US2989361A - Dyeing process - Google Patents
Dyeing process Download PDFInfo
- Publication number
- US2989361A US2989361A US2989361DA US2989361A US 2989361 A US2989361 A US 2989361A US 2989361D A US2989361D A US 2989361DA US 2989361 A US2989361 A US 2989361A
- Authority
- US
- United States
- Prior art keywords
- quaternary ammonium
- benzyl
- urea
- dyeing
- gram
- 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
- 238000004043 dyeing Methods 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 24
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 26
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 16
- -1 VINYL COMPOUNDS Chemical class 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 150000002829 nitrogen Chemical group 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 24
- 125000002091 cationic group Chemical group 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000004202 carbamide Substances 0.000 description 12
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 229940027983 antiseptics and disinfectants Quaternary ammonium compounds Drugs 0.000 description 10
- 229940073608 benzyl chloride Drugs 0.000 description 10
- GKRZNOGGALENQJ-UHFFFAOYSA-N N-carbamoylacetamide Chemical compound CC(=O)NC(N)=O GKRZNOGGALENQJ-UHFFFAOYSA-N 0.000 description 8
- 229960000583 Acetic Acid Drugs 0.000 description 6
- SXPWTBGAZSPLHA-UHFFFAOYSA-M Cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atoms Chemical group C* 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 150000003672 ureas Chemical class 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 2
- QFFVPLLCYGOFPU-UHFFFAOYSA-N Barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 2
- 210000002370 ICC Anatomy 0.000 description 2
- RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical compound NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000979 synthetic dye Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
-
- 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
-
- 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
-
- 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/927—Polyacrylonitrile fiber
Definitions
- the present invention relates to a dyeing process; more particularly it concerns a process wherein articles of polyacrylonitrile, polyvinylidene-cyanide or co-polymers thereof with other vinyl compounds, are dyed with cationic dyestuffs in the presence of quaternary ammonium compounds containing a benzyl radical which may be substituted by halogen, and an alkyl radical having at least 8 carbon atoms. By the presence of the quaternary ammonium compounds the dyeing is effected in an excellent levelness.
- Suitable quaternary ammonium compounds are for example those which derive from fatty amines containing 8 to 18, preferably 12 to 16, carbon atoms, and are obtainable therefrom by the introduction of low molecular weight alkyl radicals such as methyl groups, and by the subsequent reaction with benzyl chloride or 3,4-dichlorobenzyl chloride.
- the quaternary ammonium compounds in the form of their addition products with urea or urea derivatives such as monoacetyl urea.
- Such addition products are obtainable for example by melting the quaternary ammonium compounds with urea or urea derivatives.
- Cationic dyestuffs which are suitable for the dyeing of articles from polyacrylonitrile, polyvinylidene-cyanide or co-polymers thereof with other vinyl compounds, are described for example in American Dyestuif Reporter 1954, pages 432433.
- the process of the invention enables articles produced from the aforesaid polymers such as filaments, fibres, fabrics and foils to be dyed with cationic dyestuffs substantially more level than would be possible in the presence of the hitherto proposed levelling agents.
- Example 1 Yarns of polyacrylonitrile fibres are introduced at 50 C. into a dyebath containing per litre 0.05 gram of the cationic dyestufi 0.2. gram of dimethyl-cetyl-benzyl-ammonium chloride, 0.25 gram of sodium acetate and 0.2 gram of glacial acetic acid, using a liquor-to-goods ratio of 40:1. The temperatures of the liquor is slowly raised from 50 C. to 9698 C. and the dyebath is kept at this temperature for 1 hour. A pale pink dyeing of excellent levelness is obtained.
- Example 2 A fabric of polyacrylonitrile filaments is introduced 2,989,361 Patented June 20, 1961 ICC 2 into 'a bath containing per litre 0.1 gram of the cationic dyestulf 0.15 gram of the quaternary ammonium compound obtainable by reaction of dimethyl palm kernel fatty amine with benzyl chloride, 0.2 gram of sodium acetate and 0.3 gram of glacial acetic acid, using a liquor-to-goods ratio of 40:1.
- the dyeing is started at 60 C., the temperature is slowly raised to 98 C. and the dyeing is completed at this temperature within 1 hour. An excellently level lemon-yellow dyeing is thus obtained.
- Example 3 Polyacrylonitrile fibres are introduced into a bath containing per litre 0.125 gram of the cationic dyestufif Example 4
- a fabric from polyacrylonitrile fibres is introduced at 60 C. into a bath containing per litre 0.1 gram of the cationic dyestuif of Example 1, 0.3 g. of the addition product described below, 0.3 gram of sodium acetate and 0.3 gram of glacial acetic acid, using a liquor-togoods ratio of 40:1.
- the temperature of the liquor is slowly raised from 60 to 98 C. and the bath is kept at this temperature for about 9 0 minutes. A completely level pink dyeing is obtained.
- the addition product employed is obtainable by melting 30 parts by weight of the quaternary ammonium compound, prepared by reacting dimethyl-palmkernel fatty amine with benzyl chloride, together with 55 parts by weight of urea and 15 parts by weight of monoacetyl urea.
- a process according to claim 1 which comprises applying said quaternary ammonium compound in form of its reaction product with a compound selected from the group consisting of urea and derivatives of urea.
- a process of claim 1 wherein the quaternary ammonium compound is dimethyl-cetyl-benzyl-ammonium chloride.
- a process of claim 1 wherein the quaternary ammonium compound is the reaction product of dimethylpalm-kernel fatty amine with benzyl chloride.
- leveling agent is the addition product of dimethyl-cetyl-benzyl-ammonium chloride, urea and monoacetyl urea.
- leveling agent is the addition product obtained by melting urea, monoacetyl urea and a quaternary ammonium compound obtained by reacting dimethyl-palmkernel fatty amine with benzyl chloride.
- Diserens The Chem. Tech. of Dyeing and Printing, vol. II, Reinhold Pub. Corp., N.Y., 1951, pp. 108, 327- 328.
- Venkataraman The Chem. of Synthetic Dyes, Academic Press Inc., 1952, N.Y., pp. 295, 879.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coloring (AREA)
Description
United StatesPatentO 2,989,361 DYEING PROCESS Walter Hees, Koln-Hohenberg, Germany, assignor to Farbenfabriken Bayer Aktiengesellschaft, Leverkusen,
Germany, a corporation of Germany 1 No Drawing. Filed Aug. 5, 1958, Ser. No. 753,201
Claims priority, application Germany Aug. 14, 1957 6 Claims. (Cl. 8-55) The present invention relates to a dyeing process; more particularly it concerns a process wherein articles of polyacrylonitrile, polyvinylidene-cyanide or co-polymers thereof with other vinyl compounds, are dyed with cationic dyestuffs in the presence of quaternary ammonium compounds containing a benzyl radical which may be substituted by halogen, and an alkyl radical having at least 8 carbon atoms. By the presence of the quaternary ammonium compounds the dyeing is effected in an excellent levelness.
Suitable quaternary ammonium compounds are for example those which derive from fatty amines containing 8 to 18, preferably 12 to 16, carbon atoms, and are obtainable therefrom by the introduction of low molecular weight alkyl radicals such as methyl groups, and by the subsequent reaction with benzyl chloride or 3,4-dichlorobenzyl chloride.
It has moreover been found that especially advantageous results are achieved by using the quaternary ammonium compounds in the form of their addition products with urea or urea derivatives such as monoacetyl urea. Such addition products are obtainable for example by melting the quaternary ammonium compounds with urea or urea derivatives.
The amount of the quaternary compounds or their urea addition products required in each case may easily be ascertained by preliminary tests; detailed explanations will be found in the following examples.
Cationic dyestuffs which are suitable for the dyeing of articles from polyacrylonitrile, polyvinylidene-cyanide or co-polymers thereof with other vinyl compounds, are described for example in American Dyestuif Reporter 1954, pages 432433.
The process of the invention enables articles produced from the aforesaid polymers such as filaments, fibres, fabrics and foils to be dyed with cationic dyestuffs substantially more level than would be possible in the presence of the hitherto proposed levelling agents.
The following examples serve to illustrate the invention without, however, limiting the scope thereof.
Example 1 Yarns of polyacrylonitrile fibres are introduced at 50 C. into a dyebath containing per litre 0.05 gram of the cationic dyestufi 0.2. gram of dimethyl-cetyl-benzyl-ammonium chloride, 0.25 gram of sodium acetate and 0.2 gram of glacial acetic acid, using a liquor-to-goods ratio of 40:1. The temperatures of the liquor is slowly raised from 50 C. to 9698 C. and the dyebath is kept at this temperature for 1 hour. A pale pink dyeing of excellent levelness is obtained.
Example 2 A fabric of polyacrylonitrile filaments is introduced 2,989,361 Patented June 20, 1961 ICC 2 into 'a bath containing per litre 0.1 gram of the cationic dyestulf 0.15 gram of the quaternary ammonium compound obtainable by reaction of dimethyl palm kernel fatty amine with benzyl chloride, 0.2 gram of sodium acetate and 0.3 gram of glacial acetic acid, using a liquor-to-goods ratio of 40:1. The dyeing is started at 60 C., the temperature is slowly raised to 98 C. and the dyeing is completed at this temperature within 1 hour. An excellently level lemon-yellow dyeing is thus obtained.
Example 3 Polyacrylonitrile fibres are introduced into a bath containing per litre 0.125 gram of the cationic dyestufif Example 4 A fabric from polyacrylonitrile fibres is introduced at 60 C. into a bath containing per litre 0.1 gram of the cationic dyestuif of Example 1, 0.3 g. of the addition product described below, 0.3 gram of sodium acetate and 0.3 gram of glacial acetic acid, using a liquor-togoods ratio of 40:1. The temperature of the liquor is slowly raised from 60 to 98 C. and the bath is kept at this temperature for about 9 0 minutes. A completely level pink dyeing is obtained.
The addition product employed is obtainable by melting 30 parts by weight of the quaternary ammonium compound, prepared by reacting dimethyl-palmkernel fatty amine with benzyl chloride, together with 55 parts by weight of urea and 15 parts by weight of monoacetyl urea.
I claim:
1. In the process for dyeing articles produced from a member selected from the group consisting of polyacrylonitrile, polyvinylidene-cyanide and copolymers thereof with other vinyl compounds, the improvement which comprises applying onto said articles, as leveling agent, a quaternary ammonium compound containing attached to the nitrogen atom an alkyl radical of at least 8 carbon atoms, and a radical selected from the group consisting of benzyl and halogenated benzyl.
2. A process according to claim 1 which comprises applying said quaternary ammonium compound in form of its reaction product with a compound selected from the group consisting of urea and derivatives of urea.
3. A process of claim 1 wherein the quaternary ammonium compound is dimethyl-cetyl-benzyl-ammonium chloride.
4. A process of claim 1 wherein the quaternary ammonium compound is the reaction product of dimethylpalm-kernel fatty amine with benzyl chloride.
5. A process of claim 1 wherein the leveling agent is the addition product of dimethyl-cetyl-benzyl-ammonium chloride, urea and monoacetyl urea.
6. A process of claim 1 wherein the leveling agent is the addition product obtained by melting urea, monoacetyl urea and a quaternary ammonium compound obtained by reacting dimethyl-palmkernel fatty amine with benzyl chloride.
References Cited in the file of this patent Man-Made Textiles, December 1955, pp. 67-68.
Diserens: The Chem. Tech. of Dyeing and Printing, vol. II, Reinhold Pub. Corp., N.Y., 1951, pp. 108, 327- 328.
Venkataraman: The Chem. of Synthetic Dyes, Academic Press Inc., 1952, N.Y., pp. 295, 879.
Claims (1)
1. IN THE PROCESS FOR DYEING ARTICLES PRODUCED FROM A MEMBER SELECTED FROM THE GROUP CONSISTING OF POLYACRYLONITRILE, POLYVINYLIDENE-CYANIDE AND COPOLYMERS THEREOF WITH OTHER VINYL COMPOUNDS, THE IMPROVEMENT WHICH COMPRISES APPLYING ONTO SAID ARTICLES, AS LEVELING AGENT, A QUATERNARY AMMONIUM COMPOUND CONTAINING ATTACHED TO THE NITROGEN ATOM AN ALKYL RADICAL OF AT LEAST 8 CARBON ATOMS, AND A RADICAL SELECTED FROM THE GROUP CONSISTING OF BENZYL AND HALOGENATED BENZYL.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2989361A true US2989361A (en) | 1961-06-20 |
Family
ID=3450027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2989361D Expired - Lifetime US2989361A (en) | Dyeing process |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2989361A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185538A (en) * | 1962-04-10 | 1965-05-25 | Geigy Ag J R | Process for coloring polyacrylonitrile fibers with methine dye salts |
| US3387916A (en) * | 1964-06-23 | 1968-06-11 | Du Pont | Heteropoly acid coloration medium and process |
| US3652201A (en) * | 1968-04-30 | 1972-03-28 | Ciba Geigy Ag | Process for the production of dyeings on fiber material consisting of polymeric or copolymeric acrylonitrile |
| US3785768A (en) * | 1970-09-11 | 1974-01-15 | Bayer Ag | Process for the dyeing of fibre material consisting of polyacrylonitrile or acrylonitrile-containing copolymers |
-
0
- US US2989361D patent/US2989361A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185538A (en) * | 1962-04-10 | 1965-05-25 | Geigy Ag J R | Process for coloring polyacrylonitrile fibers with methine dye salts |
| US3387916A (en) * | 1964-06-23 | 1968-06-11 | Du Pont | Heteropoly acid coloration medium and process |
| US3652201A (en) * | 1968-04-30 | 1972-03-28 | Ciba Geigy Ag | Process for the production of dyeings on fiber material consisting of polymeric or copolymeric acrylonitrile |
| US3785768A (en) * | 1970-09-11 | 1974-01-15 | Bayer Ag | Process for the dyeing of fibre material consisting of polyacrylonitrile or acrylonitrile-containing copolymers |
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