabienne Cuesta
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BASF Corp
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of US20050120490A1 publication Critical patent/US20050120490A1/en
Assigned to CIBA SPECIALTY CHEMICALS CORP. reassignment CIBA SPECIALTY CHEMICALS CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CUESTA, FABIENNE, METZGER, GEORGES
Priority to US11/650,009 priority Critical patent/US7407519B2/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/68—Triazinylamino stilbenes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • 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
    • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • D06M13/03—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons with unsaturated hydrocarbons, e.g. alkenes, or alkynes
    • D06M13/07—Aromatic hydrocarbons
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments

Definitions

  • the present invention relates to a process for improving the sun protection factor (SPF) of cellulosic fibre materials and blends thereof, which comprises treating the cellulosic fibre materials with at least one fluorescent whitening agent (FWA).
  • FWA fluorescent whitening agent
  • the invention moreover relates to new fluorescent whitening agents useful for that process.
  • UV radiation The skin-damaging effect of UV radiation is well known. Protection from strong sunlight is usually sought by applying a sun cream, a composition that contains a UV absorber, directly to the skin. In particularly sunny regions, for example in Australia or America, however, the rate of skin damage due to UV radiation has recently been increasing dramatically. Accordingly, more attention is paid in these countries to protecting the skin from solar irradiation.
  • the skin should be protected not just directly, but also to reduce the UV transmissibility of the clothing and also of other sun protection articles, such as awnings or parasols.
  • cellulosic fibre materials are at least partially transparent to UV radiation, so that the mere wearing of clothing does not offer adequate protection to the skin from damage due to UV radiation.
  • a remedy is possible here by incorporating UV absorbers and/or FWA's into the fibre material.
  • the present invention provides a process for improving the sun protection factor (SPF) of cellulosic fibre materials and blends thereof, which comprises contacting said materials with at least one compound of the formula in which M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine;
  • SPF sun protection factor
  • R 2 and R 2 ′ can have different meanings. Preferably, however, they are identical.
  • alkyl radicals are to be understood as being generally open-chain or branched alkyl radicals containing from 1 to 6 carbon atoms, for example methyl, ethyl, n- or iso-propyl, n-, sec- or tert-butyl or n-hexyl, n-octyl.
  • Cycloalkyl is preferably cyclopentyl or cyclohexyl.
  • alkyl groups can be substituted, e.g. by C 1 -C 4 alkoxy or hydroxy.
  • R 3 as aryl is preferably independently of each other phenyl or naphthyl.
  • R 1 and R 1 ′ are identical and especially preferred is the use of a compound of formula (1), wherein R 1 and R 1 ′ are each —NH—R 3 , —N(R 3 ) 2 or —O—R 3 , wherein R 3 is phenyl substituted by —CO—X—R 5 , wherein X is O or NH and R 5 is optionally substituted C 1 -C 4 -alkyl.
  • R 1 and R 1 ′ are —NH—R 3 , wherein R 3 is phenyl substituted by —CO—X—R 5 , wherein X is O or NH and R 5 is 2-hydroxyethyl.
  • R 4 is preferably C 1 -C 4 -hydroxyalkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl. Most preferably R 4 is hydroxyethyl, hydroxypropyl, hydroxybutyl or ethoxyethyl.
  • novel compounds of formula (1) are a further embodiment of the invention.
  • R 1 and R 1 ′ are identical and are each —NH—R 3 , —N(R 3 ) 2 or —O—R 3 , wherein R 3 is phenyl substituted by —CO—X—R 5 , wherein X is O or NH and R 5 is optionally substituted C 1 -C 4 -alkyl,
  • the quantities of compound (1) to be applied to the cellulosic material according to the process of the invention may vary over a wide range. However, when used in amounts of between 0.001 and 2% by weight, based on the weight of the fibre material, useful effects may be obtained. Preferably, however, the amount of the compound of formula (1) used is from 0.005 to 1% and especially from 0.01 to 0.5% by weight, based on the weight of the fibre material.
  • Cellulosic fibre materials are to be understood as meaning, for example, the natural cellulose fibre, such as cotton, linen and hemp, and also cellulose pulp and regenerated cellulose.
  • the process of the invention is also suitable for treating hydroxyl-containing fibres present in blend fabrics, for example, blends of cotton with polyester fibres or polyamide fibres.
  • the fibre materials used have a density of between 30 and 200 g/m 2 , preferably between 100 and 150 g/m 2 , the porosity of the material lying in the range of 0.1 to 3%, preferably 0.1 to 1.5%.
  • the cellulosic fibre material used is cotton or a cotton blend.
  • the fibres mentioned may be present in various forms, for example, as staple or yarns or as wovens or knits.
  • a UV absorber may also be employed to the cellulosic fibre material. Usually little or no observable reduction of the degrees of whiteness of the so-treated materials results.
  • application of the UV absorber may be performed before, during or after treatment of the material with the FWA of formula (1).
  • any UV absorber suitable for cellulosic fibre materials may be applied for this purpose.
  • the UV absorber used may be, e.g., an o-hydroxybenzophenone, an o-hydroxy-phenylbenzotriazole, a 2-aryl-2H-benzotriazole, a salicylic acid ester, a substituted acrylonitrile, a substituted acrylaminoethylene, a nitrilohydrazone, o-hydroxyaryl-1,3,5-triazine, a sulphonated 1,3,5-triazine or preferably an oxalic anilide.
  • UV absorbers are used and particularly preferred are the UV absorbers described in the U.S. Pat. No. 5,700,295, especially the oxalic anilides.
  • the liquor ratio can be chosen within a wide range, for example, from 3:1 to 200:1, preferably from 10:1 to 40:1. It is advantageous to operate at a temperature of 20 to 120° C., preferably 40 to 110° C.
  • the fibre-reactive UV absorbers are applied advantageously in the presence of acid-binding agents, for example, sodium hydroxide, sodium carbonate, sodium bicarbonate, sodium formate, potassium carbonate, sodium silicate, sodium trichloroacetate or sodium triphosphate, in the presence or absence of neutral salts, for example, sodium sulphate or sodium chloride.
  • acid-binding agents for example, sodium hydroxide, sodium carbonate, sodium bicarbonate, sodium formate, potassium carbonate, sodium silicate, sodium trichloroacetate or sodium triphosphate
  • neutral salts for example, sodium sulphate or sodium chloride.
  • the quantities of the UV absorbers to be applied to the cellulosic material according to the process of the invention may vary over a wide range. However, when used in amounts of between 0.005 and 1% by weight, based on the weight of the fibre material, useful effects may be obtained. Preferably, however, the amount of the compound of formula (1) used is from 0.01 to 0.5% by weight, based on the weight of the fibre material.
  • the liquor add-on is advantageously 40-700, preferably 40-500,% by weight.
  • the fibre material is then subjected to a heat treatment process to fix the applied FWA's and UV absorbers. This fixing can also be effected by the cold batching method.
  • the heat treatment preferably takes the form of a steaming process in a steamer with ordinary or superheated steam at a temperature of 98 to 105° C. for, for example, 1-7, preferably 1-5 minutes.
  • the fixing of the UV absorber by the cold batching process can be effected by storing the impregnated and preferably rolled-up material at room temperature (15 to 30° C.) for 3 to 24 hours, for example, the cold batching time being known to depend on the UV absorber.
  • the treated materials are conventionally rinsed, soaped, for example, for 20 minutes at 90° C. with a solution containing 1 g/l. of calcined sodium carbonate, and dried.
  • the treatment bath may optionally contain other customary auxiliaries, for example, levelling, wetting deaerating and antifoaming agents, penetration accelerants or crease resisting agents.
  • the cellulose fibre materials treated by the process of the present invention possess high sun protection factors.
  • the sun protection factor is defined as the ratio of the harmful dose of UV energy on protected skin to the harmful dose of UV energy on unprotected skin. Accordingly, a sun protection factor is also a measure of the transmissivity of fibre materials untreated and of those treated with FWA's and reactive UV absorbers described in this invention.
  • the sun protection factor can be determined, for example, by the method described by B. L. Diffey and J. Robson in J.Soc.Cosmet.Chem., 40, 127-133 (1989).
  • the fluorescent whitening agents of formula (1) are new and are a further subject of the present invention.
  • the invention thus also provides compounds of formula in which M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine;
  • the compounds of formula (1) can be prepared by known methods, e.g., by reacting, under known reaction conditions, cyanuric chloride, successively, in any desired sequence, with each of an aminostilbene-disulfonic acid and compounds capable of introducing the groups R 1 , R 1 ′, R 2 and R 2 ′. If R 2 and/or R 2 ′.has the meaning —O—R 4 conveniently an alcohol of the formula HO—R 4 is used. If this alcohol contains an additional hydroxy residue, usually mixtures of compounds of formula (1) are obtained. The specific composition of those mixtures depends on the reactivity of the different OH-residues of the alcohol. It is, however, usually not necessary to isolate the individual components of such mixtures as all the components exhibit similar advantageous properties as fluorescent whitening agents. If desired, isolation can be afforded by known methods.
  • the compounds of formula (1) exhibit distinguished solubility in water combined with good affinity to cellulosic fibre material and aqueous formulations containing these compounds have excellent storage stability. They confer to the cellulosic material excellent sun protection and a high degree of whiteness.
  • reaction mixture When the addition is complete, the reaction mixture is stirred for another 1 hour at 60° C. HPLC showes that the reaction is complete, 94-95% purity. Temperature of the reaction mixture is increased to 90° C. The viscosity of the reaction mixture increases and the pH droppes to 5.32. Then pH is adjusted with 1 M sodium carbonate to 6.0.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Artificial Filaments (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
US10/507,954 2002-03-18 2003-03-10 Process for improving the sun protection factor of cellulosic fibre material Abandoned US20050120490A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/650,009 US7407519B2 (en) 2002-03-18 2007-01-05 Process for improving the sun protection factor of cellulosic fibre material

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP02405205 2002-03-18
EP02405205.2 2002-03-18
PCT/EP2003/002440 WO2003078724A1 (en) 2002-03-18 2003-03-10 A process for improving the sun protection factor of cellulosic fibre material

Related Child Applications (1)

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US11/650,009 Continuation US7407519B2 (en) 2002-03-18 2007-01-05 Process for improving the sun protection factor of cellulosic fibre material

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US20050120490A1 true US20050120490A1 (en) 2005-06-09

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US11/650,009 Expired - Fee Related US7407519B2 (en) 2002-03-18 2007-01-05 Process for improving the sun protection factor of cellulosic fibre material

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US (2) US20050120490A1 (enExample)
EP (1) EP1485532B1 (enExample)
JP (1) JP4359148B2 (enExample)
AT (1) ATE541985T1 (enExample)
AU (1) AU2003227043A1 (enExample)
ES (1) ES2377961T3 (enExample)
TW (1) TWI280975B (enExample)
WO (1) WO2003078724A1 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060048309A1 (en) * 2002-12-10 2006-03-09 Jean-Jacques Donze Mixtures of fluorescent whitening agents
US20060197060A1 (en) * 2003-08-21 2006-09-07 Goetz Scheffler Optical brighteners
US20120211188A1 (en) * 2009-09-17 2012-08-23 Blankophor Gmbh & Co. Kg Disulfo-type fluorescent whitening agents

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI20085345A7 (fi) * 2008-04-22 2009-10-23 Kemira Oyj Menetelmä valon aikaansaaman ligniinipitoisen materiaalin kellertymisen vähentämiseksi

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5700295A (en) * 1994-10-13 1997-12-23 Ciba Specialty Chemicals Corporation UV absorbers, their preparation and the use thereof
US5744599A (en) * 1995-02-22 1998-04-28 Ciba Specialty Chemicals Corporation Triazinyldiaminostilbene compounds useful as ultraviolet absorbers and as fluorescent whitening agents
US20030192137A1 (en) * 2000-07-20 2003-10-16 Fabienne Cuesta Method for the fluorescent whitening of cotton

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2335570A1 (de) 1972-07-21 1974-01-31 Ciba Geigy Ag Verfahren zur herstellung von bistriazinylamino-stilben-disulfonsaeuren(2,2'), neue bis-triazinyl-amino-stilbendisulfonsaeuren-(2,2'), sowie deren verwendung als optische aufheller fuer organische materialien
CH640899A5 (en) 1979-05-14 1984-01-31 Ciba Geigy Ag Stable stilbene brightener solutions
GB9409466D0 (en) * 1994-05-12 1994-06-29 Ciba Geigy Ag Textile treatment
GB9726365D0 (en) * 1997-12-13 1998-02-11 Ciba Sc Holding Ag Compounds
PL353873A1 (en) * 1999-09-10 2003-12-01 Ciba Specialty Chemicals Holding Inc.Ciba Specialty Chemicals Holding Inc. Triazinylaminostilbene derivative as fluorescent whitening agents

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5700295A (en) * 1994-10-13 1997-12-23 Ciba Specialty Chemicals Corporation UV absorbers, their preparation and the use thereof
US5744599A (en) * 1995-02-22 1998-04-28 Ciba Specialty Chemicals Corporation Triazinyldiaminostilbene compounds useful as ultraviolet absorbers and as fluorescent whitening agents
US20030192137A1 (en) * 2000-07-20 2003-10-16 Fabienne Cuesta Method for the fluorescent whitening of cotton

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060048309A1 (en) * 2002-12-10 2006-03-09 Jean-Jacques Donze Mixtures of fluorescent whitening agents
US7497971B2 (en) 2002-12-10 2009-03-03 Ciba Specialty Chemicals Corporation Mixtures of fluorescent whitening agents
US20060197060A1 (en) * 2003-08-21 2006-09-07 Goetz Scheffler Optical brighteners
US7166564B2 (en) 2003-08-21 2007-01-23 Ciba Specialty Chemicals Corp. Optical brighteners
US20120211188A1 (en) * 2009-09-17 2012-08-23 Blankophor Gmbh & Co. Kg Disulfo-type fluorescent whitening agents
US8696867B2 (en) * 2009-09-17 2014-04-15 Blankophor Gmbh & Co. Kg Disulfo-type fluorescent whitening agents

Also Published As

Publication number Publication date
US20070107137A1 (en) 2007-05-17
JP4359148B2 (ja) 2009-11-04
ATE541985T1 (de) 2012-02-15
US7407519B2 (en) 2008-08-05
JP2005520942A (ja) 2005-07-14
TW200307034A (en) 2003-12-01
AU2003227043A1 (en) 2003-09-29
EP1485532A1 (en) 2004-12-15
TWI280975B (en) 2007-05-11
EP1485532B1 (en) 2012-01-18
WO2003078724A1 (en) 2003-09-25
ES2377961T3 (es) 2012-04-03

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