GB846908A - Light-sensitive polyesters and photographic reproduction processes employing them - Google Patents
Light-sensitive polyesters and photographic reproduction processes employing themInfo
- Publication number
- GB846908A GB846908A GB3608756A GB3608756A GB846908A GB 846908 A GB846908 A GB 846908A GB 3608756 A GB3608756 A GB 3608756A GB 3608756 A GB3608756 A GB 3608756A GB 846908 A GB846908 A GB 846908A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- malonate
- alpha
- reacting
- acids
- 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
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6858—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6888—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials For Photolithography (AREA)
Abstract
A light-sensitive polyester is made by polyesterifying a dihydric compound of formula HO-R-OH, where R is a bifunctional group containing 2-12 carbon atoms and a substituted malonic acid of formula: <FORM:0846908/IV(a)/1> where R1 is a radical free of constituents which are functional in the polyesterification reaction and R11 is a hydrogen atom or a lower alkyl group, or R11 and R1 together represent the atoms necessary to complete a nucleus, having another double bond conjugated with that between CR11 and R1. Instead of using the free acids, their ester-forming derivatives may be used, e.g. the di- or mono-esters, the dichlorides, the monochlorides-monoesters or the ammonium or amine salts. Specified dihydric compounds are ethylene-, diethylene-, triethylene-, 1:3-propylene-, 1:2-propylene-, 1:4-butylene-, 2:3-butylene-, 1:5-pentylene-, 2:2-dimethyl-1:3-propylene-, decamethylene- and dodecame-thylene-glycols; also p-dihydroxymethylbenzene and hydroquinone. Specified dicarboxylic acids are cinnamylidene-, crotonylidene-, gamma-methylcrotonylidene-, o-nitrocinnamylidene-, naphthylallylidene-, 2-furfucylidene-, N-methyl-pyridylidene-2-ethylidene-, N-methylquinolidene-2-ethylidene-, N-methylbenzothiazolylidene-, p-dimethylaminocinnamylidene-, alpha-furylally-lidene- and sulphonated 2-pentenylidene malonic acids. Catalysts for the polyesterification reaction are sulphuric and p-toluene sulphonic acids (when using free acids) and butyl titanate or antimony oxide (when using esters of the acids). Those polyesters containing nitrogen may be quarternized by heating with a dialkyl sulphate, an alkyl sulphonate, methyl iodide, benzyl iodide or allyl iodide but the quarternized polyesters revert to their unquarternized form when heated to about 100 DEG C. The polyesters are soluable in organic solvents (e.g. acetone, 2-methoxylethyl acetate, methylglycol acetate, 2-methoxy-ethanol, aldehydes, aromatic solvents, methylene chloride or trichloroethylene) and those containing sulphonate or quartenary ammonium groups are soluble in water. On exposure to light, however, they become insoluble and may then be used for photographic purposes (see Group XX). When thus used, they may be applied to a backing dissolved in a solvent together if desired with a sensitizer (many specified) or a lacquer resin (e.g. polymethyl methacrylate or an alkyd resin). The polyester may also be used as a dielectric or as a support for pigments or dyes. Specifications 713,947, 717,708, 717,710, 717,711, 717,712 and 743,455 are referred to.ALSO:The Specification contains examples describing the preparation of certain 2-propenylidene malonic compounds as follows:- (2) Ethyl cinnamylidene malonate is made by refluxing a mixture of ethyl malonate, cinnamaldehyde and acetic anhydride ; (6) Ethyl crotonylidene malonate is made by refluxing a mixture of ethyl malonate, crotonaldehyde, methylene chloride and piperidine ; (7)-(10) Ethyl gamma-methylcrotonylidene malonate, ethyl o-nitrocinnamylidene malonate, ethyl naphthylalkylidene malonate and ethyl alpha-furylallylidene malonate are similarly prepared but using tiglic aldehyde, o-nitrocinnamaldehyde, alpha-naphthylacrolein or alpha-furanacrolein respectively instead of crotonaldehyde ; (11) Ethyl N-methylpyridylidene-2-ethylidenemalonate is made by first reacting methyl sulphate with alpha-picolene, then adding ethyl ethoxymethylenemalonate and alcoholic caustic soda solution and further reacting ; (12) Ethyl N-methylquinolylidene-2-ethylidene malonate is made by first reacting quinaldine with methyl p-toluenesulphonate and then heating the product with ethyl ethoxymethylene malonate and pyridine ; (13) Ethyl-N-methylbenzothiazolylidene- 2-ethylidene malonate is made by refluxing a mixture of 2-methylbenzothiazole methyl iodide, ethyl ethoxymethylene malonate and pyridine ; (17) Ethyl p-dimethylaminocinnamylidene malonate is made by refluxing a mixture of p-dimethylaminocinnamaldehyde, ethyl malonate, benzene and piperidine. a N-aphthaldehyde is obtained by reacting a -chloromethyl naphthalene with aqueous KI and hexa methylene tetramine in acetic acid under reflux ; p-dimethylamino cinnamaldehyde is obtained, by reacting the corresponding benzaldehyde with paraldehyde at below 0 DEG C. and then neutralising with aqueous sodium carbonate. Specifications 713,947, 717,708, 717,710, 717,711, 717,712, and 743,455 are referred to.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR703230 | 1955-11-24 | ||
FR57858 | 1956-10-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB846908A true GB846908A (en) | 1960-08-31 |
Family
ID=26169984
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3608756A Expired GB846908A (en) | 1955-11-24 | 1956-11-26 | Light-sensitive polyesters and photographic reproduction processes employing them |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE552657A (en) |
DE (1) | DE1182061B (en) |
FR (2) | FR1137056A (en) |
GB (1) | GB846908A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4588807A (en) * | 1983-10-26 | 1986-05-13 | Bayer Aktiengesellschaft | Benzylidenemalonic or vinylogous benzylidenemalonic acid polyesters, their preparation and their use for the UV stabilization of thermoplastics |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1099732B (en) * | 1958-08-18 | 1961-02-16 | Bayer Ag | Process for the production of polycarbonates with -CH = CH-CO groups which crosslink under the action of actinic light and which become poorly soluble or insoluble |
NL297153A (en) * | 1962-12-07 | |||
CA1275538C (en) * | 1985-08-16 | 1990-10-23 | Wayne P. Pruett | Colored unsaturated polyester material containing copolymerized methine dyes, and products therefrom |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE903529C (en) * | 1951-09-01 | 1954-02-08 | Kalle & Co Ag | Photosensitive layers |
US2706725A (en) * | 1951-09-13 | 1955-04-19 | Eastman Kodak Co | Polymers of vinyl benzal acetophenones |
-
0
- BE BE552657D patent/BE552657A/xx unknown
-
1955
- 1955-11-24 FR FR1137056D patent/FR1137056A/en not_active Expired
-
1956
- 1956-10-24 FR FR70498D patent/FR70498E/en not_active Expired
- 1956-11-24 DE DEE13275A patent/DE1182061B/en active Pending
- 1956-11-26 GB GB3608756A patent/GB846908A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4588807A (en) * | 1983-10-26 | 1986-05-13 | Bayer Aktiengesellschaft | Benzylidenemalonic or vinylogous benzylidenemalonic acid polyesters, their preparation and their use for the UV stabilization of thermoplastics |
Also Published As
Publication number | Publication date |
---|---|
FR1137056A (en) | 1957-05-23 |
BE552657A (en) | |
FR70498E (en) | 1959-05-06 |
DE1182061B (en) | 1964-11-19 |
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