CN109988382A - A kind of PVC heat stabilizer composition, preparation method and its application method - Google Patents
A kind of PVC heat stabilizer composition, preparation method and its application method Download PDFInfo
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- CN109988382A CN109988382A CN201910269004.2A CN201910269004A CN109988382A CN 109988382 A CN109988382 A CN 109988382A CN 201910269004 A CN201910269004 A CN 201910269004A CN 109988382 A CN109988382 A CN 109988382A
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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
- 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
- C08L27/02—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 not modified by chemical after-treatment
- C08L27/04—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 not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
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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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Abstract
The invention discloses a kind of PVC heat stabilizer composition, preparation method and its application methods, composition includes dicarboxylic acids mercaptoethanol ester and the etherificate product that is etherified mercaptoethanol ylmethyl tin, and the mass percent of the etherificate product is 10%-80%.Preparation method includes the preparation of dicarboxylic acids mercaptoethanol ester, be etherified the preparation of product and the compounding of the two obtains PVC heat stabilizer composition, and when use can be used alone and can also be used together with hot auxiliary stabilizer.The present invention is that raw material just can be obtained without using isooctyl thioglycolate, and conventional thermal stabilizer can be directly substituted in PVC process and is come using and capable of obtaining excellent thermostable effect.
Description
Technical field
The present invention relates to a kind of heat stabilizer more particularly to PVC(polyvinyl chloride) produce the heat stabilizer combination used
Object, preparation method and its application method.
Background technique
In commercial applications, PVC is one of available most important thermoplastic in market.But it is also heat
Worst one of the polymer of stability.Halogen containing polymers, especially polyvinyl chloride are generally easy to draw by autoxidation generation heat
The performance degradation of hair, and in the process for increasing temperature, physical property degradation and color change can occur for polyvinyl chloride,
The case where changing with usual unwanted color of rear stage within beginning 5-10 minutes of the process that heats up.It is familiar to people
The plastics materials such as self-adhesive film, transparent packaging material, plastic tube, plastic window frame, plastics wooden partition, plastic bottles, plastic wall paper
A big chunk in material both is from pvc material, in order to make polyvinyl chloride not generation property in the process of processing and using
The case where energy degeneration and color change, people have done a large amount of work to study heat stabilizer.Series of stable agent can be used for
Stablize PVC.These PVC stabilizers are such as: lead salt stabilizer, mercaptan tin stabilizer, calcium-zinc composite stabilizing agent, rare-earth stabilizer and
Organic stabilizer etc..
Wherein, mercaptan tin stabilizer is wherein more efficient stabilizer.Mercaptan tin stabilizer is good with the transparency, stablizes
Significant effect, especially thiol methyl tin, have obtained relatively broad application.
But being rooted in the hearts of the people with environmental consciousness, the increased costs of environmental improvement, isooctyl thioglycolate is as mercaptan
The main production raw material of methyl tin increasingly can not meet the market demand in supply side, seriously affect thiol methyl tin
Production and development, there is an urgent need to a kind of can replace, similar tin stabilizers of property by people to meet production needs.
Therefore it develops one kind and does not need isooctyl thioglycolate as raw material, heat can be equally used as when PVC is processed
Stabilizer use, have the effect of in terms of thermal stability excellent heat stabilizer very it is necessary to.
Summary of the invention
The first object of the present invention is to provide a kind of PVC heat stabilizer composition, which does not use sulfydryl
2-ethyl hexyl ethanoate is that raw material just can be obtained, and conventional thermal stabilizer can directly be substituted to use and energy in PVC process
Enough obtain excellent thermostable effect.
In order to solve the above technical problems, the technical scheme adopted by the invention is that:
A kind of PVC heat stabilizer composition, it is characterised in that: including dicarboxylic acids mercaptoethanol ester and by mercaptoethanol ylmethyl
The mass percent of the etherificate product that tin is etherified, the etherificate product is 10%-80%.
Preferably, the mass percent of the etherificate product is 45%-60%.
The etherificate product is the mixture of one or more of compound of following four kinds of structural formulas:
Structure formula (I):
Structure formula (II):
Structure formula (III)
Structure formula (IV)
The mercaptoethanol ylmethyl tin is tri-thiol ethyl alcohol ylmethyl tin, 3-mercaptoethanol base stannous methide or both
Mixture.
The mercaptoethanol ylmethyl tin is reacted by methyl chloride tin aqueous solution with mercaptoethanol, using suitable lye by
The acid reacted away in system is gradually added, it is available after being separated, being dried.
The range request excessively that the mercaptoethanol ylmethyl tin is etherified carries out under the action of highly basic.
The highly basic is inorganic base, and the inorganic base is sodium hydroxide or potassium hydroxide etc., preferably sodium hydroxide.
The etherificate refers to that mercaptoethanol ylmethyl tin carries out intramolecular or intermolecular primary or repeatedly dehydration
The process of processing.
The dicarboxylic acids mercaptoethanol ester is that condensation reaction obtains in the presence of a catalyst with mercaptoethanol by dicarboxylic acids
The esterification products arrived.
The dicarboxylic acids is the straight-chain dicarboxylic acid that carbon atom number is 4-18 or corresponding acid anhydrides.
The dicarboxylic acids is the mixture of one or more of succinic acid, adipic acid, glutaric acid, laurel bisgallic acid.
The catalyst is the mixture that sodium bisulfate, p-methyl benzenesulfonic acid, stannous chloride one or more of are worked as.
Second goal of the invention of the invention is to provide the preparation method of above-mentioned PVC heat stabilizer composition, it is characterised in that:
This method include etherate preparation step, dicarboxylic acids mercaptoethanol ester preparation step and compounding step,
The etherate preparation step specifically:
Step 1, mercaptoethanol ylmethyl tin is prepared
Methyl chloride tin aqueous solution is reacted with mercaptoethanol, in reaction, alkaline reaction is added and falls the acid in system, then passes through
Separation obtains mercaptoethanol ylmethyl tin after being dried；
Step 2, etherification reaction
Mercaptoethanol ylmethyl tin is reacted under the action of highly basic, obtains yellowish viscous solid；
The dicarboxylic acids mercaptoethanol ester preparation step specifically:
Dicarboxylic acids and mercaptoethanol are subjected to lower condensation reaction under the effect of the catalyst, obtain colourless transparent liquid；
The compounding step, which refers to, mixes etherificate product with dicarboxylic acids mercaptoethanol ester, the combination obtained after mixing
In object, the mass percent for being etherified product is 10%-80%.
Third purpose of the present invention is to provide application method of the above-mentioned PVC heat stabilizer composition in PVC, specifically
Are as follows: the PVC heat stabilizer composition is separately added to be added to PVC together after mixing in PVC or with auxiliary heat stabilizer
In.
When the PVC heat stabilizer composition is separately added in PVC, tin element contained by PVC heat stabilizer composition
Mass percent controls between 2%-39%.
Preferably, the mass percent of tin element contained by PVC heat stabilizer composition controls between 5%-31%.
When the PVC heat stabilizer composition is separately added in PVC, tin element contained by PVC heat stabilizer composition with
The molar ratio of element sulphur controls between 1:2-1:25.
Preferably, tin element and element sulphur contained by PVC heat stabilizer composition molar ratio control 1:4-1:15 it
Between.
The auxiliary heat stabilizer includes but is not limited to one of following description or several combinations.For example, ring
Oxygen soybean oil, phosphite ester, polyalcohol, hypophosphites, sterically hindered amines, glycidyl compound, phenol antioxidant etc..
The auxiliary heat stabilizer for the present invention in, content control in 1%-15%, convenient content be guarantee 3%-8% it
Between.
When the PVC heat stabilizer composition is separately added in PVC, it is mixed that the dosage of PVC heat stabilizer composition accounts for PVC
Close the 0.01%-1.3% of quality of material.
Preferably, the dosage of PVC heat stabilizer composition accounts for the 0.7%-1.3% of PVC mixture material quality.
Except above-mentioned requirements are, the application method of heat stabilizer composition provided by the invention makes with existing tin stabilizer
It is similar with method.Special means or technique are needed not move through to realize.
Compared with prior art, the invention has the following advantages:
The beneficial effects of the present invention are: the present invention provides the novel sn-containing compound composition of one kind for the first time and adds in PVC
Working hour is used as heat stabilizer.The heat stabilizer composition and primary raw material -- the sulfydryl second used without using current thiol methyl tin
The different monooctyl ester of acid, but used in liberal supply mercaptoethanol as primary raw material.It is extremely tight in the supply of isooctyl thioglycolate
In the case where, a kind of very effective alternative solution is provided.Due to using mercaptoethanol as primary raw material, and do not use
Isooctyl thioglycolate not only reduces the pollution to environment, and source is more extensive, reduces the production of PVC heat stabilizer
Cost.
Specific embodiment
The present invention will be further described with reference to the examples below, and described embodiment is only present invention a part
Embodiment is not whole embodiment.Based on the embodiments of the present invention, those skilled in the art are not making
Other embodiments used obtained, belong to protection scope of the present invention under the premise of creative work.
Embodiment 1
Step 1, the preparation of mercaptoethanol ylmethyl tin
By the aqueous solution for the methyl chloride tin (wherein monomethyl tin trichloride accounts for 31.97%) that chlorine ion concentration is 6.578mol/L
431 grams, 160 grams of mercaptoethanol are added to in churned mechanically 2000ml there-necked flask, under room temperature with 15% ammonium hydroxide be slowly added dropwise to
System is micro- white, stands 2 hours, and layering, top is divided into the water layer for having dispersed portion of product, retains wait be further processed；Lower layer is
Organic layer.It separates to rotate under the conditions of being placed on 105 DEG C of oil baths, -0.98MPa and be dried.Organic liquor after being dried
266.7 grams of body.
Step 2, the etherificate of mercaptoethanol ylmethyl tin
In the round-bottomed flask of 250ml, be added it is dry after 55.2 grams of mercaptoethanol ylmethyl tin, 2.1 grams of solid sodium hydroxide,
Suitable quantity of water is added in heating stirring 3 hours under the conditions of 110-115 DEG C, continues stirring 30 minutes, is neutralized to neutrality with diluted acid, protects
Leaving layer organic layer washed once with 80-90 DEG C of hot water, is placed under the conditions of 115 DEG C of oil baths, -0.98MPa and rotates drying, obtains
To yellowish viscous solid.
Step 3, the preparation of dicarboxylic acids mercaptoethanol ester
In the round-bottomed flask with reflux unit and the 250ml of water segregator, 214.78 grams of adipic acid are added, mercaptoethanol 234.45
Gram, it 1.41 grams of p-methyl benzenesulfonic acid, 1.15 grams of stannous chloride, is placed in 105-107 DEG C of oil bath, heated instead under the conditions of -0.98MPa
It answers 8.5 hours, it is cooling, suitable quantity of water is added, washed once, retains organic layer, is placed in 108 DEG C of oil baths, -0.98MPa condition backspin
It is evaporated dry, obtains 389.7 grams of colourless transparent liquid.
Step 4, it compounds
0.504 gram of 0.507 gram of product obtained with step 3 of product of step 2 is taken to be mixed, in obtained composition, etherificate
The mass percent of product is 49.8%.
Step 5, the PVC heat stabilizer composition that step 4 obtains is separately added in PVC, PVC heat stabilizer composition
The mass percent of contained tin element is 18.51%.
Embodiment 2
The present embodiment is substantially the same manner as Example 1, the difference is that the product of step 2 and the product of step 3 is taken to be mixed, obtains
Composition in, be etherified product mass percent be 10%.
The PVC heat stabilizer composition of the embodiment is separately added in PVC, the stanniferous member of PVC heat stabilizer composition institute
The mass percent of element is 2%.
The PVC heat stabilizer composition is separately added in PVC, tin element contained by PVC heat stabilizer composition and sulphur member
The molar ratio of element is 1:2.
When the PVC heat stabilizer composition is separately added in PVC, it is mixed that the dosage of PVC heat stabilizer composition accounts for PVC
Close the 1.3% of quality of material.
Embodiment 3
The present embodiment is substantially the same manner as Example 1, the difference is that the product of step 2 and the product of step 3 is taken to be mixed, obtains
Composition in, be etherified product mass percent be 30%.
The PVC heat stabilizer composition of the embodiment is separately added in PVC, the stanniferous member of PVC heat stabilizer composition institute
The mass percent of element is 5%.
The PVC heat stabilizer composition is separately added in PVC, tin element contained by PVC heat stabilizer composition and sulphur member
The molar ratio of element is 1:4.
When the PVC heat stabilizer composition is separately added in PVC, it is mixed that the dosage of PVC heat stabilizer composition accounts for PVC
Close the 1% of quality of material.
Embodiment 4
The present embodiment is substantially the same manner as Example 1, the difference is that the difference is that the product of step 2 and the product of step 3 is taken to carry out
It mixes, in obtained composition, the mass percent for being etherified product is 50%.
The PVC heat stabilizer composition of the embodiment is separately added in PVC, the stanniferous member of PVC heat stabilizer composition institute
The mass percent of element is 31%.
The PVC heat stabilizer composition is separately added in PVC, tin element contained by PVC heat stabilizer composition and sulphur member
The molar ratio of element is 1:15.
When the PVC heat stabilizer composition is separately added in PVC, it is mixed that the dosage of PVC heat stabilizer composition accounts for PVC
Close the 0.7% of quality of material.
Embodiment 5
The present embodiment is substantially the same manner as Example 1, the difference is that the product of step 2 and the product of step 3 is taken to be mixed, obtains
Composition in, be etherified product mass percent be 80%
The PVC heat stabilizer composition of the embodiment is separately added in PVC, tin element contained by PVC heat stabilizer composition
Mass percent be 39%.
When the PVC heat stabilizer composition is separately added in PVC, tin element contained by PVC heat stabilizer composition with
The molar ratio of element sulphur is 1:25.
When the PVC heat stabilizer composition is separately added in PVC, it is mixed that the dosage of PVC heat stabilizer composition accounts for PVC
Close the 0.01% of quality of material.
Embodiment 6
The present embodiment is substantially the same manner as Example 1, unlike, the product for taking the product of step 2 and step 3 to obtain is mixed
It closes, in obtained composition, the mass percent for being etherified product is 51.8%.
The PVC heat stabilizer composition and epoxidized soybean oil of the embodiment are added in PVC together.
The auxiliary heat stabilizer is used in this present embodiment, and content is controlled 1%.
Embodiment 7
The present embodiment is substantially the same manner as Example 1, unlike, the product for taking the product of step 2 and step 3 to obtain is mixed
It closes, in obtained composition, the mass percent for being etherified product is 53%.
The PVC heat stabilizer composition and phosphite ester of the embodiment are added in PVC together.
The auxiliary heat stabilizer is used in this present embodiment, content 15%.
Embodiment 8
The present embodiment is substantially the same manner as Example 1, unlike, the product for taking the product of step 2 and step 3 to obtain is mixed
It closes, in obtained composition, the mass percent for being etherified product is 45%.
The PVC heat stabilizer composition and polyalcohol of the embodiment are added in PVC together, polyol amount is
3%。
Embodiment 9
The present embodiment is substantially the same manner as Example 1, unlike, the product for taking the product of step 2 and step 3 to obtain is mixed
It closes, in obtained composition, the mass percent for being etherified product is 55%.
The PVC heat stabilizer composition and hypophosphites of the embodiment are added in PVC together.
The hypophosphites is used in this present embodiment, content 8%.
Embodiment 10
The present embodiment is substantially the same manner as Example 9, be not both auxiliary heat stabilizer be sterically hindered amines, content 15%.
Embodiment 11
The present embodiment is substantially the same manner as Example 9, be not both auxiliary heat stabilizer be glycidyl compound, content 10%.
Embodiment 12
The present embodiment is substantially the same manner as Example 9, be not both auxiliary heat stabilizer be phenol antioxidant, content 8.5%.
Embodiment 13
The present embodiment is substantially the same manner as Example 9, be not both auxiliary heat stabilizer be epoxidized soybean oil, phosphite ester, polyalcohol,
Hypophosphites, sterically hindered amines, glycidyl compound, several compositions mixed in phenol antioxidant.
Control application test is particularly made in the effect of composition in order to better illustrate the present invention.According to listed by table 1
The test of act matches, and under the mixing of mixer, each component is uniformly mixed.It is kneaded 2 minutes on being kneaded Kun in 190 DEG C.It takes
The Kun refining glue piece of lower formation, film stock thickness are 0.5 millimeter, intercept several fritters of 20mmX20mm, are placed sequentially in thermally conductive platelet
On, it is put into the case where heating in 190 DEG C of constant temperature ovens having been warmed up, sample according to certain time interval, observe its discoloration,
Color change situation is divided into 8 grades from 0-5 according to the depth degree of discoloration.0 indicates to be basically unchanged color, and 5 indicate discoloration
Most serious.Observation result is listed in table 3.
The basic components of 1 polyvinyl chloride resin mixture of table match
2 stabilizer of table composition and index explanation
The film discoloration of the static Thermal test of table 3
Note: 0- is basically unchanged color, the micro- Huang of 1- trimming, the micro- Huang of 2-, 3- jaundice, 4- partially it is black perhaps have stain 5- integrally black or
Pitch-black (most serious).
From table 3 it is observed that using composition described in the present invention as heat stabilizer, can not only reach really
To the effect of stable base film, and in terms of the initial stage color for keeping film, obvious action is shown.This is obviously
Target of the invention is met, reaches the purpose of the present invention with being well suited for.Above embodiment is intended merely to that this is better described
Invention, is not construed as limited.Without excessive test, person skilled in the field can make various replacements and change
Change, and substantially the same method can be implemented with means of equal value and obtain substantially the same as a result, these are all without departing from this
The true spirit and range of invention.
Claims (10)
1. a kind of PVC heat stabilizer composition, it is characterised in that: including dicarboxylic acids mercaptoethanol ester and by mercaptoethanol Ji Jia
The mass percent of the etherificate product that Ji Xi is etherified, the etherificate product is 10%-80%.
2. a kind of PVC heat stabilizer composition according to claim 1, it is characterised in that: under the etherificate product is
The mixture of one or more of the compound of four kinds of structural formulas of column:
Structure formula (I):
Structure formula (II):
Structure formula (III)
Structure formula (IV)
。
3. a kind of PVC heat stabilizer composition according to claim 1, it is characterised in that: the mercaptoethanol ylmethyl
Tin is the mixture of tri-thiol ethyl alcohol ylmethyl tin, 3-mercaptoethanol base stannous methide or both.
4. a kind of PVC heat stabilizer composition according to claim 1, it is characterised in that: the dicarboxylic acids sulfydryl second
Alcohol ester is by dicarboxylic acids and the mercaptoethanol esterification products that condensation reaction obtains in the presence of a catalyst.
5. a kind of PVC heat stabilizer composition according to claim 4, it is characterised in that: the dicarboxylic acids is that carbon is former
The straight-chain dicarboxylic acid or corresponding acid anhydrides that subnumber is 4-18.
6. a kind of PVC heat stabilizer composition according to claim 5, it is characterised in that: the dicarboxylic acids is fourth two
The mixture of one or more of acid, adipic acid, glutaric acid, laurel bisgallic acid.
7. a kind of PVC heat stabilizer composition according to claim 4, it is characterised in that: the catalyst is hydrogen sulfate
The mixture that sodium, p-methyl benzenesulfonic acid, stannous chloride one or more of are worked as.
8. a kind of preparation method of PVC heat stabilizer composition, it is characterised in that: this method includes etherate preparation step, two
First carboxylic acid mercaptoethanol ester preparation step and compounding step,
The etherate preparation step specifically:
Step 1, mercaptoethanol ylmethyl tin is prepared
Methyl chloride tin aqueous solution is reacted with mercaptoethanol, in reaction, alkaline reaction is added and falls the acid in system, then passes through
Separation obtains mercaptoethanol ylmethyl tin after being dried；
Step 2, etherification reaction
Mercaptoethanol ylmethyl tin is reacted under the action of highly basic, obtains yellowish viscous solid；
The dicarboxylic acids mercaptoethanol ester preparation step specifically:
Dicarboxylic acids and mercaptoethanol are subjected to lower condensation reaction under the effect of the catalyst, obtain colourless transparent liquid；
The compounding step, which refers to, mixes etherificate product with dicarboxylic acids mercaptoethanol ester, the combination obtained after mixing
In object, the mass percent for being etherified product is 10%-80%.
9. a kind of PVC heat stabilizer composition is used in the application method in PVC, it is characterised in that: the PVC heat stabilizer combination
Object is separately added to be added in PVC together after mixing in PVC or with auxiliary heat stabilizer.
10. a kind of PVC heat stabilizer composition according to claim 9 is used in the application method in PVC, feature exists
In: when the PVC heat stabilizer composition is separately added in PVC, the quality hundred of tin element contained by PVC heat stabilizer composition
Divide than control between 2%-39%；The molar ratio of tin element contained by PVC heat stabilizer composition and element sulphur is controlled in 1:2-1:
Between 25；The dosage of PVC heat stabilizer composition accounts for the 0.01%-1.3% of PVC mixture material quality.
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| WO2021173697A1 (en) * | 2020-02-24 | 2021-09-02 | Pmc Organometallix, Inc. | Alkyl-bridged tin-based thermal stabilizers for halogenated resins and synthesis and uses therof |
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| WO2021173697A1 (en) * | 2020-02-24 | 2021-09-02 | Pmc Organometallix, Inc. | Alkyl-bridged tin-based thermal stabilizers for halogenated resins and synthesis and uses therof |
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| GB2608041B (en) * | 2020-02-24 | 2024-05-15 | Pmc Organometallix Inc | Alkyl-bridged tin-based thermal stabilizers for halogenated resins and synthesis and uses therof |
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