CN108525618A - A kind of preparation method of double-walled room microcapsules - Google Patents
A kind of preparation method of double-walled room microcapsules Download PDFInfo
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- CN108525618A CN108525618A CN201810310583.6A CN201810310583A CN108525618A CN 108525618 A CN108525618 A CN 108525618A CN 201810310583 A CN201810310583 A CN 201810310583A CN 108525618 A CN108525618 A CN 108525618A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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- Polymers & Plastics (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Abstract
The present invention relates to a kind of preparation methods of double-walled room microcapsules, have macromolecular amphiphilic and that polymerization can be caused again as stabilizer using a kind of, prepare the Caplet of cladding renovation agent, and using Caplet as the stabilizer of Pickering lotions, using mercaptan/isocyanates point hit method, the method for being adsorbed on large capsule surface by stablizing capsule self assembly prepares double-walled room microcapsules.Prepared double-walled room microcapsules inner wall and outer wall Caplet have abyss influence simultaneously containing renovation agent, it can be achieved that response crackle repeatedly discharges the performance of renovation agent on the preparation of Smart self-repairing material.
Description
Technical field
The present invention relates to a kind of preparation methods of double-walled room microcapsules, and in particular to has with one kind amphiphilic and can be again
Cause the macromolecular of polymerization as stabilizer, prepares the Caplet of cladding renovation agent, and using Caplet as Pickering lotions
Stabilizer, the preparation method of double-walled room microcapsules is prepared using mercaptan/isocyanates point hit method.
Background technology
Microcapsules refer to being encapsulated to functional liquid, solid or the gas of dispersibility, and being formed has core shell structure
Miniature memory device, outer capsule layer shell become barrier, protect the nucleome material not performance failure in external environment.In recent years,
Microcapsules are widely used in as reservoir storage liquid in Smart self-repairing material, achieve significant achievement, simultaneously also
The development of polymer self-healing system is pushed.Microcapsules serve as the storage medium of renovation agent in polymeric matrix, are damaged in material
Core material is released when hindering.Compared to other methods, there is the development prospect of bigger based on microcapsule-type self-repair material, but there are still difficulties
The problem of to realize multiple selfreparing.For the target repeatedly repaired of realization, the present invention is designed and is provided outside a kind of large capsule
Wall surface adsorbs the double-walled cell structure microcapsules of Caplet, and small size capsule and large capsule can encapsulate renovation agent simultaneously, and crackle expands
Exhibition can repeatedly discharge renovation agent, be repaired to matrix.
Invention content
Technical problems to be solved
In order to avoid the shortcomings of the prior art, the present invention proposes a kind of preparation method of double-walled room microcapsules, provide
One kind, for Pickering lotions, the micro- glue in multi wall room being prepared using mercaptan/isocyanates point hit method with amphiphilic self-stabilization microcapsules
The preparation method of capsule.The double-walled room microcapsules inner wall and outer wall Caplet prepared in this method simultaneously contain renovation agent, it can be achieved that
Multiple reparation to matrix.
Technical solution
The preparation method of a kind of double-walled room microcapsules, it is characterised in that steps are as follows：
Step 1：1,1- diphenylethlenes DPE and glycidyl acrylate GMA are mixed with deionized water, heating water bath
To 65~80 DEG C；Wherein, the mass fraction that glycidyl acrylate GMA accounts for ionized water is 5~14%, 1,1- diphenyl second
The mass fraction that alkene DPE accounts for GMA is 0.6~3%；
Step 2：The initiator solution of 45~180mL is added, under stiring, after heating in water bath for reaction 16~for 24 hours, rotation
Moisture removal is boiled off, DPE-PGMA prepolymers are obtained；0.5~2.0g/L of concentration of the initiator solution；
Step 3：DPE-PGMA prepolymers are added in the bag filter after activation, sealing；It is put into deionized water and dialyses one week,
The deionized water for impregnating bag filter and the now conductivity of deionized water processed are measured respectively, seek absolute value after difference<0.001 pours out pre-polymerization
Object；
Step 4：DPE-PGMA prepolymers, monomer, core material A are mixed with deionized water, stirring high speed emulsification 10~
40min；Heating water bath to 80 DEG C, 150~500rmp of mechanical agitation, 10~16h of heating in water bath for reaction, wash 1 time by centrifugation, alcohol again,
Washing 3 times, obtains microcapsules；The mass fraction that wherein DPE-PGMA prepolymers account for overall reaction liquid is 7%~14%, monomer and core material
The mass fraction that A accounts for overall reaction liquid respectively is 4~15%；
Step 5：The microcapsules of step 4 are prepared into the capsule lotion that mass concentration is 0.5%~6%, with shell monomers sulphur
Mechanical agitation high speed 5~10min of emulsification after alcohol, isocyanates, core material B mixing, then 1~2mL triethylamines are added dropwise, it reacts at room temperature
After 20min, through suction filtration, washing, drying to get double-walled room microcapsules；Wherein, the functional group of shell monomers mercaptan and isocyanates
Molar ratio is 1: 1, and the mass ratio of core material B and shell monomers mercaptan is 0.5~2: 1.
The initiator is potassium peroxydisulfate KPS, ammonium persulfate APS, azodiisobutyronitrile AIBN or dibenzoyl peroxide
BPO。
The monomer is methyl methacrylate MMA, diethylbenzene DVB or two kinds of monomers with arbitrary proportion mixture.
The core material A be dicyclopentadiene DCPD, epoxy E-51, one kind in epoxy 184, two or more with appoint
The mixture of meaning ratio mixing.
The mercaptan is trimethylolpropane (3- thio propanes acid esters) TMMP, three (2- ethoxys) chlorinated isocyanurates-three
A kind of in (mercaptopropionic acid ester) TEMPIC, pentaerythrite four (3-thiopropionate) PETMP, two or more arbitrary ratio
Mixed mixture.
The isocyanates is isophorone diisocyanate IPDI, toluene di-isocyanate(TDI) TDI, two isocyanide of hexa-methylene
A kind of, two or more arbitrary mixed mixture of ratio in acid esters HDI.
The core material B is dicyclopentadiene DCPD, dicyclopentadiene and toluene at least one in arbitrary proportion mixture
Kind.
Advantageous effect
A kind of preparation method of double-walled room microcapsules proposed by the present invention has amphiphilic and can cause again poly- with one kind
The macromolecular of conjunction prepares the Caplet of cladding renovation agent, and using Caplet as the stabilization of Pickering lotions as stabilizer
Agent, using mercaptan/isocyanates point hit method, the method for being adsorbed on large capsule surface by stablizing capsule self assembly prepares double-walled
Room microcapsules.Prepared double-walled room microcapsules inner wall and outer wall Caplet are simultaneously containing renovation agent, it can be achieved that response crackle is more
The performance of secondary release renovation agent, has abyss influence to the preparation of Smart self-repairing material.
Description of the drawings
Fig. 1 is P (GMA-co-MMA-co-DVB)@DCPD/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules in example 1
SEM figure；
Fig. 2 is P (GMA-co-MMA-co-DVB)@DCPD/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules in example 1
TGA figure；
Fig. 3 is P (GMA-co-MMA-co-DVB)@DCPD/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules in example 1
Grain size distribution.
Specific implementation mode
In conjunction with embodiment, attached drawing, the invention will be further described：
Embodiment 1：It is prepared by P (GMA-co-MMA-co-DVB)@DCPD/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules
DPE, glycidyl acrylate (GMA) and deionized water are mixed, are added in there-necked flask, mechanical agitation, water-bath
It is heated to 80 DEG C.Wherein, the mass fraction that GMA accounts for ionized water is that the mass fraction that 8.75%, DPE accounts for GMA is 1.29%；Match
The water soluble starter of 0.75g/L processed is added after water-bath pot temperature rises to 80 DEG C in 120mL to there-necked flask.Mechanical agitation
Under, after heating in water bath for reaction 16~for 24 hours, revolving removes moisture removal；DPE-PGMA prepolymers are added in the bag filter after activation, close
Envelope.It is put into deionized water and dialyses one week, measure the deionized water for impregnating bag filter and the now conductivity of deionized water processed respectively,
Seek absolute value after difference<0.001, to prepolymer is gone out, solid content is measured after revolving.
DPE-PGMA prepolymers, DVB, MMA and dicyclopentadiene (DPCD) and deionized water are mixed, there-necked flask is added
It is interior, mechanical agitation high speed emulsification 30min.Reaction solution after emulsification is the uniform milky of color, and heating water bath is to 80 DEG C, machinery
It stirs under 200rmp/min, 10~16h of heating in water bath for reaction, centrifugation, alcohol are washed 1 time, wash 3 times to get small size P (GMA-co-
MMA-co-DVB)@DCPD microcapsules.Wherein DPE-PGMA prepolymers account for overall reaction liquid mass fraction be 11.57%, monomer and
The mass ratio that the mass fraction that DCPD accounts for overall reaction liquid respectively is 8.18%, 6.945%, DVB and MMA is 1.25：1；
The small size capsule lotion that mass concentration is 1.5% is prepared, is added in three-necked flask.By trimethylolpropane (3-
Thio propane acid esters) (TMMP), isophorone diisocyanate (IPDI) and DCPD be mixed evenly, three-necked flask is added
In, mechanical agitation high speed 5~10min of emulsification pours into dropwise addition 1~2mL triethylamines in beaker.After reacting at room temperature 20min, through taking out
Filter, washing, drying are to get P (GMA-co-MMA-co-DVB)@DCPD/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules system
Standby double-walled room microcapsules.Wherein, functional group's molar ratio of mercaptan and isocyanates is 1：1, DCPD and Shell Materials monomer matter
Amount is than being 1：1.
Embodiment 2:It is prepared by P (GMA-co-MMA-co-DVB)@E-51/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules
DPE, glycidyl acrylate (GMA) and deionized water are mixed, are added in there-necked flask, mechanical agitation, water-bath
It is heated to 80 DEG C.Wherein, the mass fraction that GMA accounts for ionized water is that the mass fraction that 8.75%, DPE accounts for GMA is 1.29%；Match
The water soluble starter of 0.75g/L processed is added after water-bath pot temperature rises to 80 DEG C in 120mL to there-necked flask.Mechanical agitation
Under, after heating in water bath for reaction 16~for 24 hours, revolving removes moisture removal；DPE-PGMA prepolymers are added in the bag filter after activation, close
Envelope.It is put into deionized water and dialyses one week, measure the deionized water for impregnating bag filter and the now conductivity of deionized water processed respectively,
Seek absolute value after difference<0.001, to prepolymer is gone out, solid content is measured after revolving；
DPE-PGMA prepolymers, DVB, MMA and epoxy (E-51) and deionized water are mixed, are added in there-necked flask, machinery
Stirring high speed emulsification 30min.Reaction solution after emulsification is the uniform milky of color, and heating water bath is to 80 DEG C, mechanical agitation
Under 200rmp/min, 10~16h of heating in water bath for reaction, centrifugation, alcohol are washed 1 time, wash 3 times to get small size P (GMA-co-MMA-
Co-DVB)@E-51 microcapsules.The mass fraction that wherein DPE-PGMA prepolymers account for overall reaction liquid is 10.84%, monomer and E-51
The mass ratio that the mass fraction for accounting for overall reaction liquid respectively is 6.19%, 7.05%, DVB and MMA is 1：1；
The small size capsule lotion that mass concentration is 1.5% is prepared, is added in three-necked flask.By trimethylolpropane (3-
Thio propane acid esters) (TMMP), isophorone diisocyanate (IPDI) and DCPD be mixed evenly, three-necked flask is added
In, mechanical agitation high speed 5~10min of emulsification pours into dropwise addition 1~2mL triethylamines in beaker.After reacting at room temperature 20min, through taking out
Filter, washing, drying are double to get the preparation of P (GMA-co-MMA-DVB)@E-51/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules
Wall room microcapsules.Wherein, functional group's molar ratio of mercaptan and isocyanates is 1：1, DCPD and Shell Materials monomer mass ratio
It is 1：1.
Embodiment 3：It is prepared by P (GMA-co-DVB)@DCPD/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules
DPE, glycidyl acrylate (GMA) and deionized water are mixed, are added in there-necked flask, mechanical agitation, water-bath
It is heated to 80 DEG C.Wherein, the mass fraction that GMA accounts for ionized water is that the mass fraction that 8.75%, DPE accounts for GMA is 1.29%；Match
The water soluble starter of 0.75g/L processed is added after water-bath pot temperature rises to 80 DEG C in 120mL to there-necked flask.Mechanical agitation
Under, after heating in water bath for reaction 16~for 24 hours, revolving removes moisture removal；DPE-PGMA prepolymers are added in the bag filter after activation, close
Envelope.It is put into deionized water and dialyses one week, measure the deionized water for impregnating bag filter and the now conductivity of deionized water processed respectively,
Seek absolute value after difference<0.001, to prepolymer is gone out, solid content is measured after revolving.
DPE-PGMA prepolymers, DVB and dicyclopentadiene (DPCD) and deionized water are mixed, are added in there-necked flask, machine
Tool stirring high speed emulsification 30min.Reaction solution after emulsification is the uniform milky of color, and heating water bath is to 80 DEG C, mechanical agitation
Under 200rmp/min, 10~16h of heating in water bath for reaction, centrifugation, alcohol are washed 1 time, wash 3 times to get small size P (GMA-co-MMA-
Co-DVB)@DCPD microcapsules.The mass fraction that wherein DPE-PGMA prepolymers account for overall reaction liquid is 7%, monomer and DCPD difference
The mass fraction for accounting for overall reaction liquid is 7%；
The small size capsule lotion that mass concentration is 3% is prepared, is added in three-necked flask.By trimethylolpropane (3- mercaptos
Base cyclopropanecarboxylic acid ester) (TMMP), isophorone diisocyanate (IPDI) and DCPD be mixed evenly, be added in three-necked flask,
Mechanical agitation high speed 5~10min of emulsification, pours into dropwise addition 1~2mL triethylamines in beaker.After reacting at room temperature 20min, through suction filtration, water
It washes, dry and prepare the micro- glue in double-walled room to get P (GMA-co-DVB)@DCPD/ (TMMP-co-IPDI)@DCPD double-walleds room microcapsules
Capsule.Wherein, functional group's molar ratio of mercaptan and isocyanates is 1：1, DCPD and Shell Materials monomer mass ratio be 1：1.
Claims (7)
1. a kind of preparation method of double-walled room microcapsules, it is characterised in that steps are as follows：
Step 1：1,1- diphenylethlenes DPE and glycidyl acrylate GMA are mixed with deionized water, heating water bath to 65
~80 DEG C；Wherein, the mass fraction that glycidyl acrylate GMA accounts for ionized water is 5~14%, 1,1- diphenylethlene
The mass fraction that DPE accounts for GMA is 0.6~3%；
Step 2：The initiator solution of 45~180mL is added, under stiring, after heating in water bath for reaction 16~for 24 hours, revolving is gone
Moisture removal obtains DPE-PGMA prepolymers；0.5~2.0g/L of concentration of the initiator solution；
Step 3：DPE-PGMA prepolymers are added in the bag filter after activation, sealing；It is put into deionized water and dialyses one week, respectively
The deionized water for impregnating bag filter and the now conductivity of deionized water processed are measured, absolute value after difference is sought<0.001 pours out prepolymer；
Step 4：DPE-PGMA prepolymers, monomer, core material A are mixed with deionized water, 10~40min of stirring high speed emulsification；Again
Heating water bath to 80 DEG C, 150~500rmp of mechanical agitation, 10~16h of heating in water bath for reaction, wash 1 time by centrifugation, alcohol, washes 3 times,
Obtain microcapsules；The mass fraction that wherein DPE-PGMA prepolymers account for overall reaction liquid is 7%~14%, and monomer and core material A are accounted for respectively
The mass fraction of overall reaction liquid is 4~15%；
Step 5：The microcapsules of step 4 are prepared into the capsule lotion that mass concentration is 0.5%~6%, with shell monomers mercaptan, different
Mechanical agitation high speed 5~10min of emulsification after cyanate, core material B mixing, then 1~2mL triethylamines are added dropwise, react at room temperature 20min
Afterwards, through suction filtration, washing, drying to get double-walled room microcapsules；Wherein, the functional group mole of shell monomers mercaptan and isocyanates
Than being 1: 1, the mass ratio of core material B and shell monomers mercaptan is 0.5~2: 1.
2. the preparation method of double-walled room microcapsules according to claim 1, it is characterised in that：The initiator is potassium peroxydisulfate
KPS, ammonium persulfate APS, azodiisobutyronitrile AIBN or dibenzoyl peroxide BPO.
3. the preparation method of double-walled room microcapsules according to claim 1, it is characterised in that：The monomer is methacrylic acid
Methyl esters MMA, diethylbenzene DVB or two kinds of monomers are with arbitrary proportion mixture.
4. the preparation method of double-walled room microcapsules according to claim 1, it is characterised in that：The core material A is bicyclic penta 2
Alkene DCPD, epoxy E-51, one kind in epoxy 184, two or more mixture mixed with arbitrary proportion.
5. the preparation method of double-walled room microcapsules according to claim 1, it is characterised in that：The mercaptan is trihydroxy methyl third
Alkane (3- thio propanes acid esters) TMMP, three (2- ethoxys) chlorinated isocyanurates-three (mercaptopropionic acid ester) TEMPIC, pentaerythrite four
A kind of, two or more arbitrary mixed mixture of ratio in (3-thiopropionate) PETMP.
6. the preparation method of double-walled room microcapsules according to claim 1, it is characterised in that：The isocyanates is different Fo Er
It is a kind of in ketone diisocyanate IPDI, toluene di-isocyanate(TDI) TDI, hexamethylene diisocyanate HDI, two or more
The one arbitrary mixed mixture of ratio.
7. the preparation method of double-walled room microcapsules according to claim 1, it is characterised in that：The core material B is bicyclic penta 2
Alkene DCPD, dicyclopentadiene and toluene are at least one of arbitrary proportion mixture.
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| CN110563921A (en) * | 2019-09-16 | 2019-12-13 | 西北工业大学 | Method for preparing isocyanate microcapsule by mercaptan-isocyanate click chemical reaction |
| CN111334176A (en) * | 2020-03-09 | 2020-06-26 | 沪宝新材料科技（上海）股份有限公司 | Solvent-free double-component finish paint for plastic track |
| CN112934135A (en) * | 2021-01-21 | 2021-06-11 | 西北工业大学 | Preparation method of capsule type stable particles for oil-in-water Pickering emulsion |
| US20230357623A1 (en) * | 2022-04-24 | 2023-11-09 | Southwest Petroleum University | Double-chamber microcapsule for drilling fluid and self-reversing reversible water-in-oil drilling fluid and preparation method thereof |
| US11993743B2 (en) * | 2022-04-24 | 2024-05-28 | Southwest Petroleum University | Double-chamber microcapsule for drilling fluid and self-reversing reversible water-in-oil drilling fluid and preparation method thereof |
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