EP0305839A2 - Procédé de teinture de fibres cellulosiques - Google Patents

Procédé de teinture de fibres cellulosiques Download PDF

Info

Publication number: EP0305839A2
Authority: EP; European Patent Office
Prior art keywords: für; alkyl; bis; oder; mit
Prior art date: 1987-09-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

EP88113606A

Other languages

German (de)

English (en)

Other versions

EP0305839A3 (fr

EP0305839B1 (fr

Inventor

Fredgar Dr. Hoffmann

Ergun Dipl.-Ing. Tamer

Manfred Dipl.-Ing. Schnee

Friedhelm Dr. Kersting

Eugen Dipl.-Ing. Rothweiler

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-09-03

Filing date

1988-08-22

Publication date

1989-03-08

1988-08-22 Application filed by Bayer AG filed Critical Bayer AG

1989-03-08 Publication of EP0305839A2 publication Critical patent/EP0305839A2/fr

1991-09-11 Publication of EP0305839A3 publication Critical patent/EP0305839A3/fr

1993-11-10 Application granted granted Critical

1993-11-10 Publication of EP0305839B1 publication Critical patent/EP0305839B1/fr

2008-08-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
238000004043 dyeing Methods 0.000 title claims abstract description 13
150000001412 amines Chemical class 0.000 claims abstract description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000002947 alkylene group Chemical group 0.000 claims abstract description 6
150000001450 anions Chemical class 0.000 claims abstract description 6
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
150000002431 hydrogen Chemical class 0.000 claims abstract description 5
229920003043 Cellulose fiber Polymers 0.000 claims abstract description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 3
239000000975 dye Substances 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 5
239000000982 direct dye Substances 0.000 claims description 5
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000732 arylene group Chemical group 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
230000004087 circulation Effects 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 5
229920000742 Cotton Polymers 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000000985 reactive dye Substances 0.000 description 3
229920000388 Polyphosphate Polymers 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 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 description 2
125000004185 ester group Chemical group 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
-1 naphthyl radicals Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
150000003008 phosphonic acid esters Chemical class 0.000 description 2
239000001205 polyphosphate Substances 0.000 description 2
235000011176 polyphosphates Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000000654 additive Substances 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
150000001449 anionic compounds Chemical class 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
238000010016 exhaust dyeing Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
239000008233 hard water Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002891 organic anions Chemical class 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
NFBAXHOPROOJAW-UHFFFAOYSA-N phenindione Chemical class O=C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 NFBAXHOPROOJAW-UHFFFAOYSA-N 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000979 synthetic dye Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000009970 yarn dyeing Methods 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
- D06P1/60—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 polyethers
- D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
- D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes

Definitions

Cycloalkyl stands in particular for cyclopentyl, cyclohexyl, tetra- or decahydronaphthyl and their derivatives substituted by C 1 -C 12 alkyl.
Suitable aryl radicals are, for example, the phenyl and naphthyl radicals and their derivatives substituted by halogen, C 6 -C 12 alkyl, cyclohexyl or phenyl C 1 -C 3 alkyl.
Aralkyl preferably represents benzyl or phenylethyl substituted by C 5 -C 12 alkyl.
radicals R in formula (I) the dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eikosyl and behenyl radicals.
Suitable anions X 9 are customary inorganic or organic anions, for example chloride, bromide, iodide, methosulfate, sulfate, phosphate or acetate.
the compounds (I) are prepared by known processes.
cellulose in particular with direct dyes, which e.g. in Color Index 3rd Edition (1971), Vol. 2, pp. 2007-2477, and with reactive dyes, e.g. in "The Chemistry of Synthetic Dyes” (K. Venkataraman), Vol. VI (1972).
auxiliaries mentioned is particularly advantageous when dyeing with direct dyes and in particular if salt is added before the dye is added ("all-in" process).
Salt here means the electrolyte, the addition of which is customary to increase the color yield, preferably sodium sulfate or sodium chloride.
the drawing-in of direct dyes is usually controlled by the addition of salt. You start at a low temperature and without the addition of salt in order to prevent it from being drawn up too quickly and the resulting unevenness. Salt is only added, usually in portions, at the end temperature in order to gradually exhaust the dye bath. This is a complex way of working.
Salt can only be added at the beginning only under very favorable conditions (well migrating dyes, high liquor circulation rate or speed of circulation, low demands on levelness). In this way of working, however, the greater inequality that initially arises must be compensated for by migration. This means longer dyeing times with a generally lower color yield.
the salt is added to the dyebath before the dye.
the leveling agent is added before or together with the dye.
the amount of leveling agent is generally between 0.1 and 2%, based on the weight of the textile to be dyed. It is determined in such a way that the initial rate of bath exhaustion lies in a certain range, which is based on the requirements for equality, the goods, the system, the shade and the dyes.
the permissible range is generally 20 to 60% bath exhaustion in the first 10 minutes; preferably it is between 20 and 40% per 10 minutes. It is particularly advantageous to start coloring at a low temperature, preferably between 25 and 40 ° C. From 70 C you can heat quickly.
the initial pH should be between 5.5 and 7.5. If necessary, the dye yield can be increased at the end of the dyeing process by making the pH alkaline (above 8).
the leveling agents (I) are preferably suitable for dyeing with reactive dyes if salt is added from the beginning, but alkali is added later.
the procedure is similar to that for direct dyes. You start at low temperature and neutral to weakly acidic pH. The aid prevents the dyes from being absorbed too quickly in the presence of salt. Then, as usual, the pH is changed and / or heated by adding alkali. This means that the salt can be added at the beginning, even under critical conditions, and the time-consuming and time-consuming metering in can be avoided.
the material carrier is then retracted. After 10 minutes of liquor circulation from the inside to the outside at 40 ° C with 1 ° C / min. heated to 98 ° C. The fleet alternately circulates 10 minutes from the inside out and 5 minutes from the outside in. After 30 minutes at 98 ° C at 2 ° C / min. cooled to 80 ° C. After the liquor has been drained, the coils are dried. A level, light beige coloration is obtained.
Dye (4) from Example 2 (7) added to the cooking wall. After a 10-minute lead at 40 ° C, 1 ° C / min. heated to 70 ° C, stayed there for 10 minutes and at 1 ° C / min. heated to 95 ° C. After dyeing at 95 ° C. for 30 minutes, the mixture is cooled to 80 ° C. in 15 minutes, drained off hot and rinsed once with hard water. A level green coloration is obtained.
the dye liquor is pumped into the apparatus. After 5 minutes of circulation with 2 circulations / min from the inside to the outside through the coil, 3.5 g of the pre-dissolved reactive dye added over the batch vessel.
the mixture is heated to 40 ° C. within 30 minutes, then 22 g of soda calc. and after a further 30 min, 11 ml of NaOH 38 ° Be 'are added via the batch vessel. After a further 30 minutes, the dye liquor is drained off and rinsed as usual. The result is a level red color.

Landscapes

Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Coloring (AREA)

EP88113606A 1987-09-03 1988-08-22 Procédé de teinture de fibres cellulosiques Expired - Lifetime EP0305839B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3729459		1987-09-03
DE19873729459 DE3729459A1 (de)	1987-09-03	1987-09-03	Verfahren fuer das faerben von cellulosefasern

Publications (3)

Publication Number	Publication Date
EP0305839A2 true EP0305839A2 (fr)	1989-03-08
EP0305839A3 EP0305839A3 (fr)	1991-09-11
EP0305839B1 EP0305839B1 (fr)	1993-11-10

Family

ID=6335143

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP88113606A Expired - Lifetime EP0305839B1 (fr)	1987-09-03	1988-08-22	Procédé de teinture de fibres cellulosiques

Country Status (3)

Country	Link
EP (1)	EP0305839B1 (fr)
JP (1)	JPH0197283A (fr)
DE (2)	DE3729459A1 (fr)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH438169A4 (fr) *	1969-03-24	1974-02-28
US3591325A (en) *	1969-04-25	1971-07-06	Arkansas Co Inc	Products and process for removing organic pigments and dyes from dyed and printed natural and synthetic textile materials
BE754502A (fr) *	1969-08-07	1971-01-18	Bayer Ag	Procede de teinture de matieres fibreuses azotees
DE3329445A1 (de) *	1983-08-16	1985-03-07	Bayer Ag, 5090 Leverkusen	Verfahren zum faerben von cellulosefasern
DE3700674A1 (de) *	1986-01-15	1987-07-16	Ciba Geigy Ag	Verfahren zum bedrucken von cellulosischen fasermaterialien

1987
- 1987-09-03 DE DE19873729459 patent/DE3729459A1/de not_active Withdrawn
1988
- 1988-08-22 EP EP88113606A patent/EP0305839B1/fr not_active Expired - Lifetime
- 1988-08-22 DE DE88113606T patent/DE3885549D1/de not_active Expired - Fee Related
- 1988-09-01 JP JP63216426A patent/JPH0197283A/ja active Pending

Also Published As

Publication number	Publication date
EP0305839A3 (fr)	1991-09-11
DE3885549D1 (de)	1993-12-16
JPH0197283A (ja)	1989-04-14
EP0305839B1 (fr)	1993-11-10
DE3729459A1 (de)	1989-03-16

Legal Events

Date	Code	Title	Description
1989-01-21	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
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1993-12-23	ITF	It: translation for a ep patent filed
1993-12-31	ET	Fr: translation filed
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