US2688616A - Fast bases of the triazine series - Google Patents
Fast bases of the triazine series Download PDFInfo
- Publication number
- US2688616A US2688616A US2688616DA US2688616A US 2688616 A US2688616 A US 2688616A US 2688616D A US2688616D A US 2688616DA US 2688616 A US2688616 A US 2688616A
- Authority
- US
- United States
- Prior art keywords
- bases
- triazine series
- fast
- acid
- compounds
- 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
- BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical compound C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- 230000001808 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 4
- 241000974482 Aricia saepiolus Species 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- -1 diazoamino Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- CZTSOXCSVFEFIK-UHFFFAOYSA-N 2-benzylnaphthalen-1-ol Chemical class C1=CC2=CC=CC=C2C(O)=C1CC1=CC=CC=C1 CZTSOXCSVFEFIK-UHFFFAOYSA-N 0.000 description 2
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- NTHCNNBLHWLJDL-UHFFFAOYSA-N 2-hydroxy-11H-benzo[a]carbazole-1-carboxylic acid Chemical class C1=CC=C2NC3=C4C(C(=O)O)=C(O)C=CC4=CC=C3C2=C1 NTHCNNBLHWLJDL-UHFFFAOYSA-N 0.000 description 2
- YSJWNEDBIWZWOI-UHFFFAOYSA-N 2-hydroxy-3,4-dimethylbenzoic acid Chemical class CC1=CC=C(C(O)=O)C(O)=C1C YSJWNEDBIWZWOI-UHFFFAOYSA-N 0.000 description 2
- HQOBDLCAOWRBOU-UHFFFAOYSA-N 2-hydroxy-9H-carbazole-1-carboxylic acid Chemical class C12=CC=CC=C2NC2=C1C=CC(O)=C2C(=O)O HQOBDLCAOWRBOU-UHFFFAOYSA-N 0.000 description 2
- RNELSSOIEGVRNT-UHFFFAOYSA-N 2-hydroxydibenzofuran-1-carboxylic acid Chemical class O1C2=CC=CC=C2C2=C1C=CC(O)=C2C(=O)O RNELSSOIEGVRNT-UHFFFAOYSA-N 0.000 description 2
- VBHYTUXWVBNUBL-UHFFFAOYSA-N 3-hydroxy-1-benzothiophene-2-carboxylic acid Chemical class C1=CC=C2C(O)=C(C(=O)O)SC2=C1 VBHYTUXWVBNUBL-UHFFFAOYSA-N 0.000 description 2
- PHQKCVOZVPSTAF-UHFFFAOYSA-N 3-hydroxyanthracene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C=C(C(C(=O)O)=C3)O)C3=CC2=C1 PHQKCVOZVPSTAF-UHFFFAOYSA-N 0.000 description 2
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 2
- KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical compound C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 description 2
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 2
- NGOVEBFZPWAZCG-UHFFFAOYSA-N C1=CC2=C3C=CC=CC3=CC2=C2C1=CC=C(O)C2=O Chemical class C1=CC2=C3C=CC=CC3=CC2=C2C1=CC=C(O)C2=O NGOVEBFZPWAZCG-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 206010013647 Drowning Diseases 0.000 description 2
- ALNWQAFPXMGLTJ-UHFFFAOYSA-N N-(7-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=C(O)C=C2C(NC(=O)C)=CC=CC2=C1 ALNWQAFPXMGLTJ-UHFFFAOYSA-N 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N carbodiimide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
Definitions
- the present invention relates to compounds of the formula CtHs in which R is selected from the group consisting of H and RzCO and R and R2 are lower alkyl.
- the present invention is not limited to any particular method of preparing the compounds, but it has ben found that a very simple method is the condensation of 2,4-diphenyl-6-chloros-triazine with 2,5-dialkoxy-a-amino acyl anilides. The reaction proceeds smoothly and the free bases may be obtained by hydrolyzing oil the acyl roup by conventional means.
- the free bases may be readily diazotized and coupled without using any special techniques.
- azoic pigments may be obtained with various ice-color coupling components; fabrics may be padded with a coupling component and the color developed thereon; or diazoamino, or other stable compounds of the diazos may be prepared and incorporated into azoic printing pastes which are then developed conveniently by acid treatment.
- the particular lower alkyl group is not important and may be ethyl, methyl, propyl, or the like.
- the acyl group may be any of the lower fatty acid acyl groups, such as acetyl, propionyl, and the like. However, because of their cheapness and ready availability, the acetyl compounds are preferred.
- nents which may be used in the present invention are compounds such as beta-naphthol; 8-amino- 2-naphthol; 8-acetylamino-2-naphthol, benzyl naphthols, pyrazolones, hydroxybenzofluorenones, and the various N-substituted amides such as arylides of 2-hydroxy-3-naphthoic acid, of 2- hydroxy-3-anthroic acid, of methyl and dimethylsalicylic acids, of hydroxycarbazole carboxylic acids, of hydroxybenzocarbazole carboxylic acids, of hydroxybenzaoridone carboxylic acids, of hydroxydibenzofuran carboxylic acids, of hydroxybenzothiophene carboxylic acids, of acetoacetic acid, of benzoylacetic acid, and the like.
- Example 1 CaHs CZHEO N N NH0 0 CH1 CzHsO Examp e 2 C a I s CaHrL J-NH- N
- a mixture of 6.02 parts of the above prepared product and 21 parts of concentrated hydrochloric acid in '73 parts of butyl alcohol is refluxed until hydrolysis is complete, cooled, and filtered.
- the product is obtained in the form of its hydrochloride, which decomposes without melting above 250 C. This reaction can also be run in excellent yield in ethanol instead-of butanol.
- the hydrochloride is readily converted to the free base by dissolving in warm pyridine and drowning in water.
- Example 4 4 I claim: 1. A compound of the formula COH R O Celia-k )NH N w in which R is selected from the group consisting of H and- RzCO and R and R2 are lower alkyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented Sept. 7, 1954 2,688,616 FAST BASES OFCTHE TRIAZINE SERIES Frederick Brody, New York, N. Y., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application March 1, 1952, Serial No. 274,488
3 Claims.
1 The present invention relates to compounds of the formula CtHs in which R is selected from the group consisting of H and RzCO and R and R2 are lower alkyl.
In the past, it has been a considerable problem to obtain azoic coloring matters which have a greenish-blue shade. For the most part, the few coloring matters having the desired shade have been expensive and have had other unsatisfactory characteristics. When the free bases of the present invention, that is to say, where R is hydrogen, are diazotized and coupled with 2- hydroxy-3-naphthoic acid arylides, blue azo coloring matters of a very desirable green shade are obtained, which have good fastness and other properties. The compounds of the present invention are not limited to producing the greenishblue colors, although this is one of their important fields. 0n the contrary, other azocoloring matters of different shades may be obtained by coupling with different coupling components.
The present invention is not limited to any particular method of preparing the compounds, but it has ben found that a very simple method is the condensation of 2,4-diphenyl-6-chloros-triazine with 2,5-dialkoxy-a-amino acyl anilides. The reaction proceeds smoothly and the free bases may be obtained by hydrolyzing oil the acyl roup by conventional means.
It is an advantage of the present invention that the free bases may be readily diazotized and coupled without using any special techniques. For example, azoic pigments may be obtained with various ice-color coupling components; fabrics may be padded with a coupling component and the color developed thereon; or diazoamino, or other stable compounds of the diazos may be prepared and incorporated into azoic printing pastes which are then developed conveniently by acid treatment.
The particular lower alkyl group is not important and may be ethyl, methyl, propyl, or the like. The acyl group may be any of the lower fatty acid acyl groups, such as acetyl, propionyl, and the like. However, because of their cheapness and ready availability, the acetyl compounds are preferred.
Among the typical ice-color coupling compo- NHR nents which may be used in the present invention are compounds such as beta-naphthol; 8-amino- 2-naphthol; 8-acetylamino-2-naphthol, benzyl naphthols, pyrazolones, hydroxybenzofluorenones, and the various N-substituted amides such as arylides of 2-hydroxy-3-naphthoic acid, of 2- hydroxy-3-anthroic acid, of methyl and dimethylsalicylic acids, of hydroxycarbazole carboxylic acids, of hydroxybenzocarbazole carboxylic acids, of hydroxybenzaoridone carboxylic acids, of hydroxydibenzofuran carboxylic acids, of hydroxybenzothiophene carboxylic acids, of acetoacetic acid, of benzoylacetic acid, and the like.
This invention is further illustrated by the following examples. Where not otherwise specified, parts are by weight.
Example 1 CaHs CZHEO N N NH0 0 CH1 CzHsO Examp e 2 C a I s CaHrL J-NH- N A mixture of 6.02 parts of the above prepared product and 21 parts of concentrated hydrochloric acid in '73 parts of butyl alcohol is refluxed until hydrolysis is complete, cooled, and filtered. The product is obtained in the form of its hydrochloride, which decomposes without melting above 250 C. This reaction can also be run in excellent yield in ethanol instead-of butanol.
The hydrochloride is readily converted to the free base by dissolving in warm pyridine and drowning in water.
Ewamp e 3 05115 CzHxsO QBHEk J-WH on enactm- The above prepared base is diazotized in the ordinary way with hydrochloric acid and sodium nitrite and used to develop cotton cloth padded with 2-hydroxy-3-napthoic anilide. Blue dyeings are obtained of extremely greenish shade, and good fastness properties.
Example 4 4 I claim: 1. A compound of the formula COH R O Celia-k )NH N w in which R is selected from the group consisting of H and- RzCO and R and R2 are lower alkyl.
2. A compound of the formula N N NHCOCH:
CoHr-l )NH N CaHaO 3. A compound of the formula C0115 Q BO N N NE:
C oHs-k )NH- N References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,460,618 Bernasconi Feb. 1, 1949 2,513,264 Hansen June 27, 1950
Claims (1)
1. A COMPOUND OF THE FORMULA
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2688616A true US2688616A (en) | 1954-09-07 |
Family
ID=3440539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2688616D Expired - Lifetime US2688616A (en) | Fast bases of the triazine series |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2688616A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2774922A1 (en) * | 2013-03-04 | 2014-09-10 | Borealis Agrolinz Melamine GmbH | Method for obtaining a functionalized triazine compound and the triazine compound obtained by said method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2460618A (en) * | 1944-08-09 | 1949-02-01 | Ciba Ltd | Triazine azo dyes |
| US2513264A (en) * | 1950-06-27 | Triasine derivatives and methods of |
-
0
- US US2688616D patent/US2688616A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513264A (en) * | 1950-06-27 | Triasine derivatives and methods of | ||
| US2460618A (en) * | 1944-08-09 | 1949-02-01 | Ciba Ltd | Triazine azo dyes |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2774922A1 (en) * | 2013-03-04 | 2014-09-10 | Borealis Agrolinz Melamine GmbH | Method for obtaining a functionalized triazine compound and the triazine compound obtained by said method |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2688616A (en) | Fast bases of the triazine series | |
| US2725376A (en) | Ice colors of the quinoline series | |
| US2781345A (en) | 6-amino-7, 8-benzocarbostyrils | |
| US2173056A (en) | Dyes for cellulose esters and ethers | |
| US2877230A (en) | Pyrrocoline dyes | |
| US1522089A (en) | Azodyestuffs and process of making the same | |
| US2725377A (en) | Ice colors of the azole series | |
| US2695298A (en) | Fast bases of the azole series | |
| US2694713A (en) | Fast bases of the acridone series | |
| US2694714A (en) | Fast bases of the quinoline series | |
| US2690437A (en) | Azoic coloring matters of fast bases of the triazine series | |
| US2725375A (en) | Ice colors of the acridone series | |
| US3993441A (en) | 4-Nitro,2-alkylbenzene azo-3-cyano-4-methyl-6-hydroxy-2-pyridone dyeing of synthetic hydrophobic fibers | |
| US2130358A (en) | Azo compounds and process for coloring therewith | |
| US2149703A (en) | Azo dyes | |
| US2167142A (en) | Azo dyes | |
| US2040473A (en) | Azo dyestuffs and process of preparing the same | |
| DE2352858A1 (en) | HYDRO-INSOLUBLE MONOAZO DYES AND PROCESS FOR THEIR MANUFACTURING | |
| US3427119A (en) | Synthetic linear polyamides which have been colored with monoazo indole phthalimide dyes | |
| US2116355A (en) | Disazo dyestuffs and their production | |
| GB1504075A (en) | Pyrazole benzanilido disazo dyestuffs | |
| US2021911A (en) | Process for dyeing and printing | |
| US1929853A (en) | Azo dyestuff | |
| US1893991A (en) | Azo dyesttjffs on the fibeb and new compositions of matter | |
| DE2438497A1 (en) | AZO DYES |