CN111925358B - Light stabilizer and preparation process thereof - Google Patents
Light stabilizer and preparation process thereof Download PDFInfo
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- CN111925358B CN111925358B CN202010574977.XA CN202010574977A CN111925358B CN 111925358 B CN111925358 B CN 111925358B CN 202010574977 A CN202010574977 A CN 202010574977A CN 111925358 B CN111925358 B CN 111925358B
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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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/04—Homopolymers or copolymers of ethene
- C08J2323/06—Polyethene
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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
Abstract
The invention discloses a light stabilizer with antioxidant and light stabilizing effects and a preparation process thereof, wherein 4,4' -diaminodiphenylamine, 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine and alkali are used as raw materials, an organic solvent is used as a reaction solvent, and the reaction is assisted by controlling the reaction temperature and adjusting a proper feed ratio so as to synthesize the multifunctional light stabilizer; the polymer has good intermiscibility with most industrial solvents and excellent high-molecular intermiscibility, can slow down the aging and decomposition of plastic films, rubber products or coatings and prolong the service life when added into the plastic films, the rubber products or the coatings, and can also be used as a free radical trapping agent to play a role of an antioxidant when added into lubricating oil; in the processing and using process, no special smell is generated, the original color of the material is not influenced, the material is high temperature resistant, difficult to volatilize, excellent in stability and low in price.
Description
Technical Field
The invention belongs to the field of polymer material modified plastic additives, and particularly relates to a light stabilizer and a preparation process thereof.
Background
The light stabilizer is an additive of high molecular products, which can shield or absorb the energy of ultraviolet rays, quench singlet oxygen and decompose hydroperoxide into inactive substances, etc., so that the possibility of photochemical reaction can be eliminated or slowed down, and the process of photoaging can be prevented or delayed under the radiation of light, thereby achieving the purpose of prolonging the service life of the high molecular products.
Aromatic amine antioxidants, also known as rubber antioxidants, are the most abundant in production, are low in price and have remarkable antioxidant effect, but due to discoloration of products, the application of the aromatic amine antioxidants in light-colored and white products is limited, and the aromatic amine antioxidants are mainly used in plastics, synthetic fibers, latex, petroleum products, foods, medicines and cosmetics. Important aromatic amine antioxidants comprise compounds such as diphenylamine, p-phenylenediamine and dihydroquinoline and derivatives or polymers thereof, can be used in products such as natural rubber, styrene-butadiene rubber, chloroprene rubber and isoprene rubber, and can stop or inhibit a chain initiation reaction and a chain growth reaction by capturing peroxy radicals so as to terminate a free radical chain reaction and achieve the aim of preventing oxidation.
The light stabilizer provided by the invention has double effects of the light stabilizer and the aromatic amine antioxidant.
Disclosure of Invention
The invention solves the technical problems of easy migration of hindered amine molecules, poor compatibility with industrial solvents, single functionality and the like in the prior art.
In order to solve the problems, the technical scheme of the invention is as follows:
a light stabilizer of the formula:
the reaction equation of the above light stabilizer is as follows:
preferably, the preparation method of the light stabilizer takes 4,4' -diaminodiphenylamine, 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine and base as raw materials and comprises the following steps:
(1) preparing a solution of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine with the mass fraction of 40%;
(2) adding an organic solvent into 4,4' -diaminodiphenylamine, and stirring;
(3) heating, dropwise adding the 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine solution obtained in the step (1) into the mixed solution obtained in the step (2), and adding alkali liquor for reaction after dropwise adding;
(4) and after the reaction is finished, washing and layering to obtain an organic layer, cooling, crystallizing and filtering to obtain the light stabilizer.
Preferably, the mass ratio of the 4,4' -diaminodiphenylamine, the 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine, the base and the organic solvent is 1:5.3-5.5:0.41-0.61: 3-6.
Preferably, the organic solvent in step (1) is any one of xylene, toluene, N-dimethylformamide and tetrahydrofuran.
Preferably, the alkali in the step (3) is sodium hydroxide or potassium hydroxide.
Preferably, in the step (3), the dropping temperature is 65-90 ℃, and the dropping time is 3-6 h.
Preferably, the temperature for reaction by adding alkali liquor in the step (3) is 90-120 ℃, and the reaction time is 4-8 h.
Preferably, the temperature of the cooling crystallization in the step (4) is-5 ℃ to 10 ℃.
Compared with the prior art, the invention has the following advantages:
the light stabilizer provided by the invention is used as a multifunctional light stabilizer, has good intermiscibility with most industrial solvents and excellent polymer intermiscibility, and can slow down aging and decomposition and prolong the service life when being added into plastics, rubber or paint; in the processing and using process, no special smell is generated, the original color of the material is not influenced, the material is high-temperature resistant, difficult to volatilize and excellent in stability; and has the advantage of low price in the light stabilizer with the same function; can also be used as amine antioxidant by forming Ar2NO, capture peroxy radicals to prevent or inhibit chain initiation and chain growth reactions, thereby terminating free radical chain reactions and achieving the purpose of preventing oxidation.
The light stabilizer of the invention has simple preparation process and low raw material price, and can be widely used for industrial production.
Detailed Description
Example 1:
a process for the preparation of a light stabilizer comprising the steps of:
adding xylene into 53g of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine to prepare a solution of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine with the mass fraction of 40% for later use;
adding 10g of 4,4' -diaminodiphenylamine into a reactor, adding 30g of xylene, and stirring to dissolve the xylene;
raising the temperature to 65 ℃, dropwise adding 40 mass percent of 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine solution into a reactor within 3 hours, adding 20.5g of 20 percent sodium hydroxide solution after dropwise adding, and continuously keeping the temperature at 90 ℃ for reacting for 4 hours; after the reaction is finished, the temperature is reduced, the water is washed, an organic layer is obtained by water separation, the temperature is reduced by 10 ℃ for crystallization, solid is obtained by filtration, 56.4g is weighed after drying, and the product yield is 93.6%.
Example 2:
a process for the preparation of a light stabilizer comprising the steps of:
adding dimethylbenzene into 107g of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine to prepare a liquid solution of the 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine with the mass fraction of 40% for later use;
adding 20g of 4,4' -diaminodiphenylamine into a reactor, adding 70g of xylene, and stirring to dissolve the xylene;
raising the temperature to 70 ℃, dropwise adding 40 mass percent of 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine solution into a reactor within 4 hours, adding 45g of sodium hydroxide solution with the concentration of 20 percent after dropwise adding, and continuously keeping the temperature at 95 ℃ for reacting for 5 hours; after the reaction is finished, the temperature is reduced, the water is washed, an organic layer is obtained by water separation, the temperature is reduced by 5 ℃ for crystallization, solid is obtained by filtration, 113.5g is weighed after drying, and the product yield is 94.2%.
Example 3:
a process for the preparation of a light stabilizer comprising the steps of:
189g of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine is added with toluene to prepare a solution of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine with the mass fraction of 40% for later use;
adding 35g of 4,4' -diaminodiphenylamine into a reactor, adding 140g of toluene, and stirring to dissolve the toluene;
raising the temperature to 75 ℃, dropwise adding 40 mass percent of 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine solution into the reactor within 5 hours, adding 87.5g of sodium hydroxide solution with the concentration of 20 percent after dropwise adding, and continuously keeping the temperature at 100 ℃ for reacting for 6 hours; after the reaction is finished, cooling and washing, dividing water to obtain an organic layer, cooling to 3 ℃ for crystallization, filtering to obtain a solid, drying, weighing 199.9g, and obtaining the product with the yield of 94.8%.
Example 4:
a process for the preparation of a light stabilizer comprising the steps of:
272.5g of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine is added with toluene to prepare a solution of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine with the mass fraction of 40% for later use;
adding 50g of 4,4' -diaminodiphenylamine into a reactor, adding 220g of toluene, and stirring to dissolve the toluene;
raising the temperature to 80 ℃, dropwise adding 40 mass percent of 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine solution into a reactor within 5 hours, adding 125g of sodium hydroxide solution with the concentration of 20 percent after dropwise adding, and continuously preserving the temperature at 105 ℃ for reacting for 6 hours; after the reaction is finished, cooling and washing, dividing water to obtain an organic layer, cooling to 0 ℃ for crystallization, filtering to obtain a solid, drying, weighing 282.6g, and obtaining the product with the yield of 93.8%.
Example 5:
a process for the preparation of a light stabilizer comprising the steps of:
548g of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine is added into toluene to prepare a solution of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine with the mass fraction of 40% for later use; adding 100g of 4,4' -diaminodiphenylamine into a reactor, adding 500g of toluene, and stirring to dissolve the toluene;
raising the temperature to 85 ℃, dropwise adding 40 mass percent of 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine solution into the reactor within 5.5 hours, adding 240g of sodium hydroxide solution with the concentration of 20 percent after dropwise adding, and continuously preserving the temperature at 115 ℃ for reaction for 7 hours; after the reaction is finished, cooling and washing, dividing water to obtain an organic layer, cooling to 0 ℃ for crystallization, filtering to obtain a solid, drying, weighing 573.6g, and obtaining the product with the yield of 95.2%.
Example 6:
a process for the preparation of a light stabilizer comprising the steps of:
825g of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine is added into toluene to prepare a solution of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine with the mass fraction of 40% for later use; adding 4,4' -diaminodiphenylamine 150g into a reactor, adding toluene 900g, and stirring to dissolve the toluene;
raising the temperature to 90 ℃, dropwise adding 40 mass percent of 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine solution into a reactor within 6 hours, adding 457.5g of sodium hydroxide solution with the concentration of 20 percent after dropwise adding, and continuously preserving the temperature at 120 ℃ for reacting for 8 hours; after the reaction is finished, cooling and washing, dividing water to obtain an organic layer, cooling to 0 ℃ for crystallization, filtering to obtain a solid, drying, weighing 850.4g, and obtaining the product with the yield of 94.1%.
Example 7
The light stabilizer prepared in example 5 was added to PE material in the proportions of 0.2%, 0.5% and 1.0%, respectively, and blown to form plastic films with a thickness of about 0.09mm, respectively, and the tensile strength and elongation at break were measured in accordance with GB/T13022-1991 (aging conditions: lamp type: UVB-340; irradiance (340 nm): 0.76W/m)2(ii) nm; black mark temperature: 60 +/-3 ℃/50 +/-3 ℃; light/condensation cycle: 480min/240min)。
Unaged performance test:
| test items | Virgin PE material | Adding 0.2% of PE | Adding 0.5% of PE | Adding 0.7% of PE |
| Elongation at break% | 724 | 719 | 729 | 738 |
| Tensile strength MPa | 18.16 | 18.51 | 17.79 | 17.38 |
Aging for 800 h:
| test items | Virgin PE material | Adding 0.2% of PE | Adding 0.5% of PE | Adding 0.7% of PE |
| Elongation at break% | 527 | 687 | 695 | 699 |
| Tensile strength MPa | 15.20 | 16.42 | 16.74 | 16.77 |
Aging for 1200 h:
| test items | Virgin PE material | Adding 0.2% of PE | Adding 0.5% of PE | Adding 0.7% of PE |
| Elongation at break% | 357 | 592 | 646 | 681 |
| Tensile strength MPa | 11.50 | 14.41 | 14.95 | 15.05 |
According to the test results, the elongation at break and tensile strength of the PE material without the light stabilizer of the invention are gradually reduced along with the aging time; when the PE material is not aged, the elongation at break and the tensile strength of the PE material added with the light stabilizer with different concentrations are not obviously changed, and the elongation at break and the tensile strength of the PE material added with the light stabilizer are better along with the increase of the aging time, which shows that the light stabilizer has excellent aging resistance.
Example 8
The light stabilizer and the antioxidant 1010 prepared in the example 5 are respectively mixed with the auxiliary antioxidant 168 according to the proportion of 1: 2, then the mixture is respectively added into PE material according to the proportion of 2 percent, then the PE material sample is pressed into a test sample with the thickness of 250 +/-15 μm, 5-10mg of the sample is accurately weighed, and the oxidation induction time is measured by DSC (differential scanning calorimeter) according to the ISO11357-6:2002 standard as follows:
according to the test results, the following results are obtained: a. the thermal oxidation protection effect of the PE material without the antioxidant and the PE material with the antioxidant formula is longer under the same temperature; b. the antioxidant formula with the same proportion and the same quantity is added into PE, and the main antioxidant is found to be a light stabilizer formula of the invention, and compared with the main antioxidant of 1010 formula, the light stabilizer formula has a more lasting thermal oxidation protection effect at the same temperature; c. at 220 ℃, the PE added with the product of the invention as the main antioxidant formula has higher hot working temperature.
The combination of example 7 and example 8 shows that the light stabilizer of the present invention has excellent light stability and antioxidant property.
It should be noted that all the above-mentioned embodiments are only preferred embodiments of the present invention, and are not intended to limit the scope of the present invention, and all the equivalent substitutions or substitutions made on the above-mentioned basis are included in the scope of the present invention.
Claims (9)
1. A light stabilizer characterized by the structural formula:
2. the preparation method of the light stabilizer according to claim 1, characterized in that the synthesis process route of the preparation method is as follows:
3. the preparation method according to claim 2, comprising the following specific steps:
(1) preparing a solution of 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine with the mass fraction of 40%;
(2) adding an organic solvent into 4,4' -diaminodiphenylamine and stirring;
(3) heating, dropwise adding the 2-chloro-4, 6-di- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine solution obtained in the step (1) into the mixed solution obtained in the step (2), and adding alkali liquor for reaction after dropwise adding;
(4) and after the reaction is finished, washing and layering to obtain an organic layer, cooling, crystallizing and filtering to obtain the light stabilizer.
4. The production method according to claim 3, characterized in that: the mass ratio of the 4,4' -diaminodiphenylamine, the 2-chloro-4, 6-bis- [ N-butyl- (2,2,6, 6-tetramethyl-4-piperidyl) amino ] -1,3, 5-triazine, the alkali and the organic solvent is 1:5.3-5.5:0.41-0.61: 3-6.
5. The production method according to claim 3, characterized in that: the organic solvent in the step (2) is any one of xylene, toluene, N-dimethylformamide and tetrahydrofuran.
6. The production method according to claim 3, characterized in that: and (3) the alkali in the step (3) is sodium hydroxide or potassium hydroxide.
7. The production method according to claim 3, characterized in that: in the step (3), the dropping temperature is 65-90 ℃, and the dropping time is 3-6 h.
8. The production method according to claim 3, characterized in that: and (3) adding alkali liquor to react at the temperature of 90-120 ℃ for 4-8 h.
9. The production method according to claim 3, characterized in that: the temperature of the cooling crystallization in the step (4) is-5 ℃ to 10 ℃.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4433145A (en) * | 1979-11-06 | 1984-02-21 | Hoechst Aktiengesellschaft | Triazine stabilizers |
| US4843159A (en) * | 1986-06-16 | 1989-06-27 | Ciba-Geigy Corporation | Triazine derivatives of piperidinylamidines |
| US5047531A (en) * | 1988-08-04 | 1991-09-10 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
| CN1753871A (en) * | 2003-02-26 | 2006-03-29 | 西巴特殊化学品控股有限公司 | Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4433145A (en) * | 1979-11-06 | 1984-02-21 | Hoechst Aktiengesellschaft | Triazine stabilizers |
| US4843159A (en) * | 1986-06-16 | 1989-06-27 | Ciba-Geigy Corporation | Triazine derivatives of piperidinylamidines |
| US5047531A (en) * | 1988-08-04 | 1991-09-10 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
| CN1753871A (en) * | 2003-02-26 | 2006-03-29 | 西巴特殊化学品控股有限公司 | Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines |
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