EP0475905A1 - Procédé pour stabiliser photochimiquement la laine - Google Patents

Procédé pour stabiliser photochimiquement la laine Download PDF

Info

Publication number: EP0475905A1
Authority: EP; European Patent Office
Prior art keywords: formula; alkylamino; wool; phenyl; mono
Prior art date: 1990-09-13
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.): Granted

Application number

EP91810709A

Other languages

German (de)

English (en)

Other versions

EP0475905B1 (fr

Inventor

Manfred Dr. Rembold

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

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.)

1990-09-13

Filing date

1991-09-04

Publication date

1992-03-18

1991-09-04 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1992-03-18 Publication of EP0475905A1 publication Critical patent/EP0475905A1/fr

1998-01-14 Application granted granted Critical

1998-01-14 Publication of EP0475905B1 publication Critical patent/EP0475905B1/fr

2011-09-04 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

210000002268 wool Anatomy 0.000 title claims abstract description 29
238000000034 method Methods 0.000 title claims abstract description 28
230000006641 stabilisation Effects 0.000 title claims description 9
239000006096 absorbing agent Substances 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 7
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract description 6
239000007864 aqueous solution Substances 0.000 claims abstract 2
238000004043 dyeing Methods 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 21
239000000835 fiber Substances 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
-1 ammonium ions Chemical class 0.000 claims description 10
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
239000011591 potassium Substances 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
239000011734 sodium Substances 0.000 claims description 8
229910052708 sodium Inorganic materials 0.000 claims description 8
238000011105 stabilization Methods 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
QALAKUHQOSUJEU-UHFFFAOYSA-N calcium;magnesium Chemical compound [Mg+2].[Ca+2] QALAKUHQOSUJEU-UHFFFAOYSA-N 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000002657 fibrous material Substances 0.000 claims description 6
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
239000000080 wetting agent Substances 0.000 claims description 3
125000005208 trialkylammonium group Chemical group 0.000 claims 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
150000001768 cations Chemical class 0.000 abstract description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
238000004383 yellowing Methods 0.000 abstract 1
239000000975 dye Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000004744 fabric Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
239000004952 Polyamide Substances 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
235000015424 sodium Nutrition 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000010446 mirabilite Substances 0.000 description 2
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
125000005023 xylyl group Chemical group 0.000 description 2
ISCOWSBMWSYRMK-UHFFFAOYSA-N 2-hydroxy-3-[3-hydroxy-4-[4-[2-hydroxy-4-(2-hydroxy-3-sulfopropoxy)phenyl]-6-phenyl-1,3,5-triazin-2-yl]phenoxy]propane-1-sulfonic acid Chemical compound OC(COc1ccc(c(O)c1)-c1nc(nc(n1)-c1ccc(OCC(O)CS(O)(=O)=O)cc1O)-c1ccccc1)CS(O)(=O)=O ISCOWSBMWSYRMK-UHFFFAOYSA-N 0.000 description 1
XUHLFRSLFWCVBL-UHFFFAOYSA-N 3-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy]-2-hydroxypropane-1-sulfonic acid Chemical compound OC(COc1ccc(c(O)c1)-c1nc(nc(n1)-c1ccccc1)-c1ccccc1)CS(O)(=O)=O XUHLFRSLFWCVBL-UHFFFAOYSA-N 0.000 description 1
FYIXKWULFOCEQD-UHFFFAOYSA-N 3-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]-2-hydroxypropane-1-sulfonic acid Chemical compound Cc1ccc(c(C)c1)-c1nc(nc(n1)-c1ccc(OCC(O)CS(O)(=O)=O)cc1O)-c1ccc(C)cc1C FYIXKWULFOCEQD-UHFFFAOYSA-N 0.000 description 1
ZENQAFUZFAZRHD-UHFFFAOYSA-N 3-[4-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]-2-hydroxypropane-1-sulfonic acid Chemical compound Cc1ccc(cc1)-c1nc(nc(n1)-c1ccc(OCC(O)CS(O)(=O)=O)cc1O)-c1ccc(C)cc1 ZENQAFUZFAZRHD-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
HVXRCAWUNAOCTA-UHFFFAOYSA-N 4-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=C(O)C=C1 HVXRCAWUNAOCTA-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241001584775 Tunga penetrans Species 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
239000000980 acid dye Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
150000004700 cobalt complex Chemical class 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000009981 jet dyeing Methods 0.000 description 1
239000000434 metal complex dye Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
238000012856 packing Methods 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000010025 steaming Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000012749 thinning agent Substances 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1

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
- 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
- D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/628—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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- 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
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk

Definitions

the present invention relates to a process for the photochemical stabilization of wool or mixed fibers containing wool, an agent and a liquor for carrying out the process, and the fiber material treated with it.
the method according to the invention is characterized in that the wool or the mixed fiber containing wool is treated with an aqueous liquor which has at least one UV absorber of the formula contains wherein at least one of the substituents R1, R2 and R3 are a radical of the formula is what M hydrogen; Sodium; Potassium; Calcium; Magnesium; Ammonium; Mono-, di-, tri- or tretraalkylammonium; Mono-, di- or trihydroxyalkylammonium; or mixed with hydroxyalkyl and alkyl disubstituted or trisubstituted ammonium ions; m 1; or 2; and the or the other substituents independently of one another unsubstituted or substituted C1-C12 alkyl, C1-C12 alkoxy, C1-C12 alkylthio, mono-C1-C12 alkylamino or di-C1-C12 alkylamino; unsubstituted or phenyl, phenoxy, phen
substituents as an individual radical e.g. alkyl
compound radical e.g. alkoxyl
C1-C12 alkyl examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl or isomers of these radicals.
Particularly preferred alkyl radicals contain 1 to 4 carbon atoms.
alkyl radicals in the mono-, di-, tri- or treaalkylammonium ions are in particular independently of one another C1-C4-alkyl radicals, such as butyl, propyl, ethyl and preferably methyl.
Mono-, di- or trihydroxyalkylammonium are C1-C4-hydroxyalkylammonium cations which are derived in particular from ethanolamine, diethanolamine or triethanolamine.
the invention also includes mixed C1-C4-hydroxyalkyl-C1-C4-alkylamines, such as the cations derived from N-methyl-N-ethanolamine or N, N-dimethyl-N-ethanolamine.
Suitable substituents for the phenyl radicals are alkyl or alkoxy radicals having 1 to 12 carbon atoms, such as methyl, tert. Butyl, pentyl, octyl, nonyl, decyl, dodecyl, methoxy, butoxy or pentoxy, furthermore cyclopentyl, clyclohexyl and halogen in particular chlorine, in question.
the radicals R1, R2 and R3 can be further substituted.
C1-C4 alkoxyl such as methoxy or hydroxyl, phenyl or carbalkoxy having 2 to 9 carbon atoms, are the preferred substituents on the alkyl radicals of the C1-C12 alkyl, C1-C12 alkoxy, C1-C12 alkylthio, mono -C1-C12 alkylamino or di-C1-C12 alkylamino radicals.
the compounds of formula (1) include the potassium salt of such compounds in which R1 phenyl and R2 and R3 each represent the rest of the formula (2) or the sodium salt of the compound of formula (1), wherein R1 p-chlorophenyl and R2 and R3 each represent the rest of the formula (2) into consideration.
UV absorbers those of the formula correspond to what R4 and R5 independently of one another, C1-C12 alkyl; m 1 or 2; M hydrogen; Sodium; Potassium; Calcium; Magnesium; Ammonium or tetraalkylammonium; and n1 and n2 0; 1; or 2; means.
R1 is phenyl, tolyl or xylyl
R1 and R2 means phenyl, tolyl or xylyl
M is hydrogen, sodium or potassium, in particular hydrogen.
the compounds of formula (1) can be prepared in a manner known per se, e.g. according to the processes described in EP-A-0 165 608.
the amount of UV absorber to be added depends on the substrate and the desired stabilization. In general, 0.1 to 5, preferably 0.3 to 3% by weight, based on the wool, is added.
the process according to the invention also photochemically stabilizes the dyeings applied to the wool.
the dyeings to be stabilized according to the invention are in particular those which are formed by acid or metal complex dyes, e.g. 1: 2 chromium, 1: 2 cobalt complex dyes or Cu complex dyes are generated.
the amount of dye to be added can vary within wide limits, from 0.01 to 10% by weight, based on the wool, of dye. Quantities are preferred from 0.05 to 2% by weight.
the compounds of the formula (1) are applied from an aqueous bath.
the application can take place before, during or after dyeing, the dyeing and photochemical stabilization preferably being carried out in the same bath.
the coloring and photochemical stabilization are expediently carried out simultaneously.
UV absorber, dye and the chemicals usual for the dyeing process are added to the aqueous dyeing liquor.
Mineral acids such as e.g. Sulfuric acid or phosphoric acid, organic acids, expediently aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
the acids are used primarily to adjust the pH of the liquors used according to the invention, which can be varied within wide ranges; the pH is preferably between 3 and 8.
the dyeing liquors also contain commercially available dispersing and leveling agents and can furthermore contain auxiliaries customary in dyeing technology, such as electrolytes, wetting agents, defoamers, antifoams, thickeners or wool preservatives.
All continuous and discontinuous dyeing processes can be used with the usual dyeing machines, such as open baths, combed, strand yarn or packing machines, jiggers, paddle machines, tree dyeing machines, circulation or jet dyeing machines or reel runners for the treatment.
the process according to the invention expediently takes place in the exhaust process, normal pressure dyeing apparatus being used.
the liquor ratio can be selected within a wide range, e.g. 1: 5 to 1: 300, preferably 1:10 to 1:50. It is convenient to work at a temperature of 30 to 120 ° C, preferably 50 to 98 ° C.
the liquor application is expediently 30-400% by weight, preferably 75-250% by weight.
the fiber material is subjected to heat treatment to fix the applied dyes.
the fixation process can also be carried out using the cold dwell method.
the heat treatment is preferably carried out by a steaming process with treatment in a steamer with possibly superheated steam at a temperature of 98 to 105 ° C during e.g. 1 to 7, preferably 1 to 5 minutes.
the fixation of the dyes and the compounds of formula (1) according to the cold residence process can be carried out by storing the impregnated and preferably rolled-up goods at room temperature (15 to 30 ° C), e.g. during 3 to 24 hours, the cold residence time being known to depend on the type of dye applied.
the duration of treatment depends on the duration of dyeing, which is within the usual range and is usually 20 to 120 minutes. If the UV absorber is added before or after the dyeing stage, the treatment time is 15 to 60 minutes.
the dyeings produced are rinsed and dried in the customary manner.
Wool can be considered as the fiber material that can be dyed according to the invention.
the wool can be finished normally or without felt.
fiber blends made of wool and synthetic polyamide or wool / polyester blends can also be used, e.g. Jersey material made of wool / polyamide in a mixing ratio of 70:30.
the pure or mixed fiber material can be in various processing forms, such as as fiber, yarn, fabric, knitted fabric, fleece or pile material.
the present method is particularly advantageous for the treatment of fiber material which is exposed to light and heat and is used, for example, as a car upholstery material or carpet.
the UV absorbers used according to the invention can be used in a wide pH range, which means that they are also suitable for application Mixtures of wool with other fibers, such as wool and polyamide, are suitable.
the present invention furthermore relates to an agent for carrying out the process according to the invention, which is characterized in that it contains at least one UV absorber of the formulas (1) or (3), the meaning of which is as defined above, in addition to the customary formulation auxiliaries such as wetting and thinning agents.
Example 1 4 samples of 10 g each of a wool sergeant fabric are dyed at a liquor ratio of 1:25 in an open dyeing machine, for example an AHIBA®. Four fleets are prepared for this, which contain the following additives:
Fleet 3 (model 3): This fleet corresponds to fleet 1 with the difference that it additionally 1% of the compound of the formula contains.
Fleet 5 (model 5): This fleet corresponds to fleet 1 with the difference that it additionally 1% of the compound of the formula contains.
Fleet 6 (sample 6): This fleet corresponds to fleet 2 with the difference that no dye is used (blind dyeing with UV absorber).
Fleet 7 (pattern 7): This fleet corresponds to fleet 1 with the difference that no dye is used (blind dyeing without UV absorber). If necessary, the pH is adjusted to 4.5 with 10% acetic acid.
Table 1 shows the light fastness according to the gray scale and the colorimetric evaluations according to DIN 6174 (Cielab formula).
Example 2 2 samples of 10 g each of a wool sergeant fabric are dyed at a liquor ratio of 1:25 in an open dyeing machine, for example an ® AHIBA.
Two fleets are prepared, which contain the following additives: Fleet 1 (sample 1): 6% ammonium sulfate 5% Glauber's salt 1 g / l sodium acetate 1% of an anionic leveling agent based on an alkylaminopolyglycol ether 0.01% of the dye of the formula and 0.01% of the dye of the formula

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Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Coloring (AREA)

EP91810709A 1990-09-13 1991-09-04 Stabilisation photochimique de la laine Expired - Lifetime EP0475905B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH297390		1990-09-13
CH2973/90		1990-09-13

Publications (2)

Publication Number	Publication Date
EP0475905A1 true EP0475905A1 (fr)	1992-03-18
EP0475905B1 EP0475905B1 (fr)	1998-01-14

Family

ID=4245798

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP91810709A Expired - Lifetime EP0475905B1 (fr)	1990-09-13	1991-09-04	Stabilisation photochimique de la laine

Country Status (6)

Country	Link
US (1)	US5197991A (fr)
EP (1)	EP0475905B1 (fr)
JP (1)	JP3184259B2 (fr)
AU (1)	AU8387591A (fr)
DE (1)	DE59108923D1 (fr)
NZ (1)	NZ239755A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
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EP2175059A1 (fr) *	2008-10-07	2010-04-14	Fabryka Dywanow Agnella S.A.	Fil de laine

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US5298030A (en) *	1992-02-21	1994-03-29	Ciba-Geigy Corporation	Process for the photochemical and thermal stabilization of undyed and dyed or printed polyester fiber materials
US5773182A (en)	1993-08-05	1998-06-30	Kimberly-Clark Worldwide, Inc.	Method of light stabilizing a colorant
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US5681380A (en)	1995-06-05	1997-10-28	Kimberly-Clark Worldwide, Inc.	Ink for ink jet printers
US5700850A (en)	1993-08-05	1997-12-23	Kimberly-Clark Worldwide	Colorant compositions and colorant stabilizers
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US5645964A (en)	1993-08-05	1997-07-08	Kimberly-Clark Corporation	Digital information recording media and method of using same
US6211383B1 (en)	1993-08-05	2001-04-03	Kimberly-Clark Worldwide, Inc.	Nohr-McDonald elimination reaction
US5721287A (en)	1993-08-05	1998-02-24	Kimberly-Clark Worldwide, Inc.	Method of mutating a colorant by irradiation
US6017471A (en)	1993-08-05	2000-01-25	Kimberly-Clark Worldwide, Inc.	Colorants and colorant modifiers
US5733693A (en)	1993-08-05	1998-03-31	Kimberly-Clark Worldwide, Inc.	Method for improving the readability of data processing forms
GB9326358D0 (en)	1993-12-23	1994-02-23	Ciba Geigy Ag	Compositions for the treatment of textiles
US6071979A (en)	1994-06-30	2000-06-06	Kimberly-Clark Worldwide, Inc.	Photoreactor composition method of generating a reactive species and applications therefor
US6242057B1 (en)	1994-06-30	2001-06-05	Kimberly-Clark Worldwide, Inc.	Photoreactor composition and applications therefor
US5685754A (en)	1994-06-30	1997-11-11	Kimberly-Clark Corporation	Method of generating a reactive species and polymer coating applications therefor
GB2291658B (en)	1994-07-23	1998-08-12	Ciba Geigy Ag	Aqueous textile treatment compositions containing an ultra-violet absorbing agent
US6008268A (en)	1994-10-21	1999-12-28	Kimberly-Clark Worldwide, Inc.	Photoreactor composition, method of generating a reactive species, and applications therefor
TW290606B (fr) *	1995-03-17	1996-11-11	Ciba Geigy Ag
US5837429A (en)	1995-06-05	1998-11-17	Kimberly-Clark Worldwide	Pre-dyes, pre-dye compositions, and methods of developing a color
US5786132A (en)	1995-06-05	1998-07-28	Kimberly-Clark Corporation	Pre-dyes, mutable dye compositions, and methods of developing a color
AU5535296A (en)	1995-06-28	1997-01-30	Kimberly-Clark Worldwide, Inc.	Novel colorants and colorant modifiers
US5782963A (en)	1996-03-29	1998-07-21	Kimberly-Clark Worldwide, Inc.	Colorant stabilizers
US6099628A (en)	1996-03-29	2000-08-08	Kimberly-Clark Worldwide, Inc.	Colorant stabilizers
PL321573A1 (en)	1995-11-28	1997-12-08	Kimberly Clark Co	Improved stabilising agents for dyes
US5855655A (en)	1996-03-29	1999-01-05	Kimberly-Clark Worldwide, Inc.	Colorant stabilizers
US5891229A (en)	1996-03-29	1999-04-06	Kimberly-Clark Worldwide, Inc.	Colorant stabilizers
GB2313850A (en) *	1996-06-04	1997-12-10	Ciba Geigy Ag	Triazine based UVA compounds as quenchers in paper making processes
GB9611614D0 (en) *	1996-06-04	1996-08-07	Ciba Geigy Ag	Process for inhibiting the effect of flourescent whitening agents
US6524379B2 (en)	1997-08-15	2003-02-25	Kimberly-Clark Worldwide, Inc.	Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
AU4320799A (en)	1998-06-03	1999-12-20	Kimberly-Clark Worldwide, Inc.	Neonanoplasts and microemulsion technology for inks and ink jet printing
SK1552000A3 (en)	1998-06-03	2000-08-14	Kimberly Clark Co	Novel photoinitiators and applications therefor
US6228157B1 (en)	1998-07-20	2001-05-08	Ronald S. Nohr	Ink jet ink compositions
CA2353685A1 (fr)	1998-09-28	2000-04-06	Kimberly-Clark Worldwide, Inc.	Nouveaux photoamorceurs et leurs utilisations
WO2000042110A1 (fr)	1999-01-19	2000-07-20	Kimberly-Clark Worldwide, Inc.	Nouveaux colorants,stabilisateurs de colorants, compositions d'encre, et leur procedes de preparation ameliores
US6331056B1 (en)	1999-02-25	2001-12-18	Kimberly-Clark Worldwide, Inc.	Printing apparatus and applications therefor
US6294698B1 (en)	1999-04-16	2001-09-25	Kimberly-Clark Worldwide, Inc.	Photoinitiators and applications therefor
US6368395B1 (en)	1999-05-24	2002-04-09	Kimberly-Clark Worldwide, Inc.	Subphthalocyanine colorants, ink compositions, and method of making the same
US7824566B2 (en) *	2003-07-08	2010-11-02	Scheidler Karl J	Methods and compositions for improving light-fade resistance and soil repellency of textiles and leathers
CA2530759C (fr) *	2003-07-08	2012-02-21	Karl J. Scheidler	Procedes et compositions ameliorant la resistance a la lumiere et la resistance aux salissures des textiles et des cuirs

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US3444164A (en) *	1965-09-24	1969-05-13	Ciba Ltd	Hydroxyphenyl-1,3,5-triazines containing sulfonic acid groups and their preparation
EP0165608A2 (fr) *	1984-06-22	1985-12-27	Ilford Ag	Hydroxyphényltriazines, procédé pour leur préparation et leur utilisation comme absorbant d'UV
EP0245204A1 (fr) *	1986-05-05	1987-11-11	Ciba-Geigy Ag	Procédé de stabilisation photochimique de matière fibreuse en polyamide teinté ou non teinté et ses mélanges avec d'autres fibres
EP0310083A1 (fr) *	1987-10-02	1989-04-05	Ciba-Geigy Ag	Procédé pour éteindre ou supprimer la fluorescence de substrats soumis à un azurage optique

1991
- 1991-09-04 DE DE59108923T patent/DE59108923D1/de not_active Expired - Fee Related
- 1991-09-04 EP EP91810709A patent/EP0475905B1/fr not_active Expired - Lifetime
- 1991-09-06 US US07/755,714 patent/US5197991A/en not_active Expired - Fee Related
- 1991-09-11 NZ NZ239755A patent/NZ239755A/xx unknown
- 1991-09-12 AU AU83875/91A patent/AU8387591A/en not_active Abandoned
- 1991-09-13 JP JP23436791A patent/JP3184259B2/ja not_active Expired - Fee Related

Patent Citations (4)

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Publication number	Priority date	Publication date	Assignee	Title
US3444164A (en) *	1965-09-24	1969-05-13	Ciba Ltd	Hydroxyphenyl-1,3,5-triazines containing sulfonic acid groups and their preparation
EP0165608A2 (fr) *	1984-06-22	1985-12-27	Ilford Ag	Hydroxyphényltriazines, procédé pour leur préparation et leur utilisation comme absorbant d'UV
EP0245204A1 (fr) *	1986-05-05	1987-11-11	Ciba-Geigy Ag	Procédé de stabilisation photochimique de matière fibreuse en polyamide teinté ou non teinté et ses mélanges avec d'autres fibres
EP0310083A1 (fr) *	1987-10-02	1989-04-05	Ciba-Geigy Ag	Procédé pour éteindre ou supprimer la fluorescence de substrats soumis à un azurage optique

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2175059A1 (fr) *	2008-10-07	2010-04-14	Fabryka Dywanow Agnella S.A.	Fil de laine

Also Published As

Publication number	Publication date
NZ239755A (en)	1993-05-26
JPH04281070A (ja)	1992-10-06
DE59108923D1 (de)	1998-02-19
JP3184259B2 (ja)	2001-07-09
AU8387591A (en)	1992-03-19
US5197991A (en)	1993-03-30
EP0475905B1 (fr)	1998-01-14

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Date	Code	Title	Description
1992-01-31	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
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1994-03-23	17Q	First examination report despatched	Effective date: 19940203
1996-12-18	RAP1	Party data changed (applicant data changed or rights of an application transferred)	Owner name: CIBA SC HOLDING AG
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1997-03-12	RAP3	Party data changed (applicant data changed or rights of an application transferred)	Owner name: CIBA SPECIALTY CHEMICALS HOLDING INC.
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Publication	Publication Date	Title
JP3184259B2 (ja)	2001-07-09	ウールの光化学安定化法
EP0200843B1 (fr)	1988-06-22	Procédé de stabilisation photochimique de matière fibreuse en polyamide teinté ou non teinté et ses mélanges
EP0459950B1 (fr)	1997-03-12	Stabilisation de teintures sur des fibres en polyamides
EP0345212A1 (fr)	1989-12-06	Procédé pour empêcher le jaunissement de matériaux fibreux en polyamide ennoblis au moyen d'agents antisalissures
EP0417040A1 (fr)	1991-03-13	Procédé pour teindre la laine
EP0255481A1 (fr)	1988-02-03	Procédé de stabilisation photochimique de matière fibreuse en polyamide et ses mélanges avec d'autres fibres
DE2726433A1 (de)	1977-12-29	Verfahren zur verbesserung der farbausbeute und der echtheiten von mit anionischen farbstoffen auf cellulosefasermaterial erzeugten faerbungen, kationische faserreaktive verbindungen und ihre herstellung
DE2834997B1 (de)	1980-01-03	Verfahren zum Faerben von synthetischen Polyamidfasern mit Reaktivfarbstoffen nach der Ausziehmethode
CH689479B5 (de)	1999-11-15	Verbindungen der s-Triazinreihe.
EP0584044A1 (fr)	1994-02-23	Procédé de stabilisation photochimique et thermique de matériaux fibreux teints et non-teints en polyester
EP0657577A1 (fr)	1995-06-14	Procédé de stabilisation photochimique et thermique de matériaux fibreux polyesters teints, non-teints ou imprimés
EP0302013A1 (fr)	1989-02-01	Procédé de teinture de produits textiles en polyamide
DE1099494B (de)	1961-02-16	Verfahren zur Fertigstellung von Faerbungen, welche in saurem Bade auf stickstoffhaltigen Fasern mit im Bad loeslichen Farbstoffen, die mindestens ein bewegliches, mit den Fasern reaktionsfaehiges Halogenatom enthalten, hergestellt worden sind
EP0950751B1 (fr)	2004-10-13	Procédé de traitement de fibres de cellulose
DE2653284B2 (de)	1978-09-07	Verfahren zum gleichmäßigen Farben von synthetischen Fasermaterialien
EP0474594B1 (fr)	1997-03-12	Procédé de teinture de la laine et ses mélanges avec d'autres fibres avec des colorants réactifs
EP0621266A1 (fr)	1994-10-26	Phénols à empêchement stérique et leur utilisation pour la stabilisation des fibres polyamides
EP0735181A2 (fr)	1996-10-02	Teinture de matériaux fibreux de polyamide en présence de composés du manganèse pour donner des effets multicolores
DE2148867C3 (de)	1974-09-05	Verfahren zur kontinuierlichen Fixierung von Dispersionsfarbstoffen auf Polyester, Cellulosetriacetat, Cellulose-2 l/2-acetat und deren Mischungen
EP0890671A2 (fr)	1999-01-13	Utilisation d'amines grasses modifiées pour éviter le dépÔt de sous produits de bas poids moléculaire sur les matières textiles
DE1909518C3 (de)	1974-08-29	Verfahren zum einbadigen Färben von Mischungen aus Polyester- und Cellulosefaser
EP0950750B1 (fr)	2003-10-22	Procédé de traitement de fibres de cellulose
AT210382B (de)	1960-07-25	Verfahren zum Fertigstellen von Färbungen
AT226190B (de)	1963-03-11	Verfahren zum Färben von stickstoffhaltigen Fasern mit sulfonsäuregruppenhaltigen Kupferphthalocyaninen und Mittel zur Durchführung des Verfahrens
DE2521106C3 (de)	1977-01-27	Verfahren zum Färben von synthetische Fasern enthaltenden Materialien

EP0475905A1 - Procédé pour stabiliser photochimiquement la laine - Google Patents

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ID=4245798

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