CN101665457A - Light stabilizer bis(2,2,6,6-tetramethyl-4-piperidinyl)sebacate and preparation method thereof - Google Patents
Light stabilizer bis(2,2,6,6-tetramethyl-4-piperidinyl)sebacate and preparation method thereof Download PDFInfo
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- CN101665457A CN101665457A CN200910036230A CN200910036230A CN101665457A CN 101665457 A CN101665457 A CN 101665457A CN 200910036230 A CN200910036230 A CN 200910036230A CN 200910036230 A CN200910036230 A CN 200910036230A CN 101665457 A CN101665457 A CN 101665457A
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Abstract
The invention discloses a light stabilizer bis(2,2,6,6-tetramethyl-4-piperidinyl)sebacate and a preparation method thereof. Dimethyl sebacate and 2,2,6,6-tetramethyl-4-hydroxypiperidine are taken as raw materials, and then the raw materials react in the presence of catalyst to prepare bis(2,2,6,6-tetramethyl-4-piperidinyl)sebacate. The invention uses dimethyl sebacate and 2,2,6,6-tetramethyl-4-hydroxypiperidine as the raw materials to synthesize the bis(2,2,6,6-tetramethyl-4-piperidinyl)sebacate and adopts dibutyltin oxide as the catalyst, and thereby the separation and purification process issimplified, the reaction time is short, and the product yield is as high as more than 97 percent; the obtained product has high purity, reduced energy consumption, little environmental pollution andlow cost, and therefore, the invention is an ideal process for realizing industrial production.
Description
Technical field:
The present invention relates to a kind of photostabilizer sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester and production method thereof.
Background technology:
Sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester is the hindered amine type light stabilizer of lower molecular weight high-efficiency low-toxicity, can prolong the duration of service that various plastic cement and coating shine out of doors.In use, the course of processing, can not produce smell with polymer, can not influence the original color of material yet.Product is not volatile during high temperature process.Good with most of industrial solvent intermiscibilities, has superior polymer intermiscibility, be applicable to polypropylene, vinyon and fibre product, significant anti-photooxidation (sun-proof) effect that wears out is arranged, particularly the resistance to weathering to polypropylene and high density polyethylene(HDPE) can be superior far beyond general UV light absorber and quencher (nickel chromium triangle compound), is particularly useful for thick product, and is different with traditional ultraviolet absorbers, its effect and products thickness are irrelevant, therefore also are suitable for the product of high-specific surface area.Its advantage is its high efficiency, and simultaneously it and resin have good consistency and dispersiveness.In addition, plastics such as p-poly-phenyl ethene, HIPS, ABS resin and urethane are also effective, can be used for polypropylene, impact-resistant modified polypropylene (TPO), EPDM, polystyrene, impact-resistant polystyrene, ABS, SAN, ASA, also can be used for urethane, polymeric amide, polyacetal etc., its light stabilising effect is good.
Its chemical name is: sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester;
Molecular formula: C
28H
52O
4N
2Molecular weight: 480.5
Molecular structural formula:
Physico-chemical property: outward appearance is a white crystalline powder, fusing point mp:82-84 ℃.
At present, preparation sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) the ester synthetic method is by dimethyl sebacate and 2,2,6,6-tetramethyl--4-hydroxy piperidine is a raw material, with the sodium methylate is to carry out transesterification reaction under the condition of catalyzer, because the sodium methoxide catalyst instability, solvability is little, dangerous big, the contaminated wastewater that aftertreatment produces is big, is not suitable for suitability for industrialized production.According to reported in literature, adopt Lewis acid, alkali etc. for catalyzer carries out transesterification reaction, the catalyzer corrosive equipment, the pollution that aftertreatment produces is big, poor product quality.Adopt the solid acid catalyst catalyzed transesterification, little though product and catalyzer are easily separated to the corrodibility of equipment, the recyclable utilization of catalyzer, selectivity and active low.
Summary of the invention:
The object of the present invention is to provide the high photostabilizer sebacic acid two of a kind of product yield (2,2,6,6-tetramethyl--4-piperidyl) ester and production method thereof.
Technical solution of the present invention is:
A kind of photostabilizer sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester and production method thereof, it is characterized in that: be with dimethylbenzene, dimethyl sebacate, 2,2,6,6-tetramethyl--4-hydroxy piperidine is a raw material, reaction makes sebacic acid two (2 under the condition that catalyzer exists, 2,6,6-tetramethyl--4-piperidyl) ester; Described catalyzer is a Dibutyltin oxide.
Dimethylbenzene, dimethyl sebacate, 2,2,6,6-tetramethyl--4-hydroxy piperidine, catalyst consumption ratio are by mass: dimethyl sebacate: dimethylbenzene: 2,2,6,6-tetramethyl--4-hydroxy piperidine: catalyzer=1: 1.3～2.6: 1.3～2.0: 0.01～0.1.
With dimethylbenzene, dimethyl sebacate, 2,2,6,6-tetramethyl--4-hydroxy piperidine is a raw material, reacts under the condition that catalyzer exists, and reaction is filtered, washed after finishing, and tells organic layer; Dewater, decolour in the solution after telling organic layer, the organic layer that obtains lower the temperature cooling, crystallization, filter sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester.The temperature of described reaction is that 110～130 ℃, reaction times are 6h.
The present invention's dimethylbenzene, dimethyl sebacate, 2,2,6,6-tetramethyl--4-hydroxy piperidine is a raw material synthesis of sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester adopts the Dibutyltin oxide catalyzer, has simplified the separation purification process, reaction times is short, and the product yield height reaches more than 97% the yield of product, it is higher to obtain product purity, and energy consumption reduces, and environmental pollution is little, cost is low, is the comparatively ideal technology that realizes suitability for industrialized production.
The invention will be further described below in conjunction with embodiment:
Embodiment:
Embodiment 1:
In the four-hole boiling flask of the 250mL that thermometer is housed, add dimethylbenzene 40g, dimethyl sebacate 23.0g (0.1mol), 2,2,6,6-tetramethyl--4-hydroxy piperidine 33.03g (0.21mol), catalyzer 1g, this catalyzer is a Dibutyltin oxide, loads onto prolong, start agitator, when being warming up to 110-130 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 6h (using the liquid chromatography monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, crystallization, filters and promptly gets white crystalline powder sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester, and product yield is 97.85%.
Embodiment 2:
In the four-hole boiling flask of the 250mL that thermometer is housed, add dimethylbenzene 40g, dimethyl sebacate 23.0g (0.1mol), 2,2,6,6-tetramethyl--4-hydroxy piperidine 33.03g (0.21mol), catalyzer 1.2g, this catalyzer is a Dibutyltin oxide, loads onto prolong, start agitator, when being warming up to 110-130 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 6h (using the liquid chromatography monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, crystallization, filters and promptly gets white crystalline powder sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester, and product yield is 98.06%.
Embodiment 3:
In the four-hole boiling flask of the 250mL that thermometer is housed, add dimethylbenzene 40g, dimethyl sebacate 23.0g (0.1mol), 2,2,6,6-tetramethyl--4-hydroxy piperidine 33.82g (0.215mol), catalyzer 1.0g, this catalyzer is a Dibutyltin oxide, loads onto prolong, start agitator, when being warming up to 110-130 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 6h (using the liquid chromatography monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, crystallization, filters and promptly gets white crystalline powder sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester, and product yield is 98.05%.
Embodiment 4:
In the four-hole boiling flask of the 250mL that thermometer is housed, add dimethylbenzene 40g, dimethyl sebacate 23.0g (0.1mol), 2,2,6,6-tetramethyl--4-hydroxy piperidine 31.46g (0.2mol), catalyzer 1.0g, this catalyzer is a Dibutyltin oxide, loads onto prolong, start agitator, when being warming up to 110-130 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 6h (using the liquid chromatography monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, crystallization, filters and promptly gets white crystalline powder sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester, and product yield is 97.56%.
Embodiment 5:
In the four-hole boiling flask of the 250mL that thermometer is housed, add dimethylbenzene 40g, dimethyl sebacate 23.0g (0.1mol), 2,2,6,6-tetramethyl--4-hydroxy piperidine 32.25g (0.205mol), catalyzer 1.0g, this catalyzer is a Dibutyltin oxide, loads onto prolong, start agitator, when being warming up to 110-130 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 6h (using the liquid chromatography monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, crystallization, filters and promptly gets white crystalline powder sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester, and product yield is 97.81%.
Claims (5)
1, a kind of photostabilizer sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester, it is characterized in that: be with dimethylbenzene, dimethyl sebacate, 2,2,6,6-tetramethyl--4-hydroxy piperidine is a raw material, reaction makes sebacic acid two (2,2,6 under the condition that catalyzer exists, 6-tetramethyl--4-piperidyl) ester, described catalyzer is a Dibutyltin oxide.
2, according to claim 1 described-kind of photostabilizer sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester, it is characterized in that: dimethylbenzene, dimethyl sebacate, 2,2,6,6-tetramethyl--4-hydroxy piperidine, catalyst consumption ratio are by mass: dimethyl sebacate: dimethylbenzene: 2,2,6,6-tetramethyl--4-hydroxy piperidine: catalyzer=1: 1.3～2.6: 1.3～2.0: 0.01～0.1.
3, a kind of photostabilizer sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) production method of ester, it is characterized in that: with dimethylbenzene, dimethyl sebacate, 2,2,6,6-tetramethyl--4-hydroxy piperidine is a raw material, react under the condition that catalyzer exists, described catalyzer is a Dibutyltin oxide, after reaction finishes, filter, wash, tell organic layer; Dewater, decolour in the solution after telling organic layer, the organic layer that obtains lower the temperature cooling, crystallization, filter sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester.
4, according to the described a kind of photostabilizer sebacic acid two (2 of claim 3,2,6,6-tetramethyl--4-piperidyl) production method of ester is characterized in that: dimethylbenzene, dimethyl sebacate, 2,2,6,6-tetramethyl--4-hydroxy piperidine, catalyst consumption ratio are by mass: dimethyl sebacate: dimethylbenzene: 2,2,6,6-tetramethyl--4-hydroxy piperidine: catalyzer=1: 1.3～2.6: 1.3～2.0: 0.01～0.1.
5, according to the production method of claim 3 or 4 described a kind of photostabilizer sebacic acid two (2,2,6,6-tetramethyl--4-piperidyl) ester, it is characterized in that: the temperature of described reaction is that 110～130 ℃, reaction times are 6h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110396060A (en) * | 2019-07-12 | 2019-11-01 | 西安工业大学 | A kind of light stabilizer and preparation method thereof containing double hindered piperidine bases |
| CN110938233A (en) * | 2019-11-07 | 2020-03-31 | 宿迁联盛科技股份有限公司 | Hindered amine light stabilizer for nylon and preparation method thereof |
| CN114230511A (en) * | 2021-12-31 | 2022-03-25 | 利安隆凯亚(河北)新材料有限公司 | Preparation method of bis (2,2,6, 6-tetramethyl-4-piperidyl) sebacate |
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2009
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110396060A (en) * | 2019-07-12 | 2019-11-01 | 西安工业大学 | A kind of light stabilizer and preparation method thereof containing double hindered piperidine bases |
| CN110938233A (en) * | 2019-11-07 | 2020-03-31 | 宿迁联盛科技股份有限公司 | Hindered amine light stabilizer for nylon and preparation method thereof |
| CN110938233B (en) * | 2019-11-07 | 2021-07-27 | 宿迁联盛科技股份有限公司 | Hindered amine light stabilizer for nylon and preparation method thereof |
| CN114230511A (en) * | 2021-12-31 | 2022-03-25 | 利安隆凯亚(河北)新材料有限公司 | Preparation method of bis (2,2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN114230511B (en) * | 2021-12-31 | 2024-01-26 | 利安隆凯亚(河北)新材料有限公司 | Preparation method of bis (2, 6-tetramethyl-4-piperidinyl) sebacate |
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Application publication date: 20100310 |