CN107903207A - It is double（2,2,6,6 tetramethyl-piperidyl of n-octyloxy）The post treatment method of sebacate - Google Patents
It is double（2,2,6,6 tetramethyl-piperidyl of n-octyloxy）The post treatment method of sebacate Download PDFInfo
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- CN107903207A CN107903207A CN201711376727.XA CN201711376727A CN107903207A CN 107903207 A CN107903207 A CN 107903207A CN 201711376727 A CN201711376727 A CN 201711376727A CN 107903207 A CN107903207 A CN 107903207A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
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Abstract
The invention discloses a kind of double (n-octyloxies 2,2,6,6 tetramethyl-piperidyls) sebacate prepare post treatment method, with decanedioic acid double (2,2,6,6 tetramethyl piperidines) ester and octane be raw material, the back flow reaction under the action of catalyst and tert-butyl hydroperoxide, reaction solution is obtained, the reaction solution of gained is post-processed, the post processing is：Inorganic agent is added in reaction solution so as to remove the decanedioic acid in reaction solution double (2,2,6,6 tetramethyl piperidines) ester NO free radical, precipitation is depressurized so as to remove octane after taking oil phase/filtrate washing, obtains double (n-octyloxies 2,2,6,6 tetramethyl-piperidyls) sebacate.Technique using the present invention can solve double (n-octyloxies 2,2,6,6 tetramethyl-piperidyls) sebacate precipitation when the problem of easily blacking, stablize the colory double (n-octyloxies 2,2 of output, 6,6 tetramethyl-piperidyls) sebacate.
Description
Technical field
The present invention relates to a kind of technique of hindered amine as light stabilizer, is specifically double (n-octyloxy -2,2,6,6- tetramethyl piperazines
Piperidinyl) sebacate prepare aftertreatment technology.
Background technology
Double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates, molecular formula C44H84N2O6, structural formula is as follows：
Double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates are weakly alkaline hindered amine light stabilizers,
Can mutually it be mixed with acid medium, application range is more wide.Double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate quilts
Be widely used in polyethylene, polypropylene, polyvinyl chloride, ABS resin and various fibre resins, and the presence of octyloxy make it is double
(n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate is dissolved in more than 50% organic solvent.It has been reported that preparation
The method of double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates has two kinds：
Method one：With 2,2,6,6- tetramethylpiperidinols for starting material, double (just pungent oxygen are prepared by three-step reaction
Base -2,2,6,6- tetramethyl-piperidyls) sebacate (design, synthesis and the characterization of Deng Yi hindered amine light stabilizers).First
By hydrogen peroxide as oxidant, and 2, it is free that 2,2,6,6- tetramethylpiperidinol nitrogen oxygen are made in the reaction of 2,6,6- tetramethylpiperidinols
Base；Again using molybdenum trioxide as catalyst, by 2,2,6,6- tetramethylpiperidinol NO free radicals and normal octane in tert-butyl group mistake
Radical reaction occurs in the presence of hydrogen oxide and is made 1- octyloxies -2,2,6,6- tetramethylpiperidinols, last 1- octyloxy -2,
2,6,6- tetramethylpiperidinols occur ester exchange reaction with dimethyl sebacate and double (n-octyloxy -2,2,6,6- tetramethyls are made
Piperidyl) sebacate.The method raw material is simple, and reactions steps are more, and each step product all passes through separating-purifying, therefore finally
The high color and luster high-quality stable of product purity.
Method two：With double (2,2,6, the 6- tetramethyl piperidine) esters of decanedioic acid for raw material, in catalyst and tert-butyl hydroperoxide
Most of normal octane is distilled off and obtains product with the abundant back flow reaction of normal octane, reaction solution under the action of hydrogen
(CN200810025327, US4921962).Double (2,2,6,6- tetramethyl piperidines) esters of raw material decanedioic acid of the method are common
Light stabilizer, yield is larger, is readily available；When removing solvent normal octane, as temperature rise and system viscosity become larger, product
The rapid blackening of color and luster, it is difficult to stablize good double (n-octyloxy -2,2,6, the 6- tetramethyl-piperidyls) sebacates of output.
At present, the reason for product blacks is not informed in existing document, product component is not accounted for yet and product is sent out
Black issuable influence.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) last of the ten Heavenly stems two
Post treatment method prepared by acid esters.The present invention is a kind of double as raw material preparation using double (2,2,6,6- tetramethyl piperidines) esters of decanedioic acid
The aftertreatment technology of (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate, technique using the present invention can solve
The problem of easily blacking during double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate precipitations, it is excellent to stablize output color and luster
Double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates of good (Gardner Color is less than 6).
In order to solve the above technical problem, the present invention provides a kind of double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls)
Post treatment method prepared by sebacate, with double (2,2,6, the 6- tetramethyl piperidine) esters of decanedioic acid and octane for raw material, in catalyst
With back flow reaction under the action of tert-butyl hydroperoxide, reaction solution is obtained, the reaction solution of gained is post-processed, is located after described
Manage and be：Inorganic agent is added in reaction solution so as to remove double (2,2,6,6- tetramethyl piperidines) the ester nitrogen oxygen of the decanedioic acid in reaction solution
Free radical, takes oil phase to depressurize precipitation after washing and removes octane, obtain double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) last of the ten Heavenly stems two
Acid esters.
Post treatment method prepared by double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates as the present invention
Improve：
Inorganic agent is liquid inorganic agent or solid processing agent；
When inorganic agent is liquid inorganic agent, inorganic agent is added in reaction solution, liquid separation obtains upper oil phase, by oil phase into
The follow-up washing of row；
When inorganic agent is solid processing agent, inorganic agent is added in reaction solution, filtrate is obtained by filtration, after filtrate is carried out
Continuous washing；
The upper oil phase that liquid separation obtains after washing carries out precipitation again.
Post treatment method prepared by double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates as the present invention
Further improve：Liquid inorganic agent is aqueous solution, 1~30% (quality %) aqueous hydrochloric acid solution of reducing substances；The processing
The volume ratio of agent and reaction solution is 0.9~1.1:1.The aqueous solution of the reducing substances for saturated aqueous sodium thiosulfate,
Saturated sodium sulfite aqueous solution.
Post treatment method prepared by double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates as the present invention
Further improve：The solid processing agent is activated carbon, and the solid processing agent is 4~6g/ with the solid-liquid ratio of reaction solution
100ml。
Post treatment method prepared by double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates as the present invention
Further improve：Washing times are 2~3 times.
The present invention routinely technique with double (2,2,6, the 6- tetramethyl piperidine) esters of decanedioic acid for raw material, in catalyst and tertiary fourth
With the abundant back flow reaction of normal octane under the action of base hydrogen peroxide, after reaction, first the reaction solution of gained is post-processed,
Precipitation is depressurized again and removes octane, obtains double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates.
Using double (2,2,6,6- tetramethyl piperidines) esters of decanedioic acid as the double (n-octyloxy -2,2,6,6- tetramethyls of Material synthesis
Piperidyl) sebacate reactional equation it is as follows.
Inventor is that have studied the reason for product blacks first during invention：The present invention compared for different colourity productions
The liquid chromatography mass spectrometric of product finds that double (2,2,6,6- tetramethyl piperidine) the ester NO free radicals of the decanedioic acid contained in product are to product
Colourity has a great influence, and its content is higher, and product colourity is bigger, and quality is poorer.Therefore it is presently believed that intermediate product decanedioic acid
Double (2,2,6,6- tetramethyl piperidine) ester NO free radicals are the key factors for influencing product colourity, and temperature is 110 DEG C during precipitation,
Pressure is 0.02bar, and double (2,2,6,6- tetramethyl piperidine) the ester NO free radicals of decanedioic acid easily black on this condition, precipitation
Before reaction solution must be handled, to remove double (2,2,6,6- tetramethyl piperidine) the ester NO free radicals of decanedioic acid.
In the present invention, the technique for handling reaction solution is：Inorganic agent is added in reaction solution so as to remove the last of the ten Heavenly stems in reaction solution
Double (2,2,6,6- tetramethyl piperidine) the ester NO free radicals of diacid, liquid separation obtain upper oil phase or filtrate are obtained by filtration, that is, handle
Liquid；Treatment fluid, which is washed with water, to be washed 2~3 times, and the upper oil phase that liquid separation obtains carries out precipitation again.
Beneficial effects of the present invention are shown：It is double (2,2,6,6- tetramethyl piperidines) that reaction solution removes intermediate product decanedioic acid
Ester NO free radical, product is not easy to black during precipitation, and colourity reduces；Water washing liquid can take the accessory substance tert-butyl alcohol out of, carry
The octane purity of high precipitation recycling.Method using the present invention can make the Gardner Color of products therefrom be less than 6.
Embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This.
Embodiment 1, a kind of double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate preparation methods, with the last of the ten Heavenly stems two
Sour double (2,2,6,6- tetramethyl piperidine) esters and octane are raw material, are followed the steps below successively：
(1) double (2,2,6,6- tetramethyl piperidine) the ester 100g (0.21mol) of decanedioic acid are added into 500ml four-hole bottles,
MoO34g, normal octane 250g (3.08mol), open heating stirring, are warming up to 110 DEG C；
(2) 70wt% (quality %) tert-butyl hydroperoxide aqueous solution 130g (tert-butyl hydroperoxides containing 1.01mol are added dropwise
Hydrogen), react and maintain the reflux for during dropwise addition, maintain temperature at 105~110 DEG C；
(3) after being added dropwise, 1g catalyst (molybdenum trioxide MoO is added every 5h3), 15g 70wt% tert-butyl hydroperoxides
Aqueous solution of hydrogen；When reactant is changed into faint yellow from red, stop reaction (that is, the sustained response time about 15h after being added dropwise).
(4) isometric saturated aqueous sodium thiosulfate (35wt%) is added in the reaction solution obtained by step (3) to wash
Double (2,2,6,6- tetramethyl piperidine) ester NO free radicals of decanedioic acid in dereaction liquid are washed away, liquid separation is stood after stirring 10min,
Oil phase (being located at upper strata) is taken to wash 2~3 times (dosage of each water is isometric with oil phase)；
(5) octane is evaporated off in 10mmHg backspins in the oil phase after washing, and temperature is 110 DEG C, obtains double (the just pungent oxygen of product
Base -2,2,6,6- tetramethyl-piperidyls) sebacate 126g, yield 86%；Purity is 94%；Color and luster is faint yellow, Gardner
Colourity is 4.5.
Embodiment 2, a kind of double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate preparation methods, with the last of the ten Heavenly stems two
Sour double (2,2,6,6- tetramethyl piperidines) esters and octane are raw material；
Make " saturated aqueous sodium thiosulfate (35wt%) " in 1 step of embodiment (4) into " saturated sodium sulfite water
Solution (25wt%) "；Volumetric usage is constant；Remaining is equal to embodiment 1.
Obtain double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) the sebacate 12g of product, yield 85%；Purity is
93%；Color and luster is faint yellow.Gardner Color is 4.6.
Embodiment 3, a kind of double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate preparation methods, with the last of the ten Heavenly stems two
Sour double (2,2,6,6- tetramethyl piperidines) esters and octane are raw material；
" saturated aqueous sodium thiosulfate (25wt%) " of 1 step of embodiment (4) is made into " 30wt% (quality %) salt
Aqueous acid "；Volumetric usage is constant；Remaining is equal to embodiment 1.
Obtain double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) the sebacate 119g of product, yield 81%；Purity is
94%；Color and luster is faint yellow.Gardner Color is 5.7.
Embodiment 4, a kind of double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate preparation methods, with the last of the ten Heavenly stems two
Sour double (2,2,6,6- tetramethyl piperidines) esters and octane are raw material；
" saturated aqueous sodium thiosulfate (25wt%) " of 1 step of embodiment (4) is made into " 1wt% (quality %) salt
Aqueous acid "；Volumetric usage is constant；Remaining is equal to embodiment 1.
Obtain double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) the sebacate 120g of product, yield 82%；Purity is
94%；Color and luster is faint yellow.Gardner Color is 4.7.
Embodiment 5, a kind of double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate preparation methods, with the last of the ten Heavenly stems two
Sour double (2,2,6,6- tetramethyl piperidines) esters and octane are raw material；
Step (4) is changed to：
According to the solid-liquid ratio of 5g/100ml, activated carbon adsorption is added in the reaction solution obtained by step (3) with except dereaction
Double (2,2,6,6- tetramethyl piperidine) ester NO free radicals of decanedioic acid in liquid, filter, filtrate washing 2~3 after stirring 10min
Secondary, each water consumption is isometric with filtrate.
Remaining is equal to embodiment 1.
Obtain double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) the sebacate 123g of product, yield 84%；Purity is
93%；Color and luster is faint yellow.Gardner Color is 4.8.
Water-washing step in comparative example 1, cancellation 1 step of embodiment (4), i.e., directly carry out the oil phase obtained by liquid separation follow-up
The step of (5)；Remaining is equal to embodiment 1.
Product yield 68%；Purity is 88%；Color and luster is faint yellow.Gardner Color is 6.8.
" saturated aqueous sodium thiosulfate (35wt%) " in 1 step of embodiment (4), is made into " even two by comparative example 2-1
Sodium sulfite aqueous solution (35wt%) ", volumetric usage is constant；Remaining is equal to embodiment 1.
Product yield 60%；Purity is 86%；Color and luster is faint yellow.Gardner Color 7.8.And the case is also in the presence of even two
The defects of sodium sulfite aqueous solution is extremely unstable.
Comparative example 2-2, make " saturated aqueous sodium thiosulfate (35wt%) " in 1 step of embodiment (4) into " saturations
Sodium nitrite in aqueous solution (46wt%) ", volumetric usage is constant；Remaining is equal to embodiment 1.
Product yield 60%；Purity is 85%；Color and luster is faint yellow.Gardner Color 7.9.
Comparative example 3-1, by " with reaction solution isometric saturated aqueous sodium thiosulfate in 1 step of embodiment (4)
(35wt%) " makes into " the 17.5wt% sodium thiosulfate solutions of 2 times of volumes of reaction solution "；Remaining is equal to embodiment 1.
Product yield 67%；Purity is 83%；Color and luster is faint yellow.Gardner Color 6.8.
Comparative example 3-2, by " with reaction solution isometric saturated aqueous sodium thiosulfate in 1 step of embodiment (4)
(35wt%) " makes into " the 12.5wt% sodium sulfite aqueous solutions of 2 times of volumes of reaction solution "；Remaining is equal to embodiment 1.
Product yield 66%；Purity is 84%；Color and luster is faint yellow.Gardner Color 6.9.
Comparative example 4, make " 30% (quality %) aqueous hydrochloric acid solution " in 3 step of embodiment (4) into " 35% (quality %)
Aqueous sulfuric acid "；Remaining is equal to embodiment 1.
Product yield 70%；Purity is 80%；Color and luster is faint yellow.Gardner Color 7.8.
Comparative example 5-1, make the activated carbon in embodiment 5 into diatomite；Weight is constant；Remaining is equal to embodiment 1.
Product yield 71%；Purity is 81%；Color and luster is faint yellow.Gardner Color 6.9.And the case also there are
Machine is mutually difficult to filter totally, a small amount of diatomite is dissolved in organic phase moderate defect.
Comparative example 5-2, make the activated carbon in embodiment 5 into sodium dithionite；Weight is constant；Remaining is equal to implementation
Example 1.
Product yield 70%；Purity is 76%；Color and luster is faint yellow.Gardner Color 7.7.And also there is production in the case
The defects of thing easily emulsifies and is difficult to layering.
Finally, it should also be noted that it is listed above be only the present invention several specific embodiments.Obviously, this hair
It is bright to be not limited to above example, there can also be many deformations.Those of ordinary skill in the art can be from present disclosure
All deformations for directly exporting or associating, are considered as protection scope of the present invention.
Claims (6)
1. post treatment method prepared by pair (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacate, with decanedioic acid it is double (2,2,
6,6- tetramethyl piperidines) ester and octane be raw material, the back flow reaction under the action of catalyst and tert-butyl hydroperoxide, obtains anti-
Answer liquid, it is characterised in that：The reaction solution of gained is post-processed, the post processing is：In reaction solution add inorganic agent from
And double (2,2,6,6- tetramethyl piperidine) the ester NO free radicals of the decanedioic acid in reaction solution are removed, subtract after taking oil phase/filtrate washing
Pressure-off is molten so as to remove octane, obtains double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates.
2. rear place prepared by double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates according to claim 1
Logos, it is characterised in that：Inorganic agent is liquid inorganic agent or solid processing agent；
When inorganic agent is liquid inorganic agent, inorganic agent is added in reaction solution, liquid separation obtains upper oil phase, after oil phase is carried out
Continuous washing；
When inorganic agent is solid processing agent, inorganic agent is added in reaction solution, filtrate is obtained by filtration, filtrate is carried out follow-up
Washing；
The upper oil phase that liquid separation obtains after washing carries out precipitation again.
3. rear place prepared by double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates according to claim 2
Logos, it is characterised in that：
Liquid inorganic agent is aqueous solution, 1~30% aqueous hydrochloric acid solution of reducing substances；The volume of the inorganic agent and reaction solution
Than for 0.9~1.1:1.
4. rear place prepared by double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates according to claim 3
Logos, it is characterised in that：
The aqueous solution of the reducing substances is saturated aqueous sodium thiosulfate, saturated sodium sulfite aqueous solution.
5. rear place prepared by double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates according to claim 2
Logos, it is characterised in that：
The solid processing agent is activated carbon, and the solid processing agent is 4~6g/100ml with the solid-liquid ratio of reaction solution.
6. prepared according to any described double (n-octyloxy -2,2,6,6- tetramethyl-piperidyls) sebacates of Claims 1 to 5
Post treatment method, it is characterised in that：Washing times are 2~3 times.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862342A (en) * | 2019-11-13 | 2020-03-06 | 天津利安隆新材料股份有限公司 | Preparation method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN110903237A (en) * | 2019-12-16 | 2020-03-24 | 兰州精细化工有限责任公司 | Preparation method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN111056991A (en) * | 2019-12-16 | 2020-04-24 | 兰州精细化工有限责任公司 | Refining and purifying method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN112645867A (en) * | 2020-12-25 | 2021-04-13 | 利安隆凯亚(河北)新材料有限公司 | Synthesis method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4921962A (en) * | 1988-10-19 | 1990-05-01 | Ciba-Geigy Corporation | Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines |
| CN101570507A (en) * | 2008-04-28 | 2009-11-04 | 大丰市天生化学工业有限公司 | Process for preparing bi-(n-octyloxy-2,2,6,6-tetramethyl-piperidyl) diester sebacate |
| CN106699639A (en) * | 2016-12-22 | 2017-05-24 | 甘肃省化工研究院 | Synthesis method of light stabilizer HS-112 |
-
2017
- 2017-12-19 CN CN201711376727.XA patent/CN107903207A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4921962A (en) * | 1988-10-19 | 1990-05-01 | Ciba-Geigy Corporation | Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines |
| CN101570507A (en) * | 2008-04-28 | 2009-11-04 | 大丰市天生化学工业有限公司 | Process for preparing bi-(n-octyloxy-2,2,6,6-tetramethyl-piperidyl) diester sebacate |
| CN106699639A (en) * | 2016-12-22 | 2017-05-24 | 甘肃省化工研究院 | Synthesis method of light stabilizer HS-112 |
Non-Patent Citations (1)
| Title |
|---|
| 张平安: "受阻胺类光稳定剂的合成及工业化生产", 《中国优秀硕士学位论文全文数据库，工程科技I辑》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862342A (en) * | 2019-11-13 | 2020-03-06 | 天津利安隆新材料股份有限公司 | Preparation method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN110862342B (en) * | 2019-11-13 | 2021-10-29 | 天津利安隆新材料股份有限公司 | Preparation method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN110903237A (en) * | 2019-12-16 | 2020-03-24 | 兰州精细化工有限责任公司 | Preparation method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN111056991A (en) * | 2019-12-16 | 2020-04-24 | 兰州精细化工有限责任公司 | Refining and purifying method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN112645867A (en) * | 2020-12-25 | 2021-04-13 | 利安隆凯亚(河北)新材料有限公司 | Synthesis method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN112645867B (en) * | 2020-12-25 | 2022-08-05 | 利安隆凯亚(河北)新材料有限公司 | Synthesis method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
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