CN104774295A - Macromolecular adhesive containing dopamine phosphate ester structure as well as preparation method and application of macromolecular adhesive - Google Patents
Macromolecular adhesive containing dopamine phosphate ester structure as well as preparation method and application of macromolecular adhesive Download PDFInfo
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Abstract
The invention discloses a polymer represented by a formula I as well as a preparation method and application of the polymer. In the formula I, the molecular weight is 50000-120000; the ratio of x to y is 1:(0.25-0.75); n is 10-50; n1=2 or 3; R1 is any one selected from the group of C1-C4 alkyl and phenyl; and R2 is anyone selected from the group of groups represented by a formula II and a formula III. The preparation method comprises the step of reacting N-(3-amino alkyl) methacrylamide hydrochloride containing amino, dyhydroxyl substituted ortho aromatic aldehyde, phosphite ester and methylacrylic acid polyethylene glycol single methyl ether in an organic solvent in the presence of triethylamine, an initiator and a chain transfer agent. The macromolecular adhesive prepared by the invention is a water-based adhesive, which is mussel-mimetic and environmentally friendly; the macromolecular adhesive is applied to adhering among a plurality of substrates; adhesion can be realized under a variety of conditions; the macromolecular adhesive has good adhesive power; furthermore, the macromolecular adhesive is simple in preparation method, abundant in raw material source and low in cost; and therefore, the macromolecular adhesive is a potential excellent adhesive material.
Description
Technical field
The invention belongs to adhesive field, be specifically related to a kind of polymer binder containing class DOPA amido phosphate ester structure and preparation method thereof and application.
Background technology
Polymer binder is the macromolecular material with bounding force, relies on the chemical reaction at material itself and interface or Physical interaction to realize solidifying, and identical or different material interface can be connected or fits reach the effect of bonding.Current polymer binder on the market mainly contains epoxy resin, cyanoacrylate, resol class and urea-formaldehyde resin class etc.These polymer binders are industrial production, in use usually need with an organic solvent help to dissolve, and are difficult to meet the environmental health of increasingly stringent and the requirement of environmental protection, and have larger limitation when the fields such as biology and medical treatment use.
Summary of the invention
The object of the present invention is to provide a kind of polymer binder containing class DOPA amido phosphate ester structure and preparation method thereof.
The general structure of the polymer binder containing class DOPA amido phosphate ester structure provided by the present invention is such as formula shown in I:
In described formula I, x:y=1:(0.25-0.75), specifically can be 1:(0.3-0.6); N=10-50, specifically can be n=20-30; n
1=2 or 3; R
1be selected from any one in the alkyl of C1-C4 and phenyl; R
2be selected from any one in group shown in formula II and formula III:
In described formula I, R
3and R
4represent the end group of chain-transfer agent respectively.
The molecular weight of polymkeric substance shown in described formula I is 50000 ~ 120000, specifically can be 70000 ~ 90000.
The preparation method of the polymer binder containing class DOPA amido phosphate ester structure provided by the present invention, comprise the steps: under triethylamine, initiator and chain-transfer agent existent condition, the aromatic aldehyde containing amino N-(3-aminoalkyl group) methacrylamide hydrochloride, dihydroxyl replaces ortho position, phosphorous acid ester and Methylacrylic acid polyethylene glycol single armor ether ester are reacted in organic solvent, the described polymer binder containing class DOPA amido phosphate ester structure can be obtained.
In above-mentioned preparation method, the mol ratio of the described aromatic aldehyde containing amino N-(3-aminoalkyl group) methacrylamide hydrochloride, dihydroxyl replacement ortho position, phosphorous acid ester and Methylacrylic acid polyethylene glycol single armor ether ester is 1:(1.1-1.6): (1.2-1.8): (0.25-0.75).
Described N-(3-aminoalkyl group) methacrylamide hydrochloride containing amino specifically can be any one in N-(3-aminopropyl) methacrylamide hydrochloride and N-(3-amino-ethyl) Methacrylamide hydrochloric acid.
Described phosphorous acid ester is specially any one in dimethylphosphite, diethyl phosphite, phosphorous acid dipropyl, dibutyl phosphite and diphenyl phosphite.
The aromatic aldehyde that described dihydroxyl replaces ortho position specifically can be any one in 3,4-Dihydroxy benzaldehyde and 2,3-Dihydroxy benzaldehyde.
The n value of described Methylacrylic acid polyethylene glycol single armor ether ester is 10-50, specifically can be n=20-30.
Before described reaction is carried out, also comprise the step of inflated with nitrogen deoxygenation in question response solution.
Described reaction is reversible addition chain tra nsfer (RAFT) polyreaction and Kabachinik-Fileds reaction.
The temperature of reaction of described reaction is 50-75 DEG C, is specially 60 DEG C, and the reaction times is 8-16h, is specially 10h.
Described organic solvent is specially the mixed solvent of ethanol and acetonitrile, and wherein, the volume ratio of ethanol and acetonitrile is 1:(0.6-1.2).
The mol ratio of described triethylamine and described N-(3-aminoalkyl group) methacrylamide hydrochloride is (1.1-1.3): 1, is specially 1.2:1.
Described initiator specifically can be 2,2'-Azobis(2,4-dimethylvaleronitrile) and/or Diisopropyl azodicarboxylate, and the add-on of described initiator is the 0.3%-0.5% of described monomer N-(3-aminoalkyl group) methacrylamide hydrochloride quality, is specially 0.4%.
Described chain-transfer agent specifically can be 4-cyano group-4-(ethylenebis dithiocarbamate formyl sulfenyl) valeric acid and/or 4-cyano group-4-(ethylenebis dithiocarbamate formyl sulfenyl) benzyl ethyl ester, the add-on of described chain-transfer agent is the 0.6%-1.0% of described monomer N-(3-aminoalkyl group) methacrylamide hydrochloride quality, is specially 0.8%.
When described N-(3-aminoalkyl group) methacrylamide hydrochloride containing amino is N-(3-aminopropyl) methacrylamide hydrochloride; When described phosphorous acid ester is diethyl phosphite, the aromatic aldehyde that described dihydroxyl replaces ortho position is 3, during 4-Dihydroxy benzaldehyde, described chain-transfer agent is 4-cyano group-4-(ethylenebis dithiocarbamate formyl sulfenyl) valeric acid, and the general structure of the polymer binder containing class DOPA amido phosphate ester structure obtained by described preparation method is such as formula shown in IV:
The molecular weight of polymkeric substance shown in described formula IV is 50000 ~ 120000, specifically can be 70000 ~ 90000.
In described formula IV, x:y=1:(0.25-0.75), specifically can be 1:(0.3-0.6); N=10-50, specifically can be n=20-30.
Chain-transfer agent is generally trithio ester cpds, there are many chain-transfer agents that can select, and consumption is little, such as: when adopting 4-cyano group-4-(ethylenebis dithiocarbamate formyl sulfenyl) valeric acid described in the present invention, the end group of chain-transfer agent is respectively group shown in formula IV (group shown in formula IV is R in described formula I
3and R
4position), and in the present invention, the adhesive function of material does not affect by end group, so can select various chain-transfer agent.
The polymer binder containing class DOPA amido phosphate ester structure that the present invention obtains also belongs to protection scope of the present invention preparing the application in tackiness agent.
Another object of the present invention is to provide a kind of method utilizing the described polymer binder jointing material substrate containing class DOPA amido phosphate ester structure.
Method of the present invention, comprises the steps: that pressing, drying, can bond two sheet material substrates at the two sheet material substrate surface coatings to be bonded aqueous solution containing the polymer binder of class DOPA amido phosphate ester structure.
In aforesaid method, the concentration of the aqueous solution of the described polymer binder containing class DOPA amido phosphate ester structure is 0.1 ~ 2.0g/mL, is preferably 1.0g/mL.
The temperature of described drying is 40 ~ 80 DEG C, and be preferably 60 DEG C, the time is 3 ~ 48h, is preferably 20h.
Described material substrate is any one in metal base, high molecule plastic substrate and biological tissue's substrate.
Described metal base specifically can be any one in aluminium flake, latten(-tin), stainless steel substrates and titanium alloy sheet.
Described high molecule plastic substrate specifically can be any one in epoxy sheet, plastics PP and plastics ABS.
The substrate of described biological tissue specifically can be ox bone sheet.
The present invention adopts one kettle way to prepare the polymer binder containing class DOPA amido phosphate ester structure, react in conjunction with Kabachinik-Fileds the polymerization system that comes from different backgrounds and possess different abilities: by 3 by reversible addition chain tra nsfer (RAFT) polymerization, there is the reversible addition chain transfer polymerization of main chain and the Kabachinik-Fields reaction of side chain in a heated condition in 4-Dihydroxy benzaldehyde and amino monomers simultaneously, the polymer that the polymerization of Bound moisture soluble monomers Methylacrylic acid polyethylene glycol single armor ether ester is formed, the DOPA amidophosphate with mussel biomimetic features plays adhesive effect, it is the bionical and aqueous-based adhesive of environment-friendly and green of a kind of mussel.
The monomer that the method is applied and other raw material are all easy to buy, preparation method is simple, prepared polymer binder good water solubility, simple to operate, during bonding metal substrate, its shearing resistance, at more than 2MPa, also can bond high molecule plastic substrate and biological tissue, as ox bone etc., be applicable to multiple substrate.
In addition, in the present invention, the described polymer binder containing class DOPA amido phosphate ester structure, under oxidation, alkalescence, polyvalent metal ion and small molecules linking agent existent condition, cross-linking density and speed all can increase, and can accelerate binding speed, save the bonding time.As: to as described in class containing DOPA amido phosphate ester structure polymer binder in add account for small molecules linking agent 1,1, the 1-trishydroxymethyl ethyl triacrylate of its quality 10% after, its bonding aluminium alloy cohesive strength rise to 3Mpa from 2Mpa.
Compared with prior art, tackiness agent provided by the present invention has following outstanding feature:
1, the abundant raw material source of preparation needed for polymer binder of the present invention, cheap.
2, the preparation method of polymer binder of the present invention is simple, and processing parameter is easy to control.
3, the good water solubility of polymer binder of the present invention is a kind of water-base macromolecule abhesive agent of environmental protection.
4, polymer binder bonding effect of the present invention is good, and to multiple substrate, can comprise metal base, plastic-substrates and biological tissue as ox bone substrate etc., bond.
5, bond required time and temperature range adjustable, be easy to realize under numerous conditions bonding.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of the polymer binder containing class DOPA amido phosphate ester structure in embodiment 1.
Fig. 2 is the nucleus magnetic hydrogen spectrum phenogram of the polymer binder (formula IV) containing class DOPA amido phosphate ester structure in embodiment 1.
Embodiment
Be described method of the present invention below by specific embodiment, but the present invention is not limited thereto, all any amendments done within the spirit and principles in the present invention, equivalent replacement and improvement etc., all should be included within protection scope of the present invention.
Experimental technique described in following embodiment, if no special instructions, is ordinary method; Described reagent and material, if no special instructions, all can obtain from commercial channels.
Embodiment 1, preparation contain the polymer binder of class DOPA amido phosphate ester structure:
Adopt one kettle way by monomer N-(3-aminopropyl) methacrylamide hydrochloride, 3, 4-Dihydroxy benzaldehyde, diethyl phosphite and Methylacrylic acid polyethylene glycol single armor ether ester (copolymerization monomer) join the mixed solvent of ethanol and acetonitrile (wherein by molar ratio 1:1.2:1.4:0.5, the volume ratio of ethanol and acetonitrile is 1:1) in, and add triethylamine wherein again, the mol ratio making triethylamine and monomer N-(3-aminopropyl) methacrylamide hydrochloride is 1.2:1, the object adding triethylamine be in and monomer with hydrochloride, initiator 2,2'-Azobis(2,4-dimethylvaleronitrile) (quality accounts for 0.4% of monomer N-(3-aminopropyl) methacrylamide hydrochloride quality) and chain-transfer agent 4-cyano group-4-(ethylenebis dithiocarbamate formyl sulfenyl) valeric acid (quality accounts for 0.8% of monomer N-(3-aminopropyl) methacrylamide hydrochloride quality), after inflated with nitrogen deoxygenation, at 60 DEG C, reacting by heating 10 is little complete up to reaction, gained reaction solution will be reacted dialyse in methyl alcohol and (adopt universal regenerated fibre dialysis tubing, molecular weight cut-off 7000), the polymer binder containing class DOPA amido phosphate ester structure can be obtained after drying, its corresponding structural formula is as shown in Fig. 1 (formula IV), wherein, in formula I, x:y=1:0.5, n=21, molecular weight is 75000.The structure confirming prepared polymkeric substance is characterized via nucleus magnetic hydrogen spectrum (as shown in Figure 2).
Embodiment 2, utilization carry out bonding experiment between material substrate containing the polymer binder of class DOPA amido phosphate ester structure:
1) get the polymer binder powder dissolution that obtains in 1.0g embodiment 1 in water, constant volume obtains the polymer binder aqueous solution that 1mL concentration is 1g/mL;
2) respectively get 10 μ L steps 1) in the polymer binder aqueous solution drip respectively in two sheet material substrate surface 1cm × 1cm regions, and leave standstill volatilization a moment;
3) by step 2) in two drip and have the material substrate of the polymer binder aqueous solution to compress, clamp, be placed in 60 DEG C of baking ovens heating 20 hours, taking-up is cooled to room temperature, can by two sheet material substrate adhesive together;
Stretching experiment is carried out to the two sheet material substrates be bonded together:
The shearing resistance of microcomputer manipulation multifunctional digital test machine to jointing material substrate is tested, learn that polymer binder is 3MPa to aluminium flake bond strength, be 2MPa to latten(-tin) bond strength, be 1.5MPa to stainless steel substrates bond strength, to titanium alloy sheet bond strength 1MPa, to epoxy sheet bond strength 1Mpa, to ox bone sheet bond strength 0.5Mpa, to plastics ABS bond strength 0.5Mpa, to plastics PP bond strength 0.5Mpa.
Claims (10)
1. polymkeric substance shown in formula I:
In described formula I, x:y=1:(0.25-0.75); N=10-50; n
1=2 or 3; R
1be selected from any one in the alkyl of C1-C4 and phenyl; R
2be selected from any one in group shown in formula II and formula III,
In described formula I, R
3and R
4represent the end group of chain-transfer agent respectively;
The molecular weight of polymkeric substance shown in described formula I is 50000 ~ 120000.
2. polymkeric substance shown in formula I according to claim 1, is characterized in that: the general structure of polymkeric substance shown in formula I is such as formula shown in IV:
In described formula IV, x:y=1:(0.25-0.75), n=10-50;
The molecular weight of polymkeric substance shown in described formula IV is 50000 ~ 120000.
3. the preparation method of polymkeric substance shown in formula I according to claim 1, comprise the steps: under triethylamine, initiator and chain-transfer agent existent condition, the aromatic aldehyde containing amino N-(3-aminoalkyl group) methacrylamide hydrochloride, dihydroxyl replaces ortho position, phosphorous acid ester and Methylacrylic acid polyethylene glycol single armor ether ester are reacted in organic solvent, namely obtains polymkeric substance shown in formula I.
4. preparation method according to claim 3, is characterized in that: described reaction is the reaction of reversible addition chain transfer polymerization and Kabachinik-Fileds reaction;
The temperature of reaction of described reaction is 50-75 DEG C, and the reaction times is 8-16h;
The mol ratio of the described aromatic aldehyde containing amino N-(3-aminoalkyl group) methacrylamide hydrochloride, dihydroxyl replacement ortho position, phosphorous acid ester and Methylacrylic acid polyethylene glycol single armor ether ester is 1:(1.1-1.6): (1.2-1.8): (0.25-0.75);
Described is any one in N-(3-aminopropyl) methacrylamide hydrochloride and N-(3-amino-ethyl) Methacrylamide hydrochloric acid containing amino N-(3-aminoalkyl group) methacrylamide hydrochloride;
Described phosphorous acid ester is any one in dimethylphosphite, diethyl phosphite, phosphorous acid dipropyl, dibutyl phosphite and diphenyl phosphite;
The aromatic aldehyde that described dihydroxyl replaces ortho position is any one in 3,4-Dihydroxy benzaldehyde and 2,3-Dihydroxy benzaldehyde;
The n value of described Methylacrylic acid polyethylene glycol single armor ether ester is 10-50;
The mol ratio of described triethylamine and described N-(3-aminoalkyl group) methacrylamide hydrochloride is (1.1-1.3): 1;
Described initiator is 2,2'-Azobis(2,4-dimethylvaleronitrile) and/or Diisopropyl azodicarboxylate, and the add-on of described initiator is the 0.3%-0.5% of described monomer N-(3-aminoalkyl group) methacrylamide hydrochloride quality;
Described chain-transfer agent is 4-cyano group-4-(ethylenebis dithiocarbamate formyl sulfenyl) valeric acid and/or 4-cyano group-4-(ethylenebis dithiocarbamate formyl sulfenyl) benzyl ethyl ester, and the add-on of described chain-transfer agent is the 0.6%-1.0% of described monomer N-(3-aminoalkyl group) methacrylamide hydrochloride quality.
5. the preparation method according to claim 3 or 4, is characterized in that: before described reaction is carried out, and also comprises the step of inflated with nitrogen deoxygenation in question response solution;
Described organic solvent is the mixed solvent of ethanol and acetonitrile, and wherein, the volume ratio of ethanol and acetonitrile is 1:(0.6-1.2).
6. the polymkeric substance described in claim 1 or 2 is preparing the application in tackiness agent.
7. utilize a method for the polymeric binder material substrate described in claim 1 or 2, comprise the steps: that the two sheet material substrate surfaces to be bonded apply the aqueous solution of polymkeric substance shown in described formula I, pressing, drying, can bond two sheet material substrates.
8. method according to claim 7, is characterized in that: the concentration of the aqueous solution of polymkeric substance shown in described formula I is 0.1 ~ 2.0g/mL;
The temperature of described drying is 40 ~ 80 DEG C, and the time is 3 ~ 48h.
9. the method according to claim 7 or 8, is characterized in that: described material substrate is any one in metal base, high molecule plastic substrate and biological tissue's substrate.
10. method according to claim 9, is characterized in that: described metal base is any one in aluminium flake, latten(-tin), stainless steel substrates and titanium alloy sheet;
Described high molecule plastic substrate is any one in epoxy sheet, plastics PP and plastics ABS;
The substrate of described biological tissue is any one in ox bone sheet and pig osteocomma.
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| CN109225783A (en) * | 2018-09-03 | 2019-01-18 | 四川汇利实业有限公司 | A kind of production technology of packaging composite film |
| CN109762492A (en) * | 2018-12-29 | 2019-05-17 | 北京东方雨虹防水技术股份有限公司 | The bionical mussel adhesive of one pack system mutually separates the method for realizing wet face and underwater construction with utilization |
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| CN114149752A (en) * | 2020-09-07 | 2022-03-08 | 中国科学院理化技术研究所 | Adhesive and application thereof |
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| CN110573544A (en) * | 2017-04-28 | 2019-12-13 | 罗伯特·博世有限公司 | Composite binder for lithium ion battery and preparation method thereof |
| CN110573544B (en) * | 2017-04-28 | 2022-08-16 | 罗伯特·博世有限公司 | Composite binder for lithium ion battery and preparation method thereof |
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| US11466112B2 (en) | 2017-12-07 | 2022-10-11 | Lg Chem, Ltd. | Carboxylic acid modified nitrile based copolymer latex, method for preparing the copolymer latex, latex composition for dip-forming comprising the copolymer latex and article formed by the composition |
| CN108371728A (en) * | 2018-03-09 | 2018-08-07 | 西南交通大学 | A kind of imitative mussel for tissue repair contacts the preparation method of anti-bacterial hydrogel |
| CN108371728B (en) * | 2018-03-09 | 2020-12-18 | 西南交通大学 | Preparation method of mussel-like contact antibacterial hydrogel for tissue repair |
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| CN109225783B (en) * | 2018-09-03 | 2021-02-19 | 四川汇利实业有限公司 | Production process of packaging composite film |
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| CN112409519A (en) * | 2020-12-07 | 2021-02-26 | 清华大学 | Novel alpha-aminophosphonate polymer material with non-traditional fluorescent property |
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