CN114507216A - Preparation method of hindered amine light stabilizer 944 - Google Patents
Preparation method of hindered amine light stabilizer 944 Download PDFInfo
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- CN114507216A CN114507216A CN202210218657.XA CN202210218657A CN114507216A CN 114507216 A CN114507216 A CN 114507216A CN 202210218657 A CN202210218657 A CN 202210218657A CN 114507216 A CN114507216 A CN 114507216A
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- 239000004611 light stabiliser Substances 0.000 title claims abstract description 22
- 150000001412 amines Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- UCQQHIZRIQSXEM-UHFFFAOYSA-N hexane-1,6-diamine piperidine Chemical compound N1CCCCC1.NCCCCCCN UCQQHIZRIQSXEM-UHFFFAOYSA-N 0.000 claims abstract description 16
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- 239000000243 solution Substances 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000002390 rotary evaporation Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 4
- 230000002035 prolonged effect Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 2
- HPFWYRKGZUGGPB-UHFFFAOYSA-N 4,6-dichloro-n-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 HPFWYRKGZUGGPB-UHFFFAOYSA-N 0.000 description 1
- 239000012962 antiaging additive Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
A preparation method of a hindered amine light stabilizer 944 relates to the technical field of light stabilizer synthesis, wherein cyanuric chloride partially reacts with water to obtain cyanuric chloride and intermediate 1 coexisting solution, cyanuric chloride and intermediate 1 react with tert-octylamine respectively to obtain intermediate 2 and intermediate 3, intermediate 2 and hexamethylenediamine piperidine undergo polymerization, and intermediate 3 performs end capping on product molecules to obtain the hindered amine light stabilizer 944. The invention has the beneficial effects that: according to the method disclosed by the invention, the purposes of controlling the molecular weight and the molecular band width of the light stabilizer 944 are achieved by adjusting the proportion of the intermediate 2 and the intermediate 3 and three-stage temperature programming, meanwhile, the generation of small molecular products is reduced, the possibility of cyclization of the products is avoided, the post-treatment cost is effectively reduced, and the light transmittance of the products is improved.
Description
Technical Field
The invention relates to the technical field of organic synthesis, and particularly relates to a preparation method of a hindered amine light stabilizer 944.
Background
Hindered amine light stabilizer 944 is a class of anti-aging additives with excellent performance. It has the features of high efficiency, low toxicity, low cost and high compatibility with polymer material, and may be used widely in various kinds of organic polymer material.
The currently common synthesis methods of hindered amine light stabilizer 944 include: two-step method, three-step method and four-step method. Wherein the two-step method is to react cyanuric chloride with tert-octylamine to obtain 2-tert-octylamino-4, 6-dichloro-1, 3, 5-triazine, then carry out high pressure polymerization with hexamethylenediamine piperidine, and carry out temperature programming to obtain the hindered amine light stabilizer 944. The three-step method is that cyanuric chloride and tert-octylamine are firstly used for generating an intermediate, then the intermediate is added to hexamethylene diamine piperidine, and finally the intermediate is polymerized with a small amount of hexamethylene diamine piperidine to obtain the hindered amine light stabilizer 944. In both methods, excessive hexamethylenediamine piperidine is required to be added to terminate polymerization in polymerization reaction, so a large amount of cyclic insoluble substances and micromolecular products are generated, the difficulty of post-treatment is increased, the product quality is reduced, and the cost is increased. Patent CN 108623566 was synthesized 944 using a four-step process that first reacted cyanuric chloride with tert-octylamine and further co-heated with water to prepare a second chlorine hydrolysate for end-capping in a subsequent polymerization step. Compared with the traditional two-step and three-step synthesis routes, the route reduces the generation of small molecular products, reduces the post-treatment difficulty, but has complicated reaction process and uncontrollable molecular weight.
Disclosure of Invention
In view of the above problems in the prior art, the present invention aims to provide a method for preparing a light stabilizer 944, which can effectively control the molecular weight of the product and has the advantage of narrow molecular weight range.
The invention provides a preparation method of a hindered amine light stabilizer 944, which comprises the following steps:
step 1, adding cyanuric chloride into acetone, stirring and dissolving, then, dropwise adding water and stirring, and reacting part of cyanuric chloride to produce an intermediate 1 to obtain a solution in which cyanuric chloride and the intermediate 1 coexist; the first chlorine of the cyanuric chloride is very easy to hydrolyze, and the cyanuric chloride is excessive, so that water is reacted completely, other byproducts are not generated basically, no post-treatment is needed, and the next reaction can be carried out directly.
Step 2, dropwise adding a tert-octylamine solution into the solution, stirring, preserving heat after dropwise adding, dropwise adding a sodium hydroxide solution with the mass fraction of 15-30%, preserving heat after dropwise adding, washing with water, filtering, and performing rotary evaporation to obtain a mixed solution of an intermediate 2 and an intermediate 3, reacting cyanuric chloride with tert-octylamine to obtain an intermediate 2, and reacting an intermediate 1 with tert-octylamine to obtain an intermediate 3;
step 3, sequentially adding a solvent, a sodium hydroxide solution with the mass fraction of 5-40% and hexamethylenediamine piperidine into the mixed solution obtained in the step 2, pressurizing to 0.2-0.5MPa, carrying out first-stage temperature programming, raising the temperature to 50-70 ℃, and preserving the temperature for 0.5-2 h; then, carrying out two-stage temperature programming, raising the temperature to 100-120 ℃, and then preserving the heat for 4-6 h; then three-stage programmed heating is carried out, the temperature is raised to 150 ℃ and 220 ℃, and then the temperature is kept for 5-10 h; and washing, filtering and desolventizing the reaction solution to obtain the hindered amine light stabilizer 944.
The molar ratio of the cyanuric chloride to the water in the step 1 is ((n + 1): 0- (n + 1): 1; the molar ratio of cyanuric chloride to the intermediate 1 in the solution obtained in the step 1 is (n.0-n.2) to 1, and the value of n is 1,2,3,4 and 5.
The molar ratio of the tert-octylamine to the cyanuric chloride in the step 2 is (1.0-1.2) to 1; the molar ratio of the sodium hydroxide to the cyanuric chloride in the step 2 is (1-3) to 1; the molar ratio of the intermediate 2 to the intermediate 3 in the solution obtained in the step 2 is ((n-1), 8-n.3): 1, and the value of n is 1,2,3,4, 5.
The molar ratio of the sodium hydroxide solution to the sum of the intermediate 2 and the intermediate 3 in the step 3 is 1-4: 1; the molar ratio of the hexamethylenediamine piperidine to the intermediate 2 in the step 3 is 1: 1-2.
In the step 3, the temperature is programmed in the first section, and the first chlorine on the intermediate 2 reacts with hexamethylenediamine piperidine; the second-stage temperature programming is carried out, the second chlorine on the intermediate 2 reacts with the hexamethylenediamine piperidine to carry out polymerization, and a molecular chain is prolonged; and (3) carrying out three-stage temperature programming, taking the intermediate 3 as a sealing end body, and carrying out single-side sealing on the product.
The reaction route involved in preparing hindered amine light stabilizer 944 in the present invention is as follows:
the reaction in step 1:
the reaction in step 2 is as follows:
the reaction in step 3 is as follows:
the invention has the beneficial effects that:
(1) the reaction sequence of the intermediates 2 and 3 is adjusted by three-stage temperature programming by utilizing the difference of three chlorine reaction conditions on cyanuric chloride molecules and the difference of the influence of different groups on chlorine, the intermediate 3 is used as a single-side end-sealing body and is used as an end-sealing group to finish the elimination of the last chlorine atom in the third-stage temperature programming, and the aim of reducing the width of the molecular band is fulfilled. Plays a role in controlling the polymerization degree of the product and finally reduces the molecular weight width of the hindered amine light stabilizer 944.
(2) The molar ratio of the intermediates 2 and 3 is accurately controlled by adjusting the proportion of water participating in the reaction, so that the polymerization degree is controlled, the molecular weight of the light stabilizer 944 is enabled to be around 258.75+598.96n, and the aim of controlling the molecular weight is fulfilled.
(3) The intermediate 3 is used for end capping instead of adding excessive hexamethylenediamine piperidine, so that the generation of small molecular products and the possibility of cyclization of the intermediate 2 and the hexamethylenediamine piperidine are reduced, and the quality of products is improved.
Detailed Description
Example 1, 93.0g of cyanuric chloride was poured into a flask, acetone was added, 2.2g of water was added dropwise at normal temperature, and after completion of the reaction, solution 1 (containing 20g of intermediate 1 and 69.6g of cyanuric chloride) was obtained.
And (2) dropwise adding 65.1g of tert-octylamine solution into the solution 1 at 50 ℃ for 6h, keeping the temperature for 5h, slowly dropwise adding 150g of 20% sodium hydroxide solution, controlling the temperature to be about 10 ℃, finishing dropwise adding after 2h, and keeping the temperature for 6 h. After the reaction, 135g of liquid 2 (containing 101g of intermediate 2 and 32g of intermediate 3) was obtained by rotary evaporation and washing with water.
Pouring the solution 2 into a high-pressure reaction kettle, and sequentially adding 500g of toluene, 90g of 40% sodium hydroxide solution, 150.0g of hexamethylenediamine piperidine and N2And after replacement, pressurizing to 0.4MPa, heating to 60 ℃, preserving heat for 1h, heating to 100 ℃, preserving heat for 4h, finally heating to 200 ℃, preserving heat for 8h, washing with water, filtering and distilling to obtain the hindered amine light stabilizer 944. The molecular weight interval is 2000-2200, the light transmittance is 98.5 percent, and the average yield of repeated tests is more than 95.6 percent.
Example 2, 93.0g of cyanuric chloride was poured into a flask, acetone was added, and 1.8g of water was added dropwise at normal temperature to complete the reaction, thereby obtaining solution 1 (containing 16.6g of intermediate 1 and 73.7g of cyanuric chloride).
And (2) dropwise adding 65.1g of tert-octylamine solution into the solution 1 at 50 ℃ for 6h, keeping the temperature for 5h, slowly dropwise adding 150g of 20% sodium hydroxide solution, controlling the temperature to be about 10 ℃, finishing dropwise adding after 2h, and keeping the temperature for 6 h. After the reaction, 134g of liquid 2 (containing 103g of intermediate 2 and 31g of intermediate 3) was obtained by rotary evaporation and washing with water.
Pouring the solution 2 into a high-pressure reaction kettle, and sequentially adding 500g of toluene, 100g of 40% sodium hydroxide solution, 158g of hexamethylenediamine piperidine and N2And after replacement, pressurizing to 0.4MPa, heating to 60 ℃, preserving heat for 1h, heating to 100 ℃, preserving heat for 4h, finally heating to 220 ℃, preserving heat for 8h, washing with water, filtering and distilling to obtain the hindered amine light stabilizer 944. The molecular weight range is 2600-2750, the light transmittance is 98.9 percent, and the average yield of repeated tests is more than 95.2 percent.
Example 3, 93.0g of cyanuric chloride was poured into a flask, acetone was added, and 2.9g of water was added dropwise at normal temperature to complete the reaction, thereby obtaining solution 1 (containing intermediate 1 in an amount of 26.7g and cyanuric chloride in an amount of 63.3 g).
And (2) dropwise adding 65.1g of tert-octylamine solution into the solution 1 at 50 ℃ for 6h, keeping the temperature for 5h, slowly dropwise adding 150g of 20% sodium hydroxide solution, controlling the temperature to be about 10 ℃, finishing dropwise adding after 2h, and keeping the temperature for 6 h. After the reaction, 132g of liquid 2 (containing 98g of intermediate 2 and 34g of intermediate 3) was obtained by rotary evaporation and washing with water.
Pouring the solution 2 into a high-pressure reaction kettle, and sequentially adding 500g of toluene, 85g of 40% sodium hydroxide solution, 133g of hexamethylenediamine piperidine and N2And after replacement, pressurizing to 0.4MPa, heating to 60 ℃, preserving heat for 1h, heating to 100 ℃, preserving heat for 4h, finally heating to 180 ℃, preserving heat for 8h, washing with water, filtering and distilling to obtain the hindered amine light stabilizer 944. The molecular weight range is 1400-1600 percent, the light transmittance is 98.9 percent, and the average yield of repeated experiments is more than 96.5 percent.
Claims (5)
1. A method for producing a hindered amine light stabilizer 944, comprising the steps of:
step 1, adding cyanuric chloride into acetone, stirring and dissolving, then, dropwise adding water and stirring, and reacting part of cyanuric chloride to produce an intermediate 1 to obtain a solution in which cyanuric chloride and the intermediate 1 coexist;
step 2, dropwise adding a tert-octylamine solution into the solution, stirring, preserving heat after dropwise adding, dropwise adding a sodium hydroxide solution with the mass fraction of 15-30%, preserving heat after dropwise adding, washing with water, filtering, and performing rotary evaporation to obtain a mixed solution of an intermediate 2 and an intermediate 3, reacting cyanuric chloride with tert-octylamine to obtain an intermediate 2, and reacting an intermediate 1 with tert-octylamine to obtain an intermediate 3;
step 3, sequentially adding a solvent, a sodium hydroxide solution with the mass fraction of 5-40% and hexamethylenediamine piperidine into the mixed solution obtained in the step 2, pressurizing to 0.2-0.5MPa, carrying out first-stage temperature programming, raising the temperature to 50-70 ℃, and preserving the temperature for 0.5-2 h; then, carrying out two-stage temperature programming, raising the temperature to 100-120 ℃, and then preserving the heat for 4-6 h; then three-stage programmed heating is carried out, the temperature is raised to 150 ℃ and 220 ℃, and then the temperature is kept for 5-10 h; and washing, filtering and desolventizing the reaction solution to obtain the hindered amine light stabilizer 944.
2. The method of claim 1, wherein the molar ratio of cyanuric chloride to water in step 1 is ((n +1).0- (n +1). 1: 1; the molar ratio of cyanuric chloride to the intermediate 1 in the solution obtained in the step 1 is (n.0-n.2) to 1, and the value of n is 1,2,3,4 and 5.
3. The method of claim 1, wherein the molar ratio of tert-octylamine to cyanuric chloride in step 2 is (1.0-1.2): 1; the molar ratio of the sodium hydroxide to the cyanuric chloride in the step 2 is (1-3) to 1; the molar ratio of the intermediate 2 to the intermediate 3 in the solution obtained in the step 2 is ((n-1), 8-n.3): 1, and the value of n is 1,2,3,4, 5.
4. The method of claim 1, wherein the molar ratio of the sodium hydroxide solution in step 3 to the sum of intermediate 2 and intermediate 3 is 1-4: 1; the molar ratio of the hexamethylenediamine piperidine to the intermediate 2 in the step 3 is 1: 1-2.
5. The method of claim 1, wherein in step 3, the first chlorine of intermediate 2 is reacted with hexamethylenediamine piperidine at the programmed temperature; the second-stage temperature programming is carried out, the second chlorine on the intermediate 2 reacts with the hexamethylenediamine piperidine to carry out polymerization, and a molecular chain is prolonged; and (3) carrying out three-stage temperature programming, taking the intermediate 3 as a sealing end body, and carrying out single-side sealing on the product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115975189A (en) * | 2022-12-26 | 2023-04-18 | 江苏富比亚化学品有限公司 | Synthesis method of hindered amine light stabilizer 944 |
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| US4504610A (en) * | 1983-02-07 | 1985-03-12 | Montedison S.P.A. | Self-extinguishing polymeric compositions |
| CN1108251A (en) * | 1993-12-24 | 1995-09-13 | 住友化学工业株式会社 | A process for the preparation of polyaminotriazines |
| CN101591331A (en) * | 2009-06-25 | 2009-12-02 | 中国乐凯胶片集团公司 | A kind of preparation method of hindered amine as light stabilizer |
| CN108623566A (en) * | 2018-04-28 | 2018-10-09 | 宿迁联盛科技有限公司 | A kind of synthesis technology of hindered amine light stabilizer 944 |
| CN109678842A (en) * | 2019-01-31 | 2019-04-26 | 宿迁联盛科技股份有限公司 | A kind of production technology of 944 intermediate of continuous production light stabilizer |
-
2022
- 2022-03-08 CN CN202210218657.XA patent/CN114507216A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504610A (en) * | 1983-02-07 | 1985-03-12 | Montedison S.P.A. | Self-extinguishing polymeric compositions |
| CN1108251A (en) * | 1993-12-24 | 1995-09-13 | 住友化学工业株式会社 | A process for the preparation of polyaminotriazines |
| CN101591331A (en) * | 2009-06-25 | 2009-12-02 | 中国乐凯胶片集团公司 | A kind of preparation method of hindered amine as light stabilizer |
| CN108623566A (en) * | 2018-04-28 | 2018-10-09 | 宿迁联盛科技有限公司 | A kind of synthesis technology of hindered amine light stabilizer 944 |
| CN109678842A (en) * | 2019-01-31 | 2019-04-26 | 宿迁联盛科技股份有限公司 | A kind of production technology of 944 intermediate of continuous production light stabilizer |
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| Title |
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| 孟祎等: ""受阻胺类光稳定剂GW－944的合成"", 《精细化工》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115975189A (en) * | 2022-12-26 | 2023-04-18 | 江苏富比亚化学品有限公司 | Synthesis method of hindered amine light stabilizer 944 |
| CN115975189B (en) * | 2022-12-26 | 2024-06-11 | 江苏富比亚化学品有限公司 | Synthesis method of hindered amine light stabilizer 944 |
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