CN108690466A - A kind of water-base epoxy ester and preparation method thereof based on bio-based materials - Google Patents
A kind of water-base epoxy ester and preparation method thereof based on bio-based materials Download PDFInfo
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- CN108690466A CN108690466A CN201810587010.8A CN201810587010A CN108690466A CN 108690466 A CN108690466 A CN 108690466A CN 201810587010 A CN201810587010 A CN 201810587010A CN 108690466 A CN108690466 A CN 108690466A
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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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1494—Polycondensates modified by chemical after-treatment followed by a further chemical treatment thereof
Abstract
The invention discloses a kind of water-base epoxy ester and preparation method thereof based on bio-based materials.The preparation method includes the following steps:S1. the biodiesel of the gutter oil alcoholysis liquid of 35~45 parts by weight, the biology base succinic acid of 10~15 parts by weight, the polyester waste material of 5~10 mass parts, 8~12 parts by weight glycerine is refined to mix;S2. after mixture reaction a period of time of heating stepses S1, epoxy resin reaction a period of time of 15~25 parts by weight is added;S3. the trimellitic anhydride for 5~8 parts by weight being added into the product of step S2 is reacted, and is cooled down after the acid value of product is less than 35;S4. the butyl glycol ether of 25~35 parts by weight is added into the product of step S3;S5. the neutralizer of 3~4 parts by weight is added into the product of step S4 into salt.The present invention prepares water-base epoxy ester using bio-based materials (gutter oil, biology base succinic acid and biodiesel refine glycerine) as main raw material, and practicability is good.
Description
Technical field
The present invention relates to paint field more particularly to a kind of water-base epoxy esters and its preparation side based on bio-based materials
Method.
Background technology
Bio-based materials refer to renewable resource (such as crops, waste, trees, other plant and its residuum and interior
Inclusion etc.) it is raw material, the biomass synthetic material obtained by biosynthesis, biological processing, biorefinery process.Biological base material
Material includes the polymer materials monomer such as bio-alcohol, organic acid, alkane, alkene of biomass source.
Bio-based materials are the great industry directions that social economy's green increases.The large-scale development of bio-based materials with answer
With will reduce dependence of the chemical materials industry to fossil resource, and be conducive to enhancement of environment and Development of Economy.
Epoxy resin with its excellent electrical insulation capability, shrinking percentage is small, stability is good, mechanical property is good is widely used in electricity
The fields such as son, electrical, machine-building, chemical anticorrosion.Especially in paint field, epoxy resin has become coating with four big synthesis
One of resin.Since the organic solvent that traditional solvent based coating evaporates can cause atmosphere pollution, and health is made
At influence, therefore research and develop the common recognition that environment-friendlywater-based water-based paint has become coating circle.But major part epoxy resin is insoluble
Yu Shui directly cannot add water to be emulsified, can be modified to obtain to epoxy resin by chemic modified method at present aqueous
From dry epoxy-ester.
Invention content
For overcome the deficiencies in the prior art, the purpose of the present invention is to provide a kind of aqueous ring based on bio-based materials
Oxygen ester and preparation method thereof, main raw material use bio-based materials.
The purpose of the present invention adopts the following technical scheme that realization:
A kind of preparation method of the water-base epoxy ester based on bio-based materials, includes the following steps:
S1. by the gutter oil alcoholysis liquid of 15~25 parts by weight, the biology base succinic acid of 10~15 parts by weight, 5~10 mass
The polyester waste material of part, the biodiesel of 8~12 parts by weight refine glycerine mixing;
S2. after mixture reaction a period of time of heating stepses S1, the epoxy resin reaction one of 35~45 parts by weight is added
The section time;
S3. the trimellitic anhydride for 5~8 parts by weight being added into the product of step S2 is reacted, when the acid value of product is small
Cool down after 35;
S4. the butyl glycol ether of 25~35 parts by weight is added into the product of step S3;
S5. neutralizer is added into the product of step S4 into salt.
Further, step S2 includes the following steps:
S21. the mixture of heating stepses S1, in being warming up to 175~185 DEG C in 2~3 hours,;
S22. 210~230 DEG C are continuously heating to after keeping the temperature 50min~60min, the epoxy of 35~45 parts by weight is then added
Resin is reacted;
S23. cool down after the acid value of the product of step S22 is less than 10.
Further, step S3 includes step:
S31. when step S23 is cooled to 175~185 DEG C, the trimellitic anhydride of 5~8 parts by weight of addition, heat preservation 1.5~
2.5 hour;
S32. cool down after the product acid value of step S31 is less than 35.
Further, step S4 includes step:
S41. the butyl glycol ether of 25~35 parts by weight is added when step S3 is cooled to 145~155 DEG C;
S42. when the solid content of the product of step S41 reaches 70~80%, filtering is spare.
Further, in step S1, the gutter oil alcoholysis liquid is prepared by the following method:By the ground of 70~90 parts by weight
In ditch oil and the pentaerythrite of 10~20 parts by weight input reaction kettle, 170~190 DEG C are warming up to, catalyst is then added, is continued
260~280 DEG C are warming up to, reaction cools down spare after 1~3 hour.
Further, when preparing the gutter oil alcoholysis liquid, after catalyzer temperature-elevating reaction is added, when the gutter oil alcoholysis
Liquid is with ethyl alcohol with mass ratio 1:When 1 mixture being mixed to get is as clear as crystal, you can reaction was completed, and cooling is spare.
Further, the biology base succinic acid is prepared using microbial fermentation carbohydrate.
Further, the biodiesel is refined glycerine and is extracted from biodiesel.
Compared with prior art, the beneficial effects of the present invention are:Utilize bio-based materials (gutter oil, biology base succinic acid
And biodiesel refines glycerine) it is used as main raw material to prepare water-base epoxy ester, which can complete generation
For water-base epoxy ester in the prior art, the primer performance that the two is prepared is very nearly the same, it is seen that method provided by the invention
With good practicability;In addition, by introducing polyester waste material in formula, the cost of water-base epoxy ester is reduced, is conducive to
The popularization of the water-base epoxy ester of the present invention.
Specific implementation mode
In the following, in conjunction with specific implementation mode, the present invention is described further, it should be noted that is do not collided
Under the premise of, new embodiment can be formed between various embodiments described below or between each technical characteristic in any combination.
The present invention provides a kind of preparation method of the water-base epoxy ester based on bio-based materials, includes the original of following parts by weight
Material:
The gutter oil alcoholysis liquid is prepared by bio-based materials gutter oil, and polyalcohol can be obtained by alcoholysis in gutter oil
With the mixture of polyester.The raw material of the gutter oil alcoholysis liquid includes:The gutter oil of 70~90 parts by weight;10~20 parts by weight
Pentaerythrite;Suitable catalyst.Preferably, the catalyst in the gutter oil alcoholysis liquid is lithium hydroxide.
The gutter oil alcoholysis liquid is prepared by the following method:By in gutter oil and pentaerythrite input reaction kettle, heat up
To 170~190 DEG C, catalyst is then added, is continuously heating to 260~280 DEG C, reaction cools down spare after 1~3 hour.It obtains
The gutter oil alcoholysis liquid and ethyl alcohol with mass ratio 1:It is as clear as crystal when 1 mixing.In other words, when the gutter oil alcoholysis
Liquid is with ethyl alcohol with mass ratio 1:When 1 mixture being mixed to get is as clear as crystal, you can reaction was completed, and cooling is spare.
It is noted that the gutter oil is by pretreated refining gutter oil, pre-treatment step includes going to clean
Matter, centrifugation, alkali cleaning, refining.The pretreatment of gutter oil refers to the prior art, and the present invention is no longer described in detail.
Biology base succinic acid is different from the succinic acid of industrial chemical method production at present, mainly utilizes microbial fermentation
It is prepared by carbohydrate.Since biology base succinic acid is using renewable sugar source and carbon dioxide as primary raw material, micro- life
Object fermentation method production succinic acid has the advantages that at low cost and breaks away to petrochemical material dependence, and opens greenhouse gases dioxy
Change the new way that carbon utilizes.The preparation method of biology base succinic acid refers to the prior art, and the present invention is no longer described in detail.
It is the main by-product of biodiesel that the biodiesel, which refines glycerine, and glycerine is extracted from biological diesel oil byproduct
Method include pretreatment process and rectification under vacuum process.Specific extraction process refers to the prior art, and the present invention is no longer described in detail.
The gutter oil alcoholysis liquid, biology base succinic acid, biodiesel refine glycerine and polycondensation reaction occur, and obtain compared with high score
The main chain of son amount, after epoxy resin is added, epoxy ring-opening is grafted on main chain, to obtain epoxy-ester, is then added partially
Benzenetricarboxylic anhydride is reacted, and hydrophilic group is introduced on epoxy-ester main chain, modified epoxy ester is obtained, is eventually adding neutralizer
At obtaining water-base epoxy ester after salt.
The addition of the polyester waste material, can't reduce the correlated performance of epoxy-ester, and main function is to reduce epoxy-ester
Cost.With the development of polyester industrial, China has a large amount of polyester waste material to generate every year, prepares and sets currently with polyester waste material
The research of fat has very much.Document " using terylene waste material synthesize unsaturated polyester resin research " ("Environmental project"2002 8
The 4th phase of volume 20 moon) in, disclose the method for preparing unsaturated polyester (UP) using terylene waste material." papermaking, terylene are utilized in document
Waste material prepares alkyd resin " ("Shanghai coating"The 6th phase of volume 51 in June, 2013) in, it discloses and prepares alcohol using terylene waste material
The method of acid resin.But in the prior art, research, present invention research are had no to application of the polyester waste material in water-base epoxy ester
Application of the polyester waste material in water-base epoxy ester while not reducing water-base epoxy ester performance reduces water-base epoxy ester
Cost.
The preparation method of the water-base epoxy ester based on bio-based materials includes the following steps:
S1. by the gutter oil alcoholysis liquid of 15~25 parts by weight, the biology base succinic acid of 10~15 parts by weight, 5~10 mass
The polyester waste material of part, the biodiesel of 8~12 parts by weight refine glycerine mixing;
S2. after mixture reaction a period of time of heating stepses S1, the epoxy resin of 35~45 parts by weight, the ring is added
Ring-opening reaction occurs for the epoxy group of oxygen resin;
S3. the trimellitic anhydride for 5~8 parts by weight being added into the product of step S2 is reacted, when the acid value of product is small
Cool down after 35;
S4. the butyl glycol ether of 25~35 parts by weight is added into the product of step S3;
S5. the neutralizer of 3~4 mass parts is added into the product of step S4 into salt, adds water and is quickly dispersed with stirring, obtain
To water-base epoxy ester composition.
Preferably, step S2 includes the following steps:
S21. the mixture of heating stepses S1, in being warming up to 175~185 DEG C in 2~3 hours,;
S22. 210~230 DEG C are continuously heating to after keeping the temperature 50min~60min, the epoxy of 35~45 parts by weight is then added
Ring-opening reaction occurs for the epoxy group of resin, the epoxy resin, is grafted on matrix resin segment;
S23. cool down after the acid value of the product of step S22 is less than 10.
Preferably, step S3 includes step:
S31. when step S2 is cooled to 175~185 DEG C, the trimellitic anhydride of 5~8 parts by weight is added, keeps the temperature 2 hours;
S32. cool down after the product acid value of step S31 is less than 35.
Preferably, step S4 includes step:
S41. the butyl glycol ether of 25~35 parts by weight is added when step S3 is cooled to 145~155 DEG C;
S42. when the solid content of the product of step S41 reaches 70~80, filtering is spare.
Preferably, the neutralizer is selected from triethylamine, ammonium hydroxide or dimethylethanolamine.
In following embodiment, gutter oil with being purchased from Zhejiang green grass Pty Ltd is refined.Wherein biology base succinic acid, life
Object diesel oil refines glycerine, polyester waste material is commercially available, and it is crude glycerine that the biodiesel, which refines glycerine, and it is relatively low to refine cost.
[Embodiment 1]
It is prepared by gutter oil alcoholysis liquid:The pentaerythrite of the refining gutter oil of 85 mass parts, 15 mass parts is put into reaction kettle
In, 180 DEG C are warming up to, the lithium hydroxide of 0.03 mass parts is then added, is continuously heating to 270 DEG C, is reacted 2 hours or so, when
Reaction product is with ethyl alcohol with mass ratio 1:When 1 mixture being mixed to get is as clear as crystal, you can reaction was completed, and cooling is spare.
[Embodiment 2]
A kind of water-base epoxy ester based on bio-based materials, is prepared by following steps:
By the gutter oil alcoholysis liquid of 15 parts by weight, terylene waste material, 8 weights of the biology base succinic acid of 10 parts by weight, 5 mass parts
The biodiesel for measuring part refines glycerine mixing;It is slowly warming up to 180 DEG C in 3h, 220 DEG C are continuously heating to after keeping the temperature 1h, then adds
Enter the epoxy resin 601 of 35 parts by weight, keep epoxy ring-opening, measures after acid value is less than 10 and cool down;It is added when being cooled to 180 DEG C
The trimellitic anhydride of 5 parts by weight, heat preservation 2h or so are measured after acid value is less than 35 and are cooled down;25~35 weights are added after being cooled to 150 DEG C
Measure the butyl glycol ether of part so that the solid content of product is 75 ± 1, is then filtered spare.
3 parts by weight neutralizers (triethylamine) are added in the modified epoxy ester being prepared to embodiment 2 into salt, are then added
Water is quickly dispersed with stirring, and obtains water-base epoxy ester composition.
[Embodiment 3]
A kind of water-base epoxy ester based on bio-based materials, is prepared by following steps:
By the gutter oil alcoholysis liquid of 25 parts by weight, the biology base succinic acid of 15 parts by weight, the terylene waste material of 10 mass parts, 12
The biodiesel of parts by weight refines glycerine mixing;It is slowly warming up to 180 DEG C in 3h, is continuously heating to 220 DEG C after keeping the temperature 1h, then
The epoxy resin 601 of 45 parts by weight is added, keeps epoxy ring-opening, measures after acid value is less than 10 and cools down;Add when being cooled to 180 DEG C
Enter the trimellitic anhydride of 8 parts by weight, heat preservation 2h or so, measures after acid value is less than 35 and cool down;25~35 are added after being cooled to 150 DEG C
The butyl glycol ether of parts by weight so that the solid content of product is 75 ± 1, is then filtered spare.
The neutralizer (triethylamine) of 4 parts by weight is added in the modified epoxy ester being prepared to embodiment 3 into salt, then adds
Enter water to be quickly dispersed with stirring, obtains water-base epoxy ester composition.
[Embodiment 4]
A kind of water-base epoxy ester based on bio-based materials, is prepared by following steps:
The biodiesel of the gutter oil alcoholysis liquid of 25 parts by weight, the biology base succinic acid of 15 parts by weight, 12 parts by weight is carried
Refine glycerine mixing;It is slowly warming up to 180 DEG C in 3h, is continuously heating to 220 DEG C after keeping the temperature 1h, the epoxy of 45 parts by weight is then added
Resin 601 keeps epoxy ring-opening, measures after acid value is less than 10 and cools down;The inclined benzene three of 8 parts by weight is added when being cooled to 180 DEG C
Acid anhydrides, heat preservation 2h or so are measured after acid value is less than 35 and are cooled down;It is cooled to the ethylene glycol fourth that 25~35 parts by weight are added after 150 DEG C
Ether so that the solid content of product is 75 ± 1, is then filtered spare.
The neutralizer (triethylamine) of 4 parts by weight is added in the modified epoxy ester being prepared to embodiment 4 into salt, then adds
Enter water to be quickly dispersed with stirring, obtains water-base epoxy ester composition.
[Comparative example 1]
A kind of preparation method of water-base epoxy ester is provided:
By 29 parts of linolenic acids, 14 parts of epoxy resin E-20,10 parts of epoxy resin E-03,6 parts of benzoic acid, 3 parts of phthalic anhydrides,
0.2 part of antioxidant is added in reaction kettle successively, by the temperature of reaction kettle from room temperature to 120 DEG C;
The agitating device for opening reaction kettle is stirred, and temperature is warming up to 160 DEG C, and then heat preservation carries out first time esterification
Reaction, 1 hour reaction time;
Continue temperature being warming up to 180 DEG C, then heat preservation carries out second of esterification, 1 hour reaction time;
Continue temperature being warming up to 240 DEG C, then heat preservation carries out third time esterification, 3.5 hours reaction time;
Temperature in reaction kettle is down to 120 DEG C by the cooling system opened in reaction kettle, and 19.5 parts of butyl glycol ethers are added,
It stirs evenly.
The neutralizer (triethylamine) of 3 parts by weight is added in the modified epoxy ester being prepared to comparative example 1 into salt, then adds
Enter water to be quickly dispersed with stirring, obtains water-base epoxy ester composition.
Table 1 lists the test result of the correlated performance of each group water-base epoxy ester, can be seen that from the test result of table 1
The water-base epoxy ester system that the present invention is prepared can replace water-base epoxy ester in the prior art substantially, what the two was prepared
Primer performance is very nearly the same.
Table 1
Comparative example 2,3 and embodiment 4, it can be found that the addition of terylene waste material does not reduce the property of water-base epoxy ester
Can, but the water-base epoxy ester of same quality, added terylene waste material than not plus there are many cost reduction of terylene waste material, because
This, the cost of water-base epoxy ester can be reduced by adding the terylene waste material of certain mass, but will not to the performance of water-base epoxy ester
Generate apparent influence.
The above embodiment is only the preferred embodiment of the present invention, and the scope of protection of the present invention is not limited thereto,
The variation and replacement for any unsubstantiality that those skilled in the art is done on the basis of the present invention belong to institute of the present invention
Claimed range.
Claims (9)
1. a kind of preparation method of the water-base epoxy ester based on bio-based materials, which is characterized in that include the following steps:
S1. by the gutter oil alcoholysis liquid of 15~25 parts by weight, the biology base succinic acid of 10~15 parts by weight, 5~10 mass parts
The biodiesel refinement glycerine mixing of polyester waste material, 8~12 parts by weight;
S2. after mixture reaction a period of time of heating stepses S1, when the epoxy resin of 35~45 parts by weight of addition reacts one section
Between;
S3. the trimellitic anhydride for 5~8 parts by weight being added into the product of step S2 is reacted, when the acid value of product is less than 35
After cool down;
S4. the butyl glycol ether of 25~35 parts by weight is added into the product of step S3;
S5. the neutralizer of 3~4 parts by weight is added into the product of step S4 into salt.
2. according to the method described in claim 1, it is characterized in that, step S2 includes the following steps:
S21. the mixture of heating stepses S1, in being warming up to 175~185 DEG C in 2~3 hours,;
S22. 210~230 DEG C are continuously heating to after keeping the temperature 50min~60min, the epoxy resin of 35~45 parts by weight is then added
It is reacted;
S23. cool down after the acid value of the product of step S22 is less than 10.
3. according to the method described in claim 2, it is characterized in that, step S3 includes step:
S31. when step S23 is cooled to 175~185 DEG C, the trimellitic anhydride of 5~8 parts by weight is added, heat preservation 1.5~2.5 is small
When;
S32. cool down after the product acid value of step S31 is less than 35.
4. according to the method described in claim 3, it is characterized in that, step S4 includes step:
S41. the butyl glycol ether of 25~35 parts by weight is added when step S3 is cooled to 145~155 DEG C;
S42. when the solid content of the product of step S41 reaches 70~80%, filtering is spare.
5. according to any methods of claim 1-4, which is characterized in that in step S1, the gutter oil alcoholysis liquid passes through
It is prepared by following methods:By in the gutter oil of 70~90 parts by weight and the pentaerythrite of 10~20 parts by weight input reaction kettle, heat up
To 170~190 DEG C, catalyst is then added, is continuously heating to 260~280 DEG C, reaction cools down spare after 1~3 hour.
6. according to the method described in claim 5, it is characterized in that, when preparing the gutter oil alcoholysis liquid, catalyst liter is added
After temperature reaction, when the gutter oil alcoholysis liquid and ethyl alcohol are with mass ratio 1:When 1 mixture being mixed to get is as clear as crystal, you can
Reaction was completed, and cooling is spare.
7. according to any methods of claim 1-4, which is characterized in that the biology base succinic acid is sent out using microorganism
Ferment carbohydrate is prepared.
8. according to any methods of claim 1-4, which is characterized in that the biodiesel refines glycerine from biodiesel
Middle extraction.
9. a kind of water-base epoxy ester based on bio-based materials being prepared using any methods of claim 1-8.
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| CN108690466B (en) | 2020-07-24 |
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