CH687283B5 - A method for aftertreatment of dyed with anionic dyes substrates. - Google Patents
A method for aftertreatment of dyed with anionic dyes substrates. Download PDFInfo
- Publication number
- CH687283B5 CH687283B5 CH02889/91A CH288991A CH687283B5 CH 687283 B5 CH687283 B5 CH 687283B5 CH 02889/91 A CH02889/91 A CH 02889/91A CH 288991 A CH288991 A CH 288991A CH 687283 B5 CH687283 B5 CH 687283B5
- Authority
- CH
- Switzerland
- Prior art keywords
- substrates
- amino
- compounds
- chips
- tetramethylpiperidyl
- Prior art date
Links
- 239000000758 substrate Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 8
- 239000000975 dye Substances 0.000 title claims description 7
- 125000000129 anionic group Chemical group 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000004952 Polyamide Substances 0.000 claims description 7
- 229920002678 cellulose Polymers 0.000 claims description 7
- 239000001913 cellulose Substances 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-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
- 238000004043 dyeing Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000005936 piperidyl group Chemical group 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
- 239000002904 solvent Substances 0.000 description 2
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 2
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-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
- 229920003620 Grilon® Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- WXWQVSOHWXJBDF-UHFFFAOYSA-N benzene-1,3,5-tricarboxamide Chemical compound NC(=O)C1=CC(C(N)=O)=CC(C(N)=O)=C1 WXWQVSOHWXJBDF-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 1
- YSVBPNGJESBVRM-UHFFFAOYSA-L disodium;4-[(1-oxido-4-sulfonaphthalen-2-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(N=NC3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)O)=CC=C(S([O-])(=O)=O)C2=C1 YSVBPNGJESBVRM-UHFFFAOYSA-L 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- -1 phthalazine halogen compounds Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 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)
Description
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CH 687 283G A3 CH 687 283G A3
Beschreibung description
Es wurde gefunden, dass mit anionischen Farbstoffen gefärbte Substrate aus synthetischen Polyamiden, Baumwolle, Cellulose und Cellulosederivaten, darunter auch Papier, sowie aus Leder, durch Nachbehandlung mit einer Lösung oder Dispersion, die eine Verbindung enthält, die einen cycloaliphatischen Molekülteil mit sterisch gehinderter Aminogruppe besitzt, in ihrer Licht- und Waschechtheit ganz wesentlich verbessert werden können. It has been found that substrates dyed with anionic dyes made of synthetic polyamides, cotton, cellulose and cellulose derivatives, including paper, as well as leather, by post-treatment with a solution or dispersion which contains a compound which has a cycloaliphatic part of the molecule with a sterically hindered amino group , in their light and wash fastness can be significantly improved.
Unter Verbindungen, die einen cycloaliphatischen Molekülteil mit sterisch gehinderter Aminogruppe besitzen, sind vor allem Verbindungen zu verstehen, die eine Gruppe der Formel a bis e enthalten Compounds which have a cycloaliphatic part of the molecule with a sterically hindered amino group are to be understood in particular as compounds which contain a group of the formulas a to e
"&>< "&> <
R. R.
(C) (C)
«• «•
R, 7 R, R, R, R, 7 R, R, R,
worin Ri Wasserstoff, Ci-2-Alkyl, C2-3-Alkenyl oder Ci-4-Alkylcarbonyl, wherein Ri is hydrogen, Ci-2-alkyl, C2-3-alkenyl or Ci-4-alkylcarbonyl,
alle R2 unabhängig voneinander Ci_s-Alkyl, vorzugsweise Methyl, all R2 independently of one another Ci_s-alkyl, preferably methyl,
>Y- eine Gruppe der Formel -CO-N < oder > N-CO-die beiden R3 unabhängig voneinander Wasserstoff, Ci_2-Alkyl oder ein > Y- a group of the formula -CO-N <or> N-CO-the two R3 independently of one another hydrogen, Ci_2-alkyl or one
R3 Phenyl, das andere Wasserstoff oder Ci-2-Alkyl oder beide R3 is phenyl, the other is hydrogen or Ci-2-alkyl, or both
R3 zusammen eine Gruppe der Formel -(CH2)ti-wobei die Verbindungen mit einer Gruppe der Formel a bevorzugt sind. R3 together is a group of the formula - (CH2) ti - the compounds having a group of the formula a being preferred.
Im allgemeinen werden die auf übliche Weise (mit anionischen Farbstoffen aus wässrigen Medien) gefärbten Susbstrate, vorzugsweise Vorprodukte aus synthetischen Polyamiden oder Cellulosederivaten, insbesondere Substrate aus synthetischen Polyamiden, die in Form von Chips oder anderen Formkörpern mit grosser Oberfläche vorliegen, mit wässrigen Lösungen oder Dispersionen der genannten Verbindungen nachbehandelt. In general, the substrate substrates dyed in the usual way (with anionic dyes from aqueous media), preferably precursors made of synthetic polyamides or cellulose derivatives, in particular substrates made of synthetic polyamides, which are in the form of chips or other shaped articles with a large surface area, are mixed with aqueous solutions or dispersions of the compounds mentioned aftertreated.
Bei der erfindungsgemässen Behandlung bilden die Amino- bzw. Iminogruppen meist Salze mit den anionischen Farbstoffen, was die Migrationsneigung sehr verringert und die Waschechtheit verbessert. In the treatment according to the invention, the amino or imino groups usually form salts with the anionic dyes, which greatly reduces the tendency to migrate and improves the fastness to washing.
Bevorzugte Verbindungen für die erfindungsgemässe Behandlung der genannten gefärbten Substrate sind zum Beispiel Preferred compounds for the treatment according to the invention of the colored substrates mentioned are, for example
1. 1,3,5-T ri-(2',2',6',6'-tetramethylpiperidyl4')-trimesinsäuretriamid, 1. 1,3,5-tri (2 ', 2', 6 ', 6'-tetramethylpiperidyl4') trimesic acid triamide,
2. 1,3,5-T ri-^'^'.e'.e'-tetramethylpiperidyWJ-trimellitsäuretriamid, 2. 1,3,5-tri - ^ '^'. E'.e'-tetramethylpiperidyWJ-trimellitic triamide,
3. 2,4-Bis-(2',2\6',6'-tetramethylpiperidyl4'-amino)-6-chlortriazin, 3. 2,4-bis- (2 ', 2 \ 6', 6'-tetramethylpiperidyl4'-amino) -6-chlorotriazine,
4. 2,4,6-Tri-(2',2',6,,6'-tetramethylpiperidyl4'-amino)-triazin, 4. 2,4,6-tri- (2 ', 2', 6,, 6'-tetramethylpiperidyl4'-amino) -triazine,
5. Bis-(2',2',6',6'-tetramethylpiperidyl4'-aminocarbonyl-paraphenylen)-terephthalsäurediamid, 5. bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl4'-aminocarbonyl-paraphenylene) terephthalic acid diamide,
6. Bis-(2',2',6',6'-tetramethylpiperidyl4')-isophthalsäurediamid, 6. bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl4') - isophthalic acid diamide,
7. Bis-(2',2',6',6'-tetramethylpiperidyl4')-terephthalsäurediamid, 7. bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl4') terephthalic acid diamide,
8. 2,4-B is-(2',2\6',6'-tetramethylpiperidyl4'-amino)-chinazolin, 8. 2,4-B is- (2 ', 2 \ 6', 6'-tetramethylpiperidyl4'-amino) -quinazoline,
9. 2,3-B is-(2',2',6',6'-tetramethylpiperidyl4'-amino)-chinoxalin, 9. 2,3-B is- (2 ', 2', 6 ', 6'-tetramethylpiperidyl4'-amino) -quinoxaline,
10. 1,4-Bis-(2',2',6',6'-tetramethylpiperidyl4'-amino)-phthalazin, 10. 1,4-bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl4'-amino) -phthalazine,
11. 2-Chlor-4,6-bis-(2\2',6',6'-tetramethylpiperidyl-4'-amino)-pyrimidin, 11. 2-chloro-4,6-bis- (2 \ 2 ', 6', 6'-tetramethylpiperidyl-4'-amino) pyrimidine,
12. 2,5-Dichlor-4,6-bis-(2',2',6',6'-tetramethylpiperidyl4'-amino)-pyrimidin, 12. 2,5-dichloro-4,6-bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl4'-amino) pyrimidine,
13. 2-Fluor-5-chlor-4,6-bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)-pyrimidin, 13. 2-fluoro-5-chloro-4,6-bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino) pyrimidine,
14. 2,4,6-Tri-(2',2',6',6'-tetramethylpiperidyl4'-amino)-pyrimidin, 14. 2,4,6-tri- (2 ', 2', 6 ', 6'-tetramethylpiperidyl4'-amino) pyrimidine,
15. 2,4,6-Tri-(2',2',6',6'-teramethylpiperidyl4'-amino)-5-chlorpyrimidin, ferner auch die Verbindungen der Formeln 15. 2,4,6-tri- (2 ', 2', 6 ', 6'-teramethylpiperidyl4'-amino) -5-chloropyrimidine, and also the compounds of the formulas
3 3rd
CH 687 283G A3 CH 687 283G A3
ch, ». ch, ».
n h-co-nh-r' n h-co-nh-r '
ch, nh-co-nh-r; ch, nh-co-nh-r;
CO—N N CO — N N
nh-r; nh-r;
K K
N~\ N ~ \
nh-r' nh-r '
CO-NH-C 2 3 -Alkylen-NH CO-NH-C 2 3 -alkylene-NH
nh-r; nh-r;
K K
•wvw • wvw
N/ (NH-R) N / (NH-R)
i=N i = N
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CH 687 283G A3 CH 687 283G A3
20. 20th
N' v) (C0-0-R7)3 N 'v) (C0-0-R7) 3
i=N i = N
21. 21.
22. 22.
xr v r» xr v r »
N ^ N)^(-NH-C2.3-Alkylen-0-C0-R6)3 N ^ N) ^ (- NH-C2.3-alkylene-0-C0-R6) 3
)-N ) -N
n'' n) (-NH-C2.3-Alkylen-0-C0-R9)3 n '' n) (-NH-C2.3-alkylene-0-C0-R9) 3
r- r-
23. 23.
24. 24th
25. 25th
26. 26.
(CO-NH-R'4)3 (CO-NH-R'4) 3
5 5
CH 687 283G A3 CH 687 283G A3
27. 27.
(C0-0-Rg)3 (C0-0-Rg) 3
10 10th
15 15
28. 28
•w • w
J-' J- '
N ^ (-NH-C2.3-Alkylen-0-C0-R8)3 N ^ (-NH-C2.3-alkylene-0-CO-R8) 3
-N -N
29. 29.
20 20th
Rj-NH-CO Rj-NH-CO
25 25th
30 30th
30. 30th
CO-NH-R, CO-NH-R,
CO-NH-R-, CO-NH-R-,
35 35
40 40
31. 31
(CO-NH-R7)3 (CO-NH-R7) 3
45 45
32. 32.
ci ci
-,N^ -, N ^
'NH-R7 'NH-R7
N N
N N
NH-R, NH-R,
50 50
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33. 33.
O-O-t-CH2)3-Rj0 O-O-t-CH2) 3-Rj0
O-Oi-CH2)3-R10 O-Oi-CH2) 3-R10
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CH 687 283G A3 CH 687 283G A3
CO-O-f-CH2)3-R10 CO-O-f-CH2) 3-R10
34. 34.
CO-O-eCH2)3-R'10 CO-O-eCH2) 3-R'10
35. 35.
N y (NH-CH2CH2-0-C0-R9)3 N y (NH-CH2CH2-0-CO-R9) 3
J—N Y — N
y V y V
ì N in
wobei in der Formel 16 bis 35 where in the formula 16 to 35
FT4 eine Gruppe der Formel a (oben), FT4 a group of formula a (above),
Rô eine Gruppe der Formel d (oben), Rô is a group of formula d (above),
R7 eine 1,2,2,6,6-Pentamethylpiperidyl-4-Gruppe, R7 is a 1,2,2,6,6-pentamethylpiperidyl-4 group,
Rs eine Gruppe der Formel b (oben), Rs is a group of formula b (above),
R9 eine Gruppe der Formel e (oben), R9 is a group of the formula e (above),
R10 eine Gruppe der Formel c (oben), mit Y = -CO-N< und -CO- an den Piperidylring gebunden, R'10 eine Gruppe der Formel c (oben), mit Y = >N-CO-, und >N- an den Piperidylring gebunden, R10 is a group of the formula c (top), with Y = -CO-N <and -CO- attached to the piperidyl ring, R'10 is a group of the formula c (top), with Y => N-CO-, and> N- bound to the piperidyl ring,
worin in allen Formeln Ri und R3 immer Wasserstoff und R2 immer Methyl bedeuten. where in all formulas Ri and R3 are always hydrogen and R2 is always methyl.
Besonders bevorzugt sind hier Verbindungen mit einer oder mehreren 2,2,6,6-Tetramethylpiperidyl-4-oder 1,2,2,6,6-Pentamethylpiperidyl-4-Verbindungen, insbesondere solche der Formeln I oder II Compounds with one or more 2,2,6,6-tetramethylpiperidyl-4 or 1,2,2,6,6-pentamethylpiperidyl-4 compounds, in particular those of the formulas I or II, are particularly preferred here
worin R4 2,2,6,6-Tetramethylpiperidyl-4-amino, 2,2,6,6-Tetramethylpiperidyl-4-oxy, 1,2,2,6,6-Pentamethyl-piperidyl-4-amino, oder 1 ,2,2,6,6-Pentamethylpiperidyl-4-oxy, wherein R4 is 2,2,6,6-tetramethylpiperidyl-4-amino, 2,2,6,6-tetramethylpiperidyl-4-oxy, 1,2,2,6,6-pentamethylpiperidyl-4-amino, or 1 , 2,2,6,6-pentamethylpiperidyl-4-oxy,
Rs Chlor oder eine der Bedeutungen von R4 und n 2, 3 oder 4 bedeuten. Rs is chlorine or one of the meanings of R4 and n is 2, 3 or 4.
Diese genannten Verbindungen sind bekannt, ihre Herstellung erfolgt auf eine dem Fachmann geläufige Weise, z.B. durch Umsetzung der Säurechloride mit den Aminen oder Alkoholen oder der Triazin-, Pyrimidin-, Chinoxalin- und Phthalazin-Halogenverbindungen mit den entsprechenden Aminen. Insbesondere bei der erfindungsgemässen Behandlung von synthetischen Polyamiden in Form von Chips oder Granulat, das erst später zu Fasern oder anderen Formkörpern verarbeitet wird, können die sterisch gehinderten Amine auch in protonierter Form, z.B. mit Säuren (HCl, Essigsäure etc.) oder einem niedrigen Alkylhalogenid protoniert, vorliegen. These compounds mentioned are known, they are prepared in a manner familiar to the person skilled in the art, e.g. by reacting the acid chlorides with the amines or alcohols or the triazine, pyrimidine, quinoxaline and phthalazine halogen compounds with the corresponding amines. In particular in the treatment of synthetic polyamides in the form of chips or granules according to the invention, which is only later processed into fibers or other shaped bodies, the sterically hindered amines can also be used in protonated form, e.g. protonated with acids (HCl, acetic acid etc.) or a lower alkyl halide.
Die genannten Verbindungen mit sterisch gehinderten Aminogruppen werden nach dem Färben im Ausziehverfahren oder nach einem Klotzverfahren (z.B. auf dem Foulard), aus wässriger Lösung oder Dispersion (auf übliche Weise hergestellt) auf das Substrat gebracht. Das Flottenverhältnis kann dabei in weiten Grenzen schwanken, z.B. von 1:10 bis 1:80. Die Menge der eingesetzten Verbindungen liegt im allgemeinen zwischen 0,05 bis 10%, vorzugsweise zwischen 0,5 und 3%, bezogen auf das Gewicht des Substrats, bzw. zwischen 1 und 10% bezogen auf die zur Färbung verwendete Gewichtsmenge Farbstoff. The compounds mentioned with sterically hindered amino groups are applied to the substrate after dyeing in the exhaust process or by a padding process (for example on the padder), from aqueous solution or dispersion (prepared in a customary manner). The fleet ratio can fluctuate within wide limits, e.g. from 1:10 to 1:80. The amount of the compounds used is generally between 0.05 and 10%, preferably between 0.5 and 3%, based on the weight of the substrate, or between 1 and 10% based on the amount by weight of dye used for coloring.
Nichtmattiertes Polyamid-6 (Grilon A22, der Emser Werke AG, Schweiz, relative Lösungsviskosität 2,01, in Form von Chips=Schnitzel, Späne) wurde bei einem Flottenverhältnis von 1:3 unter Zusatz von 4 g/l primärem Natriumphosphat aus schwach saurem Bade mit 10% (bezogen auf das Substratgewicht) C. I. Acid Blue 129 gefärbt. Die Färbezeit betrug 2 Stunden bei Kochtemperatur. Die so gefärbten Chips werden von der Flotte abfiltriert, mit kaltem Wasser gewaschen und im Verhältnis 5 Ge Unmatted polyamide-6 (Grilon A22, from Emser Werke AG, Switzerland, relative solution viscosity 2.01, in the form of chips = chips, chips) was extracted from a weakly acidic mixture at a liquor ratio of 1: 3 with the addition of 4 g / l of primary sodium phosphate Bath colored with 10% (based on the substrate weight) CI Acid Blue 129. The dyeing time was 2 hours at cooking temperature. The chips colored in this way are filtered off from the liquor, washed with cold water and in a ratio of 5 Ge
(I) oder (I) or
Beispiel example
7 7
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 687 283G A3 CH 687 283G A3
wichtsteile gefärbte Chips zu 10 Gewichtsteilen Flotte, enthaltend 0,5 Gewichtsteile mit HCl protoniertes 2,4-Bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)-6-chlortriazin unter Rühren 1 Stunde auf 60°C erhitzt, danach abfiltriert, gewaschen, getrocknet und zu Fasern versponnen. parts by weight of colored chips to 10 parts by weight of liquor, containing 0.5 part by weight of 2,4-bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino) -6-chlorotriazine protonated with HCl with stirring for 1 hour heated to 60 ° C, then filtered off, washed, dried and spun into fibers.
Die so erhaltenen, tief blau gefärbten Fasern zeigen eine bemerkenswert höhere Lichtechtheit und eine bessere Waschechtheit als nicht erfindungsgemäss nachbehandelte Fasern. The deep blue dyed fibers obtained in this way show a remarkably higher light fastness and better wash fastness than fibers not aftertreated according to the invention.
Gemäss den Angaben im obigen Beispiel können auch die Verbindungen der Formeln 1, 2 und 4 bis 35 (oben) mit etwa gleichem Erfolg eingesetzt werden. According to the information in the example above, the compounds of the formulas 1, 2 and 4 to 35 (above) can also be used with approximately the same success.
An Stelle von C. I. Acid Blue 129 können z.B. auch Handelsprodukte der Farbstoffe C. I. Acid Blue 25, 40, 72, 106,126, 129, 227, 230, 278, 280 und 296, C. I. Acid Yellow 59, 112, 114, 127 und 129, C. I. Acid Red 261 und 404, C. I. Acid Green 40, C. I. Acid Orange 82, C. I. Acid Violet 66, C. I. Acid Brown 28, 30 und 289, C. I. Acid Black 58 und 115, C. I. Solvent Yellow 83, C. I. Solvent Red 90: 1, 91 und 92 sowie C. I. Solvent Black 45 eingesetzt werden. Instead of C.I. Acid Blue 129 e.g. also commercial products of the dyes CI Acid Blue 25, 40, 72, 106, 126, 129, 227, 230, 278, 280 and 296, CI Acid Yellow 59, 112, 114, 127 and 129, CI Acid Red 261 and 404, CI Acid Green 40, CI Acid Orange 82, CI Acid Violet 66, CI Acid Brown 28, 30 and 289, CI Acid Black 58 and 115, CI Solvent Yellow 83, CI Solvent Red 90: 1, 91 and 92 and CI Solvent Black 45 .
Claims (5)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4031280 | 1990-10-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CH687283GA3 CH687283GA3 (en) | 1996-11-15 |
| CH687283B5 true CH687283B5 (en) | 1997-05-15 |
Family
ID=6415509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH02889/91A CH687283B5 (en) | 1990-10-04 | 1991-09-30 | A method for aftertreatment of dyed with anionic dyes 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) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2122210C (en) * | 1993-08-16 | 2000-02-15 | Anil W. Saraf | Process for the manufacture of a post-heat set dyed fabric consisting essentially of polyamide fibers with improved dye washfastness and heat stability |
| US5938793A (en) * | 1995-02-13 | 1999-08-17 | Ciba Specialty Chemicals Corporation | Process for increasing the sun protection factor of cellulosic fibre materials |
| TW290606B (en) * | 1995-03-17 | 1996-11-11 | Ciba Geigy Ag | |
| DE102005023419B4 (en) | 2005-05-20 | 2007-02-22 | Ems-Chemie Ag | Polyamide oligomers and their use |
| DE102005023420A1 (en) | 2005-05-20 | 2006-11-23 | Ems-Chemie Ag | Polyamide molding compounds with improved flowability, their production and their use |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6038573A (en) * | 1972-09-20 | 1975-03-20 | Du Pont | Improvement in dyeing polyester fibers |
| 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 |
| EP0352221B1 (en) * | 1988-06-14 | 1994-03-09 | 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 |
| US5030243A (en) * | 1989-01-05 | 1991-07-09 | Ciba-Geigy Corporation | Process for the photochemical stabilization of undyed and dyeable artificial leather with a sterically hindered amine |
| 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 |
| EP0379470B1 (en) * | 1989-01-21 | 1996-03-20 | Sandoz Ag | Improved dyeability of synthetic polyamide |
| EP0409771A3 (en) * | 1989-06-27 | 1991-06-12 | Ciba-Geigy Ag | Process of photochemical and thermal stabilization of polyamide fibres, dyeable by acid and basic dyes, and of their mixtures amongst themselves 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
Also Published As
| Publication number | Publication date |
|---|---|
| DE4131926A1 (en) | 1992-04-09 |
| ITRM910743A0 (en) | 1991-10-03 |
| JPH06346385A (en) | 1994-12-20 |
| CH687283GA3 (en) | 1996-11-15 |
| IT1249712B (en) | 1995-03-09 |
| FR2667627A1 (en) | 1992-04-10 |
| GB2248451B (en) | 1994-09-28 |
| GB2248451A (en) | 1992-04-08 |
| GB9120833D0 (en) | 1991-11-13 |
| ITRM910743A1 (en) | 1993-04-03 |
| FR2667627B1 (en) | 1993-11-05 |
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Legal Events
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| NV | New agent |
Representative=s name: CLARIANT INTERNATIONAL LTD. * SANDOZ TECHNOLOGIE A |
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| PUE | Assignment |
Owner name: SANDOZ AG TRANSFER- CLARIANT FINANCE (BVI) LIMITED |
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| PK | Correction |
Free format text: BERICHTIGUNG ADRESSE |