CN106867405B - A kind of hydrophobic coating and preparation method thereof based on polyamide-amide dendrimer - Google Patents
A kind of hydrophobic coating and preparation method thereof based on polyamide-amide dendrimer Download PDFInfo
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- CN106867405B CN106867405B CN201710126805.4A CN201710126805A CN106867405B CN 106867405 B CN106867405 B CN 106867405B CN 201710126805 A CN201710126805 A CN 201710126805A CN 106867405 B CN106867405 B CN 106867405B
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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
- C09D187/00—Coating compositions based on unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
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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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/14—Carboxylic acids; Derivatives thereof
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
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Abstract
The present invention relates to a kind of hydrophobic coating and preparation method thereof based on polyamide-amide dendrimer, belongs to hydrophobic material field.Each component and its molar ratio in the formula of the hydrophobic coating are as follows: dendrimer: hydrophobic surface modifier=1:64~1:128；The preparation method is made using polyamide-amide dendrimer and long-chain aliphatic acrylate as raw material by a step Michael addition reaction.The method of the present invention is easy to operate, safe, and preparation condition is mild, and prepared hydrophobic coating is not fluorine-containing, small toxicity, is suitble to large-scale industrial production.
Description
Technical field
The present invention relates to a kind of hydrophobic coating and preparation method thereof based on polyamide-amide dendrimer, belongs to hydrophobic material
Material field.
Technical background
Hydrophobicity is a critical nature of the surface of solids, is usually measured with the angle between drop and solid, i.e.,
Contact angle.Contact angle is bigger, then the hydrophobicity of the surface of solids is better.Surface usually by contact angle less than 90 ° is known as hydrophilic table
Face, surface of the contact angle greater than 90 ° are known as hydrophobic surface.Hydrophobic surface is because it is with many excellent surface propertys, such as from clear
The characteristics such as clean, antifouling, anticorrosion, anti-oxidation in industrial and agricultural productions such as automatically cleaning, fluid drag-reduction, biomedical materials, are commercially answered
It is had broad application prospects in field with, national defense construction.
There are mainly two types of the approach for realizing hydrophobic surface: first is that modifying low-surface energy substance on a rough surface, usually using
In the main polysiloxane of low-surface-energy material, fluorocarbons and other organic matters for preparing hydrophobic surface, (such as polyethylene gathers
Styrene etc.)；Second is that constructing the coarse structure of similar lotus leaf surface, preparation method organic/inorganic nano particle on hydrophobic material surface
(such as TiO2, SiO2, ZnO) modification, laser/plasma/chemical etching, template, method of electrostatic spinning, sol-gel, from
The numerous species such as assembling, electrochemical deposition and chemical vapor deposition.But in the above-mentioned methods, it largely requires to prepared
Surface is using progress pattern modification, or carries out surface in advance to particle used (such as silica, metal oxide particle)
Processing, preparation process is cumbersome, and cost is relatively high with energy consumption, and part hydrophobic coating contains fluorine etc. to the poisonous and harmful member of human body
Element, this brings big inconvenience to making and using for hydrophobic coating.Therefore develop it is a kind of prepare simplicity, be free of toxic element
Hydrophobic coating have a very big significance.
Polyamide-amide (PAMAM) dendrimer be it is a kind of with three-dimensional molecular structure, highly branched and high-sequential tree
Dendrimer, it is other than the general character with branch compound, also with good thermal stability, water solubility, special viscous
The characteristics such as degree and surface tension, other than showing huge application prospect in terms of biomedicine, material, in waste water
The chemical fields such as processing, oil exploitation, gas purification or separation have also shown good purposes.But because polyamide-amide tree
Shape intramolecule contains a large amount of hydrophilic amide groups, and whole that hydrophily is presented, how to shield inner hydrophilic group is that will gather
Amide-amine dendrimer is prepared as a difficult point of hydrophobic coating.Therefore do not have also and be applied to dredge by polyamide-amide dendrimer
The report of water paint.
Summary of the invention
In view of this, one of the objects of the present invention is to provide a kind of hydrophobic coatings based on polyamide-amide dendrimer；
The second purpose is to provide a kind of preparation method of hydrophobic coating based on polyamide-amide dendrimer, this method is easy to operate,
Without fluorine element, without being surface-treated in advance to substrate.
To achieve the purpose of the present invention, technical solution once is provided:
A kind of hydrophobic coating based on polyamide-amide dendrimer each component and its rubs in the formula of the hydrophobic coating
That ratio are as follows: dendrimer: hydrophobic surface modifier=1:64~1:128；
The dendrimer is the polyamide-amide dendrimer of all amino in surface；
The hydrophobic surface modifier is long-chain aliphatic acrylate, and structural formula is as follows:
n≥6；
The preferred Process Conditions of Cetane Acrylate of the long-chain aliphatic acrylate, octadecyl acrylate or Behenyl acrylate.
Preferably, the dendrimer is 4.0 polyamide-amide dendrimer more than generation.
A kind of preparation method of the hydrophobic coating based on polyamide-amide dendrimer, specific step is as follows for the method:
(1) being dissolved into dissolution in organic solvent a to obtain concentration by dendrimer is 3 × 10-3~3 × 10-4Mol/L solution
1；
(2) hydrophobic surface modifier is dissolved into organic solvent b, it is the molten of 0.5~0.01mol/L that dissolution, which obtains concentration,
Liquid 2；
(3) solution 1 is heated with stirring to 20~50 DEG C, under nitrogen atmosphere and stirring condition, by solution 2 with 2~3s/ drop
Speed be added dropwise in solution 1,6~18h of isothermal reaction under nitrogen atmosphere obtains solution 3；
(4) under 50 DEG C~55 DEG C, 0.098~0.1MPa vacuum degree, solution 3 is rotated and removes solvent, obtains a kind of base
In the hydrophobic coating of polyamide-amide dendrimer；
Step (1) the organic solvent a is preferably methanol, ethyl alcohol or isopropanol；
Step (2) the organic solvent b is preferably n-hexane or hexamethylene；
Beneficial effect
1. not only hydrophobic performance is good, but also is not necessarily to after hydrophobic coating of the invention is coated on composite material base bottom surface
Be surface modified using low-surface energy substance or in advance to modified using particle, can be used for the large area of hydrophobic surface
Preparation and long-time service.
2. dendrimer hydrophobic coating of the present invention is free of fluorine element, environmentally friendly, nontoxic to the human body.
3. preparation method of the invention has the characteristics of simple and easy, to be not necessarily to large-scale instrument and equipment, be not necessarily to subsequent processing.
Detailed description of the invention
Fig. 1 is the water static contact angle figure of hydrophobic qualitative filter paper prepared by embodiment 1.
Specific embodiment
The present invention, but protection scope not thereby limiting the invention be described in detail combined with specific embodiments below.
Contact angle measurement: it is prepared using Dataphysics OCA20 type contact angle tester measurement water droplet in embodiment
Hydrophobic qualitative filter paper surface on contact angle, drop volume be 5 milliliters.By measuring same hydrophobic qualitative filter paper surface at least
5 different locations obtain the Average water contact angles on hydrophobic qualitative filter paper surface to the contact angle of water.
For the qualitative filter paper that no hydrophobic coating is modified, its hydrophobicity is tested:
Embodiment 1
(1) 4.0 polyamide-amine dendrimer 0.5000g are added in 50ml three-necked flask, methanol 25g, stirring is added
Sufficiently dissolution, obtains solution 1.
(2) 1.52g octadecyl acrylate is dissolved in 20g hexamethylene, stirs sufficiently dissolution, obtains solution 2.
(3) solution 1 is heated with stirring to 20 DEG C, under nitrogen atmosphere and stirring condition, by solution 2 with the speed of 2~3s/ drop
Degree is added dropwise in solution 1, and the lower 20 DEG C of reactions 6h of nitrogen atmosphere obtains solution 3.
(4) solution 3 is rotated under 50 DEG C, 0.099MPa vacuum degree and removes solvent, obtained a kind of based on polyamide-amide tree
The hydrophobic coating of shape molecule.
With qualitative filter paper (average pore size is 19 micron) for substrate, and it is immersed in the embodiment 1 that mass fraction is 2%
In the cyclohexane solution of the hydrophobic coating of preparation, deposit 5 minutes.The qualitative filter paper is taken out, 60 DEG C of vacuum drying is put into
It is dried in vacuo 30min in case, takes out naturally dry, obtain being covered with a kind of hydrophobic coating based on polyamide-amide dendrimer
Qualitative filter paper (hereinafter referred to as hydrophobic qualitative filter paper), test hydrophobic qualitative filter paper using contact angle measurement is to the contact angle of water
128.0 °, as shown in Figure 1.
Embodiment 2
(1) 4.0 polyamide-amine dendrimer 0.5000g are added in 50ml three-necked flask, ethyl alcohol 25g, stirring is added
Sufficiently dissolution, obtains solution 1.
(2) 2.26g Process Conditions of Cetane Acrylate is dissolved in 20g hexamethylene, stirs sufficiently dissolution, obtains solution 2.
(3) solution 1 is heated with stirring to 30 DEG C, under nitrogen atmosphere and stirring condition, by solution 2 with the speed of 2~3s/ drop
Degree is added dropwise in solution 1, and the lower 30 DEG C of reactions 18h of nitrogen atmosphere obtains solution 3.
(4) solution 3 is rotated under 50 DEG C, 0.099MPa vacuum degree and removes solvent, obtained a kind of based on polyamide-amide tree
The hydrophobic coating of shape molecule.
With qualitative filter paper (average pore size is 19 micron) for substrate, and it is immersed in the embodiment 2 that mass fraction is 2%
In the cyclohexane solution of the hydrophobic coating of preparation, deposit 5 minutes.The qualitative filter paper is taken out, 60 DEG C of vacuum drying is put into
It is dried in vacuo 30min in case, takes out naturally dry, obtains hydrophobic qualitative filter paper, tested using contact angle measurement hydrophobic qualitative
Filter paper is 130.1 ° to the contact angle of water.
Embodiment 3
(1) 4.0 polyamide-amine dendrimer 0.5000g are added in 50ml three-necked flask, isopropanol 25g is added, stirs
Abundant dissolution is mixed, solution 1 is obtained.
(2) 2.02g Behenyl acrylate is dissolved in 20g hexamethylene, stirs sufficiently dissolution, obtains solution 2.
(3) solution 1 is heated with stirring to 50 DEG C, under nitrogen atmosphere and stirring condition, by solution 2 with the speed of 2~3s/ drop
Degree is added dropwise in solution 1, and the lower 50 DEG C of reactions 6h of nitrogen atmosphere obtains solution 3.
(4) solution 3 is rotated under 50 DEG C, 0.099MPa vacuum degree and removes solvent, obtained a kind of based on polyamide-amide tree
The hydrophobic coating of shape molecule.
With qualitative filter paper (average pore size is 19 micron) for substrate, and it is immersed in the embodiment 3 that mass fraction is 2%
In the cyclohexane solution of the hydrophobic coating of preparation, deposit 5 minutes.The qualitative filter paper is taken out, 60 DEG C of vacuum drying is put into
It is dried in vacuo 30min in case, takes out naturally dry, obtains hydrophobic qualitative filter paper, tested using contact angle measurement hydrophobic qualitative
Filter paper is 132.0 ° to the contact angle of water.
Embodiment 4
(1) 4.0 polyamide-amine dendrimer 0.5000g are added in 50ml three-necked flask, isopropanol 25g is added, stirs
Abundant dissolution is mixed, solution 1 is obtained.
(2) 1.33g octadecyl acrylate is dissolved in 20g hexamethylene, stirs sufficiently dissolution, obtains solution 2.
(3) solution 1 is heated with stirring to 35 DEG C, under nitrogen atmosphere and stirring condition, by solution 2 with the speed of 2~3s/ drop
Degree is added dropwise in solution 1, and the lower 35 DEG C of reactions 12h of nitrogen atmosphere obtains solution 3.
(4) solution 3 is rotated under 50 DEG C, 0.099MPa vacuum degree and removes solvent, obtained a kind of based on polyamide-amide tree
The hydrophobic coating of shape molecule.
With qualitative filter paper (average pore size is 19 micron) for substrate, and it is immersed in the embodiment 4 that mass fraction is 2%
In the cyclohexane solution of the hydrophobic coating of preparation, deposit 5 minutes.The qualitative filter paper is taken out, 60 DEG C of vacuum drying is put into
It is dried in vacuo 30min in case, takes out naturally dry, obtains hydrophobic qualitative filter paper, test hydrophobic qualitative filter using contact angle measurement
Paper is 133.6 ° to the contact angle of water.
Embodiment 5
(1) 4.0 polyamide-amine dendrimer 0.5000g are added in 50ml three-necked flask, isopropanol 25g is added, stirs
Abundant dissolution is mixed, solution 1 is obtained.
(2) 1.33g octadecyl acrylate is dissolved in 20g n-hexane, stirs sufficiently dissolution, obtains solution 2.
(3) solution 1 is heated with stirring to 20 DEG C, under nitrogen atmosphere and stirring condition, by solution 2 with the speed of 2~3s/ drop
Degree is added dropwise in solution 1, and the lower 20 DEG C of reactions 6h of nitrogen atmosphere obtains solution 3.
(4) solution 3 is rotated under 50 DEG C, 0.099MPa vacuum degree and removes solvent, obtained a kind of based on polyamide-amide tree
The hydrophobic coating of shape molecule.
With qualitative filter paper (average pore size is 19 micron) for substrate, and it is immersed in the embodiment 5 that mass fraction is 2%
In the cyclohexane solution of the hydrophobic coating of preparation, deposit 5 minutes.The qualitative filter paper is taken out, 60 DEG C of vacuum drying is put into
It is dried in vacuo 30min in case, takes out naturally dry, obtains hydrophobic qualitative filter paper, tested using contact angle measurement hydrophobic qualitative
Filter paper is 125.1 ° to the contact angle of water.
Embodiment 6
(1) 4.0 polyamide-amine dendrimer 0.5000g are added in 50ml three-necked flask, isopropanol 25g is added, stirs
Abundant dissolution is mixed, solution 1 is obtained.
(2) 1.33g octadecyl acrylate is dissolved in 20g n-hexane, stirs sufficiently dissolution, obtains solution 2.
(3) solution 1 is heated with stirring to 20 DEG C, under nitrogen atmosphere and stirring condition, by solution 2 with the speed of 2~3s/ drop
Degree is added dropwise in solution 1, and the lower 20 DEG C of reactions 6h of nitrogen atmosphere obtains solution 3.
(4) solution 3 is rotated under 50 DEG C, 0.099MPa vacuum degree and removes solvent, obtained a kind of based on polyamide-amide tree
The hydrophobic coating of shape molecule.
With qualitative filter paper (average pore size is 19 micron) for substrate, and it is immersed in the embodiment 6 that mass fraction is 2%
In the cyclohexane solution of the hydrophobic coating of preparation, deposit 5 minutes.The qualitative filter paper is taken out, 60 DEG C of vacuum drying is put into
It is dried in vacuo 30min in case, takes out naturally dry, obtains hydrophobic qualitative filter paper, tested using contact angle measurement hydrophobic qualitative
Filter paper is 122.9 ° to the contact angle of water.
The present invention includes but is not limited to above embodiments, it is all carried out under the principle of spirit of that invention it is any equivalent
Replacement or local improvement, all will be regarded as within protection scope of the present invention.
Claims (4)
1. a kind of hydrophobic coating based on polyamide-amide dendrimer, it is characterised in that: each group in the formula of the hydrophobic coating
Point and its molar ratio are as follows: dendrimer: hydrophobic surface modifier=1:64~1:128；
The dendrimer is 4.0 polyamide-amine dendrimers of all amino in surface；
The hydrophobic surface modifier is long-chain aliphatic acrylate, and structural formula is as follows:
The hydrophobic coating is prepared via a method which:
(1) being dissolved into dissolution in organic solvent a to obtain concentration by dendrimer is 3 × 10-3~3 × 10-4Mol/L solution 1；
(2) hydrophobic surface modifier is dissolved into organic solvent b, dissolution obtains the solution 2 that concentration is 0.5~0.01mol/L；
(3) solution 1 is heated with stirring to 20~50 DEG C, under nitrogen atmosphere and stirring condition, by solution 2 with the speed of 2~3s/ drop
Degree is added dropwise in solution 1, and 6~18h of isothermal reaction under nitrogen atmosphere obtains solution 3；
(4) under 50 DEG C~55 DEG C, 0.098~0.1MPa vacuum degree, solution 3 is rotated and removes solvent, obtained a kind of based on poly-
The hydrophobic coating of amide-amine dendrimer.
2. a kind of hydrophobic coating based on polyamide-amide dendrimer as described in claim 1, it is characterised in that: the propylene
Sour long-chain alkyl groups are Process Conditions of Cetane Acrylate, octadecyl acrylate or Behenyl acrylate.
3. a kind of hydrophobic coating based on polyamide-amide dendrimer as described in claim 1, it is characterised in that: step (1) institute
Stating organic solvent a is methanol, ethyl alcohol or isopropanol.
4. a kind of hydrophobic coating based on polyamide-amide dendrimer as described in claim 1, it is characterised in that: step (2) institute
Stating organic solvent b is n-hexane or hexamethylene.
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| CN113150368B (en) * | 2020-11-23 | 2022-07-22 | 航天特种材料及工艺技术研究所 | Moisture-proof modified phenolic aldehyde heat-insulating material and preparation method thereof |
| CN112480467B (en) * | 2020-11-23 | 2022-07-22 | 航天特种材料及工艺技术研究所 | Moisture-proof modified phenolic aldehyde heat-insulating material and preparation method thereof |
| CN115197636A (en) * | 2022-07-07 | 2022-10-18 | 西安文理学院 | Hydrophobic and oleophobic coating material and preparation method thereof |
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2017
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| US6143809A (en) * | 1998-07-17 | 2000-11-07 | Shell Oil Company | Process to prepare aqueous dispersions of epoxy resins |
| US6231655B1 (en) * | 1999-03-19 | 2001-05-15 | Seiko Epson Corporation | Aqueous ink composition for use in an ink jet printer |
| US7608573B1 (en) * | 2008-08-26 | 2009-10-27 | The Clorox Company | Natural heavy duty cleaners |
| CN104479437A (en) * | 2015-01-06 | 2015-04-01 | 东华大学 | Preparation method for super-hydrophobic self-luminous coating |
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