DE1213408B - Use of substituted 2- (2-hydroxyphenyl) benzotriazole compounds to protect organic substances against ultraviolet radiation - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. Cl .:

Number:
File number:
Registration date:
Display day:

C07b

C08f
German KL: 12 ο-27

G35219IVb / 12o
June 15, 1962
March 31, 1966

The present invention relates to the use of substituted 2- (2'-hydroxyphenyl) benzotriazole compounds of the general formula I.

(D

in that of Xi and X ₂ one X represents the group - N - acyl

Ri

means where "acyl" is an organic acyl radical and Ri is hydrogen or an alkyl, alkenyl, Cycloalkyl or aralkyl radical, where Ri and "acyl" together with the amine nitrogen can form a ring and in this case Ri is a carbonyl or an optionally through alkyl group represents substituted methylene group, and the other X of Xi and X2 is hydrogen or im Case that it is Xi, one for the nucleus B named substituent or, in the case that it is X2, one named for the nucleus A. Is substituent and in formula I the nucleus A in positions 4, 5 and 6 by alkyl, alkoxy groups or halogen atoms and, when X2 is not an acylamino group is, also by carboxyl, carboxylic acid ester, carboxylic acid amide, sulfonic acid amide or Alkylsulfonyl groups and the core B in positions 3 ', 4' and 5 'by hydrocarbon groups, Alkoxy groups or halogen atoms can be substituted for protecting organic substances against ultraviolet radiation.

As mentioned, the benzene ring A can also contain alkyl groups such as methyl, ethyl, isobutyl groups, alkoxy groups such as methoxy and butoxy groups, halogens such as chlorine and bromine and, if X2 none, in positions 4, 5 and 6 Acylamido group is, also carboxyl groups, carboxylic acid ester groups, namely carboxylic acid alkyl ester groups, such as carbomethoxy, carboethoxy, carbopropoxy or carbobutoxy groups, optionally on the nitrogen aliphatic, cycloaliphatic or araliphatically substituted carboxamide or sulfonic acid amide groups, such as carboxamethylamide or sulfonic acid amide groups -, -cyclohexylamid-, -benzylamid-, -dimethylamid-, -diäthylamid-, -N-methyl-N-cyclohexylamid-, -y-methoxypropylamid-, -piperidid- or -morpholidgruppen Use of substituted 2- (2'-hydroxyphenyl ) benzotriazole compounds for protection
of organic substances against ultraviolet
radiation

Applicant:

J. R. Geigy A. G., Basel (Switzerland)

Representative:

Dr. F. Zumstein, Dr. E. Assmann

and Dr. R. Koenigsberger, patent attorneys,

Munich 2, Bräuhausstr. 4th

Named as inventor:

Dr. Hansjörg Heller, Riehen;

Dr. Jean Rody, Basel;

Dr. Ernst Keller, Binningen (Switzerland)

Claimed priority:

Switzerland of June 16, 1961 (7096)

as well as alkylsulfonyl groups, such as methylsulfonyl or ethylsulfonyl groups. The benzene ring B can in the positions 3 ', 4' and 5 'by hydrocarbon groups such as methyl, ethyl, Benzyl, α-phenylethyl, cyclohexyl or phenyl groups, Alkoxy groups, such as methoxy, ethoxy, propoxy, isopropoxy or n-butoxy groups or Halogens, such as chlorine or bromine, may be substituted. Same in group Xi or X2

Ri

- N -acyl

"acyl" is in particular a radical of the formula
Y

Il

- X ₃ -R ₂

where X3 is a carbon atom or the radical - S = O and Y is an oxygen atom or, when X3 denotes a carbon atom, also a sulfur atom, provided that R2 is a free or substituted amino group is, or an imino group which, together with X and R2, forms an s-triazine or pyrimidine ring forms, represents.

609 540/436

R2 represents an alkyl, alkenyl, cycloalkyl, aralkyl or an aryl group, it being possible for the aryl group to be substituted, for example, by halogen atoms, alkoxy, alkyl, free or modified carboxyl groups, and in particular when X _{3 is} a carbon atom, the Alkyl group can be further substituted, for example by halogen atoms, etherified mercapto, free or etherified hydroxyl groups, primary, secondary or tertiary amino groups and free or modified carboxyl groups, or if X3 is a carbon atom, R2 also denotes hydrogen or an alkoxy, alkenyloxy, cycloalkyloxy -, aralkyloxy or an aryloxy group, where the aryl radical of the aralkoxy or aryloxy group can be substituted for example by alkyl, alkoxy groups or halogen atoms and the alkyloxy group by alkoxy or alkyl mercapto groups, or an amino group which can be substituted on the nitrogen by one or two identical or different Alkyl, alkenyl, cycloalkyl, aralkyl or aryl groups can be substituted, or an imino group of a saturated monocyclic heterocycle, or, if Rl and R2 are linked, together with X3 and Ri the remainder of a lactam or dioxopyrrolidine ring.

In any case, the olefinic double bond of the optionally present alkenyl group is through at least 1 carbon atom from the nearest heteroatom and those bonded to saturated carbon atoms Heteroatoms are by at least one more carbon atom from the next heteroatom separated.

"Acyl" preferably represents the following groups, the preferred number in brackets Carbon atoms of this group is given.

a) An s-triazinyl radical of the formula

together contain a maximum of 19 carbon atoms), where R _{6 is} an alkyl (Ci - Ci ₈ ), an alkenyl (C ₃ - C ₅ ), a cycloalkyl (C ₅ - C ₈ ), an aralkyl (C7 - C12) , an aryl group (C ₆ - C10), which can be substituted in particular by halogen atoms, alkoxy, alkyl, free or modified carboxyl groups,

d) a carbamoyl radical of the formula

IO

Il>

C-N

R ₇

where R? denotes an alkylene radical (C4 - Cs) or an oxalkylene radical (C4 - C ₆ ) which, together with the nitrogen, forms a 5- to 7-membered saturated heterocycle,

e) a thiocarbamoyl radical of the formula

-C-NH-R ₆
f) a carbonic acid monoester radical of the formula

Il

-C-OR ₈

where Rs has the same meaning as R ₆ , but also an alkoxy-alkyl (C3 - C10), a haloalkyl (Ci - C ₅ ) or an alkylmercaptoalkyl (C ₃ - C10) radical,
g) a carboxylic acid residue of the formula

- C

N = C

N-C

ZR ₃

ZR ₃

wherein Z is an imino or an alkylimino group (Ci - C ₈ ), an oxygen or sulfur atom and R _{3 is} an alkyl (Ci-Ci ₂ ), cycloalkyl (C ₅ -C ₈ ) or an aralkyl (C7 - Ci ₂ ) means group, where R ₃ together with the alkylimino group can form a 5- to 7-membered, saturated heterocycle (and the whole group contains at most 25 carbon atoms),

b) a pyrimidyl radical that contains at most one CH group in the ring and that of the rest Carbon atoms is substituted by- 'chlorine and at most one ZRe group (and the whole Group contains not more than 17 carbon atoms),

c) a carbamoyl radical of the formula

O R4

Ii /

- C -N

-CR ₉

where R9 has the same meaning as R ₈ , but also hydrogen or an alkenyl (C ₆ -Ci ₈ ), a carboxyalkyl (C ₃ -C10), a carboxyaryl (C?), a carboxyalkenyl (Q - C ₆ ), a carbalkoxyalkyl (C ₃ - Cu), a carbocycloalkoxyalkyl (C ₆ - C9), a carboaralkyloxyalkyl (C ₈ - C14), a carboaryloxyalkyl (C ₈ - C14), a R ₆ - O - alkyl - (C2 - C22), one R ₆ - S - alkyl (C2 - C22), one

R ₄

Rs

N - alkyl -

R ₅

wherein R4 and R _{5 are} independently hydrogen or an R ₆ group (R4 and R ₅ (C2 - C22), an alkylene (C4 - C ₈ ) or an oxalkylene (C4 - C ₆ ) radical, or

h) a sulfonic acid radical of the formula —SO2R ', in which R' has the meaning given _{under R 6.}

If R ₃ to Rg are aryl radicals, they are preferably monocyclic. Ri preferably represents hydrogen, an unsubstituted alkyl (Ci - Ci ₈ ), a carboxyalkyl (C _{3 -C 5} ), a carbalkoxyalkyl (C ₃ -C 14), a cycloalkyl (C ₅ -C 5) or an aralkyl group (C7-C12). If Ri and R2 are linked to one another, Ri preferably represents a carbonyl or a methylene group and R2 a 1,2-ethylene group. Preferably, Ri and the “acyl” radical together contain at most

26 carbon atoms, a maximum of 5 nitrogen atoms, a maximum of 4 oxygen atoms and a maximum of! Sulfur atoms.

Benztriazole compounds which absorb particularly long wavelengths are obtained when acidifying substituents are in ring A and / or basic substituents are in the 3 'and / or 5' position. Benztriazole compounds with a particularly high molar extinction in the range from 330 to 350 μm are obtained when basic substituents are in the 4'- and / or 5-position. The molar absorption in the range of 300 πΐμ is promoted by optionally further substituted alkyl substituents in the 3'-position.

Examples of basic substituents are alkoxy groups, such as the methoxy, isopropoxy, Cyclohexyloxy and benzyloxy groups; Examples of acidifying substituents are alkylsulfonyl groups, such as the methyl and ethylsulfonyl group, sulfonic acid amide groups, such as the sulfonic acid methyl, -butyl and -cyclohexylamide groups, as well as the carboxyl group and its esters or amides.

Of course, typical dye groups in the benzotriazole compounds, such as. B. aromatic azo groups, auxochrome anthraquinone groups or phthalocyanine groups, as Exclude substituents.

Particularly suitable compounds that can be used according to the invention include, for example, the following, in which list the analytically pure substances are characterized by their melting point (uncorrected). Raw products which have been brought to a degree of purity sufficient for application but insufficient in terms of melting point by falling over and cleaning with animal charcoal are characterized by their spectral properties, with the wavelength of the longest-wave maximum (X) and the percentage transmission (T) of a solution of 1 mg of substance in 100 ml of chloroform with a layer thickness of 1 cm. The same applies to the physical indicators in the examples.

2- (2'-Hydroxy-4'-stearoylamidophenyl) -benztriazole (contains about 30% palmitoyl-

derivative); 136-137 ° C;
2- (2'-hydroxy-4'-oleylamidophenyl) benzotriazole;

a346nm; T 29%;
2- (2'-hydroxy-4'-cyclohexanecarboxylic acid

amidophenyl) benzotriazole; F 268 ^° C;
2- (2'-Hydroxy-4'-y-chlorobutyrylamidophenyl) -

benztriazole; λ 345 nm; T 14%;
2- (2 ^/ -hydroxy-4 '- / J-methoxypropionylamido-

phenyl) benzotriazole; A346nm; T 13%;

2- (2'-hydroxy-4 '- / i-n-butylmercaptopropionyl-

amidophenyl) benzotriazole (double melting point: first 135 ° C; then 146 ° C);
2- (2'-hydroxy-4 '- /? - morpholylpropionylamido-

phenyl) benzotriazole; A347nm; T 18%;

2- (2'-Hydroxy-4'-carbomethoxyamidophenyl) -

benztriazole; 224 ° C;
2- (2'-Hydroxy-4'-carbooctyloxyamidophenyl) -

benztriazole; F 133 ⁰ C;
2- (2'-Hydroxy-4'-carbobenzyloxyamidophenyl) -

benztriazole; 183 ° C;
2- (2'-hydroxy-4'-carbocyclohexyloxyamido-

phenyl) benzotriazole; F 175 ° C;

2- (2'-Hydroxy-4'-carbomethoxyamidophenyl) -

5-chlorobenzotriazole; F 202 ^° C;
2- (2'-Hydroxy-4'-methanesulfonic acid amido-

phenyl) benzotriazole; F 201 ⁰ C;
2- (2'-Hydroxy-4'-p-toluenesulfonic acid-ethyl-

amidophenyl) benzotriazole; 127 ° C;
2- (2'-Hydroxy-4'-pentanecarboxamido-

phenyl) -5-chlorobenzotriazole; F 180 ⁰ C;
2- (2'-Hydroxy-4'-pentanecarboxamido-

phenyl) benzotriazole-5-carboxylic acid; F larger

than 280 ⁰ C;
2- (2'-Hydroxy-4'-phenylcaramoyl-ethylamido-

phenyl) benzotriazole; F 147 ° C;
2- [2'-hydroxy-4 '(4 ", 6" -bis-dibutylamino-

l ", 3", 5 "-triazinyl- (2")) - aminophenyl] -

benztriazole; F 142 ° C ;.
2- [2'-hydroxy-4 '- (4 ", 6" -dibutylmercapto-

l ", 3", 5 "-triazinyl- (2")) - aminophenyl] -

5-chlorobenzotriazole; F 157 ^° C;
2,4-bis- (4'-benzotriazolyl- (2) -3'-hydroxyphenyl-

amino) -6-dibutylamino-1,3,5-triazine; F 280 ° C; 2- (2'-Hydroxy-4'-ß-carboxypropionic acid amido-

phenyl) benzotriazole; F 238 ° C;
2- (2'-hydroxyphenyl) -5-pentanecarboxylic acid

amido-6-methyl-benzotriazole; F 204 ⁰ C;
2- (2'-Hydroxyphenyi) -6-chloro-5-stearoylamido-

benztriazole; F 148 ⁰ C;
2- (2'-hydroxyphenyl) -4-methyl-5 - (/? - butyl-

mercaptopropionylamido) benzotriazole;

192 ° C;
2- (2'-hydroxyphenyl) -5- (dibutylamino-acetyl-

amido) benzotriazole; F 12O ⁰ C;
2- (2'-Hydroxy-5'-chlorophenyl) -5-nonane-carbon-

acid amido-4-methyl-benzotriazole; F 175 ⁰ C;
2- (2'-hydroxy-5'-cyclohexylphenyl) -5-acetyl-

amido-benzotriazole; 211 ° C;
2- (2'-hydroxyphenyl) -5-benzoyl-N-benzyl-

amino-benzotriazole; F 153 ^° C;
2- (2'-hydroxyphenyl) -5-acetylethylamido-

6-methyl-benzotriazole; 136 ° C;
2- (2'-Hydroxy-3'-benzyl-5'-methylphenyl) -

5-acetylamido-benzotriazole; 232 ° C;
2- (2'-Hydroxy-4'-ethoxyoxalic acid amidophenyl) benzotriazole; F234 ° C.

The substituted 2 - (2 '- hydroxyphenyl) benzotriazole compounds used according to the invention can be prepared by methods known per se, for example by reaction a corresponding 2- (2'-hydroxyphenyl) benzotriazole compound containing an acylatable amino group in the 4'- or in the 5-position with an acylating agent. For the preparation of the compounds to be used according to the invention, here no protection claimed.

The substituted 2- (2'-hydroxyphenyl) benzotriazole compounds of the formula I are, depending on the substitution, Colorless to slightly yellow in color and absorb UV light. Opposite connections similar constitution as z. B. are described in German Auslegeschrift 1 185 610, show they have an improved absorption of UV light, in particular an increased molar extinction. Particularly they are therefore suitable in all cases where the lowest possible UV transparency is desired will. Furthermore, they are characterized by a low volatility, i. H. an improved Sublimation fastness.

In terms of lightfastness, the 5-acylamido compounds are very cheap. In general, the lightfastness decreases with both the 5-acylamido and also with the 4'-acylamido compounds in the following order: Triazinylamino -> Carboxamides - »■ sulfonic acid amido compounds; d. h., ever The more acidic the free acid corresponding to the acyl radical, the better the lightfastness.

The UV absorbers are added to the photosensitive substrates in small amounts of 0.001 to 5%, in particular in amounts of 0.01 to 1%, incorporated into the carrier material.

As carrier materials for the compounds of the formula I, polymers are primarily suitable, especially fully synthetic polymers, e.g. B. addition polymers, especially polymers of compounds with ethylenic double bonds, such as B. polyvinyl chloride, polyvinylidene chloride, polymers of Styrene, polymers of dienes and their copolymers, polyethylene, polypropylene, polyacrylic compounds, in particular polymethyl methacrylate or polyacrylonitrile, and also condensation polymers such as Polyester, e.g. B. polyethylene glycol terephthalate, or polyamides, such as polycaprolactam, or also mixed polymers, such as, for example, polyester resins; furthermore natural polymers, or their synthetic ones Modifications such as B. cellulose, cellulose esters and ethers and proteins. The molecular weight the above polymers plays a minor role as long as it is within the range for the characteristic mechanical properties of the polymers concerned lies. Depending on the polymer, it can be between 1,000 and several million. In non-polar Polymers, those benzotriazole compounds are particularly suitable which, in addition to the definition existing hydroxyl group as few polar groups with mobile hydrogen atoms as possible, such as z. B. secondary carboxylic acid or sulfonic acid amide groups, especially no secondary sulfonic acid amide groups contain. In this case, low-melting products are generally preferred because of their solubility.

In general, it is advisable to examine the possibility of using a specific product To estimate solubility tests. For example, the product is also hot in the solvents that for the polymers to be protected are known to be sparingly soluble, so there is an unfavorable compatibility in expected from this polymer. Incorporation of the acylamido-2- (2'-hydroxyphenyl) benzotriazole compounds in these polymers happens - depending on the type of polymer - by incorporating at least one of these compounds and optionally other additives, such as. B. plasticizers, antioxidants, Heat stabilizers and pigments, in the melt or plasticized form according to the in the usual methods of technology before or during the shaping, or by dissolving in the appropriate Monomers before polymerization or by dissolving the polymer and additives in solvents and subsequent evaporation of the latter. The substituted 2- (2'-hydroxyphenyl) benzotriazole compounds can also be made from bathrooms, e.g. B. from aqueous dispersions, drawn onto films or threads.

The light-sensitive materials can also be protected from the harmful effects of light by covering them with a protective layer containing at least one compound of the formula I according to the definition, e.g. B. a varnish, or that they are covered with such light stabilizers containing - appropriately film-like - structures. In these two cases, the amount of light stabilizers added is advantageously 10 to 30% (based on the protective layer material) for protective layers less than 0.01 mm thick and 1 to 10% for protective layers from O ₃ O1 to 0.1 mm thick. In general, the more colorless the benzotriazole compounds are, the more valuable they are, since otherwise they easily cause the end product to turn yellow. In certain types of use, especially when warm pulp are powdered, benzotriazole compounds which melt above the softening temperature of the polymers in question and are nevertheless sufficiently soluble in the molten polymer are particularly valuable.

The following examples illustrate the invention. Therein mean, unless otherwise noted is, the parts are parts by weight. The temperatures are given in degrees Celsius. Parts by weight are in the same proportion to parts by volume as kilograms to liters.

example 1

Films made of cellulose acetate are produced by adding a solution consisting of 150 parts of cellulose-2,5-acetate (from Lonza, Weil, Germany), 20 parts of dibutyl phthalate, 825 parts of acetone and 0.5 part of 2- (2'-hydroxy-5'-cyclohexylphenyl) -5-acetylamido-benzotriazole (F 211 °) was drawn onto glass. After evaporation of the solvent, transparent films 0.05 mm thick were formed obtain.

Sections of these films were exposed in the fadeometer for 1000 hours. The so exposed Films did not show any signs of embrittlement, as did films of an analogous composition, but without Content of light stabilizers according to the invention, occur after this exposure. Similar results are preserved with the connections

2- (2'-Hydroxy-4'-carbooctyloxyamidophenyl) -

5-chlorobenzotriazole; F 139 °;
2- (2'-Hydroxy-4'-pentanecarboxamido-

phenyl) -5-ethylsulfonyl-benzotriazole; A363 nm; T 24%;

2- (2'-hydroxy-4 ^/ methanesulfonylethylamidophenyl) benzotriazole; F 184 °.

Example 2

A mixture consisting of 65 parts of commercially available polyvinyl chloride (from Lonza AG, Basel, Switzerland), 32 parts of dioctyl phthalate, 2 parts of barium cadmium laurate and 0.2 parts of the compound 2 - (2 '- Hydroxy - 4' - nonanecarboxamidophenyl) -benztriazole (F 152 °) was on the two-roll mill calendered at 150 ° to a homogeneous skin. The 0.1 mm thick film obtained in this way is absorbed the UV light and is suitable as a protective film for UV-sensitive material. So z. B. Tubes for washing emulsions that have to be protected from UV light. Similar results are obtained if, instead of the compound mentioned, 2 - (2 '- hydroxyphenyl) - 5 - benzoylbenzylamido-benzotriazole, F 153 °; 2- (2'-hydroxy-5'-methyl-

phenyO-S-acetylamido-benzotriazole, mp 212 °; 2- (2'-Hydroxy-S'-methyl-S'-tert-butylphenyO-S-acetylamidobenzotriazole, mp 265 °; 2- (2'-hydroxy-3 ', 5'-di-tert-butylphenyl) -5 -acetylamidobenzotriazole, λ 357 nm; T 34% or 2- (2'-hydroxy-5'-tert.octylphenyl) -5-acetylamido-benzotriazole, melting point 208 °, is used.

Example 3

100 parts of polyethylene (DFD from Union Carbide International Cie, New York, 17, 270 Park Avenue, NY, USA.) Were mixed with 0.3 parts of the compound 2 - (2 '- hydroxy - 4' - acetyl - ethylamidophenyl) - benztriazole, F 148 °, mixed dry and the mixture processed into a blown film 0.1 mm thick by means of an extruder. The film obtained absorbs ultraviolet light and can therefore be used as a packaging material for UV-sensitive material. The transmittance for UV light measured at 365 ΐημ (Hg line) was less than 2% of the transmittance of a film of the same type without UV absorber. Similar results are obtained when using the compound 2 - (2 '- hydroxyphenyl) -5 - benzoyloctylamido-benzotriazole, λ 346 nm, T 34%.

Example 4

25th

Unsaturated polyester resin was prepared by heating 600 parts of propylene glycol, 460 parts of maleic anhydride and 350 parts of phthalic anhydride under a nitrogen atmosphere at 195 ° until the reaction mass had an acid value of 40. After cooling, the crushed mass was dissolved in half the amount by weight of styrene. 0.2 part of 2- (2'-hydroxyphenyl) -5-ρ-toluenesulfonic acid ethylamido-6-methylbenzotriazole and 0.5 part of benzoyl peroxide were added to 100 parts of this resin mixture. The liquid resin mixture was poured into molds and cured for 3 hours at 80 °. The moldings obtained, in the case according to the invention, plane-parallel plates of 4 mm thickness, absorb UV light of wavelengths below 370 ηΐμ. They are more stable to yellowing due to the influence of light than the same plates which have been produced without the addition of the compounds according to the invention. Similar results are obtained if, instead of the compound mentioned, 2- (2'-hydroxy-5'-chlorophenyl) -5-pentanecarboxamido-4-methylbenzotriazole, melting point 204 °; 2- (2'-Hydroxy-3 ', 5'-dimethylphenyl) -5-acetylamidobenzotriazole, mp 276 °; 2- (2'-Hydroxy-4 ', 5' - dimethylphenyl) - 5 - acetylamidobenzotriazole, λ 355 nm, T 17%; 2- (2'-Hydroxy-3 ', 5'-dichlorophenyl) -5-acetylamidobenzotriazole, λ 352 nm, T 25%; 2- (2'-Hydroxy-4 ', 5'-dichlorophenyl) -5-acetylamidobenzotriazole, λ 353 nm, T 17%, or 2- (2'-hydroxy-5'-phenyl-phenyl) -5-acetylamidobenzotriazole, Double melting point: first 209 °, then 246 °, is used.

Example 5

0.2 part of 2- (2'-hydroxyphenyl) -5-benzoylamido-6-chlorobenzotriazole (F 156 °), 100 parts of methyl methacrylate and 0.2 part of lauroyl peroxide as polymerization initiator were mixed and polymerized at 70 ° in a glass mold to form a plate 4 mm thick. -The transmission of the completely colorless Plate is between 380 and 290 ηΐμ less than 0.5%, i.e. In other words, the plate is practically completely impermeable to UV. After an exposure time of Unchanged transmission values were obtained for 100 hours in the Xenotest device. This material is suitable therefore excellent for the production of lightfast, absorbing sharply at the limit of the visible, but completely colorless UV filters. Similar results are obtained when 2- (2'-hydroxy - 4 '- acetylethylamidophenyl) - benzotriazole is used.

Example 6

100 parts of granulated polyamide (nylon 6, made by polymerizing ε-caprolactam) were mixed dry with 1 part of 2- (2'-hydroxyphenyl) -5-acetylamido-benzotriazole (F 214 °) and the mixture by means of an extruder, which was equipped with a hollow nozzle, to a continuous one Blow blown film 0.05 mm thick. The transparent, practically colorless film thus obtained absorbs the ultraviolet light and can be used as a UV-absorbing packaging material Find. Similar results are obtained when in place of the triazole compound used 2 - (2 '- hydroxy - 4' - acetylamidophenyl) - benzotriazole is used.

Example 7

100 parts of polystyrene (bead polymer) and 0.2 part of the compound 2- (2'-hydroxy-4'-benzoylethylamidophenylbenzotriazole (F 139 °) were mixed and injected into sheets with a wall thickness of 1.5 mm. These plates showed after a period of exposure no discoloration of 3 months in sunlight, while the same plates, but without the addition of UV absorbers according to the invention, exhibited a distinct yellow tinge.

Used instead of the aforementioned benzotriazole compound, 2- (2'-hydroxyphenyl) -5-benzoylbenzylamidobenzotriazole is used, similar results are obtained.

Example 8

50 parts of polyvinyl chloride (quality CH 5 from Lonza AG., Basel, Switzerland), 32 parts of dioctyl phthalate, 1 part 2- (2'-hydroxyphenyl) -6-chloro-5-heptanecarboxamide-benzotriazole (F 148 °) and 1 part dibutyltin dilaurate were processed at 100 ° in a mixing kneader until a homogeneous mass was formed. To lower the viscosity, 10 parts of Sangajol were then added, after renewed homogenization The paste was applied in a 0.2 mm thick spread on a sheet of sisal fabric applied and gelled at 180 ° for 3 minutes.

The coated fabric was exposed to daylight for two months without any noticeable Changes in the color of the fabric could be determined. Same with polyvinyl chloride Fabric coated without a UV absorber showed after an exposure time of one Month a strong browning. A similar result is obtained if instead of the one used above Benztriazole compound 2 - (2'-hydroxy-4'-o-chlorobenzoylethyl-amidophenyl) -benztriazole is used.

Example 9

A protective varnish against the influence of light was produced as follows:

60 parts of Plastopal BT (urea resin from BASF in Ludwigshafen), 10 parts of a solution of

609 540/436

10% hydrochloric acid in ethanol. 10 parts of butanol, 19 parts of ethanol and 1 part of 2- (2'-hydroxyphenyl) -5- (dibutylaminoacetylamido) -benztriazole (F 120 °) were mixed to form a homogeneous solution and bleached maple veneer was coated with it. After the varnish had dried, the veneer was exposed to sunlight at the same time as an unpainted sample. After 2 weeks of exposure, the lacquered sample was still practically unchanged, while the veneer without light protection lacquer was heavily browned. _ϊ0

Claims (1)

Claim: Use of substituted 2- (2'-hydroxyphenyl) benzotriazole compounds of the general formula ' _O H B 4> -Xi (I) .6 '5' / 20th in that of Xi and Xz an X is the group
- N -acyl means where "acyl" is an organic acyl radical and Ri denotes hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical, where Ri and "acyl" can form a ring together with the amine nitrogen and in this case Ri represents a carbonyl or a methylene group optionally substituted by alkyl groups, and the other X of Xi and X _{2 is} hydrogen or, in the case that it is Xi, a substituent mentioned for the nucleus B or, in the case that it is X2, a substituent mentioned for the nucleus A, and in formula the nucleus A in positions 4, 5 and 6 by alkyl, alkoxy groups or halogen atoms and, if X2 is not an acylamido group, also by carboxyl, carboxylic ester, carboxamides, sulfonic acid amide or alkylsulfonyl groups and the nucleus B in positions 3 ', 4' and 5 'may be substituted by hydrocarbon groups, alkoxy groups or halogen atoms for protecting organic substances from ultraviolet radiation. Considered publications:
German interpretative document No. 1 185 610. 609 540/436 3.66 © Bundesdruckerei Berlin