DEB0029548MA - - Google Patents
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- Publication number
- DEB0029548MA DEB0029548MA DEB0029548MA DE B0029548M A DEB0029548M A DE B0029548MA DE B0029548M A DEB0029548M A DE B0029548MA
- Authority
- DE
- Germany
- Prior art keywords
- cellulose derivatives
- carboxylic acid
- acid esters
- oxyalkylamines
- colored
- 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.)
- Active
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- 229920002678 cellulose Polymers 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- -1 oxy- Chemical class 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- BDFQZTAROXZJOK-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OCCN1CCN(CC1)CCOC(C1=CC=CC=C1)=O Chemical compound C(C1=CC=CC=C1)(=O)OCCN1CCN(CC1)CCOC(C1=CC=CC=C1)=O BDFQZTAROXZJOK-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N Isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitrogen oxide Substances O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- SJSYJHLLBBSLIH-SDNWHVSQSA-N (E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid Chemical compound COC1=CC=CC=C1\C=C(\C(O)=O)C1=CC=CC=C1 SJSYJHLLBBSLIH-SDNWHVSQSA-N 0.000 description 1
- QOSTVEDABRQTSU-UHFFFAOYSA-N 1,4-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NC QOSTVEDABRQTSU-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
- DPTKNRPHFRFPCX-UHFFFAOYSA-N 2-imidazol-1-ylethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN1C=CN=C1 DPTKNRPHFRFPCX-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical class OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N Indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- 229910052813 nitrogen oxide Inorganic materials 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissues Anatomy 0.000 description 1
Description
Tag der Anmeldung: 5. Februar 1954 Bekanntgemacht am 29. März 1956Registration date: February 5, 1954. Advertised on March 29, 1956
Es ist bekannt, daß sich der Farbton und die Klarheit gefärbter Celluloseester und -äther, vor allem in Form von Fasern und Geweben an der Luft zuweilen in unerwünschter Weise ändert, und man hat gefunden, daß diese Farbtonänderung, die insbesondere bei Verwendung von Aminoanthrachinonen als Farbstoffe auftritt, durch in der Atmosphäre vorhandene Stickoxyde veranlaßt wird. Man spricht deshalb von einer schlechten Abgasechtheit solcher Färbungen.It is known that the hue and clarity of colored cellulose esters and ethers, especially in The shape of fibers and tissues sometimes changes undesirably in the air, and it has been found that that this hue change, especially when using aminoanthraquinones as dyes occurs, is caused by nitrogen oxides present in the atmosphere. One therefore speaks of a poor exhaust gas fastness of such dyeings.
R',R ',
R'R '
Es wurde nun gefunden, daß man die Abgasechtheit gefärbter Cellulosederivate erheblich verbessern kann, wenn man sie vor oder nach dem Färben oder im Färbebad selbst mit kleinen Mengen von Carbonsäureestern von Oxyalkylaminen behandelt. Man kann diese Ester auch in die aus den Cellulosederivaten hergestellten Fasern einspinnen.It has now been found that the exhaust gas fastness of colored cellulose derivatives can be improved considerably, if you use them before or after dyeing or in the dyebath even with small amounts of carboxylic acid esters treated by oxyalkylamines. These esters can also be converted into those produced from the cellulose derivatives Spin fibers.
Geeignete Oxyalkylamine, deren Carbonsäureester für das vorliegende Verfahren verwendet werden können, sind z. B. solche der allgemeinen FormelnSuitable oxyalkylamines, the carboxylic acid esters of which are used for the present process can, are z. B. those of the general formulas
:N-(CH2)^-OH oder HO-(CH2)m-N~(CH2)n-OH oder: N- (CH 2 ) ^ - OH or HO- (CH 2 ) m -N ~ (CH 2 ) n -OH or
(I)(I)
R' (III)R '(III)
509' 639/461509 '639/461
B29548IVb/8mB29548IVb / 8m
wobei m, η und χ ganze Zahlen > ι bedeuten und R und R' gleiche oder verschiedene aliphatische, cycloaliphatische oder araliphatische Reste sind; R und R'where m, η and χ are integers> ι and R and R 'are identical or different aliphatic, cycloaliphatic or araliphatic radicals; R and R '
,,. , ■ können ,auch Glieder eines gemeinsamen iso- oder heterocyclischen Ringes sein.,,. , ■ can, also members of a common iso- or be heterocyclic ring.
: ,Solche-Oxyalkylamine sind also z. B. das /?-Diäthylaminoäthanol oder -propanol, das y-Dibutylaminopropanol, das N-ß-Oxyäthylpyrrolidin oder -piperidin, das N-ß-Oxyäthylimidazol, das N-Methyl, -Äthyl-,:, Such oxyalkylamines are z. B. the /? - diethylaminoethanol or propanol, the y-dibutylaminopropanol, the N-ß-Oxyäthylpyrrolidin or -piperidin, the N-ß-oxyethylimidazole, the N-methyl, -äthyl-,
ίο -Cyclohexyl- oder -Benzyl-di-(oxyäthyl)-amin oder das N, N'-Dioxyäthylpiperazin.ίο -Cyclohexyl- or -Benzyl-di- (oxyethyl) -amine or that N, N'-dioxyethylpiperazine.
Als Carbonsäuren, deren Ester mit den genannten Oxyalkylaminen für das vorliegende Verfahren ver-As carboxylic acids, the esters of which are compared with the oxyalkylamines mentioned for the present process
wendet werden, eignen sich insbesondere aromatische, araliphatisshe und ■ cycloaliphatische Carbonsäuren/-wie Benzoesäure, Alkylbenzoesäuren, Phenylessigsäure, . Cyclohexyl- und Cyclohexenylcarbonsäuren, doch sind auch aliphatische Carbonsäuren, wie Essig-, Isobutter- oder Ölsäure, geeignet.are used, aromatic, araliphatic and ■ cycloaliphatic carboxylic acids / such as are particularly suitable Benzoic acid, alkylbenzoic acids, phenylacetic acid,. Cyclohexyl and cyclohexenyl carboxylic acids, however, aliphatic carboxylic acids such as acetic, isobutyric or oleic acid are also suitable.
1000 g eines ■ Acetatreyongewebes werden etwa ι Stunde bei 750 in 20 1 eines wäßrigen Bades bewegt, das 10 g feinverteiltes 1, 4, 5, 8-Tetraaminoanthrachinon und 40 g dispergiertes N, N'-Bis-(2-benzoyloxyäthyl-)piperazin 1000 g of a ■ Acetatreyonewebes are moved for about 1 hour at 75 0 in 20 1 of an aqueous bath containing 10 g of finely divided 1, 4, 5, 8-tetraaminoanthraquinone and 40 g of dispersed N, N'-bis (2-benzoyloxyethyl) piperazine
— CH»- CH »
CnH, — COO — CHo — CH2 — Nk — CH, — CH9-OOC —C n H, - COO - CHo - CH 2 - Nk - CH, - CH 9 -OOC -
CHo--CHo--
enthält. Das in üblicher Weise fertiggestellte Gewebe ist sehr gut abgasecht in mittelblauem Ton gefärbt.contains. The fabric, which is finished in the usual way, is dyed in a medium blue shade that is very resistant to emissions.
ioo g eines Acetatreyonstranges werden ι Stunde bei 8o° in 2 1 eines wäßrigen Bades mit 0,5 g feinverteiltem i-Amino-2-methoxy-4-oxyanthrachinon gefärbt. Nach dem Spülen behandelt man den gefärbten Strang 20 Minuten bei 75 ° im Flottenverhältnis 1: 20 mit einem wäßrigen Bad, das 2 g N-Benzoyloxyäthylimidazol in emulgierter Form enthält. Die erhaltene Rosafärbung ist sehr gut abgasecht.100 g of a Acetatreyonstrange are ι hour colored at 80 ° in 2 liters of an aqueous bath with 0.5 g of finely divided i-amino-2-methoxy-4-oxyanthraquinone. After rinsing, the colored strand is treated for 20 minutes at 75 ° in a liquor ratio of 1:20 with an aqueous bath containing 2 g of N-benzoyloxyethylimidazole contains in emulsified form. The pink color obtained is very resistant to emissions.
100 g eines Acetatreyongewebes werden 45 Minuten bei 75 bis 8o° in 41 Wasser bewegt, das 3 g feinverteiltes i, 4-Diaminoanthrachinon und 6 g des Bisbenzoesäureesters des N-Butyldiäthanolamins100 g of an Acetatreyonewebes 45 minutes at 75 to 80 ° in 41 water, the 3 g finely divided i, 4-diaminoanthraquinone and 6 g of the bisbenzoic acid ester of N-butyl diethanolamine
η — C4H9 — N (CH2 — CH2 — 0OC — C6H6)2 η - C 4 H 9 - N (CH 2 - CH 2 - OOC - C 6 H 6 ) 2
in emulgierter Form enthält. Man erhält eine gut abgasechte Violettfärbung.contains in emulsified form. The result is a violet coloration which is very fast to exhaust gases.
Eine ähnliche Wirkung erzielt man bei Verwendung des Bis-Phenylessigsäureesters des N-Methyldiäthanolamms A similar effect is achieved when using the bis-phenylacetic acid ester of N-methyldiethanolam
H3C-H 3 C-
-CH,-CH,
OOC-CH2-C6H6)2 OOC-CH 2 -C 6 H 6 ) 2
"3^ — N(CH2 "3 ^ - N (CH 2
an Stelle oder neben dem obengenannten Ester.
Beispiel 4in place of or in addition to the above-mentioned ester.
Example 4
1000 g eines Acetareyongewebes werden 1 Stunde bei 750 in 40 1 Wasser bewegt, das 30 g feinverteiltes I, 4-Di-(methylamino-)anthrachinon und 60 g dispergierten Bis-hexahydrobenzoesäureester des N, N'-Di-(ß-oxyäthyl-)piperazins enthält. Man erhält eine sehr gut abgasechte tiefblaue Färbung.1000 g of an Acetareyonewebes are moved for 1 hour at 75 0 in 40 1 of water, the 30 g of finely divided 1,4-di (methylamino) anthraquinone and 60 g of dispersed bis-hexahydrobenzoic acid ester of N, N'-di (ß-oxyethyl -) Contains piperazins. The result is a deep blue coloration which is very fast to exhaust gases.
Zu einer Spinnlösung, die aus 1000 kg Acetylcellulose in der erforderlichen Menge Aceton besteht, gibt man eine acetonische Lösung von N, N'-Bis-(benzoyloxyäthyl-)piperazin, worauf man in üblicher Weise verspinnt.To a spinning solution made from 1000 kg of acetyl cellulose consists in the required amount of acetone, one gives an acetone solution of N, N'-bis (benzoyloxyethyl) piperazine, what is spun in the usual way.
5° kg der so erhaltenen Acetareyonfäden werden So ι Stunde bei 75° mit 2 kg feinverteiltem i-Amino- \ 4- methylaminoanthrachinon - 2 - carbonsäureamid in 1000 1 Wasser gefärbt. Die so erhaltenen klarblauen Färbungen sind sehr gut abgasecht.5 ° kg of the acetareyon threads thus obtained are dyed for so ι hour at 75 ° with 2 kg of finely divided i-amino \ 4-methylaminoanthraquinone-2-carboxamide in 1000 l of water. The clear blue dyeings obtained in this way are very resistant to emissions.
..
Claims (2)
Family
ID=
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