JPH11279150A - Slightly eluting photostabilizer - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new hindered amine compound useful as a slightly eluting photostabilizer for films, sheets and plastic products used outdoors by converting an extremely water-soluble hindered amine compound into the slightly water-soluble compound. SOLUTION: A compound of formula I [R1 is a group of formula II or III (R3 is H or a halogen); R2 is H or methyl; X is O or NH]. For example, a compound of formula IV. The compound of formula I is obtained by integrating 2,2,6,6-tetramethylpiperidine skeleton as a highly water-soluble hindered amine with a water-insoluble 2-hydroxybenzophenone or 2-(2'-hydroxyphenyl)- benzotriazole through 2-hydroxypropyl propionate.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention provides a hard-eluting light stabilizer for films, sheets and plastic products which are exposed to the weather outdoors.

[0002]

2. Description of the Related Art A hindered amine-based light stabilizer is used together with an ultraviolet absorber to prevent deterioration of a substrate due to light in plastic products, films and sheets used outdoors. However, hindered amine compounds have a very high solubility in water due to their strong basicity, and are therefore eluted from plastic products, films, sheets, etc. by rain or absorbed by water.
The effect often decreases dramatically. Hitherto, attempts have been made to increase the molecular weight to prevent this phenomenon, and molecular weights of up to several thousand have been revealed, but the water solubility and hygroscopicity have not been improved.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to make a very water-soluble hindered amine compound less soluble in water so as to prevent elution from a plastic product used outdoors.

[0004]

Means for Solving the Problems A 2,2,6,6-tetramethylpiperidine skeleton as a highly water-soluble hindered amine, and a water-insoluble 2-hydroxybenzophenone or 2- (2'-hydroxyphenyl) -benzo Provided is a novel hindered amine compound represented by the following general formula, wherein triazole is integrated via 2-hydroxypropylpropionate.

[0005]

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However, R1 means any of the following groups (Chemical Formulas 2 and 3).

[0007]

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[0008]

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R2 represents hydrogen or a methyl group, R3 represents hydrogen or a halogen, and X represents -O- or -NH-.

Examples of compounds belonging to these include the following chemical formulas (4), (5), (6), (7) and (8).
It is not limited to these.

[0011]

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[0012]

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[0013]

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[0014]

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[0015]

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[0016]

The compounds of the present invention are described below by way of examples. Example 1 Synthesis of Chemical Formula 4 In a 300 ml flask, 42.8 g (0.3 mol) of glycidyl methacrylate (manufactured by NOF Corporation, purity: 98.8%), 2,4-dihydroxybenzophenone (manufactured by Kyodo Yakuhin). 2 g (0.3 mol) and 0.5 g of caustic potash pellets were charged, and the mixture was stirred and heated under a nitrogen stream.
The reaction was carried out for a time to obtain a pale orange liquid. 4-amino-
46.8 g (0.3 mol) of 2,2,6,6-tetramethylpiperidine (manufactured by Huls) was added, and the mixture was kept at 95 ° C for 2 hours, and then heated to 130 ° C and kept for 2 hours. 80
Cool to room temperature, then pour into tray, cool to room temperature,
Solidified and pulverized. 151 g of yellow powder (yield: 9 of theory)
8.7%) melting point 75-80 ° C, insoluble in water.

Example 2 Synthesis of Chemical Formula 7 In a 300 ml flask, 130.8 g (0.5 mol) of 2- (2 ′, 4′-dihydroxyphenyl) -5-chloro-benzotriazole (manufactured by Kyodo Yakuhin), 79 g of glycidyl methacrylate (manufactured by NOF Corporation, purity: 98.8%)
(0.56 mol) and 0.8 g of caustic soda, and reacted at 85 ° C. for 3 hours under a nitrogen stream, cooled to 70 ° C., slurried with 100 ml of methanol, filtered and dried to give 2- [2 ′ -Hydroxy-4 '-(3 "-methacryloyloxy-2" -hydroxypropoxy) -phenyl] -5-chlorobenzotriazole (115 g) was obtained as a pale yellow powder. Melting point 99-103 ° C (Yield: 5 of theory)
Next, 40.3 g (0.1 mol) of this pale yellow powder and 4-
15.6 g (0.1 mol) of amino-2,2,6,6-tetramethylpiperidine (manufactured by Huls) and 60 g of methanol were charged into a 300 ml flask and reacted at 60 ° C. for 4 hours. After cooling to room temperature, the precipitated yellow crystals were filtered and dried to obtain 55 g of a pale yellow powder (yield: 98.
4%). Melting point 162-165 ° C, water insoluble.

[0018]

According to the present invention, there is provided a hardly-eluting light stabilizer for films, sheets and plastic products which are exposed to the weather outdoors.

Continued on the front page (51) Int.Cl. ⁶ Identification code FI C08L 101/00 C08L 101/00

Claims (1)

[Claims] 1. A hindered amine compound represented by the following general formula: Embedded image However, R1 means any of the following groups (Chemical Formula 2, Chemical Formula 3). Embedded image Embedded image R2 represents hydrogen or a methyl group; R3 represents hydrogen or a halogen; and X represents -O- or -NH-.