DE1131828B - Verfahren zur Herstellung von wasserunloeslichen Disazofarbstoffen - Google Patents
Verfahren zur Herstellung von wasserunloeslichen DisazofarbstoffenInfo
- Publication number
- DE1131828B DE1131828B DEF27856A DEF0027856A DE1131828B DE 1131828 B DE1131828 B DE 1131828B DE F27856 A DEF27856 A DE F27856A DE F0027856 A DEF0027856 A DE F0027856A DE 1131828 B DE1131828 B DE 1131828B
- Authority
- DE
- Germany
- Prior art keywords
- acetoacetylamino
- water
- yellow
- preparation
- dyes
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 acetoacetylamino compounds Chemical class 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- WZMYPGAPLAOSDX-UHFFFAOYSA-N n-(2-chloro-4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1Cl WZMYPGAPLAOSDX-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- ODFRAIZRJMUPCP-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1C ODFRAIZRJMUPCP-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NNAVBEAARXTLEG-UHFFFAOYSA-N 2-(10-methylundecyl)phenol Chemical compound CC(C)CCCCCCCCCC1=CC=CC=C1O NNAVBEAARXTLEG-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ZXUSQOYCALFTBR-UHFFFAOYSA-N N-(4-acetamido-2-chlorophenyl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1=C(C=C(C=C1)NC(C)=O)Cl ZXUSQOYCALFTBR-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- YTKNYOWCICFXOW-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1Cl YTKNYOWCICFXOW-UHFFFAOYSA-N 0.000 description 1
- VHUHDNBYBJVATB-UHFFFAOYSA-N n-(2-acetamidophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1NC(C)=O VHUHDNBYBJVATB-UHFFFAOYSA-N 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
- BSGZZIRKDQLKBD-UHFFFAOYSA-N n-(2-ethylphenyl)-3-oxobutanamide Chemical compound CCC1=CC=CC=C1NC(=O)CC(C)=O BSGZZIRKDQLKBD-UHFFFAOYSA-N 0.000 description 1
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 1
- DFICAKPWTZYLND-UHFFFAOYSA-N n-(4-acetamido-5-chloro-2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1NC(=O)CC(C)=O DFICAKPWTZYLND-UHFFFAOYSA-N 0.000 description 1
- PNVSDRLLBNUJBE-UHFFFAOYSA-N n-(4-acetamidophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(NC(C)=O)C=C1 PNVSDRLLBNUJBE-UHFFFAOYSA-N 0.000 description 1
- LWJIFNULDBNYCR-UHFFFAOYSA-N n-(4-bromo-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Br)C=C1C LWJIFNULDBNYCR-UHFFFAOYSA-N 0.000 description 1
- MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 1
- DEUYYSQQVMVIDJ-UHFFFAOYSA-N n-(4-chloro-2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(Cl)=CC=C1NC(=O)CC(C)=O DEUYYSQQVMVIDJ-UHFFFAOYSA-N 0.000 description 1
- WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 description 1
- SWAJJKROCOJICG-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(NC(=O)CC(C)=O)C=C1 SWAJJKROCOJICG-UHFFFAOYSA-N 0.000 description 1
- MJGLMEMIYDUEHA-UHFFFAOYSA-N n-(4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1 MJGLMEMIYDUEHA-UHFFFAOYSA-N 0.000 description 1
- RKBATQSRJPGXIS-UHFFFAOYSA-N n-(5-acetamido-2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(NC(C)=O)C=C1NC(=O)CC(C)=O RKBATQSRJPGXIS-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/105—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from two coupling components with reactive methylene groups
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Surgical Instruments (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR79529D FR79529A (en:Method) | 1959-03-04 | ||
| DEF27856A DE1131828B (de) | 1959-03-04 | 1959-03-04 | Verfahren zur Herstellung von wasserunloeslichen Disazofarbstoffen |
| FR795356A FR1225279A (fr) | 1959-03-04 | 1959-05-22 | Colorant disazoïque insoluble dans l'eau et sa préparation |
| CH234960A CH413171A (de) | 1959-03-04 | 1960-03-02 | Verfahren zur Herstellung von wasserunlöslichen Disazofarbstoffen |
| NL249067A NL124328C (en:Method) | 1959-03-04 | 1960-03-04 | |
| GB782060A GB951764A (en) | 1959-03-04 | 1960-03-04 | Water-insoluble disazo-dyestuffs derived from diaminotetrachlorodiphenyl and process for their manufacture |
| BE588314A BE588314R (fr) | 1959-03-04 | 1960-03-04 | Colorant disazoïque insoluble dans l'eau et sa préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF27856A DE1131828B (de) | 1959-03-04 | 1959-03-04 | Verfahren zur Herstellung von wasserunloeslichen Disazofarbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1131828B true DE1131828B (de) | 1962-06-20 |
Family
ID=7092631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF27856A Pending DE1131828B (de) | 1959-03-04 | 1959-03-04 | Verfahren zur Herstellung von wasserunloeslichen Disazofarbstoffen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE588314R (en:Method) |
| CH (1) | CH413171A (en:Method) |
| DE (1) | DE1131828B (en:Method) |
| FR (2) | FR1225279A (en:Method) |
| GB (1) | GB951764A (en:Method) |
| NL (1) | NL124328C (en:Method) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1932577A (en) * | 1931-12-24 | 1933-10-31 | Gen Aniline Works Inc | Water-insoluble disazo-dyestuffs |
-
0
- FR FR79529D patent/FR79529A/fr active Active
-
1959
- 1959-03-04 DE DEF27856A patent/DE1131828B/de active Pending
- 1959-05-22 FR FR795356A patent/FR1225279A/fr not_active Expired
-
1960
- 1960-03-02 CH CH234960A patent/CH413171A/fr unknown
- 1960-03-04 BE BE588314A patent/BE588314R/fr active
- 1960-03-04 GB GB782060A patent/GB951764A/en not_active Expired
- 1960-03-04 NL NL249067A patent/NL124328C/xx active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1932577A (en) * | 1931-12-24 | 1933-10-31 | Gen Aniline Works Inc | Water-insoluble disazo-dyestuffs |
Also Published As
| Publication number | Publication date |
|---|---|
| BE588314R (fr) | 1960-09-05 |
| FR79529A (en:Method) | |
| GB951764A (en) | 1964-03-11 |
| NL124328C (en:Method) | 1968-05-15 |
| NL249067A (en:Method) | 1964-04-10 |
| FR1225279A (fr) | 1960-06-30 |
| CH413171A (de) | 1966-05-15 |
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