CN108003317A - A kind of silicone elastomer and its preparation method and application - Google Patents
A kind of silicone elastomer and its preparation method and application Download PDFInfo
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- CN108003317A CN108003317A CN201711406634.7A CN201711406634A CN108003317A CN 108003317 A CN108003317 A CN 108003317A CN 201711406634 A CN201711406634 A CN 201711406634A CN 108003317 A CN108003317 A CN 108003317A
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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
- C08G18/28—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
- C08G18/61—Polysiloxanes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3804—Polyhydroxy compounds
- C08G18/3806—Polyhydroxy compounds having chlorine and/or bromine atoms
- C08G18/3808—Polyhydroxy compounds having chlorine and/or bromine atoms having chlorine atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
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- Materials For Medical Uses (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention relates to new material technology field, more particularly to a kind of silicone elastomer and its preparation method and application, by amino or hydroxy-end capped dimethyl silicone polymer, diisocyanate, phenolic compound, crosslinking agent dissolving in organic solvent, add proper catalyst, after reaction, prepolymer is poured into Teflon mould, is heating and curing, except obtaining a kind of new polysiloxanes elastomer after solvent.The silicone elastomer mechanical strength of the present invention is good, has thermoplasticity good, can process again, also with self-repair function, applied to fields such as flexible electronic, 3D printing, bio-medicals.
Description
Technical field
The present invention relates to new material technology field, and in particular to a kind of silicone elastomer and preparation method thereof and should
With.
Background technology
Polysiloxane backbone is alternately made of silicon, oxygen atom, organic group is directly connected on silicon atom, it is with inorganic
With the characteristic of organic polymer, such as high-low temperature resistant, weather-resistant, electric insulation, resistance to ozone, hydrophobic, gas-premeable is good
And nontoxic, biologically inert etc..It is widely used in the fields such as electric, building, automobile, weaving, medical treatment.Polysiloxane molecule
Chain is submissive and intermolecular force is low, therefore is used usually in the form of cross-linked elastomer, traditional silicone elastomer face
Face the problem identical with all thermosets：(1) after there is breakage during processing and forming and use in material, Wu Fashi
Existing self-regeneration is so as to extend the service life of material；(2) it is difficult to recycling processing after material scrap to recycle, causes greatly to damage
Become estranged the wasting of resources.
At present, the selfreparing silicone elastomer on can be processed containing reversible dynamic key again has been reported.Harreld etc.
People discloses a kind of silicone elastomer based on hydrogen bond crosslinks in patent US 6783709B2.They introduce polypeptide poly-
Siloxane chain, cross linking polysiloxane elastomer is prepared for using the characteristics of can forming hydrogen bond between polypeptide.The elastomer can
Selfreparing and process again at ambient temperature, however, since hydrogen bond action intensity is weak, the poor mechanical property of material.Odriozola
Ibon et al. discloses a kind of selfreparing silicone elastomer based on boric acid ester bond in patent WO 2013127989A1.
The material is combined by the crosslinked polysiloxanes of boric acid ester bond and the thermoplastic, polymeric materials such as pitch, PP, PE, SBS.But
The heavy processing temperature of material is higher (~200 DEG C), at the same can not judgement material self-healing properties quality.Except hydrogen bond and boric acid
Ester bond, Diels-Alder keys are also a kind of effective reversible covalent bonds, the reaction have concurrently stereoselectivity, stereocpecificity and
Regioselectivity, and yield is high, and the irreversible temperature of reaction can be adjusted by varying the structure of close diene and diene, so as to
The processing temperature of controlled material, wherein furans-maleimide amine system are studied the widest since its reaction condition is most gentle
It is general.Xia Hesheng of Sichuan University et al. reports a kind of Diels-Alder keys crosslinked silicone elastomer (Zhao, J.；
Xu,R.；Luo,G.X.；Wu,W.；Xia,H.S.A self-healing,re-moldable and biocompatible
crosslinked polysiloxane elastomer.J.Mater.Chem.B,2016,4,982-989.).They close first
The siloxanes small molecule crosslinking agent blocked into Maleimide-modified polysiloxane copolymer and furans, both pass through
Diels-Alder reacts to form the crosslinked silicone elastomer of DA keys.Material has excellent processing again and self-healing properties,
But the mechanical property of material is poor, and the mechanical property and self-healing properties of material can not be improved at the same time.
Polyurethane elastomer (Polyurethane elastomer abbreviation PU) is to contain carbamate (- NH- in molecule
COO-) the general designation of the polymeric material of structure.Formed by oligomer polyol and polyisocyanate polyaddition.Its MOLECULE DESIGN
Ability is strong, according to the difference of raw material and formula, can obtain the polyurethane elastomer material of different performance.All polyurethane
Regard the block copolymer that rigid chain segment and soft segment are alternately formed by connecting as, due to the incompatibility of two kinds of segments, polyurethane
It is in micro phase separation structure on microcosmic.The unique texture of this microphase-separated of polyurethane elastomer, which imparts material, has other very
Excellent comprehensive performance not available for more commercialization rubber and plastics：High intensity and high elongation rate, good wearability；Great Rong
The load support of amount, strong damping impact resistance, oil resistant, solvent resistance etc..
The content of the invention
It is an object of the invention to the THERMALLY REVERSIBLE COVALENT silicone elastomer for existing hydrogen bonds or boric acid ester bond
Poor mechanical property, weight processing temperature are high, and Diels-Alder keys cross linking polysiloxane mechanics of elastic bodies performance and self-repairability
The problem of be able to not obtaining improving at the same time, there is provided a kind of silicone elastomer and its preparation method and application, phenols amino first
Acid esters key is reacted to obtain by phenol with isocyanates, is a kind of new thermal response-type dynamic key, can make material can be certainly at 90 DEG C
Repair, and benzene ring structure can also improve the mechanical strength of material, and mechanics of elastic bodies excellent performance of the present invention, transparency is high,
Weight processing performance is good, and self-repair efficiency is high, and reparation temperature is relatively low, and preparation process is simple, is of relatively low cost.
The purpose of the present invention is what is be achieved through the following technical solutions：
A kind of silicone elastomer, including following raw material is in terms of the amount number of material：
Further, the amino or hydroxy-end capped dimethyl silicone polymer for molecular weight 300~50000 amino or
At least one of hydroxyl endblocked polydimethylsiloxane.
Further, the diisocyanate is toluene di-isocyanate(TDI), methyl diphenylene diisocyanate, two methylene of benzene
At least one of group diisocyanate, hexamethylene diisocyanate, dicyclohexyl methyl hydride diisocyanate.
Further, the phenolic compound is saligenin, p-Hydroxybenzylalcohol, hydroquinone, 1,3- naphthalenediols, 4-
The bromo- 1,3- benzenediols of bromo- 1,2- benzenediols, 5-, the fluoro- 1,2- benzenediols of 3,6- bis-, 4,5- dinitro -1,2- benzenediols, 2,2-
Two (4- hydroxy phenyls) propane (bisphenol-A), 4,4' dihydroxydiphenyl sulfone (bisphenol S), tetrachlorobisphenol A, tetrabromobisphenol A, Bisphenol F,
At least one of '-biphenyl diphenol.
Further, the crosslinking agent be hexamethylene diisocyanate trimer, it is toluene diisocyanate trimer, different
At least one of isophorone diisocyanate tripolymer.
Further, the solvent is toluene, in dimethylbenzene, dichloromethane, chloroform, tetrahydrofuran, Isosorbide-5-Nitrae-dioxane
At least one.
A kind of preparation method of such as above-mentioned silicone elastomer, comprises the following steps：By dissolution of raw material in a solvent
To reaction solution, 1 drop N, N- dimethyl cyclohexylamine catalysts, when stirring reaction 2~10 is small at room temperature are added；Added for 1 drop February
Dilaurylate (DBTDL) catalyst, room temperature the reaction was continued 2~10 it is small when；After reaction, prepolymer is poured into polytetrafluoro
In ethene mould, when cold curing 10~96 is small, place into 60 DEG C of baking ovens except solvent and continue curing 10~96 it is small when, solvent
Steam is recycled by solvent recovery machine, is finally removed from the molds to obtain the polysiloxanes bullet of the amino-formate bond of dynamic containing phenols
Property body.
A kind of application of such as above-mentioned silicone elastomer, it is characterised in that be applied to 3D as consumptive material or intermediate materials
Printing or flexible electrode base material field.
The beneficial effects of the invention are as follows：
(1) present invention uses bisphenol compound in the feed, makes to carry phenyl ring on molecular weight main chain, can significantly improve
The mechanical strength of material, in 200% deformation, tensile strength is i.e. up to 2MPa；
(2) the bisphenol type dynamic amino-formate bond in the silicone elastomer of the amino-formate bond of the invention containing phenols
It is a kind of thermal reversion chemical bond, can be broken at high temperature, reducing temperature can regenerates again, this characteristic causes prepared gather
Silicone elastomer not only had the performance processed again, but also can realize and review one's lessons by oneself in the case of without any additional renovation agent or catalyst
It is multiple；
(3) polysiloxanes-urethane elastomers of the amino-formate bond containing phenols of the invention have hot-workability
Can, and material still keeps transparent after processing, can be applied to the technologies such as the fields such as flexible electronic, 3D printing, bio-medical
Field；
(4) raw material that the present invention uses is easy to get, and building-up process is simply easy without any specific condition or equipment, synthesis technique
Control, yield are high.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of the silicone elastomer of the amino-formate bond of dynamic containing phenols prepared by test example 1；
Fig. 2 is the silicone elastomer print figure of the amino-formate bond of dynamic containing phenols in test example 2；
Fig. 3 is the master drawing after the silicone elastomer print of the amino-formate bond of dynamic containing phenols in test example 2 shreds；
Fig. 4 is the master drawing silicone elastomer of the amino-formate bond of dynamic containing phenols in test example 2 is processed again after；
Sample should Fig. 5 processes for the silicone elastomer of the amino-formate bond of dynamic containing phenols in test example 2 again after
Force-strain curve figure；
Fig. 6 is the original sample of the silicone elastomer of the amino-formate bond of dynamic containing phenols prepared by test example 3 and repaiies
The load-deformation curve comparison diagram of duplicate sample.
Embodiment
Technical scheme, but the protection of the present invention are described in further detail with reference to specific embodiments and the drawings
Scope is not limited to as described below.
Embodiment
A kind of silicone elastomer：
By following raw material, dissolving obtains reaction solution in terms of the amount number of material：2~12 parts of crosslinking agents, 18~31 parts of amino or
Hydroxy-end capped dimethyl silicone polymer, 10~41 parts of diisocyanate, 5~35 parts of phenolic compounds, 20~50 parts of solvents, add
Enter 1 drop N, N- dimethyl cyclohexylamine catalyst, when stirring reaction 5 is small at room temperature；Add 1 drop dibutyl tin laurate
(DBTDL) catalyst, room temperature the reaction was continued 5 it is small when；After reaction, prepolymer is poured into Teflon mould, room temperature
Cure 10~96 it is small when, place into 60 DEG C of baking ovens except solvent, continue curing 10~96 it is small when, be finally removed from the molds to obtain
The silicone elastomer of the amino-formate bond of dynamic containing phenols.
Preferably, the amino or amino or hydroxyl that hydroxy-end capped dimethyl silicone polymer is molecular weight 300~50000
Base blocks at least one of dimethyl silicone polymer；The diisocyanate is toluene di-isocyanate(TDI), diphenyl methane two is different
In cyanate, benzene dimethylene diisocyanate, hexamethylene diisocyanate, dicyclohexyl methyl hydride diisocyanate at least
It is a kind of；The phenolic compound for saligenin, p-Hydroxybenzylalcohol, hydroquinone, 1,3- naphthalenediols, the bromo- 1,2- benzenediols of 4-,
The bromo- 1,3- benzenediols of 5-, the fluoro- 1,2- benzenediols of 3,6- bis-, 4,5- dinitro -1,2- benzenediols, 2,2- bis- (4- hydroxy phenyls)
In propane (bisphenol-A), 4,4' dihydroxydiphenyl sulfone (bisphenol S), tetrachlorobisphenol A, tetrabromobisphenol A, Bisphenol F, '-biphenyl diphenol extremely
Few one kind；The crosslinking agent is hexamethylene diisocyanate trimer, toluene diisocyanate trimer, isophorone two are different
At least one of cyanate tripolymer；The solvent is toluene, dimethylbenzene, dichloromethane, chloroform, tetrahydrofuran, 1,4- bis-
At least one of six ring of oxygen.
In a preferred embodiment, the amino or hydroxy-end capped dimethyl silicone polymer be molecular weight be 900,
1000th, at least one of 3000,5000 or 30000 amino or hydroxyl endblocked polydimethylsiloxane.
Test example 1
Dimethyl silicone polymer DMS-A21,0.532g isophorone diisocyanate of 9g aminopropyls end-blocking, 0.28g tetra-
Chlorine bisphenol-A and 0.2g hexamethylene diisocyanate trimers are dissolved in 20ml tetrahydrofurans, add 1 drop N, N- diformazan basic rings
Hexylamine, be stirred at room temperature reaction 3 it is small when；Add 1 drop dibutyl tin laurate (DBTDL) catalyst, that the reaction was continued is 1 small for room temperature
When；After reaction, prepolymer is poured into Teflon mould, when cold curing 24 is small, places into 60 DEG C of baking oven relayings
It is continuous cure 48 it is small when, after be removed from the molds to obtain the silicone elastomer of the amino-formate bond of dynamic containing bisphenol type, to
The elastomer arrived carries out infrared spectrum detection, and testing result is as shown in Figure 1.
Test example 2
The heavy processing performance displaying of the silicone elastomer of the amino-formate bond of dynamic containing bisphenol type：By in test example 1
The elastomer print (as shown in Figure 2) of preparation shreds into fritter (as shown in Figure 3), these, which are then shredded into fritter, is molded into
Type, condition of molding：110 DEG C, keep 20min under the conditions of 10MPa, then place 10h, result of the test such as Fig. 4 and Fig. 5 institutes at 60 DEG C
Show, Fig. 5 attach most importance to processing after sample stress-strain curve.
Test example 3
The self-healing properties displaying of the silicone elastomer of the amino-formate bond of dynamic containing bisphenol type：By in test example 1
Prepare elastomer and be cut into dumbbell shape batten, the thin neck of batten is cut off with blade, and then both ends of the surface, which fit together, rapidly is placed on
In 90 DEG C of baking ovens 6 it is small when, be then placed within 12h in 60 DEG C of baking ovens, result of the test as shown in fig. 6, Fig. 6 for original sample and repair sample
Load-deformation curve comparison diagram.
The above is only the preferred embodiment of the present invention, it should be understood that the present invention is not limited to described herein
Form, is not to be taken as the exclusion to other embodiment, and can be used for various other combinations, modification and environment, and can be at this
In the text contemplated scope, it is modified by the technology or knowledge of above-mentioned teaching or association area.And those skilled in the art institute into
Capable modifications and changes do not depart from the spirit and scope of the present invention, then all should be in the protection domain of appended claims of the present invention
It is interior.
Claims (8)
1. a kind of silicone elastomer, it is characterised in that including following raw material in terms of the amount number of material：
。
2. a kind of silicone elastomer according to claim 1, it is characterised in that the amino is hydroxy-end capped poly-
Dimethyl siloxane is the amino of molecular weight 300~50000 or at least one of hydroxyl endblocked polydimethylsiloxane.
3. a kind of silicone elastomer according to claim 1, it is characterised in that the diisocyanate is toluene two
Isocyanates, methyl diphenylene diisocyanate, benzene dimethylene diisocyanate, hexamethylene diisocyanate, two hexamethylenes
At least one of dicyclohexylmethane diisocyanate.
4. a kind of silicone elastomer according to claim 1, it is characterised in that the phenolic compound is bigcatkin willow
The bromo- 1,2- benzenediols of alcohol, p-Hydroxybenzylalcohol, hydroquinone, 1,3- naphthalenediols, 4-, the bromo- 1,3- benzenediols of 5-, 3,6- bis- are fluoro-
1,2- benzenediols, 4,5- dinitro -1,2- benzenediols, 2,2- bis- (4- hydroxy phenyls) propane (bisphenol-A), 4,4'- dihydroxy two
At least one of benzene sulfone (bisphenol S), tetrachlorobisphenol A, tetrabromobisphenol A, Bisphenol F, '-biphenyl diphenol.
5. a kind of silicone elastomer according to claim 1, it is characterised in that the crosslinking agent is hexa-methylene two
At least one of isocyanate trimer, toluene diisocyanate trimer, isophorone diisocyanate trimer.
A kind of 6. silicone elastomer according to claim 1, it is characterised in that the solvent for toluene, dimethylbenzene,
At least one of dichloromethane, chloroform, tetrahydrofuran, 1,4- dioxane.
A kind of 7. preparation method of the silicone elastomer as described in any one such as claim 1~6, it is characterised in that including
Following steps：Dissolution of raw material is obtained into reaction solution in a solvent, adds appropriate N, N- dimethyl cyclohexylamine catalysts, are stirred at room temperature
Mix reaction 2~10 it is small when；Add a drop dibutyltin dilaurate catalyst, room temperature the reaction was continued 2~10 it is small when；Reaction knot
Shu Hou, prepolymer is poured into Teflon mould, when cold curing 10~96 is small, is placed into 60 DEG C of baking ovens and is removed solvent simultaneously
Continue curing 10~96 it is small when, solvent vapo(u)r is recycled by solvent recovery machine, is finally removed from the molds to obtain containing phenols dynamic
The silicone elastomer of amino-formate bond.
8. a kind of application of the silicone elastomer as described in any one such as claim 1~6, it is characterised in that the material should
For FIELD OF THE INVENTIONThes such as flexible electronic, 3D printing, bio-medicals.
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| CN109161202A (en) * | 2018-08-09 | 2019-01-08 | 中国科学院深圳先进技术研究院 | A kind of elastic composite and preparation method thereof and self-repair method |
| CN110294836A (en) * | 2019-06-24 | 2019-10-01 | 西安交通大学 | One kind can selfreparing shape-memory material and preparation method thereof and recovery method |
| CN110305293A (en) * | 2019-07-11 | 2019-10-08 | 清华大学 | Selfreparing thermal reversion cross-linked polyurethane containing bis-phenol and preparation method thereof |
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