CN107236073A - A kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber - Google Patents
A kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber Download PDFInfo
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- CN107236073A CN107236073A CN201710473306.2A CN201710473306A CN107236073A CN 107236073 A CN107236073 A CN 107236073A CN 201710473306 A CN201710473306 A CN 201710473306A CN 107236073 A CN107236073 A CN 107236073A
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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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
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Abstract
The present invention provides a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber, comprises the following steps：2 t-butoxycarbonyl amino ethanol, triethylamine and dichloromethane are added in round-bottomed flask, stirred, acryloyl chloride is added dropwise, at room temperature, continue to stir, filtering, recrystallized in the in the mixed solvent of ethyl acetate and n-hexane, obtain 2 t-butoxycarbonyl amino ethyl acrylates；Monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion, 2 t-butoxycarbonyl amino acrylate, chain extender, pH adjusting agent and deionized water are added into pre-emulsion, it is well mixed, nitrogen is passed through, is mixed with after, add initiator, after reaction completely, cooling discharge adjusts pH value to alkalescent at 30 40 DEG C with ammoniacal liquor, take out, obtain antibacterial super branched polyacrylate optical liquid rubber.Liquid glue water-tolerant prepared by the present invention, viscosity is small, and heat endurance is good, and also with antibiotic property, practicality is good.
Description
Technical field
The invention belongs to hyperbranched curing materials technical field, and in particular to a kind of antibacterial super branched polyacrylate optics
The preparation method of liquid glue.
Background technology
Dissaving polymer is similar dendritic, and highly branched three dimensional type is presented in the molecule of dissaving polymer
Vertical substance, intramolecule contains not to tangle mutually between substantial amounts of short-chain branch structure, molecule, and molecular weight it is identical when,
Dissaving polymer has lower viscosity, the end of dissaving polymer contain it is substantial amounts of may modify functional group, can be used to make
Other standby a variety of dissaving polymers, can also introduce some functions on the group contained by dissaving polymer end
Group, such as carboxyl functional group, epoxy-functional, chain alkyl or double-strand functional group, and the synthetic method of dissaving polymer
Simply, multiple fields are applicable to.
Optical transparent adhesive is a kind of product based on the professional adhesive of height, and it has excellent optical property, well
Adhesive property, and the features such as lasting ageing-resistant performance, instead of traditional bonding way, be widely used in intelligence
The consumer-elcetronics devices such as mobile phone, tablet personal computer, touch control display and electronic reader, to strengthen U.S. of the vision of user, equipment
Sense and outward appearance, while strengthening the bonding of touch sensing.At present, optics typically uses propylene with the photosensitive resin of photocuring optical cement
Sour cruel resin, can shorten time rapid link, with good mechanical performance, chemical stability and weatherability etc..
A kind of synthesis side of the solid hyperbranched fluorine-contaninig polyacrylate oligomer of light disclosed in Chinese patent CN105175745A
Method, with phthalic anhydride and epoxy butanol ring-opening polymerization production hyper-branched polyester, by hyper-branched polyester and fluorine-containing epoxy
The solid hyperbranched fluorine-contaninig polyacrylate oligomer of acrylate reactions production cationic photopolymerization, obtains that curing rate is fast, film forming is shunk
Rate is low, can improve water proofing property, the adhesiveness of photocureable coating.From above-mentioned prior art, by UV-curing technology, over-expense
Fluidized polymer, the advantage of acrylic resin are combined, and have the advantages that curing rate is fast, it is small to apply the good, environmental pollution of membranous type energy.But
It is that current hyperbranched propenoic acid resin is still immature in UV-curing technology, molecular structure and active group can not regulate and control, right
The combination property influence of resin is very big.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation of antibacterial super branched polyacrylate optical liquid rubber
Method, the hyperbranched antimicrobial acrylic amino ethyl ester surface of long-chain is covered into acrylic resin again has the polyacrylate of preparation
Hyperbranched characteristic, the characteristic with acrylic acid, polypropylene is solidified viscosity and water resistance of liquid glue etc. is also improved.
In order to solve the above technical problems, the technical scheme is that：
A kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber, comprises the following steps：
(1) 2- t-butoxycarbonyl aminos-ethanol, triethylamine and dichloromethane is added in round-bottomed flask, stirred,
Acryloyl chloride is added dropwise, at room temperature, continues to stir, filtering, recrystallizes, obtain in the in the mixed solvent of ethyl acetate and n-hexane
2- t-butoxycarbonyl aminos-ethyl acrylate；
(2) monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion,
The 2- t-butoxycarbonyl aminos that into pre-emulsion prepared by addition step (1)-acrylate, chain extender, pH adjusting agent and deionization
Water, is well mixed, and is passed through nitrogen, mixes with after, adds initiator, after reaction completely, cooling discharge is used at 30-40 DEG C
Ammoniacal liquor adjusts pH value to alkalescent, takes out, obtains antibacterial super branched polyacrylate optical liquid rubber.
As the preferred of above-mentioned technical proposal, in the step (1), 2- t-butoxycarbonyl aminos-ethanol, triethylamine, two
The material ratio of chloromethanes and acryloyl chloride is 20-25g:15-20g：70-80ml：13-15g.
As the preferred of above-mentioned technical proposal, in the step (1), the time of dropwise addition is 1-1.5h.
As the preferred of above-mentioned technical proposal, in the step (1), distilled water washing and filtering is filtered into 3 times, anhydrous slufuric acid
Sodium is filtered 1 time.
As the preferred of above-mentioned technical proposal, in the step (1), the volume of in the mixed solvent ethyl acetate and n-hexane
Than for 4:1.
As the preferred of above-mentioned technical proposal, in the step (2), chain extender is APS.
As the preferred of above-mentioned technical proposal, in the step (2), initiator is ATRP initiators.
As the preferred of above-mentioned technical proposal, in the step (2), pH adjusting agent is sodium acid carbonate.
As the preferred of above-mentioned technical proposal, in the step (2), the mass fraction of monomer butyl acrylate in pre-emulsion
For 8-12%, the mass fraction of monomeric acrylic is 15-20%, and emulsifying agent SDS mass fraction is 3-7%.
As the preferred of above-mentioned technical proposal, in the step (2), pre-emulsion and 2- t-butoxycarbonyl aminos-acrylic acid
The mass ratio of ester and chain extender is 4-6:1:0.3-0.5.
Compared with prior art, the invention has the advantages that：
Antibacterial super branched polyacrylate optical liquid rubber prepared by the present invention is by the hyperbranched antimicrobial acrylic amino of long-chain
Ethyl ester surface covers acrylic resin again, and the wherein hyperbranched antimicrobial acrylic amino ethyl ester of long-chain has the property of similar antibacterial peptide,
There is cationic and amphipathic simultaneously, therefore with good antibacterial activity, and on its surface, grafted polyacrylic acid is steady again
Determine the performance of liquid curing glue, make the viscosity reduction of the liquid curing glue of preparation, with good transparency and stability, and into
Film is fast, good fluidity, the smooth gloss of glued membrane of preparation, with stronger toughness and hardness.
Embodiment
Describe the present invention in detail below in conjunction with specific embodiment, herein illustrative examples and explanation of the invention
For explaining the present invention, but it is not as a limitation of the invention.
Embodiment 1：
(1) dichloromethane of 20g 2- t-butoxycarbonyl aminos-ethanol, 15g triethylamine and 70ml is added to round bottom
In flask, stir, 13g acryloyl chloride 1h is added dropwise, at room temperature, continue to stir, distilled water washing and filtering 3 times is anhydrous
Filtered over sodium sulfate 1 time, is 4 in ethyl acetate and n-hexane volume ratio:1 in the mixed solvent recrystallization, obtains 2- tertiary butyloxycarbonyls
Base amino-acrylonitrile acetoacetic ester.
(2) monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion,
The mass fraction of monomer butyl acrylate is 8% wherein in pre-emulsion, and the mass fraction of monomeric acrylic is 15%, emulsifying agent
SDS mass fraction is 3%, then according to pre-emulsion and the mass ratio of 2- t-butoxycarbonyl aminos-acrylate and chain extender
For 4:1:0.3,2- t-butoxycarbonyl aminos-acrylate, chain extender APS, pH adjusting agent sodium acid carbonate are added into pre-emulsion
And deionized water, it is well mixed, is passed through nitrogen, mix with after, adds initiator A TRP, after reaction completely, cooling discharge,
PH value is adjusted to alkalescent with ammoniacal liquor at 30 DEG C, is taken out, is obtained antibacterial super branched polyacrylate optical liquid rubber.
Embodiment 2：
(1) dichloromethane of 25g 2- t-butoxycarbonyl aminos-ethanol, 20g triethylamine and 80ml is added to round bottom
In flask, stir, 15g acryloyl chloride 1.5h is added dropwise, at room temperature, continue to stir, distilled water washing and filtering 3 times, nothing
Aqueous sodium persulfate is filtered 1 time, is 4 in ethyl acetate and n-hexane volume ratio:1 in the mixed solvent recrystallization, obtains the tertiary fourth oxygen of 2-
Carbonylamino-ethyl acrylate.
(2) monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion,
The mass fraction of monomer butyl acrylate is 12% wherein in pre-emulsion, and the mass fraction of monomeric acrylic is 20%, emulsifying agent
SDS mass fraction is 7%, then according to pre-emulsion and the mass ratio of 2- t-butoxycarbonyl aminos-acrylate and chain extender
For 6:1:0.5,2- t-butoxycarbonyl aminos-acrylate, chain extender APS, pH adjusting agent sodium acid carbonate are added into pre-emulsion
And deionized water, it is well mixed, is passed through nitrogen, mix with after, adds initiator A TRP, after reaction completely, cooling discharge,
PH value is adjusted to alkalescent with ammoniacal liquor at 40 DEG C, is taken out, is obtained antibacterial super branched polyacrylate optical liquid rubber.
Embodiment 3：
(1) dichloromethane of 23g 2- t-butoxycarbonyl aminos-ethanol, 16g triethylamine and 75ml is added to round bottom
In flask, stir, 13-15g acryloyl chloride 1h is added dropwise, at room temperature, continue to stir, distilled water washing and filtering 3 times, nothing
Aqueous sodium persulfate is filtered 1 time, is 4 in ethyl acetate and n-hexane volume ratio:1 in the mixed solvent recrystallization, obtains the tertiary fourth oxygen of 2-
Carbonylamino-ethyl acrylate.
(2) monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion,
The mass fraction of monomer butyl acrylate is 10% wherein in pre-emulsion, and the mass fraction of monomeric acrylic is 18%, emulsifying agent
SDS mass fraction is 5%, then according to pre-emulsion and the mass ratio of 2- t-butoxycarbonyl aminos-acrylate and chain extender
For 5:1:0.4,2- t-butoxycarbonyl aminos-acrylate, chain extender APS, pH adjusting agent sodium acid carbonate are added into pre-emulsion
And deionized water, it is well mixed, is passed through nitrogen, mix with after, adds initiator A TRP, after reaction completely, cooling discharge,
PH value is adjusted to alkalescent with ammoniacal liquor at 35 DEG C, is taken out, is obtained antibacterial super branched polyacrylate optical liquid rubber.
Embodiment 4：
(1) dichloromethane of 21g 2- t-butoxycarbonyl aminos-ethanol, 16g triethylamine and 73ml is added to round bottom
In flask, stir, 14g acryloyl chloride 1.5h is added dropwise, at room temperature, continue to stir, distilled water washing and filtering 3 times, nothing
Aqueous sodium persulfate is filtered 1 time, is 4 in ethyl acetate and n-hexane volume ratio:1 in the mixed solvent recrystallization, obtains the tertiary fourth oxygen of 2-
Carbonylamino-ethyl acrylate.
(2) monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion,
The mass fraction of monomer butyl acrylate is 11% wherein in pre-emulsion, and the mass fraction of monomeric acrylic is 18%, emulsifying agent
SDS mass fraction is 4%, then according to pre-emulsion and the mass ratio of 2- t-butoxycarbonyl aminos-acrylate and chain extender
For 6:1:0.3,2- t-butoxycarbonyl aminos-acrylate, chain extender APS, pH adjusting agent sodium acid carbonate are added into pre-emulsion
And deionized water, it is well mixed, is passed through nitrogen, mix with after, adds initiator A TRP, after reaction completely, cooling discharge,
PH value is adjusted to alkalescent with ammoniacal liquor at 40 DEG C, is taken out, is obtained antibacterial super branched polyacrylate optical liquid rubber.
Embodiment 5：
(1) dichloromethane of 24g 2- t-butoxycarbonyl aminos-ethanol, 16g triethylamine and 70-80ml is added to
In round-bottomed flask, stir, 13g acryloyl chloride 1h be added dropwise, at room temperature, continue to stir, distilled water washing and filtering 3 times,
Anhydrous sodium sulfate is filtered 1 time, is 4 in ethyl acetate and n-hexane volume ratio:1 in the mixed solvent recrystallization, obtains the tertiary fourths of 2-
Oxygen carbonyl amino-acrylonitrile acetoacetic ester.
(2) monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion,
The mass fraction of monomer butyl acrylate is 9% wherein in pre-emulsion, and the mass fraction of monomeric acrylic is 17%, emulsifying agent
SDS mass fraction is 5%, then according to pre-emulsion and the mass ratio of 2- t-butoxycarbonyl aminos-acrylate and chain extender
For 4:1:0.4,2- t-butoxycarbonyl aminos-acrylate, chain extender APS, pH adjusting agent sodium acid carbonate are added into pre-emulsion
And deionized water, it is well mixed, is passed through nitrogen, mix with after, adds initiator A TRP, after reaction completely, cooling discharge,
PH value is adjusted to alkalescent with ammoniacal liquor at 35 DEG C, is taken out, is obtained antibacterial super branched polyacrylate optical liquid rubber.
Embodiment 6：
(1) dichloromethane of 20g 2- t-butoxycarbonyl aminos-ethanol, 20g triethylamine and 70-80ml is added to
In round-bottomed flask, stir, 13g acryloyl chloride 1.5h is added dropwise, at room temperature, continue to stir, distilled water washing and filtering 3
Secondary, anhydrous sodium sulfate is filtered 1 time, is 4 in ethyl acetate and n-hexane volume ratio:1 in the mixed solvent recrystallization, obtains uncle 2-
Butoxy carbonyl amino-ethyl acrylate.
(2) monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion,
The mass fraction of monomer butyl acrylate is 8% wherein in pre-emulsion, and the mass fraction of monomeric acrylic is 20%, emulsifying agent
SDS mass fraction is 6%, then according to pre-emulsion and the mass ratio of 2- t-butoxycarbonyl aminos-acrylate and chain extender
For 5:1:0.5,2- t-butoxycarbonyl aminos-acrylate, chain extender APS, pH adjusting agent sodium acid carbonate are added into pre-emulsion
And deionized water, it is well mixed, is passed through nitrogen, mix with after, adds initiator A TRP, after reaction completely, cooling discharge,
PH value is adjusted to alkalescent with ammoniacal liquor at 40 DEG C, is taken out, is obtained antibacterial super branched polyacrylate optical liquid rubber.
After testing, the viscosity of antibacterial super branched polyacrylate optical liquid rubber that prepared by embodiment 1-6, surface tension,
The result of water absorption rate and antibiotic rate is as follows：
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | |
| Viscosity (mPas) | 8.5 | 9.2 | 8.8 | 8.7 | 9.0 | 8.9 |
| Surface tension (mN/m) | 32 | 30 | 31 | 34 | 33 | 32 |
| Water absorption rate (%) | 15 | 18 | 16 | 17 | 16 | 17 |
| Antibiotic rate (%) | 89 | 87 | 90 | 91 | 90 | 89 |
As seen from the above table, the viscosity of antibacterial super branched polyacrylate optical liquid rubber prepared by the present invention is small, surface
Power is good, water-tolerant, also with certain antibiotic property.
The above-described embodiments merely illustrate the principles and effects of the present invention, not for the limitation present invention.It is any ripe
Know the personage of this technology all can carry out modifications and changes under the spirit and scope without prejudice to the present invention to above-described embodiment.Cause
This, those of ordinary skill in the art is complete without departing from disclosed spirit and institute under technological thought such as
Into all equivalent modifications or change, should by the present invention claim be covered.
Claims (10)
1. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber, it is characterised in that comprise the following steps：
(1) 2- t-butoxycarbonyl aminos-ethanol, triethylamine and dichloromethane is added in round-bottomed flask, stirred, is added dropwise
Acryloyl chloride, at room temperature, continues to stir, filtering, is recrystallized in the in the mixed solvent of ethyl acetate and n-hexane, obtain uncle 2-
Butoxy carbonyl amino-ethyl acrylate；
(2) monomer butyl acrylate, monomeric acrylic, emulsifying agent SDS are added to the water progress pre-emulsification formation pre-emulsion, toward in advance
The 2- t-butoxycarbonyl aminos that in emulsion prepared by addition step (1)-acrylate, chain extender, pH adjusting agent and deionized water, is mixed
Close uniform, be passed through nitrogen, mix with after, add initiator, after reaction completely, cooling discharge is adjusted at 30-40 DEG C with ammoniacal liquor
PH value is saved to alkalescent, takes out, obtains antibacterial super branched polyacrylate optical liquid rubber.
2. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (1), 2- t-butoxycarbonyl aminos-ethanol, triethylamine, the material ratio of dichloromethane and acryloyl chloride are
20-25g:15-20g：70-80ml：13-15g.
3. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (1), the time of dropwise addition is 1-1.5h.
4. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (1), distilled water washing and filtering is filtered into 3 times, anhydrous sodium sulfate is filtered 1 time.
5. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (1), the volume ratio of in the mixed solvent ethyl acetate and n-hexane is 4:1.
6. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (2), chain extender is APS.
7. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (2), initiator is ATRP initiators.
8. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (2), pH adjusting agent is sodium acid carbonate.
9. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (2), the mass fraction of monomer butyl acrylate is 8-12%, the quality of monomeric acrylic in pre-emulsion
Fraction is 15-20%, and emulsifying agent SDS mass fraction is 3-7%.
10. a kind of preparation method of antibacterial super branched polyacrylate optical liquid rubber according to claim 1, its feature
It is：In the step (2), the mass ratio of pre-emulsion and 2- t-butoxycarbonyl aminos-acrylate and chain extender is 4-6:1:
0.3-0.5。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329467A (en) * | 2018-02-10 | 2018-07-27 | 中国科学院大学 | A kind of preparation method of novel hyperbranched antibacterial peptide polymer |
| CN115322355A (en) * | 2022-07-28 | 2022-11-11 | 大连理工大学 | Tert-butyloxycarbonyl functionalized carbonate monomer, t-butyloxycarbonyl functionalized polycarbonate and preparation method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565912A (en) * | 2016-11-11 | 2017-04-19 | 广州大学 | Polyquaternium polymer emulsion antibacterial agent, preparation method thereof and application thereof |
-
2017
- 2017-06-21 CN CN201710473306.2A patent/CN107236073A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565912A (en) * | 2016-11-11 | 2017-04-19 | 广州大学 | Polyquaternium polymer emulsion antibacterial agent, preparation method thereof and application thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329467A (en) * | 2018-02-10 | 2018-07-27 | 中国科学院大学 | A kind of preparation method of novel hyperbranched antibacterial peptide polymer |
| CN108329467B (en) * | 2018-02-10 | 2020-09-04 | 中国科学院大学 | Preparation method of hyperbranched antibacterial peptide polymer |
| CN115322355A (en) * | 2022-07-28 | 2022-11-11 | 大连理工大学 | Tert-butyloxycarbonyl functionalized carbonate monomer, t-butyloxycarbonyl functionalized polycarbonate and preparation method |
| CN115322355B (en) * | 2022-07-28 | 2024-03-19 | 大连理工大学 | Boc functionalized carbonate monomer, boc functionalized polycarbonate and preparation method thereof |
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