CN105924619B - One kind is based on the preparation method of poly- (styrene-co- acrylonitrile) compatilizer - Google Patents
One kind is based on the preparation method of poly- (styrene-co- acrylonitrile) compatilizer Download PDFInfo
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- CN105924619B CN105924619B CN201610321254.2A CN201610321254A CN105924619B CN 105924619 B CN105924619 B CN 105924619B CN 201610321254 A CN201610321254 A CN 201610321254A CN 105924619 B CN105924619 B CN 105924619B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/6262—Polymers of nitriles derived from alpha-beta ethylenically unsaturated carboxylic acids
Abstract
The present invention relates to a kind of preparation method for being based on poly- (styrene co acrylonitrile) compatilizer, including step：The preparation of the preparation of hydroxy terminated polypropylene acid esters, hydroxyl poly- (styrene co acrylonitrile) and the preparation of poly- (styrene co acrylonitrile) g polyacrylate compatilizers；The beneficial effects of the invention are as follows：Compatilizer grafted chain chain length is controllable, and compatilizer effect is good.
Description
Technical field
The invention belongs to polymeric material fields, are related to a kind of preparation for being based on poly- (styrene-co- acrylonitrile) compatilizer
Method.
Background technology
Styrene-acrylonitrile copolymer (SAN) is also known as AS resins, is the thermoplastic resin of water white transparency, has high temperature resistant
Property, outstanding glossiness and resistant to chemical media, also excellent hardness, rigidity, dimensional stability and higher bearing capacity.
Styrene composition makes SAN hard, transparent and easy to process；Acrylonitrile composition makes SAN have chemical stability and thermal stability.But
It is that AS resin shock resistances are poor, brittleness limits its extensive use.
Acrylic rubber (ACM) is the copolymer using acrylate mainly to form, since backbone structure is fully saturated,
It is that a kind of heat-resisting, oil resistant, cold tolerance be excellent and the specific rubber of moderate cost, the rubber system being widely used in auto industry
Product.ACM rubber good toughness can improve the shortcomings that AS resin toughness is poor with the mixing of AS resins.
Resin toughening method includes copolymerization toughening and blending toughening etc., and rubber, that is, elastomer carrys out toughening tree with resin alloy
Fat is a kind of method easily and economically.Two alternate binding forces are improved in order to further improve the compatibility between blend components,
It needs to use compatilizer.Such as patent CN 101591416B describe a kind of method for preparing graft type compatilizer, using Malaysia
Acid anhydrides carries out fusion-grafting on the twin screw extruder, but this method has the defects of grafting efficiency is low, and grafted branches are short.
Invention content
The technical problem to be solved by the present invention is to：Based on the above problem, the present invention provides a kind of based on poly- (styrene-co-
Acrylonitrile) compatilizer preparation method.
A technical solution is used by the present invention solves its technical problem：One kind is based on poly- (styrene-co- propylene
Nitrile) compatilizer preparation method, include the following steps：
(1) preparation of hydroxy terminated polypropylene acid esters：Initiator I, monomer I, complex liquid, reducing agent and solvent I are added to
In reaction vessel, by reaction system vacuum nitrogen gas, 50~100 DEG C are reacted 2~10 hours, and hydroxy terminated polypropylene acid is made
Ester, molecular weight distribution<2.0；
(2) preparation of hydroxyl poly- (styrene-co- acrylonitrile)：Initiator II, monomer II, styrene, acrylonitrile are delayed
Slowly it is added drop-wise in the reaction vessel equipped with solvent II, 80~110 DEG C are reacted 3~10 hours, and poly- (styrene-co- propylene is made
Nitrile)；
(3) preparation of poly- (styrene-co- acrylonitrile)-g- polyacrylate compatilizers：By step (1) end hydroxyl obtained
With diisocyanate under catalyst action, 40~80 DEG C are reacted 0.5~8 hour based polyacrylic acid ester, add step (2) system
Poly- (styrene-co- acrylonitrile) obtained, 80~100 DEG C are reacted 1~10 hour, obtain the poly- (styrene-co- propylene of compatilizer
Nitrile)-g- polyacrylate.
Further, initiator I is the halogenated organic compound that an end group is hydroxyl, specially α-bromine in step (1)
For isobutyric acid hydroxyl ethyl ester, alpha-chloro isobutyric acid hydroxyl ethyl ester, alpha-brominated isobutyric acid hydroxy butyl ester, alpha-chloro isobutyric acid hydroxy butyl ester or 2-
One kind in bromo- N- (2- ethoxys) -2- methyl propanamides；Monomer I is esters of acrylic acid, specially methyl acrylate, propylene
One or more of acetoacetic ester, butyl acrylate or acrylic acid-2-ethyl caproite；Complex liquid is the transition metal halogen of oxidation state
Compound, ligand and ethyl alcohol are stirred evenly and are obtained at normal temperatures, and the transition metal halide of oxidation state is CuCl2、CuBr2、FeCl3
Or FeBr3One or more of, ligand is pentamethyldivinyltriamine, three-(N, N- dimethylaminoethyl) amine or 1,1,
One or more of 4,7,10,10- hexamethyl triens；Reducing agent is stannous octoate, ascorbic acid or glucose
One or more of.
Further, monomer I in step (1)：The molar ratio of initiator is 10：1~100：1, the transition metal of oxidation state
Halide：The molar ratio of monomer I is 0.00005：1~0.0005：1, the transition metal halide of oxidation state：Reducing agent I rubs
You are than being 1：10~1：25, the transition metal halide of oxidation state：The molar ratio of ligand is 1：10~1：30, I dosage of solvent is
The 10~100% of I mass of monomer.
Further, initiator II is radical initiator, specially azodiisobutyronitrile or peroxidating two in step (2)
One or both of benzoyl；Monomer II is (methyl) hydroxy-ethyl acrylate or (methyl) hydroxypropyl acrylate class.
Further, styrene in step (2)：Acrylonitrile mass ratio is 7：3, the quality of monomer II is monomer II and benzene second
The 5~25% of alkene, acrylonitrile gross mass, the quality of initiator II is monomer II and styrene, acrylonitrile gross mass 1~5 ‰.
Further, diisocyanate is specially methyl diphenylene diisocyanate, toluene diisocynate in step (3)
Ester, isophorone diisocyanate, two isocyanide of naphthalene -1,5- diisocyanate, 2,6- diisocyanate methyl caproate or hexamethyl
One kind in acid esters, catalyst are one or more of dibutyl tin laurate, triethanolamine or stannous octoate.
Further, the NCO/OH of diisocyanate and hydroxy terminated polypropylene acid esters is 2.0/1~3.0/1 in step (3),
The mass ratio of hydroxy terminated polypropylene acid esters and poly- (styrene-co- acrylonitrile) is 1：0.5~1：10.
The beneficial effects of the invention are as follows：Compatilizer grafted chain chain length is controllable, and compatilizer effect is good.
Specific embodiment
Presently in connection with specific embodiment, the invention will be further described, following embodiment be intended to illustrate invention rather than
Limitation of the invention further.
Embodiment 1
(1) preparation (design molecular weight 2000) of hydroxy terminated polypropylene acid methyl esters
Methyl acrylate 20.00g (0.2323mol), initiator are added in the four-hole boiling flask equipped with thermometer, agitating paddle
Alpha-brominated isobutyric acid hydroxy butyl ester 2.3911g (10.000mmol), CuBr20.02082g (0.09293mmol) and pentamethyl diethyl
Alkenyl triamine PMDETA 0.3221g (1.8585mmol), reducing agent stannous octoate Sn (EH)2 0.7529g(1.8585mmol)
And solvent toluene 10.00g, after mixing, lead to nitrogen bubbling, react 260min under 70 DEG C of oil baths, conversion ratio is up to 80%
Stop reaction afterwards, after product crosses neutral alumina column, precipitation is dried for standby.
(2) preparation of hydroxyl poly- (styrene-co- acrylonitrile)
Styrene 70g (0.6721mol), acrylonitrile 30g are slowly added dropwise in the reaction bulb equipped with toluene
The mixed monomer solution of (0.5660mol), hydroxy-ethyl acrylate 25g (0.2153mol) and dibenzoyl peroxide 0.5g, 90 DEG C
Lower reaction terminates for 7 hours, cooling discharge, is dried after product methanol extraction.
(3) preparation of poly- (styrene-co- acrylonitrile)-g- polymethyl acrylate
Take hydroxy terminated polypropylene acid methyl esters 10g (0.0050mol), toluene 15g, isoflurane chalcone diisocyanate 1.3337g
After reacting 2 hours at 60 DEG C, it is poly- (styrene-co- acrylonitrile) to add in hydroxyl for (0.0060mol), dibutyl tin laurate
10g is warming up to 80 DEG C, and reaction stops after 4 hours, and product methanol extraction, drying to constant weight.
Embodiment 2
(1) preparation (design molecular weight 4000) of hydroxy terminated polypropylene acetoacetic ester
Ethyl acrylate 20.00g (0.1998mol), initiator are added in the four-hole boiling flask equipped with thermometer, agitating paddle
Alpha-brominated isobutyric acid hydroxy butyl ester 1.1956g (5.0000mmol), CuBr20.01790g (0.0799mmol) and PMDETA
0.2769g (1.5981mmol), reducing agent Sn (EH)20.6474g (1.5981mmol) and toluene 10g, leads to after mixing
Nitrogen bubbling reacts 275min under 75 DEG C of oil baths, and conversion ratio stops after reaching 87%, after product crosses neutral alumina column, uses
Methanol extraction, drying.
(2) preparation of hydroxyl poly- (styrene-co- acrylonitrile)
Styrene 70g (0.6721mol), acrylonitrile 30g are slowly added dropwise in the reaction bulb equipped with toluene
The mixed monomer solution of (0.5660mol), hydroxy-ethyl acrylate 20g (0.1722mol) and dibenzoyl peroxide 0.48g, 90
It reacts seven hours and terminates at DEG C, cooling discharge is dried after product methanol extraction.
(3) preparation of poly- (styrene-co- acrylonitrile)-g- polyethyl acrylates
Take hydroxy terminated polypropylene acetoacetic ester 10g (0.0100mol), toluene 15g, isoflurane chalcone diisocyanate 0.6669g
After reacting 2 hours at 60 DEG C, it is poly- (styrene-co- acrylonitrile) to add in hydroxyl for (0.0030mol), dibutyl tin laurate
10g is warming up to 80 DEG C, and reaction stops after 4 hours, and product methanol extraction, drying to constant weight.
Embodiment 3
(1) preparation (design molecular weight 6000) of hydroxy terminated polypropylene acid butyl ester
Butyl acrylate 20.00g (0.1560mol), initiator are added in the four-hole boiling flask equipped with thermometer, agitating paddle
Alpha-brominated isobutyric acid hydroxy butyl ester 0.7970g (3.300mmol), CuBr20.01398g (0.06242mmol) and PMDETA
0.2163g (1.2483mmol), reducing agent Sn (EH)20.5057g (1.2483mmol) and toluene 15g, leads to after mixing
Nitrogen bubbling reacts 215min under 80 DEG C of oil baths, and conversion ratio stops after reaching 85%, and product uses first after crossing neutral alumina column
Alcohol precipitation drying.
(2) preparation of hydroxyl poly- (styrene-co- acrylonitrile)
Styrene 70g (0.6721mol), acrylonitrile 30g are slowly added dropwise in the reaction bulb equipped with toluene
The mixed monomer solution of (0.5660mol), hydroxy-ethyl acrylate 15g (0.1292mol) and dibenzoyl peroxide 0.46g, 90
It reacts 7 hours and terminates at DEG C, cooling discharge is dried after product methanol extraction.
(3) preparation of poly- (styrene-co- acrylonitrile)-g- butyl polyacrylates
Take hydroxy terminated polypropylene acid butyl ester 10g (0.0020mol), toluene 15g, isoflurane chalcone diisocyanate 0.4816g
(0.0022mol), dibutyl tin laurate after reacting 3.5 hours at 60 DEG C, add in hydroxyl polymethyl methacrylate
20g is warming up to 80 DEG C, and reaction stops after 8 hours, and product methanol extraction, drying to constant weight.
Embodiment 4
(1) preparation (design molecular weight 9000) of hydroxy terminated polypropylene acid -2- ethylhexyls
Acrylic acid-2-ethyl caproite 20.00g is added in the four-hole boiling flask equipped with thermometer, agitating paddle
The alpha-brominated isobutyric acid hydroxy butyl ester 0.5314g (2.200mmol) of (0.1085mol), initiator, CuBr20.009724g
(0.04341mmol) and PMDETA 0.1505g (0.8682mmol), reducing agent Sn (EH)-2 0.3517g(0.8682mmol)
And toluene 15g, after mixing, lead to nitrogen bubbling, 300min is reacted under 75 DEG C of oil baths, conversion ratio is anti-up to stopping after 81%
Should, after product crosses neutral alumina column, precipitation is dried for standby.
(2) preparation of hydroxyl poly- (styrene-co- acrylonitrile)
Styrene 70g (0.6721mol), acrylonitrile 30g are slowly added dropwise in the reaction bulb equipped with toluene
The mixed monomer solution of (0.5660mol), hydroxy-ethyl acrylate 10g (0.0861mol) and dibenzoyl peroxide 0.46g, 90
It reacts 8 hours and terminates at DEG C, cooling discharge is dried after product methanol extraction.
(3) preparation of poly- (styrene-co- acrylonitrile)-g- polyacrylic acid -2- ethylhexyls
Take hydroxy terminated polypropylene acid -2- ethylhexyls 10g (0.00111mol), toluene 15g, isoflurane chalcone diisocyanate
0.3210g (0.0014mol), dibutyl tin laurate, after reacting 5.5 hours at 60 DEG C, add in hydroxyl it is poly- (styrene-
Co- acrylonitrile) 10g, 80 DEG C are warming up to, is stopped after reacting 9h, product methanol extraction, drying to constant weight.
Compatilizer measure of merit
Respectively using the graft polymers of the preparation of embodiment 1,2,3,4 as compatilizer, with SAN/ACM with 35/15 mass ratio
Example mixing blending prepares impact batten according to ASTM-D256 standards, tests the impact property of hybrid resin, shock-testing result
It is shown in Table 1.
Table 1
Using above-mentioned desirable embodiment according to the present invention as enlightenment, by above-mentioned description, relevant staff is complete
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property range is not limited to the content on specification, it is necessary to determine its technical scope according to right.
Claims (5)
1. one kind is based on the preparation method of poly- (styrene-co- acrylonitrile) compatilizer, it is characterized in that：Include the following steps：
(1) preparation of hydroxy terminated polypropylene acid esters：Initiator I, monomer I, complex liquid, reducing agent and solvent I are added to reaction
In container, by reaction system vacuum nitrogen gas, 50~100 DEG C are reacted 2~10 hours, and hydroxy terminated polypropylene acid esters is made, point
Son amount distribution<2.0；
(2) preparation of hydroxyl poly- (styrene-co- acrylonitrile)：Initiator II, monomer II, styrene, acrylonitrile are slowly dripped
It is added in the reaction vessel equipped with solvent II, 80~110 DEG C are reacted 3~10 hours, are made poly- (styrene-co- acrylonitrile)；
(3) preparation of poly- (styrene-co- acrylonitrile)-g- polyacrylate compatilizers：Terminal hydroxy group made from step (1) is gathered
With diisocyanate under catalyst action, 40~80 DEG C are reacted 0.5~8 hour acrylate, and it is obtained to add step (2)
Poly- (styrene-co- acrylonitrile), 80~100 DEG C are reacted 1~10 hour, obtain poly- (styrene-co- the acrylonitrile)-g- of compatilizer
Polyacrylate；
In the step (1) initiator I for an end group be hydroxyl halogenated organic compound, specially alpha-brominated isobutyric acid
Hydroxyl ethyl ester, alpha-chloro isobutyric acid hydroxyl ethyl ester, alpha-brominated isobutyric acid hydroxy butyl ester, alpha-chloro isobutyric acid hydroxy butyl ester or 2- bromo- N- (2- hydroxyls
Ethyl) one kind in -2- methyl propanamides；Monomer I is esters of acrylic acid, specially methyl acrylate, ethyl acrylate, propylene
One or more of acid butyl ester or acrylic acid-2-ethyl caproite；Complex liquid is the transition metal halide of oxidation state, ligand and
Ethyl alcohol is stirred evenly and is obtained at normal temperatures, and the transition metal halide of oxidation state is CuCl2、CuBr2、FeCl3Or FeBr3In
One or more, ligand is pentamethyldivinyltriamine, three-(N, N- dimethylaminoethyl) amine or 1, Isosorbide-5-Nitrae, 7,10,10- six
One or more of methyl trien；Reducing agent is one kind or several in stannous octoate, ascorbic acid or glucose
Kind；
Initiator II is radical initiator, specially azodiisobutyronitrile or dibenzoyl peroxide in the step (2)
One or both of；Monomer II is (methyl) hydroxy-ethyl acrylate or (methyl) hydroxypropyl acrylate class.
2. a kind of preparation method for being based on poly- (styrene-co- acrylonitrile) compatilizer according to claim 1, feature
It is：Monomer I in the step (1)：The molar ratio of initiator is 10：1~100：1, the transition metal halide of oxidation state：It is single
The molar ratio of body I is 0.00005：1~0.0005：1, the transition metal halide of oxidation state：The molar ratio of reducing agent I is 1：10
~1：25, the transition metal halide of oxidation state：The molar ratio of ligand is 1：10~1：30, I dosage of solvent is I mass of monomer
10~100%.
3. a kind of preparation method for being based on poly- (styrene-co- acrylonitrile) compatilizer according to claim 1, feature
It is：Styrene in the step (2)：Acrylonitrile mass ratio is 7：3, the quality of monomer II is monomer II and styrene, propylene
The 5~25% of nitrile gross mass, the quality of initiator II is monomer II and styrene, acrylonitrile gross mass 1~5 ‰.
4. a kind of preparation method for being based on poly- (styrene-co- acrylonitrile) compatilizer according to claim 1, feature
It is：Diisocyanate is specially methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), different Fo Er in the step (3)
One in ketone diisocyanate, naphthalene -1,5- diisocyanate, 2,6- diisocyanate methyl caproate or hexamethylene diisocyanate
Kind, catalyst is one or more of dibutyl tin laurate, triethanolamine or stannous octoate.
5. a kind of preparation method for being based on poly- (styrene-co- acrylonitrile) compatilizer according to claim 1, feature
It is：The NCO/OH of diisocyanate and hydroxy terminated polypropylene acid esters is 2.0/1~3.0/1 in the step (3), and terminal hydroxy group gathers
The mass ratio of acrylate and poly- (styrene-co- acrylonitrile) is 1：0.5~1：10.
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| CN101486825A (en) * | 2008-01-17 | 2009-07-22 | 深圳市亚塑科技有限公司 | Preparation of weather resistant PC and ASA copolymer alloy |
| CN105418935A (en) * | 2015-12-24 | 2016-03-23 | 上海锦湖日丽塑料有限公司 | Grafted polymer compatilizer, preparation method and application thereof |
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| CN101486825A (en) * | 2008-01-17 | 2009-07-22 | 深圳市亚塑科技有限公司 | Preparation of weather resistant PC and ASA copolymer alloy |
| CN105418935A (en) * | 2015-12-24 | 2016-03-23 | 上海锦湖日丽塑料有限公司 | Grafted polymer compatilizer, preparation method and application thereof |
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| Title |
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| ASA核壳接枝共聚物接枝效果的影响因素;马令庆等;《合成树脂及塑料》;20121231;第29卷(第5期);第13-17页 * |
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