US3311444A - Dyeing or printing synthetic polyamide textile material - Google Patents
Dyeing or printing synthetic polyamide textile material Download PDFInfo
- Publication number
- US3311444A US3311444A US418907A US41890764A US3311444A US 3311444 A US3311444 A US 3311444A US 418907 A US418907 A US 418907A US 41890764 A US41890764 A US 41890764A US 3311444 A US3311444 A US 3311444A
- Authority
- US
- United States
- Prior art keywords
- parts
- textile material
- dyeing
- synthetic polyamide
- polyamide textile
- 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 - Lifetime
Links
- 239000000463 material Substances 0.000 title claims description 25
- 238000004043 dyeing Methods 0.000 title claims description 15
- 239000004753 textile Substances 0.000 title claims description 15
- 239000004952 Polyamide Substances 0.000 title claims description 10
- 229920002647 polyamide Polymers 0.000 title claims description 10
- RQNVIKXOOKXAJQ-UHFFFAOYSA-N naphthazarin Chemical compound O=C1C=CC(=O)C2=C1C(O)=CC=C2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 11
- 239000000975 dye Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 244000144992 flock Species 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- -1 polyhexamethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- C09B13/00—Oxyketone dyes
- C09B13/02—Oxyketone dyes of the naphthalene series, e.g. naphthazarin
-
- 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
- D06P1/0048—Converting dyes in situ in a non-appropriate form by hydrolysis, saponification, reduction with split-off of a substituent
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/907—Nonionic emulsifiers for dyeing
Definitions
- This invention relates to a method of dyeing or printing synthetic polyamide textile material in fast black shades and to synthetic p-olyamide textile material which has been dyed black using 5,8-dihydroxy-1,4-naphthoquinone.
- Dyeing of synthetic polyamide textile material in fast black shades usually offers difficulty because hardly any unitary dyes are available. As a rule it is necessary to use dye mixtures the individual components of which often exhibit unequal affinity and which in many cases have only unsatisfactory fastness properties. There is therefore a demand for a method by means of which very fast black dyeings or prints can be obtained on textile material of synthetic polyamides in a simple way.
- synthetic polyamide textile material is dyed a very fast black by treating the said material at temperatures of from 90 to 220 C. with 5,8-dihydroxy-1,4-naphthoquinone.
- This treatment is carried out by conventional methods of application, for example with dye liquors or print pastes.
- textile material examples include fibers, filaments, threads, flock, Woven cloth and knitted cloth.
- polyamides are those obtained by polymerization of epsilon-caprolactam, omega-undecanic acid or hexamethylene diamine with adipic acid or which contain such polymers.
- Dyeings or prints in black shades having good fastness are obtained on the said textile material according to the new process.
- the black dyeings are distinguished by good fastness to light and rubbing and very good wet fastness properties.
- naphthazarin 5,8-dihydroxy-1,4-naphthoquinone has already been proposed as a mordant dye for vegetable fibers or for W001, but this compound has not been able to achieve any technical importance (Helvetica Chimica Acta, volume XXVI, part I (1943), 92). Since according to the prior art method, naphthazarin would only go onto the fiber if the material had been rnordanted with metal salts, such as aluminum salts or calcium salts, it could not have been expected that such good and fast dyeings would be obtained with naphthazarin on polyamide textile material Without metal mordants.
- metal salts such as aluminum salts or calcium salts
- the naphthazarin may be used in a form which has been made soluble, for example by sodium bisulfite, or preferably in finely divided form.
- Dyeing of synthetic textile material is generally carried out in weakly alkaline to strongly acid aqueous liquors, but preferably in neutral to acid liquors and advantageously at temperatures of from 90 to 125 C.
- the procedure may however also be that the textile material -is impregnated with an aqueous liquor containing the dye, and the impregnated material is squeezed, dried and heated for a short period at temperatures of from about 140 to 220 C.
- the dye liquor may have the usual dyeing auxiliaries, for example levelling agents or surfactants, added to it.
- dye liquors may be used which contain, in 1000 parts, 0.1 to 50 parts of finely divided or solu;
- bilized dye 0.05 to 10 parts of a conventional dyeing auxiliary, for example the reaction product of 1 mole of sperm oil alcohol and moles of ethylene oxide, 0.5 to 5 parts of an acid, such as formic acid or acetic acid, and 900 to 995 parts of water.
- a conventional dyeing auxiliary for example the reaction product of 1 mole of sperm oil alcohol and moles of ethylene oxide, 0.5 to 5 parts of an acid, such as formic acid or acetic acid, and 900 to 995 parts of water.
- print pastes containing as a rule in 1000 parts, 1 to 150 parts of naphthazarin in finely divided or solubilized form, 200 to 650 parts of a conventional thickener, for example crystal gum, if necessary 1 to 50 parts of a conventional printing auxiliary, for example resorcinol, and 250 to 800 parts of water.
- a conventional thickener for example crystal gum
- resorcinol for example resorcinol
- Example 1 A polyhexamethylene diamine adipate cloth is printed with a paste consisting of 70 parts of finely divided naphthazarin, 600 parts of a crystal gum thickening (1:1) and 330 parts of water. The printed cloth is dried and steamed for thirty minutes. The black print obtained has good light fastness and has very good wet fastness properties.
- Example 2 100 parts of polycaprolactam flock is dyed for ninety minutes at to C. in a liquor consiting of 3000 parts of water, 5 parts of finely divided naphthazarin, 2.5 parts of the reaction product of 1 mole of castor oil and 40 parts of ethylene oxide, and 2 parts of 30% aqueous acetic acid.
- the black dyeing obtained has good fastness to light and very good wet fastness.
- a process for dyeing and printing textile material of synthetic polyamides which comprises contacting said material with 5,8-dihydroxy-1,4-naphthoquinone at temperatures from 90 to 220 C.
- a process as claimed in claim 1 wherein there is applied to said textile material a printing paste containing about 1 to parts of 5,8-dihydroxy-1,4-naphth0quinone per 1000 parts of paste, and the material is then dried and treated with steam.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB74717A DE1259833B (de) | 1963-12-18 | 1963-12-18 | Verwendung von Naphthazarin zum Faerben und Bedrucken von synthetischem Textilmaterial |
Publications (1)
Publication Number | Publication Date |
---|---|
US3311444A true US3311444A (en) | 1967-03-28 |
Family
ID=6978365
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US418907A Expired - Lifetime US3311444A (en) | 1963-12-18 | 1964-12-16 | Dyeing or printing synthetic polyamide textile material |
Country Status (9)
Country | Link |
---|---|
US (1) | US3311444A (de) |
AT (1) | AT250286B (de) |
BE (1) | BE657248A (de) |
CH (1) | CH417525A (de) |
DE (1) | DE1259833B (de) |
DK (1) | DK112725B (de) |
FR (1) | FR1417802A (de) |
GB (1) | GB1081438A (de) |
NL (1) | NL6414594A (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992001022A1 (fr) * | 1990-07-11 | 1992-01-23 | Ihara Chemical Industry Co., Ltd. | Procede de fabrication de colorant noir, produit cosmetique contenant ledit colorant noir et procede d'application |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2687939A (en) * | 1954-08-31 | Organic compounds useful as dye |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2365809A (en) * | 1940-06-29 | 1944-12-26 | Celanese Corp | Mordant dyeing of cellulose derivatives |
CH323364A (de) * | 1953-10-30 | 1957-07-31 | Siemens Ag | Aus Strom- und Spannungswandler kombinierter Wandler. |
NL299439A (de) * | 1962-05-24 |
-
1963
- 1963-12-18 DE DEB74717A patent/DE1259833B/de active Pending
-
1964
- 1964-12-03 CH CH1561864A patent/CH417525A/de unknown
- 1964-12-15 NL NL6414594A patent/NL6414594A/xx unknown
- 1964-12-16 DK DK617964AA patent/DK112725B/da unknown
- 1964-12-16 US US418907A patent/US3311444A/en not_active Expired - Lifetime
- 1964-12-17 GB GB51329/64A patent/GB1081438A/en not_active Expired
- 1964-12-17 BE BE657248D patent/BE657248A/xx unknown
- 1964-12-18 FR FR999175A patent/FR1417802A/fr not_active Expired
- 1964-12-18 AT AT1074464A patent/AT250286B/de active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2687939A (en) * | 1954-08-31 | Organic compounds useful as dye |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992001022A1 (fr) * | 1990-07-11 | 1992-01-23 | Ihara Chemical Industry Co., Ltd. | Procede de fabrication de colorant noir, produit cosmetique contenant ledit colorant noir et procede d'application |
US5358538A (en) * | 1990-07-11 | 1994-10-25 | Ihara Chemical Industry Co., Ltd. | Process for production of black coloring material and cosmetics containing said black coloring material and use thereof |
Also Published As
Publication number | Publication date |
---|---|
CH1561864A4 (de) | 1966-03-31 |
CH417525A (de) | 1967-02-15 |
FR1417802A (fr) | 1965-11-12 |
BE657248A (de) | 1965-06-17 |
GB1081438A (en) | 1967-08-31 |
NL6414594A (de) | 1965-06-21 |
DE1259833B (de) | 1968-02-01 |
DK112725B (da) | 1969-01-13 |
AT250286B (de) | 1966-11-10 |
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