GB2248451A - Process for aftertreating anionically dyed substrates - Google Patents
Process for aftertreating anionically dyed substrates Download PDFInfo
- Publication number
- GB2248451A GB2248451A GB9120833A GB9120833A GB2248451A GB 2248451 A GB2248451 A GB 2248451A GB 9120833 A GB9120833 A GB 9120833A GB 9120833 A GB9120833 A GB 9120833A GB 2248451 A GB2248451 A GB 2248451A
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- United Kingdom
- Prior art keywords
- tetramethylpiperidyl
- group
- amino
- formula
- bis
- Prior art date
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Links
- 239000000758 substrate Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000003277 amino group Chemical group 0.000 claims abstract description 11
- 229920002678 cellulose Polymers 0.000 claims abstract description 10
- 239000001913 cellulose Substances 0.000 claims abstract description 10
- 239000004952 Polyamide Substances 0.000 claims abstract description 8
- 229920002647 polyamide Polymers 0.000 claims abstract description 8
- 125000000129 anionic group Chemical group 0.000 claims abstract description 5
- 239000006185 dispersion Substances 0.000 claims abstract description 5
- 239000010985 leather Substances 0.000 claims abstract description 4
- 239000008187 granular material Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract description 4
- -1 amino, imino Chemical group 0.000 abstract description 4
- 238000013508 migration Methods 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 3
- 125000003368 amide group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 5
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- RRETZLLHOMHNNB-UHFFFAOYSA-M sodium;1-amino-9,10-dioxo-4-(2,4,6-trimethylanilino)anthracene-2-sulfonate Chemical compound [Na+].CC1=CC(C)=CC(C)=C1NC1=CC(S([O-])(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O RRETZLLHOMHNNB-UHFFFAOYSA-M 0.000 description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920003620 Grilon® Polymers 0.000 description 1
- WMHPUCYMXUMQIB-UHFFFAOYSA-N N-[7-hydroxy-8-[(2-hydroxy-5-methylsulfonylphenyl)diazenyl]naphthalen-1-yl]acetamide Chemical compound OC1=C(C=C(C=C1)S(=O)(=O)C)N=NC1=C(C=CC2=CC=CC(=C12)NC(C)=O)O WMHPUCYMXUMQIB-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- LIKZXCROQGHXTI-UHFFFAOYSA-M acid blue 25 Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC1=CC=CC=C1 LIKZXCROQGHXTI-UHFFFAOYSA-M 0.000 description 1
- DGOBMKYRQHEFGQ-UHFFFAOYSA-L acid green 5 Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 DGOBMKYRQHEFGQ-UHFFFAOYSA-L 0.000 description 1
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- FEAMVHMFWBXBOJ-UHFFFAOYSA-N chembl3145023 Chemical compound O=C1C(N=NC=2C(=CC=CC=2)C(O)=O)=C(C)NN1C1=CC=CC=C1 FEAMVHMFWBXBOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
A process for aftertreating an anionically-dyed substrate selected from synthetic polyamide, cellulose and cellulose derivatives and leather, is characterized in that the substrate is aftertreated with a solution or dispersion containing one or more cycloaliphatic compounds containing a sterically hindered amine group, which may also be protonated (herein referred to as HALS compounds). The substrate may be in the form of fibres, or chips or granules which are later worked into fibres or other forms. The sterically hindered amine groups of the HALS compounds are preferably bound to a carbocyclic group of aromatic character by means of an ester or amide group or are attached by an amino, imino or ether group to a heterocyclic group (preferably triazine). Preferred HALS compounds have one or more 2,2,6,6-tetramethylpiperidyl-4 or 1,2,2,6,6-pentamethyl piperidyl-4 groupings. The sterically hindered amine groups form salts with the anionic dyestuffs and this improves the migration and wash fastness properties.
Description
0 1^ PROCESS FOR AFTERTREATING ANIONICALLY DYED SUBSTRATES The invention
relates to a process for aftertreating substrates of synthetic polyamide, cellulose and cellulose derivatives (including paper and cotton) and leather that have been dyed with an anionic dye.
According to the invention there is provided a process for aftertreating an anionically-dyed substrate selected from synthetic Polyamide, cellulose and cellulose derivatives and leather, characterized in that the substrate is aftertreated. with a solution or dispersion containing one or more compounds containing a sterically hindered amine group, and/or a sterically hindered amine group which has been protonated (hereinafter referred to as HALS compounds).
Preferred HALS compounds are those containing one or more groups of formula a) to e) below R R R R R 2,:/ 2 / 2 2.
1 0 2 2 R I- 3 R R 2 Y Z 2 2 3 R 2\ 0 2:t Nx 1 R 2 2 R 2 Z. 1 (a) (10) (c) (8) (a) ' in which R, is selected from hydrogen, Cl-4alkyl, C2-4alkenyl, -CO-Cl-4alkyl or - CO-C2-4alkenyl, preferably hydrogen or Cl-4alkyl, each R2 independently is Cl-salkyl (preferably methyl), 1 1 1 -Y- is a moiety of the formula -CO-a - or -N-CO-, the carbon atom Case 153-5466 and the nitrogen atom being positioned in such a way that, together with the carbon atoms to which Y is attached and the oxygen atom joining said carbon atoms, a five membered ring moiety is formed and wherein the starred atoms are attached to the R3 bearing carbon atom, each R3 independently, is selected from hydrogen and Cl-4alkyl or one group R3 is phenyl and the other is hydrogen or Cl-4alkyl or both groups R3 form a group of the formula -(CH2)11-.
These sterically hindered amine groups are preferably bound to a carbocyclic group of aromatic character by means of an ester- or amidegroup or are attached by an amino, imino or ether to a heterocyclic group (preferably triazine).
More preferred HALS compounds are those selected from compounds of formulae 1 to 29.
1.
2.
R 4 R 4 1 (CO-R 4) n 3. 2,3-Bis-(21,21,61,61-tetramethylpiperidyl-41-amino)-quinoxaline, 4. 1, 4-Bis-(21,21,61,61-tetramethylpiperigyl-41-amino)-phthalazine, 5.2-Chloro4,6-bis(21,21,61,61-tetramethylpiperidyl-41-amino)- pyrimidine, 6.2,5-Dichloro-4,6-bis-(21,21,61,6t-tetramethylpiperidyl-4,amino)pyrimidine, 7.2-Fluoro-5-chloro-4,6-bis-(21,21,61,61-tetramethylpiperidyl-41amino)-pyrimidine, 8.2,4,6-Tri-(21,21,61,61-tetramethylpiperidyl-41-amino)-pyrimidine, Case 153-5466 9. 2,4,6-Tri-(21,21,61,61-tetramethylpiperidyl-41-amino)-5chloropyrimidine, 10. 2,4-Bis-(21,21,61,61-tetramethylpiperidyl-41-amino)quinazoline, 11.
CH 3 4 CH 3 -11 "-K CH IM-CO-NH-R 1 4 - NH-R 4 j 0-N N- N NH-R T \--/ 4 NH-R 4 13.
CO-NTH-C2-3Alkylene-NH- NH-R 4 j J-1, 14. N 1 N -(NH-R7)3 15. N -(CO-O-R7)3 V 16. 1 -(-NH-C2-3Alkylene-O-CO-R6)3 N N 17.
20.
N -(NTH-C2-3Alkylene-O-CO-Rg)3 18. -(C0-NH-R8)3 19. (CONH-Rf4)4 C0-NH-R.' R 4 '-NH-CO 4 J - CO-NH-R R 4 ' -NH-CO 1 4 21. -(C0-NH-R4f)3 22. -(CO-O-Re)3 23. -(-HM-C2-3Alkylene-O-CO-R8)3 N 1-e Case 153-5466 Case 153-5466 0 R '-NH-CO 4 CO-NH-R -,Q CO-NH-R 7 \11 4 24.
25.
26.
-(CO-M-R7)3 CO-O-(CH 2)3 -R 10 CO-0- (CH2) 3 -R 10 CO-0- (CH) -R 1 2 3 1P CO-O-(CH2)3 -R 10 27.
28.
29.
Y N '11( :-SI y -{- NH-CH 2 CH 2-0-CO-R 9 1 3 in which n is 2, 3 or 4, R4 is selected from 2,2,6,6-tetramethylpiperidyl-4-amino, 2,2,6,6tetramethylpiperidyl-4-oxy, 1,2,2,6,6-pentamethylpiperidyl-4-amino or 1,2, 2,6,6-pentamethylpiperidyl-4oxy, R41 is a group of formula a) above, R5 is halogen or has a significance of R4, independently of R4, R6 is a group of formula d), R7is the group 1,2,2,6,6-pentamethylpiperidyl-4, RB is a group of formula b), R9 is a group of formula e), Case 1535466 - 1 1 R10 is a group of formula c), where -Y- is the group C0-N-, where the CO group is attached to the piperidyl ring, 1 R101 is the group of formula c), where -Y- is the group -N-CO and the -N- atom is attached to the piperidyl ring, and where in all the groups of formulae a) to e), R, and R3 are hydrogen and each R2 is methyl.
Examples of compounds of formula 1 are 2,4-bis(21,21,61,61tetramethylpiperidyl-4-amino)-6-chlorotriazine (compound 30) and 2,4,6tris(21,21,61 -tetramethyl- piperidyl-4-amino).triazine (compound 31).
Examples of compoundsof formula 2 are compounds 32 to 36.
32. 1,3,5-Tri-(21,21,61,61-tetramethylpiperidyl-41)-trimesinic acid triamide, 33. 1,3,5-Tri-(21,21,61,61-tetramethylpiperidyl-41)-trimellitic acid triamide, 34. Bis-(21,21,61,61-tetramethylpiperidyl-41aminocarbonylparaphenylene)-terephthalic acid diamide, 35. Bis-(21,21,61, 61-tetramethylpiperidyl-41)-isophthalic acid diamide, 36. Bis-(21,21,61, 61-tetramethylpiperidyl-41)-terephthalic acid diamide, 0# Case 153-5466 Most preferably, the HALS compounds are those containing a group of formula a) above, preferably when R, is hydrogen or methyl.
Especially preferred are the compounds having one or more 2,2,6,6tetramethylpiperidyl-4 or 1,2,2,6,6-pentamethylpiperidyl-4 groupings, especially those of formula 1 or 2 defined above.
The above-mentioned HALS compounds are known and can be prepared from known compounds by known methods, for example, by reacting the appropriate acid chloride with the appropriate amine or alcohol or by reacting the appropriate triazine, pyrimidine, quinoxaline or phthalazine halogen compounds with the appropriate amine.
The substrates can be dyed with anionic dyestuffs from aqueous medium by conventional methods. The substrates can be pre-products or the finished textile material of synthetic polyamide, cotton, cellulose or cellulose derivatives especially those substrates from synthetic polyamide, which can be used in the form of chips or other forms having large surface area. These can be treated with aqueous solutions or dispersions of the above mentioned HALS compounds.
In a process according to the invention, the sterically hindered amine groups will, on the whole, form salts with anionic dyestuffs, and this tends to improve the migration properties (by holding migration to a minimum by which in turn the wash fastness properties are improved).
In a process according to the invention, the preferred substrate is synthetic polyamide in the form of chips or granules, that are then later worked into fibers or other forms.
The sterically hindered amine groups may also be present in protonated form, for example, where the sterically hindered amine group is protonated by acid (HCl or acidic acid) or a C1-4alkyl halide.
The abovementioned HALS compounds can be applied, after dyeing, in an exhaust process or by padding (using a pad) from an aqueous solution of Case 153-5466 dispersion. The preferred goods to liquor ratio can be very varied, preferably 1:10 to 1:80 for the aftertreatment.
Preferably the amount of HALS compound that is applied to the substrate is 0.05 to 10%, more preferably 0.5 to 3% based on the weight of the substrate.
Preferably the amount of dyestuff taken up by the substrate is from 1 to 10% inclusive based on the weight of the substrate.
The invention will now be illustrated by the following examples Example 1
Case 153-5466 polyamide-6 chips (Grilon A22, from Fa Emser Verke AG) having a relative solvent viscosity of 2.01 are dyed with 10% (based on the substrate weight) of C.I. Acid Blue 129 in a bath having a liquor to goods ratio of 3:1 maintaining a weak acid bath with 4g/1 of primary sodium phosphate. Dyeing is carried out for two hours at the boil. The resulting colored chips are filtered from the rest of the bath, washed with cold water and aftertreatment is carried out in an.aqueous bath, wherein the ratio of chips to liquor is 1:2 and wherein the liquor contains 0.5 parts of 2,4bis(21,21,61,61-tetramethylpiperidyl-41amino)-6-chloro-- triazine (compound 30) that has been protonated with HC1. The bath is heated over 1 hour to 600C after which it is filtered, washed and dried and spun to fibers.
The resulting deep blue dyed fibers show an excellent light fastness and an improved wash fastness compared to the fibers, dyed in the same way but omitting using the sterically hindered amine treatment step.
Examples 2-35
Example 1 is repeated using instead of the protonated 2,4-bis(21,21,61,61 -tetramethylpiperidyl-41-amino)-6-chlorotriazine (compound 30), an equivalent amount of any one of the compounds of formulae 3 to 29 and 31 to 36 defined above.
Example 1 to 35 can all be repeated using instead of C.I. Acid Blue 129, the same amount of one or more of the following dyestuffs:
C.I.Acid Blue 25, 40, 72, 106, 126, 227, 230, 278, 280 and 296, C.I.Acid Yellow 59, 112p 114, 127 and 129, C.I.Acid Red 261 and 404, C.I.Acid Green 40, C.I.Acid Orange 82, C.I.Acid Violet 66, C.I.Acid Brown 28, 30 and 289, C.I.Acid Black 58 and 115, C.I.Solvent Yellow 83, C.I.Solvent Red 90: 1, 91 and 92 C.I.Solvent Black 45 Case 1535466 0 1 Case 153-5466
Claims (10)
1. A process for aftertreating an anionically-dyed substrate selected from synthetic polyamide, cellulose and cellulose derivatives and leather, characterized in that the substrate is aftertreated with a solution or dispersion containing one or more cycloaliphatic compounds containing a sterically hindered amine group, and/or a sterically hindered amine group that has been protonated (hereinafter referred to as HALS compound).
2. A process according to Claim 1 in which the HALS compound is selected from those containing one or more groups of formulae a) to e) below R.)yR 2 RkIR 2 R,) R 2. R2 R ik2 2 3 2 X E RI-N H R t4 2 2 Y 3 R 2\ 2 F, 2 R 2 (a) (.0) (c) (8) (a) ' in which R, is selected from hydrogen, C,-4alkyl, C2-4alkenyl, -CO-Cl-4alkyl or - CO-C2-4alkenyl, preferably hydrogen or C,-4alkyl, each R2 independently is C,_salkyl (preferably methyl), 1 1 -Yis a moiety of the formula -CO-W - or -N-CO-, the carbon atom and the nitrogen atom being positioned in such a way that, together with the carbon atoms to which Y is attached and the oxygen atom joining Case 153-5466 said carbon atoms, a five membered ring moiety is formed and wherein the starred atoms are attached to the R3 bearing carbon atom, each R3 independently, is selected from hydrogen and Cl-4alkyl or one group R3 is phenyl and the other is hydrogen or Cl-4alkyl or both groups R3 form a group of the formula -(CH2)11-.
3. A process according to Claim 1 in which the HALS selected from compounds of formula 1 to 30:
e N - N /1 1\" R 4 1.
R 4 I (CO-R 4) n 2.
3.2,3-Bis-(21,21,61,61-tetramethylpiperidyl-41-amino)-quinoxaline,
4. 1,4-Bis-(21,21,61,61-tetramethylpiperidyl-41-amino)-phthalazine,
5. 2-Chloro-4,6-bis-(21,21,61,61-tetramethylpiperidyl-41-amino)pyrimidine,
6. 2,5-Dichloro-4,6-bis-(21,21,61,61-tetramethylpiperidyl-4, amino)pyrimidine, 7. 2-Fluoro-5-chloro-4,6-bis-(2',21,61,61-tetramethylpiperidyl-4 amino)pyrimidine, 8. 2,4,6-Tri-(21,21,61,61-tetramethylpiperidyl-41-amino)-pyrimidine, C 6 1 Case 153-5466 9. 2,4,6-Tri-(21,21,61,61-tetramethylpiperidyl-41-amino)-5chloropyrimidine, 10. 2,4-Bis-(21,21,61,61-tetramethylpiperidyl-41-amino)-quinazoline, 11.
12.
13.
14.
CH -CO-NliR ' 3 -""'ll 4 CH 3n "--K CH 3 Nil-CO-NR-R 4 1 - /- \ t4---7 NHR 4 - -CO-N N_ N 4 L_ - TH -CO-N -C2 1 P -OR-R7) 3 NR-R 4 3Alkylene-NH- NR-R 4 1 j 14 Case 153-5466 15. N -(CO-O-R7)3 16. -(-NH-C2-3AlkYlene-O-CO-R6)3 N_ N y 17.
N N -(NH-C2-3Alkylene-O-CO-R9)3 18. -(CO-M-R8)3 19.
1 -- (C0-NE-RIJ4 1 R 4 '-NHCO CO-IM-R co C0-NH-R R 4 '-NIi-CO C 4 21. -(C0-NHR41)3 22.
1 -(CO-O-Re)3 /011 - is - 1 Case 153-5466 $1 y -(-HN-C2-3Alkylene-O-CO-R8)3 N 24. R 4 1 -NH-Co.
CO-NH-R.
7 0 CO-IM-R7 26.
-(CO-M-R7)3 CO-O-(CH 2)3 -R 10 CO-O-(CH 2)3 -R 10 CO-O-(CH) -R 1 2 3 10 CO-O-(CH 2)3 -R 10 27.
28.
N 29. Y"1 14 y -{-NH-CH 2 CH 2 O-CO-R 9 3 3 30. 2,4-Bis-(21,21,61,61-tetramethylpiperidyl-41-amino)-quinazoline, 16 - r Case 153-5466 in which n is 2, 3 or 4, R4 is selected from 2,2,6,6-tetramethylpiperidyl-4-amino, 2,2,6, 6tetramethylpiperidyl-4-oxy, 1,2,2,6,6-pentamethylpiperidyl-4-amino or 1, 2,2,6,6-pentamethylpiperidyl-4-oxy, R4' is a group of formula a) above, R5 is halogen or has a significance of R4,independently of R4, R6 is a group of formula d), R7 is the group 1,2,2,6,6-pentamethylpiperidyl-4, R8 is a group of formula b), R9 is a group of formula e), 1 1 R10 is a group of formula c), where -Y- is the group -CO-N-, where the CO group is attached to the piperidyl ring, 1 Rjolis the group of formula c), where -Y- is the group -N-CO- and the -N- atom is attached to the piperidyl ring, and 1 where in all the formulae a) to e), R, and R3 are hydrogen and each R2 is methyl.
4. A process according to Claim 1 in which the HALS compound- is of formula 1 or 2 R 4 R 4 1.
1 g---- (CO-R 4)n Case 153-5466 in which R4 is selected from 2,2,6,6-tetramethylpiperidyl-4-amino, 2,2,6, 6tetramethylpiperidyl-4-oxy, 1,2,2,6,6-pentamethylpiperidyl-4-amino or 1, 2,2,6,6-pentamethylpiperidyl-4-oxy, R5 is a halogen or has the significance of R4 and n is 2, 3 or 4.
A process according to Claim 4 in which the compounds of formula 1 are compounds 30 or 31 30. 2,4-bis(21,21,61,61-tetramethyl piperidyl-4-amino)-6-chlorotriazine, 31. 2,4,6-tris(21,21,61,6'tetramethylpiperidyl-41-amino)- triazine.
6. A process according to Claim 4 in which the compounds of formula 2 are selected from compound 32 to 36 32. 1,3,5-Tri-(21,2,t61p61-tetramethylpiperidyl-41)-trimesinic acid triamide, 33. 1,3,5-Tri-(21,21,61,61-tetramethylpiperidyl-41)-trimellitic acid triamide, 34. Bis-(21,21,61,61-tetramethylpiperidyl-41-aminocarbonylparaphenylene)terephthalic acid diamide, 35. Bis-(21,2f,61,61-tetramethylpiperidyl-41)-isophthalic acid diamide, 36. Bis-(21,2f,61,61-tetramethylpiperidyl-41)-terephthalic acid diamide.
Case 153-5466 7. A process substantially as herein described with reference to Examples 1 to 33.
8. A substrate dyed with an anionic dye and aftertreated with a HALS compound as defined in Claim 1.
9. A substrate according to Claim 8 in which the substrate is polyamide.
10. A substrate according to Claim 9 in the form of chips or granules or fibers.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4031280 | 1990-10-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9120833D0 GB9120833D0 (en) | 1991-11-13 |
| GB2248451A true GB2248451A (en) | 1992-04-08 |
| GB2248451B GB2248451B (en) | 1994-09-28 |
Family
ID=6415509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9120833A Expired - Fee Related GB2248451B (en) | 1990-10-04 | 1991-10-01 | Process for aftertreating anionically dyed substrates |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPH06346385A (en) |
| CH (1) | CH687283B5 (en) |
| DE (1) | DE4131926A1 (en) |
| FR (1) | FR2667627B1 (en) |
| GB (1) | GB2248451B (en) |
| IT (1) | IT1249712B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5487856A (en) * | 1993-08-16 | 1996-01-30 | Basf Corporation | Process for the manufacture of a post-heat set dyed fabric of polyamide fibers having improved dye washfastness and heat stability |
| WO1996025549A1 (en) * | 1995-02-13 | 1996-08-22 | Ciba Specialty Chemicals Holding Inc. | Process for increasing the sun protection factor of cellulosic fibre materials |
| WO1996029461A1 (en) * | 1995-03-17 | 1996-09-26 | Ciba Specialty Chemicals Holding Inc. | Process for increasing the sun protection factor of cellulosic fibre materials |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005023420A1 (en) | 2005-05-20 | 2006-11-23 | Ems-Chemie Ag | Polyamide molding compounds with improved flowability, their production and their use |
| DE102005023419B4 (en) * | 2005-05-20 | 2007-02-22 | Ems-Chemie Ag | Polyamide oligomers and their use |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1432600A (en) * | 1972-09-20 | 1976-04-22 | Du Pont | Acid dyeable polyesters |
| US4166803A (en) * | 1978-01-09 | 1979-09-04 | Eastman Kodak Company | Heterocyclic benzoate ultraviolet stabilizers and their use in organic compositions |
| JPS60252785A (en) * | 1984-05-29 | 1985-12-13 | 共同薬品株式会社 | Polyester dyed yarn or fabric excellent in light fastness |
| US4812139A (en) * | 1988-05-04 | 1989-03-14 | Burlington Industries, Inc. | Dyed polyester fabrics with improved lightfastness |
| US4874391A (en) * | 1986-07-29 | 1989-10-17 | Ciba-Geigy Corporation | Process for photochemical stabilization of polyamide fiber material and mixtures thereof with other fibers: water-soluble copper complex dye and light-stabilizer |
| EP0352221A1 (en) * | 1988-06-14 | 1990-01-24 | Ciba-Geigy Ag | Process for photochemically stabilising dyed or non dyed polypropylene fibres |
| EP0378054A2 (en) * | 1989-01-05 | 1990-07-18 | Ciba-Geigy Ag | Process for the photochemical stabilization of undyed and ready to be dyed artificial leather |
| DE4000551A1 (en) * | 1989-01-13 | 1990-07-19 | Ciba Geigy Ag | Photochemical stabilisation of dyed wool - by treatment in an aq. bath contg. sterically hindered amine light protection agent |
| EP0379470A2 (en) * | 1989-01-21 | 1990-07-25 | Sandoz Ag | Improved dyeability of synthetic polyamide |
| JPH02242970A (en) * | 1988-08-04 | 1990-09-27 | Honda Motor Co Ltd | Method for improving light and heat resistance of wool fiber |
| CA2019751A1 (en) * | 1989-06-27 | 1990-12-27 | Gerhard Reinert | Process for the photochemical and thermal stabilization of polyamide fibres having an affinity for acid and basic dyes, and of blends of said fibres with one another and with other fibres |
-
1991
- 1991-09-25 DE DE4131926A patent/DE4131926A1/en not_active Withdrawn
- 1991-09-30 CH CH02889/91A patent/CH687283B5/en not_active IP Right Cessation
- 1991-10-01 GB GB9120833A patent/GB2248451B/en not_active Expired - Fee Related
- 1991-10-02 FR FR9112217A patent/FR2667627B1/en not_active Expired - Fee Related
- 1991-10-03 IT ITRM910743A patent/IT1249712B/en active IP Right Grant
- 1991-10-03 JP JP3283616A patent/JPH06346385A/en active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1432600A (en) * | 1972-09-20 | 1976-04-22 | Du Pont | Acid dyeable polyesters |
| US4166803A (en) * | 1978-01-09 | 1979-09-04 | Eastman Kodak Company | Heterocyclic benzoate ultraviolet stabilizers and their use in organic compositions |
| JPS60252785A (en) * | 1984-05-29 | 1985-12-13 | 共同薬品株式会社 | Polyester dyed yarn or fabric excellent in light fastness |
| US4874391A (en) * | 1986-07-29 | 1989-10-17 | Ciba-Geigy Corporation | Process for photochemical stabilization of polyamide fiber material and mixtures thereof with other fibers: water-soluble copper complex dye and light-stabilizer |
| US4812139A (en) * | 1988-05-04 | 1989-03-14 | Burlington Industries, Inc. | Dyed polyester fabrics with improved lightfastness |
| EP0352221A1 (en) * | 1988-06-14 | 1990-01-24 | Ciba-Geigy Ag | Process for photochemically stabilising dyed or non dyed polypropylene fibres |
| JPH02242970A (en) * | 1988-08-04 | 1990-09-27 | Honda Motor Co Ltd | Method for improving light and heat resistance of wool fiber |
| EP0378054A2 (en) * | 1989-01-05 | 1990-07-18 | Ciba-Geigy Ag | Process for the photochemical stabilization of undyed and ready to be dyed artificial leather |
| DE4000551A1 (en) * | 1989-01-13 | 1990-07-19 | Ciba Geigy Ag | Photochemical stabilisation of dyed wool - by treatment in an aq. bath contg. sterically hindered amine light protection agent |
| EP0379470A2 (en) * | 1989-01-21 | 1990-07-25 | Sandoz Ag | Improved dyeability of synthetic polyamide |
| CA2019751A1 (en) * | 1989-06-27 | 1990-12-27 | Gerhard Reinert | Process for the photochemical and thermal stabilization of polyamide fibres having an affinity for acid and basic dyes, and of blends of said fibres with one another and with other fibres |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5487856A (en) * | 1993-08-16 | 1996-01-30 | Basf Corporation | Process for the manufacture of a post-heat set dyed fabric of polyamide fibers having improved dye washfastness and heat stability |
| WO1996025549A1 (en) * | 1995-02-13 | 1996-08-22 | Ciba Specialty Chemicals Holding Inc. | Process for increasing the sun protection factor of cellulosic fibre materials |
| GR960100047A (en) * | 1995-02-13 | 1996-10-31 | Ciba-Geigy Ag | Process for increasing the sun protection factor of cellulosic fibre materials. |
| US5938793A (en) * | 1995-02-13 | 1999-08-17 | Ciba Specialty Chemicals Corporation | Process for increasing the sun protection factor of cellulosic fibre materials |
| WO1996029461A1 (en) * | 1995-03-17 | 1996-09-26 | Ciba Specialty Chemicals Holding Inc. | Process for increasing the sun protection factor of cellulosic fibre materials |
| US5914444A (en) * | 1995-03-17 | 1999-06-22 | Ciba Specialty Chemicals Corporation | Process for increasing the sun protection factor of cellulosic fiber materials |
Also Published As
| Publication number | Publication date |
|---|---|
| ITRM910743A0 (en) | 1991-10-03 |
| CH687283B5 (en) | 1997-05-15 |
| DE4131926A1 (en) | 1992-04-09 |
| CH687283GA3 (en) | 1996-11-15 |
| GB9120833D0 (en) | 1991-11-13 |
| ITRM910743A1 (en) | 1993-04-03 |
| JPH06346385A (en) | 1994-12-20 |
| FR2667627A1 (en) | 1992-04-10 |
| FR2667627B1 (en) | 1993-11-05 |
| IT1249712B (en) | 1995-03-09 |
| GB2248451B (en) | 1994-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20021001 |