UV light stabilizers
By combining UV absorbers with polyether polyols generated from the reaction of sugars, polyols, and epoxides, the problem of poor solubility of UV stabilizers in organic solvents is solved, resulting in a stabilizer with better material compatibility and environmental friendliness.
Patent Information
- Application Number
- CN202480021652.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-04-05
- Filing Date
- 2024-03-28
- Publication Date
- 2025-11-11
AI Technical Summary
Existing UV stabilizers have poor solubility in organic solvents, resulting in poor compatibility with plastics and affecting the long-term stability of materials. At the same time, their synthesis is environmentally burdensome.
By combining UV absorbers with polyether polyols generated from the reaction of sugars, polyols, epoxides, and optional fatty acids, UV stabilizers are formed that improve solubility and reduce environmental impact.
It improves the solubility of UV stabilizers in organic solvents, enhances compatibility with plastics, and reduces the environmental burden.
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Figure CN120936656A_ABST
Abstract
Description
Technical Field
[0001] The invention claimed herein relates to ultraviolet (UV) absorbing compounds and methods for their preparation. Background Technology
[0002] Ultraviolet (UV) light absorbers are an important class of organic compounds used to protect and stabilize organic materials such as plastics, polymers, and coatings from damage caused by light, heat, oxygen, or environmental forces. These stabilizers are also widely used in personal care products, fibers, paints, dyes, and more.
[0003] These stabilizers protect materials by converting absorbed ultraviolet light into low-impact heat and energy. Stabilizers are primarily used to reduce photodegradation (e.g., in plastics or polymers) by playing a key role in suppressing the generation of free radicals that lead to plastic degradation. While both UVA and UVB are known to induce material degradation, UVA is considered to contribute more to this degradation due to its greater abundance in sunlight. In this regard, two commonly used classes of UV stabilizers that provide significant protection against both UVA and UVB are substituted benzotriazoles (BTZ) and substituted triazines, such as hydroxyphenyltriazine (HPT).
[0004] There is a wealth of literature on the use of such triazine and benzotriazole-based stabilizers for UV stabilization. For example, WO 2019006750A1 describes the use of reactive benzotriazole based on mono-trimethylolpropane, primarily for stabilizing polyurethanes against UV degradation. More recently, US2017 / 0349730 A1 introduces compositions comprising hydroxyphenyltriazine and hindered amine stabilizers combined with antioxidants and phosphites into molded articles to achieve suitable thermal and UV stability.
[0005] However, several challenges have been identified in this field. For example, the low molecular weight of well-known stabilizers makes them highly incompatible with their use in plastics, leading to a high level of migration of these molecules toward the material boundaries, resulting in poor long-term stability of the material. This is offset in WO 2010130752 A1 by synthesizing a stabilizer moiety with multiple benzotriazole sections. It has also been noted that the compound exhibits improved integration within the polymer matrix, leading to improved stability.
[0006] However, despite the improvements mentioned above, other challenges remain related to this field. For example, typical stabilizer compounds may have poor solubility in common organic solvents such as xylene. This lack of sufficient solubility makes the compounds economically and environmentally unsuitable for industrial applications. Furthermore, the environmental impact associated with compound synthesis is a significant concern in today's world, amidst growing environmental problems. Therefore, there is a high demand for stabilizers that impose a limited burden on the environment.
[0007] Therefore, there is an unmet need for developing UV stabilizer compounds that are environmentally friendly while maintaining important performance parameters such as high solubility, processability, and stability. Summary of the Invention
[0008] Surprisingly, it was found that incorporating UV absorbers into polyether polyols obtained through the reaction of at least one sugar and polyol with epoxides and optionally fatty acids not only improves their long-term stability but also enhances their solubility in organic solvents such as xylene. Furthermore, the incorporation of bio-associated sugars mitigates the environmental impact of UV absorbers.
[0009] Therefore, the first aspect of the invention claimed herein relates to a product or a salt thereof, which is obtainable by a method comprising the following steps:
[0010] a) To prepare at least one compound having formula (I) in the presence of at least one catalyst,
[0011]
[0012] Wherein G* is selected from substituted 2-(2-hydroxyphenyl)-2H-benzotriazole groups or substituted 2-hydroxyphenyl-triazine.
[0013] R 30 Selected from hydrogen, substituted or unsubstituted straight or branched C1-C 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, substituted or unsubstituted C7-C 24 Arylalkyl or -S(=O)2R 31 , where R 31 C1-C selected from substituted or unsubstituted straight or branched chains 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 cycloalkyl, substituted or unsubstituted C6-C 24 aryl, substituted or unsubstituted C7-C 24 Arylalkyl;
[0014] b) Reaction with a polyether polyol, which is obtained by reacting a composition of the following:
[0015] b1) Based on 5 wt% to 90 wt% of the total amount of the polyether polyol, at least one sugar selected from C5-C6 sugar alcohols, monosaccharides, oligosaccharides, polysaccharides or mixtures thereof;
[0016] b2) At least one epoxy alkane, comprising 5 wt% to 90 wt% of the total amount of polyether polyol;
[0017] b3) at least one polyol having 2 to 4 hydroxyl groups, comprising 0 wt% to 90 wt% of the total amount of the polyether polyol; and
[0018] b4) Based on a total amount of 0 wt% to 15 wt% of at least one optional reactant selected from fatty acids, fatty acid monoesters or mixtures thereof.
[0019] The second aspect of the invention claimed herein relates to a method for obtaining the product or a salt thereof according to the first aspect as an ultraviolet stabilizer.
[0020] The third aspect of the invention claimed herein relates to the use of the product of the first aspect or a salt thereof as a UV stabilizer.
[0021] The fourth aspect of the invention claimed herein relates to a composition comprising: the product of the first aspect or a salt thereof.
[0022] The fifth aspect of the invention claimed herein relates to a method for protecting a material or coating from light, wherein the method includes the step of providing a product or a salt thereof according to the first aspect as a UV stabilizer. Detailed Implementation
[0023] Before describing the inventive compositions and formulations of the invention claimed herein, it should be understood that the invention is not limited to the specific compositions and formulations described, as such compositions and formulations can naturally vary. It should also be understood that because the scope of the invention claimed herein will be defined only by the appended claims, the terminology used herein is not intended to be restrictive.
[0024] Furthermore, the scope defined throughout this specification also includes end values; that is, the range of 1 to 10 means that both 1 and 10 are included within this range. For the avoidance of doubt, the applicant is entitled to any equivalent in accordance with applicable law.
[0025] The different aspects of the invention claimed herein are defined in more detail in the following paragraphs. Each aspect so defined may be combined with any one or more other aspects unless expressly indicated otherwise. In particular, any feature indicated as preferred or advantageous may be combined with any one or more other features indicated as preferred or advantageous.
[0026] Throughout this specification, references to 'one embodiment' or 'an embodiment' mean that a particular feature, structure, or characteristic described in connection with that embodiment is included in at least one embodiment of the invention claimed herein. Therefore, the phrase 'in one embodiment' appearing in different places throughout this specification does not necessarily refer to the same embodiment.
[0027] Furthermore, in one or more embodiments, specific features, structures, or characteristics may be combined in any suitable manner, as will be apparent to those skilled in the art from this disclosure. Moreover, although some embodiments described herein include some but not others included in other embodiments, combinations of features from different embodiments are intended to be within the scope of the invention claimed herein and form different embodiments, as will be understood by those skilled in the art. For example, in the appended claims, any of the claimed embodiments may be used in any combination.
[0028] In the context of this invention, the product can be used as an ultraviolet (UV) stabilizer or a light stabilizer. The term can be defined as a product or compound having the ability to absorb light in UVA and / or UVB. As mentioned above, stabilizers are primarily used to reduce photodegradation (e.g., in plastics or polymers) by playing a key role in suppressing the generation of free radicals that lead to plastic degradation. Suitable stabilizers typically have at least one maximum absorption value in the range of 280 to 420 nm.
[0029] In the context of the invention claimed herein, as used herein, the term "alkyl" refers to a non-cyclic saturated aliphatic group, including straight-chain or branched alkyl saturated hydrocarbon groups, defined by the general formula C1. n H 2n+1 It is represented as n, where n is the number of carbon atoms, such as 1, 2, 3, 4, etc.
[0030] In the context of the invention claimed herein, unsubstituted linear C1-C 24The alkyl group is preferably selected from the group consisting of: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl; more preferably selected from the group consisting of: hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, and eicosyl. The group consists of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl; most preferably the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; and particularly the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl.
[0031] In the context of the invention claimed herein, the C1-C of the unsubstituted branch 24 The alkyl group is preferably selected from the group consisting of: isopropyl, isobutyl, neopentyl, 2-ethylhexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, and isoeicosyl, more preferably selected from the group consisting of: 2-ethylhexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, isoeicosyl, 2-methyltricaryl, 2-ethyldocodecyl, 3-ethyldocoalkyl, 3-ethyleicosyl, 4-propyldocoalkyl, propylnonadecyl, 6-butyldodecyl, and 5-ethylundecyl.
[0032] In the context of the invention claimed herein, the C1-C of the substituted straight or branched chains 24 Alkyl refers to a group having C1-C2 atoms. 24 The functional group of the carbon atom is a substituted branched or straight-chain saturated hydrocarbon group selected from the group consisting of: hydroxyl, alkoxy, C(=O)-R, CN, and SR, wherein R is selected from the group consisting of: hydrogen, substituted or unsubstituted straight-chain or branched C1-C. 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, and substituted or unsubstituted C7-C 24 Arylalkyl.
[0033] In the context of the invention claimed herein, the C1-C of the substituted straight or branched chains 24The alkyl group is preferably selected from the group consisting of: 1-hydroxymethyl, 1-methoxymethyl, 1-hydroxyethyl, 1-hydroxypropyl, 1-hydroxybutyl, 1-hydroxypentyl, 1-hydroxyhexyl, 1-hydroxyheptyl, 1-hydroxyoctyl, 1-hydroxynonyl, decyl, 1-hydroxyundecyl, 1-hydroxydodecyl, 1-hydroxytridecyl, 1-hydroxytetradecyl, 1-hydroxypentadecanyl, 1-hydroxyhexadecyl, 1-hydroxyheptadecyl, 1-hydroxyheptadecyl, 1-hydroxyoctadecyl, 1-hydroxynonadecanyl, 1-hydroxyeicosyl, 1-hydroxytidecyl, 1-hydroxytetradecyl, 1-methoxymethyl, 1-methoxyethyl, 1-methoxypropyl, 1-methoxy Butyl, 1-methoxypentyl, 1-methoxyhexyl, 1-methoxyheptyl, 1-methoxyoctyl, 1-methoxynonyl, decyl, 1-methoxyundecyl, 1-methoxydodecyl, 1-methoxytridecyl, 1-methoxytetradecyl, 1-methoxypentadecanyl, 1-methoxyhexadecyl, 1-methoxyheptadecyl, 1-methoxyoctadecyl, 1-methoxynonadecanyl, 1-methoxyeicosyl, 1-methoxyhexadecyl, 1-methoxytetradecyl, 1-methoxytetradecyl, 2-methoxypropyl, 2-methoxybutyl, 2-methoxypentyl, 2-methoxyhexyl, 2-methoxyheptyl, 2-methoxyoctyl, 2-methoxynonyl, decyl 2-Methoxyundecyl, 2-Methoxydodecyl, 2-Methoxytridecyl, 2-Methoxytetradecyl, 2-Methoxypentadecanyl, 2-Methoxyhexadecyl, 2-Methoxyheptadecyl, 2-Methoxyoctadecyl, 2-Methoxynonadecanyl, 2-Methoxyeicosyl, 2-Methoxytimonodecyl, 2-Methoxytimonodecyl, 2-Methoxytetradecyl, 1-Acetoxymethyl, 1-Acetoxyethyl, 1-Acetoxypropyl, 1-Acetoxybutyl, 1-Acetoxypentyl, 1-Acetoxyhexyl, 1-Acetoxyheptyl, 1-Acetoxyoctyl, 1-Acetoxynonyl, Decyl, 1-Acetoxyundecyl, 1-Acetoxydodecyl 1-Acetoxytridecyl, 1-Acetoxytetradecyl, 1-Acetoxypentadecanyl, 1-Acetoxyhexadecyl, 1-Acetoxyheptadecyl, 1-Acetoxyoctadecyl, 1-Acetoxynonadecanyl, 1-Acetoxyeicosyl, 1-Acetoxytetradecyl, 1-Acetoxydodecyl, 1-Acetoxytetradecyl, 1-Acetoxytetradecyl, 1-Cyanomethyl, 1-Cyanoethyl, 1-Cyanopropyl, 1-Cyanobutyl, 1-Cyanopentyl, 1-Cyanohexyl, 1-Cyanohepyl, 1-Cyanoctyl, 1-Cyannonyl, decyl, 1-Cyanundecyl, 1-Cyandodecyl, 1-Cyanotridecyl, 1-Cyanotetradecyl, 1-Cyanoctadecyl1-Cyanohexadecanyl, 1-Cyanohepadecanyl, 1-Cyanoctadecyl, 1-Cyanonadecanyl, 1-Cyanoelectoalkyl, 1-Cyanoelectoalkyl, 1-Cyanoelectodialkyl, 1-Cyanoelectotrialkyl, 1-Cyanoelectotetraalkyl, 2-Cyanopropyl, 2-Cyanobutyl, 2-Cyanopentyl, 2-Cyanohexyl, 2-Cyanohepyl, 2-Cyanoctadecyl, 2-Cyanonyl, decyl, 2-Cyanoundecyl, 2-Cyanododecyl, 2-Cyanotridecyl, 2-Cyanotetradecyl, 2-Cyanopentadecanyl, 2-Cyanohexadecyl, 2-Cyanoheptadecyl, 2-Cyanooctadecyl, 2-Cyanononadecanyl, 2-Cyanoelectoalkyl, 2-Cyanoelectoalkyl, 2-Cyanoelectoalkyl, 2-Cyanoelectodecyl, 2-Cyanoelectodecyl, 2-Cyanoelectodecyl Dialkyl, 2-cyanotrichoryl, 2-cyanotetraalkyl, 1-thioacrylmethyl, 1-thioacrylethyl, 1-thioacrylpropyl, 1-thioacrylbutyl, 1-thioacrylpentyl, 1-thioacrylhexyl, 1-thioacrylheptyl, 1-thioacryloctyl, 1-thioacrylnonyl, decyl, 1-thioacrylundecyl, 1-thioacryldodecyl, 1-thioacryltridecyl, 1-thioacryltetradecyl, 1-thioacrylpentyl, 1-thioacrylhexadecyl, 1-thioacrylheptadecyl, 1-thioacryloctadecyl, 1-thioacrylnonadecanyl, 1-thioacryleicosyl, 1-thioacrylonedecyl, 1-thioacrylonedecyl, 1-thioacrylonecos ...
[0034] In the context of the invention claimed herein, the term alkenyl means an unsubstituted straight-chain C2-C 24The alkenyl group is preferably selected from the group consisting of: 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tetraceneenyl, 2-tetraceneenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecanenyl, 2-pentadecanenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecanenyl, 2-nonadecanenyl, 1-eicoseneenyl, and 2-eicoseneenyl, more preferably... Selected from 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tetraceneenyl, 2-tetraceneenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecanenyl, 2-pentadecanenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecanenyl, 2-nonadecanenyl, 1-eicosene and 2-eicosene, 20-tetraceneenyl, 2-tetraceneenyl, 6-tetraceneenyl and 2-tetraceneenyl.
[0035] In the context of the invention claimed herein, the C2-C of the unsubstituted branch 24The alkenyl group is selected from the group consisting of: isopropenyl, isobutylenyl, neopentenyl, 2-ethylhexenyl, 2-propylheptenyl, 2-butyloctenyl, 2-pentylnonenyl, 2-hexyldecenyl, isohexenyl, isoheptenyl, isooctenyl, isononenyl, isodecanenyl, isodecadecenyl, isododecenyl, isotetradecenyl, isohexadecanenyl, 2-methyltetradecenyl, 2-ethyldodecenyl, 3-ethyltetradecenyl, 3-ethyleicosene, 4-propyltetradecenyl, 4-propylnonadecanenyl, 6-butyldodecenyl, 5-ethylundecenyl, 1,4-hexanediol. Alkenyl, 1,3-hexadienyl, 2,5-hexadienyl, 3,5-hexadienyl, 2,4-hexadienyl, 1,3,5-hextrienyl, 1,3,6-heptadienyl, 1,4,7-octriatrienyl or 2-methyl-1,3,5-hextrienyl, 1,3,5,7-octriatrienyl, 1,3,5,8-nonatraenyl, 1,4,7,10-undecanetetraenyl, 2-ethyl-1,3,6,8-nonatraenyl, 2-vinyl-1,3,5,8-nonatraenyl, 1,3,5,7,9-decanepentyl, 1,4,6,8,10-undecanepentyl and 1,4,6,9,11-dodecanepentyl.
[0036] In the context of the invention claimed herein, the C2-C of the substituted straight or branched chain... 24 Alkenyl refers to a group with C2-C... 24 A branched or straight-chain unsaturated hydrocarbon group with one carbon atom substituted by a functional group selected from the following: hydroxyl, alkoxy, C(=O)-R, CN, and SR; wherein R is hydrogen, substituted or unsubstituted, straight-chain or branched C1-C 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, substituted or unsubstituted C7-C 24 Arylalkyl.
[0037] In the context of the invention claimed herein, the C2-C of the substituted straight or branched chain... 24The alkenyl group is preferably selected from the group consisting of: 2-hydroxypropenyl, 3-hydroxybutenyl, 3-hydroxypentenyl, 5-hydroxyhexenyl, 7-hydroxyheptenyl, 3-hydroxyoctenyl, 5-hydroxynonenyl, decyl, 11-hydroxyundecenyl, 9-hydroxydodecenyl, 6-hydroxytetadedecenyl, 4-hydroxytetradecenyl, 6-hydroxypentadedecenyl, 3-hydroxyhexadecenyl, 2-hydroxyheptadecenyl, 7-hydroxyoctadecenyl, 6-hydroxynonadedecenyl, 4-hydroxyeicosenoenyl, 2-hydroxythodecenyl, 3-hydroxythodecenyl, 2-hydroxythodecenyl, 3-hydroxythodecenyl, 2-hydroxythodecenyl, 23-hydroxythodecenyl, 1-methoxyvinyl, 2-methoxypropenyl, 4-methoxybutenyl, 3- Methoxypentenyl, 5-methoxyhexenyl, 2-methoxyheptenyl, 5-methoxyoctenyl, 3-methoxynonenyl, 6-methoxyundecenyl, 1-methoxydodec-2-enyl, 1-methoxytridec-5-enyl, 3-methoxytetradec-5-enyl, 3-methoxypentadecan-12-enyl, 10-methoxyhexadec-15-enyl, 12-methoxyheptadec-16-enyl, 1-methoxyoctadec-3-enyl, 1-methoxynondecan-2-enyl, 1-methoxyeicosaecan-20-enyl, 1-methoxytetradec-2-enyl, 1-methoxytetradec-4-enyl, 1-methoxytetradec-22-enyl, 1-methoxytetradec-23-enyl, 2- Methoxypropyl-1-enyl, 2-methoxybut-1-enyl, 2-methoxypent-4-enyl, 2-methoxyhex-2-enyl, 2-methoxyhept-3-enyl, 2-methoxyoct-7-enyl, 2-methoxynon-5-enyl, 2-methoxyundec-10-enyl, 2-methoxydodec-4-enyl, 2-methoxytridec-12-enyl, 2-methoxytetradec-10-enyl, 2-methoxypentadecan-14-enyl, 2-methoxyhexadec-1-enyl, 2-methoxyheptadec-1-enyl, 2-methoxyoctadec-12-enyl, 2-methoxynondec-10-enyl, 2-methoxyeicosaecan-18-enyl, 2-methoxytetradec-2-enyl, 2-methoxydi Dodecyl-3-enyl, 20-methoxy-3-carbon-2-enyl, 21-methoxy-4-carbon-2-enyl, 1-acetoxyvinyl, 1-acetoxyprop-1-enyl, 1-acetoxybut-2-enyl, 1-acetoxypentan-4-enyl, 1-acetoxyhex-2-enyl, 1-acetoxyheptan-1-enyl, 1-acetoxyoctan-7-enyl, 1-acetoxynon-2-enyl, 5-acetoxydecan-3-enyl, 1-acetoxyundecan-10-enyl, 1-acetoxydodecadecan-2-enyl, 1-acetoxytetridecadecan-12-enyl, 10-acetoxytetradecan-2-enyl, 15-acetoxypentadecadecan-2-enyl, 10-acetoxyhexadecan-2-enyl11-Acetoxyheptadec-1-enyl, 13-Acetoxyhexadecadec-2-enyl, 1-Acetoxyhexadecadec-14-enyl, 20-Acetoxyheicodec-19-enyl, 1-Acetoxyhexadec-2-enyl, 1-Acetoxyhexadec-10-enyl, 1-Acetoxyhexadec-22-enyl, 1-Acetoxyhexadec-23-enyl, 1-Cyanoethyl-1-enyl, 1-Cyanoprop-2-enyl, 1-Cyanobut-2-enyl, 1-Cyanopent-3-enyl, 1-Cyanohex-5-enyl, 1-Cyanohept-6-enyl, 1-Cyanooct-2-enyl, 1-Cyanonon-3-enyl, 11-Cyanoundec-2-enyl, 10-Cyanododec-2- Alkenyl, 10-cyanotridecyl-12-alkenyl, 1-cyanotetradecyl-3-alkenyl, 1-cyanopentadecanyl-14-alkenyl, 1-cyanohexadecyl-15-alkenyl, 1-cyanoheptadecyl-2-alkenyl, 1-cyanooctadecyl-3-alkenyl, 1-cyanononadecanyl-18-alkenyl, 1-cyanoeicosodecanyl-10-alkenyl, 1-cyanotidecyl-20-alkenyl, 15-cyanotidecyl-3-alkenyl, 1-cyanotidecyl-20-alkenyl, 1-cyanotidecyl-2-alkenyl, 2-cyanoprop-2-alkenyl, 2-cyanobut-1-alkenyl, 2-cyanopent-1-alkenyl, 2-cyanohex-3-alkenyl, 2-cyanoheptyl-6-alkenyl, 2-cyanooctyl-1-alkenyl, 2-cyanononyl-8 -Alkenyl, 2-cyanoundec-10-alkenyl, 2-cyanododec-1-alkenyl, 2-cyanotridec-12-alkenyl, 2-cyanotetradec-10-alkenyl, 2-cyanopentadecadec-3-alkenyl, 2-cyanohexadec-2-alkenyl, 2-cyanoheptadec-1-alkenyl, 2-cyanooctadec-12-alkenyl, 2-cyanononadecadec-15-alkenyl, 2-cyanoeicosode-1-alkenyl, 2-cyanotetradec-5-alkenyl, 2-cyanotetradec-20-alkenyl, 2-cyanotetradec-22-alkenyl, 2-cyanotetradec-20-alkenyl, 1-thionyleth-1-alkenyl, 1-thionylprop-2-alkenyl, 1-thionylbut-2-alkenyl, 1-thionylpentyl- 4-Alkenyl, 1-Thionylhex-2-Alkenyl, 1-Thionylhept-5-Alkenyl, 1-Thionyloct-3-Alkenyl, 1-Thionylnon-5-Alkenyl, 1-Thionylundec-10-Alkenyl, 1-Thionyldodec-11-Alkenyl, 1-Thionyltridec-2-Alkenyl, 1-Thionyltetradec-4-Alkenyl, 1-Thionylpentadecande ...1-Thionyl tridecano-20-enyl and 1-Thionyl tetradecano-22-enyl.
[0038] In the context of the invention claimed herein, substituted or unsubstituted C5-C 24 Cycloalkyl groups refer to 5- to 24-membered saturated alicyclic groups, both monocyclic and bicyclic. They are unsubstituted or branched C5-C... 24 Representative examples of monocyclic and bicyclic cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclic [2.2.1]heptyl, and bicyclic [3.1.1]heptyl.
[0039] In the context of the invention claimed herein, C5-C 24 Monocyclic and bicyclic cycloalkyl groups can be further branched with one or more identical or different alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, neopentyl, etc. Branched C3-C 10 Representative examples of monocyclic and bicyclic cycloalkyl groups include, but are not limited to, methylcyclohexyl and dimethylcyclohexyl.
[0040] In the context of the invention claimed herein, unsubstituted or substituted C5-C 24 Cycloalkenyl groups refer to 5- to 24-membered unsaturated alicyclic groups comprising one or more double bonds in monocyclic and bicyclic structures. (C5-C) 24 Representative examples of cycloalkenyl groups include, but are not limited to, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, or cyclodecenyl. These groups may be branched with one or more of the same or different alkyl groups, preferably branched with methyl, ethyl, n-propyl, or isopropyl. Branched C5-C 24 Representative examples of monocyclic and bicyclic cycloalkenyl groups include, but are not limited to, methylcyclohexenyl and dimethylcyclohexenyl.
[0041] In the context of the invention claimed herein, substituted or unsubstituted C6-C 24 Aryl groups can have more than one aromatic ring. Substituted and unsubstituted C6-C 24 Representative examples of aryl groups include phenyl, naphthyl, anthracene, tetraphenyl, phenatenyl, and phenanthrene.
[0042] In the context of the invention claimed herein, arylalkyl means an aryl ring attached to an alkyl chain. Representative examples of arylalkyl include, but are not limited to, 1-phenylmethyl, 1-phenylethyl, 1-phenylpropyl, 1-phenylisopropyl, 1-phenylbutyl, 1-methyl-1-phenyl-propyl, 3-phenylpropyl, 4-phenylbutyl, 3-phenylbutyl, and 2-methyl-3-phenyl-propyl.
[0043] In the context of the invention claimed herein, the replacement of C6-C24 Aryl groups refer to aromatic rings with substitutions at different positions. (C6-C) 24 Aryl groups can have more than one aromatic ring. Substituted and unsubstituted C6-C 24 Representative examples of aryl groups include tolyl, xylyl, 2-hydroxyphenyl, 2,3-dihydroxyphenyl, 2-methoxyphenyl, 2-hydroxy-4-methoxyphenyl, 2,4-dimethoxyphenyl, 2-chlorophenyl, 2-chloro-4-hydroxyphenyl, 2-chloro-4-methoxyphenyl, 3-chloro-4-methoxyphenyl, 2-methyl-4-methoxy-6-chlorophenyl, and 2-acetyl-4-hydroxyphenyl.
[0044] In the context of the invention claimed herein, the term alkylene refers to a noncyclic saturated hydrocarbon chain combining different moieties. Alkylene refers to an unsubstituted straight-chain C1 to C12 hydrocarbon chain selected from, but not limited to, the following. 30Carbon atoms: -CH2-, -CH2-CH2-, -CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-,-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-、-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-。、
[0045] In the context of this invention, the branched, unsubstituted alkylene group is selected from, but not limited to: -CH2-C(CH3)H-, -CH2-C(CH3)H-CH2-, -CH2-CH2-C(CH3)H-CH2-, -C(CH3)2-CH2-CH2-C(CH3)H-CH2-, -CH2-C(CH3)H-CH2-CH2-CH2-CH2-CH2-, -CH2-C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-C(CH3)H-, -C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-CH2 -CH2-CH2-, -C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -C(CH3)2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-C(CH3)2-CH2 -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -C(CH3)2-CH2-CH2-CH2-CH2-CH 2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -C(CH3)H-CH2-CH2-CH2- CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-C(CH3)H-, -C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2- CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-,-C(CH3)H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -C(CH3 )H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-, -C(CH3)H -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-or-C(CH3 )H-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-. ,
[0046] Therefore, the invention claimed herein relates to a product or a salt thereof, which can be obtained by a method comprising the following steps:
[0047] a) To prepare at least one compound having formula (I) in the presence of at least one catalyst,
[0048]
[0049] Wherein G* is selected from substituted 2-(2-hydroxyphenyl)-2H-benzotriazole groups or substituted 2-hydroxyphenyl-triazine.
[0050] R 30 Selected from hydrogen, substituted or unsubstituted straight or branched C1-C 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, substituted or unsubstituted C7-C 24 Arylalkyl, substituted or unsubstituted straight or branched C1-C 24 Heteroalkyl or -S(=O)2R 31 , where R 31 C1-C selected from substituted or unsubstituted straight or branched chains 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C24 cycloalkyl, substituted or unsubstituted C6-C 24 aryl, substituted or unsubstituted C7-C 24 Arylalkyl;
[0051] b) Reaction with a polyether polyol, which is obtained by reacting a composition of the following:
[0052] b1) Based on 5 wt% to 90 wt% of the total amount of the polyether polyol, at least one sugar selected from C5-C6 sugar alcohols, monosaccharides, oligosaccharides, polysaccharides or mixtures thereof;
[0053] b2) At least one epoxy alkane, comprising 5 wt% to 90 wt% of the total amount of polyether polyol;
[0054] b3) at least one polyol having 2 to 4 hydroxyl groups, comprising 0 wt% to 90 wt% of the total amount of the polyether polyol; and
[0055] b4) Based on a total amount of 0 wt% to 15 wt% of at least one optional reactant selected from fatty acids, fatty acid monoesters or mixtures thereof.
[0056] Preferably, R 30 Selected from hydrogen, substituted or unsubstituted straight or branched C1-C 24 Alkyl, substituted or unsubstituted straight or branched C1-C 24 Heteroalkyl, or substituted or unsubstituted C7-C 16 Arylalkyl.
[0057] More preferably, R 30 Selected from hydrogen, substituted or unsubstituted straight or branched C1-C 16 Alkyl, substituted or unsubstituted straight or branched C1-C 16 Heteroalkyl, or unsubstituted C7-C 12 Arylalkyl.
[0058] Even more preferably, R 30 Selected from hydrogen, unsubstituted straight-chain C1-C 10 Alkyl, or unsubstituted C7-C 10 Arylalkyl.
[0059] Preferably, G* is selected from substituted 2-hydroxyphenyl-triazine.
[0060] More preferably, the substituted 2-hydroxyphenyl-triazine is selected from formula (A),
[0061]
[0062] Z is selected from C1-C of substituted or unsubstituted straight or branched chains.30 Alkylene, substituted or unsubstituted straight-chain or branched 2- to 30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 24 Alkenyl, substituted or unsubstituted straight-chain or branched 3- to 30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 24 Cycloalkylene, or substituted or unsubstituted C6-C 24 Alpha-aryl
[0063] Ar1 and Ar2 are independent parts of equation (C).
[0064]
[0065] The dashed lines represent single bonds between formula (C) and the triazine ring having formula (A), and R1, R2, R3, R4, and R5 are independently selected from hydrogen, substituted or unsubstituted straight-chain or branched C1-C bonds. 24 Alkyl, substituted or unsubstituted C6-C 24 Aryl, -OH, -OC1-C 24 Alkyl group; or a part having the formula (M),
[0066]
[0067] The dashed lines represent single bonds between formula (M) and the triazine ring having formula (A), and Z is attached to -C(=O)OR. 30 ,
[0068] R6, R7, and R8 are independently selected from hydrogen, or from substituted or unsubstituted straight-chain or branched C1-C atoms. 24 alkyl.
[0069] More preferably, at least one of Ar1 and Ar2 is a part of formula (C) independently of each other.
[0070] More preferably, R1, R2, R3, R4, and R5 are independently selected from hydrogen, OH, substituted or unsubstituted C1-C. 24 Alkyl, substituted or unsubstituted C6-C 24 aryl, or substituted or unsubstituted -O-C1-C 24 alkyl.
[0071] More preferably, at least one of Ar1 and Ar2 in formula (A) is a part of formula (C-1) independently of each other.
[0072]
[0073] The dashed lines represent single bonds between formula (C) and the triazine ring having formula (A), and R1, R2, and R3 are independently selected from hydrogen, substituted or unsubstituted straight-chain or branched C1-C bonds. 24 Alkyl, substituted or unsubstituted C6-C 24 Aryl, -OH, substituted or unsubstituted -OC1-C 24 alkyl.
[0074] More preferably, at least one of Ar1 and Ar2 in formula (A) is independently a part having formula (C-1), wherein R1, R2 and R3 are independently selected from hydrogen, C1-C3 alkyl, unsubstituted C6-C 12 Aryl, -OH, or substituted or unsubstituted -O-C1-C 16 alkyl.
[0075] More preferably, at least one of Ar1 and Ar2 in formula (A) is a part of formula (M) independently of each other.
[0076] More preferably, at least one of Ar1 and Ar2 in formula (A) is independently a part of formula (M), wherein R6, R7 and R8 are independently selected from hydrogen, or substituted or unsubstituted straight-chain or branched C1-C. 10 alkyl.
[0077] Even more preferably, at least one of Ar1 and Ar2 in formula (A) is independently a part of formula (M), wherein R6, R7 and R8 are derived from hydrogen or unsubstituted straight-chain C1-C6 alkyl, more preferably from hydrogen or methyl.
[0078] Most preferably, the substituted 2-hydroxyphenyl-triazine is selected from formula (A) as described herein, wherein Z is selected from substituted or unsubstituted straight-chain or branched C1-C8 alkylene groups; R1, R2, R3, R4 and R5 are independently selected from hydrogen, unsubstituted C1-C6 alkyl, unsubstituted C6-C 12 Aryl, -OH or -OC1-C6 alkyl; and R6, R7 and R8 are hydrogen.
[0079] Preferably, G* is selected from a substituted 2-(2-hydroxyphenyl)-2H-benzotriazole group.
[0080] Preferably, the substituted 2-(2-hydroxyphenyl)-2H-benzotriazole is selected from formula (B).
[0081]
[0082] Where R 41 and R 42 Independently selected from hydrogen, halogen, substituted or unsubstituted straight-chain or branched C1-C atoms24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, or substituted or unsubstituted C7-C 24 Arylalkyl.
[0083] More preferably, the substituted 2-(2-hydroxyphenyl)-2H-benzotriazole is selected from formula (B), wherein R 41 and R 42 Independently selected from hydrogen, halogen, substituted or unsubstituted straight-chain or branched C1-C atoms 10 Alkyl or substituted or unsubstituted C7-C 16 Arylalkyl.
[0084] Even more preferably, the substituted 2-(2-hydroxyphenyl)-2H-benzotriazole is selected from formula (B), wherein R 41 and R 42 Independently selected from hydrogen, halogen, unsubstituted straight-chain or branched C1-C6 alkyl groups, or substituted or unsubstituted C7-C groups. 10 Arylalkyl.
[0085] More preferably, G* is selected from compounds having formula (A) or formula (B).
[0086]
[0087] Z is selected from C1-C of substituted or unsubstituted straight or branched chains. 30 Alkylene, substituted or unsubstituted straight-chain or branched 2- to 30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 24 Alkenyl, substituted or unsubstituted straight-chain or branched 3- to 30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 24 Cycloalkylene, or substituted or unsubstituted C6-C 24 Alpha-aryl
[0088] Ar1 and Ar2 are independent parts of equation (C).
[0089]
[0090] The dashed lines represent single bonds between formula (C) and the triazine ring having formula (A), and R1, R2, R3, R4, and R5 are independently selected from hydrogen, substituted or unsubstituted straight-chain or branched C1-C bonds. 24 Alkyl, substituted or unsubstituted C6-C 24Aryl, -OH, -OC1-C 24 Alkyl group; or a part having the formula (M),
[0091]
[0092] The dashed lines represent single bonds between formula (M) and the triazine ring having formula (A), and Z is attached to -C(=O)OR. 30 ,
[0093] R6, R7, and R8 are independently selected from hydrogen, or from substituted or unsubstituted straight-chain or branched C1-C atoms. 24 alkyl;
[0094] Where R 41 and R 42 Independently selected from hydrogen, halogen, substituted or unsubstituted straight-chain or branched C1-C atoms 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, or substituted or unsubstituted C7-C 24 Arylalkyl.
[0095] Halogens can be selected from fluorine, chlorine, bromine or iodine, with chlorine being preferred.
[0096] More preferably, the compound of formula (I) according to the invention claimed herein is selected from methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, ethyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionic acid, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionic acid, methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionic acid, methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionate Ester, ethyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)- Ethyl 1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, ethyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]octanoate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-2-methyl-propionate ...3-butoxy-propionate, methyl 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, methyl 2-[4,6-bis(2,4-dimethyl Methyl 2-[[4,[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]hexanoate, methyl 2-[4,[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4,[4,6-bis[2-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]isooctyl propionate (tinuvin) 477), 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]isooctyl propionate (tinuvin 479), 2-[4-[4,6-bis[2-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octyl propionate (tinuvin 477), 2-[4-[4,6-bis(4-phenylphenyl)-1,3,6-Methylheptyl 5-triazin-2-yl]-3-hydroxyphenoxy]propionate (tinuvin 479), octyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]propionate, methyl 2-[2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]ethoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]-3-butoxy-propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-] Methyl [(1-methoxycarbonylpropoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]phenoxy]butyrate, methyl [4-[4,6-bis(4-butoxy-2-hydroxy-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl [4-[4,6-bis(4-hexyloxy-2-hydroxy-3-methyl-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-2-methyl-phenoxy]propionate, methyl [4-[4,6-bis(4-hexyloxy-2-hydroxy-3-methyl-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-2-methyl-phenoxy]propionate, methyl [4-[4,6-bis(4-phenylphenyl)]propionate, methyl [ ... [4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]ethyl butyrate, [4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]methyl octanoate, [4-[4,6-bis[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]methyl butyrate, [4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]methyl butyrate, [4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy] Methyl butyrate, ethyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-6-(4-methoxyphenyl)-1,3,methyl 5-triazine-2-yl]phenoxy]propionate, or a combination of two or more thereof, more preferably, the compound of formula (I) according to the invention claimed herein is selected from methyl 3-[3-(benzotriazine-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, ethyl 3-[3-(benzotriazine-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, 3-[3-(benzotriazine-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, 3-[3-tert-butyl-5-(5-chlorobenzotriazine-2-yl)-4-hydroxy-phenyl]propionate, 3-[ ... Methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionate, ethyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenyl ... Methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-2-methyl-propionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate Methyl hexanoate, methyl 2-[4-[4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, isooctyl 2-[4-[4,6-bis[2-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate (tinuvin477), isooctyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate (tinuvin477) 479), methyl 2-[2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]ethoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-6-(4-methoxyphenyl)-1,3,Methyl 5-triazin-2-yl]phenoxy]butyrate, methyl 2-[4-[4,6-bis(4-butoxy-2-hydroxy-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-hexyloxy-2-hydroxy-3-methyl-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-2-methyl-phenoxy]propionate, ethyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate, methyl 2-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate, methyl 2-[4,6-bis[2-hydroxy-] Methyl [4-(1-methoxycarbonylpropoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl [4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, ethyl [4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl [4-[4,6-bis[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl [3-hydroxy-4-[4-[2-hydroxy-4-(2-methoxy-1-methyl-1-methyl]-[4-hydroxy-4-methyl]-[4-[2-hydroxy-4-(2-methoxy-1-methyl]-[4-[] ... [-2-oxo-ethoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]phenoxy]propionate methyl ester, or a combination of two or more thereof, most preferably the compound of formula (I) according to the invention claimed herein is selected from methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, ethyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl) ... Methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]butyrate, methyl 2-[4,6-bis(2,Methyl 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-2-methylpropionate, methyl 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate, methyl 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy] Methyl hexanoate, methyl 2-[4-[4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, isooctyl 2-[4-[4,6-bis[2-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate (tinuvin 477), isooctyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate (tinuvin 477) 479), methyl 2-[2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]ethoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]phenoxy]butyrate, methyl 2-[4-[4,6-bis(4-butoxy-2-hydroxy-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-hexyloxy-2-hydroxy-3-methyl]propionate, methyl 2 ... Methyl propionate of [-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-2-methylphenoxy], ethyl butyrate of 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy], methyl octanoate of 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy], methyl octanoate of 2- Methyl [4-[4,6-bis[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl [4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl [4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl [4,6-bis(4-phenylphenyl)-1,3,[5-triazine-2-yl]-3-hydroxy-phenoxy]ethyl propionate, or combinations of two or more thereof, and particularly, according to the invention claimed herein, compounds having formula (I) are selected from methyl 3-[3-(benzotriazine-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, ethyl ...[3-(benzotriazine-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, ethyl 3-[[[3-(benzotriazine-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, ethyl 3-[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[ [2-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionic acid, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionic acid, methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionic acid, ethyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionic acid, or combinations of two or more thereof.
[0097] More preferably, the compound having formula (I) is selected from methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, ethyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionic acid, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionic acid, methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionate, ethyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionate, ethyl 3-[4-[4,6- Methyl bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate, ethyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate, octyl 2-[4-[4,6-diphenyl-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, ethyl 2 ...-3-butoxy-propionate, ethyl 2-[4,6-diphenyl-1,3,5-triaz Ethyl 2-[[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]octanoate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-2-methylpropionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]hexanoate, methyl 2-[4,6- Methyl bis(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis[2-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl 2-[2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl 2-[2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,Methyl 5-triazine-2-yl]-3-hydroxy-phenoxy]ethoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazine-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine-2-yl]phenoxy]butyrate, methyl 2-[4-[4,6-bis(4-butoxy-2-hydroxy- ... Methyl 2-[[4,6-bis(4,6-hexyloxy-2-hydroxy-3-methyl-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-2-methyl-phenoxy]propionate, methyl 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2-methyl-3-hydroxy-phenoxy]propionate, methyl 2-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate Ester, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate, methyl 2-[4-[4,6-bis[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4,6-bis(4-phenylphenyl)-1,3, Ethyl 5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]phenoxy]propionate, or combinations of two or more thereof.
[0098] Even more preferably, the compound having formula (I) is selected from methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate, and octyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate. Ester, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl 2-[4-[4,6-bis[2-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate [-yl]-3-hydroxyphenoxy]propionate 6-methylheptyl ester, 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2-methyl-3-hydroxyphenoxy]propionate methyl ester, 3-[3-(benzotriazin-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionate methyl ester, 3-[3-(benzotriazin-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionate ethyl ester, 3-[3- -(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionic acid, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionic acid, methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionic acid, ethyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionic acid, or combinations of two or more thereof.
[0099] Most preferably, the compound having formula (I) is selected from...
[0100]
[0101]
[0102] Preferably, the polyether polyol can be obtained by reacting a composition of the following:
[0103] b1) Based on 5 wt% to 80 wt%, more preferably 5 wt% to 70 wt%, more preferably 10 wt% to 60 wt% of the total amount of polyether polyol, at least one sugar selected from C5-C6 sugar alcohols, monosaccharides, oligosaccharides, polysaccharides or mixtures thereof;
[0104] b2) At least one epoxy alkane, based on a total amount of 5 wt% to 80 wt%, more preferably 5 wt% to 70 wt%, more preferably 10 wt% to 60 wt% of the polyether polyol;
[0105] b3) at least one polyol having 2 to 4 hydroxyl groups, comprising 0 wt% to 80 wt%, more preferably 0 wt% to 70 wt%, and even more preferably 5 wt% to 60 wt% of the total amount of the polyether polyol; and
[0106] b4) At least one optional reactant selected from fatty acids, fatty acid monoesters or mixtures thereof, based on a total amount of 0 wt% to 12 wt%, more preferably 1 wt% to 12 wt%, more preferably 2 wt% to 10 wt% of the polyether polyol.
[0107] Preferably, the polyether polyol is obtained by a method in the presence of a catalyst selected from the group consisting of amine catalysts, or oxides, hydroxides, or alkoxides of alkali metals or alkaline earth metals. The catalyst may be as defined in WO2011107366 A1. The amine catalyst is preferably selected from the group consisting of: trialkylamines, such as trimethylamine, triethylamine, tripropylamine, and tributylamine; dimethylalkylamines, such as dimethylethanolamine, dimethylcyclohexylamine, dimethylethylamine, and dimethylbutylamine; aromatic amines, such as dimethylaniline, dimethylaminopyridine, dimethylbenzylamine, pyridine, imidazoles such as imidazole, 4(5)-methylimidazole, 3-methylimidazole, and 1-hydroxypropylimidazole; guanidines and amidines, such as 1,5-diazabicyclo[4.3.0]non-5-ene and 1,5-diazabicyclo[5.4.0]undec-7-ene. The amine catalyst is preferably selected from dimethylethanolamine and imidazoles. The amine catalyst is preferably used in an amount of 0.1 wt.% to 1.0 wt.% of the total amount. This amount is particularly preferred when aliphatic amines are used.
[0108] More preferably, the catalyst is selected from oxides, hydroxides, or alkoxides of alkali metals or alkaline earth metals. The catalyst may be as described in WO 2011107367A1. Particularly preferably, the catalyst is selected from sodium hydroxide, potassium hydroxide, cesium hydroxide, or potassium tert-butoxide.
[0109] In the context of this invention, sugar can be defined as having at least one component with the general formula (CH2O). x The chemical part of the monosaccharide unit, wherein typically 7 ≥ x ≥ 3. Preferred monosaccharides are 5-carbon (pentose) or 6-carbon (hexose) sugars. It is well known that such monosaccharides can be chemically bonded to each other via glycosidic bonds to produce short-chain or long-chain (disaccharide, oligosaccharide, or polysaccharide). Both monosaccharides and bonded chains of sugars (disaccharides, oligosaccharides, or polysaccharides) are considered relevant to this invention. Suitable polysaccharides can be as defined in WO 2006040335 A1 and WO 2006040333A1.
[0110] Further classification of sugars can be based on the availability of free aldose or ketose groups that allow participation in reduction reactions. Reducing sugars such as glucose and non-reducing sugars such as sucrose are considered part of the invention claimed herein.
[0111] In the context of this invention, sugar is selected from C5-C6 sugar alcohols, monosaccharides, oligosaccharides, polysaccharides, or mixtures thereof. C5-C6 sugar alcohols have at least 5 hydroxyl groups, preferably 5-6 hydroxyl groups.
[0112] Preferably, at least one sugar is selected from sucrose, sorbitol, xylitol, mannitol, galactitol or a mixture thereof, and more preferably from sucrose, sorbitol or a mixture thereof.
[0113] Polyols are different from sugars (b1). Suitable polyols may be those described in WO 2011012599 A1. More preferably, the polyol is selected from glycerol, monoethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, dipropylene glycol, 1,4-butanediol, 1,6-hexanediol, pentaerythritol, trimethylolpropane or mixtures thereof, and preferably from glycerol, 1,2-propanediol, diethylene glycol, erythritol, pentaerythritol, trimethylolpropane or mixtures thereof.
[0114] Suitable polyether polyols can be prepared by oxyalkylation of at least one sugar. In principle, all suitable epoxides can be used in the method according to the invention. Preferably, C2-C... 20 Epoxides such as ethylene oxide, propylene oxide, 1,2-epoxybutane, 2,3-epoxybutane, isobutane, pentane, hexane, cyclohexane, phenylene oxide, dodecane, octadecane, and mixtures of these epoxides are suitable. Ethylene oxide, propylene oxide, 1,2-epoxybutane, 2,3-epoxybutane, isobutane, and pentane are more preferred, and propylene oxide and ethylene oxide are even more preferred.
[0115] Suitable polyether polyols can be prepared by methods described in the presence of fatty acids, fatty acid monoesters, or mixtures thereof. In the context of this invention, the term "fatty acids, fatty acid monoesters, or mixtures thereof" describes fatty acid glycerides, particularly fatty acid triglycerides, and / or fatty acid esters based on other monofunctional and polyfunctional alcohols. Suitable fatty acids or monoesters can be those listed in US 9284401B2 and US2014 / 0200327 A1. The fatty acid groups of the fatty acid esters can further carry hydroxyl groups, as in the case of castor oil. Of course, according to the invention, fatty acid esters whose fatty acid groups are subsequently modified with hydroxyl groups can also be used. Fatty acid groups modified in this way can be obtained, for example, by epoxidation of the olefinic double bond, followed by ring-opening of the ethylene oxide ring by means of a nucleophile or by hydroformylation / hydrogenation. For this purpose, unsaturated oils are also frequently treated with atmospheric oxygen at high temperatures.
[0116] In the context of this invention, triglycerides are suitable and are included in fatty acids, fatty acid monoesters, or mixtures thereof. Specific examples may be cottonseed oil, peanut oil, coconut oil, flaxseed oil, palm kernel oil, olive oil, corn oil, palm oil, castor oil, lesquerella oil, rapeseed oil, soybean oil, sunflower oil, herring oil, sardine oil, tallow, and lard. Of course, according to the invention, other fatty acid esters of monofunctional or polyfunctional alcohols and fatty acid glycerides having fewer than three fatty acid groups per glycerol molecule may also be used. Fatty acid triglycerides and other fatty acid esters of monofunctional and polyfunctional alcohols may also be used in mixtures.
[0117] Preferably, suitable polyether polyols can be prepared by an optional reaction in the presence of at least one compound selected from the following: lauric acid, myristic acid, palmitic acid, stearic acid, palmitoleic acid, oleic acid, erucic acid, linoleic acid, linolenic acid, tung oil acid, arachidonic acid and their monoesters, preferably selected from stearic acid, oleic acid or methyl esters of the mentioned fatty acids.
[0118] The reaction conditions and parameters required to obtain the polyether polyol are well known. These can be found, for example, in PCT / EP 2022 / 055942, EP 2542612, etc.
[0119] Preferably, the polyether polyol has an average number of hydroxyl groups in the range of 1 to 25, more preferably in the range of 1 to 20, even more preferably in the range of 1 to 15, most preferably in the range of 1 to 10, and particularly preferably in the range of 2 to 10.
[0120] During the method for obtaining polyether polyols, components may be added simultaneously or in a stepwise manner. Preferably, the polyether polyol is obtained by a method in which one or more of b1), b2), b3), or b4) are added in a stepwise manner. More preferably, b1), b2), and b3) are added simultaneously, followed by b4).
[0121] Preferably, the polyether polyol has an OH value or hydroxyl value in the range of 50 to 2000 mg KOH / g, more preferably 100 to 1500 mg KOH / g, and most preferably 200 to 800 mg KOH / g, as measured according to DIN 53 240 (1971-12).
[0122] Preferably, the polyether polyol has a viscosity in the range of 1,000 to 50,000 mPa·s, more preferably 1,000 to 45,000 mPa·s, even more preferably 1,000 to 30,000 mPa·s, and more preferably 2,000 to 30,000 mPa·s, as measured at 25°C according to DIN EN 12092.
[0123] Preferably, the polyether polyol has an estimated weight-average molecular weight of 100 to 2500 g / mol, more preferably 150 to 1000 g / mol, as determined by gel permeation chromatography (GPC) using polystyrene as an internal standard.
[0124] Preferably, the weight ratio of the compound having formula (I) to the polyether polyol is in the range of 1:10 to 10:1, more preferably in the range of 1:7 to 7:1, and most preferably in the range of 1:5 to 5:1.
[0125] The products of the present invention or their salts are obtained by a method as described herein in the presence of at least one catalyst.
[0126] Preferably, the catalyst is selected from protic acids, Sn compounds, Zr compounds, Bi compounds, Zn compounds, Al compounds, Ti compounds, or combinations of two or more thereof.
[0127] Preferably, the Zr compound is selected from zirconium acetate, zirconium octanoate, zirconium 2-ethylhexanoate, zirconium decanoate, zirconium neodecanoate, bis(acetyl-o)oxyzirconium, bis(cyclopentadienyl)zirconium bis(trifluoromethanesulfonic acid)tetrahydrofuran adduct, zirconium acetylacetonate (iv), zirconium tetrapropoxide (iv), zirconium tetrabutoxide (iv), 3-methyl-3-pentanol zirconium, tetra(2-methyl-3-buten-2-oxy)zirconium, tetra(1-methoxy-2-methyl-2-propoxy)zirconium, or mixtures thereof.
[0128] Preferably, the Zn compound is selected from zinc neodecanoate, zinc octanoate, zinc acetylacetone, zinc oxalate, zinc acetate, zinc propionate, zinc valerate, zinc neopentanoate, zinc octanoate, zinc succinate, zinc bis(2-ethylhexanoate), zinc laurate, zinc myristate, zinc bis(trifluoroacetic acid), zinc stearate, zinc citrate, zinc gluconate, or mixtures thereof.
[0129] Preferably, the Bi compound is selected from bismuth formate, bismuth octoate, bismuth octanoate, bismuth neodecanoate, bismuth subsalicylate, bismuth neododecanoate, bismuth neooctanoate, bismuth, trinedecanoate, bismuth triacetate, bismuth tri(2-ethylhexanoate), bismuth trifluoromethanesulfonate, bismuth β-naphthol, or mixtures thereof.
[0130] Preferably, the Sn compound is selected from dibutyltin oxide, dioctyltin dilaurate, dioctyltin oxide, dibutyltin diacetate, dioctyltin diacetate, tin neodecanoate, tin octanoate, tin acetylacetone, tin oxalate, tin acetate, tin propionate, tin valerate, tin neovalerate, tin octanoate, tin succinate, bis(2-ethylhexanoate)tin, tin laurate, dibutyltin dilaurate, tin myristate, bis(trifluoroacetic acid)tin, tin stearate, tin citrate, tin gluconate, or mixtures thereof.
[0131] Preferably, the Al compound is selected from aluminum neodecanoate, aluminum isopropoxide, aluminum octoate, aluminum acetylacetone, aluminum oxalate, aluminum acetate, aluminum propionate, or mixtures thereof.
[0132] Preferably, the Ti catalyst is selected from titanium isopropoxide (IV), titanium ethoxide (IV), titanium butoxide (IV), titanium acetylacetone (IV), titanium diisopropoxide-bis-(acetylacetone), or mixtures thereof.
[0133] Preferably, the catalyst is a protic acid. Preferred protic acids are selected from HCl, sulfuric acid, phosphoric acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, camphorsulfonic acid, methanesulfonic acid, benzoic acid, acetic acid, or mixtures thereof.
[0134] More preferably, the catalyst is a combination of at least one metal catalyst listed above and at least one protic acid listed above.
[0135] Preferably, the catalyst in the reaction is present in an amount ranging from 0.0001 wt.% to 30 wt.% based on the total weight of the compounds having formula (I). More preferably, the catalyst in the reaction is present in a total amount ranging from 0.01 wt.% to 10 wt.% based on the total weight of the compounds having formula (I). Even more preferably, the catalyst in the reaction is present in a total amount ranging from 0.01 wt.% to 5 wt.% based on the total weight of the compounds having formula (I). Most preferably, the catalyst in the reaction is present in a total amount ranging from 0.01 wt.% to 3.0 wt.% based on the total weight of the compounds having formula (I). In particular, the catalyst in the reaction is present in a total amount ranging from 0.01 wt.% to 1 wt.% based on the total weight of the compounds having formula (I).
[0136] In another preferred embodiment, the catalyst in the reaction is present in an amount based on the compound having formula (I) in the range of 0.0001 to 2.0 molar equivalents, more preferably in a total amount based on the compound having formula (I) in the range of 0.0001 to 1.0 molar equivalents, even more preferably in a total amount based on the compound having formula (I) in the range of 0.001 to 1.0 molar equivalents, most preferably in a total amount based on the compound having formula (I) in the range of 0.001 to 0.5 molar equivalents, and particularly in a total amount based on the compound having formula (I) in the range of 0.001 to 0.1 molar equivalents.
[0137] The product of this invention is obtained by a method carried out in the presence or absence of a solvent. This method can be carried out in the presence of a solvent or alternatively at high temperatures to ensure melting reaction conditions. When present, the solvent can be used in a minimum amount, as needed, to ensure proper mixing. In the context of this invention, some light stabilizers are known to be commercially available in suspension / solution form, in which case the existing solvent is sufficient and no additional solvent is required. Preferably, in the method for obtaining the claimed product, the reaction mixture is substantially free of any added liquid reactants or additives. Liquid additives include solvents, diluents, etc.
[0138] When the method is carried out in the presence of a solvent, the solvent is preferably selected from ethers, sulfones, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, N-methyl-dimethylacetamide, N-ethyl-dimethylacetamide, aromatic hydrocarbons, dichloroethane, halogenated aromatic hydrocarbons, or combinations of two or more thereof. More preferably, the solvent is selected from ethers, ketones, water, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, N-methyl-dimethylacetamide, N-ethyl-dimethylacetamide, aromatic hydrocarbons, dichloroethane, halogenated aromatic hydrocarbons, or combinations thereof. The solvent is selected from ethers, N,N-dimethylformamide, N-methyl-dimethylacetamide, N-ethyl-dimethylacetamide, aromatic hydrocarbons, dichloroethane, halogenated aromatic hydrocarbons, or combinations thereof. Most preferably, the solvent is selected from ethers, N,N-dimethylformamide, N-methyl-dimethylacetamide, N-ethyl-dimethylacetamide, aromatic hydrocarbons, halogenated aromatic hydrocarbons, or combinations thereof. In particular, the solvent is selected from ketones, ethers, aromatic hydrocarbons, halogenated aromatic hydrocarbons, water, or combinations thereof.
[0139] Preferably, the reaction is carried out in the presence of a solvent in an amount ranging from 0.01 to 20 times the total amount of formula (A) or (B), more preferably in the presence of a solvent in an amount ranging from 0.1 to 10 times the total amount of formula (I), even more preferably in the presence of a solvent in an amount ranging from 0.2 to 5.0 times the total amount of formula (I), most preferably in the presence of a solvent in an amount ranging from 0.5 to 3.0 times the total amount of formula (I), and particularly in the presence of a solvent in an amount ranging from 0.5 to 2.0 times the total amount of formula (I).
[0140] Preferably, the pH of the reaction is maintained at ≤9.0, more preferably in the range of ≥0.0 to ≤8.0, and even more preferably in the range of ≥4.0 to ≤8.0.
[0141] Preferably, the product of the present invention is obtained by a method performed at a temperature of ≥20°C, more preferably ≥40°C, even more preferably ≥60°C, and even more preferably ≥80°C. Preferably, the reaction of at least one compound having formula (I) with at least one polyether polyol is performed at a temperature ranging from ≥20°C to ≤200°C, more preferably ≥40°C to ≤160°C, and even more preferably ≥60°C to ≤120°C. The method can be performed for up to 48, 24, 18, 14, 12, 10, 8, 6, 4, 3, 2, 1, or 0.5 hours, more preferably 1 minute to 12 hours, and even more preferably 30 minutes to 3 hours. The method can preferably be performed in the presence of mechanical agitation (e.g., stirring). The method can also be performed by any known method using an external mechanical oscillator or by using a magnetic stirring bead, etc.
[0142] Preferably, the product obtained according to the invention claimed herein has a weight-average molecular weight in the range of 200 to 20,000, preferably in the range of 400 to 10,000, more preferably in the range of 500 to 8,000, and even more preferably in the range of 500 to 5,000, as determined by GPC using polystyrene as an internal standard.
[0143] Preferably, the product obtained according to the invention claimed herein has a solubility of more than 10 g / 100 mL xylene at room temperature; more preferably, the product obtained according to the invention claimed herein has a solubility of more than 20 g / 100 mL xylene at room temperature; most preferably, the product obtained according to the invention claimed herein has a solubility of more than 30 g / 100 mL xylene at room temperature; and particularly preferably, the product obtained according to the invention claimed herein has a solubility of more than 40 g / 100 mL xylene at room temperature.
[0144] The invention claimed herein also relates to a method for obtaining the product described above or a salt thereof, said method comprising the following steps:
[0145] i) To make a compound having formula I;
[0146] ii) with polyether polyols,
[0147] The reaction takes place in the presence of at least one catalyst.
[0148] The invention claimed herein also relates to the use of the products or salts described above as UV stabilizers. The use of light stabilizers as UV stabilizers can be applied in personal and home care applications, such as in cosmetics, plastics, or surface coatings (e.g., automotive coatings).
[0149] The invention claimed herein also relates to a composition comprising the product obtained as described above or a salt thereof.
[0150] Preferably, the composition can be solvent-based or water-based. Typical examples of organic solvents are aliphatic, aromatic, or alicyclic hydrocarbons, alcohols, glycols, esters, acetates, and ketones.
[0151] The invention claimed herein also relates to a method for protecting a material or coating from light, wherein the method includes the step of providing a product or a salt thereof obtained according to the invention claimed herein as a UV stabilizer. It is noted that the product or its salt provides long-term stability comparable to commonly used industrial standard UV absorbers (e.g., hydroxyphenylbenzotriazole absorbers).
[0152] Preferably, the composition can be solvent-based or water-based. Typical examples of organic solvents are aliphatic, aromatic, or alicyclic hydrocarbons, alcohols, glycols, esters, acetates, and ketones.
[0153] Preferably, the coating is a surface coating, such as those used in [the example]. Preferably, the composition is an automotive coating composition.
[0154] The coating composition is preferably a paint, particularly a paint for coating automobiles (automotive finish paint), such as paints containing alkyd / melamine resins and alkyd / acrylic / melamine resins (see H. Wagner and H. F. Sarx, "Lackkunstharze [Coating Synthetic Resins]" (1977), pp. 99-123), epoxy / carboxyl resins, isocyanate-crosslinked acrylic polyols, or polyester polyols. Other crosslinking agents include urea resins or end-capped isocyanates.
[0155] The coating composition preferably contains 0.01-10 parts by weight, especially 0.05-10 parts by weight, and more especially 0.1-5 parts by weight of the product according to the invention or its salt / 100 parts by weight of solid binder. The binder can, in principle, be any binder conventional in the art, such as those described in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, Vol. A18, pp. 368-426, VCH, Weinheim 1991. The binder will generally be a film-forming binder, based on thermoplastic or thermosetting resins, primarily thermosetting resins. Examples include alkyd, acrylic, polyester, phenolic, melamine, epoxy, and polyurethane resins and mixtures thereof.
[0156] It can be a cold-curable or heat-curable adhesive, and the addition of a curing catalyst can be advantageous. Suitable catalysts for accelerating the complete curing of adhesives are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, Volume A18, page 469, VCH Publishing Company, Weinheim 1991.
[0157] Multilayer systems are also possible here, with the possibility of higher concentrations of stabilizers in the top layer, for example, 1 to 15 parts by weight, especially 3 to 10 parts by weight, of a 100-part solid adhesive.
[0158] Example:
[0159] The following list of embodiments is provided to further illustrate this disclosure, but is not intended to limit this disclosure to the specific embodiments listed below.
[0160] 1. A product or a salt thereof, which is obtainable by a method comprising the following steps:
[0161] a) To prepare at least one compound having formula (I) in the presence of at least one catalyst,
[0162]
[0163] Wherein G* is selected from substituted 2-(2-hydroxyphenyl)-2H-benzotriazole groups or substituted 2-hydroxyphenyl-triazine.
[0164] R 30 Selected from hydrogen, substituted or unsubstituted straight or branched C1-C 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, substituted or unsubstituted C7-C 24 Arylalkyl, substituted or unsubstituted straight or branched C1-C 24 Heteroalkyl or -S(=O)2R 31 , where R 31 C1-C selected from substituted or unsubstituted straight or branched chains 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 cycloalkyl, substituted or unsubstituted C6-C 24 aryl, or substituted or unsubstituted C7-C 24Arylalkyl;
[0165] b) Reaction with a polyether polyol, which is obtained by reacting a composition of the following:
[0166] b1) Based on 5 wt% to 90 wt% of the total amount of the polyether polyol, at least one sugar selected from C5-C6 sugar alcohols, monosaccharides, oligosaccharides, polysaccharides or mixtures thereof;
[0167] b2) At least one epoxide, comprising 5 wt% to 90 wt% of the total amount of the polyether polyol;
[0168] b3) Based on 0 wt% to 90 wt% of the total amount of the polyether polyol, at least one polyol having 2 to 4 hydroxyl groups; and
[0169] b4) Based on the total amount of the polyether polyol, at least one optional reactant selected from fatty acids, fatty acid monoesters or mixtures thereof, from 0 wt% to 15 wt%.
[0170] 2. The product or a salt thereof according to Example 2, wherein the substituted 2-hydroxyphenyl-triazine is selected from formula (A).
[0171]
[0172] Z is selected from C1-C of substituted or unsubstituted straight or branched chains. 30 Alkylene, substituted or unsubstituted straight-chain or branched 2- to 30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 24 Alkenyl, substituted or unsubstituted straight-chain or branched 3- to 30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 24 Cycloalkylene, or substituted or unsubstituted C6-C 24 Alpha-aryl
[0173] Ar1 and Ar2 are independent parts of equation (C).
[0174]
[0175] The dashed lines represent single bonds between formula (C) and the triazine ring having formula (A), and R1, R2, R3, R4, and R5 are independently selected from hydrogen, substituted or unsubstituted straight-chain or branched C1-C bonds. 24 Alkyl, substituted or unsubstituted C6-C 24 Aryl, -OH, -OC1-C 24 Alkyl group; or a part having the formula (M),
[0176]
[0177] The dashed lines represent the single bonds between formula (M) and the triazine ring having formula (A), and Z is attached to -C(=O)OR. 30 ,
[0178] R6, R7, and R8 are independently selected from hydrogen, or from substituted or unsubstituted straight-chain or branched C1-C atoms. 24 alkyl.
[0179] 3. The product or a salt thereof according to any one of Examples 1 to 2, wherein the substituted 2-(2-hydroxyphenyl)-2H-benzotriazole is selected from formula (B).
[0180]
[0181] Where R 41 and R 42 Independently selected from hydrogen, halogen, substituted or unsubstituted straight-chain or branched C1-C atoms 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, or substituted or unsubstituted C7-C 24 Arylalkyl.
[0182] 4. The product or a salt thereof according to any one of Examples 1 to 3, wherein R 30 Selected from hydrogen, substituted or unsubstituted straight or branched C1-C 24 Alkyl, substituted or unsubstituted straight or branched C1-C 24 Heteroalkyl, or substituted or unsubstituted C7-C 24 Arylalkyl.
[0183] 5. The product or salt thereof according to any one of Examples 1 to 4, wherein Z is selected from substituted or unsubstituted straight-chain or branched C1-C8 alkylene groups; R1, R2, R3, R4 and R5 are independently selected from hydrogen, unsubstituted C1-C6 alkyl, unsubstituted C6-C6 alkyl, and unsubstituted C8-C6 alkyl. 12 Aryl, -OH or -OC1-C6 alkyl; and R6, R7 and R8 are hydrogen or unsubstituted straight-chain C1-C6 alkyl.
[0184] 6. The product or a salt thereof according to any one of Examples 1 to 5, wherein R 41 and R 42 Independently selected from hydrogen, halogen, substituted or unsubstituted straight-chain or branched C1-C6 alkyl groups, or substituted or unsubstituted C7-C groups. 24 Arylalkyl.
[0185] 7. The product or salt thereof according to any one of Examples 1 to 6, wherein the compound having formula (I) is selected from methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, ethyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionate, 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionic acid, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionic acid, methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionate, ... Ethyl propionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate, octyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, 2 Ethyl [4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy]octanoate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy]butyrate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]-2-methylpropionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]octanoate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]hexanoate, methyl 2-[4- Methyl [4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl [4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl [4,6-bis(2,4-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, 6-methylheptyl [4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl [2,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, octyl [2,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate,Methyl 5-triazine-2-yl]-3-hydroxy-phenoxy]ethoxy]propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazine-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine-2-yl]phenoxy]butyrate, methyl 2-[4-[4,6-bis(4-butoxy-2-hydroxy- ... Methyl 2-[[4,6-bis(4,6-hexyloxy-2-hydroxy-3-methyl-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-2-methyl-phenoxy]propionate, methyl 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2-methyl-3-hydroxy-phenoxy]propionate, methyl 2-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate Ester, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octanoate, methyl 2-[4-[4,6-bis[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4,6-bis(4-phenylphenyl)-1,3, Ethyl 5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[4,6-bis[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]phenoxy]propionate, or combinations of two or more thereof.
[0186] 8. The product or a salt thereof according to Example 7, wherein the compound having formula (I) is selected from methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxy-phenoxy]propionate, methyl 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3- [Hydroxyphenoxy]octyl propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]propionate, methyl 2-[4-[4,6-bis[2-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]octyl propionate, methyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]propionate, methyl 2 ... 6-methylheptyl [5-triazin-2-yl]-3-hydroxyphenoxy]propionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2-methyl-3-hydroxyphenoxy]propionate, methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionate, ethyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionate, 3 -[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-phenyl]propionic acid, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionic acid, methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionic acid, ethyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxy-phenyl]propionic acid, or combinations of two or more thereof.
[0187] 9. The product or salt thereof according to any one of Examples 1 to 8, wherein the weight ratio of the compound having formula (I) to the polyether polyol is in the range of 1 to 10 to 10 to 1.
[0188] 10. The product or salt thereof according to any one of Examples 1 to 9, wherein the at least one catalyst is selected from protic acids, Sn compounds, Zr compounds, Bi compounds, Zn compounds, Al compounds, Ti compounds, or combinations of two or more thereof.
[0189] 11. The product or salt thereof according to any one of Examples 1 to 10, wherein the polyol is selected from glycerol, monopropylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, erythritol, pentaerythritol, trimethylolpropane or mixtures thereof.
[0190] 12. The product or a salt thereof according to any one of Examples 1 to 11, wherein the epoxide is selected from C2-C4. 20Epoxides, preferably C2-C6 epoxides.
[0191] 13. The product or salt thereof according to any one of Examples 1 to 12, wherein the polyether polyol has a viscosity in the range of 1,000 to 50,000 mPa·s, preferably 2,000 to 45,000 mPa·s, as measured at 25°C according to DIN EN 12092.
[0192] 14. The product or salt thereof according to any one of Examples 1 to 13, wherein the polyether polyol has an OH value in the range of 50 to 2000 mg KOH / g, preferably 100 to 1500 mg KOH / g, as measured according to DIN 53 240 (1971-12).
[0193] 15. The product or salt thereof according to any one of Examples 1 to 14, wherein the polyether polyol has an estimated weight-average molecular weight of 100 to 2500 g / mol, preferably 150 to 1000 g / mol, as determined by GPC using polystyrene as an internal standard.
[0194] 16. The product or salt thereof according to any one of Examples 1 to 15, wherein the polyether polyol has an estimated weight-average molecular weight of 150 to 1000 g / mol as determined by GPC using polystyrene as an internal standard.
[0195] 17. The product or salt thereof according to any one of Examples 1 to 16 has an estimated weight-average molecular weight in the range of 500 to 20,000, as determined by GPC using polystyrene as an internal standard.
[0196] 18. The product or salt thereof according to any one of Examples 1 to 17 has a solubility of more than 10 g / 100 mL xylene at room temperature.
[0197] 19. A method for obtaining the product or a salt thereof according to any one of Examples 1 to 18, the method comprising the following steps:
[0198] a. To make a compound having formula I;
[0199] b. With polyether polyols,
[0200] The reaction takes place in the presence of at least one catalyst.
[0201] 20. Use of the product or salt thereof according to any one of Examples 1 to 18 as a UV stabilizer.
[0202] 21. A composition comprising the product or a salt thereof according to any one of Examples 1 to 18.
[0203] 22. A method for protecting a material or coating from light, wherein the method includes the step of providing the product or a salt thereof according to any one of Examples 1 to 18 as a UV stabilizer.
[0204] The invention claimed herein is described in detail through the following non-limiting working examples. More specifically, the test methods specified below are part of the general disclosure of this application and are not limited to the specific working examples.
[0205] Example
[0206] Methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionate (BO2) is available from Alfa Chemistry, USA.
[0207] 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]-propionate methyl ester (A01), 2-[4-[4,6-bis([1,1′-phenyl]-4-yl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]-propionate methyl ester (A02), and mixtures of A01 and A02 are produced according to the procedure described in patent application WO 2022233760A1.
[0208] Dibutyltin dilaurate (DBTL) and p-toluenesulfonic acid monohydrate are available from Sigma-Aldrich, Germany.
[0209] 3405 / 1 (an oligomerization product of sucrose with propylene oxide and glycerol, having an OH value of 450 mg KOH / g) is available from BASF, Germany.
[0210] 3408 / 1 (an oligomerization product of sucrose with propylene oxide and glycerol, having an OH value of 420 mg KOH / g) is available from BASF, Germany.
[0211] 3409 / 1 (an oligomerization product of sucrose with propylene oxide and glycerol, having an OH value of 430 mg KOH / g) is available from BASF, Germany.
[0212] 3422 (an alkoxylated product of sorbitol and propylene oxide with an OH value of 490 mg KOH / g) is available from BASF, Germany.
[0213] 3423 (an oligomerization product of sucrose with propylene oxide and glycerol, having an OH value of 490 mg KOH / g) is available from BASF, Germany.
[0214] 3424 (an oligomerization product of sucrose with pentaerythritol, propylene oxide and diethylene glycol, with an OH value of 403 mg KOH / g) is available from BASF, Germany.
[0215] ME V 05 (methyl oleate) is available from BASF in Germany.
[0216] Example 1:
[0217] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring and heating block. Lupronol 3405 / 1 (14.5 g), dibutyltin dilaurate (0.075 g), and a compound having the formula BO2 (32.5 g, 0.09 mol) were transferred into the flask. The contents of the flask were heated to 180 °C under an argon atmosphere and a 20 mbar vacuum was applied. After stirring for 5.5 h, dibutyltin dilaurate (0.025 g) was added. After stirring for 15.5 h, Lupronol 3405-1 (2.01 g) was added, and after stirring for 22.0 h, Lupronol 3405-1 (2.05 g) was added. After stirring for 33.5 h, HPLC analysis indicated a conversion of >97% for the compound having the formula BO2. The contents of the flask were drained and cooled to obtain 37.3 g of a transparent brownish melt of UV-absorbing polymer.
[0218] Example 2:
[0219] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring and heating block. Lupronol 3423 (12.3 g), dibutyltin dilaurate (0.079 g), and a compound having the formula BO2 (34.6 g, 0.10 mol) were transferred into the flask. The contents of the flask were heated to 180 °C under an argon atmosphere and a 20 mbar vacuum was applied. After stirring for 5.5 h, dibutyltin dilaurate (0.026 g) was added. After stirring for 15.5 h, Lupronol 3405-1 (1.82 g) was added, and after stirring for 22.0 h, Lupronol 3405-1 (2.38 g) was added. After stirring for 33.5 h, HPLC analysis indicated that the conversion of the compound having the formula BO2 was >95%. The contents of the flask were drained and cooled to obtain 41.3 g of a transparent, orange-brown melt of UV-absorbing polymer.
[0220] Example 3:
[0221] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring and heating block. Lupronol 3423 (15.0 g), dibutyltin dilaurate (0.097 g), and a compound having the formula BO2 (31.8 g, 0.09 mol) were transferred into the flask. The contents of the flask were heated to 180 °C under an argon atmosphere and a 20 mbar vacuum was applied. After stirring for 5.5 h, dibutyltin dilaurate (0.027 g) was added. After stirring for 15.5 h, Lupronol 3405-1 (1.27 g) was added, and after stirring for 22.0 h, Lupronol 3405-1 (0.94 g) was added. After stirring for 33.5 h, HPLC analysis indicated a conversion of 98% for the compound having the formula BO2. The contents of the flask were drained and cooled to give 41.7 g of a transparent, orange-brown melt of UV-absorbing polymer.
[0222] When tin(II) ethylhexanoate was used as a catalyst, the same product was also obtained in an acceptable yield.
[0223] Example 4:
[0224] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring and heating block. Lupronol 3423 (14.5 g), Pernil ME V 05 (2.0 g), dibutyltin dilaurate (0.096 g), and a compound having the formula BO2 (30.7 g, 0.09 mol) were transferred into the flask. The contents of the flask were heated to 180 °C under an argon atmosphere and a 20 mbar vacuum was applied. After stirring for 5.5 h, dibutyltin dilaurate (0.024 g) was added. After stirring for 15.5 h, Lupronol 3405-1 (1.50 g) was added, and after stirring for 22.0 h, Lupronol 3405-1 (1.39 g) was added. After stirring for 33.5 h, HPLC analysis indicated a conversion of >97% for the compound having the formula BO2. The contents of the flask were drained and cooled to obtain 43.9 g of a transparent, orange-brown melt of UV-absorbing polymer.
[0225] Table 1: Details of Examples 1-4.
[0226]
[0227] Example 5:
[0228] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring and heating block. Lupronol 3408 / 1 (12.0 g), dibutyltin dilaurate (0.063 g), and the compound having formula BO2 (28.3 g) were transferred into the flask. The contents of the flask were heated to 180 °C under an argon atmosphere and a 20 mbar vacuum was applied. After stirring for 9 h, dibutyltin dilaurate (0.03 g) was added. After stirring for 12 h, Lupronol 3408 / 1 (1.83 g) was added, after stirring for 26 h, Lupronol 3408 / 1 (2.04 g) was added, and after stirring for 30 h, Lupronol 3408 / 1 (2.08 g) was added. After stirring for 36 h, HPLC analysis indicated a conversion of >98% for the compound having formula BO2. The contents of the flask were drained and cooled to obtain 41.8 g of a transparent brownish melt of UV-absorbing polymer.
[0229] Examples 6-11 were produced in the same manner as described in Example 5. Table 2 indicates the amounts of compound BO2 and the polyether polyol, as well as the reaction time and the yield of the product.
[0230] Table 2: Details of Example 5-11
[0231]
[0232] Example 11 was also obtained in acceptable yields when zirconium neodecanoate (TIB KAT 818, TIB Chemicals, Germany), aluminum triisopropoxide, or bismuth neodecanoate (TIB KAT 716, TIB Chemicals, Germany) were used as catalysts instead of dibutyltin dilaurate.
[0233] Table 3 lists the absorbance, GPC, and solubility data.
[0234]
[0235] *Mw GPC—Weight-average molecular weight of the product, estimated by GPC using styrene as a standard.
[0236] Example 12:
[0237] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring and heating block. Lupronol 3408 / 1 (4.6 g), dibutyltin dilaurate (0.075 g), and the compound having formula A01 (2.0 g) were transferred into the flask. The contents of the flask were heated to 200 °C under an argon atmosphere and a 20 mbar vacuum was applied. Additional amounts of the compound having formula A01 were added after stirring for 4 h (2.0 g) and after stirring for 8 h (2.0 g). After stirring for 15 h, HPLC analysis indicated a conversion of 96.6% for the compound having formula A01. The contents of the flask were drained and cooled to give 8.4 g of a transparent brownish melt of UV-absorbing polymer.
[0238] Example 13:
[0239] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring heating block. Lupronol 3409 / 1 (8.6 g), dibutyltin dilaurate (0.1 g), and a compound having the formula A02 (2.0 g) were transferred into the flask. The contents of the flask were heated to 200 °C under an argon atmosphere and a 20 mbar vacuum was applied. Additional amounts of the compound having the formula A02 were added after stirring for 4 h (2.0 g) and after stirring for 8 h (2.0 g). After stirring for 21 h, the contents of the flask were drained and cooled to obtain 12.5 g of a transparent brownish melt of UV-absorbing polymer.
[0240] Example 14:
[0241] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring heating block. Lupronol 3422 (6.2 g), dibutyltin dilaurate (0.1 g), and a compound having the formula A02 (2.0 g) were transferred into the flask. The contents of the flask were heated to 200 °C under an argon atmosphere and a 20 mbar vacuum was applied. Additional amounts of the compound having the formula A02 were added after stirring for 4 h (2.0 g) and after stirring for 8 h (2.0 g). After stirring for 21 h, the contents of the flask were drained and cooled to obtain 10.2 g of a transparent orange melt of a UV-absorbing polymer.
[0242] Example 15:
[0243] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring heating block. Lupronol 3422 (3.6 g), dibutyltin dilaurate (0.2 g), and a mixture (4 g) containing a compound having formula A01 (44%) and a compound having formula A02 (54%) were transferred into the flask. The contents of the flask were heated to 200 °C under an argon atmosphere and a 20 mbar vacuum was applied. Additional amounts of Lupronol 3422 were added after stirring for 10 h (2.1 g) and after stirring for 15 h (3.7 g). After stirring for 21 h, the contents of the flask were drained and cooled to obtain 12.3 g of a transparent brownish melt of UV-absorbing polymer.
[0244] Example 16:
[0245] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring heating block. 3.2 g of Lupronol 3423, 0.2 g of dibutyltin dilaurate, and 4 g of a mixture containing 44% of a compound having formula A01 and 54% of a compound having formula A02 were transferred into the flask. The contents of the flask were heated to 200 °C under an argon atmosphere and a 20 mbar vacuum was applied. Additional amounts of Lupronol 3422 were added after stirring for 10 h (1.34 g) and after stirring for 15 h (1.7 g). After stirring for 21 h, the contents of the flask were drained and cooled to obtain 9.4 g of a transparent brownish melt of UV-absorbing polymer.
[0246] Example 17:
[0247] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring heating block. 5.1 g of Lupronol 3424, 0.2 g of dibutyltin dilaurate, and 4 g of a mixture containing a compound having formula A01 (44%) and a compound having formula A02 (54%) were transferred into the flask. The contents of the flask were heated to 200 °C under an argon atmosphere and a 20 mbar vacuum was applied. Additional amounts of Lupronol 3424 were added after stirring for 10 h (0.9 g) and after stirring for 15 h (3.6 g). After stirring for 21 h, the contents of the flask were drained and cooled to obtain 21.1 g of a transparent brownish melt of UV-absorbing polymer.
[0248] Example 18:
[0249] A 100 mL glass flask equipped with a magnetic stir bar was placed in a stirring and heating block. The compound having formula BO1 (7.6 g), Lupronol 3424 (2.20 g), p-toluenesulfonic acid monohydrate (0.08 g), and toluene (20 g) were transferred into the flask. The contents of the flask were heated under reflux under an argon flow. Additional amounts of Lupronol 3424 were added after stirring for 4 h (0.5 g) and after stirring for 5 h (1.0 g). After stirring for 7 h, HPLC analysis indicated a conversion of 97% for the compound having formula BO1. The contents of the flask were drained and cooled to give 8.0 g of a viscous yellow liquid UV-absorbing polymer.
[0250] Table 4 summarizes the absorbance, GPC, and solubility data for Examples 12-18.
[0251]
[0252] *Mw GPC—Weight-average molecular weight of the product, estimated by GPC using styrene as a standard.
[0253] As can be observed from Tables 1, 3 and 4, the obtained product exhibits significantly high xylene solubility, while the incorporation of bio-associated sugars improves the environmental impact of the UV absorber.
[0254] Application testing:
[0255] The products of this invention can be used as UV stabilizers and have been tested in thermosetting acrylic clear coatings having the following compositions (as described in Examples 1-4 above):
[0256]
[0257] 1) Acrylic resin (60% solution in xylene / butanol 26:9); Allnex
[0258] 2) Acrylic resin (in Solvesso 150) 4) (75% solution); Zhanxin Company
[0259] 3) Melamine resin (55% solution in isobutanol); Ineosmelamines
[0260] 4) Aromatic hydrocarbon mixture, boiling point range 182℃-203℃; ExxonMobil Chemical.
[0261] 5) 1% of Solvesso 150 4) Borchers (China)
[0262] The solids content of the composition is 53%.
[0263] The products of the present invention to be tested (UV stabilizers) (Examples 1-4 described above) were added to the clear coating in the amounts shown in Table 5 based on the coating solids content. Different dosage levels were required due to the varying UV-absorbing chromophore content in the test compounds, and adjustments were necessary to evaluate the stabilizing effect. The coating formulation was additionally mixed with 1% by weight of a co-stabilizer (compound z) (Tinuvin 123) having the following formula, based on the coating solids content.
[0264]
[0265] A transparent coating is applied to a white roll-coated panel to produce a dry film thickness of approximately 40 μm after curing (at 130°C for 30 minutes).
[0266] The coated panels were subjected to artificial aging cycles in an Xe-WOM aging apparatus from Atlas Corp., according to SAE-J2527. After a certain exposure time, gloss was measured at 20°C, and then exposure was continued. The retained gloss is an indicator of the UV stabilizing effect of the tested UV absorber in the coating film; lower gloss indicates more surface degradation.
[0267] Table 5: Accelerated aging results: Gloss (20°) after x exposure time (hours)
[0268]
[0269] *Not measured due to intense crack formation; #Amount relative to solids content in wt.-%
[0270] Blank samples (without any stabilizer) revealed severe degradation of the coating film due to insufficient stability. The UV stability characteristics, indicated by the gloss of the product of the claimed invention, are compared with standards. 1130 or 384-2 is comparable.
Claims
1. A product or a salt thereof, which is obtainable by a method comprising the following steps: a) To prepare at least one compound having formula (I) in the presence of at least one catalyst, Wherein G* is selected from substituted 2-(2-hydroxyphenyl)-2H-benzotriazole groups or substituted 2-hydroxyphenyl-triazine. R 30 Selected from hydrogen, substituted or unsubstituted straight or branched C1-C 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, substituted or unsubstituted C7-C 24 Arylalkyl, substituted or unsubstituted straight or branched C1-C 24 Heteroalkyl or -S(=O)2R 31 , where R 31 C1-C selected from substituted or unsubstituted straight or branched chains 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 cycloalkyl, substituted or unsubstituted C6-C 24 aryl, or substituted or unsubstituted C7-C 24 Arylalkyl; b) Reaction with a polyether polyol, which is obtained by reacting a composition of the following: b1) Based on 5 wt% to 90 wt% of the total amount of the polyether polyol, at least one sugar selected from C5-C6 sugar alcohols, monosaccharides, oligosaccharides, polysaccharides or mixtures thereof; b2) At least one epoxide, comprising 5 wt% to 90 wt% of the total amount of the polyether polyol; b3) Based on 0 wt% to 90 wt% of the total amount of the polyether polyol, at least one polyol having 2 to 4 hydroxyl groups; and b4) Based on the total amount of the polyether polyol, at least one optional reactant selected from fatty acids, fatty acid monoesters or mixtures thereof, from 0 wt% to 15 wt%.
2. The product or a salt thereof according to claim 1, wherein, The substituted 2-hydroxyphenyl-triazine is selected from formula (A). Z is selected from C1-C of substituted or unsubstituted straight or branched chains. 30 Alkylene, substituted or unsubstituted straight-chain or branched 2- to 30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 24 Alkenyl, substituted or unsubstituted straight-chain or branched 3- to 30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 24 Cycloalkylene, or substituted or unsubstituted C6-C 24 Alpha-aryl Ar1 and Ar2 are independent parts of equation (C). The dashed lines represent single bonds between formula (C) and the triazine ring having formula (A), and R1, R2, R3, R4, and R5 are independently selected from hydrogen, substituted or unsubstituted straight-chain or branched C1-C bonds. 24 Alkyl, substituted or unsubstituted C6-C 24 Aryl, -OH, -OC1-C 24 Alkyl group; or a part having the formula (M), The dashed lines represent the single bonds between formula (M) and the triazine ring having formula (A), and Z is attached to -C(=O)OR. 30 , R6, R7, and R8 are independently selected from hydrogen, or from substituted or unsubstituted straight-chain or branched C1-C atoms. 24 alkyl.
3. The product or salt thereof according to any one of claims 1 to 2, wherein, The substituted 2-(2-hydroxyphenyl)-2H-benzotriazole is selected from formula (B). Where R 41 and R 42 Independently selected from hydrogen, halogen, substituted or unsubstituted straight-chain or branched C1-C atoms 24 Alkyl, substituted or unsubstituted straight or branched C2-C 24 alkenyl, substituted or unsubstituted C5-C 24 Cycloalkyl, substituted or unsubstituted C5-C 24 Cycloalkenyl, substituted or unsubstituted C6-C 24 aryl, or substituted or unsubstituted C7-C 24 Arylalkyl.
4. The product or a salt thereof according to any one of claims 1 to 3, wherein, Z is selected from substituted or unsubstituted straight-chain or branched C1-C8 alkylene groups; R1, R2, R3, R4, and R5 are independently selected from hydrogen, unsubstituted C1-C6 alkyl, and unsubstituted C6-C6 alkyl. 12 Aryl, -OH or -OC1-C6 alkyl; and R6, R7 and R8 are hydrogen.
5. The product or a salt thereof according to any one of claims 1 to 4, wherein, R 41 and R 42 They are independently selected from hydrogen, halogens, substituted or unsubstituted straight-chain or branched C1-C6 alkyl groups.
6. The product or a salt thereof according to any one of claims 1 to 5, wherein, The compound having formula (I) is selected from methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionate, ethyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionate, 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propionate, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionate, methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionate, ethyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propionate, and 2-[4-[4,6-bis(2,4-dimethylphenyl]propionate]propionate. Methyl propionate of 2-[4-[4,6-bis(4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy], methyl propionate of 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy], octyl propionate of 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy], ethyl propionate of 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy], ethyl propionate of 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy], ethyl propionate of 2-[4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy] [4-[4,6-diphenyl-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]methyl butyrate, 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-2-methylpropionate, 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]methyl octanoate, 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]methyl octanoate, 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]methyl hexanoate, 2-[4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]methyl hexanoate Methyl propionate of 2-[4-[4,6-bis[2-hydroxy-4-(1-methyl-2-octyloxy-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octyl propionate, 6-methylheptyl propionate of 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]octyl propionate, methyl propionate of 2-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]ethoxy], methyl propionate of 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]ethoxy]Methyl 6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]-3-butoxy-propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]phenoxy]butyrate, methyl 2-[4-[4,6-bis(4-butoxy-2-hydroxy-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]propionate, methyl 2-[4-[ Methyl 4,6-bis(4-hexyloxy-2-hydroxy-3-methyl-phenyl)-1,3,5-triazin-2-yl]-3-hydroxy-2-methyl-phenoxy]propionate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2-methyl-3-hydroxy-phenoxy]propionate, ethyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate ... Methyl octanoate of [phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy], methyl 2-[4-[4,6-bis[2-hydroxy-4-(1-methoxycarbonylpropoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-3-hydroxy-phenoxy]butyrate, methyl 2-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl] Ethyl 3-hydroxyphenoxy]propionate, methyl 2-[4-[4,6-bis[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]propionate, methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(2-methoxy-1-methyl-2-oxo-ethoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]phenoxy]propionate, or combinations of two or more thereof.
7. The product or a salt thereof according to any one of claims 1 to 6, wherein, The weight ratio of the compound having formula (I) to the polyether polyol is in the range of 1:10 to 10:
1.
8. The product or a salt thereof according to any one of claims 1 to 7, wherein, The catalyst is selected from protic acids, Sn compounds, Zr compounds, Bi compounds, Zn compounds, Al compounds, Ti compounds, or combinations of two or more thereof.
9. The product or a salt thereof according to any one of claims 1 to 8, wherein, The polyol is selected from glycerol, monopropylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, erythritol, pentaerythritol, trimethylolpropane or mixtures thereof.
10. The product or a salt thereof according to any one of claims 1 to 9, wherein, The epoxide is selected from C2-C. 20 Epoxides, preferably C2-C6 epoxides.
11. The product or a salt thereof according to any one of claims 1 to 10, wherein, The polyether polyol has an OH value in the range of 50 to 2000 mg KOH / g.
12. The product or a salt thereof according to any one of claims 1 to 11, wherein, The polyether polyol has an estimated weight-average molecular weight of 100 to 2500 g / mol, determined by GPC using polystyrene as an internal standard.
13. The product or salt thereof according to any one of claims 1 to 12, having an estimated weight-average molecular weight in the range of 500 to 20,000 as determined by GPC using polystyrene as an internal standard.
14. A method for obtaining the product or a salt thereof according to any one of claims 1 to 13, the method comprising the following steps: a. To make the compound having formula I; b. With the polyether polyol, The reaction takes place in the presence of at least one catalyst.
15. Use of the product or salt thereof according to any one of claims 1 to 13 as a UV stabilizer.
16. A composition comprising the product or a salt thereof according to any one of claims 1 to 13.
17. A method for protecting a material or coating from light, wherein the method comprises the step of providing the product or a salt thereof according to any one of claims 1 to 13 as a UV stabilizer.
Citation Information
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