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Weakly Basic Hindered Amines Having Carbonate Skeletons, Synthetic Resin Compositions, And Coating Compositions

a technology of hindered amines and carbonates, which is applied in the field of weakly basic hindered amine compounds having carbonate skeletons, can solve the problems of low compatibility, inability to sustain the stabilization effect, and extraction by acid rain, and achieves long-term stabilization and superior resistance to acid rain extraction

Inactive Publication Date: 2009-04-30
ADEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010]The present invention therefore proposes a hindered amine compound which confers long-term stabilization on synthetic resins, and which shows superior resistance to extraction by acid rain or chemicals.
[0011]The Inventors, as a result of extensive research carried out to resolve this problem, found that the hindered amine compound having a carbonate structure represented with by the general formula (I) or (II) gave excellent long-term stabilization of a synthetic resin, and thereby arrived at the present invention.

Problems solved by technology

For example, prior art hindered amine compounds, when used with polyolefin resins, had low compatibility with the resin, and since they vaporized from the resin, they had the problem that their stabilization effect did not endure.
Moreover, in applications where they came in contact with acid rain and agricultural chemicals, there was also the problem that they were extracted by the acid.
However, there is neither any disclosure nor suggestion of weakly basic hindered amine compounds having an alkyloxyamine structure.
However, there is neither any disclosure nor suggestion of weakly basic hindered amine compounds having a carbonate structure.

Method used

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  • Weakly Basic Hindered Amines Having Carbonate Skeletons, Synthetic Resin Compositions, And Coating Compositions
  • Weakly Basic Hindered Amines Having Carbonate Skeletons, Synthetic Resin Compositions, And Coating Compositions
  • Weakly Basic Hindered Amines Having Carbonate Skeletons, Synthetic Resin Compositions, And Coating Compositions

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Compound No. 1

[0071]17.0 g (98.1 mmol) of 4-hydroxy-1-oxy-2,2,6,6-tetramethyl piperidine was dissolved in 40.0 g of chlorobenzene, and a solution containing 31.3 g (78.5 mmol) dilauroyl peroxide dissolved in 125 g chlorobenzene was dripped in at 70° C. over 3 hours. The reaction was performed at this temperature for a further 6 hours. The obtained reaction liquid was analyzed by gas chromatography to verify consumption of the starting materials. The obtained reaction liquid was a mixture of 4-hydroxy-1-undecanoxy-2,2,6,6-tetramethyl piperidine, 1-undecanoxy-2,2,6,6-tetramethyl piperidine-4-one, lauric acid and a solvent. 50 g of hexane was added to the reaction liquor, the reaction liquor was washed with 53.9 g (98 mmol) of 7.3% sodium hydroxide aqueous solution and 25 g methanol, washed twice more with 30 g water, and lauric acid was removed. The mixture was dried with anhydrous magnesium sullfate, the magnesium sulfate was removed by filtration, and the solvent was re...

example 2

Synthesis of Compound No. 7

[0074](Synthesis of 1-undecaneoxy-2,2,6,6-tetramethyl piperidine-4-one)

[0075]15.0 g (86.6 mmol) of 4-hydroxy-1-oxy-2,2,6,6-tetramethyl piperidine was dissolved in 40.0 g of chlorobenzene, and a solution containing 27.6 g (69.3 mmol) dilauroyl peroxide dissolved in 125 g chlorobenzene was dripped in at 70° C. over 3 hours. The reaction was performed at this temperature for a further 6 hours. The obtained reaction liquid was analyzed by gas chromatography to verify consumption of the starting materials. 0.1 g of 4-acetyl-1-oxy-2,2,6,6-tetramethyl piperidine was added to the reaction liquor to suppress decomposition reactions, the mixture was cooled to 0° C., and 48.3 g (64.9 mmol) of 10% sodium hypochlorite aqueous solution was dripped in over 3 hours. The reaction was continued for 3 hours at the same temperature, 15 ml of 15 wt % sodium thiosulfate aqueous solution was added, and the mixture was heated to 40° C. and reacted for 1 hour. The organic layer an...

example 3

Synthesis of Compound No. 11

[0080]8.0 g (20 mmol) of the 1,5-dioxa-9-aza-3-hydroxy-8,8,10,10-tetramethyl-9-undecyloxyspiro[5.5]und ecane obtained in Synthesis Example 2, 2.35 g (11.0 mmol) diphenyl carbonate and 0.7 g potassium carbonate were dispersed in 100 ml mineral spirit, reacted at 170-180° C. for 8 hours, and phenol was removed. The mixture was cooled to 40° C., and washed 3 times with 30 ml water. Water was removed under reduced pressure with reflux at 60° C., and the solvent was removed under reduced pressure on the evaporator. The concentrate was recrystallized from ethanol by cooling to 0° C., and Compound No. 11 of purity 99.9% was obtained as colorless crystals with a melting point of 87.4° C. (yield 68.4%).

[0081]The analysis result of the obtained compound No. 11 is shown below.

IR spectrum

2850-2920 cm−1, 1750 cm−1, 1470 cm−1, 1360 cm−1, 1280 cm−1, 1230 cm−1, 1200 cm−1, 1100 cm−1, 1030 cm−1, 960 cm−1.

1H-NMR spectrum (H: Actual measurement of number of protons, figures ...

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Abstract

Hindered amines represented by the general formula (I): (wherein R is an alkyl or hydroxyalkyl group having 1 to 30 carbon atoms or alkenyl having 2 to 30 carbon atoms; n is an integer of 1 to 4; when n is 1, R1 is alkyl having 1 to 22 carbon atoms, alkenyl having 2 to 22 carbon atoms, or a group represented by the general formula (III): (R is as defined above), while when n is 2 to 4, R1 is an n-valent organic group having 2 to 20 carbon atoms). When added to synthetic resins or coating materials, the amines can impart long-period stabilizing effect to the resins or the materials and exhibit excellent resistance to extraction with acid rain or chemicals.

Description

FIELD OF THE INVENTION[0001]The present invention relates to weakly basic hindered amine compounds having carbonate skeletons.BACKGROUND ART[0002]Hindered amine compounds are known to suppress the photodegradation of organic substances such as synthetic resins, and since the stabilization effect is different depending on the structure of the amine and the environment in which it is used, amines with active hydrogen atoms, amines without active hydrogen atoms and alkyloxyamines which are even more weakly basic than tertiary amines, have been considered for this purpose. The idea of introducing a triazine skeleton in order to enhance compatibility with the synthetic resin to be stabilized or its extraction resistance, has also been considered.[0003]For example, prior art hindered amine compounds, when used with polyolefin resins, had low compatibility with the resin, and since they vaporized from the resin, they had the problem that their stabilization effect did not endure. Moreover,...

Claims

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Application Information

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IPC IPC(8): A01N25/10C07D211/06C07D491/10C08K5/3492A01P21/00C08K5/3462C08K5/3435C07D211/94C07D491/113C07D519/00C08K5/357
CPCC08K5/3435C07D211/94C07D401/12
Inventor NEGISHI, YOSHINORIAYABE, TAKASHITOBITA, ETSUO
Owner ADEKA CORP
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