CN110183364A - A kind of thioether class bis-phenol acrylate multiple-effect antioxidant and preparation method thereof - Google Patents
A kind of thioether class bis-phenol acrylate multiple-effect antioxidant and preparation method thereof Download PDFInfo
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- CN110183364A CN110183364A CN201910569404.5A CN201910569404A CN110183364A CN 110183364 A CN110183364 A CN 110183364A CN 201910569404 A CN201910569404 A CN 201910569404A CN 110183364 A CN110183364 A CN 110183364A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
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- 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
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
The invention discloses a kind of thioether class bis-phenol acrylate multiple-effect antioxidant, have the molecular structure being shown below:Thioether bond in thioether class bis-phenol acrylate multiple-effect antioxygen agent molecule of the present invention both containing be obstructed phenol functional group and auxiliary antioxidant as primary antioxidant, simultaneously also containing the acrylic acid phenolic ester structure with carbon radicals capture function, the antioxidation of three-in-one can be played in processing of high molecular material and use process, high molecular material can preferably be protected, avoid the degradation and aging of product, solve the problems, such as that simple function antioxidant is poor to high molecular material antioxidation effect, and corresponding preparation process reaction temperature is low, low energy consumption, by-product filtering can remove, do not generate waste water, solvent is recyclable, it is environmentally protective.
Description
Technical field
The present invention relates to plastic additive more particularly to a kind of thioether class bis-phenol acrylate multiple-effect antioxidant and its preparation sides
Method.
Background technique
It is a kind of polymer builder that antioxidant is anti-, in the presence of it is only a small amount of in polymeric system, so that it may delay or press down
The progress of polymer oxidation process processed, to prevent the aging of polymer and prolong its service life, be otherwise known as anti-aging agent.Have
The thermal oxidation process of machine compound is a series of free chain reaction, under the action of heat or light, the chemical bond hair of molecule
Raw fracture, generates active free radical, these free radicals can trigger a series of free chain reaction, lead to organic compound
Basic change occurs for the structure and property of object, and the mechanism of action of antioxidant is exactly to eliminate the free radical just generated, prevents chain type
The progress of reaction, to play the role of preventing aging.Common Hinered phenols antioxidant anti-aging mechanism is exactly its functional group
It is combined with free radical, but function is relatively simple, anti-aging effect is general.
Summary of the invention
The present invention provides a kind of thioether class bis-phenol third aiming at the problem that existing Hinered phenols antioxidant anti-aging single effect
Olefin(e) acid ester multiple-effect antioxidant and preparation method thereof.
The technical scheme to solve the above technical problems is that a kind of thioether class bis-phenol acrylate multiple-effect antioxygen
Agent, which is characterized in that it has the molecular structure as shown in formula I:
Wherein, R1Straight chain for C1-C5 or the alkyl with branch, R2Straight chain for C1-C5 or the alkyl with branch.
Specifically, the thioether class bis-phenol acrylate multiple-effect antioxidant has the molecular structure as shown in formula a-e:
The invention further relates to the preparation methods of above-mentioned thioether class bis-phenol acrylate multiple-effect antioxidant, the steps include: sulphur
Ethers bisphenol compound is dissolved in solvent, and catalyst of triethylamine and acrylic acid is added, controlled at 20 DEG C -50 DEG C, stirring
0.5-1.5h is mixed, phosphorus oxychloride is added dropwise into reaction system, control time for adding is 50-90min, is warming up to after being added dropwise to complete
60 DEG C -90 DEG C, lower reaction 1-4h is stirred, reaction solution is filtered, filter cake is eluted with normal heptane, leacheate is evaporated under reduced pressure, it will
Vinasse stirring and crystallizing at 0-5 DEG C, filters again, collect filter cake to get.The key reaction being related to are as follows:
Wherein, the mass ratio of the material of the thioether class bisphenol compound and acrylic acid, phosphorus oxychloride is 1:(1.1-1.4):
(1.1-1.5)；The mass ratio of the material of the thioether class bisphenol compound and the triethylamine is 1:(4-6)；The solvent is first
One of benzene, dimethylbenzene, trimethylbenzene, benzene, normal heptane or n -nonane.
The beneficial effects of the present invention are: both containing conduct in thioether class bis-phenol acrylate multiple-effect antioxygen agent molecule of the present invention
The thioether bond of be obstructed phenol functional group and the auxiliary antioxidant of primary antioxidant, while also containing third with carbon radicals capture function
Olefin(e) acid phenolic ester structure, can play the antioxidation of three-in-one, Ke Yigeng in processing of high molecular material and use process
High molecular material is protected well, avoids the degradation and aging of product, solves simple function antioxidant to high molecular material antioxygen
Change the problem of function and effect difference, and corresponding preparation process reaction temperature is low, low energy consumption, and by-product filtering can remove, no
Waste water is generated, solvent is recyclable, environmentally protective.
Detailed description of the invention
Fig. 1 is the nuclear magnetic resonance map of 1 compound a of embodiment；Fig. 2 is the liquid chromatogram of 1 compound a of embodiment.
Specific embodiment
Below in conjunction with example, present invention is described, and the given examples are served only to explain the present invention, is not intended to limit this
The range of invention.
The synthesis of 1 compound a of embodiment
2,2 '-thiobis (4- methyl-6-tert-butylphenol) 358.5g (1mol) is added in 3L there-necked flask, is added
Normal heptane 1000ml, triethylamine 404g (4mol), acrylic acid 86.5g (1.2mol), stirring are warming up to 60 DEG C, start that trichlorine is added dropwise
Oxygen phosphorus 199g (1.3mol) is dripped 60~80 DEG C of temperature control, time for adding 1h when dropwise addition and is warming up to 85 DEG C of heat preservation 1.5h.Reaction
After, to the slightly cooling suction filtration of reaction solution, filter cake is triethylamine salt, is eluted with normal heptane 500ml, organic phase is merged, and is depressurized
Normal heptane 1200ml is distilled out, remaining residue liquid is stirred into cooling crystallization, crystallization at 0 to 5 DEG C filters, obtains product 338.3g,
Yield 82%.
The synthesis of 2 compound b of embodiment
2,2 '-thiobis (4- ethyl -6- tert-butyl phenol) 386.5g (1mol) is added in 3L there-necked flask, is added
Normal heptane 1100ml, triethylamine 505g (5mol), acrylic acid 93.7g (1.3mol), stirring are warming up to 65 DEG C, start that trichlorine is added dropwise
Oxygen phosphorus 199g (1.3mol) is dripped 65~80 DEG C of temperature control, time for adding 1h when dropwise addition and is warming up to 85 DEG C of heat preservation 1.5h.Reaction
After, to the slightly cooling suction filtration of reaction solution, filter cake is triethylamine salt, is eluted with normal heptane 500ml, organic phase is merged, and is depressurized
Normal heptane 1300ml is distilled out, remaining residue liquid is stirred into cooling crystallization, crystallization at 2 to 5 DEG C obtains product 373g, yield
84.6%.
The synthesis of 3 compound c of case study on implementation
2,2 '-thiobis (4,6- DI-tert-butylphenol compounds) 414.5g (1mol) is added in 3L there-necked flask, first is added
Benzene 1100ml, triethylamine 535g (5.3mol), acrylic acid 93.7g (1.3mol), stirring are warming up to 60 DEG C, start that trichlorine oxygen is added dropwise
Phosphorus 207g (1.35mol) is dripped 65~85 DEG C of temperature control, time for adding 1h when dropwise addition and is warming up to 90 DEG C of heat preservation 1.5h.Reaction knot
Shu Hou, to the slightly cooling suction filtration of reaction solution, filter cake is triethylamine salt, is eluted with toluene 600ml, organic phase is merged, and is evaporated under reduced pressure
Remaining residue liquid is stirred cooling crystallization by toluene 1200ml out, and crystallization at 5 to 10 DEG C obtains product 414.6g, yield
88.5%.
The synthesis of 4 compound d of case study on implementation
2,2 '-thiobis (4- tertiary pentyl -6- tert-butyl phenol) 430g (1mol) is added in 3L there-necked flask, is added
Toluene 1100ml, triethylamine 550g (5.5mol), acrylic acid 96g (1.4mol), stirring are warming up to 60 DEG C, start that trichlorine oxygen is added dropwise
Phosphorus 207g (1.35mol) is dripped 65-85 DEG C of temperature control, time for adding 1h when dropwise addition and is warming up to 50 DEG C of heat preservation 3h.Reaction terminates
Afterwards, to the slightly cooling suction filtration of reaction solution, filter cake is triethylamine salt, is eluted with toluene 600ml, organic phase is merged, is evaporated under reduced pressure out
Remaining residue liquid is stirred cooling crystallization by toluene 1200ml, and crystallization at 5-10 DEG C filters, obtains product 414.6g, yield
90.5%.
The synthesis of 5 compound e of case study on implementation
2,2 '-thiobis (4,6- dibutylphenol) 430g (1mol) is added in 3L there-necked flask, toluene is added
1100ml, triethylamine 550g (5.5mol), acrylic acid 96g (1.4mol), stirring are warming up to 60 DEG C, start that phosphorus oxychloride is added dropwise
207g (1.35mol) is dripped 65-85 DEG C of temperature control, time for adding 1h when dropwise addition and is warming up to 50 DEG C of heat preservation 3h.After reaction,
To the slightly cooling suction filtration of reaction solution, filter cake is triethylamine salt, is eluted with toluene 600ml, organic phase is merged, toluene is evaporated under reduced pressure out
Remaining residue liquid is stirred cooling crystallization by 1200ml, and crystallization at 5-10 DEG C filters, obtains product 414.6g, yield 91.5%.
Above-described embodiment 1-5 is prepared into 2 antioxidant of antioxidant and 1 antioxidant 1010+DLTP of comparative example and comparative example
1010+168 is respectively applied in PP product, referring to standard GB/T/T1727-92, carries out sample preparation, long term thermal after the completion of sample preparation
(LTTS carries out performance comparison after experiment, as shown in table 1 referring to GB/T7141-2008) for oxygen aging experiment.The number from table
Show that the long-term thermal-oxidative aging property for adding the sample of 0.5% product of the present invention is about 10 times of blank sample according to comparing result, is
The traditional Hinered phenols of comparative example 1 add about 1.3 times of thioester antioxidant, are that the traditional Hinered phenols of comparative example 2 add phosphite ester
About 4 times of kind antioxidant have preferable antioxygenic property.
1. embodiment of table and comparative example antioxidant anti-aging property compare
1 compound a of embodiment is subjected to magnetic resonance detection, map is as shown in Figure 1, specifically parse as follows: δ 1.35-
9.44 (D, 9H, 3CH3)；δ 1.41-9.11 (D, 9H, 3CH3)；δ 2.20-3.00 (T, 3H, CH3)；δ 2.26-2.99 (T, 3H,
CH3)；δ 3.70-1.83 (S, 2H ,=CH2)；δ 6.1-0.98 (D, H ,=CH)；δ 6.45-0.97 (M, H, Ar-OH)；δ6.71-
1.56 (D, H, Ar-H)；δ 6.81-1.00 (D, H, Ar-H)；δ 7.11-0.99 (D, H, Ar-H)；δ 7.20-1.02 (D, H, Ar-
H).It can determine that the molecular structure of product is consistent with target compound according to above-mentioned data.
1 compound a of embodiment is subjected to liquid chromatographic detection, map is as shown in Fig. 2, the peak retention time of compound is
10.434min, and calculated by normalization method, purity 99.574%, purity is higher, and specific data are referring to table 2.
The liquid chromatogram concentration data of 2. embodiment of table, 1 compound a
| Peak number | Retention time | Area | Highly | Concentration |
| 1 | 2.673 | 1496 | 197 | 0.006 |
| 2 | 3.137 | 2942 | 713 | 0.012 |
| 3 | 3.247 | 8738 | 755 | 0.037 |
| 4 | 3.625 | 12794 | 1552 | 0.054 |
| 5 | 3.825 | 2746 | 398 | 0.012 |
| 6 | 4.581 | 3017 | 269 | 0.013 |
| 7 | 5.019 | 5626 | 255 | 0.024 |
| 8 | 7.239 | 48152 | 2742 | 0.203 |
| 9 | 8.145 | 6417 | 311 | 0.027 |
| 10 | 9.343 | 9030 | 461 | 0.038 |
| 11 | 10.434 | 23610885 | 1165433 | 99.574 |
| It amounts to | 23711842 | 1173086 |
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and
Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (6)
1. a kind of thioether class bis-phenol acrylate multiple-effect antioxidant, which is characterized in that it has the molecular structure as shown in formula I:
Wherein, R1Straight chain for C1-C5 or the alkyl with branch, R2Straight chain for C1-C5 or the alkyl with branch.
2. thioether class bis-phenol acrylate multiple-effect antioxidant according to claim 1, which is characterized in that it has such as formula a-
Molecular structure shown in e:
3. a kind of preparation method of thioether class bis-phenol acrylate multiple-effect antioxidant as claimed in claim 1 or 2, feature exist
In the steps include: for thioether class bisphenol compound to be dissolved in solvent, catalyst of triethylamine and acrylic acid be added, control temperature
It is 20 DEG C -50 DEG C, is stirred 0.5-1.5h, phosphorus oxychloride is added dropwise into reaction system, control time for adding is 50-90min,
It is warming up to 60 DEG C -90 DEG C after being added dropwise to complete, stirs lower reaction 1-4h, reaction solution is filtered, filter cake is eluted with normal heptane, to leaching
Washing lotion vacuum distillation, by vinasse at 0-5 DEG C stirring and crystallizing, filter again, collect filter cake to get.
4. according to the method described in claim 3, it is characterized in that, the thioether class bisphenol compound and acrylic acid, trichlorine oxygen
The mass ratio of the material of phosphorus is 1:(1.1-1.4): (1.1-1.5).
5. according to the method described in claim 3, it is characterized in that, the object of the thioether class bisphenol compound and the triethylamine
The amount ratio of matter is 1:(4-6).
6. according to the method described in claim 3, it is characterized in that, the solvent is toluene, dimethylbenzene, trimethylbenzene, benzene, positive heptan
One of alkane or n -nonane.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111689853A (en) * | 2020-06-28 | 2020-09-22 | 万华化学集团股份有限公司 | Layered bisphenol acrylate antioxidant and preparation method thereof |
| CN117417250A (en) * | 2023-10-14 | 2024-01-19 | 上海奇克氟硅材料有限公司 | Preparation method of antioxidant and antioxidant |
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| EP0322166A1 (en) * | 1987-12-23 | 1989-06-28 | Sumitomo Chemical Company, Limited | Phenolic compound and its use as a stabilizer for butadiene polymer |
| CA2026900A1 (en) * | 1989-10-06 | 1991-04-07 | Samuel Evans | Stabilised organic material |
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2019
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| JPS58124762A (en) * | 1982-01-16 | 1983-07-25 | Sumitomo Chem Co Ltd | Bisphenol derivative and its preparation |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111689853A (en) * | 2020-06-28 | 2020-09-22 | 万华化学集团股份有限公司 | Layered bisphenol acrylate antioxidant and preparation method thereof |
| CN111689853B (en) * | 2020-06-28 | 2023-03-03 | 万华化学集团股份有限公司 | Layered bisphenol acrylate antioxidant and preparation method thereof |
| CN117417250A (en) * | 2023-10-14 | 2024-01-19 | 上海奇克氟硅材料有限公司 | Preparation method of antioxidant and antioxidant |
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