JPS58225156A - モノアゾ染料及びその製法 - Google Patents
モノアゾ染料及びその製法Info
- Publication number
- JPS58225156A JPS58225156A JP10655482A JP10655482A JPS58225156A JP S58225156 A JPS58225156 A JP S58225156A JP 10655482 A JP10655482 A JP 10655482A JP 10655482 A JP10655482 A JP 10655482A JP S58225156 A JPS58225156 A JP S58225156A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- dyeing
- monoazo dye
- crystalline compound
- temperature
- 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.)
- Granted
Links
- 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 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 6
- 239000012736 aqueous medium Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000010586 diagram Methods 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 12
- 238000007639 printing Methods 0.000 abstract description 4
- 229920000728 polyester Polymers 0.000 abstract description 3
- 229920000742 Cotton Polymers 0.000 abstract description 2
- FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 abstract description 2
- 210000002268 wool Anatomy 0.000 abstract description 2
- 239000004744 fabric Substances 0.000 abstract 2
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 abstract 1
- 238000007598 dipping method Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 32
- 238000004043 dyeing Methods 0.000 description 20
- 238000012986 modification Methods 0.000 description 13
- 230000004048 modification Effects 0.000 description 13
- 230000009466 transformation Effects 0.000 description 11
- -1 monoazo compound Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000002050 diffraction method Methods 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 239000002270 dispersing agent 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- BZOVBIIWPDQIHF-UHFFFAOYSA-N 3-hydroxy-2-methylbenzenesulfonic acid Chemical compound CC1=C(O)C=CC=C1S(O)(=O)=O BZOVBIIWPDQIHF-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000009974 package dyeing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000009976 warp beam dyeing Methods 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
- C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10655482A JPS58225156A (ja) | 1982-06-21 | 1982-06-21 | モノアゾ染料及びその製法 |
| GB08316289A GB2123845B (en) | 1982-06-21 | 1983-06-15 | Crystalline mono azo dye and its production |
| CH334483A CH653356A5 (de) | 1982-06-21 | 1983-06-17 | Monoazofarbstoff und verfahren zu dessen herstellung. |
| DE19833322301 DE3322301A1 (de) | 1982-06-21 | 1983-06-21 | Monoazofarbstoff und verfahren zu dessen herstellung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10655482A JPS58225156A (ja) | 1982-06-21 | 1982-06-21 | モノアゾ染料及びその製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58225156A true JPS58225156A (ja) | 1983-12-27 |
| JPS6340451B2 JPS6340451B2 (enrdf_load_stackoverflow) | 1988-08-11 |
Family
ID=14436550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10655482A Granted JPS58225156A (ja) | 1982-06-21 | 1982-06-21 | モノアゾ染料及びその製法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS58225156A (enrdf_load_stackoverflow) |
| CH (1) | CH653356A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3322301A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2123845B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997034955A1 (fr) * | 1996-03-19 | 1997-09-25 | Nippon Kayaku Co., Ltd. | Modification cristalline thermostable de colorant, procede de preparation correspondant et procedes de teinture de fibres hydrophobes a l'aide dudit colorant |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19501845A1 (de) * | 1995-01-23 | 1996-07-25 | Cassella Ag | Färbestabiler Monoazofarbstoff, dessen Herstellung und Verwendung |
| CN105623299B (zh) * | 2015-11-19 | 2018-03-23 | 浙江闰土研究院有限公司 | 一种化合物新晶型、其制备方法及用途 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL128389C (enrdf_load_stackoverflow) * | 1963-02-15 | |||
| US3956270A (en) * | 1972-10-11 | 1976-05-11 | Basf Aktiengesellschaft | β-Modified azo dye |
| DE2347532C2 (de) * | 1973-09-21 | 1975-10-30 | Hoechst Ag, 6000 Frankfurt | Monoazopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE2363376C3 (de) * | 1973-12-20 | 1978-03-02 | Cassella Farbwerke Mainkur Ag, 6000 Frankfurt | Formierter, wasserunlöslicher Azofarbstoff und seine Herstellung und Verwendung |
| NL7513637A (nl) * | 1974-11-26 | 1976-05-31 | Hoechst Ag | Werkwijze voor het bereiden van een bij het ver- ven stabiele monoazokleurstof, alsmede haar toe- passing. |
| CH602898A5 (enrdf_load_stackoverflow) * | 1975-05-09 | 1978-08-15 | Hoechst Ag | |
| GB1543316A (en) * | 1975-09-01 | 1979-04-04 | Ici Ltd | Stabilised disperse azo dyestuff |
| DE2642730C3 (de) * | 1976-09-23 | 1979-03-08 | Hoechst Ag, 6000 Frankfurt | Färbestabile Modifikation von Mischfarbstoffen |
| DE2835544B1 (de) * | 1978-08-14 | 1979-05-31 | Hoechst Ag | Faerbestabiler Monoazofarbstoff,dessen Herstellung und Verwendung |
| DE2921210A1 (de) * | 1979-05-25 | 1980-12-04 | Hoechst Ag | Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung |
| DE2948016A1 (de) * | 1979-11-29 | 1981-06-11 | Basf Ag, 6700 Ludwigshafen | Faerbestabile modifikation eines dispersionsfarbstoffes |
| DE2950588A1 (de) * | 1979-12-15 | 1981-06-19 | Hoechst Ag, 6230 Frankfurt | Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung |
| US4327999A (en) * | 1980-01-09 | 1982-05-04 | Ciba-Geigy Corporation | Disperse dye stable to dyeing, and its use for dyeing synthetic and semi-synthetic fibre materials |
| US4332588A (en) * | 1980-01-11 | 1982-06-01 | Ciba-Geigy Corporation | Disperse dye stable to dyeing, and its use for dyeing and printing synthetic and semi-synthetic fibre materials |
| DE3012290A1 (de) * | 1980-03-29 | 1981-10-15 | Joseph Hombrechtikon Hirs | Verfahren und einrichtung zur vertreibung von voegeln und klein-nagetieren |
-
1982
- 1982-06-21 JP JP10655482A patent/JPS58225156A/ja active Granted
-
1983
- 1983-06-15 GB GB08316289A patent/GB2123845B/en not_active Expired
- 1983-06-17 CH CH334483A patent/CH653356A5/de not_active IP Right Cessation
- 1983-06-21 DE DE19833322301 patent/DE3322301A1/de not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997034955A1 (fr) * | 1996-03-19 | 1997-09-25 | Nippon Kayaku Co., Ltd. | Modification cristalline thermostable de colorant, procede de preparation correspondant et procedes de teinture de fibres hydrophobes a l'aide dudit colorant |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6340451B2 (enrdf_load_stackoverflow) | 1988-08-11 |
| GB8316289D0 (en) | 1983-07-20 |
| GB2123845A (en) | 1984-02-08 |
| GB2123845B (en) | 1986-02-19 |
| DE3322301A1 (de) | 1984-01-05 |
| CH653356A5 (de) | 1985-12-31 |
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