CN107603157B - A kind of Janus expanding material and preparation method thereof for rubber-toughened epoxy resin - Google Patents
A kind of Janus expanding material and preparation method thereof for rubber-toughened epoxy resin Download PDFInfo
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- CN107603157B CN107603157B CN201710985945.7A CN201710985945A CN107603157B CN 107603157 B CN107603157 B CN 107603157B CN 201710985945 A CN201710985945 A CN 201710985945A CN 107603157 B CN107603157 B CN 107603157B
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Abstract
The Janus expanding material and preparation method thereof that the invention discloses a kind of for rubber-toughened epoxy resin, the preparation method is that: 1) it disperses polydivinylbenezene/silica Janus material and azo-bis-isobutyl cyanide in toluene, after logical 0.5 h of nitrogen, lauryl mercaptan is quickly instilled, centrifuge washing obtains lauryl mercaptan-polydivinylbenezene/silica Janus material after reacting a period of time；2) it disperses lauryl mercaptan-polydivinylbenezene/silica Janus material and γ-methacryloxypropyl trimethoxy silane in toluene, centrifuge washing obtains lauryl mercaptan-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silane Janus material, i.e., the described Janus expanding material after reaction a period of time.The Janus expanding material of the method for the present invention preparation has anisotropic chemical structure, possesses phase interface behavior abundant, strong to liquid isoprene rubber/epoxy resin composite material compatibilization.
Description
Technical field
The present invention relates to a kind of preparation methods of expanding material, and in particular to a kind of for rubber-toughened epoxy resin
Janus expanding material and preparation method thereof.
Background technique
Contain active epoxy group in epoxy molecule structure, can crosslink and react with a plurality of types of curing agent
And form the high polymer of insoluble tridimensional network.Epoxy resin cured product has excellent chemical resistance, shrinking percentage
It is low, adhesive strength is high, high mechanical strength, electrical insulating property are excellent, therefore be widely used in the fields such as coating, adhesive, ink.But
It is that epoxy resin brittleness is larger, toughness and weatherability are poor, limit its application.There are many ways to epoxy resin roughening, rubber
Glue toughening is a kind of common method.It is logical for epoxy resin toughened rubber since epoxy resin is a kind of polarity macromolecule
It is often with polar nitrile rubber, neoprene etc., the compatibility of nonpolar natural rubber and epoxy resin is poor, limitation
It is as the application in terms of epoxy resin roughening.
Janus material is that a kind of surface chemistry composition is different, anisotropic center asymmetric particle.Chinese patent CN
103204508 B disclose Janus material with double properties and preparation method thereof, using polymeric colloid particle as template,
By seeded emulsion polymerization method, it is based on interface self assembly and phase separating mechanism, obtains hybrid Janus particle,
It is inorganic material that have generator terminal, which be polymer containing double bonds, the other end such as polystyrene, polyacrylate,.Really as expanding material
The Janus material used forms demand by richer to its both ends, is modified respectively to the both ends of Janus material, can be with
Regulate and control its chemical property, so that it is shown the phase interface behavior of very abundant in Polymer Blending System, play " riveting getting along
Nail " effect.2008, anisotropic single ball Janus particle was applied in PS/PMMA co-mixing system by Walther etc. for the first time,
It was found that even if Janus particle also can be orderly at polymer two-phase interface under high temperature and the twin-screw immixture of high shear
Arrangement, and have strong suction-operated to the polymer of interface two sides, the size of dispersed phase is with Janus amount of particles
Increase and reduce, its compatibilization effect is better than block copolymer.Currently, Janus material is mainly concentrated as the research of expanding material
In thermoplastic resin, the application range of Janus material is limited.Therefore, it is simple to find a kind of synthetic method, is applied to thermosetting property
The Janus material of resin alloy polymer compatibilizer is very necessary.
Summary of the invention
The purpose of the present invention is to provide a kind of for the Janus expanding material of rubber-toughened epoxy resin and its preparation side
Method, this method is simple and feasible, has expanded the application range of Janus material.
To achieve the goals above, the invention adopts the following technical scheme:
A kind of preparation method of the Janus expanding material for rubber-toughened epoxy resin, comprising the following steps:
1) it polymerization reaction: is reacted with lauryl mercaptan at polydivinylbenezene end
Polydivinylbenezene/silica Janus material (is pressed into document Macromolecules 2015,48:2715
2722 method preparation) and azo-bis-isobutyl cyanide be placed in flask, addition toluene is transferred to 45 ~ 95 DEG C of water-bath after ultrasonic disperse
In, magnetic agitation after being passed through nitrogen 0.5 ~ 1 hour, is slowly dropped into lauryl mercaptan, react 12 ~ 48 hours, product pass through from
The heart, washing obtain lauryl mercaptan-polydivinylbenezene/silica Janus material,
Wherein, polydivinylbenezene/silica Janus material, toluene, lauryl mercaptan and azo-bis-isobutyl cyanide
Mass ratio is 1:17:10~30:0.055~0.62；
2) it coupling reaction: is reacted with γ-methacryloxypropyl trimethoxy silane at silica end
By lauryl mercaptan-polydivinylbenezene/silica Janus material and γ-methyl-prop made from step 1)
Alkene acryloxypropylethoxysilane trimethoxy silane is placed in flask, and toluene is added, is transferred in 45 ~ 95 DEG C of water-bath after ultrasonic disperse, magnetic
Power stirring, reacts 8 ~ 24 hours, product is centrifuged, is washed, and lauryl mercaptan-polydivinylbenezene/silica-is obtained
γ-methacryloxypropyl trimethoxy silane Janus material, it is as described for rubber-toughened epoxy resin
Janus expanding material,
Wherein, lauryl mercaptan-polydivinylbenezene/silica Janus material, toluene and γ-methacryl
The ratio of oxygroup propyl trimethoxy silicane is 1 g: 17 g: 0.1 ~ 0.5 mL.
Further, the step 1) and mode of washing 2) are as follows: product uses ethanol washing three after being washed three times with toluene again
It is secondary.
Polydivinylbenezene described in step 1) of the present invention/silica Janus material is by document
It is prepared by the method for Macromolecules 2015,48:2715 2722.
The invention adopts the above technical scheme, is silica by one end, and the other end is the Janus particle of divinylbenzene
Both ends are modified, the expanding material epoxy resin toughened as liquid isoprene rubber.Specific method is to pass sequentially through to two
Vinyl benzene terminates branch lauryl mercaptan, silica terminates branch γ-methacryloxypropyl trimethoxy silane, modified
To Janus material can reduce interface embedded in liquid isoprene rubber, on epoxy resin phase interface as expanding material
Power, inhibition mutually separate.
The Janus increase-volume epoxy resin toughened suitable for liquid isoprene rubber can be made using the above method in the present invention
Agent has the advantage that
1. preparation method is simple for Janus bead expanding material, it is suitble to industrialized production.
2. lauryl mercaptan-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silicon
Alkane Janus material ends are reacted respectively with composite material two-phase, wherein lauryl mercaptan end participates in the vulcanization of rubber phase, γ-
The crosslinking curing of methacryloxypropyl trimethoxy silane participation epoxy resin.Modified Janus bead is for increasing
Hold liquid isoprene rubber/epoxy resin composite material, it can be with phased array at two-phase interface.
3. Janus bead has anisotropic chemical structure, possess phase interface behavior abundant, to liquid isoamyl two
Alkene rubber/epoxy resin composite material compatibilization is strong.
Detailed description of the invention
Fig. 1 is the infrared spectrum of Janus expanding material (product I) made from the embodiment of the present invention 1.
Fig. 2 is the scanning electron microscope (SEM) photograph of composite material I made from application examples 1 of the invention.
Fig. 3 is the scanning electron microscope (SEM) photograph of composite material II made from application examples 1 of the invention.
Specific embodiment
Below with reference to specific embodiment, the invention will be further described.
Embodiment 1
The preparation method of Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
0.5 g polydivinylbenezene/silica Janus material and 0.0281 g azo-bis-isobutyl cyanide are placed in a flask
In, 8.51 g toluene are added, are transferred in 50 DEG C of water-bath after ultrasonic disperse, magnetic agitation, leads to nitrogen after 0.5 hour, slowly drips
Enter 6.01g lauryl mercaptan, react 24 hours, product after being centrifuged, with toluene wash three times, ethanol washing obtain ten three times
Dialkyl group mercaptan-polydivinylbenezene/silica Janus material.
2) coupling reaction:
Take lauryl mercaptan-polydivinylbenezene made from step 1)/silica Janus material 0.46 g and 0.05
ML γ-methacryloxypropyl trimethoxy silane is placed in a flask, and toluene is added, is transferred to 50 DEG C after ultrasonic disperse
In water-bath, magnetic agitation is reacted 12 hours, and product is through being centrifuged, and toluene washs three times, and ethanol washing obtains dodecyl sulphur three times
Alcohol-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silane Janus material (product I).
Fig. 1 is the infrared spectrum of Janus expanding material (product I) made from embodiment 1, it can be seen from Fig. 1 that 3080,3057 and
3025 cm-1The stretching vibration peak of C-H on phenyl ring, 1601 cm-1The skeletal vibration of phenyl ring, 1493 cm-1With 1450 cm-1Locate benzene
Stretching vibration and in-plane bending vibration peak, 757 and 701cm in the face of ring-1The out-of-plane bending vibration of C-H derives from two on phenyl ring
Vinyl benzene； 2925 cm-1With 2850 cm-1It is lauryl mercaptan and γ-methacryloxypropyl trimethoxy silicon
Alkane saturation-CH and-CH2Stretching vibration peak；1724 cm-1The stretching vibration peak of C=O is by γ-methacryloxypropyl three
Methoxy silane causes；The characteristic absorption of silica Si-O key is in 473 cm-1Place.
Embodiment 2
The preparation method of Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
0.48 g polydivinylbenezene/silica Janus material and 0.2421 g azo-bis-isobutyl cyanide are placed in a burning
In bottle, 8.20 g toluene are added, are transferred in 70 DEG C of water-bath after ultrasonic disperse, magnetic agitation, leads to nitrogen after 0.5 hour, slowly
Instill 9.64 g lauryl mercaptans, react 24 hours, product after being centrifuged, with toluene wash three times, ethanol washing three times must
To lauryl mercaptan-polydivinylbenezene/silica Janus material.
2) coupling reaction:
Take lauryl mercaptan-polydivinylbenezene made from step 1)/silica Janus material 0.30 g and 0.09
ML γ-methacryloxypropyl trimethoxy silane is placed in a flask, and 5.15 g toluene are added, are transferred to after ultrasonic disperse
In 70 DEG C of water-bath, magnetic agitation is reacted 24 hours, and product is after being centrifuged, and toluene washs three times, and ethanol washing obtains ten three times
Dialkyl group mercaptan-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silane Janus material
(product II).
Embodiment 3
The preparation method of Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
0.48 g polydivinylbenezene/silica Janus material and 0.1457 g azo-bis-isobutyl cyanide are placed in a burning
In bottle, 8.23 g toluene are added, are transferred in 90 DEG C of water-bath after ultrasonic disperse, magnetic agitation, leads to nitrogen after 0.5 hour, slowly
Instill 14.50 g lauryl mercaptans, react 48 hours, product after being centrifuged, with toluene wash three times, ethanol washing three times must
To lauryl mercaptan-polydivinylbenezene/silica Janus material.
2) coupling reaction:
Take lauryl mercaptan-polydivinylbenezene made from step 1)/silica Janus material 0.31 g and 0.12
ML γ-methacryloxypropyl trimethoxy silane is placed in a flask, and 5.20 g toluene are added, are transferred to after ultrasonic disperse
In 90 DEG C of water-bath, magnetic agitation is reacted 12 hours, and product is after being centrifuged, and toluene washs three times, and ethanol washing obtains ten three times
Dialkyl group mercaptan-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silane Janus material
(product III).
Embodiment 4
The preparation method of Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
0.51 g polydivinylbenezene/silica Janus material and 0.1009 g azo-bis-isobutyl cyanide are placed in a burning
In bottle, 8.69 g toluene are added, are transferred in 70 DEG C of water-bath after ultrasonic disperse, magnetic agitation, leads to nitrogen after 0.5 hour, slowly
Instill 10.21 g lauryl mercaptans, react 36 hours, product after being centrifuged, with toluene wash three times, ethanol washing three times must
To lauryl mercaptan-polydivinylbenezene/silica Janus material.
2) coupling reaction:
Take lauryl mercaptan-polydivinylbenezene made from step 1)/silica Janus material 0.39 g and 0.08
ML γ-methacryloxypropyl trimethoxy silane is placed in a flask, and 6.63 g toluene are added, are transferred to after ultrasonic disperse
In 70 DEG C of water-bath, magnetic agitation is reacted 8 hours, and product is after being centrifuged, and toluene washs three times, and ethanol washing obtains ten three times
Dialkyl group mercaptan-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silane Janus material
(product IV).
Embodiment 5
The preparation method of Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
1.11g polydivinylbenezene/silica Janus material and 0.0673 g azo-bis-isobutyl cyanide are placed in a flask
In, 18.92g toluene is added, is transferred in 60 DEG C of water-bath after ultrasonic disperse, magnetic agitation, leads to nitrogen after 0.5 hour, slowly drips
Enter 22.20 g lauryl mercaptans, react 24 hours, product after being centrifuged, with toluene wash three times, ethanol washing obtains three times
Lauryl mercaptan-polydivinylbenezene/silica Janus material.
2) coupling reaction:
Take lauryl mercaptan-polydivinylbenezene made from step 1)/silica Janus material 0.82 g and 0.25
ML γ-methacryloxypropyl trimethoxy silane is placed in a flask, and 14.09 g toluene are added, turn after ultrasonic disperse
Enter in 90 DEG C of water-bath, magnetic agitation, react 24 hours, product is after being centrifuged, and toluene washs three times, and ethanol washing obtains three times
Lauryl mercaptan-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silane Janus material
(product V).
Embodiment 6
The preparation method of Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
2.56 g polydivinylbenezene/silica Janus material and 1.0262 g azo-bis-isobutyl cyanides are placed in a burning
In bottle, 43.50 g toluene are added, are transferred in 70 DEG C of water-bath after ultrasonic disperse, magnetic agitation, leads to nitrogen after 0.5 hour, delay
It is slow to instill 25.67 g lauryl mercaptans, react 24 hours, product after being centrifuged, with toluene wash three times, ethanol washing three times
Obtain lauryl mercaptan-polydivinylbenezene/silica Janus material.
2) coupling reaction:
Take lauryl mercaptan-polydivinylbenezene made from step 1)/silica Janus material 1.87 g and 0.94
ML γ-methacryloxypropyl trimethoxy silane is placed in a flask, and 31.84 g toluene are added, turn after ultrasonic disperse
Enter in 90 DEG C of water-bath, magnetic agitation, react 16 hours, product is after being centrifuged, and toluene washs three times, and ethanol washing obtains three times
Lauryl mercaptan-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silane Janus material
(product VI).
Embodiment 7
The preparation method of Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
3.01 g polydivinylbenezene/silica Janus material and 0.2431 g azo-bis-isobutyl cyanide are placed in a burning
In bottle, 50.98 g toluene are added, are transferred in 90 DEG C of water-bath after ultrasonic disperse, magnetic agitation, leads to nitrogen after 0.5 hour, delay
It is slow to instill 45.11 g lauryl mercaptans, react 24 hours, product after being centrifuged, with toluene wash three times, ethanol washing three times
Obtain lauryl mercaptan-polydivinylbenezene/silica Janus material.
2) coupling reaction:
Take lauryl mercaptan-polydivinylbenezene made from step 1)/silica Janus material 2.24 g and 0.45
ML γ-methacryloxypropyl trimethoxy silane is placed in a flask, and 38.06 g toluene are added, turn after ultrasonic disperse
Enter in 70 DEG C of water-bath, magnetic agitation, react 18 hours, product is after being centrifuged, and toluene washs three times, and ethanol washing obtains three times
Lauryl mercaptan-polydivinylbenezene/silica-γ-methacryloxypropyl trimethoxy silane Janus material
(product VII).
Embodiment 8
The preparation method of Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
Polydivinylbenezene/silica Janus material and azo-bis-isobutyl cyanide are placed in flask, toluene is added, is surpassed
It is transferred in 45 DEG C of water-bath after sound dispersion, magnetic agitation after being passed through nitrogen 0.5 hour, is slowly dropped into lauryl mercaptan, reaction
12 hours, product after being centrifuged, toluene wash three times, ethanol washing three times, obtain lauryl mercaptan-polydivinylbenezene/
Silica Janus material,
Wherein, polydivinylbenezene/silica Janus material, toluene, lauryl mercaptan and azo-bis-isobutyl cyanide
Mass ratio is 1:17:10:0.055；
2) coupling reaction:
By lauryl mercaptan-polydivinylbenezene/silica Janus material and γ-methyl-prop made from step 1)
Alkene acryloxypropylethoxysilane trimethoxy silane is placed in flask, and toluene is added, is transferred in 45 DEG C of water-bath after ultrasonic disperse, magnetic force
Stirring is reacted 8 hours, and product is after being centrifuged, and toluene washs three times, and ethanol washing three times, obtains the poly- diethyl of lauryl mercaptan-
Alkenyl benzene/silica-γ-methacryloxypropyl trimethoxy silane Janus material, it is as described to increase for rubber
The Janus expanding material of tough epoxy resin,
Wherein, lauryl mercaptan-polydivinylbenezene/silica Janus material, toluene and γ-methacryl
The ratio of oxygroup propyl trimethoxy silicane is 1 g: 17 g: 0.1 mL.
Embodiment 9
A kind of preparation method of the Janus expanding material for rubber-toughened epoxy resin:
1) polymerization reaction:
Polydivinylbenezene/silica Janus material and azo-bis-isobutyl cyanide are placed in flask, toluene is added, is surpassed
It is transferred in 95 DEG C of water-bath after sound dispersion, magnetic agitation, after being passed through nitrogen 1 hour, is slowly dropped into lauryl mercaptan, reaction 48
Hour, product is centrifuged, is washed, lauryl mercaptan-polydivinylbenezene/silica Janus material is obtained,
Wherein, polydivinylbenezene/silica Janus material, toluene, lauryl mercaptan and azo-bis-isobutyl cyanide
Mass ratio is 1:17:30:0.62；
2) coupling reaction:
By lauryl mercaptan-polydivinylbenezene/silica Janus material and γ-methyl-prop made from step 1)
Alkene acryloxypropylethoxysilane trimethoxy silane is placed in flask, and toluene is added, is transferred in 95 DEG C of water-bath after ultrasonic disperse, magnetic force
Stirring is reacted 24 hours, and product is after being centrifuged, and toluene washs three times, and ethanol washing three times, obtains lauryl mercaptan-poly- two
Vinyl benzene/silica-γ-methacryloxypropyl trimethoxy silane Janus material, it is as described to be used for rubber
Epoxy resin toughened Janus expanding material,
Wherein, lauryl mercaptan-polydivinylbenezene/silica Janus material, toluene and γ-methacryl
The ratio of oxygroup propyl trimethoxy silicane is 1 g: 17 g: 0.5 mL.
Application examples 1
Take 1.01 g liquid isoprene rubbers, 0.05 g cumyl peroxide, 0.06 g triallyl isocyanurate
With 4.02g epoxy blend, 3h is stirred at 90 DEG C, and 0.99 g, 4,4-diaminodiphenyl-methane, stirring 5 is then added
Min obtains composite material I in 120 DEG C of solidifications 2 h, 160 DEG C of 2 h of solidification.
Take 1.06 g liquid isoprene rubbers, 0.06 g cumyl peroxide, 0.06 g triallyl isocyanurate,
4.11 g epoxy blends, and 0.18 g Janus bead expanding material (product II of embodiment 2) is added, it is stirred at 90 DEG C
3 h are mixed, 1.03 g, 4,4-diaminodiphenyl-methane is then added, stir 5 min, in 120 DEG C of 2 h of solidification, 160 DEG C solid
Change 2 h, obtains composite material II.
Fig. 2 and Fig. 3 is respectively the scanning electron microscope (SEM) photograph of composite material I and composite material II, the ring without Janus expanding material
Oxygen resin/isoprene rubber co-mixing system phase size is big, and phase interface is clear, and isoprene rubber is mutually from asphalt mixtures modified by epoxy resin when brittle failure
Rouge continuous phase falls off (Fig. 2).And Janus expanding material is amphipathic due to self structure, in epoxy resin/isoprene rubber
It can be orderly distributed in co-mixing system (Fig. 3), the interfacial adhesion of reinforced epoxy and isoprene rubber, it is different to reduce dispersion
The phase size of pentadiene rubber, epoxy resin/isoprene rubber composite material of Janus particle increase-volume is in external force
Under, isoprene rubber does not fall off from continuous phase largely.
Claims (3)
1. a kind of preparation method of the Janus expanding material for rubber-toughened epoxy resin, it is characterised in that: it includes following step
It is rapid:
1) polymerization reaction:
Polydivinylbenezene/silica Janus material and azodiisobutyronitrile are placed in flask, toluene, ultrasound point is added
It is transferred in 45 ~ 95 DEG C of water-bath after dissipating, magnetic agitation after being passed through nitrogen 0.5 ~ 1 hour, is slowly dropped into lauryl mercaptan, instead
It answers 12 ~ 48 hours, product is centrifuged, is washed, lauryl mercaptan-polydivinylbenezene/silica Janus material is obtained,
Wherein, the matter of polydivinylbenezene/silica Janus material, toluene, lauryl mercaptan and azodiisobutyronitrile
Amount is than being 1:17:10~30:0.055~0.62；
2) coupling reaction:
By lauryl mercaptan-polydivinylbenezene/silica Janus material and γ-methacryl made from step 1)
Oxygroup propyl trimethoxy silicane is placed in flask, and toluene is added, is transferred in 45 ~ 95 DEG C of water-bath after ultrasonic disperse, magnetic force stirs
It mixes, reacts 8 ~ 24 hours, product is centrifuged, is washed, and lauryl mercaptan-polydivinylbenezene/silica-γ-first is obtained
Base acryloyloxypropyltrimethoxysilane Janus material, the as described Janus increase-volume for being used for rubber-toughened epoxy resin
Agent,
Wherein, lauryl mercaptan-polydivinylbenezene/silica Janus material, toluene and γ-methacryloxy
The ratio of propyl trimethoxy silicane is 1 g: 17 g: 0.1 ~ 0.5 mL.
2. a kind of preparation method of Janus expanding material for rubber-toughened epoxy resin according to claim 1, special
Sign is: the mode of washing be washed three times with toluene after again with ethanol washing three times.
3. lauryl mercaptan-polydivinylbenezene/silica-that preparation method according to claim 1 or 2 obtains
γ-methacryloxypropyl trimethoxy silane Janus material.
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| CN101759973A (en) * | 2010-01-19 | 2010-06-30 | 华南理工大学 | Preparation method for thermoset resin/waste rubber powder/waste tire fiber composite material |
| CN103013042A (en) * | 2011-09-28 | 2013-04-03 | 深圳光启高等理工研究院 | Metamaterial dielectric substrate and processing method thereof |
| CN104725776A (en) * | 2013-12-19 | 2015-06-24 | 徐唱 | Hydantoin type epoxy resin toughening agent and preparation method thereof |
| CN104987464A (en) * | 2015-07-06 | 2015-10-21 | 安徽成方新材料科技有限公司 | Macromolecule absorbent with modified high thermal stability based on nanosilicon dioxide polylactic acid and preparation method thereof |
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