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HK1002331B - Stabilised polymers containing heteroatoms in the main chain - Google Patents

Stabilised polymers containing heteroatoms in the main chain Download PDF

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Publication number
HK1002331B
HK1002331B HK98101303.3A HK98101303A HK1002331B HK 1002331 B HK1002331 B HK 1002331B HK 98101303 A HK98101303 A HK 98101303A HK 1002331 B HK1002331 B HK 1002331B
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HK
Hong Kong
Prior art keywords
methyl
dioxy
ethyl
sugarcane
polymer composition
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HK98101303.3A
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German (de)
French (fr)
Chinese (zh)
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HK1002331A1 (en
Inventor
Schmitter Andre
Burdeska Kurt
Slongo Mario
Birbaum Jean-Luc
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西巴特殊化学品控股有限公司
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Publication of HK1002331B publication Critical patent/HK1002331B/en
Publication of HK1002331A1 publication Critical patent/HK1002331A1/en

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Description

The invention relates to stabilised polymers with heteroatoms in the main chain containing a 2-hydroxyphenyl-s-triazine with certain substituents as a stabiliser.
Polymers are known to be resistant to damage by light, oxygen and heat by the addition of a 2-hydroxyphenyls-triazine of the formula These compounds are UV absorbers and have also been proposed for the stabilization of photomaterials (US-A-3 843 371) or coatings (US-A-4 619 956).
In particular, triazine derivatives in which Ar is a 2,4-dimethylphenyl residue have been used because these compounds are relatively easily accessible.
Surprisingly, it has now been found that such triazines in which Ar is a phenyl or p-toly residuum exhibit a particularly good stabilizing effect in thermoplastic polymers containing heteroatoms in the main chain, clearly exceeding that of triazines in which Ar is a 2,4-dimethylphenyl residuum.
The invention therefore concerns a polymer composition which is stable against damage by light, oxygen and heat, and which contains: (b) at least one hydroxyphenyltriazine compound of formula I as the stabilizer; where R is hydrogen, C1-C18-alkyl, C2-C6-alkyl or benzyl substituted with halogen or C1-C12-alkoxy and R' is hydrogen or methyl, excluding compounds obtained by treatment of fibre material of component (a) with the stabilizer of component (b).
Polymers containing heteroatoms in the main chain are mainly polymers containing O, S and N. Examples of such polymers are the following classes of thermoplastic polymers: Polyacetals, such as polyoxymethylenes, and polyoxymethylene containing comonomers, such as ethylene oxide; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.2. polyphenylenes and their mixtures with styrene polymers or polyamides.3. polyamides and copolyamides, such as those derived from diamines and dicarboxylic acids and/or from aminocarbons or their corresponding lactates, such as polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/10, 6/19, 6/12, 4/6, polyamide 11, polyamide 12, aromatic polydips of m-X, diamine, and polyamide A;Err1:Expecting ',' delimiter: line 1 column 628 (char 627)Polycarbonates and polyester carbonates, in particular aromatic polycarbonates, such as those based on 2,2-bis ((4-hydroxyphenyl) propane or 1,1-bis ((4-hydroxyphenyl) cyclohexane.7. Polysulfones, polyethersulfones and polyether ketones, in particular aromatic polymers of this class.8. Mixtures (polyblend) of such polymers with each other or with other polymers, e.g. with polyolefins, polyacrylates, polydienes or other elastomers as shock-absorbing modifiers.
The preferred products are polycarbonates, polyester, polyamide, polyacetals, polyphenylenoxides and polyphenylene sulphides, but in particular polycarbonates. where A is a divalent phenolic residue. Examples of A are given in, inter alia, US-A-4 960 863 and DE-A-3 922 496. For example, A may be derived from hydroquinone, resorcin, dihydroxybiphenyls or bisphenols in the broadest sense such as bis- ((hydroxyphenyl) alkanes, cycloalkanes, sulphides, ethers, ketones, sulphones, sulfoxides, α, α'-bis- ((hydroxyphenyl) diisopropylbenzoles, e.g. from the compounds 2,2-bis-bis-hydroxyphenyl) -propanone, 2,2-bis- ((3-dimethyl-4-hydroxyphenyl) -propanone, 2,2-bis-bis-hydroxyphenyl), 2,2-bis-bis-hydroxyphenyl, 2,3-bis-hydroxyphenyl, 2,4-bis-hydroxyphenyl, or 1,4-bis-hydroxyphenyl, or 1,4-bis-hydroxyphenyl) -propanone, or the compounds 1,2-bis-bis-bis-hydroxyphenyl, 1,4-bis-bis-hydroxyphenyl, 1,4-bis-bis-hydroxyphenyl, 1,4-bis-bis-hydroxypropanene, 1,2-bis-bis-bis-hydroxypropanene, or 1,2-bis-bis-bis-hydroxyphenyl, Other
The polymers of component a) can be linear or branched. The forming process of these polymers takes place at relatively high temperatures, e.g. polycarbonate is injected at 220-330°C. At these temperatures most of the usual photostimulators and antioxidants are unstable and begin to decompose.
If R is a C1-C18 alkyl in formula I, it may be a linear or branched alkyl and may be e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, 2-ethylbutyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, dodecyl, tetradecyl or octadecyl. R as a C2-C6 alkyl substituted by a halogen or C1-C12 alkoxy may be e.g. 2-chloroethyl, 2-fluorethyl, 2-methoxyethyl, 2-fluoroxyethyl, 2-isoproproxyethyl, 2-methoxyethyl, 3-methoxypropyl, 2-butoxyethyl, 2-exythyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-ethyl, 2-
R is preferred for C1-C12 alkyl or benzyl, especially C3-C6 alkyl, especially propyl.
In formula I, R' means hydrogen.
Examples of compounds of formula I are: The term 'sugar' means any foodstuff that is manufactured from any of the following ingredients: sugar, fats, oils, starches, fats and oils obtained from the extraction of sugar, fats and oils obtained from sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugar-cane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugarcane, sugar
The compounds of formula I are known compounds or can be produced by analogy to known compounds. The production can be done in principle by etherisation of the corresponding 2,4-diaryl-6-(2,4-dihydroxyphenyl)-1,3,5-triazine. The etherisation is selectively done in position 4 because the OH group in position 2 is sterically inhibited by hydrogen bridge binding.
The amount of stabilizer to be used depends on the polymer to be stabilized and the intended use of the stabilized polymer.
The stabilizer (component b) may also be a mixture of two or more compounds of formula I. In addition to the stabilizer of formula I, the polymer composition may contain other known stabilizers, such as antioxidants, photosensitizers, metal desactivators or processing stabilizers. The use of the active substance in the active substance shall be authorised in accordance with the provisions of Regulation (EC) No 1907/2006, and in particular the provisions of Regulation (EC) No 1907/2006 and Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 16 December 2006 on the placing of active substances in foodstuffs for human consumption and on the placing on the market of active substances for human consumption and on the placing on the market of active substances for human consumption and on the placing on the market of active substances for human consumption and on the placing on the market of active substances for human consumption and on the placing on the market of active substances for human consumption and on the placing on the market of active substances for human consumption and on the placing on the market of active substances for human consumption and on the placing on the market of active substances for human consumption and on the placing on the market of active substances for human consumption.The term 'methylbenzyl bisphenol' means a methylbenzyl bisphenol containing a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphorus of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate, a phosphor of ethyl methacrylate6,7-trioxabyclo[2.2.2]-octan.1.13. ester of β-tetrahydroxy-3-methylphenyl) propionic acid with one or more alcoholic strengths, such as methanol, ethanol, octadecanol, 1,6-hexandiol, 1,9-nonandiol, ethylene glycol, 1,2-propanediol, neopentylglycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, n-ethylene glycol, n-ethylene glycol, tri-diethylene glycol, tri-diethylene glycol, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl, n-methyl n-methyl, n-methyl n-methyl, n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-methyl n-The term 'diethyl methacrylate' means a diethyl methacrylate containing a mixture of 5-Chlor-3'-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-methyl-meth5-di-di-di-butylbenzylphosphonic acid monoalkylers such as methyl or ethyl ester, nickel complexes of ketoximen such as 2-hydroxy-4-methylphenylundecylenetoxim, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazol, with any additional ligands.2.6. sterically inhibited amines such as bis-di-di-benzylphosphonic acid monoalkylers such as bis-di-di-2,6,6-tetramethylpiperidyl) -di-methyl or ethyl ester, bis-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-di-diThe following compounds are to be classified as 'dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxy-dioxyFor example, Ca-stearate, Zn-stearate, Mg-benhate, Mg-stearate, Na-ricinoleate, K-palmitate, antimony bromine catechinate or tin bromine catechinate.8. Nucleating agents such as 4-tert.Butyl benzoic acid, adipic acid, diphenyl acetic acid.9. Fillers and reinforcers such as calcium carbonate, silicates, glass fibres, asbestos, talc, kaolin, glitter, barium sulphate, metal oxides and hydroxides, russ, graphite.10. Other additives such as plasticizers, lubricants, emulsifiers, pigments, optical resistive agents, flame retardants, flame retardants, fuel.
The addition of the stabiliser and, where appropriate, further additives to the polymer shall be carried out preferably before the forming process, for example by mixing the powdered components or by adding the stabiliser to melt or dissolve the polymer.
The invention therefore also relates to a method for stabilizing thermoplastic polymers containing heteroatoms in the main chain against damage by light, oxygen and heat, characterized by the addition of at least one compound of formula I as a stabilizer, and the use of compounds of formula I to stabilize thermoplastic polymers containing heteroatoms in the main chain against damage by light, oxygen and heat.
The resulting stabilised polymer compositions can be converted into moulded articles, such as fibres, films, strips, plates, boards, vessels, tubes and other profiles, by the usual methods, such as hot pressing, spinning, extrusion or injection moulding.
The invention therefore continues to apply to the use of the polymer composition of the invention for the manufacture of a moulded article.
The application may be simultaneous with the shaping of the base material, e.g. by so-called coextrusion. However, the application may also be carried out on the finished base material, e.g. by lamination with a film or by coating with a solution. The outer layer or layers of the finished material have the function of a UV filter, which protects the inner layer of the base material against UV light, in particular the outer layer of the base material, which contains at least 5-10% of the base material.
The use of the polymer composition of the invention to produce multilayer systems, where the outer layer consists of a polymer composition of the invention in a thickness of 10-100 μm, while the inner layer consists of a polymer containing, where appropriate, little or no stabilizer of formula I, is therefore another subject matter of the invention.
Of particular interest is the use of a polymer composition of the invention, the component of which is (a) a polycarbonate, for the manufacture of multilayer systems.
The polymers thus stabilised are characterised by their high resistance to weathering, particularly UV light, which keeps their mechanical properties, colour and shine for a long time even when used outdoors.
The following examples explain the invention in more detail, without limiting them to the examples, in which parts and percentages refer to parts and percentages by weight; room temperature means a temperature between 20 and 25°C. The following UV absorbers are used: The following substances are to be classified in the additive: sulphur dioxide, sulphur dioxide, sulphur dioxide, sulphur dioxide, sulphur dioxide, sulphur dioxide, sulphur dioxide, sulphur dioxide, sulphur dioxide, sulphur dioxide and sulphur dioxide, in the form of a solution in which the ammoniacal and other volatile organic compounds are incorporated:
Example 1: 10 g of polyarbonate powder (Lexan® 115) are dissolved in 50 g of methylene chloride by stirring at room temperature, which takes several hours, and 0.1 g, 0.2 g or 0.5 g of UV absorber, respectively 1, 2 and 5% added concentration.
The films are exposed to an Atlas Weatherometer CI 65 at a black-field temperature of 63°C and a relative humidity of 60%. The colouration of the samples is checked at regular intervals by measuring the Yellowness Index (YI, ASTM D 1925 method).
The films are then exposed further until the film is scattered, which is manifested by the formation of cracks in the films. Other Tabelle 1:
Belichtungszeit (h) bis zum Erreichen eines Yellowness Index (YI) = 7 sowie bis zum Verspröden
Belichtungszeit (h) bis
UV-Absorber YI=7 Versprödung
keiner 990 1100
1 % Xy-1 1700 3900
1 % Ph-1 2200 4100
1 % To-1 2100 4020
2 % Xy-1 1800 4500
2 % Ph-1 2300 7740
2 % To-1 2100 6680
5 % Xy-1 1900 6000
5 % Ph-1 5700 10990
5 % To-1 4000 10990
Example 2: Films produced according to the rule described in Example 1 are aged in a circulator at 140°C. As in Example 1, the aging time to a yellowness index of 7 and the time to dispersion are measured.
Table 2 shows the results obtained. Other Tabelle 2:
Alterungszeit (h) bis zum Erreichen eines Yellowness Index (YI) = 7 sowie bis zum Verspröden
Zeit in Stunden bei 140°C bis
UV-Absorber YI=7 Versprödung
1 % Xy-1 500 2100
1 % Ph-1 3250 3250
1 % To-1 2440 2900
2 % Xy-1 300 1500
2 % Ph-1 3350 3500
2 % To-1 1300 2350
5 % Xy-1 120 700
5 % Ph-1 2940 3000
5 % To-1 1150 1700
Example 3: Polycarbonate powder is mixed with 0,3% of different UV absorbers and processed into granules in a double-shell extruder at 275°C mass temperature and 25 upm.
The granules are processed on a injection moulding machine (240/300°C/75 bar) into 67x43x2 mm plates, exposed to an Atlas Weatherometer CI 65 as in example 1, and the exposure time up to a Yellowness Index of 25 (YI measured according to ASTM D-1925) is given in Table 3. Tabelle 3:
Belichtungszeit (h) bis zum Erreichen eines Yellowness Index (YI) = 25
UV-Absorber Belichtungszeit (h) bis YI= 25
keiner 900
0,3 % Xy-1 2700
0,3 % Ph-1 3500
0,3 % To-1 3100
Example 4: Polycarbonate films containing 2% by weight of UV absorbers are produced and exposed using the method described in Example 1 and the exposure time to a Yellowness Index of 7 is shown in Table 4.
The films are then exposed to further exposure until they are dispersed, the exposure time also shown in Table 4. Other Tabelle 4:
Belichtungszeit (h) bis zum Erreichen eines Yellowness Index (YI) = 7 sowie bis zum Verspröden
UV-Absorber Belichtungszeit (h) bis
YI=7 Versprödung
keiner 990 1100
2 % Ph-2 2480 8040
2 % Ph-3 2560 5900
2 % Ph-4 2560 5550
2 % Ph-5 2690 7540
2 % To-2 2270 5900
2 % To-3 2400 5550
2 % To-4 2375 5060
2 % Xy-2 1850 3900
2 % Xy-3 1860 3900
2 % Xy-4 1950 3900
Example 5: Films produced according to the rule described in Example 4 are aged in a circulator at 130°C. As in the example above, the aging time is measured to a yellowness index of 7 and the time to dispersion.
Table 5 shows the results obtained. Other Tabelle 5:
Alterungszeit (h) bis zum Erreichen eines Yellowness Index (YI) = 7 sowie bis zum Verspröden
Zeit in Stunden bei 130°C bis
UV-Absorber YI=7 Versprödung
2 % Ph-2 1840 7000
2 % Ph-3 5030 7000
2 % Ph-4 4170 7000
2 % Ph-5 5580 8000
2 % To-2 2460 4720
2 % To-3 2790 4720
2 % To-4 2750 4720
2 % Xy-2 750 3030
2 % Xy-3 790 2530
2 % Xy-4 820 3030
Example 6: As described in Example 1, polycarbonate films containing 2% by weight of UV absorbers are produced and exposed. The tensile strength of the films is measured at regular intervals at room temperature (cross-speed 20 mm/min, DIN 53448/1 dumb-bell). Other Tabelle 6
UV-Absorber Belichtungszeit (h) bis 50% Zugfestigkeit
keiner 690
2 % Xy-1 1420
2 % Ph-1 1670
2 % To-1 1860
Example 7: 3 kg of polybutylene terephthalate powder (Crastin® S 600) are mixed with 0.1% by weight of pentaerythrityl tetrachsis ((3-[3',5'-di-tert.butyl-4'-hydroxyphenyl]propionate), 0.4% by weight of tristyl (2,4-di-tert.butylphenyl) phosphate and 0.5% by weight of the UV absorber specified in Table 7 in a Henschel blender for 2 minutes dry and then granulated in a Berstorff double-slotted extruder at 100 rpm and a temperature setting of 230°C/240°C/250°C/250°C. Each mixture is prepared with a spraying machine (Littleburg type, LC, LC, LC) with a thickness of 1 mm x 70 mm and a tool measuring 70 mm x 70 mm.
The plates are exposed to a black-field temperature of 63°C and a relative humidity of 60%, after 30 days of storage at room temperature in an Atlas Weatherometer CI 65, with a wet cycle of 102 min dry/18 min wet. At regular intervals, the discoloration of the samples is checked by measuring the Yellowness Index (YI, ASTM D 1925 method). Table 7 shows the exposure time during which an increase in the Yellowness Index of ΔYI = 10 occurs. Other Tabelle 7
UV-Absorber Belichtungszeit (h) bis ΔYI = 10
0.5 % Xy-1 1520
0.5 % To-1 2850
0.5 % Ph-1 3130
Example 8: Polyamide-6 powder (Ultramid® B3S, manufacturer BASF) is mixed with the stabilizers given in Table 8 in a Henschel mixer for 2 minutes and then processed in a Berstorff double-slip extruder at a speed of 95/min and a temperature setting of 230°C/235°C/240°C/240°C. The amounts of stabilizer are given in % by weight, based on the amount of polyamide used. Each mixture is prepared by means of a spray casting system (Arburg L type, material temperature 240°C, tool temperature 80°C) to produce sheets of 2 mm thickness.
The plates are exposed to an Atlas Weatherometer CI 65 at a black-field temperature of 63°C and a relative humidity of 60%, with a wet cycle of 102 min. dry/18 min. The time taken for the cracks to become visible on the plates is measured.
In addition to the stabilizers of the invention mentioned above, the following additional stabilizers are used: A N,N'-Bis(3-[3',5'-di-tert.butyl-4'-hydroxyphenyl]-propionyl)hexamethylenediamine, with a Bris T ((2,4-di-tert-butyl-phenyl) phosphite, C Condensation product of N,N'-bis- ((2,2,6,6-tetramethyl-4-piperidyl) -hexamethylenediamine and 4-tert.Octylamino-2,6-dichlor-1,3,5-s-triazine at a temperature between 120 and 150 °C. Other Tabelle 8:
Zeit (h) bis zum Auftreten von Rissen
Stabilisatoren Zeit (h)
keiner 1050
0.2 % A + 0.2 % B 2620
0.2 % A + 0.2 % B + 0.3 % Xy-1 2950
0.2 % A + 0.2 % B + 0.3 % To-1 3320
0.2 % A + 0.2 % B + 0.3 % Ph-1 3930
0.2 % A + 0.2 % B + 0.3 % Xy-1 + 0.3 % C 5900
0.2 % A + 0.2 % B + 0.3 % To-1 + 0.3 % C 6200
0.2 % A + 0.2 % B + 0.3 % Phl + 0.3 % C >6200
Example 9: Polyoxymethylene (Hostaform® C) is used in a Brabender plastic order containing 0.3% by weight of calcium stearate, 0.3% by weight of a stabiliser of the formula and 0,3% by weight of the UV absorber specified in Table 9 for 7 minutes at 190°C and 30 revolutions/minute. The plates are exposed to a UV-A source at 60°C and 23% humidity at a distance of 20 cm. The UV-A source consists of 5 fluorescent lamps TL/09 and 5 lamps TL/12 (wavelength range 295-400 nm). At regular intervals, the Yellowness Index (YI, ASTM D 1925 method) is measured, which is the maximum that passes through the UV exposure of polyoxymethylene. This maximum is caused by the first appearance of microscopic cracks not yet visible visually. Other Tabelle 9:
Belichtungsdauer in Wochen bis YI-Maximum bezw. bis zum Auftreten von visuell feststellbaren Rissen auf den Probenplatten
Belichtungsdauer (Wochen) bis
UV-Absorber YI-Maximum Rissbildung
0.3 % Xy-5 8 16
0.3 % To-5 10 20
0.3 % Ph-5 16 25
The test results given in examples 1 to 9 show significantly improved properties when using the stabilizers of the invention (diphenyl and dip-tolylderivatives of 1,3,5-triazine) compared to the known dixylderivatives.

Claims (12)

  1. A polymer composition stabilised against damage by light, oxygen and heat, comprising
    a) at least one thermoplastic polymer that comprises hetero atoms in the main chain, and
    b), as stabiliser, at least one hydroxyphenyltriazine compound of formula I wherein R is hydrogen, C1-C18alkyl, C2-C6alkyl substituted by halogen or by C1-C12alkoxy, or is benzyl and R' is hydrogen or methyl, with the exception of compositions obtained by treating fibre material of component (a) with the stabiliser component (b).
  2. A polymer composition according to claim 1, wherein component a) is a polycarbonate, polyester, polyamide, polyacetal, polyphenylene oxide or polyphenylene sulfide.
  3. A polymer composition according to claim 1, wherein component a) is a polycarbonate.
  4. A polymer composition according to claim 1, wherein component b) is a compound of formula I wherein R is C1-C12alkyl or benzyl.
  5. A polymer composition according to claim 1, wherein component b) is a compound of formula I wherein R is C3-C6alkyl.
  6. A polymer composition according to claim 1, wherein component b) is a compound of formula I wherein R' is hydrogen.
  7. A polymer composition according to claim 1, comprising from 0.1 to 15 parts by weight of the stabiliser component b) per 100 parts by weight of the polymer component a).
  8. A polymer composition according to claim 1, comprising in addition to components a) and b) one or more other stabilisers or other additives.
  9. A method for stabilising thermoplastic polymers that comprise hetero atoms in the main chain against damage by light, oxygen and heat, wherein a compound of formula I according to claim 1 is added thereto as stabiliser.
  10. The use of a compound of formula I according to claim 1 for stabilising thermoplastic polymers that comprise hetero atoms in the main chain against damage by light, oxygen and heat.
  11. The use of the polymer composition defined in claim 1 for the production of a shaped article.
  12. The use according to claim 11 for the production of multi-layer systems wherein the outer layer(s) consist(s) of a polymer composition according to claim 1 in a thickness of 10 - 100 µm, while the inner layer consists of a polymer that may comprise little or no stabiliser of formula I.
HK98101303A 1991-02-21 1998-02-19 Stabilised polymers containing heteroatoms in the main chain HK1002331A1 (en)

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