GB949181A - Method of protecting material from ultra violet light - Google Patents
Method of protecting material from ultra violet lightInfo
- Publication number
- GB949181A GB949181A GB1757860A GB1757860A GB949181A GB 949181 A GB949181 A GB 949181A GB 1757860 A GB1757860 A GB 1757860A GB 1757860 A GB1757860 A GB 1757860A GB 949181 A GB949181 A GB 949181A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- cooh
- hydroxy
- cox
- group
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- -1 R1 is CN Chemical group 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 3
- 125000001302 tertiary amino group Chemical group 0.000 abstract 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229930005346 hydroxycinnamic acid Natural products 0.000 abstract 2
- DEDGUGJNLNLJSR-UHFFFAOYSA-N hydroxycinnamic acid group Chemical class OC(C(=O)O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 abstract 2
- 235000010359 hydroxycinnamic acids Nutrition 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 229920001225 polyester resin Polymers 0.000 abstract 2
- 239000004645 polyester resin Substances 0.000 abstract 2
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- 239000001856 Ethyl cellulose Substances 0.000 abstract 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000020 Nitrocellulose Substances 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- 240000008548 Shorea javanica Species 0.000 abstract 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000012461 cellulose resin Substances 0.000 abstract 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 abstract 1
- 230000006866 deterioration Effects 0.000 abstract 1
- 229920001249 ethyl cellulose Polymers 0.000 abstract 1
- 229960004667 ethyl cellulose Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 229920001220 nitrocellulos Polymers 0.000 abstract 1
- 229940079938 nitrocellulose Drugs 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
-
- 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)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cellulose or synthetic resin compositions contain ultra-violet light absorbing compounds of the general formula: Ar-CR3=CR1R2 wherein Ar is a phenyl group substituted by one or more hydroxy or alkoxy groups, R1 is CN, COOH, COX (where X is an alkyl, alkoxy or primary, secondary or tertiary amino group), (CH2)nCOOH or (CH2)nCOOR (where R1 i alkyl and n is 1 to 4), R2 is H, aryl, CN, COX or COOH, and R3 is H or an alkyl group. In Example 1, 4-hydroxy -a - acetyl-cinnamic acid anilide is added to a solution of damar and ethyl- or nitro-cellulose in toluene and the solution case to form a film. In Examples 2 and 3, stabilized polyester resins are obtained by esterifying a mixture of maleic anhydride and phthalic anhydride in known manner with ethylene glycol, mixing the resulting polyester resin with styrene and p-hydroxy -a - cyanocinnamic acid ethyl ester or p-hydroxy -a -cyano-b -methyl cinnamic acid ethyl ester, and polymerizing with benzoyl peroxide.ALSO:Lacquers contain ultra-violet light absorbing compounds of the formula Ar-CR3=CR1R2 wherein Ar is a phenyl group substituted by one or more hydroxy or alkoxy groups, R1 is CN, COOH, COX (where X is an alkyl, alkoxy or primary, secondary or tertiary amino group), (CH2)nCOOH or (CH2)nCOOR (where R is alkyl and n is 1 to 4), R2 is H, aryl, CN, COX or COOH, and R3 is H or an alkyl group. Many compounds are specified including hydroxycinnamic acids and its esters, amides and nitriles. The group Ar also may contain alkyl and halogen substitutents.ALSO:Textiles are protected against deterioration under the action of ultra-violet light by treating them with compounds of the formula: Ar-CR3 = CR1R2 wherein Ar is a phenyl group substituted by one or more hydroxy or alkoxy groups, R1 is CN, COOH, COX (where X is an alkyl, alkoxy or primary, secondary or tertiary amino group), (CH2)n COOH or (CH2)n COOR (where R is alkyl and n is 1 to 4), R2 is H, aryl, CN, COX or COOH, and R3 is H or an alkyl group. Many compounds are specified including hydroxy-cinnamic acids and its esters, amides and nitriles. The group Ar also may contain alkyl and halogen substituents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1757860A GB949181A (en) | 1960-05-18 | 1960-05-18 | Method of protecting material from ultra violet light |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1757860A GB949181A (en) | 1960-05-18 | 1960-05-18 | Method of protecting material from ultra violet light |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB949181A true GB949181A (en) | 1964-02-12 |
Family
ID=10097635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1757860A Expired GB949181A (en) | 1960-05-18 | 1960-05-18 | Method of protecting material from ultra violet light |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB949181A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057881A2 (en) * | 1981-02-05 | 1982-08-18 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | An anti-inflammatory, analgesic, and antipyretic pharmaceutical composition, and method for producing it |
| WO1993005443A1 (en) * | 1991-08-29 | 1993-03-18 | Eastman Kodak Company | Radiographic element |
| WO1993005444A1 (en) * | 1991-08-29 | 1993-03-18 | Eastman Kodak Company | Radiographic element |
| JP2005503365A (en) * | 2001-07-16 | 2005-02-03 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Photostable organic sunscreen compounds having antioxidant properties and compositions obtained therefrom |
| EP2168634A3 (en) * | 2002-09-13 | 2010-04-21 | Kao Corporation | Hair dye composition comprising methine dye |
| WO2012078544A3 (en) * | 2010-12-06 | 2012-08-02 | Sytheon Ltd. | Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers |
| WO2012078546A3 (en) * | 2010-12-06 | 2012-08-02 | Sytheon Ltd. | Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds |
-
1960
- 1960-05-18 GB GB1757860A patent/GB949181A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057881A2 (en) * | 1981-02-05 | 1982-08-18 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | An anti-inflammatory, analgesic, and antipyretic pharmaceutical composition, and method for producing it |
| EP0057881A3 (en) * | 1981-02-05 | 1982-09-01 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | An anti-inflammatory, analgesic, and antipyretic pharmaceutical composition, and method for producing it |
| WO1993005443A1 (en) * | 1991-08-29 | 1993-03-18 | Eastman Kodak Company | Radiographic element |
| WO1993005444A1 (en) * | 1991-08-29 | 1993-03-18 | Eastman Kodak Company | Radiographic element |
| JP2005503365A (en) * | 2001-07-16 | 2005-02-03 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Photostable organic sunscreen compounds having antioxidant properties and compositions obtained therefrom |
| EP2168634A3 (en) * | 2002-09-13 | 2010-04-21 | Kao Corporation | Hair dye composition comprising methine dye |
| WO2012078544A3 (en) * | 2010-12-06 | 2012-08-02 | Sytheon Ltd. | Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers |
| WO2012078546A3 (en) * | 2010-12-06 | 2012-08-02 | Sytheon Ltd. | Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds |
| CN103402963A (en) * | 2010-12-06 | 2013-11-20 | 赛泽恩有限公司 | Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds |
| CN103415498A (en) * | 2010-12-06 | 2013-11-27 | 赛泽恩有限公司 | Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers |
| US8617528B2 (en) | 2010-12-06 | 2013-12-31 | Sytheon Ltd. | Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds |
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