JPH0472863B2 - - Google Patents
Info
- Publication number
- JPH0472863B2 JPH0472863B2 JP58021835A JP2183583A JPH0472863B2 JP H0472863 B2 JPH0472863 B2 JP H0472863B2 JP 58021835 A JP58021835 A JP 58021835A JP 2183583 A JP2183583 A JP 2183583A JP H0472863 B2 JPH0472863 B2 JP H0472863B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl group
- parts
- tetrahydroquinoline
- formula
- 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
- -1 cyano, hydroxy Chemical group 0.000 claims description 50
- 238000004043 dyeing Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000012209 synthetic fiber Substances 0.000 claims description 8
- 229920002994 synthetic fiber Polymers 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 15
- 239000000835 fiber Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- MLOXIXGLIZLPDP-UHFFFAOYSA-N 2-amino-1h-imidazole-4,5-dicarbonitrile Chemical compound NC1=NC(C#N)=C(C#N)N1 MLOXIXGLIZLPDP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000012736 aqueous medium 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical group C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- POMFALRACOICMG-UHFFFAOYSA-N 1-cyclohexyl-2,2,4-trimethyl-3,4-dihydroquinoline Chemical compound C12=CC=CC=C2C(C)CC(C)(C)N1C1CCCCC1 POMFALRACOICMG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
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The present invention relates to a novel monoazo compound and a method for dyeing or printing synthetic fibers using the same. More specifically, the present invention relates to a water-insoluble monoazo compound and a method for dyeing or printing synthetic fibers such as polyester fibers and polyamide fibers in bright red using the same. That is, the present invention provides the general formula () (In the formula, X is an alkyl group, cyano, hydroxy,
an alkyl group, an alkenyl group, an aralkyl group, or a tetrahydrofurfuryl group substituted with lower alkoxy, phenoxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylcarbonyloxy, or tetrahydrofurfuryloxy; Y is a hydrogen atom, a halogen atom, or a lower alkyl group; group, lower alkoxy group, acylamino group, benzoylamino group or alkylsulfonylamino group, Z is hydrogen atom, alkyl group, cyano, hydroxy, lower alkoxy, phenoxy, benzyloxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylcarbonyloxy , lower alkoxycarbonyloxy, phenoxycarbonyl, benzoyloxy, cyanoethyloxy,
It represents an alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group substituted with lower alkylcarbonylamino, lower alkoxyalkoxy, phenylaminocarbonyloxy or benzylcarbonyloxy. ) A method for dyeing or printing synthetic fibers characterized by using the monoazo compound shown in the following. In the present invention, "lower" means having 1 to 4 carbon atoms. In the compound represented by the general formula (), Y is preferably a hydrogen atom, a chlorine atom, a methyl group, a lower acylamino group, a benzoylamino group, a lower alkylsulfonylamino group, and Z is an alkyl group having 1 to 8 carbon atoms. , an allyl group, a benzyl group, a phenethyl group, and a substituted alkyl group having a phenyl ring are preferred. The monoazo compound of the present invention has excellent properties as a disperse dye for synthetic fibers such as polyester fibers and polyamide fibers, such as dyeing properties, dye bath stability, PH stability, and build-up properties, and is also resistant to water and washing. It exhibits excellent fastness to various types of light, such as maturation, sublimation, and sunlight, especially after post-processing. or,
It is noteworthy that when the substituent Z in the general formula () is a substituted alkyl group or an aralkyl group having a phenyl ring, it has even better performance in sunlight fastness. In the present invention, the monoazo compound represented by the general formula () is the monoazo compound represented by the formula () The amine compound represented by is diazotized by a known method to form the general formula () (In the formula, Y and Z represent the above meanings.) General formula () obtained by coupling with a compound represented by (In the formula, Y and Z represent the above-mentioned meanings.) It can be produced by substituting the hydrogen atom of the imidazole ring of the monoazo compound shown by the following with an X group. Specifically, the monoazo compound of the present invention can be produced, for example, as follows. The amine compound represented by the formula () is dissolved or dispersed in a mineral acid such as sulfuric acid or hydrochloric acid, or an organic acid such as acetic acid or propionic acid, or a mixed solvent thereof, and the amine compound is dissolved or dispersed in a nitrous acid solution when cold, preferably at 5°C or below. Diazotize with soda or nitrosyl sulfate.
On the other hand, the compound represented by the general formula (), sulfuric acid,
The diazonium compound is dissolved in a mineral acid such as hydrochloric acid, an organic acid such as acetic acid or propionic acid, or an organic solvent such as methanol or ethanol, or a mixed solvent thereof, and the diazonium compound is added thereto preferably at 10%
Add at below â and couple. At this time, depending on the case, it is preferable to adjust the pH to 1 to 5 because coupling occurs quickly. After the reaction is completed, the precipitated crystals are separated, washed with water, and dried to obtain a monoazo compound represented by the general formula (). The compound represented by the general formula () thus obtained is alkylated using an alkylating agent in an inert organic solvent, water, or a water-organic solvent to obtain a compound represented by the general formula (). As the alkylating agent, halogen compounds, toluenesulfonic acid esters, and alkylene oxides are preferred. Specific examples of the compound represented by the general formula () include the following. 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline 1-ethyl-2,2,4-trimethyl-1,2,
3,4-tetrahydroquinoline 1-butyl-2,2,4-trimethyl-1,2,
3,4-tetrahydroquinoline 1-(2-hydroxyethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline 1-(2-cyanoethyl)-2,2,4-trimethyl-1 , 2,3,4-tetrahydroquinoline 1-(2-acetoxyethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline 1-benzyl-2,2,4-trimethyl-1,
2,3,4,tetrahydroquinoline 1-cyclohexyl-2,2,4-trimethyl-
1,2,3,4-tetrahydroquinoline 1-allyl-2,2,4-trimethyl-1,2,
3,4-tetrahydroquinoline 1-phenethyl-2,2,4-trimethyl-1,
2,3,4-Tetrahydroquinoline 1-propyl-2,2,4-trimethyl-7-chloro-1,2,3,4-tetrahydroquinoline 1-(2-phenoxyethyl)-2,2,4-trimethyl- 7-acetylamino-1,2,3,4-
Tetrahydroquinoline 1-(2-benzoyloxyethyl)-2,2,
4,7-tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-phenylcarbamoyloxyethyl)-
2,2,4-trimethyl-7-benzoylamino-1,2,3,4-tetrahydroquinoline 1-(2-benzyloxyethyl)-2,2,4,
7-tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-methoxycarbonyloxyethyl)-
2,2,4-trimethyl-7-methylsulfonylamino-1,2,3,4-tetrahydroquinoline 1-(2-methoxycarbonylethyl)-2,2,
4-trimethyl-7-ethyl-1,2,3,4-
Tetrahydroquinoline 1-(2-benzylcarbonyloxyethyl-2,
2,4,7-trimethyl-1,2,3,4-tetrahydroquinoline 1-phenethyl-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-phenoxyethyl) -2,2,4,7-
Tetramethyl-1,2,3,4-tetrahydroquinoline 1-amyl-2,2,4-trimethyl-7-propionylamino-1,2,3,4-tetrahydroquinoline 1-hexyl-2,2,4- Trimethyl-7-methoxy-1,2,3,4-tetrahydroquinoline 1-(2-propionyloxyethyl)-2,2,
4,7-tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-carbamoylethyl)-2,2,4-trimethyl-7-chloro-1,2,3,4-tetrahydroquinoline 1- (2-allyloxyethyl)-2,2,4-trimethyl-7-acetylamino-1,2,3,4-
Tetrahydroquinoline 1-(3-methoxypropyl)-2,2,4-trimethyl-7-ethoxy-1,2,3,4-tetrahydroquinoline The synthetic fibers in the present invention include polyester fibers, polyamide fibers, Examples include polyolefin fibers, cellulose ester fibers, and blends of these fibers. The compound of the present invention exhibits excellent dyeing properties particularly for polyester fibers. When dyeing synthetic fibers using the compound of the present invention, one or more monoazo compounds represented by the general formula () are first ground into fine particles in an aqueous medium together with a suitable dispersant. and decentralize it. The dispersed dye can be used as a liquid or as a powder by spray drying. Dyeing is carried out by a method known per se, in which a dispersed dye is dispersed in an aqueous medium to prepare a dye bath, the synthetic fiber is immersed, and the dyeing process is carried out under pressure at 105°C or higher, preferably at 110 to 140°C.
dyeing at a relatively high temperature, e.g. boiling water, in the presence of a carrier such as O-phenylphenol or trichlorobenzene, or by plating the dye dispersion onto the fabric and dyeing at 150-230°C for 30-30°C.
Dyeing is done using the so-called thermosol dyeing method, which involves dry heat treatment for 120 seconds, or in the case of textile printing, the dye dispersion is kneaded with a suitable sizing agent, this is patched onto the fabric, and dyed by steaming or thermosol treatment. It can be carried out. Furthermore, a solvent dyeing method using an organic solvent such as trichlorethylene or perchloroethylene as a dyeing medium is also possible. EXAMPLES Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited by these Examples. In the text, parts and % mean parts by weight and % by weight, respectively, unless otherwise specified. Example 1 2-amino-4,5-dicyanoimidazole
Disperse 13.3 parts in 330 parts of water and 32 parts of concentrated hydrochloric acid.
After cooling to 5°C, add 7 parts of sodium nitrite (14%
50 parts of aqueous solution) is added at 0-5°C. The reaction was carried out at the same temperature for 1 hour to complete the diazotization. On the other hand, 1-ethyl-2,2,4-trimethyl-
20.3 parts of 1,2,3,4-tetrahydroquinoline are dissolved in 100 parts of acetic acid, and the above diazonium solution is added thereto at 0-5°C. Separately, the precipitated crystals were washed with water and dried, and the formula (1) was obtained. 31.2 parts (yield 90%) of the compound represented by was obtained. Next, 17.4 parts of the compound of formula (1) was dissolved in 200 parts of dimethylformamide, 15.4 parts of diethyl sulfate and 6.4 parts of sodium carbonate were added, and the mixture was reacted at 60°C for 10 hours. After completion of the reaction, the precipitated crystals were separated into 1000 parts of water, washed with water, and dried to obtain the formula (2). 15.0 parts (yield: 80%) of the compound shown was obtained. λmax (90% DMF) 544 nm Example 2 1 part of the monoazo compound of formula (2) is atomized and dispersed together with 1 part of formalin condensate of naphthalene sulfonic acid and 1 part of sodium lignin sulfonate, and this and 3 parts of higher alcohol sulfuric ester are dispersed. A dyebath is prepared by uniformly dispersing the mixture in 3000 parts of water. After immersing 100 parts of polyester processed yarn fabric in this dye bath and dyeing at 130°C for 60 minutes, the dyed product was mixed with 3 parts of caustic soda, 3 parts of hydrosulfite, 3 parts of betaine type amphoteric surfactant, and 3000 parts of water. Reduction treatment was carried out at 85°C for 10 minutes using a treatment solution consisting of Thereafter, the dyed product was washed with water and dried to obtain a highly concentrated and vivid red dyed product.
This dyeing showed excellent performance in sublimation, sunlight, water and washing fastness. Example 3 2-amino-4,5-dicyanoimidazole
Disperse 13.3 parts in water, 330 parts water and 32 parts concentrated hydrochloric acid. After cooling to 5°C, 7 parts of sodium nitrite are added at 0-5°C. Diazotization is completed by reacting at the same temperature for 1 hour. On the other hand, 1-(2-phenoxyethyl)-2,2,
30.9 parts of 4,7-tetramethyl-1,2,3,4-tetrahydroquinoline is dissolved in 200 parts of methanol, and the diazonium solution is added thereto at 0-5°C. After stirring at the same temperature for 3 hours, the precipitated crystals were separated, washed with water, and dried to form the formula (3). 38.5 parts (yield 85%) of the compound represented by was obtained. Next, 22.7 parts of the compound of formula (3) are dissolved in 300 parts of N-methylpyrrolidone, 5.2 parts of potassium carbonate are added, and then 5.7 parts of chloroacetonitrile is added dropwise at 80°C. After reacting at the same temperature for 10 hours, it was distilled into 1000 parts of water, and the precipitated crystals were separated, washed with water, dried, and the formula (4) was obtained. 17.2 parts (yield 70%) of the compound represented by was obtained. λmax (90% DMF) 515 nm Example 4 1 part of the compound of formula (4) was atomized and dispersed with 2 parts of a formalin condensate of naphthalene sulfonic acid, and the resulting dye composition was added to 95 parts of a printing base paste with the following composition. In addition,
Mix well to prepare colored glue. (Material printing paste) 12% Maypro Gum NP-60 (Locust Bean Gum) 63 parts Sodium chlorate 0.6 parts Tartaric acid 0.4 parts Water 36 parts 100 parts This color paste was printed on polyester processed thread fabric.
After drying, it was steamed for 30 minutes using a high-pressure steamer (temperature 130-135°C, gauge pressure 3-4 Kg/cm 2 ). Thereafter, it was washed with water, subjected to a reduction washing treatment in the same manner as in Example 2, washed with water, and dried to obtain a highly concentrated and vivid red dyed product. This dye is
It showed excellent performance in sublimation, sunlight, water and washing fastness. Thereafter, the monoazo compounds shown in Table 1 were synthesized in the same manner as in Example 1, and each was dyed in the same manner as in Example 2 to obtain the results shown in Table 1. The hues in Table 1 are the hues on polyester fibers.
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Claims (1)
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ããåæç¹ç¶é¡ã®æè²ãŸãã¯æºææ³ã[Claims] 1 General formula () (In the formula, X is an alkyl group, cyano, hydroxy,
an alkyl group, an alkenyl group, an aralkyl group, or a tetrahydrofurfuryl group substituted with lower alkoxy, phenoxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylcarbonyloxy, or tetrahydrofurfuryloxy; Y is a hydrogen atom, a halogen atom, or a lower alkyl group; group, lower alkoxy group, acylamino group, benzoylamino group or alkylsulfonylamino group, Z is hydrogen atom, alkyl group, cyano, hydroxy, lower alkoxy, phenoxy, benzyloxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylcarbonyloxy , lower alkoxycarbonyloxy, phenoxycarbonyl, benzoyloxy, cyanoethyloxy,
It represents an alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group substituted with lower alkylcarbonylamino, lower alkoxyalkoxy, phenylaminocarbonyloxy or benzylcarbonyloxy. ) A monoazo compound represented by 2 General formula () (In the formula, X is an alkyl group, cyano, hydroxy,
Alkyl group, alkenyl group, aralkyl group or tetrahydrofurfuryl group substituted with lower alkoxy, phenoxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylbonyloxy or tetrahydrofurfuryloxy, Y
is a hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, acylamino group, benzoylamino group or alkylsulfonylamino group, Z is a hydrogen atom, alkyl group, cyano, hydroxy, lower alkoxy, phenoxy, benzyloxy, lower alkenyloxy , lower alkoxycarbonyl, lower alkylcarbonyloxy, lower alkoxycarbonyloxy, phenoxycarbonyl,
It represents an alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group substituted with benzoyloxy, cyanoethyloxy, lower alkylcarbonylamino, lower alkoxyalkoxy, phenylaminocarbonyloxy or benzylcarbonyloxy. ) A dyeing or printing method for synthetic fibers, characterized by using a monoazo compound represented by:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58021835A JPS59147052A (en) | 1983-02-12 | 1983-02-12 | Monoazo compound and method for dyeing using thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58021835A JPS59147052A (en) | 1983-02-12 | 1983-02-12 | Monoazo compound and method for dyeing using thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59147052A JPS59147052A (en) | 1984-08-23 |
JPH0472863B2 true JPH0472863B2 (en) | 1992-11-19 |
Family
ID=12066125
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58021835A Granted JPS59147052A (en) | 1983-02-12 | 1983-02-12 | Monoazo compound and method for dyeing using thereof |
Country Status (1)
Country | Link |
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JP (1) | JPS59147052A (en) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4854283A (en) * | 1971-11-09 | 1973-07-30 | ||
JPS4953222A (en) * | 1972-07-11 | 1974-05-23 | ||
JPS50138020A (en) * | 1974-04-03 | 1975-11-04 | ||
JPS51124122A (en) * | 1975-04-22 | 1976-10-29 | Hodogaya Chem Co Ltd | Process for producing azo dyes |
JPS55161856A (en) * | 1979-06-01 | 1980-12-16 | Eastman Kodak Co | Azo dye or its salt derived from sulfoocontaining aromatic amine and pentaheterocyclic amine |
JPS5645956A (en) * | 1979-09-25 | 1981-04-25 | Mitsubishi Chem Ind Ltd | Monoazo dye for polyester fiber |
JPS572363A (en) * | 1980-06-06 | 1982-01-07 | Mitsubishi Chem Ind Ltd | Monoazo dye for polyester fiber |
-
1983
- 1983-02-12 JP JP58021835A patent/JPS59147052A/en active Granted
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4854283A (en) * | 1971-11-09 | 1973-07-30 | ||
JPS4953222A (en) * | 1972-07-11 | 1974-05-23 | ||
JPS50138020A (en) * | 1974-04-03 | 1975-11-04 | ||
JPS51124122A (en) * | 1975-04-22 | 1976-10-29 | Hodogaya Chem Co Ltd | Process for producing azo dyes |
JPS55161856A (en) * | 1979-06-01 | 1980-12-16 | Eastman Kodak Co | Azo dye or its salt derived from sulfoocontaining aromatic amine and pentaheterocyclic amine |
JPS5645956A (en) * | 1979-09-25 | 1981-04-25 | Mitsubishi Chem Ind Ltd | Monoazo dye for polyester fiber |
JPS572363A (en) * | 1980-06-06 | 1982-01-07 | Mitsubishi Chem Ind Ltd | Monoazo dye for polyester fiber |
Also Published As
Publication number | Publication date |
---|---|
JPS59147052A (en) | 1984-08-23 |
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