AU3498899A - Process for improving the photochemical and thermal stability of dyeings and prints on polyester fibre materials - Google Patents

Process for improving the photochemical and thermal stability of dyeings and prints on polyester fibre materials Download PDF

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Publication number
AU3498899A
AU3498899A AU34988/99A AU3498899A AU3498899A AU 3498899 A AU3498899 A AU 3498899A AU 34988/99 A AU34988/99 A AU 34988/99A AU 3498899 A AU3498899 A AU 3498899A AU 3498899 A AU3498899 A AU 3498899A
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Australia
Prior art keywords
formula
compound
polyester fibre
polyester
dyeings
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Abandoned
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AU34988/99A
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Jean-Marie Adam
Jean-Pierre Bacher
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BASF Schweiz AG
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Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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Publication of AU3498899A publication Critical patent/AU3498899A/en
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    • 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
    • C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • 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
    • D06P5/06—After-treatment with organic compounds containing nitrogen
    • 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
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • 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
    • D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
    • D06P5/2066—Thermic treatments of textile materials
    • D06P5/2077—Thermic treatments of textile materials after dyeing
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/42—Cellulose acetate using dispersed dyestuffs
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/46—Cellulose triacetate
    • D06P3/48—Cellulose triacetate using dispersed dyestuffs
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • 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
    • D06P5/001—Special chemical aspects of printing textile materials

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Description

x S F Ref: 463122
AUSTRALIA
PATENTS ACT 1990 COMPLETE SPECIFICATION FOR A STANDARD PATENT
ORIGINAL
_Is Name and Address of Applicant: Ciba Specialty Klybeckstrasse 4057 Basel
SWITZERLAND
Chemicals Holding Inc.
141 Actual Inventor(s): Address for Service: Invention Title: Jean-Marie Adam and Jean-Pierre Bacher Spruson Ferguson, Patent Attorneys Level 33 St Martins Tower, 31 Market Street Sydney, New South Wales, 2000, Australia Process for Improving the Photochemical and Thermal Stability of Dyeings and Prints on Polyester Fibre Materials The following statement is a full description of this invention, including the best method of performing it known to me/us:- 5845 Process for Improving the Photochemical and Thermal Stability of Dyeings and Prints on Polyester Fibre Materials The present invention relates to a process for the photochemical and thermal stabilisation of dyeings and prints on polyester fibre materials and polyester fibre-containing fibre blends, Dyed or printed polyester fibre materials can be damaged by the action of light, in particular with simultaneous action of heat. Effective protection of these dyed fibre materials against UV radiation is essential, for example for use in the automotive sector.
Triazine-based light stabilisers for polyester fibre materials are known. However, the protection of these compounds does not fully meet today's requirements, especially in the automotive sector.
There is thus still a demand for improved protection of these dyeings and prints on polyester fibre materials.
It has now been found that very good protection of dyeings and prints on polyester fibre materials can be obtained with specific derivatives of 2-(2'-hydroxyphenyl)-s-triazine.
Accordingly, this invention relates to a process for the photochemical and thermal stabilisation of dyeings and prints on polyester fibre materials, which comprises treating the polyester fibre materials with a compound of formula *0**0 butyl or tert butyl.
C..
(1) wherein R 1 is C1-C4alkyl, R 1 defined as C1-C4alkyl is methyl, ethyl, propyl, -propyl, n-butyl, sec-butyl, butyl or tert butyl.
20 Compounds preferably used for the novel process are those of formula wherein R 1 is ethyl and, preferably, methyl.
The compounds of formula are known.
This invention also relates to the preparation of the compounds of formula used according to this invention. They are prepared, for example, by reacting o-hydroxybenzamide of formula Oa NH 2 0 (2) 0 with a compound of formula co 1 R wherein Ri has the meaning given for formula at a temperature in the range from 70 to 180 0 C and 0 then reacting the resultant intermediate of formula N (4) then reacting the resultant intermediate of formula o N\C:04546 O NH with a compound of formula NH 2 5 at a temperature in the range from 50 to 80°C. In the process of this invention it is preferred to use compounds of formula wherein R1 is ethyl or, preferably, methyl.
The compounds of formula used according to this invention are used in an amount from 0.01 to 5% by weight, preferably from 0.1 to 3% by weight, based on the weight of the fibre material.
The compounds used according to this invention are sparingly soluble in water and are therefore advantageously applied in disperse form. For this purpose they are ground to a particle size of 1 -2 mm with a corresponding dispersant using eg. quartz balls and a high-speed agitator.
Suitable dispersants for the compounds of formula are for example: acid esters or their salts of alkylene oxide adducts, for example acid esters or their salts of a polyadduct of 4 to 40mol of ethylene oxide with 1mol of phenol, or phosphates of the adducts of 6 to 30mol of ethylene oxide with 1mol of 4-nonylphenol, Imol of dinonylphenol or, in particular, with 1mol of compounds which are prepared by addition of 1 to 3mol of unsubstituted or substituted styrenes to 1mol of phenol, polystyrene sulfonates, fatty acid taurides, alkylated diphenyl oxide monosulfonates or diphenyl oxide disulfonates, sulfonates of polycarboxylates, addition products of 1 to 60, preferably of 2 to 30mol, of ethylene oxide and/or propylene oxide with fatty amines, fatty amides, fatty acids or fatty alcohols containing 8 to 22 carbon atoms each or with tri- to hexa-valent alkanols containing 3 to 6 carbon atoms, which addition products have been converted to an acid ester with an organic dicarboxylic acid or an inorganic polyacid, S lignin sulfonates and, in particular, formaldehyde condensates, for example condensates of lignin sulfonates and/or phenol S 25 and formaldehyde, condensates of formaldehyde with aromatic sulfonic acids, for example condensates of ditolyl ether sulfonates and formaldehyde, condensates of naphthalene sulfonic acid and/or naphthol- or naphthylaminosulfonic acids with formaldehyde, condensates of phenolsulfonic acids and/or sulfonated dihydroxydiphenylsulfone and phenols or cresols with formaldehyde and/or urea, and also condensates of diphenyl oxide disulfonic acid derivatives with formaldehyde.
Polyester fibre materials which can be dyed or printed and which are treated with the compounds of formula will be understood as being, for example, cellulose ester fibres, such as cellulose-24-acetate fibres and cellulose-24-triacetate fibres and, in particular, linear polyester fibres which are possibly also acid-modified, which are obtained, for example, by condensation of terephthalic acid with ethylene glycol or of isophthalic or terephthalic acid with 1,4bis(hydroxymethyl)cyclohexane, and also fibres of copolymers of terephthalic and isophthalic acid and ethylene glycol. The linear polyester fibre material (PES) which is as yet almost exclusively used in the industry consists of terephthalic acid and ethylene glycol.
N\C:04546 The fibre materials can also be used as blends with each other or with other fibres, for example blends of polyacrylonitrile/polyester, polyamide/polyester, polyester/cotton, polyester/viscose and polyester/wool, and can be dyed or also printed by known batchwise or continuous processes.
The polyester fibre material can be in different forms of presentation. Suitable materials are usefully piece goods, such as knitgoods, bonded fibre fabrics or wovens, or also yarn on cheeses, warp beams, and the like.
Particularly suitable for the novel process are polyester textile fabrics and textile blends comprising polyester fibres which are used for the automotive sector.
Also very suitable for the novel process are polyester textile fabrics and textile blends lo comprising polyester fibres used for the outerwear garment sector, which are transparent. If such textiles are treated by the novel process they can protect the skin tissue underneath the transparent outerwear garment fabric from the harmful effect of UV radiation.
If the novel compound of formula is used in the dyeing application, then application is carried our, for example, by treating the fibre material first with this compound and dyeing it, or, 15 preferably, by treating the fibre material simultaneously with a compound of formula and the dye in the dye bath. However, it is also possible to apply the compound of formula later to the finished dyeing and fixing it by thermofixation, eg. at temperatures from 190 to 230°C, over 30 seconds to S• minutes.
Simultaneous application of the compound of formula with a dye in the dye bath is preferred.
20 Dyes suitable for dyeing or printing polyester fibre materials are disperse dyes which are only sparingly soluble in water.
These dyes are, for example, those described in Colour Index, 3rd edition (3 rd revision 1987 inclusive Additions and Amendments up to No. 85) under "Disperse Dyes".
The disperse dyes in the dye liquor are mainly present in the form of a fine dispersion. They may be part of different dye classes, for example of the amino, aminoketone, acridone, coumarine, ketoninime, methine, perinone, naphthoquinonimino, nitro, polymethine, diphenylamino, quinoline, benzimidazole, xanthene, oxazine, quinophthalone, styryl and, in particular, anthraquinone and azo dyes, for example mono- or disazo dyes. It is also possible to use mixtures of disperse dyes.
In addition to the dyes and the compounds of formula the dye baths can also contain further additives, such as dyeing auxiliaries, dispersants, carriers, wool protecting and wetting agents as well as antifoams.
The dye baths can also contain mineral acids, for example sulfuric acid or phosphoric acid, or usefully organic acids, for example aliphatic carboxylic acids, such as formic acid, acetic acid, oxalic acid or citric acid and/or salts, eg. ammonium acetate, ammonium sulfate or sodium acetate. The acids serve principally to adjust the pH of the liquors used according to this invention, which is preferably from 4 to Dyeing is carried out from an aqueous liquor by a continuous or batchwise process. In the batchwise process (exhaust process) the liquor ratio can be chosen within a wide range, eg. from 1:4 to 1:100, preferably from 1:6 to 1:50. The dyeing temperature is at least 50 0 C and is usually not above 140°C. The preferred dyeing temperature is in the range from 80 to 1350C.
N\C:04546 4 In continuous dyeing processes, the dye liquors are applied to the piece goods eg. by paddyeing or slop-padding and are developed by thermofixation or HT-steam processes.
Linear polyester fibres and cellulose fibres are preferably dyed by the so-called hightemperature method in closed and pressure-resistant apparatus at temperatures of >1000C, preferably in the range from 110° to 135°C and, if appropriate, under pressure. Suitable closed vessels are, for example, circulation apparatus, such as cheese dyeing or beam dyeing apparatus, winch becks, jet dyeing or drum dyeing machines, muff dyeing apparatus, paddles or jiggers.
Cellulose-24-acetate fibres are preferably dyed at temperatures from 80-85 0
C.
The fibre material is preferably run in the bath for 5 minutes at 40 to 80 0 C, which bath comprises the dye, the UV absorber and, where appropriate, further additives and which is adjusted to a pH of 4.5 to 5.5, and the temperature is then raised over 10 to 20 minutes to 125 to 130°C and the fibre material is further treated for 15 to 90 minutes, preferably for 30 minutes, at this temperature.
The dyeings are finished by cooling the dye liquor to 50 to 800C, rinsing the dyeings with water and, if desired, purifying them in customary manner in alkaline medium under reductive conditions.
15 The dyeings are then rinsed again and dried.
If the compound of formula is applied before or after dyeing from a separate treatment liquor to the polyester fibre material, then this is also done by a continuous or batchwise process. In the batchwise process (exhaust process) the liquor ratio can be chosen from a wide range, eg. from 1:4 to 1:100, preferably from 1:6 to 1:50.
20 In the continuous process, the treatment liquor is applied to the piece goods for example by padding or slop-padding and fixed by means of thermofixation or HT steaming processes.
To produce prints, the compounds of formula used according to this invention are conveniently added in the form of their aqueous dispersions to the printing pastes.
The printing paste in this case contains the corresponding compound of formula in amounts of 0.01 to 5% by weight, preferably of 0.1 to 3% by weight, based on the weight of the printing paste.
However, it is also possible to apply the compounds of formula already when preparing the material for printing, eg. by the thermofixation method.
The amount of the dyes which are added to the printing pastes depends on the desired shade; amounts of 0.01 to 15, preferably of 0.02 to 10% by weight, based on the textile material used, have generally been found to be useful.
In addition to the dyes and the aqueous UV absorber dispersion, the printing pastes usefully contain acid-stable thickeners, preferably of natural origin, such as plant seed gum derivatives, in particular sodium alginate, by themselves or in admixture with modified cellulose, in particular with preferably 20 to 25% by weight of carboxymethylcellulose. In addition, the printing pastes can also contain acid donors, such as butyrolactone or sodium hydrogen phosphate, preservatives, sequestrants, emulsifiers, water-insoluble solvents, oxidants or deaerators.
Suitable preservatives are in particular formaldehyde-donating agents, such as paraformaldehyde or trioxane, especially aqueous, about 30 to 40% by weight formaldehyde solutions; suitable sequestrants are eg. sodium nitrilotriacetic acid, sodium ethylenediaminetetracetic acid, especially sodium polymetaphosphate, in particular sodium hexametaphosphate; suitable N\C:04546 emulsifiers are especially adducts of alkylene oxide and fatty alcohol, in particular an adduct of oleyl alcohol and ethylene oxide; suitable water-insoluble solvents are high-boiling saturated hydrocarbons, especially paraffins having a boiling range of about 160 to 210°C (so-called white spirits); suitable oxidants are eg. an aromatic nitro compound, especially aromatic mono- or dinitrocarboxylic acid or mono- or dinitrosulfonic acid, which may be in the form of an alkylene oxide adduct, in particular a nitrobenzenesulfonic acid; and suitable deaerators are typically high-boiling solvents, especially turpentine oils, higher alcohols, preferably C8- to Cloalcohols, terpene alcohols or deaerators based on mineral and/or silicone oils, in particular commercial formulations consisting of about 15 to 25% by weight of a mixture of mineral and silicone oil and about 75 to 85% by weight of a Csalcohol such as 2-ethyl-n-hexanol.
When printing the fibre material, the printing paste is applied direct over the entire fibre material or only on parts thereof, convenient printing machines being those of conventional build, eg.
rotogravure, rotary screen printing, flat screen printing or ink jet machines.
1 After being printed, the fibre material is dried at a temperature of up to 150°C, preferably in the range from 80° to 120°C.
Fixation of the material is then carried out by heat treatment in the temperature range from preferably 1000 to 220°C. The heat treatment is usually carried out in superheated steam under S* pressure.
Depending on the temperature, the fixation can be carried out in 20 seconds to 12 minutes, S: 20 preferably in 4 to 8 minutes.
S* The prints are also finished in conventional manner by rinsing with water and, if appropriate, by additional purification in alkaline medium under reductive conditions eg. with sodium dithionite. In the latter case, the prints are rinsed again and are then removed from the water and dried.
se* With the novel process it is possible to obtain polyester dyeings and prints which are highly lightfast and resistant to sublimation. The novel process does not require a selective pre- or aftertreatment of the fibre materials.
This invention also relates to the use of the compounds of formula as agents for the photochemical and thermal stabilisation of dyeings and prints on polyester fibre materials and polyester fibre-containing fibre blends.
The following Examples illustrate the invention in more detail. Parts and percentages are by weight and temperatures are given in degrees Celsius. The relationship between parts by weight and parts by volume is the same as that between the gram and the cubic centimetre.
Example 1: A laboratory apparatus is charged with 22.86g of p-anisic acid, 75mL of dioxan, and 0.1mL of dimethylformamide.
Subsequently, 23.2g of thionyl chloride are added dropwise over 10 minutes and the temperature is raised to about 550C, at which temperature the reaction mixture is kept for 90 minutes.
Dioxan is then distilled off until a temperature of 1150C is reached. 10.28g of salicylamide are then added and the resultant melt is stirred for 75 minutes at 120°C. The reaction mixture is cooled to N\C:04546 a 9 6 about 100°C and, after adding 70mL of dioxan, is stirred until the temperature has dropped to The reaction mixture is then charged with 13g of benzamidine-chlorohydrate, 8.5g of sodium methylate, and 150mL of methyl alcohol and stirred for 30 minutes at 60-65°C. The resultant beige suspension is cooled, collected by suction filtration and washed with 175mL of methyl alcohol and 300mL of warm water at 45°C and is then dried under vacuum at 50-600C.
This gives 21 .4 g of a pale beige powder of the compound of formula 0 HO NON 0 CH(6) The following compounds can be prepared in analogy to the procedure of Example 1 by replacing p-anisic acid with the corresponding p-ethoxybenzoic acid, p-n-propoxybenzoic acid or p- 0 0 HO NON HO N 0 N N N CH3 10 isopropoxybenzoic acid: O CH 3 0 CH 3 0 HO N 0
N
"O CH 3 Example 2: In a laboratory apparatus, equipped with an agitator, 5 parts by weight of the compound of formula according to Example 1 are charged with 25 parts by weight of quartz beads and ground with parts by weight of a condensate from naphthalenesulfonic acid and formaldehyde as dispersant, which is dissolved in 15mL of water, at about 1600rpm until a particle size of less than 2im is obtained. The dispersion is then separated from the quartz beads. By adding water, the compound of formula content is adjusted to 10% by weight, based on the formulation.
A 10g piece of polyester tricot is dyed in a high-temperature dyeing apparatus (Turbomat®, of Mathis, Niederhasli, CH) at a liquor ratio of 1:10. The aqueous dye liquor contains per 1L of liquor 2g of ammonium sulfate, 0.5g of a commercially available levelling agent, 0.5g of the formulation prepared under of the compound of formula 0.83g of a dye mixture containing 0.28g of the dye H O H -Nf0 of formula o N\C:04546 7 0 00 o N -O CH 3 0.26g of a dye of formula H 0
CH
3 0 NH 0 O-CH 3 0 NH 2 0 0.16g of a dye of formulae 0 NH 2 0
NH
2 0 (9) 0 NH 2 0 NH 2 00 00 0 NS H' ,S and 0.13g of the dye of formulae
CH
3 The dye liquor is adjusted to pH5 with acetic acid and is then homogenised, placed into the 5 high-temperature dyeing apparatus together with the polyester tricot and heated first to 70°C and then over 30 minutes to 130°C. The polyester tricot is dyed for 60 minutes at this temperature.
The liquor is then cooled to 75°C and the dyed polyester tricot is rinsed with hot and cold water and subjected to reductive purification by treatment with a liquor containing 3mL/L of a 30% aqueous solution of NaOH and 2g/L of sodium dithionite for 20 minutes at 70°C. The polyester tricot piece is then rinsed with warm and cold water, centrifuged and dried at 800C.
SA grey polyester tricot is obtained having good allround fastness properties, in particular very good fastness to hot light.
N\C:04546

Claims (6)

1. A process for the photochemical stabilisation of dyeings and prints on polyester fibre materials, which comprises treating the polyester fibre materials with a compound of formula 0 HO N N R(1) wherein R 1 is Ci-C 4 alkyl.
2. A process according to claim 1, which comprises treating the polyester fibre materials with a compound of formula wherein Ri is ethyl or methyl. S. 3. A process according to claim 2, which comprises treating the polyester fibre materials with a compound of formula wherein R1 is methyl.
4. A process according to any one of claims 1 to 3, which comprises using 0.01 to 5% by weight, based on the weight of the fibre material, of a compound of formula A process for the photochemical stabilisation of dyeings and prints on polyester fibre Smaterials, said process being substantially as hereinbefore described with reference to any one of the examples. 15 6. Use of a compound of formula (1) 9 9 HO N N (1) wherein Ri is C1-C4alkyl for the photochemical and thermal stabilisation of dyeings and prints on polyester fibre materials and polyester fibre-containing fibre blends.
7. A process for the preparation of a compound of formula HO N N wherein R 1 is C1-C4alkyl, which comprises reacting an o-hydroxybenzamide of formula N\C:04546 r 9 OH O NH 2 o (2) 0 with a compound of formula R wherein R 1 has the meanings given for formula at a temperature in the range from 70 to 180°C 0 O QR 1 and then reacting the resultant intermediate of formula oR (4) rNH 5 with a compound of formula H 2 at a temperature from 50 to 800C.
8. A process according to claim 7, which comprises using a compound of formula wherein R 1 is ethyl or, preferably, methyl.
9. A process for the preparation of a 2-[4-(4-alkoxyphenyl)-6-phenyl[1,3,5]triazin-2-yl]- phenol, said process being substantially as hereinbefore described with reference to any one of the 10 examples. A 2-[4-(4-alkoxyphenyl)-6-phenyl[1,3,5]triazin-2-yl]-phenol prepared by the process of any one of claims 7 to 9. Dated 3 June 1999 CIBA SPECIALTY CHEMICALS HOLDING INC. C 6*SS Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON N\C:04546
AU34988/99A 1998-06-11 1999-06-10 Process for improving the photochemical and thermal stability of dyeings and prints on polyester fibre materials Abandoned AU3498899A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP98810533 1998-06-11
DE98810533 1998-06-11

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JP (1) JP2000054278A (en)
KR (1) KR20000006045A (en)
AU (1) AU3498899A (en)
BR (1) BR9902231A (en)
ID (1) ID23590A (en)
ZA (1) ZA993873B (en)

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JP4622083B2 (en) * 2000-10-24 2011-02-02 東レ株式会社 Method for printing aliphatic polyester fibers
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CN102219785B (en) * 2011-04-11 2014-04-02 山东大学 Triazine-containing benzoxazine, triazine-containing benzoxazine polymer, and preparation method thereof
BR112014010736B8 (en) * 2011-11-07 2023-05-16 Huntsman Adv Mat Switzerland METHODS FOR INCREASING THE CHLORINE TOLERANCE OF DRY SYNTHETIC POLYAMIDE FIBER MATERIALS AND FOR INCREASING THE DYE RESISTANCE OF DRY SYNTHETIC POLYAMIDE CARPET, PRODUCT AND THIOUREA/DIISOCYANATE ADDUCT
CN105332275B (en) * 2014-05-30 2019-07-12 东丽纤维研究所（中国）有限公司 A kind of para-aramid fiber
CN105439971A (en) * 2015-12-31 2016-03-30 华东师范大学 Synthetic method of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine
CN105541746A (en) * 2016-02-01 2016-05-04 太仓市茜泾化工有限公司 Preparation method of 2-(4-methoxyphenyl)-4H-benzo[e][1,3] oxazine-4-ketone
KR20210072041A (en) * 2018-10-03 2021-06-16 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 Novel Pyridine and Pyrimidine Substituted Triazine UV Absorbers

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KR20000006045A (en) 2000-01-25

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