GB1025060A - Improvements relating to ªÊ-hydroxyphenyl-úË-triazines and their use - Google Patents
Improvements relating to ªÊ-hydroxyphenyl-úË-triazines and their useInfo
- Publication number
- GB1025060A GB1025060A GB294764A GB294764A GB1025060A GB 1025060 A GB1025060 A GB 1025060A GB 294764 A GB294764 A GB 294764A GB 294764 A GB294764 A GB 294764A GB 1025060 A GB1025060 A GB 1025060A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- groups
- compounds
- cycloalkyl
- bis
- 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
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of formula <FORM:1025060/C2/1> in which X and Y represent H or an alkyl, alkenyl, cycloalkyl or aralkyl group which may be substituted and the benzene ring A may be substituted in the 31, 41 and 51 positions by halogen, alkyl, alkenyl or acyloxy groups or by cycloalkyl, aralkyl or aryl groups which may be further substituted. If X and/or Y are alkyl, the carbon chain may be interrupted by the groups-O-and-S-and may be substituted by hydroxyl amino, aryl or cycloalkyl groups or halogen atoms. The benzene ring A may be substituted by cycloalkyl, aralkyl or aryl groups further substituted by chlorine or bromine atoms; an acyloxy group derived from an aliphatic, cycloaliphatic or aromatic carboxylic acid which may carry a further carboxy, carbo-alkoxy or alkoxy group; or may carry a fused ring such as a tetramethylene group. The new compounds may be prepared by heating 1 mole of an amidine of formula <FORM:1025060/C2/2> and one mole of an amidine of formula <FORM:1025060/C2/3> with one mole of an o-hydroxybenzene carboxyic acid ester of formula <FORM:1025060/C2/4> in which R is a hydrocarbon radical which may be substituted. If desired, any reactive substituents in the new o-hydroxyphenyl-s-triazines can subsequently be altered as follows: if X or Y is an alkoxyalkyl group it can be converted by HBr to a bromoalkyl group; exchangeable halogen can be converted to hydroxy by treatment with sodium hydroxide, to ether groups by treatment with alkali alcoholates or phenolates, to amino groups by treatment with ammonia or a primary or secondary amine; and alcoholic or phenolic hydroxy groups can be esterified or etherified. The acyloxy groups in the benzene ring A may be introduced by acylation of the corresponding hydroxy compounds. Examples are given of the preparation of the following compounds: (a) 2-(21-hydroxyphenyl) - 4,6 - dimethyl - s - triazine unsubstituted carrying the following substituents on the benzene ring: 51-methyl; 51-cyclohexyl; 51 - 111,111,311,311 - tetramethylbutyl; 31,51-dimethyl; 4,51-dimethyl; 51-benzyl; 51-phenyl; 31-phenyl; 51-chloro; 51-tert.-butyl; 31,51-dichloro; 31-chloro-51-methyl; 31-allyl-51-methyl; 41-acetoxy; 41-butyroyl; 41-methoxycarboxy; 41-cyclohexyloxycarboxy; 41-lauroyloxy; 41-b -carboxy - acryloyloxy; and #z - carbethoxy-valeroyl; and 2-(21-hydroxyphenyl)-s-triazin unsubstituted and carrying the following substituents on the triazine ring: 4,6-didecyl; 4,6-diethyl; 4,6-dimonyl; 4,6-diheptadecyl; 4,6-dipropyl; 4,6-dichloromethyl; 4,6-dibutyl; 4,6-bis - b - methoxyethyl; 4,6 - bis - b - methylmer-captoethyl; 4,6 - bis - b - dimethylaminoethyl; 4,6 - bis - (211 - phenyl - D 111 - propenyl); 4,6-bis - b - phenylvinyl and 4,6 - bis - b - phenylethyl.ALSO:New 0-hydroxyphenyl-s-triazines of formula <FORM:1025060/C3/1> in which X and Y represent H or an alkyl, alkenyl, cycloalkyl or aralkyl group which may be substituted and the benzene ring A may be substituted in the 31, 41 and 51 position by halogen, alkyl, alkenyl or acyloxy groups or by cycloalkyl, aralkyl or aryl groups which may be further substituted 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 lactanes, 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; (e) condensation polymers subsequently cross-linked by addition polymerization, e.g. co-polymers of polyesters of unsaturated carbooxylic acids with polyhydric alcohols modified by dicarboxylic acids or vinyl or vinylidene monomers. They may also be incorporated 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 made from a composition comprising also dibutyl phthalate and acetone (Ex. 11); (b) a polyester resin produced by adding a mixture of maleic anhydride and tetrachlorophthalic 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 (Ex. 12); (c) methyl methacrylate polymerized in the presence of lauroyl peroxide (Ex. 13); (d) a copolymer of polyvinyl chloride and dioctyl phthalate (Ex. 14); (e) polyethylene or polypropylene (Ex. 15); (f) polycaprolactam or polyhexamethylene adipamide (Ex. 16); and (g) a lacquer comprising cellulose acetobutyrate, dimethyl glycol phthalate, methyl alcohol, toluene, a triazine derivative and acetone (Ex. 17).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH84363A CH388249A (en) | 1963-01-24 | 1963-01-24 | Process for protecting textile material against photodamage |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1025060A true GB1025060A (en) | 1966-04-06 |
Family
ID=4196493
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB294764A Expired GB1025060A (en) | 1963-01-24 | 1964-01-23 | Improvements relating to ªÊ-hydroxyphenyl-úË-triazines and their use |
Country Status (7)
Country | Link |
---|---|
AT (2) | AT246151B (en) |
CH (1) | CH388249A (en) |
DE (1) | DE1240084B (en) |
ES (1) | ES295660A1 (en) |
GB (1) | GB1025060A (en) |
NL (1) | NL139175B (en) |
SE (1) | SE328895B (en) |
-
1963
- 1963-01-24 CH CH84363A patent/CH388249A/en unknown
- 1963-12-31 NL NL302933A patent/NL139175B/en unknown
-
1964
- 1964-01-23 GB GB294764A patent/GB1025060A/en not_active Expired
- 1964-01-23 AT AT54164A patent/AT246151B/en active
- 1964-01-23 AT AT43965A patent/AT254149B/en active
- 1964-01-23 DE DE1964G0039681 patent/DE1240084B/en active Granted
- 1964-01-23 SE SE83464A patent/SE328895B/xx unknown
- 1964-01-23 ES ES295660A patent/ES295660A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AT246151B (en) | 1966-04-12 |
CH84363A4 (en) | 1964-11-14 |
AT254149B (en) | 1967-05-10 |
ES295660A1 (en) | 1964-07-16 |
DE1240084C2 (en) | 1967-11-23 |
SE328895B (en) | 1970-09-28 |
NL139175B (en) | 1973-06-15 |
CH388249A (en) | 1965-06-15 |
DE1240084B (en) | 1967-05-11 |
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