GB1019118A - Improvements relating to ú´-hydroxyphenyl-ú¾-triazines and their use - Google Patents
Improvements relating to ú´-hydroxyphenyl-ú¾-triazines and their useInfo
- Publication number
- GB1019118A GB1019118A GB294964A GB294964A GB1019118A GB 1019118 A GB1019118 A GB 1019118A GB 294964 A GB294964 A GB 294964A GB 294964 A GB294964 A GB 294964A GB 1019118 A GB1019118 A GB 1019118A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- group
- compounds
- formula
- substituted
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
- G03C1/8155—Organic compounds therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
- C11B5/0064—Heterocyclic compounds containing nitrogen in the ring
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Optics & Photonics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Paints Or Removers (AREA)
Abstract
New o-hydroxyphenyl-s-triazines of formula <FORM:1019118/C3/1> in which one of X and Y represents a monovalent aromatic radical of formula <FORM:1019118/C3/2> in which R1 and R2 represent hydrogen or halogen or an alkyl, aralkyl, alkoxy or acyloxy group and the other of X and Y represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl group which may be substituted and in which the benzene rings A and B may be further substituted in the 3, 4 and 5 positions by alkyl, alkenyl, cycloalkyl, aralkyl or aryl groups, halogens, or free etherified or esterified hydroxyl groups, are used for improving the stability of light-sensitive organic materials. They may be incorporated, for example, in thermoplastic or thermosetting addition or condensation polymers, e.g. (a) homopolymers and copolymers of vinyl and vinylidine compounds, epoxides, particularly bisepoxides, lactams and lactones, and aldehydes; (b) reaction products of isocyanates with hydroxyl and/or amino compounds or with polyesters and/or polyethers; (c) linear condensation products derived from dicarboxylic acids and dihydroxy compounds; (d) cross-linked polycondensates obtained by the condensation of aldehydes with compounds such as ureas, phenols and melamines; and (e) condensation polymers subsequently cross-linked by addition polymerization, e.g. copolymers of polyesters of unsaturated carboxylic acids with polyhydric alcohols modified by dicarboxylic acids or vinyl or vinylidine monomers. They may also be incorated in natural polysaccharides which may be modified, such as cellulose and cellulose esters. Examples are given of the use of the new compounds in stabilizing the following compositions: (a) cellulose acetate films (Example 9); (b) a polyester resin produced by adding a mixture of maleic anhydride and tetrachlorphthalic acid anhydride (or phthalic anhydride) to a mixture of ethylene glycol and diethylene glycol and treating the polyester so produced with styrene or methyl methacrylate (Example 10); (c) methyl methacrylate polymerized in the presence of lauroyl peroxide (Example 11); (d) a copolymer of polyvinyl chloride and dioctyl phthalate (Example 12); (e) polyethylene or polypropylene (Example 13); (f) polycaprolactam or polyhexamethylene adipamide (Example 14); and (g) a lacquer comprising cellulose acetobutyrate, dimethyl glycol phthalate, methyl alcohol and acetone (Example 15).ALSO:The invention comprises o-hydroxyphenyl-s-triazines of formula <FORM:1019118/C2/1> in which one of X and Y represents a monovalent aromatic radical of formula <FORM:1019118/C2/2> in which R1 and R2 represent hydrogen, halogen or an alkyl, aralkyl, alkoxy or acyloxy group and the other of X and Y represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl group, the benzene rings A and B being optionally further substituted in the 3-, 4- and 5-positions by alkyl, alkenyl, cycloalkyl, aralkyl or aryl groups, free, etherified or acylated hydroxyl groups, or by halogens. When X or Y is alkyl it may be substituted by halogen or have the formula -alkylene-E-D1 in which the alkylene group has 1-12 carbon atoms and E is -O-, -S-, or -N(D2)-. D1 and D2 represen alkyl radicals and if E is oxygen or nitrogen D1 or D2 can also be hydrogen. If X or Y is alkenyl it may be substituted by aryl groups. The new compounds may be prepared by heating 1 mole of an oxazine compound of formula <FORM:1019118/C2/3> with one mole of an amidine of formula <FORM:1019118/C2/4> Preferably the reaction is carried out in boiling organic solvents, for example methanol, ethanol, ethylene glycol monomethyl or monoethyl ether and dioxan. Reactive substituents in the new compounds may be replaced by other groups. For example if X or Y is an alkoxyalkyl group it may be converted by treatment with HBr into the corresponding bromoalkyl group. A halogen radical may be replaced by a hydroxyl group, an ether group or an amino group by reaction with aqueous sodium hydroxide, alkali alcoholates or phenates, or with primary or secondary amines respectively. Compounds which have alcoholic or phenolic hydroxyl groups may be esterified or etherified. Compounds containing alkenyl groups may be produced by splitting off hydrogen halide, water, alcohol or an amine from a halogenoalkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl derivative respectively. Examples are given of the preparation of compounds of the above general formula in which A carries only an OH substituent and also in which it is additionally substituted by alkyl, chlorine, alkoxy or aralkoxy and X and Y are H, phenyl; phenyl-substituted by alkoxy, chlorine, bromine or alkyl; alkyl; an alkyl group interrupted by sulphur; dialkylaminoalkyl; benzyl; alkoxyalkyl; alkyl substituted by free or esterified carboxyl groups; or cycloalkyl; at least one of the groups X and Y being a group <FORM:1019118/C2/5> as defined above. The oxazimes used as starting materials may be prepared by splitting off water from compounds of formula <FORM:1019118/C2/6> or <FORM:1019118/C2/7> in which the benzene rings may carry additional substituents as specified above for the benzene nucleus A.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH84563A CH388251A (en) | 1963-01-24 | 1963-01-24 | Process for protecting textile material against photodamage |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1019118A true GB1019118A (en) | 1966-02-02 |
Family
ID=4196539
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB294964A Expired GB1019118A (en) | 1963-01-24 | 1964-01-23 | Improvements relating to ú´-hydroxyphenyl-ú¾-triazines and their use |
Country Status (9)
Country | Link |
---|---|
AT (2) | AT246148B (en) |
BE (1) | BE661188A (en) |
BR (1) | BR6456357D0 (en) |
CH (1) | CH388251A (en) |
DE (1) | DE1240862B (en) |
ES (1) | ES295662A1 (en) |
FR (1) | FR1380271A (en) |
GB (1) | GB1019118A (en) |
SE (1) | SE325898B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111701458B (en) * | 2020-06-16 | 2022-02-15 | 北京工业大学 | Preparation method of covalent triazine framework organic solvent nanofiltration membrane |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH350763A (en) * | 1958-10-14 | 1960-12-15 | Ciba Geigy | Use of azole compounds as a protective agent against ultraviolet radiation |
NL275368A (en) * | 1961-03-06 |
-
1963
- 1963-01-24 CH CH84563A patent/CH388251A/en unknown
-
1964
- 1964-01-23 GB GB294964A patent/GB1019118A/en not_active Expired
- 1964-01-23 FR FR961336A patent/FR1380271A/en not_active Expired
- 1964-01-23 SE SE83664A patent/SE325898B/xx unknown
- 1964-01-23 BR BR15635764A patent/BR6456357D0/en unknown
- 1964-01-23 AT AT53864A patent/AT246148B/en active
- 1964-01-23 DE DE1964G0039683 patent/DE1240862B/en active Granted
- 1964-01-23 ES ES295662A patent/ES295662A1/en not_active Expired
- 1964-01-23 AT AT44065A patent/AT254832B/en active
-
1965
- 1965-03-16 BE BE661188D patent/BE661188A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
CH84563A4 (en) | 1964-11-14 |
FR1380271A (en) | 1964-11-27 |
DE1240862C2 (en) | 1967-11-30 |
AT246148B (en) | 1966-04-12 |
AT254832B (en) | 1967-06-12 |
DE1240862B (en) | 1967-05-24 |
CH388251A (en) | 1965-06-15 |
BR6456357D0 (en) | 1973-07-17 |
SE325898B (en) | 1970-07-13 |
BE661188A (en) | 1965-07-16 |
ES295662A1 (en) | 1964-07-16 |
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