GB2034358A - Process for dyeing and printing cellulose fibres - Google Patents
Process for dyeing and printing cellulose fibres Download PDFInfo
- Publication number
- GB2034358A GB2034358A GB7934181A GB7934181A GB2034358A GB 2034358 A GB2034358 A GB 2034358A GB 7934181 A GB7934181 A GB 7934181A GB 7934181 A GB7934181 A GB 7934181A GB 2034358 A GB2034358 A GB 2034358A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- amino
- dyestuffs
- optionally substituted
- alkoxy
- 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- Withdrawn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 10
- 238000000034 method Methods 0.000 title claims description 26
- 238000004043 dyeing Methods 0.000 title claims description 14
- 238000007639 printing Methods 0.000 title claims description 13
- -1 monoalkyl- Chemical group 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000000460 chlorine Substances 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 13
- 230000008961 swelling Effects 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract description 4
- 239000000975 dye Substances 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino 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
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 abstract description 6
- 239000001913 cellulose Substances 0.000 abstract description 6
- 239000004952 Polyamide Substances 0.000 abstract description 3
- 229920002647 polyamide Polymers 0.000 abstract description 3
- 125000004663 dialkyl amino group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000004744 fabric Substances 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 244000172533 Viola sororia Species 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid 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
- 238000001035 drying Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound 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
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
- WBBFBHOZKCHJHN-UHFFFAOYSA-N 2-amino-1-hydroxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(O)C(N)=CC=C3C(=O)C2=C1 WBBFBHOZKCHJHN-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000003755 preservative agent Substances 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000010020 roller printing Methods 0.000 description 1
- 238000010022 rotary screen printing Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000243 solution Substances 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
- 238000001238 wet grinding 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
- 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
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
-
- 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
Abstract
Cellulose fibres which have been 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 X represents a direct bond, CO-, SO2- or an alkylene group which is optionally substituted or interrupted by oxygen, the radicals Y independently of one another represent hydrogen, hydroxyl, optionally substituted alkoxy, nitro or NH-A, A represents hydrogen or optionally substituted alkyl or acyl, R represents halogen, amino or optionally substituted alkyl, alkoxy, alkylmercapto, monoalkyl-, dialkyl- or acyl-amino, cycloalkyl or aryl, Hal represents chlorine or bromine, n represents 0, 1, 2 or 3 and r represents 0 or 1, with the proviso that there is not more than 1 acylamino group on a nucleus, and Y and NH-A do not simultaneously represent an acylamino group and an NH2 group, and the dyestuffs are fixed by heat treatment. The cellulose may be blended with polyester or polyamide fibres.
Description
Process for dyeing and printing cellulose fibres
The invention relates to a process for dyeing and printing cellulose fibres which have been 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 of the general formula
wherein
X represents a direct bond, CO-, SO2 or an alkylene group which is optionally substituted or interrupted by oxygen,
the radicals Y independently of one another represent hydrogen, hydroxyl, optionally substituted alkoxy, nitro or NH-A,
A represents hydrogen or optionally substituted C,-C4-alkyl or acyl,
R represents halogen, amino or optionally substituted alkyl, alkoxy, alkylmercapto, monoalkyl, dialkyl- or acyl-amino, cycloalkyl or aryl,
Hal represents chlorine or bromine,
n represents 0, 1, 2 or 3 and
r represents 0 or 1, with the proviso that there is not more than one acylamino group on a nucleus, and Y and NH-A do not simultaneously represent an acyl-amino group and an NH2 group, and the dyestuff is fixed by a heat treatment.
If n represents a number > 1, the radicals R can be identical or different.
The invention also relates to dyestuff formulations, containing a dyestuff of the formula (I), for dyeing and printing cellulose fibres and cellulose-containing mixed fibres.
The dyestuffs of the formula (I) are free from substituents which render them water-soluble.
The alkyl radicals mentioned under R preferably have 1-8 carbon atoms. The alkyl radicals mentioned under A and Y and the aliphatic radicals mentioned under Y, R and A preferably have 1-4 carbon atoms. Examples of substituents of these radicals are C,-C4-alkoxy, hydroxyl, cyano, C,-C4-alkoxycarbonyl, amino and mono- or di-C,-C4-alkyl-amino.
Aryl preferably represents phenyl.
By cycloalkyl there is understood, in particular, cyclohexyl which is optionally substituted by
C,-C4-alkyl, C1-C4-alkoxy, chlorine or bromine.
Acyl preferably represents C,-C4-alkyl-carbonyl or -sulphonyl, benzoyl, phenylsulphonyl or C1- C4-alkoxycarbonyl, and the alkyl radicals can carry the abovementioned substituents and the phenyl radicals can also be substituted by these substituents or by C,-C4-alkyl.
In the case of the radical R, halogen is preferably chlorine or bromine.
By alkylene there is understood, in particular, C,-C4-alkylene for an unbroken chain, and if alkylene is interrupted by oxygen, each of the two alkylene radicals preferably has 2 or 3 carbon atoms. The hydroxyl group may be mentioned as an example of a substitutent for alkylene.
Examples of the substituents which may be mentioned are: for X: CO, SO2, methylene, ethylene, n- and iso-propylene, n- and iso-butylene, 2-hydroxypropylene and 3-oxapent-1,5ylene; for Y: in addition to H, OH, NH2 and NO2: methoxy, ethoxy, ssmethoxy-ethoxy, methylamino, ethylamino, tert.-butylamino and acetylamino; for A: in addition to hydrogen: methyl, ethyl, iso-propyl, tert.-butyl, acetyl and benzoyl or phenylsulphonyl which is optionally substituted by methyl; and for R: chlorine, bromine, methyl, ethyl, propyl, butyl, hexyl, octyl, cyclohexyl, methylcyclohexyl, methoxy-cyclohexyl, dimethylamino-methyl, methoxy, ethoxy, propoxy, n-, iso and tert.-butoxy, fi-hydroxyethoxy, fi-methoxy-ethoxy, P-amino-ethoxy, fi-diethylam- ino-ethoxy, fi-cyanoethoxy, methyl-, ethyl- or n-propyl-mercapto, methyl-amino, n- and isopropylamino, n-, iso- and tert.-butyl-amino, y-dimethylamino-n-propylamino, acetyl, propionyl, butyryl, chloroacetyl, methoxy-carbonyl, methylaminocarbonyl, methylsulphonyl and butylsulphonyl.
n preferably represents 0 or 1.
Preferred dyestuffs are those of the formula
wherein
X, represents a direct bond, CO, SO2, a C,-C4-alkylene group which is optionally substituted by hydroxyl or a XC4-C6-alkylene bridge which is interrupted by oxygen,
the radicals Y1 independently of one another represent hydrogen, hydroxyl, C,-C4-alkoxy, nitro or NH-A,.
A, represents hydrogen, C,-C4-alkyl, C,-C4-alkyl-carbonyl or -suiphonyl, benzoyl or phenylsulphonyl,
R, represents chlorine, bromine, amino, C,-C8-alkyl, C,-C4-aikoxy, C,-C4-alkylmercapto, monoor di-C,-C4-alkylamino, C,-C4-alkyl-carbonylamino or -sulphonylamino, benzoylamino, phenylsulphonyl-amino, cyclohexyl or phenyl,
Hal represents chlorine or bromine,
n, represents 0 to 2 and
r represents 0 to 1, and wherein the alkyl, alkoxy, phenyl and cyclohexyl radicals can be substituted by fluorine, chlorine, bromine, hydroxyl, C,-C4-alkoxy, cyano, C,-C4-alkoxyearbonyl, amino or mono- or di-C1
C4-alkylamino and the phenyl and cyclo-hexyl radicals can additionally be substituted by C,-C4alkyl, and wherein Y, and NH-A, are not simultaneously present as the C,-C4-alkylcarbonylamino or benzoylamino group and the NH2 group.
In formula (II), A, particularly represents hydrogen, C,-C4-alkyl or C,-C4-alkylcarbonyl.
Of the dyestuffs of the formula II, those of the formula
wherein
A2 represents hydrogen or C1-C4-alkyl and the remaining symbols have the meaning indicated in the case of formula II, are to be singled out.
Within the scope of the formulae (l)-(lll), n or n, preferably represents O or 1 and R or R, preferably represents chlorine, bromine, C,-C4-alkyl or C-C2-alkoxy.
Other preferred dyestuffs are those of the formula
wherein
one Y2 represents hydrogen,
the other Y2 represents hydroxyl, amino, methoxy or nitro and
the remaining symbols have the abovementioned meaning.
Dyestuffs in which
A2 = branched C3- or C4-alkyl, are of particular interest.
Another preferred group of the dyestuffs (l)-(lV) are those in which
Y, Y, or Y2 represents hydroxyl.
Of these, the dyestuffs (III) in which
A2 = hydrogen or branched C- or C4-alkyl and
r = 0, are in turn preferred.
The preparation of the dyestuffs I is effected by methods which are in themselves known and is described, for example, in German Patent Specification 1,285,646 and German Offenlegungsschriften 2,200,107 and 2,307,591. Examples which may be mentioned are: the preparation from 5,8-dihalogeno derivatives, preferably 5,8-dichloro derivatives, of quinizarin or of 1-nitro-, 1-hydroxy-, 1-amino-, 1-amino-4-hydroxy- or 1,4-diamino-anthraquinone by replacing halogen by the radicals
Acyl radicals can be introduced by acylating NH2 groups (for example where X = SO2 or CO).
Unsubstituted amino groups (A = H or Y) can be introduced by reducing nitro groups, by saponifying acylamino groups or by splitting suitable alkylamino groups. Substituted amino radicals can also be introduced by replacing nitro groups, for example by replacing all or some of the nitro groups in dinitro-anthraquinones. Substituted amino radicals in the p-position relative to other amino radicals can be introduced, for example, in a two-stage process via the corresponding halogen derivatives. External halogen can be introduced with the reactive radicals or by subsequent halogenation by methods which are in themselves known.
Both single dyestuffs I and mixtures of dyestuffs I can be used in the process according to the invention. The dyestuff mixtures can be obtained either by subsequent mixing or already in the course of the preparation.
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, polyamide fibres and, above all, polyester fibres, as is described, for example, in German Offenlegungsschrift 2,307,592.
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 process known from German Auslegeschrift 1,811,796. In this process, the fibres are brought into contact with an amount of water adequate for swelling 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 1 50 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 cotton/polyester mixed fibres, since it makes matching-shade dyeing or printing in a single-stage procedure possible.
Processes 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 2,050,961, 2,524,243, 2,528,743, 2,705,716 and 2,751,830 and from U.S. Patent Specifications 3,752,645, 3,752,646 and 3,752,647.
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 fastness to washing, fastness to sublimation, light and dry cleaning may be singled out above all.
Besides 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 above-mentioned swelling agents and/or dyestuff solubilising agents.
The parts mentioned are degrees Centrigrade.
Example 1
A polyester/cotton 65:35 fabric is printed with the following printing paste: 1-50 parts of a 30% strength paste of the dyestuff of the formula
100 parts of a boric acid ester of a polyethylene glycol, 500 parts of a 4% strength alginate thickener and 399-350 parts of water.
The fabric is then dried, the dyestuff is fixed at 210 with dry heat for 1 minute and the fabric is rinsed, soaped, rinsed again and dried. A green, sharply contoured print which is fast to light is obtained.
The dyestuff paste employed can be obtained as follows: 300 parts of the above dyestuff are dispersed with 60-90 parts of a non-ionic dispersing agent and 640-610 parts of water in a ball mill or another suitable apparatus.
Preservatives and, to prevent rapid drying, glycols or glycerol can also be added to this paste.
Examples 2-7
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 and have the colour shades indicated in the last column are obtained.
Example No. X A Y Z R n Colour shade CH3 2 CO CH OH H 0 blue-violet CH3 3 - H H NO2 pe 1 blue-violet CH3 4 SO2 C - CH3 OH OH p-CH3 1 blue CH3 5 - H H g)-(CH2)2] o-OCH3 1 blue -OCH3 6 - H OH OH p-OCH3 1 greenish-tinged blue CH3 CH3 7 - CH OH NHCOCH3 p-CH 1 green CH3 CH3
Example 8
A polyester/cotton 50:50 fabric is printed with the following printing paste: 1-50 parts of a 30% strength paste of the dyestuff of the formula
100 parts of polyethylene glycol of molecular weight 400, 500 parts of a 10% strength guar thickener and 399-350 parts of water.
A rotary screen printing machine or screen printing tables are used.
If a roller printing machine is used, the amount of polyethylene glycol must be increased to 150-200 parts, depending on the depth of the gravure cells. The fabric is then dried and the dyestuff is fixed at 210"C with dry heat for 1 minute. After rinsing, soaping and rinsing again, blue prints which are fast to washing are obtained.
The dyestuff paste used can be obtained analogously to that in Example 1.
Examples 9-15
The procedure followed is as described in Example 8, but the dyestuffs of the formula
described in the table below are used. Prints which are fast to washing and have the colour shades indicated in the last column of the table are obtained.
Example No. X A Y Z R n Colour shade 9 - H OH OH m,p-CI 2 blue CH3 10 - C-CH3 OH OH o,o,p-CH3 3 blue CH3 11 - H OCH3 OCH3 p-NH-COCH3 1 reddish-tinged blue 12 CH2-CH2 CD4 3 H H - 0 violet - CH3 13 - H H NHC-CH3 m-Br 1 blue CH3 14 - H OH NH2 p-C8H17(iso) 1 blue 15 - H H H ,CH3 ; blue
Example 16
A polyester/cotton 50:50 fabric is padded with a 10% strength solution of polyethylene glycol of molecular weight 400, with a squeezing effect of ~ 100%. It is then printed with a paste comprising 1-100 parts of a 30% strength paste of the dyestuff
40-50 parts of a thickener concentrate which essentially consists of polyacrylic acid which has been broken down under alkaline conditions, and 900 parts of water.
The fabric is then dried and the dyestuff is fixed at 175"C with high-temperature steam for 6 minutes. After rinsing, soaping and rinsing again, a deeply bluish-tinged red print with good fastness properties is obtained.
The dyestuff paste can be obtained analogously to the statements of Example 1.
Examples 17-22
The procedure followed is as indicated in Example 16, but the dyestuffs of the formula
described in the table below are used. Prints with good fastness properties and with the colour shades mentioned in the last column are obtained.
Example No. X A Y Z R n Colour shade 17 -CH(CH2)2 H H OH - 0 violet CH3 18 - H H H p-O-(CH2)2OH 1 violet CH3 19 - H H H p-C - CH3 1 blue CH3 20 SO2 H H H H 1 reddish-tinged violet 21 CO (CH2)3-OCH3 H H m-OCH3 1 reddish-tinged violet CH3 22 - H OH H p-CH2-N 1 blue CH3 CH3 CH3 23 - CH OH H p-O-CH3 1 green CH3 CH3
Example 24
The procedure followed is as described in Example 1, but the dyestuff employed in that example is used as a mixture with the dyestuff of Example 6 in the ratio 1:2 - 2:1.
Blue-green fast prints are obtained.
Such a dyestuff mixture can be obtained by reacting 5-tert.-butylamino-8-chloro-quinizarin and 6-amino-8-chloro-quinizarin separately with p-anisidine and appropriately mixing the dyestuffs in preparing the dyestuff paste as described, or by reacting a mixture of 5-tert.-butylamino-8chloro-quinizarin and 5-amino-8-chloro-quinizarin with p-anisidine, or from the pure dyestuff of
Example 1 by splitting off some of the alkyl radical with acid agents, for example with ptoluenesulphonic acid, in nitrobenzene as a solvent, at elevated temperature.
Example 25
30 parts by weight of the dyestuff
are finely dispersed with 1 5 parts by weight of a reaction product of abietic acid and about 50 mols of ethylene oxide, and 55 parts of water with the aid of a bead mill. The following dye liquor is prepared from this finished dyestuff:
70 parts of the dyestuff formulation
100 parts of a polyethylene glycol of molecular weight 500
10 parts of a 10% strength aqueous solution of a polyacrylate and
820 parts of water 1,000 parts.
A polyester/cotton mixed fibre with a polyester:cotton ratio of 63:35 to 50:50 is impregnated with the aid of a padder, the liquor pick-up of the fabric being 35 to 50%. The fabric treated in this way is dried and the dyestuff is fixed on both fibres by a hot air treatment in a thermosol unit at 215"C for 60 seconds.
After the usual after-treatment by soaping at 60"C and after drying, a full greenish-tinged blue colour shade which matches very well on the two materials is obtained. The dyeing produced has a good fastness to daylight and fastness to dry grinding and wet grinding, and very good fastness to washing.
Examples 26-33
Using the dyestuffs described in the table below, the shades indicated are obtained on polyester/cotton according to the above statements
Example No. R Hal n Colour shade 26 H Cl 0.7 greenish-tinged blue 27 p-C(CH3)S Cl 0.5 28 p-OCH3 Cl 0.3 29 o,p-CI Cl 0.8 30 m-CF3 Cl 0.6 31 p-S-CH3 Br 1 32 p-C2H5 Br 1 33 pe Cl 1
Claims (9)
1. Process for dyeing and printing cellulose fibres which have been swollen with watermiscible swelling agents or mixed fibres containing these fibres, characterised in that the fibres are treated with dyestuffs of the general formula
wherein
X represents a direct bond, CO-, SO2- or an alkylene group which is optionally substituted or interrupted by oxygen,
the radicals Y independently of one another represent hydrogen, hydroxyl, optionally substituted alkoxy, nitro or NH-A,
A represents hydrogen or optionally substituted alkyl or acyl,
R represents halogen, amino or optionally substituted alkyl, alkoxy, alkylmercapto, monoalkyl-, di-alkyl- or acyl-amino, cycloalkyl or aryl,
Hal represents chlorine or bromine,
n represents 0, 1, 2 or 3 and
r represents 0 or 1, with the proviso that there is not more than 1 acylamino group on a nucleus, and Y and NH-A do not simultaneously represent an acyl-amino group and an NH2 group, and the dyestuffs are fixed by heat treatment.
2. Process according to Claim 1, characterised in that dyestuffs of the general formula
wherein
X1 represents a direct bond, CO, SO2, a C,-C4-alkylene group which is optionally substituted by hydroxyl or a C4-C6-alkylene bridge which is interrupted by oxygen,
the radicals Y1 independently of one another represent hydrogen, hydroxyl, C1-C4-alkoxy, nitro or NH-A1,
A1 represents hydrogen, C1-C4-alkyl, C1-C4-alkyl-carbonyl or -sulphonyl, benzoyl or phenylsulphonyl,
R1 represents chlorine, bromine, amino, C1-C8-alkyl, C,-C4-alkoxy, C,-C4-alkylmercapto, monoor di-C1-C4-alkylamino, C1-C4-alkyl-carbonylamino or -sulphonylamino, benzoylamino, phenylsulphonylamino, cyclohexyl or phenyl,
Hal represents chlorine or bromine,
n, represents 0 or 1 and
r represents 0 to 1, and wherein the alkyl, alkoxy, phenyl and cyclohexyl radicals can be substituted by fluorine, chlorine, bromine, hydroxyl, C,-C4-alkoxy, cyano, C,-C,-alkoxycarbonyl, amino or mono- or di-C,
C4-alkylamino and the phenyl and cyclohexyl radicals can additionally be substituted by C,-C4alkyl, and wherein Y, and NH-A, are not simultaneously present as the C,-C4-alkylcarbonylamino or benzoylamino group and the NH2 group, are used.
3. Process according to Claims 1 and 2, characterised in that dyestuffs of the formula
wherein
A2 represents hydrogen or C,-C4-alkyl and Y1, Hal, R1, r and n, have the meaning indicated in Claim 2, are used.
4. Process according to Claims 1 to 3, characterised in that dyestuffs wherein either
Y or Y, independently of one another represent
hydrogen, hydroxyl, amino or methoxy, or
one Y or Y, represents hydrogen and
the other Y or Y, represents hydroxyl, amino, methoxy or nitro, are used.
5. Process according to Claims 1 to 4, characterised in that dyestuffs wherein
n or n, represents 0 or 1 and
R or R, represents chlorine, bromine, C1-C4-alkyl or C,-C2-alkoxy, are used.
6. Process according to Claims 1 to 5, characterised in that dyestuffs wherein
both Y and Y, represent hydroxyl, are used.
7. Process according to Claims 1 to 6, characterised in that dyestuffs wherein
A, A, or A2 represents hydrogen or branched C3- or C4-alkyl, are used.
8. Process according to Claims 1 to 7, characterised in that dyestuffs of the formula
Y3 = HorOH
W = H or CH3, are used.
9. Formulation for dyeing and printing cellulose fibres which have been swollen with watermiscible swelling agents or mixed fibres containing these fibres, characterised in that they contain a dyestuff of the general formula
wherein
X represents a direct bond, CO-, SO2- or an alkylene group which is optionally substituted or interrupted by oxygen,
the radical Y independently of one another represent hydrogen, hydroxyl, optionally substituted alkoxy, nitro or NH-A,
A represents hydrogen or optionally substituted C,-C4-alkyl or acyl,
R represents halogen, amino or optionally substituted alkyl, alkoxy, alkylmercapto, monoalkyl-, di-alkyl- or acyl-amino, cycloalkyl or aryl,
Hal represents chlorine or bromine,
n represents 0, 1, 2 or 3 and
r represents 0 or 1, with the proviso that there is not more than 1 acylamino group on a nucleus, and Y and NH-A do not simultaneously represent an acyl-amino group and an NH2 group.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782843474 DE2843474A1 (en) | 1978-10-05 | 1978-10-05 | METHOD FOR DYEING AND PRINTING CELLULOSE FIBERS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2034358A true GB2034358A (en) | 1980-06-04 |
Family
ID=6051490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7934181A Withdrawn GB2034358A (en) | 1978-10-05 | 1979-10-02 | Process for dyeing and printing cellulose fibres |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5551881A (en) |
| DE (1) | DE2843474A1 (en) |
| FR (1) | FR2438111A1 (en) |
| GB (1) | GB2034358A (en) |
| IT (1) | IT7926244A0 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100408640C (en) * | 2002-03-22 | 2008-08-06 | 西巴特殊化学品控股有限公司 | Anthraquinone dyes |
-
1978
- 1978-10-05 DE DE19782843474 patent/DE2843474A1/en not_active Withdrawn
-
1979
- 1979-10-02 GB GB7934181A patent/GB2034358A/en not_active Withdrawn
- 1979-10-03 IT IT7926244A patent/IT7926244A0/en unknown
- 1979-10-04 FR FR7924716A patent/FR2438111A1/en not_active Withdrawn
- 1979-10-04 JP JP12744179A patent/JPS5551881A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100408640C (en) * | 2002-03-22 | 2008-08-06 | 西巴特殊化学品控股有限公司 | Anthraquinone dyes |
| US7456316B2 (en) | 2002-03-22 | 2008-11-25 | Huntsman International Llc | Anthraquinone dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5551881A (en) | 1980-04-15 |
| FR2438111A1 (en) | 1980-04-30 |
| DE2843474A1 (en) | 1980-04-17 |
| IT7926244A0 (en) | 1979-10-03 |
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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) |