EP0012935B1 - Procédé de teinture et d'impression de matières textiles avec des colorants de dispersion - Google Patents
Procédé de teinture et d'impression de matières textiles avec des colorants de dispersion Download PDFInfo
- Publication number
- EP0012935B1 EP0012935B1 EP79105107A EP79105107A EP0012935B1 EP 0012935 B1 EP0012935 B1 EP 0012935B1 EP 79105107 A EP79105107 A EP 79105107A EP 79105107 A EP79105107 A EP 79105107A EP 0012935 B1 EP0012935 B1 EP 0012935B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dye
- ethylene oxide
- mol
- weight
- parts
- 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.)
- Expired
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- 238000004043 dyeing Methods 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 15
- 239000004753 textile Substances 0.000 title claims description 15
- 239000000986 disperse dye Substances 0.000 title claims description 12
- 239000000975 dye Substances 0.000 claims description 59
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 37
- 230000008961 swelling Effects 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 27
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 23
- 229920001223 polyethylene glycol Polymers 0.000 claims description 19
- 239000002202 Polyethylene glycol Substances 0.000 claims description 14
- 239000000835 fiber Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000012209 synthetic fiber Substances 0.000 claims description 9
- 229920002994 synthetic fiber Polymers 0.000 claims description 9
- 239000011877 solvent mixture Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 229920001400 block copolymer Polymers 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 description 21
- 239000004744 fabric Substances 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 10
- 229920003043 Cellulose fiber Polymers 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 229920005682 EO-PO block copolymer Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- -1 hydroxyethyl group Chemical group 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000001048 orange dye Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- GQEKAPMWKCXNCF-UHFFFAOYSA-N 2,2-bis(ethenyl)-1,4-dioxane Chemical compound C=CC1(C=C)COCCO1 GQEKAPMWKCXNCF-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- NNAVBEAARXTLEG-UHFFFAOYSA-N 2-(10-methylundecyl)phenol Chemical compound CC(C)CCCCCCCCCC1=CC=CC=C1O NNAVBEAARXTLEG-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- UZVAZDQMPUOHKP-UHFFFAOYSA-N 2-(7-methyloctyl)phenol Chemical compound CC(C)CCCCCCC1=CC=CC=C1O UZVAZDQMPUOHKP-UHFFFAOYSA-N 0.000 description 1
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- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
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- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-M sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000005809 transesterification reaction 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/6033—Natural or regenerated cellulose using dispersed dyes
-
- 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
-
- 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
Definitions
- the invention is therefore based on the object of a process for dyeing and printing textiles from cellulose fibers or mixtures of cellulose fibers and synthetic fibers with disperse dyes in an aqueous medium in the presence of water-soluble swelling and dye solvents and fixing the dyes by heating the dyed or printed textiles To provide temperatures up to 230 ° C, at which the fog formation during fixation is largely suppressed and which also results in good colorations.
- mono- and diether of polyethylene glycols or ethylene oxide-propylene oxide block copolymers are suitable as component (a) of the swelling and dye-solvent mixture.
- These compounds are made by reacting mono- or polyhydric alcohols or phenols with ethylene oxide.
- Suitable alcohols are, for example, methanol, ethanol, propanol, butanol, hexanol, decanol and dodecanol, polyhydric alcohols, such as ethylene glycol, glycerol, trimethylolpropane, pentaerythritol and sorbitol.
- the alcohols can also be reacted with a mixed gas of ethylene oxide and propylene oxide.
- Suitable phenols are, for example, the unsubstituted phenol, the isomeric methylphenols, bisphenol-A, 2,5-dimethylphenol, 2,4-dimethylphenol, o-phenylphenol and p-chlorophenol, isooctylphenol, isononylphenol, isododecylphenol, p-tert. Butylphenol and the corresponding diisoalkylphenols.
- carboxylic acid esters of polyethylene glycols and block copolymers of the type described above are also suitable as component (a) of the dye solvents.
- the carboxylic acid polyglycol esters are produced, for example, by, for example, a carboxylic acid ester of a C 2 7 to C 2O carboxylic acid with, for example, a C 1 to C 4 Alcohol is subjected to a transesterification reaction with a polyalkylene oxide.
- Suitable carboxylic acids are both saturated carboxylic acids, such as acetic acid, propionic acid, palmitic acid and stearic acid, and unsaturated carboxylic acids, such as acrylic acid, methacrylic acid, maleic acid and oleic acid.
- boric acid esters are also suitable, which are obtained, for example, by esterification of polyethylene glycol or block copolymers of ethylene oxide and propylene oxide with boric acid in a molar ratio of 0.5: 1 to 3: 1.
- Suitable boric acid esters can also be obtained by esterifying monoethers of polyethylene glycols with boric acid.
- C 1 to Cg monohydric alcohols, C 2 to C a diols, glycerol, trimethylolpropane, pentaerythritol and sorbitol can be reacted with ethylene oxide, 1 to 20 ethylene oxide units being added per hydroxyl group of the alcohol.
- a mixed gas of ethylene oxide and propylene oxide can also be used to produce the oxyethylation products, so that statistical copolymers are obtained.
- monoethers can also be prepared in which propylene oxide and ethylene oxide units are present as blocks. These monoethers are then esterified with boric acid in a known manner.
- Polyalkoxylated amines with a degree of alkoxylation of at least 3 are used as component (b) of the source and dye solvent mixture.
- Compounds of this type are known, they are prepared, for example, by reacting amines with ethylene oxide or propylene oxide.
- the amines which are subjected to the alkoxylation contain at least one N-H group or functional groups which are amenable to the alkoxylation reaction, e.g. a hydroxyethyl group as in triethanolamine.
- the suitable amines contain at least one carbon atom and at least one basic nitrogen atom. Both mono-, di- and polyamines can be used, e.g.
- the amines in question are either reacted with ethylene oxide alone, specifically with 3 to 100, preferably 8 to 50, moles of ethylene oxide or initially 3 to 100 moles of propylene oxide are added and this reaction product is then allowed to react with 3 to 200 moles of ethylene oxide.
- a 3 to 100-fold ethoxylated amine can also be reacted with 4 to 100 mol of propylene oxide and then with 3 to 100 mol of ethylene oxide.
- block polymers of the formulas A-B-A or B-A-B are obtained, in which A is 3 to 100 ethylene oxide units and B is 3 to 100 propylene oxide units.
- water-soluble products which are a swelling agent for the cellulose and a dye solvent for the water-insoluble disperse dye.
- cellulose fibers or mixtures of cellulose fibers are dyed or printed with synthetic fibers.
- the cellulose fibers are swellable in water, for example cotton and fibers made from regenerated cellulose are suitable, which are accessible for water and the solvent mixture.
- polyester fibers are primarily used as synthetic fibers.
- cellulose triacetate, cellulose acetate and polyamide fibers are suitable as synthetic fibers.
- the proportion of synthetic fibers in the fiber mixture can vary within a wide range, for example fiber mixtures containing 80 to 20% by weight of synthetic fibers can be used.
- textile materials made of polyester and cotton are preferably dyed or printed. Textile materials are to be understood as ridges, non-woven fabrics, yarns, threads, knitted hoses, piece goods, fabrics and carpets.
- cellulose fibers and synthetic fibers are dyed or printed with a single class of dyes, namely with disperse dyes.
- the disperse dyes can, for example, belong to the following classes of dyes: dyes with one or more azo bonds, anthraquinone dyes, indigo dyes and phthalocyanine dyes.
- the dyes are converted into a finely divided preparation with the addition of anionic or nonionic dispersants.
- the preparation can be used as a liquid formulation or in powder form.
- the pure dye content is usually between 10 and 90%.
- disperse dyes those are particularly preferred which are insoluble in water at a temperature of 100 ° C. and below and readily soluble in the solvent used at the fixing temperature.
- the coloring is carried out according to the invention in an aqueous medium.
- textile material is impregnated, for example, with a padding liquor which contains 30 to 250 parts by weight of the swelling and dye-solvent mixture from components (a) and (b) and 1 to 200 parts by weight of 20% preparations of the disperse dyes per 1,000 parts by weight of liquor.
- Printing pastes are used for printing, which differ from the dyeing liquors in that they contain a thickener in high concentration.
- Suitable thickeners are the commonly used starch ethers, alginates, tragacanth and core flour ether, as well as synthetic thickeners based on high molecular weight polymers of ethylenically unsaturated carboxylic acids with 3 to 5 carbon atoms. These are primarily polymers of acrylic acid, methacrylic acid, maleic acid, maleic anhydride, fumaric acid and itaconic acid, and copolymers of the carboxylic acids mentioned.
- the carboxylic acids may also with other copolymerizable ethylenically unsaturated monomers such as ethylene, Vinylestern, Acrylklareestern, methacrylic esters, styrene, vinyl ethers and amides of ethylenically unsaturated C 3 - to C s -carboxylic acids are copolymerized.
- This group of copolymers contains at least 40, preferably 75 to 99.9% by weight of ethylenically unsaturated carboxylic acids.
- the synthetic thickeners have a high molecular weight.
- Particularly suitable synthetic thickeners are obtained if the above-mentioned ethylenically unsaturated carboxylic acids are copolymerized with monomers which contain two ethylenically unsaturated double bonds, for example butadiene, divinylbenzene, butanediol diacrylate, divinyldioxane or diallyl phthalate. These monomers make up approximately 0.05 to 5% by weight of the high molecular weight copolymers. 1,000 parts by weight of the printing paste generally contain 10 to 80 parts by weight of a synthetic or natural thickener.
- Dyeing is carried out, for example, by padding the textiles with a dyeing liquor, the liquor absorption being in the range from 25 to 120%.
- the material is usually dried at temperatures from 90 to 120 ° C. and then fixed at temperatures from 180 to 230, preferably with hot air at 210 to 220 ° C. It is fixed, for example, in the stenter, on the hot flue or on screen drum systems. About 15 to 120, preferably 45 to 90 seconds are required for the fixation. Superheated steam at 180 to 190 ° C. can also be used.
- the fixing time should be extended to 5 to 10 minutes. In the case of fiber mixtures, a tone-on-tone colored textile material is obtained which can be rinsed cold and warm and washed with commercially available detergents. Although the fixation of the dyes takes place at relatively high temperatures, surprisingly no or only very slight fog formation is observed as a result of evaporating swelling and dye solvents.
- the fixing yield is very good and dyeings with good wash and rub fastness are obtained
- the padding liquors and printing pastes can also contain the usual additives, such as pH regulators, anti-migration agents, anti-freezing agents, emulsifiers, dispersants, leveling agents, fixing accelerators and foam dampers.
- the dyed or printed fabric is rinsed and subjected to a post-wash at cooking temperature, at which conventional detergents can be used.
- the invention is illustrated by the following examples.
- the parts given in the examples are parts by weight, the percentages are percentages by weight.
- a fabric made of 65 parts of polyester fibers and 35 parts of mercerized cotton was impregnated with a liquor containing 5 g / l of a 20% preparation of the brown, water-insoluble disperse dye of the formula and 80 g / l of one of the swelling and dye solvents 1) to 14) given below or mixtures thereof (see table).
- the pH of the liquors was adjusted to 6 using glutaric acid.
- the liquor absorption of the fabric was 50%.
- the tissue pieces were then dried at a temperature of 120 ° C. for 60 seconds and then fixed in a laboratory dryer at 215 ° C. for 60 seconds.
- the fabric was then rinsed cold and warm and washed for 5 minutes at 100 ° C. in the presence of a commercially available detergent.
- the fabric pieces were weighed in an air-conditioned state before impregnation, after intermediate drying and after treatment at 215 ° C. From the values found, the percentage of the solvent applied which evaporated during the heat treatment was determined.
- a fabric made of 65 parts of polyester fiber and 35 parts of mercerized cotton is impregnated with a liquor containing 10 g / l of a 20% liquid preparation of the red water-insoluble disperse dye of the formula and 80 g / l of a swelling and dye solvent from a mixture of 3 parts of polyethylene glycol with a molecular weight of 1,500 and 1 part of a reaction product of 1 mol of neopentanediamine and 15.6 mol of ethylene oxide.
- the pH of the padding liquor is adjusted to 6 with glutaric acid.
- the fabric is impregnated with the padding liquor, with the liquor absorption being 45%.
- the fabric is then dried for 60 seconds at a temperature of 120 ° C and fixed for 90 seconds at 225 ° C in a continuously working laboratory dryer. Then it is rinsed cold and warm and washed for 5 minutes at 100 ° C in the presence of a commercially available detergent. The dye is almost completely fixed on the fabric. A red color is obtained with good fastness to washing and rubbing.
- the textile material specified in Example 1 is impregnated with a dyeing liquor which comprises 20 g / l of a 20% preparation of the dye of the formula I (Example 1) and 60 g / l of a mixture of 1 part of a reaction product as swelling and dye solvent Contains 1 mole of i-octylphenol and 14 moles of ethylene oxide and 2 parts of a reaction product of 1 mole of piperazine and 16 moles of ethylene oxide.
- the pH of the liquor was adjusted to 6 using glutaric acid.
- the fleet uptake was 50%.
- the fabric was dried at a temperature of 120 ° C for 60 seconds and then heated to a temperature of 225 ° C in a continuous laboratory dryer for 30 seconds to fix the dye.
- the coloring was completed as described in Example 2. A light brown color with good fastness properties was obtained.
- the washout loss was very low.
- the weight loss of the tissue sample after fixation was no higher than in a comparison test in which the liquor probably contained the dye preparation but did not
- the textile material mentioned in Example 1 was impregnated with a dyeing liquor containing 100 g / l of a 20% preparation of the blue dye of the formula and as the swelling and dyeing solvent contained 100 g / l of a mixture of 95 parts of an addition product of 1 mol of methyl acrylate and 1 mol of polyethylene glycol with a molecular weight of 400 (alkoxypropionic acid derivative) and 5 parts of a reaction product of 1 mol of aniline with 10 mol of ethylene oxide.
- the pH of the liquor was adjusted to 6 using citric acid.
- the fleet uptake was 50%.
- the fabric was dried for 60 seconds at a temperature of 120 ° C. and then heated for 90 seconds to 220 ° C. in a continuously operating laboratory dryer to fix the dye.
- the amount of solvent evaporated was less than when using the alkoxypropionic acid derivative alone, it was about 5%.
- the coloring is completed according to the instructions given in Example 2. A deep blue color is obtained with good light and wet fastness properties. The washout loss is very low.
- Example 1 The textile material specified in Example 1 is impregnated with a dye liquor containing 80 g / l of dye I (see Example 1) and solvent 80 g / l of a mixture of 80 parts as swelling and dyeing solvent contains a polyethylene glycol with a molecular weight of 1,500 and 20 parts of a reaction product of 1 mol of hexamethylenediamine and 15 mol of ethylene oxide.
- the pH of the liquor was adjusted to 5 with citric acid.
- the fleet uptake was 50%.
- the fabric was dried for 60 seconds at a temperature of 120 ° C. and heated in a laboratory dryer for 60 seconds at a temperature of 215 ° C. to fix the dye.
- the coloring is completed as described in Example 2. With less wash-out loss, a dark red-brown color is obtained with good fastness to washing, light and rubbing. Virtually no solvent evaporated during the fixing process.
- a fabric made from a fiber mixture of 50 parts of polyester fibers and 50 parts of cotton is impregnated with an aqueous liquor containing 20 g / l of a 20% preparation of the dye of the formula and contains 50 g / l of a mixture of 80 parts of a polyethylene glycol with a molecular weight of -600 and 20 parts of a reaction product of 1 mol of triethanolamine and 14 mol of ethylene oxide as swelling and dye solvent.
- the pH of the liquor was adjusted to 7 with glutaric acid.
- the fleet uptake was 52%.
- the textile material was dried at 120 ° C. for 60 seconds and then heated in a laboratory drying unit at 210 ° C. for 90 seconds. The coloring was then completed as indicated in Example 2. You got very little.
- a mercerized cotton twill is impregnated with a dye liquor which contains 20 g / l of the water-insoluble dye of the formula 11 (see Example 2) and 120 g / l of swelling and dye solution mixture which comprises 90 parts of a reaction product of 1 mol of pentaerythritol and 7 mol Ethylene oxide and 10 parts of a reaction product of 1 mole of butylamine and 14 moles of ethylene oxide.
- the pH of the liquor was adjusted to 6 using glutaric acid.
- the fleet uptake was 53%.
- the fabric was dried for 60 seconds at a temperature of 120 ° C. and heated in a laboratory dryer for 60 seconds at a temperature of 200 ° C. to fix the dye.
- the coloring is completed according to the procedure given in Example 2.
- a bright red color with good wet and rub fastness properties is obtained without significant washout losses.
- a mercerized cotton twill was impregnated with an aqueous dye liquor containing 80 g / l of dye (IV) (see Example 6) and 200 g of a mixture of 80 parts of a polyethylene glycol with a molecular weight of 800 and 20 parts of a block polymer of 1 mol Contained ethylenediamine, 8 moles of propylene oxide and 8 moles of ethylene oxide.
- the pH of the liquor was adjusted to 6 using citric acid.
- the fleet uptake was 52%.
- the fabric was then dried as usual at 120 ° C. and fixed in a laboratory dryer at 215 ° C. for 30 seconds. Virtually no solvent evaporated during the fixing process. After rinsing and washing, a brilliant, intense gold-orange coloration with good fastness properties was obtained with very little loss of dye.
- a fabric made of 67 parts of polyester fiber and 33 parts of cotton (mercerized) was impregnated with a liquor which reacted with 100 g / l of a mixture of 80 parts of a boric acid ester of polyethylene glycol (molecular weight about 800) in a molar ratio of 1: 3 and 20 parts of ethylenediamine 35 moles Ethylene oxide.
- the fleet uptake was 80%.
- the mixture was then dried at 60 to 70 ° C for 15 minutes.
- the mixture was dried at 130 ° C. for 2 minutes and treated with hot air at 210 ° C. for 90 seconds, rinsed cold and warm, hot soaped and rinsed cold. No solvent mist was observed during the heat treatment.
- Example 9 was repeated, but instead of dye II with 50 parts of the red-orange dye of the formula
- a fabric made of polyester / cotton (in a weight ratio of 67:33) is printed with the following printing paste:
- Example 9 After printing, drying is carried out as described in Example 9, treated with superheated steam for 4 minutes at 190 ° C., rinsed, soaped and rinsed.
- Example 4 was repeated, except that instead of the blue dye of formula 111, the same amount of the brown-yellow dye of the formula has been used. In this case too, the proportion of the swelling and dye solvent evaporated during fixing was approx. 5%.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT79105107T ATE330T1 (de) | 1978-12-21 | 1979-12-12 | Verfahren zum faerben und bedrucken von textilien mit dispersionsfarbstoffen. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19782855188 DE2855188A1 (de) | 1978-12-21 | 1978-12-21 | Verfahren zum faerben und bedrucken von textilien mit dispersionsfarbstoffen |
DE2855188 | 1978-12-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0012935A1 EP0012935A1 (fr) | 1980-07-09 |
EP0012935B1 true EP0012935B1 (fr) | 1981-10-21 |
Family
ID=6057828
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP79105107A Expired EP0012935B1 (fr) | 1978-12-21 | 1979-12-12 | Procédé de teinture et d'impression de matières textiles avec des colorants de dispersion |
Country Status (10)
Country | Link |
---|---|
US (1) | US4239491A (fr) |
EP (1) | EP0012935B1 (fr) |
AR (1) | AR217977A1 (fr) |
AT (1) | ATE330T1 (fr) |
BR (1) | BR7908271A (fr) |
CA (1) | CA1135011A (fr) |
DE (2) | DE2855188A1 (fr) |
ES (1) | ES487122A1 (fr) |
IL (1) | IL58975A (fr) |
PT (1) | PT70505A (fr) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2901823C2 (de) * | 1979-01-18 | 1983-12-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zum Bedrucken von textilen Materialien |
DE2930334A1 (de) | 1979-07-26 | 1981-02-19 | Basf Ag | Disazofarbstoffe mit heterocyclischen kupplungskomponenten |
DE2948456A1 (de) | 1979-12-01 | 1981-06-11 | Basf Ag, 6700 Ludwigshafen | Disazofarbstoffe |
GB2259525B (en) * | 1991-09-11 | 1995-06-28 | Ciba Geigy Ag | Process for dyeing cellulosic textile material with disperse dyes |
US5904738A (en) * | 1998-01-28 | 1999-05-18 | Crompton & Knowles Corporation | Gas-fade inhibition |
DE19815129A1 (de) * | 1998-04-03 | 1999-10-07 | Basf Ag | Präzipitierte, wasserunlösliche Farbstoffe in kolloid-disperser Form |
US6497733B1 (en) * | 2000-04-03 | 2002-12-24 | Nano-Tex, Llc | Dye fixatives |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH586319B5 (fr) * | 1968-11-25 | 1977-03-31 | Du Pont | |
US3656880A (en) * | 1969-11-25 | 1972-04-18 | Du Pont | Uniformly dyed blue or turquoise water swellable cellulosic fibers |
US3711245A (en) * | 1970-09-18 | 1973-01-16 | Du Pont | Liquid for pad-bath dyeing containing glycol compound and boric acid or borax |
US3706525A (en) * | 1971-03-08 | 1972-12-19 | Du Pont | Water swollen cellulose dyeing with high molecular weight disperse dye in a glycol ether solution |
US3888624A (en) * | 1971-03-08 | 1975-06-10 | Du Pont | Process for dyeing water swellable cellulosic materials with polypropylene glycols |
DE2643804A1 (de) * | 1975-06-27 | 1978-04-06 | Basf Ag | Verfahren zum faerben und bedrucken von cellulose-fasern oder gemischen von cellulose-fasern mit synthetischen fasern |
DE2528743C2 (de) * | 1975-06-27 | 1982-06-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zum Färben und Bedrucken von Cellulose-Fasern oder Gemischen von Cellulose-Fasern mit synthetischen Fasern |
GB1559627A (en) * | 1976-04-17 | 1980-01-23 | Bayer Ag | Process for dyeing sheets or sheet like structures |
DE2636427C3 (de) * | 1976-08-13 | 1980-07-31 | Basf Ag, 6700 Ludwigshafen | Farbstoffzubereitungen für Cellulose oder cellulosehaltiges Fasermaterial |
DE2751830A1 (de) | 1977-02-01 | 1978-08-03 | Sandoz Ag | Verfahren zum faerben und bedrucken von zellulosefasern enthaltenden geweben |
-
1978
- 1978-12-21 DE DE19782855188 patent/DE2855188A1/de not_active Withdrawn
-
1979
- 1979-11-27 PT PT70505A patent/PT70505A/fr unknown
- 1979-12-12 EP EP79105107A patent/EP0012935B1/fr not_active Expired
- 1979-12-12 AT AT79105107T patent/ATE330T1/de not_active IP Right Cessation
- 1979-12-12 US US06/103,074 patent/US4239491A/en not_active Expired - Lifetime
- 1979-12-12 DE DE7979105107T patent/DE2961085D1/de not_active Expired
- 1979-12-17 CA CA000342082A patent/CA1135011A/fr not_active Expired
- 1979-12-17 IL IL58975A patent/IL58975A/xx unknown
- 1979-12-17 BR BR7908271A patent/BR7908271A/pt unknown
- 1979-12-20 AR AR279402A patent/AR217977A1/es active
- 1979-12-20 ES ES487122A patent/ES487122A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AR217977A1 (es) | 1980-04-30 |
ATE330T1 (de) | 1981-11-15 |
CA1135011A (fr) | 1982-11-09 |
US4239491A (en) | 1980-12-16 |
IL58975A0 (en) | 1980-03-31 |
DE2961085D1 (en) | 1981-12-24 |
DE2855188A1 (de) | 1980-07-10 |
ES487122A1 (es) | 1980-09-16 |
IL58975A (en) | 1982-08-31 |
BR7908271A (pt) | 1980-07-22 |
EP0012935A1 (fr) | 1980-07-09 |
PT70505A (fr) | 1979-12-01 |
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