CH621567A5 - Process for preparing new aminoazines - Google Patents
Process for preparing new aminoazines Download PDFInfo
- Publication number
- CH621567A5 CH621567A5 CH1452774A CH1452774A CH621567A5 CH 621567 A5 CH621567 A5 CH 621567A5 CH 1452774 A CH1452774 A CH 1452774A CH 1452774 A CH1452774 A CH 1452774A CH 621567 A5 CH621567 A5 CH 621567A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfo
- carbon atoms
- formula
- alkyl
- group
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 14
- -1 sulfobenzyl Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- JXZGTFLJFKLVAX-UHFFFAOYSA-N 5-amino-2-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C=C1S(O)(=O)=O JXZGTFLJFKLVAX-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QWUFXJHVFNRNCU-UHFFFAOYSA-N phenazin-1-amine Chemical compound C1=CC=C2N=C3C(N)=CC=CC3=NC2=C1 QWUFXJHVFNRNCU-UHFFFAOYSA-N 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BQGRVFPPZJPWPB-UHFFFAOYSA-N 3-[(n-ethylanilino)methyl]benzenesulfonic acid Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 BQGRVFPPZJPWPB-UHFFFAOYSA-N 0.000 description 3
- JIYCNHGAAQDQTN-UHFFFAOYSA-N 3-[(n-methylanilino)methyl]benzenesulfonic acid Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC(S(O)(=O)=O)=C1 JIYCNHGAAQDQTN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- JYDRNIYTFCBIFC-UHFFFAOYSA-N disodium;oxido-(oxido(dioxo)chromio)oxy-dioxochromium;dihydrate Chemical compound O.O.[Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O JYDRNIYTFCBIFC-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- GDRHJDPDUDFIBY-UHFFFAOYSA-N 3-[(N-propylanilino)methyl]benzenesulfonic acid Chemical compound C=1C=CC=CC=1N(CCC)CC1=CC=CC(S(O)(=O)=O)=C1 GDRHJDPDUDFIBY-UHFFFAOYSA-N 0.000 description 1
- LOMARNNLNHURJZ-UHFFFAOYSA-N 4-amino-2-methoxybenzenesulfonic acid Chemical compound COC1=CC(N)=CC=C1S(O)(=O)=O LOMARNNLNHURJZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- VSANMHWDSONVEE-UHFFFAOYSA-N carbyl sulfate Chemical compound O=S1(=O)CCOS(=O)(=O)O1 VSANMHWDSONVEE-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 1
- LXZGVFCKZRHKMU-UHFFFAOYSA-N n-benzyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/0025—Specific dyes not provided for in groups C09B62/004 - C09B62/018
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB649972A GB1374852A (en) | 1972-02-11 | 1972-02-11 | Reactive dyestuffs |
| GB4052273 | 1973-08-28 | ||
| GB1229474*[A GB1440948A (en) | 1973-08-28 | 1974-03-20 | Reactive dyes |
| GB2711774 | 1974-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621567A5 true CH621567A5 (en) | 1981-02-13 |
Family
ID=27447525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1452774A CH621567A5 (en) | 1972-02-11 | 1974-10-30 | Process for preparing new aminoazines |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH621567A5 (enExample) |
| DE (1) | DE2438036A1 (enExample) |
| FR (1) | FR2242446B2 (enExample) |
| NL (1) | NL7411377A (enExample) |
-
1974
- 1974-08-07 DE DE19742438036 patent/DE2438036A1/de not_active Ceased
- 1974-08-27 NL NL7411377A patent/NL7411377A/xx not_active Application Discontinuation
- 1974-08-27 FR FR7429312A patent/FR2242446B2/fr not_active Expired
- 1974-10-30 CH CH1452774A patent/CH621567A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2438036A1 (de) | 1975-03-06 |
| FR2242446B2 (enExample) | 1979-01-05 |
| FR2242446A2 (enExample) | 1975-03-28 |
| NL7411377A (nl) | 1975-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |