GB835892A - Manufacture of diaryloxazole derivatives - Google Patents
Manufacture of diaryloxazole derivativesInfo
- Publication number
- GB835892A GB835892A GB18680/56A GB1868056A GB835892A GB 835892 A GB835892 A GB 835892A GB 18680/56 A GB18680/56 A GB 18680/56A GB 1868056 A GB1868056 A GB 1868056A GB 835892 A GB835892 A GB 835892A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- formula
- ethylene
- alkyl group
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
- C07D263/64—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polarising Elements (AREA)
Abstract
The invention comprises a process for making diaryloxazoles of formula <FORM:0835892/IV (b)/1> in which R1 and R2 are aryl residues and R3\t is an organic bridge member with at least one double bond between two carbon atoms, and also the new compounds of the above formula in which R1 and R2 contain at least one alkyl group having up to 4 carbon atoms and in at least one of the residues R1 and R2 the alkyl group or groups contain a total of at least 2 carbon atoms. The diaryl oxazoles are made by heating a compound of formula <FORM:0835892/IV (b)/2> with an agent that splits off water, e.g. sulphur trioxide or zinc chloride, to a temperature in the range 140-180 DEG C. When sulphur trioxide is used sulphonation also takes place. The starting materials are obtained by condensing dihalides of unsaturated dicarboxylic acids, e.g. thiophene-2,5-dicarboxylic acid, with primary aryl amines having an hydroxyl group in the ortho position to the amino group, in accordance with the process described and claimed in Specification 835,891. Examples are given of the preparation of the compounds of formul <FORM:0835892/IV (b)/3> a ,b - di - [5 - methylbenzoxazolyl - (2)] - ethylene disulphonic acid and its sodium salt, a ,b -di-[benzoxazolyl-(2)]-ethylene disulphonic acid, and <FORM:0835892/IV (b)/4> The products are optical brightening agents (see Group IV (c)), and may be used in the treatment of paper and cardboard (see Group VIII) and acetyl cellulose films (see Group IV (a)).ALSO:Diaryloxazoles of formula <FORM:0835892/IV(c)/1> in which R1 and R2 are aryl residues and R3 an organic bridge member with at least one double bond between 2 carbon atoms are made by heating a compound of formula <FORM:0835892/IV(c)/2> with an agent that splits off water, e.g. sulphur trioxide or zinc chloride, to a temperature in the range 140-180 DEG C. When sulphur trioxide is used sulphonation also takes place. Compounds in which R1 and R2 contain at least one alkyl group having up to 4 carbon atoms, the alkyl group or groups containing at least 2 carbon atoms, are claimed per se. The products are brightening agents. Examples are given of the preparation of <FORM:0835892/IV(c)/3> a .b - di - [5 - methylbenzoxazolyl - (2)] - ethylene disulphonic acid and its sodium salt, a .b -di-[benzoxazolyl-(2)]-ethylene disulphonic acid and <FORM:0835892/IV(c)/4>ALSO:Compounds of the formula <FORM:0835892/IV (a)/1> in which R1 and R2 are aryl residues and R3\t an organic bridge member with at least one double bond between 2 carbon atoms, are used for the optical brightening of nitro cellulose lacquers and acetyl cellulose films. In an example 0.25 part of a -b -di-[5-methylbenzoxazolyl - (2)] - ethylene is added to 100 parts of an acetyl cellulose mass containing 24% of acetyl cellulose. The film produced from this mass has a brighter appearance than one containing no oxazole compound.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH835892X | 1955-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB835892A true GB835892A (en) | 1960-05-25 |
Family
ID=4540715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18680/56A Expired GB835892A (en) | 1955-06-17 | 1956-06-15 | Manufacture of diaryloxazole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB835892A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118883A (en) * | 1964-01-21 | Chi-chj | ||
| US3147253A (en) * | 1961-06-17 | 1964-09-01 | Hodogaya Chemical Co Ltd | Process for manufacturing alpha, betadi-[aryloxazolyl-(2)]-ethylene |
| US3178421A (en) * | 1960-01-09 | 1965-04-13 | Governor Of Osaka Prefecture | Novel bis-aryloxazolyl ethylene optical brightening derivatives |
-
1956
- 1956-06-15 GB GB18680/56A patent/GB835892A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118883A (en) * | 1964-01-21 | Chi-chj | ||
| US3178421A (en) * | 1960-01-09 | 1965-04-13 | Governor Of Osaka Prefecture | Novel bis-aryloxazolyl ethylene optical brightening derivatives |
| US3147253A (en) * | 1961-06-17 | 1964-09-01 | Hodogaya Chemical Co Ltd | Process for manufacturing alpha, betadi-[aryloxazolyl-(2)]-ethylene |
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