GB991320A - Improvements relating to the stabilisation of light and oxidation sensitive organic materials - Google Patents
Improvements relating to the stabilisation of light and oxidation sensitive organic materialsInfo
- Publication number
- GB991320A GB991320A GB2308162A GB2308162A GB991320A GB 991320 A GB991320 A GB 991320A GB 2308162 A GB2308162 A GB 2308162A GB 2308162 A GB2308162 A GB 2308162A GB 991320 A GB991320 A GB 991320A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- group
- substituted
- cycloalkyl
- aralkyl
- 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
- 239000011368 organic material Substances 0.000 title abstract 2
- 230000003647 oxidation Effects 0.000 title abstract 2
- 238000007254 oxidation reaction Methods 0.000 title abstract 2
- 230000006641 stabilisation Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 17
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 12
- 125000002252 acyl group Chemical group 0.000 abstract 8
- 125000003342 alkenyl group Chemical group 0.000 abstract 8
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 8
- 125000003118 aryl group Chemical group 0.000 abstract 8
- 229910052799 carbon Inorganic materials 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 8
- 229910052736 halogen Inorganic materials 0.000 abstract 8
- 150000002367 halogens Chemical class 0.000 abstract 8
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 8
- 125000003277 amino group Chemical group 0.000 abstract 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 abstract 4
- 150000001721 carbon Chemical group 0.000 abstract 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 150000003951 lactams Chemical class 0.000 abstract 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 4
- QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical group O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 abstract 4
- -1 benztriazole compound Chemical class 0.000 abstract 3
- 239000007800 oxidant agent Substances 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 230000004048 modification Effects 0.000 abstract 2
- 238000012986 modification Methods 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 abstract 1
- KRTRYNYVYZTVDN-UHFFFAOYSA-N 3-(N-benzoyl-4-hydroxyanilino)propanoic acid Chemical compound C(=O)(O)CCN(C(C1=CC=CC=C1)=O)C1=CC=C(C=C1)O KRTRYNYVYZTVDN-UHFFFAOYSA-N 0.000 abstract 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000006701 autoxidation reaction Methods 0.000 abstract 1
- 238000006149 azo coupling reaction Methods 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 230000020335 dealkylation Effects 0.000 abstract 1
- 238000006900 dealkylation reaction Methods 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229920005615 natural polymer Polymers 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000003209 petroleum derivative Substances 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920001225 polyester resin Polymers 0.000 abstract 1
- 239000004645 polyester resin Substances 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 230000002829 reductive effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229920001059 synthetic polymer Polymers 0.000 abstract 1
- 239000001993 wax Substances 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- 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
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
2 - (21Hydroxy - 51 - acylaminophenyl)-benztriazole compounds of the general formula <FORM:0991320/C2/1> wherein R1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical which may be substituted by a carboxy or carbalkoxy group or R1 and "Acyl," together with the amino nitrogen atom can form a ring when R1 is a carbonyl or unsubstituted or alkyl substituted methylene group, and wherein the nucleus may be substituted in the 4, 5 or 6 positions by alkyl, alkoxy, carboxy, carboxylic acid ester or amide, sulphonic acid amide or alkyl-sulphonyl groups or halogen and at the 31 and 41 positions by alkyl, cycloalkyl, aralkyl or aryl groups or halogen, are incorporated into light and oxidation sensitive organic materials to stabilize said materials. The "Acyl" group is a radical of the formula <FORM:0991320/C2/2> wherein X is a carbon atom or the radical <FORM:0991320/C2/3> and Y is oxygen or an imino group which with X and R2 forms a s-triazine or pyrimidine ring or, when X is carbon, a sulphur atom and R2 is an alkenyl, cycloalkyl, aralkyl or substituted or unsubstituted alkyl or aryl group, or a substituted or unsubstituted amino group, an imino group of a saturated monocyclic heterocycle or, if R1 and R2 are linked together, together with X and R1, it represents the remainder of a lactam or dioxopyrrolidine ring. These compounds may be prepared by heating, in a weakly acid to weakly basic medium and possibly in an inert organic solvent, a 2-(21-hydroxyphenyl) benztriazole compound having an acylatable amino group in the 31 position with an acylating agent. Other methods of preparation are (1) oxidative ring closure of 2 - amino - 21 - hydroxy - 51 - acylamino -1 ,11-azobenzene with a salt of divalent copper in a neutral to alkaline medium; (2) reductive ring closure of 2-nitro-21-hydroxy-51-acylamino-1,11-azo-benzene e.g. by zinc in alkaline medium; (3) dealkylation of 2-(21-alkoxy-51-acylaminophenyl) benztriazole; (4) saponification of 2-(21-acyloxy-51-acylaminophenyl) benztriazole; and (5) modification of groups in an existing compound of Formula I. Several examples of the preparation and use of compounds of the invention are given.ALSO:Synthetic polymers, natural polymers or synthetic modifications thereof are stabilized against light and oxidizing agents by incorporating therein a compound of the general formula <FORM:0991320/C3/1> wherein R1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical which can be substituted by a carboxy or carbalkoxy group or R1 and "Acyl" together with the amino nitrogen atom can form a ring when R1 is a carbonyl or unsubstituted or alkyl-substituted methylene group, and wherein the nucleus may be substituted in the 4, 5 or 6 positions by alkyl, alkoxy, carboxy, carboxylic acid ester or amide, sulphonic acid amine or alkyl-sulphonyl groups or halogen and at the 31 and 41 position by alkyl, cycloalkyl, aralkyl and aryl groups or halogen. The "Acyl" group is a radical of the formula <FORM:0991320/C3/2> wherein X is a carbon atom or the radical <FORM:0991320/C3/3> and Y is oxygen or an imino group which with X and R2 forms an s-triazine or pyrimidine ring or, when X is carbon, a sulphur atom, and R2 is an alkenyl, cycloalkyl, aralkyl or substituted or unsubstituted alkyl or aryl group, or a substituted or unsubstituted amino group, or an imino group of a saturated monocyclic heterocycle or, if R1 and R2 are linked together, together with X and R1, it represents the remainder of a lactam or dioxopyrrolidine ring. Specified polymers are the addition polymers of vinyl chloride, vinylidene chloride, styrene, butadiene, isoprene, ethylene, propylene, acrylonitrile and methylacrylate and copolymers thereof; polyesters; polyamides; polyester resins; cellulose; cellulose esters and ethers; and proteins.ALSO:Fats, waxes and oil are stabilized against light and oxidizing agents by incorporating therein a compound of the general formula <FORM:0991320/C4-C5/1> wherein R1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical which can be substituted by a carboxy or carbalkoxy group or R1 and "Acyl" together with the amino nitrogen atom can form a ring when R1 is a carbonyl or unsubstiuted or alkyl-substituted methylene group, and wherein the nucleus may be substituted in the 4, 5 or 6 positions by alkyl, alkoxy, carboxy, carboxylic acid ester or amide, sulphonic acid amide or alkyl-sulphonyl groups or halogen and at the 31 and 41 position by alkyl, cycloalkyl, aralkyl and aryl groups or halogen. The "Acyl" group is a radical of the formula <FORM:0991320/C4-C5/2> wherein X is a carbon atom or the radical <FORM:0991320/C4-C5/3> and Y is oxygen or an imino group which with X and R2 forms an s-triazine or pyrimidine ring or, when X is carbon, a sulphur atom, and R2 is an alkenyl, cycloalkyl, aralkyl or substituted or unsubstituted alkyl or aryl group, or a substituted or unsubstituted amino group, or an imino group of a saturated monocyclic heterocycle or, if R1 and R2 are linked together, together with X and R1, it represents the remainder of a lactam or dioxopyrrolidine ring. Also mentioned are lacquers for coating light-sensitive materials comprising a compound of the general formula I. In an example the autoxidation of a petroleum distillate oil is retarded by the addition of various compounds of Formula I. In another example intermediate 2-nitro -21-hydroxy-51-acylaminoazobenzenes are prepared by diazo-coupling of o-nitroaniline with N - acetyl - p - aminophenol or p - N - b -carboxypropionyl - N - butylaminophenol or p - (N - carboxyethyl - N - benzoyl - amino)-phenol.ALSO:Surfaces are coated with polymers that have been stabilized against light and oxidizing agents by incorporating therein a compound of the general formula <FORM:0991320/B1-B2/1> wherein R1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical which can be substituted by a carboxy or carbalkoxy group or R1 and "Acyl" together with the amino nitrogen atom can form a ring when R1 is a carbonyl or unsubstituted or alkyl-substituted methylene group, and wherein the nucleus may be substituted in the 4, 5 or 6 positions by alkyl, alkoxy, carboxy, carboxylic acid ester or amide, sulphonic acid amide or alkylsulphonyl groups or halogen and at the 31 and 41 position by alkyl, cycloalkyl, aralkyl and aryl groups or halogen. The "Acyl" group is a radical of the formula <FORM:0991320/B1-B2/2> wherein X is a carbon atom or the radical <FORM:0991320/B1-B2/3> and Y is oxygen or an imino group which with X and R2 forms an s-triazine or pyrimidine ring or, when X is carbon, a sulphur atom, and R2 is an alkenyl, cycloalkyl, aralkyl or substituted or unsubstituted alkyl or aryl group, or a substituted or unsubstituted amino group, or an imino group of a saturated monocyclic heterocycle or, if R1 and R2 are linked together, together with X and R1, it represents the remainder of a lactam or dioxopyrrolidine ring. In the examples glass is coated with stabilized polyacrylonitrile, and cellulose-acetobutyrate, -acetate and propionate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH709861 | 1961-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB991320A true GB991320A (en) | 1965-05-05 |
Family
ID=4319897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2308162A Expired GB991320A (en) | 1961-06-16 | 1962-06-15 | Improvements relating to the stabilisation of light and oxidation sensitive organic materials |
Country Status (8)
| Country | Link |
|---|---|
| AT (2) | AT246709B (en) |
| BE (1) | BE633871A (en) |
| DE (1) | DE1213410B (en) |
| DK (1) | DK108817C (en) |
| ES (1) | ES278579A1 (en) |
| GB (1) | GB991320A (en) |
| NL (2) | NL279769A (en) |
| SE (1) | SE303378B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500332A (en) * | 1995-04-26 | 1996-03-19 | Eastman Kodak Company | Benzotriazole based UV absorbers and photographic elements containing them |
| US5670654A (en) * | 1995-06-29 | 1997-09-23 | Eastman Kodak Company | Method of synthesizing 2-(2'-hydroxyphenyl) benzotriazole compounds |
| US5683861A (en) * | 1996-10-23 | 1997-11-04 | Eastman Kodak Company | Benzotriazole-based UV absorbers and photographic elements containing them |
| US5739348A (en) * | 1996-10-23 | 1998-04-14 | Eastman Kodak Company | Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process |
Family Cites Families (1)
| 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 |
-
0
- NL NL126799D patent/NL126799C/xx active
- NL NL279769D patent/NL279769A/xx unknown
- BE BE633871D patent/BE633871A/xx unknown
-
1962
- 1962-06-15 AT AT111064A patent/AT246709B/en active
- 1962-06-15 ES ES278579A patent/ES278579A1/en not_active Expired
- 1962-06-15 AT AT484362A patent/AT247007B/en active
- 1962-06-15 DK DK267762A patent/DK108817C/en active
- 1962-06-15 DE DEG35221A patent/DE1213410B/en active Pending
- 1962-06-15 SE SE672562A patent/SE303378B/xx unknown
- 1962-06-15 GB GB2308162A patent/GB991320A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500332A (en) * | 1995-04-26 | 1996-03-19 | Eastman Kodak Company | Benzotriazole based UV absorbers and photographic elements containing them |
| US5670654A (en) * | 1995-06-29 | 1997-09-23 | Eastman Kodak Company | Method of synthesizing 2-(2'-hydroxyphenyl) benzotriazole compounds |
| US5683861A (en) * | 1996-10-23 | 1997-11-04 | Eastman Kodak Company | Benzotriazole-based UV absorbers and photographic elements containing them |
| US5739348A (en) * | 1996-10-23 | 1998-04-14 | Eastman Kodak Company | Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process |
Also Published As
| Publication number | Publication date |
|---|---|
| NL126799C (en) | |
| NL279769A (en) | |
| DE1213410B (en) | 1966-03-31 |
| BE633871A (en) | |
| ES278579A1 (en) | 1963-02-01 |
| DK108817C (en) | 1968-02-12 |
| AT246709B (en) | 1966-05-10 |
| SE303378B (en) | 1968-08-26 |
| AT247007B (en) | 1966-05-25 |
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