CN115073815B - Environment-friendly heat stabilizer and preparation method thereof - Google Patents
Environment-friendly heat stabilizer and preparation method thereof Download PDFInfo
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- CN115073815B CN115073815B CN202210963856.3A CN202210963856A CN115073815B CN 115073815 B CN115073815 B CN 115073815B CN 202210963856 A CN202210963856 A CN 202210963856A CN 115073815 B CN115073815 B CN 115073815B
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- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
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Abstract
The invention belongs to the technical field of polyvinyl chloride heat stabilizers, and particularly relates to an environment-friendly heat stabilizer and a preparation method thereof. The heat stabilizer has both initial and long-term stabilizing effects when used, and has the advantages of simple process and low production cost, and meets the requirement of environmental protection.
Description
Technical Field
The invention belongs to the technical field of polyvinyl chloride heat stabilizers, and particularly relates to an environment-friendly heat stabilizer and a preparation method thereof.
Background
Polyvinyl chloride (PVC) plastics have excellent performance and low price, are widely applied, account for about 40 percent of the whole plastic consumption, and are second class plastic products with the yield second to that of polyethylene in the world at present. In the production and use processes of PVC, HCl removal reaction can occur, and the degradation of the PVC is easily initiated. In order to retard or prevent the zipper-type degradation of PVC molecules during thermal processing and to extend the service life of the product, heat stabilizers are often added during PVC processing. Thermal stabilizers include cadmium stabilizers, lead stabilizers, and calcium zinc stabilizers. However, cadmium and lead are heavy metals, which are highly toxic to human bodies and harmful to the environment, and thus, have been discarded.
The zinc-based composite heat stabilizer (such as a calcium stearate (CaSt 2)/zinc stearate (ZnSt 2) composite system) is applied in the market due to the non-toxic, low-cost characteristics and feasible stabilizing effect, and is a common stabilizer, zinc carboxylate in the stabilizer can react with free hydrogen chloride to form zinc chloride on one hand, and can replace chlorine atoms on polyvinyl chloride with carboxylic acid groups to form ester groups on the other hand, so that the polyvinyl chloride structure is stabilized, but the defects of poor initial colorability, rapid reduction of later-stage thermal stability and the like still exist, and the zinc chloride is strong Lewis acid, so that the zinc burning phenomenon is easily catalyzed during dechlorination of polyvinyl chloride at high temperature (170 ℃), specifically, the product has black spots or is completely blackened on the specific expression, and the defect greatly limits the application of the zinc-based composite heat stabilizer.
Uracil is a typical nitrogen-containing organic compound. A great deal of research has been conducted on nitrogen-containing organic compounds since the discovery by Sabaa et al of the university of Egyptian that barbituric acid and its derivatives can be used as heat stabilizers for PVC (Sabaa M W, mohamed N A, khalil K D, et al Polymer Degradation & Stabilty, 2000, 70 (2): 121-133.). The inventors studied the thermal stability efficiency of a series of barbituric acid and derivatives thereof as rigid PVC, and found that nitrogen-containing organic matters with different substituents can selectively absorb HCl gas, but can capture free radicals or remove unstable chlorine atoms from self-stable parts or chemically bond to unstable active sites, so as to block the number of conjugated sequences and inhibit coloring and HCl removal in a zipper mode. Meanwhile, the nitrogen-containing organic matters can generate good synergistic effect when being compounded with various heat stabilizers.
The rare earth composite stabilizer is also a new trend for the development of the stabilizer, the rare earth composite is synthesized by taking carboxylate or fatty acid salt of rare earth elements as a main component, and contains a proper amount of rare earth metal components.
Therefore, the rare earth stabilizer prepared by combining the uracil derivative with the rare earth hydrate is combined with the zinc-based stabilizer to be used as the composite main stabilizer, so that the problem of zinc burning is innovatively solved, the initial hue is fixed, and the good thermal processing stability is shown.
Disclosure of Invention
The invention aims to provide an environment-friendly heat stabilizer and a preparation method thereof, wherein the heat stabilizer has good initial and long-term heat stability and long high-temperature and aging resistance time.
In order to achieve the purpose, the invention provides the following technical scheme: the environment-friendly heat stabilizer comprises a terbium-based main stabilizer, wherein the terbium-based main stabilizer is a terbium-containing product represented by a structural formula II, and the chemical formula of the terbium-based main stabilizer is as follows: tb (I) (Ac) 3· xH 2 O, wherein x =0-10,
structural formula II.
Preferably, the environment-friendly heat stabilizer comprises 1-2 parts of terbium-based main stabilizer, 1-3 parts of zinc stearate main stabilizer, 1-3 parts of auxiliary heat stabilizer, 0.2-2 parts of lubricant and 0-5 parts of plasticizer based on 100 parts of polyvinyl chloride.
Preferably, the auxiliary heat stabilizer comprises at least one of tris (hydroxymethyl) aminomethane and epoxy fatty acid methyl ester, tris (hydroxymethyl) aminomethane is a novel environment-friendly pure organic heat stabilizer, has good initial whiteness and long-acting heat stability when in use, and is an excellent synergistic heat stabilizer of amino uracil derivatives; the epoxy fatty acid methyl ester plays a synergistic role with metal ions and other main components in the components.
Preferably, the lubricant is at least one of paraffin wax and polyethylene wax, and the plasticizer is one or more of dibutyl phthalate, dioctyl adipate, dibutyl sebacate and isooctyl oleate.
Preferably, the preparation method of the environment-friendly heat stabilizer comprises the step of synthesizing amino uracil glutamate serving as a ligand shown in a structural formula I and terbium acetate hydrate, wherein the structural formula I is shown as follows:
the structural formula I.
Preferably, the preparation method of the environment-friendly heat stabilizer comprises the following steps: (1) Heating 5-aminouracil and glutamic acid in a condensation reagent N, N' -dicyclohexylcarbodiimide for reaction at the temperature of 70-120 ℃ for 2-5 h, centrifuging, washing and drying a reaction product to obtain aminouracil glutamate shown in a structural formula I, wherein the aminouracil derivative can replace unstable chlorine atoms through amino groups and other groups in the processing process to absorb HCl molecules and improve the overall thermal stability of the product; (2) Reacting amino uracil glutamate shown in a structural formula I with hydrated terbium acetate in kerosene for 1-8 h, carrying out suction filtration and drying on a reaction product to obtain a terbium-based main stabilizer shown in a structural formula II, wherein carboxyl is a common ligand for synthesizing a rare earth complex, particularly a carboxyl ligand with an aromatic ring, and has rigidity and stability in structure, oxygen atoms with negative charges in the ligand can be coordinated with rare earth ions, nitrogen in N-acylated amino acid and oxygen in acyl do not participate in coordination, and the reaction is carried out in the kerosene.
In the reaction, the mol ratio of 5-aminouracil to glutamic acid is 1:1-2, and the mol ratio of aminouracil glutamate shown in a structural formula I to terbium acetate hydrate is 1-1.5.
Preferably, the preparation method of the environment-friendly heat stabilizer comprises the steps of mixing, grinding, stirring, mixing and plasticizing terbium-based main stabilizer, zinc stearate main stabilizer, auxiliary heat stabilizer, lubricating plasticizer and plasticizer, and then adding and uniformly mixing the mixture with polyvinyl chloride.
Compared with the prior art, the invention has the beneficial effects that:
1. the heat stabilizer has excellent static and dynamic thermal stability, simple preparation process, low cost, no toxicity and environmental protection, completely meets the requirements of green environmental protection, energy conservation and emission reduction of current chemical products, can replace liquid heat stabilizers such as barium, cadmium, zinc, calcium, zinc and the like in the market, and has wide market prospect.
2. The heat stabilizer compound prepared by matching terbium-based main stabilizer and zinc stearate has excellent zinc burning resistance when used, can maintain initial hue while delaying the occurrence of zinc burning, and improves the long-acting thermal stability of PVC.
3. The terbium-based main stabilizer is generated by reacting amino uracil derivatives with glutamic acid and then reacting with hydrated terbium acetate, and can absorb HCl molecules to show good thermal stability on one hand; on the other hand, carbon-oxygen double bonds on the molecular chain can generate Diels-Alder addition reaction with double bonds in a PVC structure, so that the formation of a conjugated sequence is damaged, the further degradation and coloring of PVC are inhibited, and the carbon-oxygen double bonds are bonded to the PVC molecular chain through chemical bonds, so that the stability of reproduced products is improved.
Drawings
FIG. 1 is a diagram of the condensation reaction equation of 5-aminouracil with glutamic acid;
FIG. 2 is a graph of the reaction equation for aminouracil glutamate with terbium acetate hydrate;
FIG. 3 is an infrared spectrum of aminouracil glutamate;
FIG. 4 is an infrared spectrum of a terbium-based primary stabilizer.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. The following description of at least one exemplary embodiment is merely illustrative in nature and is in no way intended to limit the invention, its application, or uses. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The relative arrangement of the components and steps, the numerical expressions and numerical values set forth in these embodiments do not limit the scope of the present invention unless specifically stated otherwise. Techniques, methods, and apparatus known to those of ordinary skill in the relevant art may not be discussed in detail but are intended to be part of the specification where appropriate. In all examples shown and discussed herein, any particular value should be construed as merely illustrative, and not limiting. Thus, other examples of the exemplary embodiments may have different values.
Embodiments of the present invention will be described in detail below with reference to specific examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were carried out according to conventional conditions or conditions recommended by the manufacturer.
The invention provides an environment-friendly heat stabilizer, which comprises a terbium-based main stabilizer,the terbium-based main stabilizer is a terbium-containing product represented by a structural formula II, and the chemical formula of the terbium-based main stabilizer is as follows: tb (I) (Ac) 3· xH 2 O, wherein x =0-10,
structural formula II.
Specifically, the preparation method of the terbium-based main stabilizer is to synthesize the amino uracil glutamate shown in a structural formula I as a ligand and terbium acetate hydrate.
Structural formula I.
Further, the preparation method of the terbium-based main stabilizer comprises the following steps: (1) Heating 5-aminouracil and glutamic acid in a condensation reagent N, N' -dicyclohexylcarbodiimide for reaction, centrifuging, washing and drying a reaction product to obtain aminouracil glutamate shown in a structural formula I; (2) Reacting aminouracil glutamate shown in a structural formula I with hydrated terbium acetate in kerosene, and performing suction filtration and drying on a reaction product to obtain a terbium-based main stabilizer shown in a structural formula II, wherein the heating reaction temperature in the step (1) is 70-120 ℃, and the reaction time is 2-5 hours; the reaction time in the step (2) is 1-8 h.
Furthermore, the molar ratio of the 5-aminouracil to the glutamic acid is 1:1-2, and the molar ratio of the structural formula I to the hydrated terbium acetate is 1-1.5.
Furthermore, the environment-friendly heat stabilizer comprises 1-2 parts of terbium-based main stabilizer, 1-3 parts of zinc stearate main stabilizer, 1-3 parts of auxiliary heat stabilizer, 0.2-2 parts of lubricant and 0-5 parts of plasticizer according to 100 parts of polyvinyl chloride, wherein the auxiliary heat stabilizer comprises at least one of trihydroxymethyl aminomethane and epoxy fatty acid methyl ester, the lubricant is at least one of paraffin and polyethylene wax, and the plasticizer is one or more of dibutyl phthalate, dioctyl adipate, dibutyl sebacate and isooctyl oleate.
The invention also provides a preparation method of the environment-friendly heat stabilizer, which comprises the following steps: mixing terbium-based main stabilizer, zinc stearate main stabilizer, auxiliary heat stabilizer, lubricant and plasticizer, grinding, stirring, mixing and plasticizing, and then adding and uniformly mixing with polyvinyl chloride.
In order to better illustrate the invention, the following specific examples are also provided.
Example 1:
1. preparation of Terbium-based Primary stabilizer
(1) Adjusting the pH value to be alkaline, heating 5-aminouracil and glutamic acid to 100 ℃ in a condensation reagent N, N' -dicyclohexylcarbodiimide according to a molar ratio of 1:1 for reacting for 3 hours, centrifuging, washing and drying a reaction product to obtain aminouracil glutamate shown in a structural formula I;
(2) And (2) immersing the amino uracil glutamate shown in the structural formula I in the step (1) into kerosene, adding terbium acetate hydrate to react for 4 hours, and performing suction filtration and drying on a reaction product to obtain a terbium-based main stabilizer shown in a structural formula II, wherein the reaction molar ratio of the amino uracil glutamate shown in the structural formula I to the terbium acetate hydrate is 1:2.
Infrared spectrum measurement is carried out on the prepared structural formula I and the structural formula II, and the characterization results are as follows:
infrared spectroscopy FTIR of aminouracil glutamate: 3026cm -1 （NH 2 ），2879cm -1 (alkyl), 1330cm -1 （C-N），1732cm -1 /1623cm -1 （C=O）。
Infrared spectrum FTIR of terbium-based primary stabilizer: 3380cm -1 （NH 2 ），2960cm -1 (alkyl group) 1320cm -1 （C-N），1758cm -1 /1683cm -1 （C=0），3430cm -1 （O-H）。
2. Preparation of PVC Material
The formula is as follows: 100 parts of polyvinyl chloride, tb (I) (Ac) 3· xH 2 The adhesive comprises the following components, by weight, 1.5 parts of O, wherein x =0, 2 parts of a zinc stearate main stabilizer, 2 parts of a trihydroxymethyl aminomethane and epoxy fatty acid methyl ester auxiliary heat stabilizer, 1 part of a paraffin lubricant and 2 parts of a dibutyl phthalate plasticizer.
Preparation: 1.5 parts of terbium-based main stabilizer, 2 parts of zinc stearate main stabilizer, 2 parts of trihydroxymethyl aminomethane and epoxy fatty acid methyl ester auxiliary heat stabilizer and 1 part of paraffin lubricant are mixed for 5min at a high speed, then 2 parts of dibutyl phthalate plasticizer and 100 parts of polyvinyl chloride are added and mixed for 5min on a double-roll open mill, and the plastication conditions are that the rotating speed of a front roll is 18r/min, the rotating speed of a rear roll is 20r/min, the roll temperature is 170 ℃, and sheets are discharged after complete plastication.
Example 2:
1. preparation of Terbium-based primary stabilizer
(1) Adjusting the pH value to be alkaline, heating 5-aminouracil and glutamic acid in a condensation reagent N, N' -dicyclohexylcarbodiimide according to a molar ratio of 1.5 to 120 ℃ for 2h, and centrifuging, washing and drying a first reaction product to obtain aminouracil glutamate shown in a structural formula I;
(2) And (2) immersing the amino uracil glutamate shown in the structural formula I of the product in the step (1) into kerosene, adding hydrated terbium acetate, reacting for 2 hours, performing suction filtration on the reaction product, and drying to obtain a terbium-based main stabilizer shown in the structural formula II, wherein the reaction molar ratio of the amino uracil glutamate shown in the structural formula I to the hydrated terbium acetate is 1.5.
2. Preparation of PVC Material
The formula is as follows: 100 parts of polyvinyl chloride, tb (I) (Ac) 3· xH 2 The coating comprises the following raw materials, by weight, O2 parts, wherein x =0, 3 parts of a zinc stearate main stabilizer, 3 parts of a trihydroxymethyl aminomethane and epoxy fatty acid methyl ester auxiliary heat stabilizer, 2 parts of a paraffin lubricant and 5 parts of a dibutyl phthalate plasticizer.
Preparation: mixing 2 parts of terbium-based main stabilizer, 3 parts of zinc stearate main stabilizer, 3 parts of tris (hydroxymethyl) aminomethane and epoxy fatty acid methyl ester auxiliary heat stabilizer and 2 parts of paraffin lubricant at high speed for 5min, then adding 5 parts of dibutyl phthalate plasticizer and 100 parts of polyvinyl chloride, and mixing for 5min on a double-roll open mill under the conditions that the rotation speed of a front roll is 18r/min, the rotation speed of a rear roll is 20r/min, the roll temperature is 170 ℃, and discharging sheets after complete plasticization.
Example 3:
1. preparation of Terbium-based primary stabilizer
(1) Adjusting the pH value to be alkaline, heating 5-aminouracil and glutamic acid in a condensation reagent N, N' -dicyclohexylcarbodiimide to 70 ℃ according to a molar ratio of 1:1 for reacting for 5 hours, centrifuging, washing and drying a reaction product to obtain aminouracil glutamate shown in a structural formula I;
(2) And (2) immersing the amino uracil glutamate shown in the structural formula I in the step (1) into kerosene, adding terbium acetate hydrate to react for 8 hours, and performing suction filtration and drying on a reaction product to obtain a terbium-based main stabilizer shown in a structural formula II, wherein the reaction molar ratio of the amino uracil glutamate shown in the structural formula I to the terbium acetate hydrate is 1:2.
2. Preparation of PVC Material
The formula is as follows: 100 parts of polyvinyl chloride, tb (I) (Ac) 3· xH 2 The coating comprises the following raw materials, by weight, 1 part of O1, wherein x =0, 1 part of zinc stearate main stabilizer, 1 part of trihydroxymethyl aminomethane and epoxy fatty acid methyl ester auxiliary heat stabilizer, 0.2 part of paraffin lubricant and 1 part of dibutyl phthalate plasticizer.
Preparation: mixing 1 part of terbium-based main stabilizer, 1 part of zinc stearate main stabilizer, 1 part of tris (hydroxymethyl) aminomethane and epoxy fatty acid methyl ester auxiliary heat stabilizer and 0.2 part of paraffin lubricant at high speed for 5min, then adding 1 part of dibutyl phthalate plasticizer and 100 parts of polyvinyl chloride, and mixing for 5min on a double-roll open mill under the conditions that the rotation speed of a front roll is 18r/min, the rotation speed of a rear roll is 20r/min, the roll temperature is 170 ℃, and discharging sheets after complete plasticization.
Example 4:
in contrast to example 3, the terbium-based primary stabilizer was Tb (I) (Ac) 3· xH 2 O, wherein x =6.
Example 5:
in contrast to example 3, the terbium-based primary stabilizer was Tb (I) (Ac) 3· xH 2 O, wherein x =10.
Comparative example 1:
the difference from example 3 is that the primary stabilizers are calcium stearate and zinc stearate, and the molar ratio of calcium stearate to zinc stearate is 2:3.
The mixtures of the primary stabilizer, the secondary stabilizer and the lubricant in examples 1 to 5 and comparative example 1 were measured for static thermal stability according to the Congo Red method of national Standard GB/T2917.1-2002, respectively.
The PVC material was prepared by starting the two roll mill until a black color appeared on the rolls and the time to plastication was recorded as the dynamic thermal stability time. The results are shown in Table 1.
From the results, compared with the comparative example of the calcium-zinc stabilizer, the embodiment of adding the terbium-based main stabilizer can obviously improve the long-term thermal stabilization effect of the PVC product, and the heat stabilizer can well ensure the initial hue in the use process, the static stabilization time is 20-50min, the dynamic stabilization time is 40-80min, and the zinc burning phenomenon can be inhibited.
Comparative example 1 in the long term use will lead to more and more zinc chloride and can not be completely absorbed by calcium stearate, thus the polyvinyl chloride will generate 'zinc burning' phenomenon, the product will turn black, and the strength of the polyvinyl chloride product will be reduced, while calcium stearate will easily cause the polyvinyl chloride to generate more conjugated double bond structure, therefore the whole color will turn yellow.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (6)
1. An environment-friendly heat stabilizer comprises a terbium-based main stabilizer, and is characterized in that: the terbium-based primary stabilizer is a terbium-containing product represented by the structural formula II, as shown in the following figure, wherein x =0-10,
and structural formula II.
2. The environment-friendly heat stabilizer according to claim 1, wherein: the environment-friendly heat stabilizer comprises the following components in parts by weight, calculated according to 100 parts by weight of polyvinyl chloride: 1-2 parts of terbium-based main stabilizer, 1-3 parts of zinc stearate main stabilizer, 1-3 parts of auxiliary heat stabilizer, 0.2-2 parts of lubricant and 0-5 parts of plasticizer.
3. The environment-friendly heat stabilizer according to claim 2, wherein: the auxiliary heat stabilizer comprises at least one of tris (hydroxymethyl) aminomethane and epoxy fatty acid methyl ester.
4. The environment-friendly heat stabilizer according to claim 2, wherein: the lubricant is at least one of paraffin and polyethylene wax, and the plasticizer is one or more of dibutyl phthalate, dioctyl adipate, dibutyl sebacate and isooctyl oleate.
5. A method for preparing the environment-friendly heat stabilizer as claimed in claim 2, wherein: comprises the step of synthesizing the terbium-based main stabilizer by adopting amino uracil glutamate shown in a structural formula I as a ligand and hydrated terbium acetate,
structural formula I
The specific operation steps are as follows:
adjusting the pH value to be alkaline, heating 5-aminouracil and glutamic acid in a condensation reagent N, N' -dicyclohexylcarbodiimide for reaction at the temperature of 70-120 ℃ for 2-5 h, centrifuging, washing and drying the reaction product to obtain aminouracil glutamate shown in the structural formula I;
reacting aminouracil glutamate shown in a structural formula I with hydrated terbium acetate in kerosene for 1-8 h, and performing suction filtration and drying on a reaction product to obtain a terbium-based main stabilizer shown in a structural formula II;
in the reaction, the molar ratio of 5-aminouracil to glutamic acid is 1:1-2, and the molar ratio of aminouracil glutamate shown in a structural formula I to terbium acetate hydrate is 1-1.5.
6. The method for preparing the environment-friendly heat stabilizer according to claim 5, wherein the method comprises the following steps: the preparation method comprises the steps of mixing, grinding, stirring, mixing and plasticizing terbium-based main stabilizer, zinc stearate main stabilizer, auxiliary heat stabilizer, lubricant and plasticizer.
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| JPH05156104A (en) * | 1991-12-10 | 1993-06-22 | Nissan Fuero Yuki Kagaku Kk | Novel halogenated resin composition |
| US6156830A (en) * | 1998-06-26 | 2000-12-05 | Witco Vinyl Additives Gmbh | 5-substituted 6-aminouracils as stabilizers for halogenated polymers |
| CN106633469A (en) * | 2016-10-08 | 2017-05-10 | 深圳市志海实业股份有限公司 | Preparation and application of novel environment-friendly uracil zinc compound stabilizers for PVC (polyvinyl chloride) pipes |
| CN110003522A (en) * | 2019-03-15 | 2019-07-12 | 广东工业大学 | A kind of PVC organic composite heat stabilizer and PVC product and preparation method thereof |
| CN111662481A (en) * | 2020-06-30 | 2020-09-15 | 内蒙古科技大学 | Uracil-rare earth composite stabilizer for PVC (polyvinyl chloride) and preparation method thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05156104A (en) * | 1991-12-10 | 1993-06-22 | Nissan Fuero Yuki Kagaku Kk | Novel halogenated resin composition |
| US6156830A (en) * | 1998-06-26 | 2000-12-05 | Witco Vinyl Additives Gmbh | 5-substituted 6-aminouracils as stabilizers for halogenated polymers |
| CN106633469A (en) * | 2016-10-08 | 2017-05-10 | 深圳市志海实业股份有限公司 | Preparation and application of novel environment-friendly uracil zinc compound stabilizers for PVC (polyvinyl chloride) pipes |
| CN110003522A (en) * | 2019-03-15 | 2019-07-12 | 广东工业大学 | A kind of PVC organic composite heat stabilizer and PVC product and preparation method thereof |
| CN111662481A (en) * | 2020-06-30 | 2020-09-15 | 内蒙古科技大学 | Uracil-rare earth composite stabilizer for PVC (polyvinyl chloride) and preparation method thereof |
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