GB1016365A - New azolyl-thiophene derivatives, process for their preparation and their use - Google Patents
New azolyl-thiophene derivatives, process for their preparation and their useInfo
- Publication number
- GB1016365A GB1016365A GB4693863A GB4693863A GB1016365A GB 1016365 A GB1016365 A GB 1016365A GB 4693863 A GB4693863 A GB 4693863A GB 4693863 A GB4693863 A GB 4693863A GB 1016365 A GB1016365 A GB 1016365A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- residue
- carboxylic
- phenyl
- formula
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Azolyl-thiophene compounds of Formula (1) <FORM:1016365/C3/1> in which R1 is a benzene or naphthalene residue; R is a thiophene residue linked in position 2 with R1 and position 5 with the azole ring; X represents-O-,-S-,-NH-or -NA- in which A is an alkyl, alkenyl, hydroxyalkyl or cyanoalkyl group containing up to 4 carbon atoms or an aralkyl or carboxylacyl group; and R2 is a benzene or naphthalene residue linked to the azole ring as shown and carrying at least one carboxylic group (or a functionally converted carboxylic group retaining the <FORM:1016365/C3/2> group) linked directly to a carbon atom of the aromatic nucleus, are used for optically brightening synthetic fibres, particularly polyester fibres and polyamide fibres. They may be added to the reaction mixtures before or during the polymerization leading to the formation of the polyesters and polyamides. Examples are given of the use of the new compounds in brightening (a) a polyester granulate of polyterephthalic acid ethylene glycol ester and (b) a polyamide prepared from hexamethylene diamine adipate.ALSO:The invention comprises azolyl-thiophene compounds of formula <FORM:1016365/C2/1> in which R1 is a benzene or naphthalene residue; R is a thiophene residue linked in position 2 with R1 and position 5 with the azole ring; X represents -O-, -S-, -NH-or -NA-, in which A is an alkyl, alkenyl, hydroxyalkyl or cyanoalkyl group containing up to 4 carbon atoms or an aralkyl or carboxylic acyl group; and R2 is a benzene or naphthalene residue linked to the azole ring as shown and carrying at least one carboxylic group (or a functionally converted carboxylic group retaining the >C = O group) linked directly to a carbon atom of the aromatic nucleus. The nucleus R2 may carry other substituents, e.g. C1-C4 alkyl groups, in addition to the carboxylic group, and the nucleus R1 may also carry substituents, e.g. a halogen atom, a C1-C4 alkyl or alkoxy group. The functionally converted carboxylic group attached to the residue R2 may be an amide, hydrazide or ester group. The new compounds may be prepared by reacting a carboxylic acid of formula R1-R-COOH at elevated temperature and preferably in the presence of a condensation catalyst with an amino compound of the formula <FORM:1016365/C2/2> and the residue R2 carrying an ester group which may be hydrolysed or converted into another functionally modified carboxylic acid group. The new compounds are useful as optical brightening agents for synthetic fibres and are added to the reaction mixtures before or during polymerization or polycondensation. Examples are given of the preparation of compounds of the above general formula in which X is the group -O-; R1 is phenyl, 4-methoxy-phenyl, 4-methyl phenyl, or 4-chloro-2,5-di-methoxy phenyl and R2 is a phenyl residue carrying the group -COB, in which B is hydroxy, methoxy, N-morpholinyl, phenylamino, 2,5 - dimethoxy - 4 - chlorophenylamino -, b - hydroxyethylamino -, allylamino -, NH2, allyloxy, benzyloxy, p-tolyloxy, isopropyloxy, 2 - ethylhexyloxy -, n - hexadecyloxy, and -OCH2CH2OCH2CH2OCH2CH2 CH2CH3.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH848161A CH412312A (en) | 1961-07-19 | 1961-07-19 | Use of new azolyl-thiophene derivatives as optical brighteners for non-textile organic materials |
FR903875A FR1335174A (en) | 1961-07-19 | 1962-07-13 | New azolyl-thiofenes for use as optical brighteners and process for their preparation |
GB27631/62A GB990397A (en) | 1961-07-19 | 1962-07-18 | New azolylthiophene compounds useful as optical brightening agents and process for their production |
DE1962C0027492 DE1238873B (en) | 1961-07-19 | 1962-07-18 | Optical brighteners |
CH1505862A CH450421A (en) | 1962-12-21 | 1962-12-21 | Process for the preparation of azolyl thiophene compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1016365A true GB1016365A (en) | 1966-01-12 |
Family
ID=27509336
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4693863A Expired GB1016365A (en) | 1961-07-19 | 1963-11-27 | New azolyl-thiophene derivatives, process for their preparation and their use |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1016365A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110086817A1 (en) * | 2008-05-30 | 2011-04-14 | University Of Notre Dame Du Lac | Anti-bacterial agents from benzo[d]heterocyclic scaffolds for prevention and treatment of multidrug resistant bacteria |
-
1963
- 1963-11-27 GB GB4693863A patent/GB1016365A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110086817A1 (en) * | 2008-05-30 | 2011-04-14 | University Of Notre Dame Du Lac | Anti-bacterial agents from benzo[d]heterocyclic scaffolds for prevention and treatment of multidrug resistant bacteria |
US8362268B2 (en) * | 2008-05-30 | 2013-01-29 | University Of Notre Dame Du Lac | Anti-bacterial agents from benzo[d]heterocyclic scaffolds for prevention and treatment of multidrug resistant bacteria |
US9617249B2 (en) | 2008-05-30 | 2017-04-11 | University Of Notre Dame Du Lac | Benzoheterocyclic anti-bacterial agents |
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