DE3925259A1 - DRY PREPARATION OF LIGHT fastness improvers - Google Patents
DRY PREPARATION OF LIGHT fastness improversInfo
- Publication number
- DE3925259A1 DE3925259A1 DE3925259A DE3925259A DE3925259A1 DE 3925259 A1 DE3925259 A1 DE 3925259A1 DE 3925259 A DE3925259 A DE 3925259A DE 3925259 A DE3925259 A DE 3925259A DE 3925259 A1 DE3925259 A1 DE 3925259A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dry preparation
- complexing agent
- dry
- preparation according
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000008139 complexing agent Substances 0.000 claims abstract description 8
- 239000002270 dispersing agent Substances 0.000 claims abstract description 6
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- IHIZFBWFXODXJS-UHFFFAOYSA-N n-tert-butyl-2-[4-[(5,5-dioxo-2-phenyl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-yl)amino]phenyl]acetamide Chemical compound C1=CC(CC(=O)NC(C)(C)C)=CC=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1S(=O)(=O)CCC2 IHIZFBWFXODXJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 abstract description 5
- 229920002647 polyamide Polymers 0.000 abstract description 5
- 230000006641 stabilisation Effects 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 229920001732 Lignosulfonate Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000029087 digestion Effects 0.000 description 5
- 239000001488 sodium phosphate Substances 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 235000019256 formaldehyde Nutrition 0.000 description 4
- 229960004279 formaldehyde Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- -1 aromatic sulfonic acids Chemical class 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000009837 dry grinding Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000434 metal complex dye Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- FDLFMPKQBNPIER-UHFFFAOYSA-N 1-methyl-3-(3-methylphenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=C(C)C=CC=2)=C1 FDLFMPKQBNPIER-UHFFFAOYSA-N 0.000 description 1
- MFSJUURIAOOSJR-UHFFFAOYSA-N 2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)benzoic acid Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(C(O)=O)=C1 MFSJUURIAOOSJR-UHFFFAOYSA-N 0.000 description 1
- UXMQLRNDJOZAPS-UHFFFAOYSA-N 2-hydroxy-5-methylbenzoic acid Chemical compound CC1=CC=C(O)C(C(O)=O)=C1.CC1=CC=C(O)C(C(O)=O)=C1 UXMQLRNDJOZAPS-UHFFFAOYSA-N 0.000 description 1
- HLOISCHRUFNEBE-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound OC1=C(C2=CC=CC=C2C=C1)C(=O)O.OC1=C(C2=CC=CC=C2C=C1)C(=O)O HLOISCHRUFNEBE-UHFFFAOYSA-N 0.000 description 1
- UJYZTZFCXKRHCX-UHFFFAOYSA-N 4-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC1=C(C=C(C(=O)O)C=C1)C(=O)O.OC1=C(C=C(C(=O)O)C=C1)C(=O)O UJYZTZFCXKRHCX-UHFFFAOYSA-N 0.000 description 1
- FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 description 1
- NKBASRXWGAGQDP-UHFFFAOYSA-N 5-chlorosalicylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1O NKBASRXWGAGQDP-UHFFFAOYSA-N 0.000 description 1
- XAICWTLLSRXZPB-UHFFFAOYSA-N 5-tert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC=C(O)C(C(O)=O)=C1 XAICWTLLSRXZPB-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012506 Sephacryl® Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OVFCVRIJCCDFNQ-UHFFFAOYSA-N carbonic acid;copper Chemical compound [Cu].OC(O)=O OVFCVRIJCCDFNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000011646 cupric carbonate Substances 0.000 description 1
- 235000019854 cupric carbonate Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6423—Compounds containing azide or oxime groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/41—Phenol-aldehyde or phenol-ketone resins
-
- 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
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
Gegenstand der Erfindung sind Trockenpräparationen von Mitteln zur Verbesserung der Lichtechtheit von gefärbten Textilmaterialien, insbesondere Polyamidfasermate rialien.The invention relates to dry preparations of Means to improve the light fastness of colored Textile materials, especially polyamide fiber mate rialien.
Die Präparationen sind dadurch gekennzeichnet, daß sieThe preparations are characterized in that they
- A) einen phenolischen Komplexbildner,A) a phenolic complexing agent,
- B) ein komplexierbares Kupfer-II-Salz undB) a complexable copper (II) salt and
- C) ein DispergiermittelC) a dispersant
enthalten.contain.
Geeignete Komplexbildner A sind solche der Formel (I)Suitable complexing agents A are those of the formula (I)
worin - unabhängig voneinander -
Y =N-W, =N-Ar, =N-N-CH-Ar, =N-OH, =N-Ar-N=CH-Ar,
-N-AK-N=CH-Ar oder Sauerstoff,
R H, OH, W oder OW und
X₁-X₄ H, W, OH, Halogen, CN, NH₂, NVW, SO₃H, COOH,
COOW, CONVW oder CONH₂ bedeuten und zwei benachbarte
Reste
X₁-X₄ auch gemeinsam die restlichen Glieder eines
ankondensierten Benzolringes bilden können,
wobei
AK für C₂-C₄-Alkylen,
Ar für Aryl bzw. Arylen,
W für C₁-C₁₈-Alkyl oder Cyclohexyl und
V für W oder H stehen,
wobei auch die entsprechenden Alkali- oder
Ammoniumsalze verwendet werden können.
in which - independently of one another -
Y = NW, = N-Ar, = NN-CH-Ar, = N-OH, = N-Ar-N = CH-Ar, -N-AK-N = CH-Ar or oxygen,
RH, OH, W or OW and
X₁-X₄ H, W, OH, halogen, CN, NH₂, NVW, SO₃H, COOH, COOW, CONVW or CONH₂ mean and two adjacent radicals
X₁-X₄ can also together form the remaining members of a condensed benzene ring,
in which
AK for C₂-C₄ alkylene,
Ar for aryl or arylene,
W for C₁-C₁₈ alkyl or cyclohexyl and
V stands for W or H,
the corresponding alkali or ammonium salts can also be used.
"Halogen" steht vorzugsweise für Cl. Beispiele für ge eignete Reste Ar sind vor allem Phenyl- bzw. Phenylen reste, die durch X₁-X₄ substituiert sein können."Halogen" preferably stands for Cl. Examples of ge suitable Ar radicals are especially phenyl or phenylene residues that can be substituted by X₁-X₄.
Bevorzugte Verbindungen A sind solche der FormelnPreferred compounds A are those of the formulas
Vorzugsweise stehen X₁-X₄ für Cl, C₁-C₄-Alkyl, Methoxy und insbesondere für Wasserstoff. Beispiele der erfindungsgemäß zu verwendenden Verbindungen (VIII) sindX₁-X₄ are preferably Cl, C₁-C₄-alkyl, methoxy and especially for hydrogen. Examples of Compounds (VIII) to be used according to the invention are
- a) Salicylsäurea) Salicylic acid
- b) 5-Methylsalicylsäure (p-Kresotinsäure)b) 5-methylsalicylic acid (p-cresotinic acid)
- c) 5-tert.-Butylsalicylsäurec) 5-tert-butylsalicylic acid
- d) 5-Chlorsalicylsäure d) 5-chlorosalicylic acid
- e) 5-tert.-Octylsalicylsäuree) 5-tert-octylsalicylic acid
- f) 2,4-Dihydroxybenzoesäure (β-Resourcylsäure)f) 2,4-dihydroxybenzoic acid (β-resourcylic acid)
- g) 2-Hydroxynaphthalin-1-carbonsäure (2-Hydroxy-1- naphthoesäure)g) 2-hydroxynaphthalene-1-carboxylic acid (2-hydroxy-1- naphthoic acid)
- h) 4-Hydroxy-1,3-benzoldicarbonsäure (4-Hydroxy isophthalsäure)h) 4-hydroxy-1,3-benzenedicarboxylic acid (4-hydroxy isophthalic acid)
- i) Salicylaldehydi) salicylaldehyde
- j) 5-Chlorsalicylaldehydj) 5-chlorosalicylaldehyde
- k) 3-Methoxysalicylaldehyd.k) 3-methoxysalicylaldehyde.
Vorgenannte Komplexbildner können auch in beliebiger Mischung untereinander verwendet werden.The aforementioned complexing agents can also be used in any Mixture can be used with each other.
Geeignete Kupfer-II-Salze B sind z. B. CuCl₂, CuSO₄ · 5 H₂O, Cu(OAc)₂ · H₂O oder CuCO₃ · Cu(OH)₂.Suitable copper (II) salts B are e.g. B. CuCl₂, CuSO₄.5 H₂O, Cu (OAc) ₂ · H₂O or CuCO₃ · Cu (OH) ₂.
Geeignete Dispergiermittel C sind:Suitable dispersants C are:
- a) Ligninsulfonate mit einem Schwefelgehalt von 4-6 Gew.-% und einer mittleren Molmasse von 1500 g mol-1 (Typ I),a) lignin sulfonates with a sulfur content of 4-6% by weight and an average molecular weight of 1500 g mol -1 (type I),
- b) Ligninsulfonate mit einem Schwefelgehalt von mindestens 6 Gew.-% und einer mittleren Molmasse von 6500 g mol-1 (Typ II) undb) lignin sulfonates with a sulfur content of at least 6% by weight and an average molecular weight of 6500 g mol -1 (type II) and
- c) salzarme Kondensationsprodukte von cycloaliphatischen oder aromatischen Sulfonsäuren und Formal dehyd (Typ III),c) low salt condensation products of cycloaliphatic or aromatic sulfonic acids and formal dehyde (type III),
wobei die Molmassen mit Hilfe eines wäßrigen Gelpermea tionsverfahrens bestimmt werden, in welchem die Molmassen verteilungen über ein Trenngel SEPHACRYL S 300 re fraktometrisch aufgenommen und mit Hilfe einer Eichung in 0,9%iger NaCl-Lösung bekannten Dextranmolmassen zu geordnet werden.the molecular weights using an aqueous gel permeate tion process are determined in which the molecular weights distributions via a separating gel SEPHACRYL S 300 re recorded fractometrically and with the help of a calibration Known dextran molar masses in 0.9% NaCl solution be ordered.
Geeignete Dispergiermittel I und II sind handelsübliche Produkte, die durch Sulfit- oder Kraftaufschluß des Holzes gewonnen werden.Suitable dispersants I and II are commercially available Products by sulfite or force digestion of the Wood.
Geeignete Dispergiermittel vom Typ III sind vor allem die Alkali- und Ammoniumsalze von Kondensationsprodukten aromatischer Sulfonsäuren mit Formaldehyd, wie z. B. Formaldehyd-Kondensationsprodukte aus (Alkyl)-Naphtha linsulfonsäuren, Mischungen von Naphthalin- und Benzol sulfonsäuren, Mischungen von Kresolen und Naphthalinsul fonsäuren, sulfierten Diphenylethern, sulfierten Di phenylthioethern, sulfierten Diphenylsulfonen sowie von Mischungen von Cycloalkanonen und Alkalibisulfit.Suitable type III dispersants are above all the alkali and ammonium salts of condensation products aromatic sulfonic acids with formaldehyde, such as. B. Formaldehyde condensation products from (alkyl) naphtha linsulfonic acids, mixtures of naphthalene and benzene sulfonic acids, mixtures of cresols and naphthalenesul fonic acids, sulfated diphenyl ethers, sulfated di phenylthioethers, sulfated diphenyl sulfones and from Mixtures of cycloalkanones and alkali bisulfite.
Solche Produkte, die vorzugsweise in elektrolytarmer Form eingesetzt werden, sind vielfach in der Literatur beschrieben, vergl. z. B. US-A 23 15 951, GB-A 7 15 919, DE-A 24 42 514, DE-A 25 42 090, DE-A 28 56 222.Such products, preferably in low-electrolyte Form used are widely in the literature described, see e.g. B. US-A 23 15 951, GB-A 7 15 919, DE-A 24 42 514, DE-A 25 42 090, DE-A 28 56 222.
Die Herstellung der neuen Trockenpräparationen kann auf verschiedene Weise erfolgen:The production of the new dry preparations can be done on different ways:
- 1. Durch Trockenmahlung einer Mischung der Komponenten A, B, C und gegebenenfalls weiterer Formierhilfs mittel bis zu einer Teilchengröße von <50 µm, vor zugsweise <20 µm. Für die Trockenmahlung geeignete Mühlen sind neben der Kugelmühle oder dem Desinte grator, vorzugsweise aber solche Rotor-Stator-Sieb mühlen, die eine ⌀ Korngröße kleiner 20 µm, bevor zugt unter 5 µm erzielen oder sogenannte Strahl mühlen, bzw. Prallkammermühlen. Bevorzugt wird unter Zugabe eines Kältemittels gemahlen, beispiels weise Trockeneis.1. By dry grinding a mixture of the components A, B, C and optionally other forming aids medium to a particle size of <50 microns preferably <20 µm. Suitable for dry grinding Mills are next to the ball mill or the disinte grator, but preferably such rotor-stator sieve mills that have a ⌀ grain size less than 20 µm before pulls below 5 µm or so-called beam mills, or impact chamber mills. Is preferred under Add a refrigerant, for example wise dry ice.
- 2. Die erfindungsgemäßen Präparationen können aber auch in besonderer Weise unter Verzicht auf ein Mahlaggregat so hergestellt werden, daß die er findungsgemäßen Komponenten A, B und C in Form ihrer wäßrigen Lösungen, Suspensionen oder An schlämmungen in einem Rührwerkskessel zusammen gegeben werden und nach guter Durchmischung einem Trockenprozeß unterworfen werden, z. B. in einem Schaufeltrockner, Band- oder Siebtrockner, vorzugsweise aber einen Zerstäubertrockner, wenn die Prä parationen nicht in flüssiger Form in den Handel gebracht werden sollen.2. However, the preparations according to the invention can also in a special way without a Grinder are made so that he Components A, B and C according to the invention in the form their aqueous solutions, suspensions or an slurries in an agitator tank be given and after thorough mixing Be subjected to the drying process, e.g. B. in one Paddle dryer, belt or sieve dryer, preferably but an atomizer dryer if the pre not in liquid form on the market should be brought.
Das Verhältnis von A : B in der Präparation beträgt 0,8 bis 2,4 Mol Komponente A zu 1 Mol Komponente B.The ratio of A: B in the preparation is 0.8 up to 2.4 moles of component A to 1 mole of component B.
Die fertigen Präparationen bestehen im allgemeinen ausThe finished preparations generally exist out
10-80 Gew.-% A+B,
78-18 Gew.-% C und gegebenenfalls
12-2 Gew.-% übrige Hilfsmittel,10-80% by weight A + B,
78-18 wt .-% C and optionally
12-2% by weight of other auxiliaries,
wobei die Summe selbstverständlich 100% ergeben muß.the sum of course must be 100%.
Beispiele für die gegebenenfalls anwesenden übrigen
Hilfsmittel sind:
Entstaubungsmittel, Stellmittel, Lichtschutzmittel,
Puffersubstanzen (d. h. pH-Regulatoren) etc. sowie
Restfeuchte.Examples of the other aids that may be present are:
Dedusting agents, adjusting agents, light stabilizers, buffer substances (ie pH regulators) etc. as well as residual moisture.
Die Einsatzmenge der erfindungsgemäßen Präparationen beträgt 0,02-3, vorzugsweise 0,1-0,5 Gew.-%, be zogen auf Fasermaterial.The amount used of the preparations according to the invention is 0.02-3, preferably 0.1-0.5% by weight pulled on fiber material.
Geeignete Fasermaterialien sind solche aus synthe tischen Polymeren, wie Polyurethanen und synthetischen Polyamiden.Suitable fiber materials are those from synthe table polymers such as polyurethanes and synthetic Polyamides.
Die Färbungen auf diesen Fasern können in herkömmlicher Weise sowohl mit Metallkomplexfarbstoffen als auch mit Säurefarbstoffen erzeugt werden. Bevorzugt sind die Me tallkomplexfarbstoffe, insbesondere die 1 : 2 Chrom- oder 1 : 2 Kobalt-Komplexe von Mono- oder Diazoverbindungen, die in der Literatur in großer Zahl beschrieben und im Handel erhältlich sind. Diese Farbstoffe können auch 1-2 Sulfogruppen enthalten.The dyeings on these fibers can be more conventional Way with both metal complex dyes and Acid dyes are generated. The Me are preferred tall complex dyes, especially the 1: 2 chromium or 1: 2 cobalt complexes of mono- or diazo compounds, which are described in large numbers in the literature and in Are available commercially. These dyes can too Contain 1-2 sulfo groups.
Geeignete Säurefarbstoffe sind insbesondere solche Typen, die üblicherweise in Kombination mit den Metall komplexfarbstoffen eingesetzt werden. Suitable acid dyes are in particular those types which is usually in combination with the metal complex dyes are used.
Die Behandlung der Polyamidmaterialien mit den erfindungsgemäß zu verwendenden Kupferverbindungen kann vor, während oder nach, bevorzugt während der Färbung, er folgen.The treatment of the polyamide materials with the invention copper compounds to be used can during or after, preferably during coloring, he consequences.
Die Färbungen werden nach üblichen Verfahren hergestellt, d. h. im Ausziehverfahren auf dem Jet-Färbe apparat, dem Jigger, der Haspelkufe oder einem Spul färbeapparat oder auf einer Kontinue-Anlage nach den be kannten Klotz- oder Imprägnierverfahren.The dyeings are produced using customary processes, d. H. in the exhaust process on the jet dyeing apparatus, the jigger, the reel runner or a reel dyeing machine or on a continuous line according to the be knew block or impregnation processes.
Der wesentliche Vorteil der neuen Präparationen im Vergleich zu den vorgefertigten Kupfer-Komplexen (vergl. z. B. EP-A 51 188, 2 45 204, 2 52 386, 2 55 481 und DE-A 32 47 051) besteht darin, daß sie ohne großen mechanischen und verfahhrenstechnischen Aufwand herstellbar sind.The main advantage of the new preparations in comparison to the prefabricated copper complexes (cf. e.g. B. EP-A 51 188, 2 45 204, 2 52 386, 2 55 481 and DE-A 32 47 051) is that they have no great mechanical and procedural effort can be produced are.
Dabei ist es als überraschend anzusehen, daß die neuen Präparationen praktisch die gleiche Wirksamkeit wie die separat hergestellten Kupfer-Komplexe aufweisen.It is surprising that the new Preparations practically the same effectiveness as that have separately produced copper complexes.
In den nachfolgenden Beispielen bedeuten "Teile" Ge wichtsteile. In the examples below, "parts" mean Ge important parts.
Eine Mischung ausA mix of
192,40 Tle. Salicylaldoxim (techn. Ware)
171,50 Tle. CuSO₄ · 5 H₂O
231,70 Tle. Ligninsulfonat (Sulfitaufschluß)
231,70 Tle. Naphthalinsulfonsäure-Formaldehydharz
165,30 Tle. Trinatriumphosphat calc.192.40 parts salicylaldoxime (technical goods)
171.50 parts. CuSO₄.5 H₂O
231.70 parts lignin sulfonate (sulfite digestion)
231.70 parts Naphthalenesulfonic acid formaldehyde resin
165.30 parts of trisodium phosphate calc.
wird in einem Reibschnitzler vorzerkleinert. Danach folgen zwei Mahlgänge in einer Siebmühle (Typ Baumeister), und zwaris shredded in a shredder. Then follow two grinding cycles in a sieve mill (type Baumeister), in fact
- a) einmal mit 5 mm Sieb+Trockeneis (1 : 0,25)a) once with 5 mm sieve + dry ice (1: 0.25)
- b) einmal mit 2 mm Sieb+Trockeneis (1 : 0,5)b) once with 2 mm sieve + dry ice (1: 0.5)
Anschließend wird das Pulver entstaubt in einem Lödige- Mischer unter Zusatz von 7,40 Tln. eines Entstaubungs mittels auf Mineralöl-Basis gegeben.The powder is then dedusted in a Lödige Mixer with the addition of 7.40 parts of a dedusting device given on mineral oil basis.
Man erhält 1000 g einsatzfähiges Lichtechtheitsverbesserungs mittel, das in seiner Wirkung dem vorgefertigten Kupfer-Komplex gemäß DE-A 32 47 051 in keiner Weise nachsteht.1000 g of lightfastness improvement which can be used are obtained medium, the effect of the prefabricated Copper complex according to DE-A 32 47 051 in no way is inferior.
Eine wäßrige Dispersion, bestehend ausAn aqueous dispersion consisting of
191,00 Tle. Wasser (als Vorlage)
19,37 Tle. Salicylaldoxim (98%ig)
13,85 Tle. Natronlauge (40%ig)
92,88 Tle. Ligninsulfonat (nach Sulfitaufschluß)
106,38 Tle. Ligninsulfonat (nach Kraftaufschluß)
4,78 Tle. Wasser (zum Spülen)
17,37 Tle. CuSO₄ · 5 H₂O
55,76 Tle. Wasser (zum Lösen des Cu-Salzes)
0,47 Tle. Entstaubungsmittel auf Mineralöl-Basis
4,70 Tle. Wasser (zum Emulgieren des Öls)191.00 parts of water (as template)
19.37 parts salicylaldoxime (98%)
13.85 parts of sodium hydroxide solution (40%)
92.88 parts of lignin sulfonate (after sulfite digestion)
106.38 parts lignin sulfonate (after force digestion)
4.78 parts water (for rinsing)
17.37 parts. CuSO₄.5 H₂O
55.76 parts water (for dissolving the copper salt)
0.47 parts. Dust extractor based on mineral oil
4.70 parts of water (for emulsifying the oil)
wird einer Sprühtrocknung (Eingangstemperatur: 170°C Ausgangstemperatur 90°C; Einstoffdüse) unterworfen.is spray dried (inlet temperature: 170 ° C Initial temperature 90 ° C; Single substance nozzle).
Das erhaltene Pulver ist direkt einsatzfähig.The powder obtained can be used immediately.
1475 g einer wäßrigen Lösung von Cyclohexanol/Bisul fit/Formaldehyd-Kondensat mit einem Trockensubstanz gehalt von 508,6 kg werden in einem Rührkessel ver mischt mit 144,78 kg Natronlauge (40%) sowie 199,8 kg Salicylsäure und 181 kg Kupfer-II-sulfat. Nach Zugabe von 299 kg Wasser, vermischt mit 4,7 kg eines Entstau bungsmittels wird im Zerstäubertrockner abgesprüht, d. h. getrocknet. Man erhält eine Präparation mit sehr hoher Feinverteilung im Färbebad bzw. im Nachbehandlungsbad und guter lichtechtheitsverbessernder Wirkung auf ge färbtem Polyamid. 1475 g of an aqueous solution of cyclohexanol / bisul fit / formaldehyde condensate with a dry substance contents of 508.6 kg are mixed in a stirred tank mixes with 144.78 kg sodium hydroxide solution (40%) and 199.8 kg Salicylic acid and 181 kg copper (II) sulfate. After encore of 299 kg of water mixed with 4.7 kg of a congestion agent is sprayed in the atomizer dryer, d. H. dried. A very high preparation is obtained Fine distribution in the dye bath or in the post-treatment bath and good light fastness improving effect on ge dyed polyamide.
Eine Trockenmischung ausA dry mix
20 Tle. Salicylaldoxim
30 Tle. Ditolylethersulfonsäure/Formaldehyd-Kondensat
15 Tle. Ligninsulfonat (Sulfitaufschluß)
10 Tle. Kupfer-II-chlorid
19 Tle. Trinatriumphosphat
Rest auf 100: Wasser20 parts Salicylaldoxim
30 parts of ditolyl ether sulfonic acid / formaldehyde condensate
15 parts of lignin sulfonate (sulfite digestion)
10 parts of copper (II) chloride
19 parts of trisodium phosphate
Rest on 100: water
zeigt eine ähnlich gute Wirkung wie das Präparat gemäß Beispiel 1. shows a similarly good effect as the preparation according to Example 1.
100 Teile Polyamid-6-Fasermaterial werden in 2000 Teile wäßrige Färbeflotte eingetragen, die 0,15 Teile des Prä parats gemäß Beispiel 1 und 0,15 Teile des Metallkom plex-Farbstoffes der Formel100 parts of polyamide 6 fiber material are made into 2000 parts aqueous dye liquor entered, the 0.15 parts of the pre ready according to Example 1 and 0.15 parts of Metallkom plex dye of the formula
enthält. Durch Zugabe von Dinatriumphosphat und Mono natriumphosphat wird ein pH-Wert von 8 eingestellt. Dann wird die Flottentemperatur unter Bewegung des Färbegutes langsam auf 98-100°C erhöht und für 60 min bei dieser Temperatur belassen.contains. By adding disodium phosphate and mono sodium phosphate is adjusted to a pH of 8. Then becomes the liquor temperature while moving the material to be dyed slowly increased to 98-100 ° C and for 60 min at this Leave temperature.
Anschließend wird die Färbung dem Färbebad entnommen, gespült und getrocknet. The dye is then removed from the dye bath, rinsed and dried.
Die Färbung wird zusammen mit einer ohne Kupfer-Präparation hergestellten Vergleichsfärbung gemäß Test derThe coloring is done together with one without copper preparation prepared comparison staining according to the test of
Adam Opel AG
Rüsselsheim/BRD
GM (Engineering Standards Europe)
GME No 60 202 A/BAdam Opel AG
Ruesselsheim / FRG
GM (Engineering Standards Europe)
GME No 60 202 A / B
während 250 h im Xenontestgerät belichtet.exposed for 250 h in the xenon tester.
Ergebnis: Die mit der Präparation behandelte Färbung zeigt eine erheblich bessere Lichtechtheit als der Ver gleich.Result: The stain treated with the preparation shows a much better light fastness than the Ver equal.
100 Teile Polyamid-6-Material werden in 2000 Teile wäßriger Färbeflotte eingetragen, die 0,45 Teile der in Beispiel 3 beschriebenen Präparation und 0,15 Teile des Farbstoffes der Formel100 parts of polyamide 6 material become more aqueous in 2000 parts Dyeing liquor entered, the 0.45 parts of the in Example 3 preparation and 0.15 parts of Dye of the formula
enthalten. contain.
Die Färbeflotte wird auf pH 5,5 unter Zuhilfenahme eines Puffergemisches aus Mononatriumphosphat und Essigsäure eingestellt. Man behandelt eine Stunde bei 98 bis 100°C, spült und trocknet.The dye liquor is adjusted to pH 5.5 with the aid of a Buffer mixture of monosodium phosphate and acetic acid set. Treated at 98 to 100 ° C for one hour, rinses and dries.
Die so hergestellte Färbung zeigt eine deutlich ver besserte Lichtechtheit.The color produced in this way shows a clearly ver improved lightfastness.
Claims (6)
- A) einen phenolischen Komplexbildner,
- B) ein komplexierbares Kupfer-II-Salz und
- C) ein Dispergiermittel
- A) a phenolic complexing agent,
- B) a complexable copper (II) salt and
- C) a dispersant
Y =N-W, =N-Ar, =N-N-CH-Ar, =N-OH, =N-Ar-N=CH-Ar, -N-AK-N=CH-Ar oder Sauerstoff,
R H, OH, W oder OW und
X₁-X₄ H, W, OH, Halogen, CN, NH₂, NVW, SO₃H, COOH, COOW, CONVW oder CONH₂ bedeuten und zwei benachbarte Reste
X₁-X₄ auch gemeinsam die restlichen Glieder eines ankondensierten Benzolringes bilden können,
wobei
AK für C₂-C₄-Alkylen,
Ar für Aryl oder Arylen,
W für C₁-C₁₈-Alkyl oder Cyclohexyl und
V für W oder H stehen.2. Dry preparation according to claim 1, characterized in that the complexing agent a connec tion of the formula in which - independent of each other -
Y = NW, = N-Ar, = NN-CH-Ar, = N-OH, = N-Ar-N = CH-Ar, -N-AK-N = CH-Ar or oxygen,
RH, OH, W or OW and
X₁-X₄ H, W, OH, halogen, CN, NH₂, NVW, SO₃H, COOH, COOW, CONVW or CONH₂ mean and two adjacent radicals
X₁-X₄ can also together form the remaining members of a condensed benzene ring,
in which
AK for C₂-C₄ alkylene,
Ar for aryl or arylene,
W for C₁-C₁₈ alkyl or cyclohexyl and
V stands for W or H.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3925259A DE3925259A1 (en) | 1989-07-29 | 1989-07-29 | DRY PREPARATION OF LIGHT fastness improvers |
EP90113514A EP0413146B1 (en) | 1989-07-29 | 1990-07-14 | Dry preparation of a better light fastness mixture |
DE59006007T DE59006007D1 (en) | 1989-07-29 | 1990-07-14 | Dry preparation of light fastness improvers. |
AT90113514T ATE106960T1 (en) | 1989-07-29 | 1990-07-14 | DRY PREPARATION OF LIGHT FASTNESS ENHANCEMENT AGENTS. |
JP2194096A JPH0364584A (en) | 1989-07-29 | 1990-07-24 | Dry compounded agent of light resistance improving agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3925259A DE3925259A1 (en) | 1989-07-29 | 1989-07-29 | DRY PREPARATION OF LIGHT fastness improvers |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3925259A1 true DE3925259A1 (en) | 1991-01-31 |
Family
ID=6386187
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3925259A Withdrawn DE3925259A1 (en) | 1989-07-29 | 1989-07-29 | DRY PREPARATION OF LIGHT fastness improvers |
DE59006007T Expired - Lifetime DE59006007D1 (en) | 1989-07-29 | 1990-07-14 | Dry preparation of light fastness improvers. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE59006007T Expired - Lifetime DE59006007D1 (en) | 1989-07-29 | 1990-07-14 | Dry preparation of light fastness improvers. |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0413146B1 (en) |
JP (1) | JPH0364584A (en) |
AT (1) | ATE106960T1 (en) |
DE (2) | DE3925259A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4328670A1 (en) * | 1993-08-26 | 1995-03-02 | Basf Ag | Phenolic complexing agents |
WO2008101833A1 (en) * | 2007-02-20 | 2008-08-28 | Huntsman Advanced Materials (Switzerland) Gmbh | Uva formulation |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3247051A1 (en) * | 1982-12-20 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | METHOD FOR IMPROVING THE LIGHT FASTNESS OF POLYAMIDE COLORS |
US4775386A (en) * | 1986-05-05 | 1988-10-04 | Ciba-Geigy Corporation | Process for photochemical stabilization of undyed and dyed polyamide fibre material and blends thereof with other fibres: copper complex and light stabilizer treatment |
DE3622864A1 (en) * | 1986-07-08 | 1988-01-21 | Bayer Ag | METHOD FOR IMPROVING THE LIGHT FASTNESS OF POLYAMIDE COLORS |
-
1989
- 1989-07-29 DE DE3925259A patent/DE3925259A1/en not_active Withdrawn
-
1990
- 1990-07-14 AT AT90113514T patent/ATE106960T1/en not_active IP Right Cessation
- 1990-07-14 DE DE59006007T patent/DE59006007D1/en not_active Expired - Lifetime
- 1990-07-14 EP EP90113514A patent/EP0413146B1/en not_active Expired - Lifetime
- 1990-07-24 JP JP2194096A patent/JPH0364584A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
JPH0364584A (en) | 1991-03-19 |
DE59006007D1 (en) | 1994-07-14 |
EP0413146A1 (en) | 1991-02-20 |
ATE106960T1 (en) | 1994-06-15 |
EP0413146B1 (en) | 1994-06-08 |
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