GB991142A - Improvements relating to new substituted 2-(2-hydroxyphenyl)-benztriazole compounds and their use - Google Patents
Improvements relating to new substituted 2-(2-hydroxyphenyl)-benztriazole compounds and their useInfo
- Publication number
- GB991142A GB991142A GB2307862A GB2307862A GB991142A GB 991142 A GB991142 A GB 991142A GB 2307862 A GB2307862 A GB 2307862A GB 2307862 A GB2307862 A GB 2307862A GB 991142 A GB991142 A GB 991142A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- group
- unsubstituted
- alkoxy
- 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
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 16
- 125000003545 alkoxy group Chemical group 0.000 abstract 12
- 229910052799 carbon Inorganic materials 0.000 abstract 12
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 8
- 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
- 229910052736 halogen Inorganic materials 0.000 abstract 8
- 150000002367 halogens Chemical class 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 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
- 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
- 125000003302 alkenyloxy 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
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 4
- 125000004104 aryloxy group Chemical group 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
- -1 benztriazole compound Chemical class 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
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 4
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 4
- 150000003951 lactams Chemical class 0.000 abstract 4
- 125000001570 methylene group Chemical class [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
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 4
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-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
- 239000011248 coating agent Substances 0.000 abstract 2
- 238000000576 coating method Methods 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 238000006149 azo coupling reaction Methods 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 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
- 229920001577 copolymer Polymers 0.000 abstract 1
- 230000020335 dealkylation Effects 0.000 abstract 1
- 238000006900 dealkylation reaction Methods 0.000 abstract 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- 230000000266 injurious effect Effects 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 229920005615 natural polymer Polymers 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 150000002989 phenols Chemical class 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
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229920001059 synthetic polymer Polymers 0.000 abstract 1
- 150000003852 triazoles Chemical class 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
- C07D403/10—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 carbon chain containing aromatic rings
-
- 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
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention comprises substituted 2-(21-hydroxy - phenyl) - benztriazoles of the general formula <FORM:0991142/C2/1> wherein R1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical which are possibly substituted by carboxyl or carboxylic acid ester groups and 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 at the 4,5 or 6 positions by alkyl, alkoxy, carboxy, carboxylic acid ester or amide, sulphonic acid amide and alkylsulphonyl groups or halogen and at the 41 and 51 positions by alkyl, cycloalkyl, aralkyl and aryl groups, alkoxy groups or halogens. The "Acyl" group is a radical of the formula <FORM:0991142/C2/2> wherein X is a carbon atom or the radical <FORM:0991142/C2/3> and Y is oxygen, 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 if X is carbon, R2 is hydrogen or an alkenyloxy, cycloalkyloxy or substituted or unsubstituted alkoxy, aryloxy or aralkyloxy 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, R2 represents the remainder of a lactam or dioxopyrrolidine ring. These compounds may be prepared by heating a 2(21-hydroxyphenyl) benztriazole compound having an acylatable amino group in the 31 position with an acylating agent, said amino compound being prepared by reducing a 2 - nitro - 21 - hydroxy - 31 - acylamino - 1,11 - azobenzene compound (see Division C4) and saponifying the 2(21-hydroxy-31-acylaminophenyl) benztriazole compound so formed or by nitration of a 51-substituted 2(21-hydroxyphenyl) benztriazole and reduction of the 31 nitro compound so formed. Other methods for preparing the compounds of the invention are: (1) reduction of a 2-nitro-21-hydroxy - 31 - acylamino - 1,11 - azobenzene; (2) oxidation of a 2 - amino - 21 - hydroxy-31 - acylamino - 1,11 - azobenzene; (3) oxidation of a 2-amino-21-alkoxy, or acyloxy, -31-acylamino - 1,11 - azobenzene to form 2(21-alkoxy, or acyloxy, - 31 - acylaminophenyl) benztriazole and subsequent dealkylation, or saponification; and (4) modification of existing groups in compounds of Formula I. An intermediate of the formula <FORM:0991142/C2/4> may be isolated by the reduction of 2-nitro-21-hy droxy - 31 - acylamino - 1,11 - azobenzene with hydrosulphite and may be converted into the desired triazole by catalytic or zinc dust reduction. Several examples of the preparation and use of the compounds of the invention are given (see Divisions B2, B5, C3, C4 and G2). Reference has been directed by the Comptroller to Specification 878,362.ALSO:Synthetic and natural polymers are stabilized against light by the incorporation, usually as 0.001 to 5% by weight, therein of a compound of the general formula <FORM:0991142/C3/1> wherein R1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical which are possibly substituted by carboxyl or carboxylic acid ester groups and 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 at the 4, 5 or 6 positions by alkyl, alkoxy, carboxy, carboxylic acid ester or amide, sulphonic acid amide and alkylsulphonyl groups or halogen and at the 41 and 51 positions by alkyl, cyclo-alkyl, aralkyl and aryl groups, alkoxy groups or halogens. The "Acyl" group is a radical of the formula <FORM:0991142/C3/2> wherein X is a carbon atom or the radical <FORM:0991142/C3/3> and Y is oxygen, 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, cyclo-alkyl, aralkyl or substituted or unsubstituted alkyl or aryl group or, if X is carbon, R2 is hydrogen or an alkenyloxy, cyclo-alkyloxy or substituted or unsubstituted alkoxy, aryloxy or aralkyloxy 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, R2 represents the remainder of a lactam or dioxopyrrolidine ring. Specified polymers are the polymers and copolymers of ethylenically unsaturated monomers, polyacrylic compounds, polyesters, polyamides, polyester resins, cellulose, cellulose esters and ethers, and proteins. Reference has been directed by the Comptroller to Specification 878,362.ALSO:Lacquers used to protect light-sensitive materials from light contain at least one compound of the general formula <FORM:0991142/C4-C5/1> wherein R1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical which are possibly substituted by carboxyl or carboxylic acid ester groups and 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 at the 4, 5 or 6 positions by alkyl, alkoxy, carboxy, carboxylic acid ester or amide, sulphonic acid amide and alkylsulphonyl groups or halogen and at the 41 and 51 positions by alkyl, cyclo-alkyl, aralkyl and aryl groups, alkoxy groups or halogens. The "Acyl" group is a radical of the formula <FORM:0991142/C4-C5/2> wherein X is a carbon atom or the radical <PICT:0991142/C4-C5/1> and Y is oxygen, 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, cyclo-alkyl, aralkyl or substituted or unsubstituted alkyl or aryl group or, if X is carbon, R2 is hydrogen or an alkenyloxy, cycloalkyloxy or substituted or unsubstituted alkoxy, aryloxy or aralkyloxy 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, R2 represents the remainder of a lactam or dioxopyrrolidine ring. Intermediates in some of the methods of preparation of compounds of Formula I are azo-dyes, e.g. those produced by diazo-coupling of (a) o-nitro-anilines with phenols, (b) o-nitro-anilines with acylaminophenols, or (c) 2-acyloxy-3-acyl-amino-anilines with an aminobenzene compound with subsequent hydrolysis of the acyloxy group. A number of dyes are specified in the examples. Reference has been directed by the Comptroller to Specification 878,362.ALSO:Light-sensitive materials are protected against the injurious effects of light by coating them with compositions containing at least one compound of the general formula <FORM:0991142/B1-B2/1> wherein R1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical which are possibly substituted by carboxyl or carboxylic acid ester groups and 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 at the 4, 5 or 6 positions by alkyl, alkoxy, carboxy, carboxylic acid ester or amide, sulphonic acid amide and alkylsulphonyl groups or halogen and at the 41 and 51 positions by alkyl, cyclo-alkyl, aralkyl and aryl groups, alkoxy groups or halogens. The "Acyl" group is a radical of the formula <FORM:0991142/B1-B2/2> wherein X is a carbon atom or the radical <FORM:0991142/B1-B2/3> and Y is oxygen, 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, if X is carbon, R2 is hydrogen or an alkenyloxy, cycloalkyloxy or substituted or unsubstituted alkoxy, aryloxy or aralkyloxy 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, R2 represents the remainder of a lactam or dioxopyrrolidine ring. Specific mention is made of coating glass sheets. Reference has been directed by the Comptroller to Specification 878,362.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH709561A CH434279A (en) | 1961-06-16 | 1961-06-16 | Process for the preparation of substituted 2- (2'-hydroxyphenyl) -benztriazole compounds |
| CH709861 | 1961-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB991142A true GB991142A (en) | 1965-05-05 |
Family
ID=25700739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2307862A Expired GB991142A (en) | 1961-06-16 | 1962-06-15 | Improvements relating to new substituted 2-(2-hydroxyphenyl)-benztriazole compounds and their use |
Country Status (4)
| Country | Link |
|---|---|
| DK (1) | DK108884C (en) |
| ES (1) | ES278580A1 (en) |
| GB (1) | GB991142A (en) |
| SE (1) | SE310368B (en) |
Cited By (5)
| 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 |
| JP2018528165A (en) * | 2015-07-07 | 2018-09-27 | スリーエム イノベイティブ プロパティズ カンパニー | Substituted benzotriazole phenol |
-
1962
- 1962-06-15 SE SE672262A patent/SE310368B/xx unknown
- 1962-06-15 ES ES278580A patent/ES278580A1/en not_active Expired
- 1962-06-15 GB GB2307862A patent/GB991142A/en not_active Expired
- 1962-06-15 DK DK267362A patent/DK108884C/en active
Cited By (6)
| 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 |
| JP2018528165A (en) * | 2015-07-07 | 2018-09-27 | スリーエム イノベイティブ プロパティズ カンパニー | Substituted benzotriazole phenol |
| US10919867B2 (en) | 2015-07-07 | 2021-02-16 | 3M Innovative Properties Company | Substituted benzotriazole phenols |
Also Published As
| Publication number | Publication date |
|---|---|
| DK108884C (en) | 1968-02-19 |
| SE310368B (en) | 1969-04-28 |
| ES278580A1 (en) | 1963-02-01 |
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