Additive mixtures for stabilizing organic materials
Patent Information
- Application Number
- JP2024502459
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2021-07-17
- Filing Date
- 2022-07-15
- Publication Date
- 2025-07-22
AI Technical Summary
Existing additives such as hindered amine light stabilizers and UV absorbers fail to significantly improve the stability of organic materials exposed to UV light, leading to instability and reduced lifespan of articles made from these materials.
A combination of UV absorbers and a specific compound of formula (A) with stabilized organic materials enhances the stability of organic materials by improving durability and extending the lifespan of the final article.
The additive mixture improves the durability and lifespan of organic materials exposed to light, providing economic value through prolonged product life.
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Abstract
Description
[Technical field]
[0001] The present invention relates to a composition comprising a stabilized organic material, at least one compound of formula (A) and at least one UV absorber.The present invention also relates to an additive mixture comprising at least one compound of formula (A) and at least one UV absorber.The present invention also relates to the use of this additive mixture for improving the stability of the stabilized organic material exposed to light. [Background technology]
[0002] Organic materials, i.e., synthetic polymers such as polyolefins and polyethylene, are widely used because they can be easily used to manufacture various extruded and molded articles. However, many of these articles suffer from general instability due to repeated exposure to UV light. To prevent articles made from organic materials from the harmful effects of UV light, various additives, such as hindered amine light stabilizers, UV absorbers, etc., are used. However, these additives or mixtures of these additives cannot significantly improve the stability of organic materials. Summary of the Invention [Problem to be solved by the invention]
[0003] It is therefore an object of the present invention to overcome the above mentioned drawbacks and to provide an additive mixture for stabilizing organic materials. [Means for solving the problem]
[0004] Surprisingly, it has been found that the additive mixture of the present claimed invention, i.e., the combination of a UV absorber and / or HALS with a compound of formula (A) and a stabilized organic material, improves the durability of the final article exposed to light, thus extending the life of the final article and, as a result, imparting economic value.
[0005] In one aspect, the claimed invention comprises: i. a stabilized organic material; ii. At least one compound of formula (A): [ka] (In the formula, E1 is hydrogen, C 1 ~C 18 Alkyl, formula P: [ka] (Wherein R, R' and R'' are each independently C 1 ~C 18 is alkylene, and b is an integer ranging from 1 to 3; Formula Q: [ka] (Wherein, T and U are each independently a linear or branched C 1 ~C 18 alkyl), E 2 , E 3 , E 4 , E 5 and E 6 are independently hydrogen, C 1 ~C 18 Alkyl, phenyl or 1, 2 or 3 C 1 ~C 4 Alkyl-substituted phenyl or a compound of formula Q: [ka] (Wherein, T and U are each independently a linear or branched C 1 ~C 18 with a compound of formula (I) (I) (I); iii. at least one UV absorber; The present invention relates to a composition comprising:
[0006] In another aspect, the claimed invention provides: I. at least one compound of formula (A) as defined above, II. at least one UV absorber; The present invention relates to an additive mixture comprising:
[0007] In yet another aspect, the claimed invention relates to the use of the additive mixture to improve the stability of stabilized organic materials exposed to light. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0008] Before describing the compositions and formulations of the present invention, it is to be understood that the invention is not limited to the particular compositions and formulations described, as such compositions and formulations may, of course, vary. It is also to be understood that the terms used herein are not intended to be limiting, since the scope of the invention as claimed herein will be limited only by the appended claims.
[0009] Hereinafter, when a group is defined as including at least a certain number of embodiments, this is meant to include preferred groups consisting of only these embodiments. Furthermore, the terms "first", "second", "third" or "(a)", "(b)", "(c)", "(d)" and the like in this specification and claims are used to distinguish similar components and do not necessarily describe a sequential or chronological order. It should be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the invention described herein can be implemented in other orders than those described or illustrated herein. Where the terms "first", "second", "third" or "(A)", "(B)" and "(C)" or "(a)", "(b)", "(c)", "(d)", "i", "ii" etc. refer to steps of a method or use or assay, unless otherwise specified in this application, as described hereinbefore or hereinafter, there may be no time interval or no consistent time interval between such steps, i.e., the steps may be performed simultaneously or the time interval between such steps may be seconds, minutes, hours, days, weeks, months or even years.
[0010] In the following text, the different aspects of the invention are defined in more detail. Each aspect so defined may be combined with any other aspect or aspects, unless expressly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features indicated as being preferred or advantageous.
[0011] References throughout this specification to "one embodiment" or "preferred embodiment" mean that a particular feature, structure, or characteristic described in connection with that embodiment is included in at least one embodiment of the claimed invention. Thus, the appearance of the phrases "in one embodiment" or "in a preferred embodiment" or "in another embodiment" in various places throughout this specification may, but do not necessarily, all refer to the same embodiment. Moreover, as would be apparent to one of ordinary skill in the art from this disclosure, particular features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. Furthermore, as would be understood by one of ordinary skill in the art, an embodiment described herein may include some features included in other embodiments but not others, meaning that combinations of features of different embodiments are within the scope of the invention and form different embodiments. For example, in the appended claims, any of the claimed embodiments may be used in any combination.
[0012] Furthermore, ranges defined throughout this specification are inclusive, i.e., a range of 1 to 10 means that both 1 and 10 are included within the range. For the avoidance of doubt, Applicant reserves the right to any and all equivalents, pursuant to applicable law.
[0013] In order that this disclosure may be more readily understood, certain terms are first defined. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which embodiments of the present invention pertain.
[0014] In one aspect, the claimed invention comprises: i. a stabilized organic material; ii. At least one compound of formula (A): [ka] (In the formula, E1 is hydrogen, C 1 ~C 18 Alkyl, formula P: [ka] (Wherein R, R' and R'' are each independently C 1 ~C 18 is alkylene, and b is an integer ranging from 1 to 3; Formula Q: [ka] (Wherein, T and U are each independently a linear or branched C 1 ~C 18 alkyl), E 2 , E 3 , E 4 , E 5 and E 6 are each independently hydrogen, C 1 ~C 18 Alkyl, phenyl or 1, 2 or 3 C 1 ~C 4 Alkyl-substituted phenyl or a compound of formula Q: [ka] (Wherein, T and U are each independently a linear or branched C 1 ~C 18 with a compound of formula (I) (I) (I); iii. at least one UV absorber; The present invention relates to a composition comprising:
[0015] In one embodiment, the stabilized organic material is selected from the group consisting of polyethylene, polypropylene, polyurethane, styrenic polymers, polyvinyl chloride, and mixtures thereof.
[0016] In a preferred embodiment, the stabilized organic material is polyvinyl chloride, which may be rigid, semi-rigid or flexible polyvinyl chloride.
[0017] In one embodiment, the stabilized organic material comprises at least one plasticizer, at least one thermal stabilizer, and mixtures thereof.
[0018] The at least one plasticizer may be selected from the group consisting of phthalates, dialkyl cyclohexane-1,2-dicarboxylates, dialkyl cyclohexane-1,3-dicarboxylates, dialkyl cyclohexane-1,4-dicarboxylates, dialkyl terephthalates, esters of trimellitic acid, trialkyl trimellitates, alkyl benzoates, dibenzoates of glycols, pentaerythritol esters, hydroxybenzoates, monoesters, esters of saturated monocarboxylic acids, esters of unsaturated monocarboxylic acids, esters of saturated dicarboxylic acids, esters of unsaturated dicarboxylic acids, aryl esters of aromatic sulfonic acids, and the like. and mixtures thereof.
[0019] Phthalate esters include dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, di-2-ethylhexyl phthalate, di-n-octyl phthalate, disooctyl phthalate, diisononyl phthalate, diisononyl hexahydrophthalate, diisodecyl phthalate, diisotridecyl phthalate, dicyclohexyl phthalate, dimethylcyclohexyl phthalate, dimethyl glycol phthalate, dibutyl glycol phthalate, benzyl butyl phthalate and diphenyl phthalate, as well as mixtures of phthalates, e.g., phthalate C produced mainly from linear alcohols. 7 ~C 9 - and C 9 ~C 11 Alkyl ester, phthalic acid C6 ~C 10 -n-Alkyl esters and phthalic acids C 8 ~C 10 -n-alkyl esters, preferably diisononyl.
[0020] The epoxy plasticizer is selected from the group consisting of epoxidized soybean oil, epoxidized linseed oil and octyl oleate, preferably epoxidized soybean oil.
[0021] The at least one heat stabilizer is selected from the group consisting of metal salts of fatty acids, complex metal stabilizers, organotin stabilizers, lead stabilizers, organic stabilizers and mixtures thereof, preferably complex metal stabilizers.
[0022] Metal salts of fatty acids are fatty saturated C 2 ~C 22 Carboxylate, Aliphatic Olefinic C 3 ~C 22 Carboxylate, aliphatic C substituted with at least one OH group 2 ~C 22 Carboxylic acid salts, cyclic or bicyclic C 5 ~C 22 Carboxylate, aromatic C 7 ~C 22 Carboxylate, aromatic C substituted with at least one OH group 7 ~C 22 Carboxylate, C 1 ~C 16 Alkyl-substituted phenyl carboxylates and phenyl-C 1 ~C 16 The alkyl carboxylate series may be selected from the group consisting of calcium, zinc, magnesium or aluminium salts.
[0023] The metal salt of a fatty acid is selected from the group consisting of calcium stearate, zinc octanoate, zinc oleate, zinc stearate and zinc laurate.
[0024] The complex metal stabilizer is a barium / zinc or calcium / zinc stabilizer.
[0025] The organotin stabilizer is selected from the group consisting of organotin mercaptoesters, organotin carboxylates and organotin sulfides.
[0026] The lead stabilizer is selected from the group consisting of tribasic lead sulfate, dibasic lead sulfate, dibasic lead phthalate, dibasic lead phosphate and lead stearate.
[0027] Compounds of formula (A): In one embodiment, the composition comprises at least one compound of formula (A): [ka] Includes.
[0028] In one embodiment, E 1 is hydrogen, C 1 ~C 18 alkyl, a group of formula P or a group of formula Q, preferably hydrogen, C 1 ~C 8 Alkyl, formula P: [ka] (Wherein R, R' and R'' are each independently C 1 ~C 18 alkylene, preferably R, R' and R'' are each independently 2 ~C 10 alkylene) or a group of formula Q, where b is an integer in the range of 1 to 3, preferably b is an integer in the range of 1 to 2.
[0029] In one embodiment, when b is 1, E 1 is hydrogen, alkyl or a group of formula Q; when b is 2, E 1 is a group of formula P.
[0030] In one embodiment, E 2 , E 3 , E 4 , E 5 and E 6are each independently hydrogen, C 1 ~C 18 Alkyl, phenyl or 1, 2 or 3 C 1 ~C 4 is a phenyl substituted with alkyl or a group of formula Q, preferably E 2 , E 3 , E 4 , E 5 and E 6 are each independently hydrogen, C 1 ~C 4 It is alkyl, phenyl or a group of formula Q.
[0031] Examples of alkyl having up to 18 carbon atoms are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl.
[0032] Examples of alkylenes having 18 or fewer carbon atoms are methylene, ethylene, propylene, isopropylene, n-butylene, sec-butylene, isobutylene, tert-butylene, 2-ethylbutylene, n-pentylene, isopentylene, 1-methylpentylene, 1,3-dimethylbutylene, n-hexylene, 1-methylhexylene, n-heptylene, isoheptylene, 1,1,3,3-tetramethylbutylene, 1- Methylheptylene, 3-methylheptylene, n-octylene, 2-ethylhexylene, 1,1,3-trimethylhexylene, 1,1,3,3-tetramethylpentylene, nonylene, decylene, undecylene, 1-methylundecylene, dodecylene, 1,1,3,3,5,5-hexamethylhexylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, and octadecylene.
[0033] In a preferred embodiment, the at least one compound of formula (A) is represented by the formulas (A-1), (A-2), (A-3), (A-4) and (A-5): [ka] [ka] is selected from.
[0034] Many of the compounds of formula (A) are known or may be prepared analogously to processes known to those skilled in the art.
[0035] Compounds of formula (A) can be prepared, for example, similarly to the methods described in US Pat. No. 6,255,483B.
[0036] In one embodiment, the UV absorber is selected from the group consisting of 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyphenyl)-1,3,5-triazines, esters of substituted and unsubstituted benzoic acids, cyanoacrylates, oxanilides, benzoxazinones, and mixtures thereof.
[0037] 2-(2'-hydroxyphenyl)benzotriazole is 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3'-t ert-butyl-2'-hydroxy-5'-methylphenyl)-5-chloro-benzotriazole, 2-(3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)benzotriazole, 2-(3',5'-bis-(α,α-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy- 5'-(2-octyloxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)-carbonylethyl]-2'-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3' -tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)benzotriazole, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenylbenzotriazole, 2,2'-methylene-bis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenol];2-[3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole transesterification product with polyethylene glycol 300;, [ka] wherein R=3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl; 2-[2'-hydroxy-3'-(α,α-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole; 2-[2'-hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5'-(α,α-dimethylbenzyl)-phenyl]benzotriazole; and mixtures thereof.
[0038] In a preferred embodiment, the 2-(2'-hydroxyphenyl)benzotriazole is selected from 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)-5-chloro-benzotriazole and mixtures thereof.
[0039] The 2-hydroxybenzophenone is selected from the group consisting of 2-hydroxy-4-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octyloxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4,2',4'-trihydroxybenzophenone, 2-hydroxy-2'-hydroxy-4,4'-dimethoxybenzophenone derivatives and mixtures thereof.
[0040] In a preferred embodiment, the 2-hydroxybenzophenone is 2-hydroxy-4-octyloxybenzophenone.
[0041] 2-(2-hydroxyphenyl)-1,3,5-triazine is 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine Triazine, 2-[4-(dodecyloxy / tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy]phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, )phenyl]-1,3,5-triazine, 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(4-[2-ethylhexyloxy]-2-hydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2-(4,6-bis-(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-(octyloxy)-phenol, bis{2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy]ethyl} dodecanedioate, and mixtures thereof.
[0042] In one embodiment, the esters of substituted and unsubstituted benzoic acids are selected from the group consisting of 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, and mixtures thereof, preferably 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.
[0043] In one embodiment, the cyanoacrylate is selected from the group consisting of ethyl α-cyano-β,β-diphenylacrylate, isooctyl α-cyano-β,β-diphenylacrylate, neopentyl tetra(α-cyano-β,β-diphenylacrylate), pentaerythritol tetrakis(2-cyano-3,3-diphenylacrylate), ethyl 2-cyano-3,3-diphenylacrylate, (2-ethylhexyl) 2-cyano-3,3-diphenylacrylate, and mixtures thereof.
[0044] In a preferred embodiment, the cyanoacrylate is pentaerythritol tetrakis(2-cyano-3,3-diphenylacrylate).
[0045] In one embodiment, the oxanilide is 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butyloxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butyloxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide ... and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butyloxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides and mixtures thereof, preferably the oxanilide is 2-ethoxy-2'-ethyloxanilide.
[0046] In one embodiment, the benzoxazinone is 2,2'-(1,4-phenylene)bis[4H-3,1-benzoxazin-4-one].
[0047] In one embodiment, the composition further comprises at least one compound (B) selected from general formula (I), general formula (II), general formula (III), general formula (IV), and mixtures thereof.
[0048] Compound (B) of general formula (I): [ka] (In the formula, A 1 is a linear or branched, substituted or unsubstituted C 2 ~C 18 Alkylene, substituted or unsubstituted C 5 ~C 7 Cycloalkylene and C 1 ~C 4 Alkylene Diene (C 5 ~C 7 cycloalkylene; A 2 is H, linear or branched, substituted or unsubstituted C1 ~C 12 Alkyl, C 1 ~C 12 Alkyloxy, substituted or unsubstituted C 5 ~C 12 Cycloalkyl and C 5 ~C 12 cycloalkyloxy; A 3 and A 4 is H, linear or branched, substituted or unsubstituted C 1 ~C 12 Alkyl, substituted or unsubstituted C 5 ~C 12 Cycloalkyl and formula (a-1): [ka] or A 3 and A 4 together with the nitrogen atom to which they are attached form a 5- to 10-membered heterocyclic ring; a is an integer ranging from 1 to 20, and the repeating units are the same or different.
[0049] In the context of the present invention, the term alkyl as used herein denotes acyclic saturated aliphatic residues including linear or branched alkyl residues.
[0050] "Branched," as used herein, refers to a chain of atoms having one or more side chains attached thereto. The branching is created by the replacement of a hydrogen atom with a substituent, for example a covalently bonded aliphatic moiety.
[0051] Linear and branched unsubstituted C 1 ~C 12Representative examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, 2-propylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, n-nonyl, n-decyl, n-undecyl, isoundecyl, 1-methylundecyl, n-dodecyl, isododecyl, and 1,1,3,3,5,5-hexamethylhexyl.
[0052] C 1 ~C 12 Representative examples of alkyloxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, nonyloxy, decyloxy, undecyloxy, and dodecyloxy.
[0053] In a preferred embodiment, the alkyloxy is selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, and octoxy. In a more preferred embodiment, the alkyloxy is propoxy.
[0054] C 5 ~C 12 Representative examples of cycloalkyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, and cyclododecyl.
[0055] C 5 ~C 12Representative examples of cycloalkyloxy are cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclononyloxy, cyclodecyloxy, cycloundecyloxy, and cyclododecyloxy.
[0056] In a preferred embodiment, cycloalkyloxy is cyclohexoxy.
[0057] 1, 2 or 3 C's 1 ~C 4 A preferred example of alkyl-substituted phenyl is 2,4-dimethylphenyl.
[0058] Preferred C 2 ~C 18 Alkylene is ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene and hexamethylene. In a more preferred embodiment, alkylene is hexamethylene.
[0059] C 5 ~C 7 An example of a cycloalkylene is cyclohexylene.
[0060] C 1 ~C 4 Alkylene Diene (C 5 ~C 7 An example of a cycloalkylene is methylenedicyclohexylene.
[0061] A 3 and A 4 Examples of 5-10 membered heterocyclic rings which the groups form together with the nitrogen atom to which they are attached are 1-pyrrolidyl, piperidyl, morpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl, 1-hexahydroazepinyl, 5,5,7-trimethyl-1-homopiperazinyl or 4,5,5,7-tetramethyl-1-homopiperazinyl, preferably morpholinyl.
[0062] The terminal group bonded to the diamino residue of the compound (B) of the general formula (I) can be, for example, hydrogen or a group of the formula: [ka] and the terminal group attached to the triazine group is, for example, a group of the formula: [ka] A group or formula: [ka] is the basis.
[0063] In a preferred embodiment, A 1 is hexamethylene, and A 2 is hydrogen and propoxy.
[0064] In a preferred embodiment, A 3 is butyl, [ka] It is.
[0065] In a preferred embodiment, A 4 is butyl.
[0066] In a preferred embodiment, a is an integer in the range of 1-10.
[0067] Compound (B) of general formula (II): [ka] (In the formula, x 1 and x 2 is C 1 ~C 30 alkoxy)
[0068] In a preferred embodiment, x 1 and x 2 is a linear or branched unsubstituted C1 ~C 30 alkyloxy.
[0069] Linear or branched unsubstituted C 1 ~C 30 Representative examples of alkyloxy are methyloxy, ethyloxy, propyloxy, butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, icosyloxy, henicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy and triacontyloxy.
[0070] In a preferred embodiment, x 1 and x 2 are undecyloxy, respectively.
[0071] Compound (B) of general formula (III): [ka] (In the formula, Y 1 is a linear or branched, substituted or unsubstituted C 3 ~C 20 is alkyl, Y2 is C 1 ~C 30 alkyl); and
[0072] In a preferred embodiment, Y 1 is a linear or branched unsubstituted C 3 ~C 20 It is an alkyl.
[0073] In one embodiment, Y 1is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and icosyl.
[0074] In a preferred embodiment, Y 1 is selected from propyl or dodecyl.
[0075] In a preferred embodiment, Y 2 is a linear or branched unsubstituted C 1 ~C 30 It is an alkyl.
[0076] In one embodiment, Y 2 is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and triacontyl.
[0077] In a preferred embodiment, Y 2 is selected from pentadecyl or heptadecyl.
[0078] Compound (B) of general formula (IV): [ka] (In the formula, Y 1 is a linear or branched, substituted or unsubstituted C 3 ~C 20 is alkyl, Y 3 is a linear or branched, substituted or unsubstituted C 3 ~C 20 Alkyl and C 3 ~C 20independently selected from alkylidene; X is C 2 ~C 5 is alkyl, n is an integer ranging from 1 to 8.
[0079] In a preferred embodiment, Y 3 is a linear or branched unsubstituted C 3 ~C 20 Alkyl and C 3 ~C 20 Alkylidene is selected from the group consisting of:
[0080] Representative examples of alkylidene having up to 20 carbon atoms are methylidene, ethylidene, propylidene, butylidene, pentylidene, hexylidene, heptylidene, octylidene, nonylidene, decylidene, undecylidene, dodecylidene, tridecylidene, tetradecylidene, pentadecylidene, hexadecylidene, heptadecylidene, octadecylidene, nonadecylidene and icosylidene.
[0081] In a preferred embodiment, Y 1 is selected from decyl.
[0082] In a preferred embodiment, Y 3 is selected from decyl or nonylidene.
[0083] In a preferred embodiment, compound (B) is selected from formulas (B-1), (B-2), (B-3), (B-4), (B-5), (B-6), (B-7) and (B-8).
[0084] In a more preferred embodiment, compound (B) is a compound of formula (B-4). [ka] (wherein a is an integer ranging from 1 to 10), and [ka] [ka] [ka] (wherein n is 2).
[0085] In one embodiment, the composition further comprises at least one sterically hindered amine light stabilizer.
[0086] The at least one sterically hindered amine light stabilizer may be selected from the group consisting of bis(1-undecyloxy-2,2,6,6-tetramethyl-4-piperidyl)carbonate, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, bis(1,2,2,6 ,6-pentamethyl-4-piperidyl), condensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine with succinic acid, linear or cyclic condensation product of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine with 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)1,2,3,4-butanetetracarboxylate, 1,1'-(1,2-ethanediyl)-bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, 2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate bis(1,2,2,6,6-pentamethylpiperidyl), 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, bis(1-octyloxy-2,2,6,6-)sebacic acid tetramethylpiperidyl), bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, linear or cyclic condensation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine with 4-morpholino-2,6-dichloro-1,3,5-triazine, condensation products of 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5-triazine with 1,2-bis(3-aminopropylamino)ethane, condensation products of 2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine and 1,2-bis(3-aminopropylamino)ethane condensation product, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione, 3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione, 4-hexadecyloxy-2,2,6,6-tetramethylpiperidine and and 4-stearyloxy-2,2,6,6-tetramethylpiperidine; condensation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine with 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine; condensation products of 1,2-bis(3-aminopropylamino)ethane with 2,4,6-trichloro-1,3,5-triazine and 4-butylamino-2,2,6,6-tetramethylpiperidine; 1,6-hexanediamine and 2,4,6-trichloro-1,3,5-triazine and N,N-dibutyl Condensates of amines and 4-butylamino-2,2,6,6-tetramethylpiperidine; N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimide, N-(1,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylsuccinimide, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4,5]decane, 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro[4,5]decane with epichlorohydrin The product, 1,1-bis(1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl)-2-(4-methoxyphenyl)ethene, N,N'-bis-formyl-N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine, diester of 4-methoxymethylenemalonic acid with 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, poly[methylpropyl-3-oxy-4-(2,2,6,6-tetramethyl-4-piperidyl)]siloxane, maleic anhydride-α-olefin copolymer and 2,2,6,Reaction products with 6-tetramethyl-4-aminopiperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-butylamino]-6-(2-hydroxyethyl)amino-1,3,5-triazine, 1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, 5-(2-ethylhexanoyl)oxymethyl-3,3,5-trimethyl-2-morpholinone, 5 -(2-Ethylhexanoyl)oxymethyl-3,3,5-trimethyl-2-morpholinone, reaction products of 2,4-bis[(1-cyclohexyloxy-2,2,6,6-piperidin-4-yl)butylamino]-6-chloro-s-triazine with N,N'-bis(3-aminopropyl)ethylenediamine, 1,3,5-tris(N-cyclohexyl-N-(2,2,6,6-tetramethylpiperazin-3-one-4-yl)amino)-s-triazine, 1,3,5-tris(N-cyclohexyl-N-(1,2,2,6,6-pentamethylpiperazin-3-one-4-yl)amino)-s-triazine, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-N,N'-diformylhexamethylenediamine, 1,5,8,12-tetrakis[4,6-bis(n-butyl-n-1,2,2,6,6-pentamethyl-4-piperidylamino)- 1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane, N,N'"-[1,2-ethane-diyl-bis[[[4,6-bis-[butyl(1,2,2,6,6-pentamethyl-4-piperidinyl)amino]-1,3,5-triazin-2-yl]imino]-3,1-propanediyl]]bis[N',N"-dibutyl-N',N"-bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-1,3,5-triazine-2,4,6-triamine, N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,The polymer is selected from the group consisting of a polymer of 6-hexanediamine and morpholine-2,4,6-trichloro-1,3,5-triazine, poly(4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol-alt-1,4-butanedioic acid), and mixtures thereof.
[0087] In a preferred embodiment, the sterically hindered amine light stabilizer is N,N'"-[1,2-ethane-diyl-bis[[[4,6-bis-[butyl(1,2,2,6,6-pentamethyl-4-piperidinyl)amino]-1,3,5-triazin-2-yl]imino]-3,1-propanediyl]]bis[N',N"-dibutyl-N',N"-bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-1,3,5-triazine-2,4,6-triamine.
[0088] In a preferred embodiment, the sterically hindered amine light stabilizer is poly(4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol-alt-1,4-butanedioic acid).
[0089] In one embodiment, the composition further comprises at least one additive selected from the group consisting of slip agents, antiblocking agents, thermal fillers, pigments, anti-fog agents, and anti-mist agents.
[0090] In one embodiment, the composition further comprises at least one impact modifier selected from the group consisting of acrylic acid-butyl acrylate-2-ethylhexyl acrylate-methyl methacrylate polymer, methacrylate butadiene styrene (MBS), methacrylate / acrylonitrile-butadiene-styrene (MABS), acrylonitrile-butadiene-styrene (ABS), chlorinated polyethylene (CPE), ethylene vinyl acetate (EVA), polymethyl methacrylate (PMMA), and ethylene propylene diene monomer (EPDM).
[0091] In one embodiment, the weight ratio of the stabilized organic material to the total weight of the at least one compound of Formula (A) and the at least one UV absorber is in the range of 99.9:0.1 to 99:1.
[0092] In one embodiment, the weight ratio of the at least one compound of Formula (A) to the at least one UV absorber ranges from 1:50 to 50:1.
[0093] The composition may further include various conventional additives such as, for example, those listed below.
[0094] 1. Antioxidants 1.1. Alkylated monophenols, such as 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, nonylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear or branched nonylphenols, for example, 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methyltridec-1'-yl)phenol, and mixtures thereof.
[0095] 1.2. Alkylthiomethylphenols, for example 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol.
[0096] 1.3. Hydroquinone and alkylated hydroquinones, such as 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl)adipate.
[0097] 1.4. Tocopherols, such as α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol and mixtures thereof (vitamin E).
[0098] 1.5. Hydroxylated thiodiphenyl ethers, such as 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide.
[0099] 1.6. Alkylidene bisphenols, such as 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidene bis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis[6-(α-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-methylenebis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl) Butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene Ene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate, 1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis(5-tert-butyl-4-hydroxy2-methylphenyl)-4-n-dodecylmercaptobutane, 1,1,5,5-tetra-(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane.
[0100] 1.7. O-, N- and S-benzyl compounds, such as 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate.
[0101] 1.8. Hydroxybenzylated malonic acid esters, such as dioctadecyl 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, didodecylmercaptoethyl 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl] 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.
[0102] 1.9. Aromatic hydroxybenzyl compounds, such as 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.
[0103] 1.10. Triazine compounds, such as 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bi(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,5-triazine, phenoxy)-1,2,3-triazine, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate.
[0104] 1.11. Benzylphosphonic acid esters, for example, dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, calcium salts of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.
[0105] 1.12. Acylaminophenols, for example, 4-hydroxylauric acid anilide, 4-hydroxystearic acid anilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.
[0106] 1.13. Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, such as methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.
[0107] 1.14. Esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with monohydric or polyhydric alcohols, such as methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydro)isocyanurate, oxyethyl), N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane; esters with 3,9-bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane.
[0108] 1.15. Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, such as, for example, methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.
[0109] 1.16. Esters of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with mono- or polyhydric alcohols, such as methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.
[0110] 1.17. Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide, N,N'-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyloxy)ethyl]oxamide (Naugard® XL-1 supplied by Uniroyal).
[0111] 1.18. Ascorbic acid (vitamin C).
[0112] 1.19. Amine antioxidants, such as N,N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-bis(1-methylheptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, Diamine, N,N'-bis(2-naphthyl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4-(p-toluenesulfamoyl)diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-p -phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamines such as p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-Octadecanoylaminophenol, Bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetramethyl-4,4'-diaminodiphenylmethane, 1,2-bis[(2-methylphenyl)amino]ethane, 1,2-bis(phenylamino)propane, (o-tolyl)biguanide, bis[4-(1',3'-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, mixtures of mono- and di-alkylated tert-butyl / tert-octyldiphenylamines, mixtures of mono- and di-alkylated nonyldiphenylamines, mixtures of mono- and di-alkylated dodecyldiphenylamines, mixtures of mono- and di-alkylated isopropyl / isohexyldiphenylamines, mixtures of mono- and di-alkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mixtures of mono- and di-alkylated tert-butyl / tert-octylphenothiazines, mixtures of mono- and di-alkylated tert-octylphenothiazines, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene.,
[0113] 2.UV absorbers and light stabilizers 2.1. Esters of substituted and unsubstituted benzoic acids, for example, 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.
[0114] 2.2. Acrylic esters, for example, ethyl α-cyano-β,β-diphenylacrylate, isooctyl α-cyano-β,β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, butyl α-cyano-β-methyl-p-methoxycinnamate, methyl α-carbomethoxy-p-methoxycinnamate, N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline, neopentyl tetra(α-cyano-β,β-diphenylacrylate).
[0115] 2.3. Nickel compounds, such as nickel complexes of 2,2'-thio-bis[4-(1,1,3,3-tetramethylbutyl)phenol], e.g. 1:1 or 1:2 complexes (with or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine), nickel dibutyldithiocarbamate, nickel salts of monoalkyl esters of 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid, e.g. the methyl or ethyl ester, nickel complexes of ketoximes, e.g. nickel complexes of 2-hydroxy-4-methylphenylundecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole (with or without additional ligands).
[0116] 2.4. Oxamides, such as 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and mixtures thereof with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.
[0117] 2.5. 2-(2-hydroxyphenyl)-1,3,5-triazines, such as 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, Azine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[4-(dodecyloxy / tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy bis(4-(3-butoxy-2-hydroxypropoxy)phenyl)-1,3,5-triazine, 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(4-[2-ethylhexyloxy]-2-hydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazine.
[0118] 3. Metal deactivators, such as N,N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N,N'-diacetyladipoyl dihydrazide, N,N'-bis(salicyloyl)oxalyl dihydrazide, N,N'-bis(salicyloyl)thiopropionyl dihydrazide.
[0119] 4. Phosphites and phosphonates, for example, triphenyl phosphite, diphenyl alkyl phosphite, dialkyl phenyl phosphite, tris(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythrityl diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythrityl diphosphite, bis(2,4-di-tert-butylphenyl) pentaerythrityl diphosphite, bis(2,4-di-cumylphenyl) pentaerythrityl diphosphite, Lithyl, Diphosphite bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythrityl, Diphosphite diisodecyloxypentaerythrityl, Diphosphite bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythrityl, Diphosphite bis(2,4,6-tris(tert-butylphenyl)pentaerythrityl, Tristearyl sorbitol triphosphite, 4,4'-biphenylenediphosphonic acid tetrakis(2,4-di-tert-butylphenyl), 6-isooctyloxy-2,4,8,10- Tetra-tert-butyl-12H-dibenzo[d,g]-1,3,2-dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g]-1,3,2-dioxaphosphocin, 2,2',2''-nitrilo[triethyltris(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl] 2-Ethylhexyl phosphite (3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl), 5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,3,2-dioxaphosphiran, mixture of 2,4-bis(1,1-dimethylpropyl)phenyl and 4-(1,1-dimethylpropyl)phenyl triesters of phosphorous acid (CAS:939402-02-5), triphenyl phosphite, α-hydro-ω-hydroxypoly[oxy(methyl-1,2-ethanediyl)]C10-16 alkyl ester polymer (CAS: 1227937-46-3), triphenyl phosphite, 1,4-cyclohexanedimethanol, propylene glycol C10-16 alkyl ester polymer (CAS Reg. No. 1821217-71-3).
[0120] The following phosphites are particularly preferred: Tris(2,4-di-tert-butylphenyl) phosphite (Irgafos® 168, Ciba Specialty Chemicals Inc.), tris(nonylphenyl) phosphite, [ka]
[0121] 5. Hydroxylamines, such as N,N-dibenzylhydroxylamine, N,N-diethylhydroxylamine, N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-ditetradecylhydroxylamine, N,N-dihexadecylhydroxylamine, N,N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamines derived from hydrogenated tallow amine.
[0122] 6. Nitrones, such as N-benzyl-α-phenyl nitrone, N-ethyl-α-methyl nitrone, N-octyl-α-heptyl nitrone, N-lauryl-α-undecyl nitrone, N-tetradecyl-α-tridecyl nitrone, N-hexadecyl-α-pentadecyl nitrone, N-octadecyl-α-heptadecyl nitrone, N-hexadecyl-α-heptadecyl nitrone, N-octadecyl-α-pentadecyl nitrone, N-heptadecyl-α-heptadecyl nitrone, N-octadecyl-α-hexadecyl nitrone, nitrones derived from N,N-dialkylhydroxylamines derived from hydrogenated tallow amine.
[0123] 7. Thiosynergists, for example dilauryl thiodipropionate, dimistryl thiodipropionate, pentaerythritol tetrakis[3-(dodecylthio)propionate], distearyl thiodipropionate or distearyl disulfide.
[0124] 8. Peroxide scavengers, for example, esters of β-thiodipropionic acid, such as the lauryl, stearyl, myristyl or tridecyl ester, zinc salts of mercaptobenzimidazole or 2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol tetrakis(β-dodecylmecapto)propionate.
[0125] 9. Polyamide stabilizers, such as copper salts in combination with iodides and / or phosphorus compounds and salts of divalent manganese.
[0126] 10. Basic co-stabilizers, for example, melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example, calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate or zinc pyrocatecholate.
[0127] 11. Nucleating agents, for example inorganic substances such as talcum, metal oxides, for example titanium dioxide or magnesium oxide, preferably alkaline earth metal phosphates, carboxylates or sulfates; organic compounds, for example mono- or polycarboxylic acids and their salts, for example 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds, for example ionic copolymers (ionomers). Particularly preferred are 1,3:2,4-bis(3',4'-dimethylbenzylidene)sorbitol, 1,3:2,4-di(para-methyldibenzylidene)sorbitol and 1,3:2,4-di(benzylidene)sorbitol.
[0128] 12. Fillers and reinforcing agents, such as calcium carbonate, silicates, surface treated silicas (e.g., those described in US Patent Application Publication Nos. 2007 / 60,697A and 2009 / 111,918A), glass fibers, glass beads, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and other natural product fine powders or fibers, synthetic fibers.
[0129] 13. Other additives, such as plasticizers, lubricants, emulsifiers, pigments, rheological additives, catalysts, flow control agents, optical brighteners, flame retardants, antistatic agents and foaming agents.
[0130] 14. Benzofuranones and indolinones, for example U.S. Pat. No. 4,325,863; U.S. Pat. No. 4,338,244; U.S. Pat. No. 5,175,312; U.S. Pat. No. 5,216,052; U.S. Pat. No. 5,252,643; German Patent Application Publication No. A-4316611; German Patent Application Publication No. A-4316622; German Patent Application Publication No. A-4316631; EP-A-0589839, EP-A-0591102, EP-A-1291384 or 3-[4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran-2-one, 5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]- )phenyl]benzofuran-2-one, 3,3'-bis[5,7-di-tert-butyl-3-(4-[2-hydroxyethoxy]phenyl)benzofuran-2-one], 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one, 3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(3,4-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(2,3-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(2-acetyl-5-isooctylphenyl)-5-isooctylbenzofuran-2-one.
[0131] In another aspect, the claimed invention provides: I. at least one compound of formula (A) as defined above, II. at least one UV absorber as defined above; The present invention relates to an additive mixture comprising:
[0132] In one embodiment, the weight ratio of the at least one compound of Formula (A) to the at least one UV absorber ranges from 1:50 to 50:1.
[0133] In yet another aspect, the claimed invention relates to the use of the additive mixture defined above for improving the stability of stabilized organic materials exposed to light.
[0134] The materials stabilized according to the invention can be used in various forms, for example as films, fibers, tapes, moulding compositions, profiles or as binders for paints, adhesives or putties.
[0135] More particularly, the organic materials stabilized according to the present invention can be used to fabricate the following devices:
[0136] I-1) Automotive applications, especially bumpers, dashboards, batteries, rear and front linings, molded under hood parts, hat shelves, trunk linings, interior linings, airbag covers, molded electronic parts for fittings (lights), panels for dashboards, headlight lenses, instrument panels, exterior linings, upholstery, auto lights, headlights, parking lights, tail lights, stop lights, interior and exterior trim; door panels; gas tanks; glazing front side; rear windows; seat backings, exterior panels, wire insulation, sealing profile extrusions, cladding, pillar covers, chassis parts, exhaust systems, fuel filters / fillers, fuel pumps, fuel tanks, side door moldings, convertible tops, side mirrors, exterior trim, fasteners / fixtures, front end modules, glass, hinges, locking systems, luggage / roof racks, pressed / stamped parts, seals, side impact protection, sound deadening / insulation and sunroofs.
[0137] I-2) Devices for airplanes, trains, and automobiles (cars, motorcycles), including furniture.
[0138] I-3) Devices for space applications, in particular rockets and satellites, e.g. re-entry shields.
[0139] I-4) Devices for architecture and design, mining applications, soundproofing systems, street shelters and shelters.
[0140] II-1) Household appliance applications, in particular washing machines, tumble dryers, ovens (microwave ovens), dishwashers, mixers and irons.
[0141] II-2) Capacitor foil, refrigerators, heaters, air conditioners, sealing of electronic devices, semiconductors, coffee makers and vacuum cleaners.
[0142] III-1) Technical parts such as cogwheels (gears), slide fittings, spacers, screws, bolts, handles, knobs, etc.
[0143] III-2) Rotating blades, ventilators and windmill blades, solar panels, swimming pools, swimming pool covers, pool tarpaulins, pond tarpaulins, closets, wardrobes, partition walls, slat walls, folding walls, roofs, shutters (e.g. roller shutters), fittings, connections between pipes, sleeves and conveyor belts.
[0144] III-3) Profiles (window glass) and siding of all shapes.
[0145] III-4) Glass substitutes, in particular extruded plates, building, aircraft, school glazing (single, double or multi-wall), extruded sheets, architectural glass, trains, transport, sanitary and greenhouse window films.
[0146] III-5) Plates (walls, cutting boards), extrusion coatings (photographic paper, Tetra Pak® and pipe coatings), silos, wood substitutes, plastic lumber, wood composites, walls, surfacing, furniture, decorative foils, flooring (interior and exterior), flooring, duckboard and tiles.
[0147] III-6) Cement, concrete, composite applications and coverings, exterior siding and cladding, hand rails, balustrades, kitchen counters, roofing, roofing sheets, tiles and tarpaulins.
[0148] IV-1) Plates (walls and cutting boards), trays, artificial turf, astroturf, roofs for athletic stadiums (athletics), artificial flooring and tapes for athletic stadiums (athletics).
[0149] V-1) General plastic films (packaging, dump, laminates, swimming pool covers, trash bags, wallpaper, stretch and shrink film, raffia, desalination film, batteries and connectors).
[0150] V-2) Agricultural films (greenhouse covers, tunnels, mulches, silage wraps, bale wraps) (especially where there is intensive application of pesticides).
[0151] VI-1) Food packaging and wrapping (flexible and solid), BOPP, BOPET, bottles.
[0152] VI-2) Cartridges, syringes, medical applications, any transport container, waste paper baskets and bins, garbage bags, bins, dust bins, trash bin liner, wheeled bins, containers in general, tanks for water / used water / chemical reactions / gas / oil / petrol / diesel; tank liners, boxes, crates, battery cases, troughs, pistons and other medical instruments, ophthalmic applications, diagnostic equipment and pharmaceutical blister packaging.
[0153] VII-1) Fillers (talc, chalk, kaolin, wollastonite, pigments, carbon black, TiO 2 , mica, nanocomposites, dolomite, silica, silicates, glass, asbestos) filled polymeric devices.
[0154] Therefore, another aspect of the present invention is an article made from the composition defined above.
[0155] The claimed invention provides one or more of the following advantages: 1. Creating an article using a combination of UV absorbers and / or HALS with a compound of formula (A) and a stabilized organic material improves the durability of the final article when exposed to light. 2. The article is more resistant to light exposure, thereby extending the life of the final article. 3. Economic value is gained by extending the life of the final product.
[0156] Specific embodiments of the present invention will be described below. 1. i. a stabilized organic material; ii. At least one compound of formula (A): [ka] (In the formula, E 1 is hydrogen, C 1 ~C 18 Alkyl, formula P: [ka] (Wherein R, R' and R'' are each independently C 1 ~C 18 is alkylene, and b is an integer ranging from 1 to 3; Formula Q: [ka] (Wherein, T and U are each independently a linear or branched C 1 ~C 18 alkyl), E 2 , E 3 , E 4 , E 5 and E 6 are independently hydrogen, C 1~C 18 Alkyl, phenyl or 1, 2 or 3 C 1 ~C 4 Alkyl-substituted phenyl or a compound of formula Q: [ka] (Wherein, T and U are each independently a linear or branched C 1 ~C 18 with a compound of formula (I) (I) (I); iii. at least one UV absorber; The present invention relates to a composition comprising:
[0157] 2. The composition of embodiment 1, wherein the stabilized organic material is selected from the group consisting of polyethylene, polypropylene, polyurethane, styrenic polymers, polyvinyl chloride, and mixtures thereof.
[0158] 3. The composition of embodiment 1 or 2, wherein the stabilized organic material is polyvinyl chloride.
[0159] 4. The composition according to one or more of the preceding embodiments, wherein the polyvinyl chloride is rigid, semi-rigid or flexible polyvinyl chloride.
[0160] 5. The composition according to one or more of the preceding embodiments, wherein the stabilized organic material comprises at least one plasticizer, at least one thermal stabilizer, and mixtures thereof.
[0161] 6. The at least one plasticizer is selected from the group consisting of phthalates, dialkyl cyclohexane-1,2-dicarboxylates, dialkyl cyclohexane-1,3-dicarboxylates, dialkyl cyclohexane-1,4-dicarboxylates, dialkyl terephthalates, esters of trimellitic acid, trialkyl trimellitates, alkyl benzoates, dibenzoates of glycols, pentaerythritol esters, hydroxybenzoates, monoesters, esters of saturated monocarboxylic acids, esters of unsaturated monocarboxylic acids, esters of saturated dicarboxylic acids, esters of unsaturated dicarboxylic acids, amides and esters of aromatic sulfonic acids, The composition according to embodiment 5, wherein the carboxylic acid ester is selected from the group consisting of alkylsulfonate esters, glycerol esters, glycon esters, isosorbide esters, phosphate esters, citrate triesters, acylated trialkyl citrates, alkylpyrrolidone derivatives, 2,5-dialkyl furan dicarboxylates, 2,5-dialkyl tetrahydrofuran dicarboxylates, epoxy plasticizers, epoxidized vegetable oils and epoxidized fatty acid monoalkyl esters, chlorinated hydrocarbons, polymeric plasticizers, polyesters formed from aliphatic and / or aromatic polycarboxylic acids and at least dihydric alcohols, and mixtures thereof.
[0162] 7. Phthalate esters are dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, di-2-ethylhexyl phthalate, di-n-octyl phthalate, disooctyl phthalate, diisononyl phthalate, diisononyl hexahydrophthalate, diisodecyl phthalate, diisotridecyl phthalate, dicyclohexyl phthalate, dimethylcyclohexyl phthalate, dimethyl glycol phthalate, dibutyl glycol phthalate, benzyl butyl phthalate and diphenyl phthalate, as well as mixtures of phthalates, e.g. phthalate C produced mainly from linear alcohols. 7 ~C 9 - and C 9 ~C 11 Alkyl ester, phthalic acid C 6 ~C 10 -n-Alkyl esters and phthalic acids C 8 ~C 10The composition of embodiment 6, wherein the aryl ester is selected from the group consisting of -n-alkyl esters.
[0163] 8. The composition of embodiment 6, wherein the epoxy plasticizer is selected from the group consisting of epoxidized soybean oil, epoxidized linseed oil, and octyl oleate.
[0164] 9. The composition of embodiment 5, wherein the at least one heat stabilizer is selected from the group consisting of metal salts of fatty acids, complex metal stabilizers, organotin stabilizers, lead stabilizers, organic stabilizers, and mixtures thereof.
[0165] 10. Metal salts of fatty acids are fatty saturated C 2 ~C 22 Carboxylate, Aliphatic Olefinic C 3 ~C 22 Carboxylate, aliphatic C substituted with at least one OH group 2 ~C 22 Carboxylic acid salts, cyclic or bicyclic C 5 ~C 22 Carboxylate, aromatic C 7 ~C 22 Carboxylate, aromatic C substituted with at least one OH group 7 ~C 22 Carboxylate, C 1 ~C 16 Alkyl-substituted phenyl carboxylates and phenyl-C 1 ~C 16 The composition of embodiment 9, wherein the alkyl carboxylate is selected from the group consisting of calcium, zinc, magnesium or aluminum salts of the set of alkyl carboxylates.
[0166] 11. The composition of embodiment 9 or 10, wherein the metal salt of a fatty acid is selected from the group consisting of calcium stearate, zinc octanoate, zinc oleate, zinc stearate and zinc laurate.
[0167] 12. The composition of embodiment 9, wherein the complex metal stabilizer is a barium / zinc-based or calcium / zinc-based stabilizer.
[0168] 13. The composition of embodiment 9, wherein the organotin stabilizer is selected from the group consisting of organotin mercaptoesters, organotin carboxylates, and organotin sulfides.
[0169] 14. The composition of embodiment 9, wherein the lead stabilizer is selected from the group consisting of tribasic lead sulfate, dibasic lead sulfate, dibasic lead phthalate, dibasic lead phosphate, and lead stearate.
[0170] 15.E 1 is hydrogen, C 1 ~C 8 alkyl, a group of formula P or a group of formula Q, 2 , E 3 , E 4 , E 5 and E 6 are independently hydrogen, C 1 ~C 4 The composition of embodiment 1, wherein R is an alkyl, phenyl or a group of formula Q.
[0171] 16. Compositions according to one or more of the preceding embodiments 1 or 15, wherein at least one compound of formula (A) is selected from the formulae (A-1), (A-2), (A-3) and (A-4): [ka] [ka] .
[0172] 17. The composition of embodiment 1, wherein the UV absorber is selected from the group consisting of 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyphenyl)-1,3,5-triazines, esters of substituted and unsubstituted benzoic acid, cyanoacrylates, oxanilides, benzoxazinones, and mixtures thereof.
[0173] 18. 2-(2'-Hydroxyphenyl)benzotriazole is 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3' -tert-butyl-2'-hydroxy-5'-methylphenyl)-5-chloro-benzotriazole, 2-(3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)benzotriazole, 2-(3',5'-bis-(α,α-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy -5'-(2-octyloxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)-carbonylethyl]-2'-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3' -tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)benzotriazole, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenylbenzotriazole, 2,2'-methylene-bis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenol];2-[3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole transesterification product with polyethylene glycol 300;, [ka] 18. The composition of embodiment 17, wherein R=3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl, 2-[2'-hydroxy-3'-(α,α-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]-benzotriazole; 2-[2'-hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5'-(α,α-dimethylbenzyl)-phenyl]benzotriazole, and mixtures thereof.
[0174] 19. The composition according to any one of embodiments 17 to 18, wherein the 2-(2'-hydroxyphenyl)benzotriazole is selected from 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)-5-chloro-benzotriazole, and mixtures thereof.
[0175] 20. The composition of embodiment 17, wherein the 2-hydroxybenzophenone is selected from the group consisting of 2-hydroxy-4-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octyloxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4,2',4'-trihydroxybenzophenone, 2-hydroxy-2'-hydroxy-4,4'-dimethoxybenzophenone derivatives, and mixtures thereof.
[0176] 21. The composition of embodiment 17 or 20, wherein the 2-hydroxybenzophenone is 2-hydroxy-4-octyloxybenzophenone.
[0177] 22. 2-(2-hydroxyphenyl)-1,3,5-triazine is 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3, 5-triazine, 2-[4-(dodecyloxy / tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(4-[2-ethylhexyloxy]-2-hydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2-(4,6-bis-(2,4-dimethylphenyl)-1,The composition of embodiment 17, wherein the phenol is selected from the group consisting of 3,5-triazin-2-yl)-5-(octyloxy)-phenol, bis{2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy]ethyl} dodecanedioate, and mixtures thereof.
[0178] 23. The composition of embodiment 17, wherein the esters of substituted and unsubstituted benzoic acid are selected from the group consisting of 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, and mixtures thereof.
[0179] 24. The composition of embodiment 17 or 23, wherein the ester of substituted and unsubstituted benzoic acid is 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.
[0180] 25. The composition of embodiment 17, wherein the cyanoacrylate is selected from the group consisting of ethyl α-cyano-β,β-diphenylacrylate, isooctyl α-cyano-β,β-diphenylacrylate, neopentyl tetra(α-cyano-β,β-diphenylacrylate, pentaerythritol tetrakis(2-cyano-3,3-diphenylacrylate), ethyl 2-cyano-3,3-diphenylacrylate, (2-ethylhexyl) 2-cyano-3,3-diphenylacrylate, and mixtures thereof.
[0181] 26. The composition of embodiment 17, wherein the oxanilide is selected from the group consisting of 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butyloxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butyloxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethyloxanilide and mixtures thereof with 2-ethoxy-2'-ethyl-5,4'-di-tert-butyloxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides and mixtures thereof.
[0182] 27. The composition of embodiment 17 or 26, wherein the oxanilide is 2-ethoxy-2'-ethyloxanilide.
[0183] 28. The composition of embodiment 17, wherein the benzoxazinone is 2,2'-(1,4-phenylene)bis[4H-3,1-benzoxazin-4-one].
[0184] 29. At least one compound of formula (B) of general formula (I), general formula (II), general formula (III) and general formula (IV): - a compound (B) of general formula (I): [ka] (In the formula, A 1 is a linear or branched, substituted or unsubstituted C 2 ~C 18 Alkylene, substituted or unsubstituted C 5 ~C 7 Cycloalkylene and C 1 ~C 4 Alkylene Diene (C 5 ~C 7 cycloalkylene; A 2 is H, linear or branched, substituted or unsubstituted C 1 ~C12 Alkyl, C 1 ~C 12 Alkyloxy, substituted or unsubstituted C 5 ~C 12 Cycloalkyl and C 5 ~C 12 cycloalkyloxy; A 3 and A 4 is H, linear or branched, substituted or unsubstituted C 1 ~C 12 Alkyl, substituted or unsubstituted C 5 ~C 12 Cycloalkyl and formula (a-1): [ka] or A 3 and A 4 together with the nitrogen atom to which they are attached form a 5- to 10-membered heterocyclic ring; a is an integer ranging from 1 to 20, and the repeating units are the same or different; - a compound (B) of general formula (II): [ka] (In the formula, x 1 and x 2 is C 1 ~C 30 independently selected from alkoxy; - a compound (B) of general formula (III): [ka] (In the formula, Y 1 is a linear or branched, substituted or unsubstituted C 3 ~C 20 is alkyl, Y2 is C 1 ~C 30 alkyl); and - a compound (B) of general formula (IV): [ka] (In the formula, Y 1 is a linear or branched, substituted or unsubstituted C 3 ~C 20 is alkyl, Y 3 is a linear or branched, substituted or unsubstituted C 3 ~C 20 Alkyl and C 3 ~C 20 independently selected from alkylidene; X is C 2 ~C 5 is alkyl, The composition of one or more of the preceding embodiments, further comprising: n is an integer ranging from 1 to 8.
[0185] 30. The compound of formula (B) has the formula (B-1), (B-2), (B-3), (B-4), (B-5), (B-6), (B-7) or (B-8): [ka] (wherein a is an integer ranging from 1 to 10), and [ka] [ka] [ka] (wherein n is 2).
[0186] 31. The composition according to one or more of the preceding embodiments, further comprising at least one sterically hindered amine light stabilizer.
[0187] 32. The at least one sterically hindered amine light stabilizer is selected from the group consisting of bis(1-undecyloxy-2,2,6,6-tetramethyl-4-piperidyl)carbonate, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetra ...n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, bis(1,2,2,6,6-tetramethyl-4-piperidyl)sebacate, and bis(1,2,2,6,6-tetramethyl-4-piperidyl)sebacate. 1,2,2,6,6-pentamethyl-4-piperidyl), 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid condensation product, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine linear or cyclic condensation product, tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate, 1,2,3,4-butanetetracarboxylic acid tetrakis(2,2,6,6-tetramethyl 1,1'-(1,2-ethanediyl)-bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, 2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate bis(1,2,2,6,6-pentamethylpiperidyl), 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, bis(1-octyl)sebacate 1-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, linear or cyclic condensation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine with 4-morpholino-2,6-dichloro-1,3,5-triazine, condensation products of 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5-triazine with 1,2-bis(3-aminopropylamino)ethane, 2-chloro-4,Condensation product of 6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine with 1,2-bis(3-aminopropylamino)ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione, 3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione, 4-hexa Mixtures of decyloxy-2,2,6,6-tetramethylpiperidine and 4-stearyloxy-2,2,6,6-tetramethylpiperidine; condensation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine; condensation products of 1,2-bis(3-aminopropylamino)ethane, 2,4,6-trichloro-1,3,5-triazine and 4-butylamino-2,2,6,6-tetramethylpiperidine; 1,6-hexanediamine and and 2,4,6-trichloro-1,3,5-triazine and condensation products of N,N-dibutylamine and 4-butylamino-2,2,6,6-tetramethylpiperidine;N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimide, N-(1,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylsuccinimide, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4,5]decane, 7,7,9,9-tetramethyl-2-cycloundecyl-1- Reaction products of oxa-3,8-diaza-4-oxospiro-[4,5]decane with epichlorohydrin, 1,1-bis(1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl)-2-(4-methoxyphenyl)ethene, N,N'-bis-formyl-N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine, diester of 4-methoxymethylenemalonic acid with 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, poly[methylpropyl-3-oxy-4-(2,2,6,6-tetramethyl-4-piperidyl)]siloxane, reaction products of maleic anhydride-α-olefin copolymer with 2,2,6,6-tetramethyl-4-aminopiperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-butylamino]-6-(2-hydroxyethyl)amino-1,3,5-triazine, 1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidin-4-yl 5-(2-ethylhexanoyl)oxymethyl-3,3,5-trimethyl-2-morpholinone, 5-(2-ethylhexanoyl)oxymethyl-3,3,5-trimethyl-2-morpholinone, reaction products of 2,4-bis[(1-cyclohexyloxy-2,2,6,6-piperidin-4-yl)butylamino]-6-chloro-s-triazine with N,N'-bis(3-aminopropyl)ethylenediamine, 1,3,5-tris(N-cyclohexyl-N-(2,2,6,6-tetramethylpiperazin-3-one-4-yl)amino)-s-triazine Azine, 1,3,5-tris(N-cyclohexyl-N-(1,2,2,6,6-pentamethylpiperazin-3-one-4-yl)amino)-s-triazine, 4-N-butyl-2-N,4-N-bis(2,2,6,6-tetramethylpiperidin-4-yl)-2-N-[6-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]hexyl]-1,3,5-triazine-2,4-diamine, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-N,N'-diformylhexamethylenediamine, 1,5,8,12-tetrakis [4,6-bis(n-butyl-n-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane, N,N'"-[1,2-ethane-diyl-bis[[[4,6-bis-[butyl(1,2,2,6,6-pentamethyl-4-piperidinyl)amino]-1,3,5-triazin-2-yl]imino]-3,1-propanediyl]]bis[N',N"-dibutyl-N',N"-bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-1,3,5-triazine-2,4,32. The composition according to embodiment 31, wherein the amine is selected from the group consisting of N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,6-hexanediamine polymerized with morpholine-2,4,6-trichloro-1,3,5-triazine, poly(4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol-alt-1,4-butanedioic acid) and mixtures thereof.
[0188] 33. The composition according to one or more of the preceding embodiments, further comprising at least one additive selected from slip agents, antiblocking agents, thermal fillers, pigments, antifogging agents, and anti-misting agents.
[0189] 34. The composition of embodiment 1, wherein the weight ratio of the stabilized organic material to the total weight of the at least one compound of Formula (A) and the at least one UV absorber is in the range of 99.9:0.1 to 99:1.
[0190] 35. The composition of embodiment 1, wherein the weight ratio of the at least one compound of formula (A) to the at least one UV absorber is in the range of 1:50 to 50:1.
[0191] 36. I. at least one compound of formula (A) as described in embodiments 1, 15 and 16; II. at least one UV absorber as described in embodiments 1, 17-28; 23. The additive mixture comprising:
[0192] 37. The additive mixture of embodiment 36, wherein the weight ratio of the at least one compound of Formula (A) to the at least one UV absorber is in the range of 1:50 to 50:1.
[0193] 38. An article comprising the composition according to one or more of embodiments 1-35.
[0194] 39. Use of an additive mixture according to one or more of embodiments 36 to 38 for improving the stability of a stabilized organic material exposed to light.
[0195] The invention is illustrated in more detail by the following examples, in which all percentages and parts are by weight unless otherwise stated. EXAMPLES
[0196] Stabilizers as listed in Table 1 below: Compound (A-1): [ka] Compound (A-2): [ka] Compound (A-3): [ka] 2-Hydroxybenzophenone UV absorber (H-UV): 2-Hydroxy-4-octyloxybenzophenone 2-(2'-hydroxyphenyl)benzotriazole (P-UV): 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole Compound (B-3): [ka] Cyanoacrylate UV absorber (C-UV): Pentaerythritol tetrakis(2-cyano-3,3-diphenylacrylate) Compound (B-4): [ka]
[0197] Example A: Stabilization of flexible polyvinyl chloride (f-PVC): A basic mixture was prepared of 64.73 phr of PVC (Norvinyl® S7060 from Ineos), 32.36 phr of diisononyl phthalate plasticizer (Palatinol® N from BASF), 1.61 phr of epoxidized soybean oil (Drapex® 39 from Galata Chem.) and 1.30 phr of heat stabilizer (Baerostab® CT 9063 X RF from Baerlocher; a liquid CaZn stabilizer) (phr means parts per hundred parts of rubber).
[0198] 40 g of this PVC blend was mixed with the UV absorber mixture and / or hindered amine light stabilizer (HALS) listed in Table 1 in a glass beaker, and then the resulting compound 2 was calendered on a two-roll mill with a gap of 0.4 mm, f=1:1.2, at 160° C. for 8 minutes. All the formulations used in the tests are shown in Table 1.
[0199] The resulting sheet was then exposed to xenon light according to Cycle 1 of ISO 4892-2 (xenon light, 2 borosilicate filters "S", 0.51 W / m2 (340 nm), black standard temperature (BST) 65°C + / - 2°C, dry bulb temperature (DBT) 38°C + / - 3°C, relative humidity (RH) 50 + / - 5%, continuous irradiation, 102 minutes no water spray followed by 18 minutes water spray).
[0200] The mechanical properties were measured by cutting according to ISO 527, 5A, and the results are shown in Table 2.
[0201] The colour was measured according to DIN 6167 (1980-01) and the results are shown in Table 3.
[0202] After exposure to cycle 1 of ISO 4892-2, the specimens were photographed and evaluated for appearance using a Canon EOS 5DSR camera and four light sources led Floodlight 24100 100W IP65, 4000K from ADEO Services. A rating of 1 to 5 was given to specimen A, with rating 1 being the worst and indicating a higher degree of dichlorination of the PVC specimen, and rating 5 indicating no dichlorination had occurred. The results are shown in Tables 4a and 4b.
[0203] Table 4a also shows the condition of the specimens exposed for 4000 hours to cycle 1 of ISO 4892-2. B means that the specimen has broken, / means that the specimen is still in good shape.
[0204] [Table 1]
[0205] JPEG2024528642000050.jpg212170
[0206] JPEG2024528642000051.jpg130170
[0207] [Table 2]
[0208] JPEG2024528642000053.jpg202170
[0209] [Table 3]
[0210] [Table 4a]
[0211] JPEG2024528642000056.jpg243170
[0212] [Table 4b]
[0213] Example B: Stabilization of rigid polyvinyl chloride (r-PVC): Ingredients listed in Tables 5-8 below: PVC: Suspension PVC with a K value of 70; Calcium carbonate (CaCO 3 ): Commercial grade, calcium carbonate 98%, average particle size 2 microns, d98:8 microns; Epoxidized soybean oil (ESBO): Viscosity at 25°C: 320 cps [Drapex 39]; Heat stabilizer: Calcium / Zinc (Ca / Zn), Nonylphenol, Ethyl Hexanoate and pt-Butyl Benzoate free [Baerostab CT 9063 X RF]; Titanium dioxide (TiO 2 ): rutile type, produced by the chlorine process, surface treatment (with aluminum, silicone and polysiloxane compounds); Impact modifier: acrylic acid-butyl acrylate-2-ethylhexyl acrylate-methyl methacrylate polymer; HALS1: N,N'"-[1,2-ethane-diyl-bis[[[4,6-bis-[butyl(1,2,2,6,6-pentamethyl-4-piperidinyl)amino]-1,3,5-triazin-2-yl]imino]-3,1-propanediyl]]bis[N',N"-dibutyl-N',N"-bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-1,3,5-triazine-2,4,6-triamine; HALS2: poly(4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol-alt-1,4-butanedioic acid); Compound (B-4): [ka] UV absorber 1: 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methylphenol; Compound (A-1): [ka] Compound (A-2): [ka]
[0214] process The process consisted of premixing the raw materials in a tumbler mixer, followed by calendering at 160°C for 6 minutes on a two-roll mill at a rotation speed of 29 rpm, a friction rate of 1:1.2 and a roll gap of 0.5 mm. The compound obtained was pressed into plates of 1 mm thickness (165°C, 100 bar for 1 minute, followed by cooling at 100 bar for 1 minute).
[0215] Accelerated weathering test: Plates were subjected to cycle 1 of EN ISO 4892-2 (102 minutes of irradiation + 18 minutes of irradiation + water spray cycle, irradiance of xenon light at 300-400 nm 60 W / m 2 The samples were subjected to accelerated UV exposure according to the black standard temperature of 65° C., dry bulb temperature of 38° C., and relative humidity of 50%). Collections were made at various time points as shown in hours in Tables 5-8 below.
[0216] Measurement at scheduled collection times: Colour coordinate b* in CIELAB units according to ISO 4582; negative values indicate blue colours, positive values indicate yellow colours.
[0217] Yellowness (unitless) according to ASTM E313; Delta E* in CIELAB units: Take the square root of the difference between the CIELAB color coordinates L*, a*, and b* at the time of recovery minus the initial CIELAB color coordinates L*, a*, and b* as defined in ISO 11664-4.
[0218] The color properties are shown in Tables 5 to 7.
[0219] The roughness in microns is the arithmetic mean of the absolute deviations in the height direction of the profile curve from the mean line as defined in EN ISO 4288.
[0220] The results are shown in Table 8.
[0221] [Table 5]
[0222] From the above results it can be seen that the yellow coordinate b* of the r-PVC stabilized by the inventive examples comprising one compound of formula (A) and at least one UV absorber was significantly lower.
[0223] [Table 6]
[0224] From the above results it can be seen that the yellowness index values of the r-PVC stabilized with the inventive examples comprising one compound of formula (A) and at least one UV absorber were significantly lower.
[0225] [Table 7]
[0226] From the above results it can be seen that the r-PVC stabilized according to inventive example 3 comprising one compound of formula (A) and at least one UV absorber had significantly lower discoloration values, defined as delta E*.
[0227] [Table 8]
[0228] From the above results, it can be seen that the surface roughness value of the r-PVC stabilized according to inventive example 3, which contains one compound of formula (A) and at least one UV absorber, was significantly lower.
Claims
1. i. A stabilized organic material; and ii. At least one compound of formula (A): 【Chemical 1】 (wherein E 1 is hydrogen, C 1 -C 18 alkyl, formula P: [Chemical Formula 2] (wherein R, R' and R'' are each independently C 1 ~C 18 alkylene, and b is an integer in the range of 1 to 3), or Formula Q: [Chemical Formula 3] (wherein T and U are each independently a linear or branched C 1 -C 18 alkyl) group, E 2 、E 3 、E 4 、E 5 and E 6 are, independently of one another, hydrogen, C 1 -C 18 alkyl, phenyl or phenyl substituted with 1, 2 or 3 C 1 -C 4 alkyl or formula Q: 【Chemical Formula 4】 (wherein, T and U are each independently a linear or branched C 1 -C 18 alkyl) group); and a compound of iii. At least one UV absorber; and A composition comprising the same.
2. The composition according to claim 1, wherein the stabilized organic material is selected from the group consisting of polyethylene, polypropylene, polyurethane, styrene polymers, polyvinyl chloride and mixtures thereof.
3. The composition according to claim 1, wherein the stabilized organic material is polyvinyl chloride.
4. The composition according to claim 1, wherein the polyvinyl chloride is rigid, semi-rigid or flexible polyvinyl chloride.
5. The composition according to claim 1, wherein the stabilized organic material comprises at least one plasticizer, at least one heat stabilizer and mixtures thereof.
6. The at least one plasticizer is selected from the group consisting of phthalic acid esters, dialkyl cyclohexane-1,2-dicarboxylates, dialkyl cyclohexane-1,3-dicarboxylates, dialkyl cyclohexane-1,4-dicarboxylates, dialkyl terephthalates, esters of trimellitic acid, trialkyl trimellitates, alkyl benzoates, dibenzoates of glycols, pentaerythritol esters, hydroxybenzoic acid esters, monoesters, esters of saturated monocarboxylic acids, esters of unsaturated monocarboxylic acids, esters of saturated dicarboxylic acids, esters of unsaturated dicarboxylic acids, amides and esters of aromatic sulfonic acids, alkyl sulfonic acid esters, glycerol esters, glycon esters, isosorbide esters, phosphate esters, triester of citric acid, trialkyl acylated citrate, alkyl pyrrolidone derivatives, dialkyl 2,5-furandicarboxylates, dialkyl 2,5-tetrahydrofurandicarboxylates, epoxy plasticizers, epoxidized vegetable oils and epoxidized fatty acid monoalkyl esters, chlorinated hydrocarbons, polymeric plasticizers, polyesters formed from aliphatic and / or aromatic polycarboxylic acids and at least divalent alcohols and mixtures thereof. The composition according to claim 5.
7. The at least one heat stabilizer is selected from the group consisting of metal salts of fatty acids, composite metal stabilizers, organotin stabilizers, lead stabilizers, organic stabilizers and mixtures thereof. The composition according to claim 5.
8. E 1 is hydrogen, C 1 to C 8 alkyl, a group of formula P (where b is an integer in the range of 1 to 2) or a group of formula Q, and E 2 , E 3 , E 4 , E 5 and E 6 are, independently of one another, hydrogen, C 1 to C 4 alkyl, phenyl or a group of formula Q, the composition according to claim 1.
9. The at least one compound of formula (A) is selected from formulae (A-1), (A-2), (A-3), (A-4) and (A-5): 【Chemical Formula 5】 【Chemical Formula 6】 The composition according to claim 1, selected from
10. The composition according to claim 1, wherein the UV absorber is selected from the group consisting of 2-(2'-hydroxyphenyl)benzotriazole, 2-hydroxybenzophenone, 2-(2-hydroxyphenyl)-1,3,5-triazine, esters of substituted and unsubstituted benzoic acids, cyanoacrylate, oxanilide, benzoxazinone and mixtures thereof.
11. The composition according to claim 1, wherein the weight ratio of the stabilized organic material to the total weight of the at least one compound of formula (A) and the at least one UV absorber is in the range of 99.9:0.1 to 99:
1.
12. I. The at least one compound of formula (A) according to claim 1; II. The at least one UV absorber according to claim 1; An additive mixture comprising
13. The composition according to claim 12, wherein the weight ratio of the at least one compound of formula (A) to the at least one UV absorber is in the range of 1:50 to 50:
1.
14. An article comprising the composition according to one or more of claims 1 to 11.
15. Use of the additive mixture according to claim 12 or 13 for improving the stability of the stabilized organic material upon exposure to light.