GB2033929A - Process for dyeing and printing cellulose fibres - Google Patents
Process for dyeing and printing cellulose fibres Download PDFInfo
- Publication number
- GB2033929A GB2033929A GB7934182A GB7934182A GB2033929A GB 2033929 A GB2033929 A GB 2033929A GB 7934182 A GB7934182 A GB 7934182A GB 7934182 A GB7934182 A GB 7934182A GB 2033929 A GB2033929 A GB 2033929A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkoxy
- hydrogen
- alkyl
- dyestuffs
- hydroxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229920003043 Cellulose fiber Polymers 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 23
- 238000004043 dyeing Methods 0.000 title claims description 13
- 238000007639 printing Methods 0.000 title claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 239000000975 dye Substances 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 230000008961 swelling Effects 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229920002678 cellulose Polymers 0.000 claims abstract description 8
- 239000001913 cellulose Substances 0.000 claims abstract description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- -1 C1 - C4 - alkoxy Chemical group 0.000 claims description 48
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229940072056 alginate Drugs 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quiniazarine Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- MXBSQEXFJJQOCG-UHFFFAOYSA-N 1,4-dichloro-5-nitroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MXBSQEXFJJQOCG-UHFFFAOYSA-N 0.000 description 1
- LTKWSXKAESUVPP-UHFFFAOYSA-N 1,5-diamino-4-chloroanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC(Cl)=C2C(=O)C2=C1C=CC=C2N LTKWSXKAESUVPP-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- CNSNLRXGBRBCAU-UHFFFAOYSA-N 5-amino-1,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C=CC=C2N CNSNLRXGBRBCAU-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BKMWYFVZCPYKHT-UHFFFAOYSA-N N-(5-benzamido-9,10-dioxo-4-phenylsulfanylanthracen-1-yl)benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=CC=2C(C3=C(C=CC(=C3C(C12)=O)SC1=CC=CC=C1)NC(C1=CC=CC=C1)=O)=O BKMWYFVZCPYKHT-UHFFFAOYSA-N 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 239000006185 dispersion Substances 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
- 238000005108 dry cleaning Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000010022 rotary screen printing Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/6033—Natural or regenerated cellulose using dispersed dyes
- D06P3/6041—Natural or regenerated cellulose using dispersed dyes using specified dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/585—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aryl radicals
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
- D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Cellulose fibres which can be swollen with water-miscible swelling agents or mixed fibres containing these fibres, are dyed or printed with dyestuffs which are free from sulphonic acid groups and carboxylic acid groups, of the general formula <IMAGE> wherein R represents halogen or optionally substituted alkyl, alkoxy or acylamino, n represents the number 0, 1, 2 or 3, X represents hydrogen, NH-A or <IMAGE> A represents hydrogen or optionally substituted alkyl, cycloalkyl, aryl or acyl and the radicals Y independently of one another represent hydrogen, NH-A, hydroxyl or alkoxy, or one Y represents <IMAGE> and the other Y represents hydrogen or NH-A, and the dyestuff is fixed by heat treatment. Blends of cellulose with polyester or polyamide fibres are employed.
Description
SPECIFICATION
Process for dyeing and printing cellulose fibres
The invention relates to a process for dyeing and printing cellulose fibres which are swollen with water-miscible swelling agents or mixed fibres containing these fibres.
The process is characterised in that the fibres are treated with a dyestuff or several dyestuffs of the general formula
wherein
R represents halogen or optionally substituted alkyl, alkoxy or acylamino,
n represents the number 0,1,2 or 3,
X represents hydrogen, NH-A or
A represents hydrogen or optionally substituted alkyl, cycloalkyl, aryl or acyl and the radicals Y independently of one another represent hydrogen, NH-A, hydroxyl or alkoxy, or one Y represents
and the otherY represents hydrogen or NH-A, and the dyestuff is fixed by heat treatment.
The invention also relates to dyestuff formulations, containing one dyestuff or several dyestuffs of the formula I, for dyeing and printing cellulose and cellulose-containing fibre material.
The dyestuffs of the formula I are free from substituents which render them water-soluble. Examples of suitable substituents of the radicals R, A and
Y are halogen, such as fluorine, chlorine and bromine, C1-C4-alkoxy, hydroxyl, cyano, C,-C-C4- alkoxycarbonylamino and mono- and di-C1
C4-alkylamino, and for the aryl and cycloalkyl radicals also C,-C4alkyl, trifluoromethyl and nitro.
For economic reasons, unsubstituted alkyl radicals and unsubstituted or monosubstituted aryl radicals are preferred. By acyl there is understood, in particular, C1-C4-alkylcarbonyl, benzoyl, C,-C4- alkylsulphonyl, phenylsulphonyl or C,-C4- alkoxycarbonyl, and the alkyl and phenyl radicals can carry the abovementioned substituents.
The alkyl and alkoxy radicals mentioned under R have, in particular, 1-4 carbon atoms, and the alkyl radicals mentioned under A have, in particular, 1-18, for example 1-6, carbon atoms.
By aryl there is understood, preferably, phenyl, and by cycloalkyl preferably cyclohexyl. Examples of the substituents which may be mentioned are: for R: chlorine, bromine, methyl, ethyl, isopropyl, isobutyl, tert.-butyl, methoxy, ethoxy ortert.-butoxy; and for
A: in addition to hydrogen, methyl, ethyl, isopropyl, the isomeric propyl, butyl, pentyl, hexyl, decyl, dodecyl and stearyl radicals, hydroxyethyl, a, ss- dichloropropyl, y-bromopropyl, y-methoxypropyl, y-dimethylaminopropyl, cyclohexyl, the isomeric chloro-, bromo-, methyl-, tert.-butyl- and methoxycyclohexyl derivatives, phenyl which is optionally substituted by 1-3 radicals, such as chlorine, bromine, methyl, ethyl, propyl, butyl, methoxy, acetylamino, methylsulphonylamino or N - methyl
N - acetylamino, for example o-, m- and p-methylphenyl, o-, m- and p-ethylphenyl, p - n butylphenyl, p-tert.-butylphenyl, o-, m- and p-methoxyphenyl, o-, m- and p-ethoxyphenyl, 2,3-, 2,4-, 2,5-, 3,4- and 3,5-dimethylphenyl, 2,4,6trimethylphenyl, 2,4-, 2,5- and 3,5-dimethoxyphenyl, 3 - isopropyl - 4 - methoxy - phenyl, o-, m- and p-chlorophenyl, o-, m- and p-bromophenyl 3-trifluoromethylphenyl, 2,3-, 2,4-, 2,5- and 3,4dichlorophenyl, 2 - chloro - 4 - methylphenyl, 2 chloro - 5 - methylphenyl, 3 - chloro -2 - methylphenyl, 4 - chloro - 2 - methylphenyl, 5 - chloro - 2 - methylphenyl, 2 - bromo - 4 - methylphenyl, 2 chloro- 5 - methoxyphenyl, 5 - chloro - 2 - methox- yphenyl, 2,4 - dimethyl - 6 - bromophenyl, 4 - chloro 2,5 - dimethoxyphenyl, 5 - chloro - 2,4 - dimethoxyphenyl, 3- or4- acetylaminophenyl and 3- or4butyrylaminophenyl, acetyl, propionyl, butyryl, methylsul phonyl, methoxycarbonyl, ethoxycarbonyl and phenylcarbonyl or phenylsulphonyl which can be substituted by methyl, methoxy, chlorine, bromine or acetylamino.
If n -- 1, the radicals R can be identical or different.
Preferred dyestuffs are those of the formula
wherein
R, represents chlorine bromine, C1-C4-alkyl, Ci- C4-alkoxy, C1-C4-alkylca rbonylamino, C-C4- alkylsulphonylamino or benzoylamino which is
optionally substituted by chlorine, bromine, C1-C4alkyl or C1-C4-alkoxy,
n represents the number 0,1, 2or3,
X1 represents hydrogen, NH-A1 or
A1 represents hydrogen, C1 - C, - alkyl, which can optionally be substituted by fluorine, chlorine, bromine, C1 - C4 alkoxy, hydroxyl, C1 - C4 - alkoxycar- bonyl, amino or mono- or di - C1 - C4 - alkylamino, cyclohexyl, which can be substituted by chlorine, bromine, C1 - C4 - alkyl or C1 - C4 - alkoxy, phenyl, which can be substituted by bromine, C1 - C4 - alkyl, trifluoromethyl, C1 - C4 - alkoxy, hydroxyl, amino or mono- or di - C1 - C4 - alkylamino, C1 - C4 - alkyl carbonyl or-sulphonyl or benzoyl or phenylsul phony which is optionally substituted by chlorine, bromine, C, - C4 - alkyl or C1 - C4 - alkoxy and
the radicals Y1 independently of one another represent hydrogen, NH-A1, hydroxyl or C1 - C4 - alkoxy, or
one Y1 represents
and the other Y1 represents hydrogen or NH-Ai.
n particularly represents 0. If n 1, the radicals R and R, can be identical or different.
Dyestuffs of the formulae I and II wherein
X orX1 represents NH2 or NH-A2, in which
A2 = phenyl, which can optionally be substituted by chlorine, bromine, methyl, methoxy, hydroxyl or amino, or wherein
X orX1 represents
in which
R2 = hydrogen, chlorine, bromine, methyl, methoxy, hydroxyl or amino, may be mentioned in particular Dyestuffs of the formulae I and II wherein
one Y or Y1 represents hydroxyl, methoxy, amino or
and
the other Y or V1 denotes hydrogen or amino, or wherein
both Y and Y, represent hydroxyl, may also be mentioned.
The dyestuffs of the formula I are known. They are described, for example, in Swiss Patent Specification 398,843. They are prepared by methods which are in themselves known, for example by replacing some or all of the substituents in known intermediate products which can easily be replaced by phenylmercapto radicals, such as alkoxy radicals, halogen, such as chlorine or bromine, nitro groups or sulpho groups.
Thus, for example, the dyestuff of Example 14 can be obtained by replacing the chlorine atoms in 1 amino - 5,8 - dichloro - anthraquinone by means of K thiophenolate in dimethylformamide or alcohols, and the dyestuff of Example 18 can be obtained by replacing the NO2 group and the chlorine atom in 1 nitro - 5,8 - dichloro - anthraquinone. After introducing the arylmercapto radicals by replacing or modifying substituents by methods which are in themselves know to give dyestuffs which can be used according to the invention, it is also possible to obtain, for example, hydroxy compounds by splitting off ethers, ethers by alkylation of hydroxy compounds, arylamines from amines by reaction with a bromoarylene, acylamines by reaction with acid chlorides, and amines by splitting off acid chlorides or alkylamines.Thus, for example, the dyestuff of
Example 1 can be obtained either by reacting 5 amino - 8 - chloro - quinizarin with thiophenol or by dealkylating 5 - tert. - butylamino - 8 - phenylmercapto - quinizarin with acid agents at elevated temperature, and the dyestuff of Example 3 can be obtained from 1,5 - diamino - 8 - chloro - anthraquinone by reaction with thiophenol or from 1,5 - di acetamino - 8 - phenylmercapto- or 1,5 - dibenzoylamino - 8 - phenylmercapto - anthraquinone by acid saponification.
The dyestuffs to be used according to the invention are dyestuffs which are usually suitable for dyeing and printing synthetic fibres, such as cellulose ester fibres, polyamidefibres and, above all, polyester fibres, as is known, for example, from Swiss
Patent Specification 398,843.
It has now been found that the dyestuffs of the formula (I), which are free from fibre-reactive groups, are outstandingly suitable for dyeing and printing cellulose fibres which can be swollen in water and mixed fibres containing these fibres when they are applied by the processes known from German Auslegeschrift 1,811,796.
In this process, the fibres are brought into contact with an amount of water adequate to swell the cellulose and with a water-miscible swelling agent, before or at the same time as being treated with the dyestuff. The swelling agent must be capable of maintaining the swelling of the cellulose when the water is removed and of dissolving the dyestuff at the dyeing temperature, if necessary with the aid of an additional solubilising agent. The swelling agent is generally added in an amount of 10 to 30% by weight, relative to the cellulose fibres. Suitable swelling agents have a boiling point above 150"C.
The dyestuff and swelling agent can be applied simultaneously to the fibre, or the fibre can first be treated with the swelling agent and then with the aqueous dyestuff dispersion.
Finally, the dyestuff is fixed by heat treatment, in particular at 150 to 230"C.
The process is suitable for dyeing and printing both natural cellulose and regenerated cellulose.
The process is of particular interest for dyeing and printing mixed fibres of cellulose and synthetic fibres, such as polyamide fibres and polyester fibres, in particular cottonlpolyester mixed fibres, since it makes matching-shade dyeing or printing in a single-stage procedure possible.
Process of this type and other auxiliaries and dyestuffs which can be used instead of the products known from German Auslegeschrift 1,811,796 are known, for example, from German Offenlegungsschriften 2,524,243,2,528,743, 2,643,804, 2,700,223 and 2,751,830.
The dyestuffs (I) give dyeings and prints in colour shades which match well on the mixed fibres. They are distinguished by very good fastness properties, and in addition to the fastness to washing, fastness to sublimation, light and drycleaning are to be sing
led out above all.
In addition to water, the dyestuff formulations according to the invention can contain the usual constituents, such as dispersing agents, for example non-ionic and/or anionic and/or cationic dispersing agents, thickeners and/or the abovementioned dyestuff solvents.
The parts mentioned in the examples below are parts by weight and the degrees are degrees Centigrade.
Example 1
A mixed fabric of polyester/cotton in the weight ratio of 50:50-80:20 is printed with a paste which consists of 10 parts of the dyestuff of the formula
110 parts of the reaction product of polyethylene oxide of molecular weight 300 and boric acid in the molar ratio 3:1 and 850 parts of a 10% strength alginate thickener. The print is dried at 105 and then treated with superheated steam at 175 for 6 minutes. The fabric is then successively rinsed with water, soaped at 80 , rinsed again and dried. A reddish-tinged navy blue print which is fast to washing is obtained.
Examples 2- 13
The procedure followed is as described in Example 1, but the dyestuffs of the formula
described in the table below are used. Prints which are fast to washing are obtained in the colour shades indicated in the table.
Example No. X Y Z R n Colourshade 2 NH2 NH2 H 0 claret 3 NH2 H NH2 0 claret 4 NH-COCH3 H H 0 claret 5 NH2 OCH3 OCH3 0 claret 6 NHCH/\CH2 OH OH p-CI 1 blue CH3 7 NH-CH, OH H 0 blue CH2 8 NH2 O-CH2-CH2-OCH3 H 0 blue 9 so H H 0 yellow 10 H OH OH 0 golden yellow 11 H OCH3 SOCH, 0 yellow ,CH3 12 NH-(CH2)q-1{ OH OH 0 blue sCH3 13 NH-SO2-CH3 H OH 0 claret Example t4 A cotton fabric is printed, by rotary screen printing, with a paste which consists of 10 parts of the dyestuff of the formula
100 parts of polyethylene oxide of molecular weight 300 and 890 parts of a 4% strength alginate thickener and is dried at 100"C. The print is then treated with dry heat at 210 for 1 minute. After rinsing, soaping at the boil and rinsing again, a strong neutral-red print which is fast to washing and is sharpley contoured on a white background is obtained.
Examples 15-36
The procedure followed is as in Example 14, but the dyestuffs of the formula
described in the table below are used.
Example No. X, Vi Z1 R n Colour shade 16 S42 H OCH3 0 golden yellow 17 Se H H 0 yellow 18 s42 s42 H 0 orange 19 S42 NH2 NH2 0 blue 20 NH-O OH OH p-C-CH3 CH3 1 navy blue 21 so OCH3 SOCH, p-CH3 1 blue 22 NH-COCH2 H NH-COCH3 0 orange-red CH3 23 NH-CO-( H H p-CH2 1 violet 24 Nn-SO-Cn3 H 0 violet 25 NH2 s e NH2 bluish-tinged 26 NH2 NH2 D 0 violet 27 S e OH OH 0 pink 28 NH H H 0 violet 29 NH\ocH3 OH OH 0 greenish-tinged blue ,CH2 30 NH-(CH2)2-N OH H 0 reddish-tinged \CH2 blue 31 NH-(CH2)tt-CH3 OH OH 0 reddish-tinged blue 32 NH2 NHeCH3 NH2 0 blue 33 NH2 OH NH 0 blue-green 34 NH2 NH453 NH 0 green 35 s 43a H OCH3 0 scarlet 36 /Ob OH 0 navy blue 36 NHf3CCH3 OH %n3 CH3
Claims (10)
1. Process for dyeing and printing cellulose fibres which are swollen by water-miscible swelling agents or mixed fibres containing these fibres, characterised in that the fibres are treated with dyestuffs of the general formula
wherein
R represents halogen or optionally substituted alkyl, alkoxy or acylamino,
n represents the number 1,or3, X represents hydrogen, NH-A or
A represents hydrogen or optionally substituted alkyl, cycloalkyl, aryl or acyl and
the radicals Y independently of one another rep resent hydrogen, NH-A, hydroxyl or alkoxy, or one Y represents
and the others represents hydrogen or NH-A, and the dyestuff is fixed by heat treatment.
2. Process according to Claim 1, characterised in that dyestuffs of the general formula
wherein
R, represents chlorine, bromine, C1 - C4 - alkyl, C1 C4 - alkoxy, C1 - C4 - alkylcarbonylamino, Ct - C4 - alkylsulphonylamino or benzoylamino which is optionally substituted by chlorine, bromine, C1 - C4 alkyl or C1 - C4 - alkoxy,
n represents the number 0, or 3, X1 represents hydrogen, NH-Ai or
A1 represents hydrogen, C1 - C - alkyl, which can optionally be substituted by fluorine, chlorine, bromine, C1 - C4 - alkoxy, hydroxyl, C1 - C4 - alkoxycarbonyl, amino or mono- or di - C1 - C4 alkylamino, cyclohexyl, which can be substituted by chlorine, bromine, C1 - C4 - alkyl or C1 - C4 - alkoxy, phenyl, which can be substituted by bromine, C1 - C4 - alkyl, trifluoromethyl, C1 - C4 - alkoxy, hydroxyl, amino or mono- or di - C1 - C4 - alkylamino, C1 - C4 alkyl - carbonyl or-sulphonyl or benzoyl or phenylsulphonyl which is optionally substituted by chlorine, bromine, C1 - C4 - alkyl or C1 - C4 - alkoxy and
the radicals Y, independently of one another represent hydrogen, NH-A1, hydroxyl or C, - C4 - alkoxy, or
one Y, represents
and the other V1 represents hydrogen or NH-A1, are used.
3. Process according to Claims 1 and 2, characterised in that dyestuffs wherein
n represents 0, are used.
4. Process according to Claims 1 to 3, characterised in that dyestuffs wherein
X orX, represents NH2 or NH-A2, in which
A2 = phenyl, which can optionally be substituted by chlorine, bromine, methyl, methoxy, hydroxyl or amino, are used.
5. Process according to Claims 1 to 3, characterised in that dyestuffs wherein X orX, represents
in which
R2 = hydrogen, chlorine, bromine, methyl, methoxy, hydroxyl or amino,
are used.
6. Process according to Claims 1 to 5, characterised in that dyestuffs wherein
one Y or Y, represents hydroxyl, methoxy, amino or
and
the other Y or Y, represents hydrogen or amino, are used.
7. Process according to Claims 1 to 5, characterised in that dyestuffs wherein
both Y and Y, represent hydroxyl, are used.
8. Process according to Claim 7, characterised in that dyestuffs of the formula
W = hydrogen or phenyl, are used.
9. Process according to Claim 5, characterised in that the dyestuff of the formula
is used.
10. Formulations for dyeing and printing cellulose fibres or cellulose-containing fibre materials, characterised in that they contain a dyestuff of the general formula
wherein
R represents halogen or optionally substituted alkyl, alkoxy or acylamino, n represents the number 0,1,2 or3,
X represents hydrogen, NH-A or
A represents hydrogen or optionally substituted alkyl, cycloalkyl, aryl or acyl and
the radicals Y independently of one another represent hydrogen, NH-A, hydroxyl or alkoxy, or one Y represents
and the other Y represents hydrogen or NH-A.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782843703 DE2843703A1 (en) | 1978-10-06 | 1978-10-06 | METHOD FOR DYEING AND PRINTING CELLULOSE FIBERS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2033929A true GB2033929A (en) | 1980-05-29 |
Family
ID=6051614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7934182A Withdrawn GB2033929A (en) | 1978-10-06 | 1979-10-02 | Process for dyeing and printing cellulose fibres |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5551882A (en) |
| DE (1) | DE2843703A1 (en) |
| FR (1) | FR2438112A1 (en) |
| GB (1) | GB2033929A (en) |
| IT (1) | IT7926268A0 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4294581A (en) | 1978-11-30 | 1981-10-13 | Basf Aktiengesellschaft | Uniformly dyed water-swellable cellulosic fibers |
| US4446047A (en) * | 1981-02-25 | 1984-05-01 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| US4455253A (en) * | 1981-02-25 | 1984-06-19 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| US4464282A (en) * | 1981-02-25 | 1984-08-07 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britian And Northern Ireland | Organic materials |
| US4496221A (en) * | 1981-02-25 | 1985-01-29 | Secretary of State for Defence in Her Britanic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland of Whitehall | Liquid crystal compositions with pleochroic anthraquines dyes |
| US4528113A (en) * | 1983-03-29 | 1985-07-09 | Mitsubishi Chemical Industries Limited | Anthraquinone dye and liquid crystal composition containing the dye |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2094822B (en) * | 1981-02-25 | 1986-03-05 | Ici Plc | Anthraquinone dyes |
| DE3150822A1 (en) * | 1981-09-05 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | LIQUID CRYSTAL MATERIAL CONTAINING ANTHRACHINONE DYES AND NEW ANTHRACHINONE DYES |
| JPS5927956A (en) * | 1982-07-17 | 1984-02-14 | バイエル・アクチエンゲゼルシヤフト | Bichromophoric substance containing anthraquinone dye and novel anthraquinone dye |
| DE3314467A1 (en) * | 1982-07-17 | 1984-01-19 | Bayer Ag, 5090 Leverkusen | DICHROITIC MATERIAL, CONTAINING ANTHRACHINONE DYES AND NEW ANTHRACHINONE DYES |
-
1978
- 1978-10-06 DE DE19782843703 patent/DE2843703A1/en not_active Withdrawn
-
1979
- 1979-10-02 GB GB7934182A patent/GB2033929A/en not_active Withdrawn
- 1979-10-04 JP JP12744479A patent/JPS5551882A/en active Pending
- 1979-10-04 IT IT7926268A patent/IT7926268A0/en unknown
- 1979-10-05 FR FR7924882A patent/FR2438112A1/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4294581A (en) | 1978-11-30 | 1981-10-13 | Basf Aktiengesellschaft | Uniformly dyed water-swellable cellulosic fibers |
| US4446047A (en) * | 1981-02-25 | 1984-05-01 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| US4455253A (en) * | 1981-02-25 | 1984-06-19 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| US4464282A (en) * | 1981-02-25 | 1984-08-07 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britian And Northern Ireland | Organic materials |
| US4496221A (en) * | 1981-02-25 | 1985-01-29 | Secretary of State for Defence in Her Britanic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland of Whitehall | Liquid crystal compositions with pleochroic anthraquines dyes |
| US4528113A (en) * | 1983-03-29 | 1985-07-09 | Mitsubishi Chemical Industries Limited | Anthraquinone dye and liquid crystal composition containing the dye |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7926268A0 (en) | 1979-10-04 |
| JPS5551882A (en) | 1980-04-15 |
| DE2843703A1 (en) | 1980-04-17 |
| FR2438112A1 (en) | 1980-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |