CN110396060A - A kind of light stabilizer and preparation method thereof containing double hindered piperidine bases - Google Patents
A kind of light stabilizer and preparation method thereof containing double hindered piperidine bases Download PDFInfo
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- CN110396060A CN110396060A CN201910628639.7A CN201910628639A CN110396060A CN 110396060 A CN110396060 A CN 110396060A CN 201910628639 A CN201910628639 A CN 201910628639A CN 110396060 A CN110396060 A CN 110396060A
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- Prior art keywords
- light stabilizer
- containing double
- hindered piperidine
- preparation
- dmt
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000004611 light stabiliser Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 238000005406 washing Methods 0.000 claims abstract description 13
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 238000001953 recrystallisation Methods 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- -1 diphenyl stannous chloride Chemical compound 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000005119 centrifugation Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 239000012188 paraffin wax Substances 0.000 claims description 4
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000001119 stannous chloride Substances 0.000 claims description 3
- 235000011150 stannous chloride Nutrition 0.000 claims description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 229920000728 polyester Polymers 0.000 abstract description 3
- 150000008442 polyphenolic compounds Polymers 0.000 abstract description 3
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004402 polyphenol group Polymers 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- QUVMSYUGOKEMPX-UHFFFAOYSA-N 2-methylpropan-1-olate;titanium(4+) Chemical compound [Ti+4].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-] QUVMSYUGOKEMPX-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009498 subcoating Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention discloses a kind of light stabilizers and preparation method thereof containing double hindered piperidine bases.Its structure is shown below, the structure is by introducing dimethyl terephthalate (DMT) as intermediate connection chain, the piperidinamine replaced using alkoxide is as effect base, obtain a kind of light stabilizer containing double hindered piperidine bases, since the light stabilizer structure is similar to target domain polyester, poly- phenol structure, there is extraordinary application prospect in the field.The invention also discloses the preparation methods of the light stabilizer: by 1- alkoxy -2,2,6,6, and-tetramethyl-piperidine alcohols, dimethyl terephthalate (DMT), catalysts and solvents mixing react 5h at 120 DEG C, and solvent is evaporated off in cooling washing, and product can be obtained in recrystallization.Using this technique synthesis light stabilizer have high income, purity is good, color is good, convenient for operation implement, be suitable for industrialized production；
Description
Technical field
The present invention relates to light stabilizer technical field, in particular to a kind of light stabilizer containing double hindered piperidine bases and its
Preparation method.
Background technique
Hindered amine light stabilizer (HALS) becomes light stabilizer in synthetic material auxiliary agent and disappears due to its superior performance
The main product for taking market occupies leading position in world's light stabilizer market comsupton structure.With the basis of light stabilizer
Research deepens continuously with application study, and the application range of HALS constantly expands, and covers agricultural film, engineering plastics, fiber, high score
In the various fields such as sub- coating, artificial carpet and outdoor various plastic products.
Common hindered amine light stabilizer products C himassorb 944 using and process in due to alkalinity compared with
Height need to be added acidic materials, contact with acidic materials to reduce alkalinity, be easy into salt and reduce light stability, thus
Limit the synergistic stability effect of remaining acidic resins, halogen containing flame-retardant and phenolic antioxidant.And 1- alkoxy hindered amine due to
The low alkalinity of molecule, it is possible to prevente effectively from inactivation caused by acidic materials.Common alkoxylation products are to Tinuvin
770 alkoxides for carrying out n-octyl replace, and obtain product Tinuvin 123.But such product is due to the connection in structure
Chain is mainly straight chain, less limited in certain fields (polyester, poly- phenol) application.
Summary of the invention
The present invention will provide a kind of light stabilizer and preparation method thereof containing double hindered piperidine bases, to solve the prior art
Existing hindered amine light stabilizer alkalinity height, the limited defect of suitable application area.
In order to solve the problems existing in the prior art, the technical scheme is that a kind of light containing double hindered piperidine bases is steady
Determine agent, it is characterised in that: the structural formula of the stabilizer are as follows:
R is C in formula1-C18Linear paraffin, C5-C7Cycloalkane.
A kind of light stabilizer preparation method containing double hindered piperidine bases, characterized by the following steps:
Tetramethyl piperidine 01 derivatives, dimethyl terephthalate (DMT), catalysts and solvents are added into four-hole bottle for step 1)
Mixing；
The tetramethyl piperidine 01 derivatives: dimethyl terephthalate (DMT) molar feed ratio be 2:1.05~1.1, two
Person accounts for total amount of feeding 35-50%, and catalyst amount accounts for the 0.5~1.0% of total amount of feeding,
Step 2) is heated to 120-140 DEG C, constantly steams the methanol that reaction generates, reacting after 4-8h terminates；
Step 3) is cooled to room temperature, and adds washing 2-3 times, collects organic phase, evaporating solvent under reduced pressure；
Mixed solvent recrystallization is added in step 4), through filtering, centrifugation, washing operation, obtains white pale pink powder, as
Final product.
Catalyst in the step 1) be methanesulfonic acid, p-methyl benzenesulfonic acid, tin chloride dihydrate, to diphenyl stannous chloride,
Any one in isopropyl titanate, iso-butyl titanate.
Solvent is toluene, any one in dimethylbenzene in the step 1).
Solvent is the mixture of ethyl alcohol and water in the step 4).
Compared with prior art, advantages of the present invention is as follows:
1) present invention replaces the fat diacid dimethyl ester of branch by esterification using dimethyl terephthalate (DMT), obtains
To a kind of light stabilizer containing double hindered piperidine bases, preparation process is simple, easy to operate, and product has the effect for reducing alkalinity
Fruit has extraordinary application prospect in fields such as polyester, poly- phenol.
Specific embodiment
A kind of reaction equation of the light stabilizer containing double hindered piperidine bases are as follows:
R is C in formula1-C18Linear paraffin, C5-C7Cycloalkane.
The step of above-mentioned light stabilizer preparation method are as follows:
Step 1): tetramethyl piperidine 01 derivatives, dimethyl terephthalate (DMT), catalyst and molten are added into four-hole bottle
Agent mixing；
Reactant tetramethyl piperidine 01 derivatives: dimethyl terephthalate (DMT) molar feed ratio be 2:1.05~1.1, two
Person accounts for total amount of feeding 35-50%；
Catalyst be methanesulfonic acid, p-methyl benzenesulfonic acid, tin chloride dihydrate, to diphenyl stannous chloride, isopropyl titanate, titanium
Any one in sour isobutyl ester；Dosage accounts for the 0.5~1.0% of total amount of feeding；
Solvent is toluene, any one in dimethylbenzene；
Step 2): being heated to 120-140 DEG C, constantly steams the methanol that reaction generates, reacting after 4-8h terminates；
Step 3): being cooled to room temperature, and adds washing 2-3 times, collects organic phase, evaporating solvent under reduced pressure；
Step 4): being added mixed solvent (mixed system of ethyl alcohol and water) recrystallization, through filtering, centrifugation, washing operation,
Obtain white pale pink powder, as final product.
In order to make the objectives, technical solutions, and advantages of the present invention clearer, with reference to embodiments, to this hair
It is bright to be further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, not
For limiting the present invention.
Embodiment 1
Into the four-hole bottle for having still head, blender, thermometer, positive propoxy -2 1- of 430.3g (2mol) are added,
2,6,6 ,-tetramethyl-piperidine alcohols, the dimethyl terephthalate (DMT) of 213.4g (1.1mol), 12g p-methyl benzenesulfonic acid and 800g first
Benzene is warming up to 140 DEG C of reaction 6h, during which constantly steams methanol, after completion of the reaction, be down to room temperature, add 200mL water washing twice,
It is dry to collect organic phase, decompression steams solvent, and 400mL ethyl alcohol is added: water=2:1 mixed solution recrystallization is filtered, is centrifuged, is washed
After washing, bis- (1- positive propoxy -2,2,6,6- tetramethyl -4- piperidyls) the terephthalate 498.5g of white solid are obtained, are received
Rate is 88.95%, HPLC detection purity 98.12%.
Embodiment 2
Into the four-hole bottle for having still head, blender, thermometer, the 1- cyclohexyl -2,2 of 506.4g (2mol) is added,
6,6 ,-tetramethyl-piperidine alcohols, the dimethyl terephthalate (DMT) of 213.4g (1.1mol), 13g methanesulfonic acid and 800g dimethylbenzene.It rises
During which temperature constantly steams methanol, after completion of the reaction, is down to room temperature, add 200mL water washing twice, collect to 130 DEG C of reaction 5h
Organic phase is dry, and decompression steams solvent, and 400mL ethyl alcohol: water=2:1 mixed solution recrystallization, filtering, centrifugation, washing is added
Afterwards, bis- (1- cyclohexyl -2,2,6,6- tetramethyl -4- piperidyls) the terephthalate 525.1g of white solid are obtained, yield is
82.05%, HPLC detect purity 98.55%.
Embodiment 3:
Into the four-hole bottle for having still head, blender, thermometer, n-octyl -2,2 of addition 570.6g (2mol), 6,
6 ,-tetramethyl-piperidine alcohols, the dimethyl terephthalate (DMT) of 213.4g (1.1mol), 14g tin chloride dihydrate and 800g dimethylbenzene.
130 DEG C of reaction 7h are warming up to, methanol is during which constantly steamed, after completion of the reaction, is down to room temperature, add 200mL water washing twice, are received
It is dry to collect organic phase, decompression steams solvent, and 400mL ethyl alcohol: water=2:1 mixed solution recrystallization, filtering, centrifugation, washing is added
Afterwards, bis- (1- n-octyl -2,2,6,6- tetramethyl -4- piperidyls) the terephthalate 611.5g of white solid are obtained, yield is
87.28%, HPLC detect purity 98.99%.
The structural formula of light stabilizer containing double hindered piperidine bases made from above-described embodiment are as follows:
R is C in formula1-C18Linear paraffin, C5-C7Cycloalkane.
The foregoing is only a preferred embodiment of the present invention, is not intended to limit the scope of the present invention, this
The protection scope of invention should be with the technical solution of claim record, and technology is special in the technical solution recorded including claim
The equivalents of sign are protection scope, i.e., equivalent replacement within this range is improved, also protection scope of the present invention it
It is interior.
Claims (5)
1. a kind of light stabilizer containing double hindered piperidine bases, it is characterised in that: the structural formula of the stabilizer are as follows:
R is C in formula1-C18Linear paraffin, C5-C7Cycloalkane.
2. a kind of light stabilizer preparation method containing double hindered piperidine bases according to claim 1, it is characterised in that: including
Following steps:
Tetramethyl piperidine 01 derivatives, dimethyl terephthalate (DMT), catalysts and solvents mixing are added into four-hole bottle for step 1)；
The tetramethyl piperidine 01 derivatives: dimethyl terephthalate (DMT) molar feed ratio is 2:1.05~1.1, and the two Zhan is total
Inventory 35-50%, catalyst amount account for the 0.5~1.0% of total amount of feeding,
Step 2) is heated to 120-140 DEG C, constantly steams the methanol that reaction generates, reacting after 4-8h terminates；
Step 3) is cooled to room temperature, and adds washing 2-3 times, collects organic phase, evaporating solvent under reduced pressure；
Mixed solvent recrystallization is added in step 4), through filtering, centrifugation, washing operation, obtains white pale pink powder, as final to produce
Object.
3. a kind of light stabilizer preparation method containing double hindered piperidine bases according to claim 2, it is characterised in that: described
Catalyst in step 1) be methanesulfonic acid, p-methyl benzenesulfonic acid, tin chloride dihydrate, to diphenyl stannous chloride, isopropyl titanate, titanium
Any one in sour isobutyl ester.
4. a kind of light stabilizer preparation method containing double hindered piperidine bases according to claim 3, it is characterised in that: described
Solvent is toluene, any one in dimethylbenzene in step 1).
5. a kind of light stabilizer preparation method containing double hindered piperidine bases according to claim 4, it is characterised in that: described
Solvent is the mixture of ethyl alcohol and water in step 4).
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| CN101768104A (en) * | 2010-01-04 | 2010-07-07 | 南通惠康国际企业有限公司 | Method for producing light stabilizer sebacic acid (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) diester |
| CN102382039A (en) * | 2011-08-08 | 2012-03-21 | 宿迁联盛化学有限公司 | Synthesizing technology of hindered amine light stabilizer Tinuvin-770 |
| CN106957258A (en) * | 2017-02-28 | 2017-07-18 | 江苏兆康新材料有限公司 | The preparation method of the piperidyl stearate of 2,2,6,6 tetramethyl 4 |
| CN107721910A (en) * | 2017-08-28 | 2018-02-23 | 新秀化学（烟台）有限公司 | A kind of production technology of double (piperidyl of 12,2,6,6 tetramethyl of alkoxy 4) alkyl acid esters |
| CN109776398A (en) * | 2019-03-26 | 2019-05-21 | 南通大学 | A kind of preparation method of composite light stabilizer |
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