CN103030749B - SEBS grafting N-substituted maleimide and preparation method thereof - Google Patents
SEBS grafting N-substituted maleimide and preparation method thereof Download PDFInfo
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- CN103030749B CN103030749B CN201210580305.5A CN201210580305A CN103030749B CN 103030749 B CN103030749 B CN 103030749B CN 201210580305 A CN201210580305 A CN 201210580305A CN 103030749 B CN103030749 B CN 103030749B
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Abstract
The invention relates to graft polymer and a preparation method thereof, in particular to SEBS (styrene-ethylene-butene-styrene) grafting N-substituted maleimide and a preparation method thereof. SEBS grafting N-substituted maleimide and the preparation method mainly solve the technical problem that the compatibility among SEBS, a polar polymer and an inorganic flame retardant is poor. SEBS grafting N-substituted maleimide comprises the following components: SEBS resin, N-substituted maleimide, an initiating agent and an antioxidant agent. The method comprises the following steps that 1, N-substituted maleimide, the initiating agent and the antioxidant agent are dissolved with acetone, and then sprayed into the SEBS resin; and a raw mixture material is obtained; and 2, the raw mixture material obtained in Step 1 is poured into a hopper of a twin-screw extruder, and subjected to melt extrusion grafting and pelleting, and SEBS grafting N-substituted maleimide is obtained. SEBS grafting N-substituted maleimide and the method are applied to the fields of engineering plastics, wires and cables.
Description
Technical field
The present invention relates to a kind of graftomer and preparation method thereof.
Background technology
N-substituted maleimide amine is the important organic compound of a class, on the molecular chain of this compounds, has α, beta-unsaturated acyl imines ring texture, and the rotation of restriction molecule chain effectively, makes polymkeric substance resistance toheat high.N-phenylmaleimide (N-Phenylmaleimide, N-PMI), be commonly called as " single horse ", a kind of yellow needle-like crystal, 90 DEG C～91 DEG C of fusing points, 162 DEG C of boiling points, it is the heat-resisting organic monomer of one that developed recently gets up, because it has five-membered cyclic two dimensional structure, embed the inward turning resistance that can increase chain in macromolecular chain, thereby improve the thermotolerance of material.At present, N-PMI main application is as ABS heat-proof modifier, can effectively improve thermotolerance, processing characteristics, consistency and the impact resistance of ABS resin.In addition, N-PMI also can be used as linking agent and the heat-proof modifier of the thermoplasticss such as PS, PMMA, PP, PVC.N-N-cyclohexylmaleimide (N-Cyclohexylmaleimide) is white plates crystal, and purity is greater than 99%, 89.5 DEG C～90.3 DEG C of fusing points, and 132 DEG C of boiling points, can be used as the thermo-stabilizer of the resins such as PVC.N-phenylmaleimide, N-N-cyclohexylmaleimide are the small molecule monomer with polar functional group, contain unsaturated double-bond simultaneously, are grafted to the polarity that can improve SEBS on SEBS molecular chain.Phenyl in N-phenylmaleimide, N-N-cyclohexylmaleimide structure and cyclohexyl can be used as the rigid radical rotation of restriction molecule chain effectively, make SEBS resistance toheat high.Other contain the substituent N-substituted maleimide of opposed polarity amine (such as containing the N-substituted maleimide amine of carboxyl, hydroxyl, epoxy group(ing), ester group etc. in substituent structure) grafting, also can give SEBS polarity, the consistency of SEBS and polar polymer and inorganic combustion inhibitor is improved.
SEBS is the new modified elastomerics being made through selecting hydrogenation by rubber segments polyhutadiene unsaturated double-bond in polystyrene-poly butylene-polystyrene (SBS) molecule.SEBS not only has excellent ageing-resistant performance, and there is good mechanical property, elongation at break is 0～150%, exceed vulcanized rubber, not only ozone, ultraviolet ray, electric arc are had to good tolerance, also there is good oil resistant, chemicals-resistant, corrodibility and excellent resistance to low temperature.Its product has water white transparency, nontoxic, tasteless, tinctorial property is excellent, density is low and have the features such as stronger bonding force with other material, is therefore widely used in the fields such as tackiness agent, coating, plastic modifier, trolley part, electric wire, food, medical treatment.But, owing to not containing polarity or reactive group on SEBS molecular chain, with urethane, polymeric amide, polyester etc. and polar polymer and inorganic combustion inhibitor, as poor in the consistency of aluminium hydroxide, magnesium hydroxide etc.; At present, for the graft modification of SEBS, the monomer who selects is mainly taking maleic anhydride, acrylic monomer as main, and for the SEBS of modified by maleic acid anhydride graft, the maleic anhydride in grafting is easily hydrolyzed, thereby has influence on mechanics and the electric property of polymkeric substance.
Summary of the invention
The present invention will solve the technical problem that SEBS and polar polymer and inorganic combustion inhibitor consistency are poor, thereby a kind of SEBS graft N-substituted maleimide amine and preparation method thereof is provided.
A kind of SEBS graft N-substituted maleimide amine of the present invention by weight percentage composition is made up of 65%～97% SEBS resin, 0.1%～32% N-substituted maleimide amine, 0.1%～4% initiator and the oxidation inhibitor of surplus; Wherein, N-substituted maleimide amine is N-phenylmaleimide or N-N-cyclohexylmaleimide; Initiator is a kind of or two kinds of mixing in any proportion in BPO (benzoyl peroxide), DCP (dicumyl peroxide) and BIPB (two-(tert-butyl peroxy sec.-propyl) benzene); Oxidation inhibitor is 1010 (four [β-(3,5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), 168 (three [2,4-di-tert-butyl-phenyl] phosphorous acid ester) and 1024 (N, N '-bis-[3-(3,5-di-tert-butyl-hydroxy phenyl) propionyl] hydrazine) in a kind of or two kinds mix in any proportion.
The preparation method of a kind of SEBS graft N-substituted maleimide amine of the present invention carries out according to the following steps:
One, percentage composition takes 65%～97% SEBS resin, 0.1%～32% N-substituted maleimide amine, 0.1%～4% initiator and the oxidation inhibitor of surplus by weight, by N-substituted maleimide amine, initiator and oxidation inhibitor acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 100～300r/min mixed solution, spray on SEBS resin particle, then continue to stir, until acetone all volatilizees, obtain mixture material; Wherein, SEBS resin particle is bought from Ke Teng Polymer Company of the U.S., and trade names are 1652; Also other trades mark that can select other companies to produce;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 140～180 DEG C, two district's temperature are 150～200 DEG C, three district's temperature are 150～200 DEG C, four district's temperature are 150～200 DEG C, and head temperature is 150～200 DEG C, and screw speed is 100～170r/min, the residence time is 2～12min, and pressure is 15～20MPa.
The present invention includes following beneficial effect:
1, the present invention uses N-substituted maleimide amine Maleated SEBS resin, can make SEBS polarity improve, and then improves the consistency of SEBS resin and polar polymer or inorganic combustion inhibitor, strengthens mechanical property, the resistance toheat of polymkeric substance;
2, the advantages of nontoxic raw materials that the present invention uses is harmless, the not auxiliary agent of halogen-containing class, and SEBS graft N-substituted maleimide amine of preparation contacts with human body and can not produce any untoward reaction simultaneously;
3, the N electronegativity in grafted monomer N-substituted maleimide molecular structure of the present invention is little, be greater than electrophilic induction to electron conjugated effect, so the lone-pair electron on N can well with carbonyl conjugation, cause the activity decreased of carbonyl, be difficult for nucleophilic addition(Adn), so not facile hydrolysis of SEBS prepared by the present invention graft N-substituted maleimide amine, thereby electric property and the mechanical property of raising graftomer.
Embodiment
Embodiment one: a kind of SEBS graft N-substituted maleimide amine of present embodiment by weight percentage composition is made up of 65%～97% SEBS resin, 0.1%～32% N-substituted maleimide amine, 0.1%～4% initiator and the oxidation inhibitor of surplus; Wherein, N-substituted maleimide amine is N-phenylmaleimide or N-N-cyclohexylmaleimide; Initiator is a kind of or two kinds of mixing in any proportion in BPO (benzoyl peroxide), DCP (dicumyl peroxide) and BIPB (two-(tert-butyl peroxy sec.-propyl) benzene); Oxidation inhibitor is 1010 (four [β-(3,5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), 168 (three [2,4-di-tert-butyl-phenyl] phosphorous acid ester) and 1024 (N, N '-bis-[3-(3,5-di-tert-butyl-hydroxy phenyl) propionyl] hydrazine) in a kind of or two kinds mix in any proportion.
Embodiment two: the preparation method of a kind of SEBS graft N-substituted maleimide amine of present embodiment carries out according to the following steps:
One, percentage composition takes 65%～97% SEBS resin, 0.1%～32% N-substituted maleimide amine, 0.1%～4% initiator and the oxidation inhibitor of surplus by weight, by N-substituted maleimide amine, initiator and oxidation inhibitor acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 100～300r/min mixed solution, spray on SEBS resin, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 140～180 DEG C, two district's temperature are 150～200 DEG C, three district's temperature are 150～200 DEG C, four district's temperature are 150～200 DEG C, and head temperature is 150～200 DEG C, and screw speed is 100～170r/min, the residence time is 2～12min, and pressure is 15～20MPa.
Present embodiment invention comprises following beneficial effect:
1, present embodiment is used N-substituted maleimide amine Maleated SEBS resin, can make SEBS polarity improve, and then improve the consistency of SEBS resin and polar polymer or inorganic combustion inhibitor, strengthens mechanical property, the resistance toheat of polymkeric substance;
2, the advantages of nontoxic raw materials that present embodiment is used is harmless, the not auxiliary agent of halogen-containing class, and the N-substituted maleimide amine Maleated SEBS of preparation contacts with human body and can not produce any untoward reaction simultaneously;
3, the N electronegativity in the grafted monomer N-substituted maleimide amine molecule structure of present embodiment is little, be greater than electrophilic induction to electron conjugated effect, so the lone-pair electron on N can well with carbonyl conjugation, cause the activity decreased of carbonyl, be difficult for nucleophilic addition(Adn), so not facile hydrolysis of SEBS prepared by present embodiment graft N-substituted maleimide amine, thereby electric property and the mechanical property of raising graftomer.
Embodiment three: present embodiment is different from embodiment two: in step 1, N-substituted maleimide amine is N-phenylmaleimide or N-N-cyclohexylmaleimide.Other is identical with embodiment two.
Embodiment four: present embodiment is different from embodiment two or three: in step 1, initiator is a kind of or two kinds of mixing in any proportion in BPO (benzoyl peroxide), DCP (dicumyl peroxide) and BIPB (two-(tert-butyl peroxy sec.-propyl) benzene).Other is identical with embodiment two or three.
Embodiment five: present embodiment is different from one of embodiment two to four: in step 1, oxidation inhibitor is 1010 (four [β-(3,5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), 168 (three [2,4-di-tert-butyl-phenyl] phosphorous acid ester) and 1024 (N, N '-bis-[3-(3,5-di-tert-butyl-hydroxy phenyl) propionyl] hydrazine) in a kind of or two kinds mix in any proportion.Other is identical with one of embodiment two to four.
Embodiment six: present embodiment is different from one of embodiment two to five: in step 2, the residence time is 6～10min.Other is identical with one of embodiment two to five.
By following verification experimental verification beneficial effect of the present invention:
Test one: the preparation method of a kind of SEBS graft N-substituted maleimide amine of this test realizes according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 140 DEG C, and two district's temperature are 150 DEG C, three district's temperature are 150 DEG C, and four district's temperature are 150 DEG C, and head temperature is 150 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
Tested and tested percentage of grafting by acid base titration, the percentage of grafting that obtains this test is 1.2501%.
Test two: the preparation method of a kind of SEBS graft N-substituted maleimide amine of this test realizes according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 150 DEG C, and two district's temperature are 160 DEG C, three district's temperature are 160 DEG C, and four district's temperature are 160 DEG C, and head temperature is 160 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
Tested and tested percentage of grafting by acid base titration, the percentage of grafting that obtains this test is 1.5211%.
Test three: the preparation method of a kind of SEBS graft N-substituted maleimide amine of this test realizes according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 160 DEG C, and two district's temperature are 170 DEG C, three district's temperature are 170 DEG C, and four district's temperature are 170 DEG C, and head temperature is 170 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
Tested and tested percentage of grafting by acid base titration, the percentage of grafting that obtains this test is 1.5715%.
Test four: the preparation method of a kind of SEBS graft N-substituted maleimide amine of this test realizes according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin particle, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 170 DEG C, and two district's temperature are 180 DEG C, three district's temperature are 180 DEG C, and four district's temperature are 1580 DEG C, and head temperature is 180 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
Tested and tested percentage of grafting by acid base titration, the percentage of grafting that obtains this test is 2.0229%.
Test five: the preparation method of a kind of SEBS graft N-substituted maleimide amine of this test realizes according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 180 DEG C, and two district's temperature are 190 DEG C, three district's temperature are 190 DEG C, and four district's temperature are 190 DEG C, and head temperature is 190 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
Tested and tested percentage of grafting by acid base titration, the percentage of grafting that obtains this test is 1.7093%.
Can draw from testing one to five percentage of grafting, constant in proportioning, the reaction times is all under the condition of 10min, along with the rising of temperature of reaction, the grafting of SEBS graft N-maleimide reduces after taking the lead in raising, and occurs the maximum of percentage of grafting in the time of 180 DEG C, is 2.0229%.In five tests, the percentage of grafting under 140 DEG C of reaction conditionss is minimum, is 1.2501%; These results suggest that, the percentage of grafting of the present invention in the time of 180 DEG C of left and right of fusing point of SEBS is best, the now abundant melting of SEBS resin, and molecular chain fully stretches, the probability that touches grafted monomer free radical increases substantially, thereby is conducive to N-phenylmaleimide free radical attack SEBS molecular chain.Meanwhile, in the time that temperature is lower, SEBS does not reach melted state, and monomer, initiator, free radical etc. are embedded among macromolecular chain, thereby have reduced graft effect.And after temperature is higher than 180 DEG C, cause over oxidation, make free radical inactivation or termination, and then reduced percentage of grafting.In sum, the better temperature of reaction of the present invention under fixation response time 10min condition is 180 DEG C.
Claims (4)
1. a preparation method for SEBS graft N-substituted maleimide amine, is characterized in that the preparation method of SEBS graft N-substituted maleimide amine carries out according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 150 DEG C, and two district's temperature are 160 DEG C, three district's temperature are 160 DEG C, and four district's temperature are 160 DEG C, and head temperature is 160 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
2. a preparation method for SEBS graft N-substituted maleimide amine, is characterized in that the preparation method of SEBS graft N-substituted maleimide amine carries out according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 160 DEG C, and two district's temperature are 170 DEG C, three district's temperature are 170 DEG C, and four district's temperature are 170 DEG C, and head temperature is 170 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
3. a preparation method for SEBS graft N-substituted maleimide amine, is characterized in that the preparation method of SEBS graft N-substituted maleimide amine carries out according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin particle, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 170 DEG C, and two district's temperature are 180 DEG C, three district's temperature are 180 DEG C, and four district's temperature are 180 DEG C, and head temperature is 180 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
4. a preparation method for SEBS graft N-substituted maleimide amine, is characterized in that the preparation method of SEBS graft N-substituted maleimide amine carries out according to the following steps:
One, percentage composition takes 93% SEBS resin, 3% N-substituted maleimide amine, 1% initiator DCP and 1% antioxidant 1010 by weight, by N-substituted maleimide amine, initiator DCP and antioxidant 1010 acetone solution, obtain mixed solution, use high-speed mixer under the rotating speed of 200r/min mixed solution, spray on SEBS resin, then continue to stir, until acetone all volatilizees, obtain mixture material;
Two, mixture material step 1 being obtained is poured in the hopper of twin screw extruder, and through grafting with melt extrusion, granulation, obtains SEBS graft N-substituted maleimide amine; Wherein, each heating region temperature of twin screw extruder is respectively: district's temperature is 180 DEG C, and two district's temperature are 190 DEG C, three district's temperature are 190 DEG C, and four district's temperature are 190 DEG C, and head temperature is 190 DEG C, screw speed is 170r/min, and the residence time is 10min, and pressure is 15MPa.
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| CN102311606A (en) * | 2010-09-29 | 2012-01-11 | 深圳市科聚新材料有限公司 | Low-odour SEBS (styrene butadiene styrene block copolymer) melt-grafting maleic anhydride and preparation method thereof |
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| CN102311606A (en) * | 2010-09-29 | 2012-01-11 | 深圳市科聚新材料有限公司 | Low-odour SEBS (styrene butadiene styrene block copolymer) melt-grafting maleic anhydride and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| "N-PMI-St-PB本体聚合过程中的相转变(I)* 相转变过程中体系物理特征的变化";陈媛等;《化工学报》;20000625;第51卷(第3期);第362-366页 * |
| 陈媛等."N-PMI-St-PB本体聚合过程中的相转变(I)* 相转变过程中体系物理特征的变化".《化工学报》.2000,第51卷(第3期),第362-366页. * |
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