CN112778145A - Long-acting antibacterial PAE resin, preparation method thereof and coating composition - Google Patents
Long-acting antibacterial PAE resin, preparation method thereof and coating composition Download PDFInfo
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- CN112778145A CN112778145A CN202011628066.7A CN202011628066A CN112778145A CN 112778145 A CN112778145 A CN 112778145A CN 202011628066 A CN202011628066 A CN 202011628066A CN 112778145 A CN112778145 A CN 112778145A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
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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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/02—Polyureas
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0806—Silver
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
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- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
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Abstract
The invention discloses a long-acting bacteriostatic PAE resin, a preparation method thereof and a coating composition. The high branching property of the resin enables the resin to have better fluidity, and the resin has sufficient operation time during construction of the polyurea double-component terrace through adjusting the proportion; meanwhile, the dendritic macromolecular structure contains a large number of cavities, so that the stable and dispersed nano-silver antibacterial floor has a good effect, and the antibacterial effect cannot be remarkably reduced along with long-time use or aging of the floor.
Description
Technical Field
The invention relates to the field of polymers and high molecular coatings, in particular to a long-acting antibacterial PAE resin, a preparation method thereof and a coating composition.
Background
The PAE polyurea material has excellent elasticity, water resistance, skid resistance, wear resistance and other performances, is an excellent coating and bonding material, and has wide application in floor coatings.
Polyaspartic Acid Ester (PAE) is a novel sterically hindered amine structure developed in recent years, and the chemical structural formula of the Polyaspartic Acid Ester is shown as a formula I. In the prior art, the strength, uniformity, elasticity, wear resistance and yellowing resistance of the PAE polyurea resin are improved, but the antibacterial/antibacterial performance of the PAE polyurea resin and a floor coating composition thereof is not deeply researched, so that the application of the PAE polyurea resin in the field of medical treatment and health is limited. Most of the current coatings adopt fillers with bacteriostatic efficacy added in coating compositions to realize bacteriostatic effects, and the fillers are precipitated and aged after long-term use, so that the bacteriostatic effects disappear gradually.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide a quaternary ammonium salt modified long-acting bacteriostatic PAE resin with long-acting bacteriostatic effect; it is still another object of the present invention to provide a method for preparing the aforementioned PAE resin, and a floor coating composition prepared therefrom.
The technical scheme is as follows: in order to achieve the above object, the preparation method of the long-acting antibacterial PAE resin comprises the following steps: adding a xylene solution containing dimethyl maleate and hydroxyl quaternary ammonium salt into a reaction container, adding a catalyst to perform ester exchange reaction, and separating the solvent to obtain maleic acid ester quaternary ammonium salt; adding aliphatic diamine into a reaction container, dropwise adding quaternary ammonium salt of maleate under the condition of introducing nitrogen, and preserving heat after the dropwise adding end point to obtain the long-acting antibacterial PAE resin.
The synthesis of the hydroxy quaternary ammonium salts described in the present invention can be obtained by synthesis starting from tertiary amines (e.g., N' -dimethylethanolamine) and quaternizing them with halohydrins, which are well known in the art. As a preferred embodiment of the invention, the ammonium ions of the hydroxyl quaternary ammonium salt are connected with the same or different C1-C3 linear alkyl, and the anion is selected from F-、Cl-、Br-、I-Any one of the above.
More preferably, the hydroxyl quaternary ammonium salt is monohydroxy substituted quaternary ammonium salt, and the anion is preferably chloride ion or bromide ion, and as a most preferred embodiment, the hydroxyl quaternary ammonium salt is selected from any one of hydroxymethyl trimethyl ammonium chloride, 2-hydroxypropyl trimethyl ammonium chloride and hydroxyethyl trimethyl ammonium chloride.
Further, the catalyst is selected from any one or combination of more of sodium methoxide, triethylamine and p-toluenesulfonic acid, and the input amount of the catalyst is 0.01-0.1 wt%. Preferably, the catalyst is p-toluenesulfonic acid, and the input amount of the catalyst is 0.05 wt%.
Further, the ester exchange reaction is carried out for 4-8 hours at 120-140 ℃, and the molar ratio of the dimethyl maleate to the hydroxyl quaternary ammonium salt is 1 (2-2.5). Considering that the hydroxy quaternary ammonium salt completely replaces methyl of dimethyl maleate, the hydroxy quaternary ammonium salt is ensured to be in proper excess, if the hydroxy quaternary ammonium salt is obviously in excess, the proportion of secondary amine and hydroxyl in the quaternary ammonium salt modified PAE dendritic resin is reduced, and the product performance is influenced, and as a preferred scheme of the invention, the molar ratio is 1: 2.1.
The aliphatic diamine is C2-C14 saturated alkyl diamine. Preferably, a symmetrical alkyldiamine is used, more preferably a high molecular weight cyclohexyl group-containing diamine, such as any one of 4, 4' -diaminodicyclohexylmethane, 1, 6-hexamethylenediamine, isophoronediamine, m-xylylenediamine.
Further, the molar ratio of the aliphatic diamine to the quaternary ammonium maleate is 1 (2-2.5). The excessive quaternary ammonium maleate salt ensures that the primary amine is completely converted into the secondary amine so as not to cause the resin curing speed to be too fast and not to fully use the operation time. As a preferred embodiment of the present invention, the molar ratio is 1:2.1
And (3) dropwise adding quaternary ammonium maleate until the reaction end, heating to 60-65 ℃, and keeping the temperature for 24-36 hours.
The invention also provides a long-acting antibacterial PAE resin which is prepared by the method, the PAE resin is yellow transparent liquid, and the viscosity is 1000-4000CPS/25 ℃.
The long-acting antibacterial PAE resin can be used for preparing the bi-component polyurea terrace coating, and comprises a component A and a component B, wherein the component A comprises:
the long-acting bacteriostatic PAE resin has the advantages of long-acting bacteriostatic PAE resin,
at least one leveling agent,
at least one kind of bactericide which is capable of killing bacteria,
the component B comprises:
an isocyanate curing agent;
wherein the mass ratio of the component A to the component B is (2-2.5): 1.
Preferably, the component A long-acting antibacterial PAE resin accounts for 80-95% of the total mass of the component A, and more preferably, the mass percent is 85-90%; the at least one leveling agent accounts for 1-3% of the total mass of the component A.
The isocyanate curing agent of the invention can be selected from the existing isocyanate curing agents of the PAE two-component polyurea, including but not limited to any one of HDI tripolymer and IPDI tripolymer, preferably HDI tripolymer.
Further, the bactericide is selected from any one of nano-silica silver-carrying, nano-titania silver-carrying and nano-zirconia silver-carrying, and the addition amount of the bactericide accounts for 0.1-15% of the component A.
The leveling agent is an organic silicon or acrylic paint common leveling agent, such as BYK-300, BYK-301, BYK-310, BYK-388 and the like which are series products of Bike chemistry.
In addition, the component A can also be added with aggregate, color paste and other components commonly used for polyurea terraces, and the components are adjusted by the technical personnel in the field according to the actual use condition.
Has the advantages that: the long-acting antibacterial PAE resin provided by the invention forms four-season ammonium ion dendritic macromolecules, the fluidity of the long-acting antibacterial PAE resin is better due to the high-degree branching characteristic of the long-acting antibacterial PAE resin, and the resin has sufficient operation time during construction of a polyurea bi-component terrace by grasping the proportion; meanwhile, the dendritic macromolecular structure contains a large number of cavities, so that the nano-silver antibacterial floor has a good effect on stabilizing and dispersing nano-silver, and the antibacterial effect of the nano-silver antibacterial floor is not easy to decline obviously along with long-time use or aging of the floor.
Detailed Description
The present invention is further illustrated by the following specific examples.
Example 1
Adding a xylene solution containing dimethyl maleate and hydroxyl quaternary ammonium salt into a reaction container, wherein the molar ratio of the dimethyl maleate to the hydroxyl quaternary ammonium salt is 1 (2-2.5), then adding 0.01-0.1 wt% of p-toluenesulfonic acid catalyst, carrying out ester exchange reaction for 4-8 hours at 120-140 ℃, and separating xylene to obtain the maleate quaternary ammonium salt.
And then adding aliphatic diamine into another reaction container, dropwise adding maleic acid ester quaternary ammonium salt under the condition of introducing nitrogen, wherein the molar ratio of the aliphatic diamine to the maleic acid quaternary ammonium salt is 1 (2-2.5), heating to 60-65 ℃ at the end of the reaction, and keeping the temperature for 24-36 hours to obtain the long-acting antibacterial PAE resin.
Wherein, the hydroxyl quaternary ammonium salt is selected from hydroxymethyl trimethyl ammonium chloride or 2-hydroxypropyl trimethyl ammonium chloride; the aliphatic diamine is selected from 4, 4' -diaminodicyclohexylmethane, 1, 6-hexamethylene diamine and isophorone diamine.
Example 2
Dimethyl maleate and hydroxymethyl trimethyl ammonium bromide are mixed according to the molar ratio of 1:2.1, then the mixture is added into a reaction vessel containing a xylene solvent, 0.05 wt% of p-toluenesulfonic acid is added as a catalyst to carry out ester exchange reaction for 6 hours at 130 ℃, and xylene is separated to obtain maleic acid ester quaternary ammonium salt.
And then adding 4,4 '-diaminodicyclohexyl methane into another reaction vessel, dropwise adding maleic acid ester quaternary ammonium salt under the condition of introducing nitrogen, wherein the molar ratio of the 4, 4' -diaminodicyclohexyl methane to the maleic acid quaternary ammonium salt is 1:2.1, heating to 60-65 ℃ at the end of the reaction, and preserving heat for 30 hours to obtain the long-acting antibacterial PAE resin.
The PAE resin was a clear liquid orange in color and had a viscosity of 2400CPS/25 ℃.
Example 3
Mixing dimethyl maleate and hydroxymethyl trimethyl ammonium chloride according to a molar ratio of 1:2.4, adding the mixture into a reaction container containing a xylene solvent, adding 0.08 wt% of p-toluenesulfonic acid serving as a catalyst, performing ester exchange reaction for 6 hours at 130 ℃, and separating xylene to obtain the maleate quaternary ammonium salt.
And adding isophorone diamine into another reaction container, dropwise adding maleic acid ester quaternary ammonium salt under the condition of introducing nitrogen, wherein the molar ratio of isophorone diamine to maleic acid quaternary ammonium salt is 1:2.1, heating to 60-65 ℃ at the end of the reaction, and keeping the temperature for 30 hours to obtain the long-acting antibacterial PAE resin.
The PAE resin was a yellow transparent liquid with a viscosity of 1500CPS/25 ℃.
Example 4
Dimethyl maleate and hydroxymethyl trimethyl ammonium chloride are mixed according to the molar ratio of 1:2.2, then added into a reaction vessel containing a xylene solvent, then added with 0.03 wt% of p-toluenesulfonic acid as a catalyst to carry out ester exchange reaction for 6 hours at 130 ℃, and xylene is separated to obtain maleate quaternary ammonium salt.
And then adding 1, 6-hexamethylene diamine into another reaction container, dropwise adding maleic acid ester quaternary ammonium salt under the condition of introducing nitrogen, wherein the molar ratio of the 1, 6-hexamethylene diamine to the maleic acid quaternary ammonium salt is 1:2, heating to 60-65 ℃ at the end of the reaction, and keeping the temperature for 30 hours to obtain the long-acting antibacterial PAE resin.
The PAE resin was a yellow transparent liquid with a viscosity of 1200CPS/25 ℃.
Example 5
Mixing dimethyl maleate and 2-hydroxypropyl trimethyl ammonium chloride according to a molar ratio of 1:2.3, adding the mixture into a reaction vessel containing a xylene solvent, adding 0.06 wt% of p-toluenesulfonic acid serving as a catalyst, performing ester exchange reaction at 130 ℃ for 5 hours, and separating xylene to obtain the maleate quaternary ammonium salt.
And then adding 4,4 '-diaminodicyclohexyl methane into another reaction vessel, dropwise adding maleic acid ester quaternary ammonium salt under the condition of introducing nitrogen, wherein the molar ratio of the 4, 4' -diaminodicyclohexyl methane to the maleic acid quaternary ammonium salt is 1:2.2, heating to 60-65 ℃ at the end of the reaction, and preserving heat for 32 hours to obtain the long-acting antibacterial PAE resin.
The PAE resin was a yellow transparent liquid with a viscosity of 2600CPS/25 ℃.
Example 6
The polyurea terrace coating provided by the embodiment comprises a component A and a component B,
the component A comprises the following components in percentage by mass:
the component B comprises:
HI 100100% basf
Wherein the mass ratio of the component A to the component B is 2: 1. Uniformly mixing the component A and the component B in proportion, and rolling and coating a paint film with the thickness of 60-200um by using a roller.
Example 7
The polyurea terrace coating provided by the embodiment comprises a component A and a component B,
the component A comprises the following components in percentage by mass:
the component B comprises:
HI 100100% basf
Wherein the mass ratio of the component A to the component B is 2: 1. Uniformly mixing the component A and the component B in proportion, and rolling and coating a paint film with the thickness of 60-200um by using a roller.
Example 8
The polyurea terrace coating provided by the embodiment comprises a component A and a component B,
the component A comprises the following components in percentage by mass:
the component B comprises:
HI 100100% basf
Wherein the mass ratio of the component A to the component B is 2: 1. Uniformly mixing the component A and the component B in proportion, and rolling and coating a paint film with the thickness of 60-200um by using a roller.
Comparative example
This example is based on a commercially available PAE polyurea coating comprising an a-component and a B-component, wherein:
the component A comprises the following components in percentage by mass:
the component B comprises:
HI 100100% basf
The mass ratio of the component A to the component B is 2: 1. Uniformly mixing the component A and the component B in proportion, and rolling and coating a paint film with the thickness of 60-200um by using a roller.
Test examples
Aiming at the above examples 6-8 and comparative examples, the service performance is detected according to the GB/T22374-2008 terrace coating standard, and a continuous antibacterial test is carried out by combining the QB/T2591-.
The continuous antibacterial test is to respectively dilute the freshly cultured test strains (staphylococcus aureus ATCC6538, escherichia coli 8099 and aspergillus niger ATCC16404), inoculate the diluted test strains on the surface of a completely solidified paint film, sample and measure the test strains according to the same area after inoculating for 48 hours, compare positive control and calculate the antibacterial rate.
When the standard detection of the floor coating is about the items of GB/T1768-2006 color paint and varnish abrasion resistance determination, the antibacterial rate of staphylococcus aureus is determined once again on a paint film abraded by 500 turns of rubber grinding wheels, and the antibacterial rate is calculated after inoculation for 48 hours.
When the determination items of a damp-heat resistance determination method of a paint film of a terrace paint damp-heat aging standard GB/T1740-2007 are used, the paint film is placed in a relative humidity (96 +/-2)%, a temperature (60 +/-1) ° C continuous experiment is carried out for 72 hours, then the bacteriostatic rate of staphylococcus aureus is determined, and the bacteriostatic rate is calculated after inoculation for 48 hours.
The results of the above tests are summarized in table 1:
TABLE 1 floor coating service performance and thermal insulation Performance test
As can be seen from Table 1, the floor coating prepared based on the long-acting antibacterial PAE resin ensures the basic service performance of the floor, has the antibacterial rate of more than 90% on golden grapes, escherichia coli and aspergillus niger and has a certain long-acting antibacterial effect. After quantitative abrasion, the abrasion of the paint films of all groups is different, and the antibacterial effect of the paint films after long-term abrasion is evaluated by an antibacterial test, so that the terrace paint provided by the invention still has an obvious and strong antibacterial effect. The bacteriostasis effect of the paint film after the simulated accelerated aging is still remarkable after the bacteriostasis experiment is carried out on the paint film. The coating still has strong bacteriostatic action in long-term use.
Claims (11)
1. A preparation method of long-acting antibacterial PAE resin is characterized by comprising the following steps: adding a xylene solution containing dimethyl maleate and hydroxyl quaternary ammonium salt into a reaction container, adding a catalyst to perform ester exchange reaction, and separating the solvent to obtain maleic acid ester quaternary ammonium salt; adding aliphatic diamine into a reaction container, dropwise adding quaternary ammonium salt of maleate under the condition of introducing nitrogen, and preserving heat after the dropwise adding end point to obtain the long-acting antibacterial PAE resin.
2. The method of claim 1, wherein: the ammonium ions of the hydroxyl quaternary ammonium salt are connected with the same or different C1-C3 linear alkyl, and the anions are selected from F-、Cl-、Br-、I-Any one of the above.
3. The method of claim 2, wherein: the hydroxyl quaternary ammonium salt is hydroxymethyl trimethyl ammonium chloride or 2-hydroxypropyl trimethyl ammonium chloride.
4. The method of claim 2, wherein: the catalyst comprises any one or combination of more of sodium methoxide, triethylamine and p-toluenesulfonic acid; the input amount of the catalyst is 0.01-0.1 wt%.
5. The method according to any one of claims 1 to 4, wherein: the molar ratio of the dimethyl maleate to the hydroxyl quaternary ammonium salt is 1 (2-2.5).
6. The method of claim 5, wherein: the aliphatic diamine is C2-C14 saturated alkyl diamine and is selected from any one of 4, 4' -diaminodicyclohexylmethane, 1, 6-hexamethylene diamine, isophorone diamine and m-xylylenediamine.
7. The method of claim 6, wherein: the molar ratio of the aliphatic diamine to the quaternary ammonium maleate is 1 (2-2.5).
8. The method of claim 7, wherein: and (3) dropwise adding quaternary ammonium maleate until the reaction end, heating to 60-65 ℃, and keeping the temperature for 24-36 hours.
9. A long-acting bacteriostatic PAE resin prepared by the method of claim 1.
10. The long-acting bacteriostatic PAE bi-component polyurea floor coating is characterized by comprising a component A and a component B:
a component comprising
The long-acting bacteriostatic PAE resin of claim 10,
at least one leveling agent,
at least one kind of bactericide which is capable of killing bacteria,
component B comprising
An isocyanate curing agent;
the mass ratio of the component A to the component B is (2-2.5): 1.
11. The floor coating of claim 10, characterized in that: the bactericide is selected from any one of nano-silica silver-loaded, nano-titanium dioxide silver-loaded and nano-zirconia silver-loaded.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113604141A (en) * | 2021-07-20 | 2021-11-05 | 姜山 | PAE polyurea millstone terrace coating |
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| CN102796263A (en) * | 2012-08-28 | 2012-11-28 | 华北电力大学（保定） | Polyaspartic acid synthesized by microwave half-solvent method |
| CN103304815A (en) * | 2013-06-13 | 2013-09-18 | 扬州大学 | Preparation method for synthesizing polyaspartic acid by using ionic liquid |
| CN107475320A (en) * | 2017-08-23 | 2017-12-15 | 安徽雪郎生物科技股份有限公司 | The Green production method of L asparatates |
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|---|---|---|---|---|
| KR20080020902A (en) * | 2006-09-01 | 2008-03-06 | 동우 화인켐 주식회사 | Curing resin compositing having excellent hardeness |
| CN102146161A (en) * | 2010-02-05 | 2011-08-10 | 湖州欣和环境科技有限公司 | Polyaspartic acid complex for scale inhibitor |
| CN101768268A (en) * | 2010-02-11 | 2010-07-07 | 山东省泰和水处理有限公司 | Method for preparing polyaspartic acid by crystal condensation |
| CN102796263A (en) * | 2012-08-28 | 2012-11-28 | 华北电力大学（保定） | Polyaspartic acid synthesized by microwave half-solvent method |
| CN103304815A (en) * | 2013-06-13 | 2013-09-18 | 扬州大学 | Preparation method for synthesizing polyaspartic acid by using ionic liquid |
| CN107475320A (en) * | 2017-08-23 | 2017-12-15 | 安徽雪郎生物科技股份有限公司 | The Green production method of L asparatates |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113604141A (en) * | 2021-07-20 | 2021-11-05 | 姜山 | PAE polyurea millstone terrace coating |
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