CN114149338B - Preparation method and application of amphiphilic dendritic molecule - Google Patents
Preparation method and application of amphiphilic dendritic molecule Download PDFInfo
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- CN114149338B CN114149338B CN202111070484.3A CN202111070484A CN114149338B CN 114149338 B CN114149338 B CN 114149338B CN 202111070484 A CN202111070484 A CN 202111070484A CN 114149338 B CN114149338 B CN 114149338B
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- 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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- C07C231/00—Preparation of carboxylic acid amides
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
The invention discloses a preparation method and application of an amphiphilic dendritic molecule, wherein the method comprises the following steps: (1) Reacting the acrylate compound shown in the formula A with ethylenediamine to prepare 0.5 generation dendritic molecules; (2) Adding ethylenediamine into the 0.5 generation dendritic molecules obtained in the step (1) for reaction to prepare 1.0 generation dendritic molecules; (3) And (3) reacting the 1.0 generation dendritic molecule obtained in the step (2) with an acrylate compound shown in a formula B to prepare the amphiphilic dendritic molecule. The invention belongs to the field of emulsification of the amphiphilic dendritic molecular asphalt, and can obviously reduce the viscosity of the emulsified asphalt and increase the stability of the emulsified asphalt.
Description
Technical Field
The invention belongs to the field of polymer materials, and particularly relates to a preparation method and application of an amphiphilic dendritic molecule.
Background
In recent years, with the continuous and rapid development of the economy of China, the highway construction of China is developed in a large scale and occupies a large proportion in the national infrastructure. The continuous development and expansion of road networks in China make the scale of road maintenance increasingly huge. The traditional road maintenance concept of 'heavy maintenance and light prevention' in China causes that the preventive maintenance of the asphalt pavement is not emphasized, and under the action of high-temperature and rainy weather conditions and increasing vehicle loads, the pavement is easy to suffer from early diseases such as ruts, cracks, pits and the like, so that the driving safety and comfort are influenced, and the service life of the pavement is shortened. Therefore, it is important to pay more attention to the problem of asphalt pavement diseases, improve the quality and service life of asphalt pavements, and timely maintain the pavements.
Asphalt is a mixture composed of a plurality of macromolecules with complex chemical components and has unique rheological properties. Because of its good adhesion, aging resistance and water-proofing ability, it has been widely used for a long time for water-proofing and sealing materials, road repairs and the like. Emulsified asphalt exhibits significant advantages over hot asphalt. Emulsified asphalt can increase the uniformity of a road surface, the more compact cohesiveness of a roadbed structure can quickly restore an aged road surface, a large amount of energy can be saved, the energy can be saved by more than 50% by building a road with emulsified asphalt compared with the way with hot asphalt, the construction space is widened, the construction time is saved, and the construction cost is greatly reduced.
However, the viscosity of the emulsified asphalt in the prior art is high, so that the emulsified asphalt is difficult to apply in the practical process; there is thus a need for improvements in the raw materials for emulsified asphalt and the process for preparing the same.
Disclosure of Invention
In order to improve the above technical problems, the present invention provides a method for preparing an amphiphilic dendrimer, the method comprising the steps of:
(1) Reacting the acrylate compound shown in the formula A with ethylenediamine to prepare 0.5 generation dendritic molecules;
(2) Adding ethylenediamine into the 0.5 generation dendritic molecules obtained in the step (1) for reaction to prepare 1.0 generation dendritic molecules;
(3) Reacting the 1.0 generation of dendritic molecules obtained in the step (2) with an acrylate compound shown as a formula B to prepare amphiphilic dendritic molecules;
in the formula A, R 1 、R 2 、R 3 Identical or different, independently of one another, from H, C 1-20 Alkyl radical, C 6-20 An aryl group;
R 4 selected from unsubstituted or optionally substituted by one or more R b Substituted C 1-20 Alkyl radical, C 6-20 Aryl, -O-C 1-20 Alkyl, -C 1-20 An alkyl sulfonate;
R b is selected from-O-C 1-20 An alkyl group;
in the formula B, R 5 、R 6 、R 7 Identical or different, independently of one another, from H, C 1-20 Alkyl radical, C 6-20 An aryl group;
R 8 selected from unsubstituted or optionally substituted by one or more R a Substituted C 1-20 Alkyl radical, C 6-20 Aryl, -O-C 1-20 Alkyl, -C 1-20 Alkylsulfonic acid salts, -C 1-20 alkyl-C 6-20 An aryl group;
R a is selected from-O-C 1-20 Alkyl or-O-C 1-20 alkylene-O-C 1-20 An alkyl group.
According to the invention, in formula A, R 1 、R 2 、R 3 Same or different and independently selected from H, C 1-6 Alkyl radical, C 6-14 Aryl radical, R 4 Selected from H, C 1-6 Alkyl radical, C 6-14 Aryl, -C 1-6 Alkyl sulfonates, or substituted by one or more R b Substituted C 1-6 An alkyl group. More preferably, R 1 、R 2 、R 3 Are all H, R 4 Is a methyl group.
According to the invention, the acrylate compound shown in the formula A is preferably methyl acrylate.
According to the invention, in the formula B, R 5 、R 6 、R 7 Same or different and independently selected from H, C 1-6 Alkyl radical, C 6-14 An aryl group;
R 8 selected from H, C 1-6 Alkyl radical, C 6-14 Aryl, -C 1-6 Alkylsulfonic acid salts, -C 1-6 alkyl-C 6-14 Aryl or by one or more R a Substituted C 1-6 Alkyl, wherein R a Is selected from-O-C 1-6 Alkyl or-O-C 1-6 alkylene-O-C 1-6 An alkyl group.
According to the invention, in the step (3), the acrylate compound shown in the formula B is at least one selected from benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, 2-phenyl acrylic acid, 9-anthracene methyl methacrylate and 3-sulfopropyl methacrylate potassium salt.
According to the invention, in the step (1), the solvent is one or more of methanol, ethanol, propanol and acetone, and accounts for 30-70% of the total reaction raw materials by mass.
In the invention, the amphiphilic dendritic molecules contain a dendritic structure, a hydrophilic structure and a hydrophobic structure.
According to the invention, in the step (1), the mass ratio of the acrylate compound represented by the formula A to the ethylenediamine is 4 to 8.
According to the present invention, step (1) may further comprise a post-treatment step, for example, distillation of the product under reduced pressure to remove the solvent and unreacted acrylate compound represented by formula A.
According to the invention, in step (2), the molar ratio of 0.5 generation dendrimer to ethylenediamine is 1.
According to the present invention, the step (2) may further comprise a post-treatment step, for example, distillation of the product under reduced pressure to remove the solvent and unreacted ethylenediamine.
According to the invention, in the step (3), the molar ratio of the 1.0 generation dendrimer to the acrylate compound shown in the formula B is 1.
According to the invention, in step (3), the 1.0 generation dendrimer is dissolved in the solvent and then added dropwise to the acrylate compound represented by formula B.
According to the present invention, the step (3) may further comprise a post-treatment step, for example, distillation of the product under reduced pressure to remove the solvent and unreacted acrylate compound represented by formula B.
According to the invention, the preparation method belongs to a divergent method synthesis reaction, the reaction is carried out under the protection of inert gas, and the reaction temperature is 15-60 ℃, preferably 30 ℃.
As a preferred embodiment of the present invention, the preparation method specifically comprises the steps of:
(S1) Synthesis of 0.5 Generation dendrimer: under the protection of nitrogen, ethylenediamine (EDA) dissolved in methanol was dropwise added to an excess amount of purified Methyl Acrylate (MA), reacted at 30 ℃ for 24 hours under magnetic stirring, and then distilled under reduced pressure to remove methanol and unreacted MA, thereby obtaining 0.5-generation dendrimer.
(S2) Synthesis of 1.0 Generation dendrimer: dissolving 0.5 generation of dendrimer in the step (S1) in methanol, dropwise adding into excessive EDA under the protection of nitrogen, reacting for 96 hours under magnetic stirring at 30 ℃, and carrying out reduced pressure distillation to remove methanol and unreacted EDA, thus obtaining 1.0 generation of dendrimer;
wherein, the reaction process of the step (S1) and the step (S2) is as follows:
(S3) synthesis of amphiphilic dendrimer: dropwise adding the dendrimer of 1.0 generation dissolved in the methanol in the step (2) into excessive purified acrylate compounds shown in the formula B under the protection of nitrogen, reacting for 24 hours under magnetic stirring at 30 ℃, and distilling under reduced pressure to remove the methanol and unreacted acrylate compounds to obtain the amphiphilic dendrimer.
The invention also provides an amphiphilic dendritic molecule, which is prepared by the method.
The invention also provides application of the amphiphilic dendritic molecule, which is applied to the field of asphalt emulsification and can obviously reduce the viscosity of emulsified asphalt and increase the stability of the emulsified asphalt.
Advantageous effects
The invention successfully prepares the amphiphilic dendritic molecule, and can obviously reduce the viscosity of the emulsified asphalt and increase the stability of the emulsified asphalt in the field of asphalt emulsification of the amphiphilic dendritic molecule.
Definition and description of terms
“C 1-20 Alkyl "is understood to mean a straight-chain or branched saturated monovalent hydrocarbon radical having from 1 to 20 carbon atoms. For example, "C 1-10 Alkyl "denotes straight-chain and branched alkyl groups having 1,2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms," C 1-6 Alkyl "denotes straight and branched chain alkyl groups having 1,2, 3, 4, 5 or 6 carbon atoms. The alkyl group is, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-ethylpropyl, 1, 2-dimethylpropyl, neopentyl, 1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3-dimethylbutyl, 2-dimethylbutyl, 1-dimethylbutyl, 2, 3-dimethylbutyl, 1, 3-dimethylbutyl, or 1, 2-dimethylbutyl, etc., or isomers thereof.
The term "C 6-20 Aryl "is to be understood as preferably meaning a mono-, bi-or tricyclic hydrocarbon ring of monovalent or partially aromatic character having from 6 to 20 carbon atoms, preferably" C 6-14 Aryl ". The term "C 6-14 Aryl "is to be understood as preferably meaning a mono-, bi-or tricyclic hydrocarbon ring having a monovalent or partially aromatic character with 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms (" C 6-14 Aryl group "), in particular a ring having 6 carbon atoms (" C 6 Aryl "), such as phenyl; or biphenyl, or is a ring having 9 carbon atoms ("C 9 Aryl), such as indanyl or indenyl, or a ring having 10 carbon atoms ("C 10 Aryl radicals), such as tetralinyl, dihydronaphthyl or naphthyl, or rings having 13 carbon atoms ("C 13 Aryl radicals), such as the fluorenyl radical, or a ring having 14 carbon atoms ("C) 14 Aryl), such as anthracyl. When said C is 6-20 When the aryl group is substituted, it may be mono-or polysubstituted. And, the substitution site thereof is not limited, and may be, for example, ortho-, para-or meta-substitution.
Detailed Description
The technical solution of the present invention will be further described in detail with reference to specific embodiments. It is to be understood that the following examples are only illustrative and explanatory of the present invention and should not be construed as limiting the scope of the present invention. All the techniques realized based on the above-mentioned contents of the present invention are covered in the protection scope of the present invention.
Unless otherwise indicated, the raw materials and reagents used in the following examples are all commercially available products or can be prepared by known methods.
In examples 1-8, both the 0.5 generation dendrimer and the 1.0 generation dendrimer were prepared as follows:
(S1) Synthesis of 0.5 Generation dendrimer: under nitrogen protection, 30g of Ethylenediamine (EDA) dissolved in methanol was added dropwise to an excess of purified 180.79g of Methyl Acrylate (MA), and after reaction for 24 hours at 30 ℃ under magnetic stirring, methanol and unreacted MA were removed by distillation under reduced pressure to obtain 0.5-generation dendrimer.
(S2) Synthesis of 1.0 Generation dendrimer: dissolving 202.23g of 0.5 generation dendrimer in the step (S1) in methanol, dropwise adding into 144.24g of excessive EDA under the protection of nitrogen, reacting for 96 hours under magnetic stirring at 30 ℃, and then carrying out reduced pressure distillation to remove the methanol and the unreacted EDA, thus obtaining the 1.0 generation dendrimer;
wherein, the reaction process of the step (S1) and the step (S2) is as follows:
example 1
The preparation method of the amphiphilic dendrimer of this example:
synthesis of amphiphilic dendrimers: under the protection of nitrogen, 258.35g of generation 1.0 dendrimer dissolved in methanol is dropwise added into excessive purified benzyl methacrylate, wherein the molar ratio of the generation 1.0 dendrimer to the benzyl methacrylate is 1.4, the reaction is carried out at 30 ℃ for 24 hours under magnetic stirring, and then the amphiphilic dendrimer is obtained by reduced pressure distillation to remove the methanol and unreacted acrylic compounds.
Example 2
The preparation method of amphiphilic dendritic molecules of this example:
synthesis of amphiphilic dendrimers: 258.35g of generation 1.0 dendrimer dissolved in methanol was dropwise added to excess purified 2- (2-ethoxyethoxy) ethyl acrylate under nitrogen protection, wherein the molar ratio of the generation 1.0 dendrimer to the generation 2- (2-ethoxyethoxy) ethyl acrylate was 1.4, and after 24 hours of reaction under magnetic stirring at 30 ℃, the amphiphilic dendrimer was obtained by distillation under reduced pressure to remove methanol and unreacted acrylic compound.
Example 3
The preparation method of amphiphilic dendritic molecules of this example:
synthesis of amphiphilic dendrimers: under the protection of nitrogen, 258.35g of generation 1.0 dendrimer dissolved in methanol is dropwise added into excessive purified methacrylic acid-9-anthracene methyl ester, wherein the molar ratio of the generation 1.0 dendrimer to the generation 9-anthracene methyl ester is 1.
Example 4
The preparation method of the amphiphilic dendrimer of this example:
synthesis of amphiphilic dendrimers: under the protection of nitrogen, 258.35g of generation 1.0 dendrimer dissolved in methanol was added dropwise to an excess of the mixture of purified 2- (2-ethoxyethoxy) ethyl acrylate and 9-anthracenemethyl methacrylate (wherein the molar ratio of 2- (2-ethoxyethoxy) ethyl acrylate to 9-anthracenemethyl methacrylate was 7).
Example 5
The preparation method of amphiphilic dendritic molecules of this example: synthesis of amphiphilic dendrimers: under nitrogen protection, 258.35g of generation 1.0 dendrimers dissolved in methanol was added dropwise to an excess of a mixture of purified benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, and 3-sulfopropyl methacrylate potassium salt (wherein the molar ratio of benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, and 3-sulfopropyl methacrylate potassium salt is 2.
Example 6
The preparation method of the amphiphilic dendrimer of this example: synthesis of amphiphilic dendrimers: under nitrogen protection, 258.35g of generation 1.0 dendrimer dissolved in methanol was added dropwise to an excess of a mixture of purified benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, 9-anthracenemethylmethacrylate, and 3-sulfopropyl methacrylate potassium salt (molar ratio of benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, 9-anthracenemethylmethacrylate, and 3-sulfopropyl methacrylate potassium salt was 1.5: 0.5), wherein the molar ratio of generation 1.0 dendrimer to the sum of moles of benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, 9-anthracenemethylmethacrylate, and 3-sulfopropyl methacrylate potassium salt was 1.4, and after 24 hours of reaction under magnetic stirring at 30 ℃, methanol and unreacted acrylic compound were removed by distillation under reduced pressure to obtain amphiphilic dendrimer.
Example 7
The preparation method of amphiphilic dendritic molecules of this example: synthesis of amphiphilic dendrimers: under nitrogen protection, 258.35g of generation 1.0 dendrimer dissolved in methanol was added dropwise to an excess of a mixture of purified benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, 2-phenylacrylic acid, 9-anthracenemethylmethacrylate, and 3-sulfopropyl methacrylate potassium salt (wherein the molar ratio of benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, 2-phenylacrylic acid, 9-anthracenemethylmethacrylate, and 3-sulfopropyl methacrylate potassium salt is 1.5.
Example 8
For the amphiphilic dendrimers prepared in examples 1 to 7, the bitumen was emulsified using a solution of a certain concentration under certain conditions and the viscosity and the settling time of the bitumen emulsion were determined. The specific test process is as follows:
a solution of amphiphilic dendrimers at a mass concentration of 2% was prepared using a sodium hydroxide solution at pH = 13. Adding 180g of amphiphilic dendritic molecular solution with the mass concentration of 2% at 75 ℃ into a colloid mill, adding 220g of flowable asphalt (such as coal tar pitch or petroleum asphalt) which is fully heated at 130 ℃ into the colloid mill under the condition that the colloid mill is operated, emulsifying for 40 seconds, pouring the emulsified asphalt into a 500mL beaker, fully cooling, measuring the viscosity of the emulsified asphalt at normal temperature by using a Brookfield viscometer, and then sealing the opening of the beaker, standing and observing the stabilization time of the emulsified asphalt, wherein the stabilization time takes the precipitation or generation of precipitates of the emulsified asphalt as the deadline.
The results are shown in Table 1.
TABLE 1 viscosity and stabilization time of emulsified asphalt prepared from amphiphilic dendrimers prepared in examples 1-7
The embodiments of the present invention have been described above by way of example. However, the scope of the present invention is not limited to the above embodiments. Any modification, equivalent replacement, improvement and the like made by those skilled in the art within the spirit and principle of the present invention shall be included in the protection scope of the present invention.
Claims (6)
1. A method of making an amphiphilic dendrimer, the method comprising the steps of:
(1) Reacting methyl acrylate with ethylenediamine to prepare 0.5 generation dendritic molecules;
(2) Adding ethylenediamine into the 0.5 generation dendritic molecules obtained in the step (1) for reaction to prepare 1.0 generation dendritic molecules;
(3) Reacting the 1.0 generation dendritic molecule obtained in the step (2) with an acrylate compound of a formula B,
preparing an amphiphilic dendritic molecule;
the acrylate compound of the formula B is benzyl methacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, 9-anthracenemethacrylate, 3-sulfopropyl methacrylate potassium salt, 2-phenylacrylic acid or a mixture thereof;
the method is carried out in the presence of a solvent, wherein the solvent is one or more of methanol, ethanol, propanol and acetone, and accounts for 30-70% of the total reaction raw materials by mass.
2. The production method according to claim 1, wherein in the step (1), the mass ratio of methyl acrylate to ethylenediamine is 4 to 8.
3. The method according to claim 1, wherein in the step (2), the molar ratio of 0.5 generation dendrimer to ethylenediamine is 1.
4. The method according to claim 1, wherein in the step (3), the molar ratio of the 1.0 generation dendrimer to the acrylate compound represented by the formula B is 1.2 to 4.8.
5. An amphiphilic dendrimer prepared according to the method of any one of claims 1 to 4.
6. Use of an amphiphilic dendrimer according to claim 5, wherein the use is in the field of asphalt emulsification.
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