CN106188514B - A kind of aqueous tall oil alkyd resin lotion and preparation method thereof - Google Patents
A kind of aqueous tall oil alkyd resin lotion and preparation method thereof Download PDFInfo
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- CN106188514B CN106188514B CN201610585763.6A CN201610585763A CN106188514B CN 106188514 B CN106188514 B CN 106188514B CN 201610585763 A CN201610585763 A CN 201610585763A CN 106188514 B CN106188514 B CN 106188514B
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
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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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
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Abstract
A kind of aqueous tall oil alkyd resin lotion and preparation method thereof, it is raw material which, which selects the tall oil extracted in papermaking wastewater, and preparation process includes：(1) it is reacted with diethanol amine using tall oil, tall oil diglycollic amide is made；(2) tall oil diglycollic amide and the binary acid with sulfonic acid group is used to prepare intermediate polyester with diol reaction；(3) intermediate polyester, vegetable oil, aliphatic acid, polyalcohol, polyacid are reacted, then plus deionized water is disperseed, and prepares alkyd resin aqueous dispersion；The present invention is not only effectively utilized the tall oil extracted from papermaking wastewater, but also has widened the application field of tall oil.
Description
Technical field
The invention belongs to chemical material fields, and in particular to arrive a kind of aqueous tall oil alkyd resin lotion and its preparation side
Method
Background technology
Traditional solvent based coating is big to the use of organic solvent, and environmental pollution is serious, and to the consumption of oil
Greatly, with high costs, the gas of discharge is harmful；Nearly ten years, it is applied as the performance of water paint gradually catch up with solvent type
Material, is growing in the application of paint field, gradually instead of many usual solvent based coatings.As various countries are to volatility
The limitation of organic compound is increasingly stringenter, and resin, formula optimization and be applicable in the exploitation of auxiliary agent, water paint is in metal
Antirusting paint, home decoration coating, building coating the market share will be continuously improved, fatting agent occupies in process hides chemical products
Very important status.
Ester group there are many containing on the condensation polymer macromolecular main chain that polyalcohol and polyacid are generated by polycondensation reaction, it is this
Polymer is known as polyester, and the polyester resin of aliphatic acid or oil modification is known as alkyd resin.
Invention content
In order to solve the above technical problems, the purpose of the present invention is to provide a kind of aqueous tall oil alkyd resin lotion and
Preparation method can enrich the type of alkyd resin, have the characteristics that paint film adhesion is good, bright, richness is high.
To achieve the goals above, the technical solution adopted by the present invention is：
A kind of aqueous tall oil alkyd resin lotion, be solid content be 30wt%~60wt%, viscosity be 600mPas~
The alkide resin emulsion of 2000mPas.
A kind of preparation method of aqueous tall oil alkyd resin lotion, includes the following steps：
Step (1)：Prepare tall oil diethanol amine；
Tall oil is weighed in reaction bulb, inert gas shielding is heated to 140~160 DEG C, then press diethanol amine with it is appropriate
That molar equivalent 1:1~1:2 ratio, diethanol amine, which is added, makes it be reacted with tall oil, obtained product at reduced pressure distillation
Except the water generated in dereaction, tall oil diethanol amine is made；
Step (2)：Prepare intermediate polyester；
By the tall oil diethanol amine obtained in dicarboxylic acids and step (1) with sulfonate groups, a certain amount of two
First alcohol, deionized water and acid catalyst are added in reaction vessel, are passed through nitrogen heating reaction, reaction temperature is 140~200
DEG C, intermediate polyester was made in 5~10 hours reaction time；
Step (3)：Prepare alkyd resin aqueous dispersion；
In the reactor by mass fraction be added 30~40 parts of the intermediate polyester obtained in step (2), vegetable oil 20~
10~20 parts of 30 parts, 10~20 parts of polyalcohol, polyacid or acid anhydrides and 0.01~0.05 part of acid catalyst lead to nitrogen temperature, control
Reaction temperature processed is reacted 6~10 hours at 120 DEG C~230 DEG C, until acid value is down to 10mgKOH/g hereinafter, stopping reaction；So
Cooling discharge afterwards obtains tall oil alkyd resin；Deionized water is added in tall oil alkyd resin, high-speed stirred obtains solid content and is
30wt%~60wt% tall oil alkyd resin lotions.
Glycol in the step (2) in tall oil diglycollic amide, dihydric alcohol, with the binary carboxylic with sulfonic acid group
The molar ratio of acid is 2~5:1, deionized water dosage is 10wt%~20wt% of reaction raw materials gross mass, the amount of acid catalyst
For 0.05wt%~0.1wt% of reaction raw materials gross mass；The gross mass of the reaction raw materials is the gross mass of alcohol and acid.
Tall oil diglycollic amide is made described in the step (1), diethanol amine or triethanolamine and tall oil may be used
Oil reaction.The ester that a small amount of ester is generated, but generated is had in the reaction process influences less aqueous alkide resin performance；Because
Alkyd resin is mainly that the polyester formed by polyalcohol and polyacid does not have polyester product so the reaction generates a small amount of ester
There is negative effect.
Dicarboxylic acids with sulfonate groups described in the step (2) is M-phthalic acid, terephthalic acid (TPA), dicarboxyl
Base naphthalene or diphenyldicarboxylic acid；Acid catalyst in the step (2) is dibutyl tin dilaurate.
Dihydric alcohol described in the step (2) is ethylene glycol, propylene glycol, pentanediol, butanediol.
The one kind of acid catalyst in following organic tin compound described in the step (2) and step (3)：
Mono-n-butyltin, Dibutyltin oxide, Dibutyltin oxide chloride, dibutyl tin dilaurate, dibutyl tin acetate
Or monobutyl-tin-trichloride.
Polyacid or acid anhydrides described in the step (3) are one or both of following polyacid or acid anhydrides：It is adjacent
Phthalate anhydride, phthalic acid, M-phthalic acid, trimellitic anhydride, terephthalic acid (TPA), adipic acid, maleic acid are suitable
Anhydride maleique；The polyalcohol is one or both of following polyalcohol：Pentaerythrite, trimethylolpropane, glycerine
And trimethylolethane.
Vegetable oil described in the step (3) is tall oil, linseed oil, soya-bean oil.
Beneficial effects of the present invention：
The present invention greatly reduces the use to organic solvent, when not only having complied with compared to traditional solvent based coating
Requirement of the generation to environmental protection, and the consumption to oil is further reduced, cost is both saved, and reduce because a large amount of
Injury of the discharge of VOCs to human body；The present invention is effectively utilized the tall oil extracted from papermaking wastewater, but also widens
The application field of tall oil；The present invention has the characteristics that paint film adhesion is good, bright, richness is high, and monomer abundance,
Price is low, wide in variety, formula variation is big, simple for process, facilitates chemical modification and has good application property, comprehensive performance excellent
It is different, meet the requirement of social sustainable development.
Specific implementation mode
The present invention is described in further details with reference to embodiment.
Embodiment one
A kind of preparation method of aqueous tall oil alkyd resin lotion, includes the following steps：
Step 1：Prepare tall oil diethanol amine；
Tall oil is weighed in reaction bulb, inert gas shielding is heated to 160 DEG C, then presses diethanol amine and tall oil
Molar ratio 1:1 ratio, diethanol amine, which is added, makes it be reacted with tall oil, and product at reduced pressure is distilled off in reaction and generates
Tall oil diethanol amine is made in water；
Step 2：Prepare intermediate polyester；
By the tall oil diethanol amine obtained in 5-sodium sulfo isophthalate, step 1, ethylene glycol, deionized water and
Dibutyl tin dilaurate is added in reaction vessel, is passed through nitrogen heating reaction, 200 DEG C of reaction temperature, the reaction time 6.5 is small
When, intermediate polyester is made；
The dicarboxylic acids molar ratio of glycol and 5-sodium sulfo isophthalate in tall oil diglycollic amide and ethylene glycol
It is 3:1, deionized water dosage is the 10wt% of reaction raw materials gross mass, and the amount of acid catalyst dibutyl tin dilaurate is reaction
The 0.05wt% of raw material gross mass；The gross mass of the reaction raw materials is the gross mass of alcohol and acid；
Step 3：Prepare alkyd resin aqueous dispersion；
30 parts of 40 parts of intermediate polyester, linseed oil, three hydroxyls obtained in step 2 are added by mass fraction in the reactor
0.01 part of 10 parts of methylpropane, 20 parts of phthalic anhydride and dibutyl tin dilaurate lead to nitrogen temperature, controlling reaction temperature
It at 160 DEG C, reacts 6 hours, until acid value is down to 10mgKOH/g hereinafter, stopping reaction；Then cooling discharge obtains tall oil oleyl alcohol
Acid resin；Deionized water is added in above-mentioned alkyd resin, high-speed stirred obtains the alkide resin emulsion that solid content is 50wt%.
Embodiment two
A kind of preparation method of aqueous tall oil alkyd resin lotion, includes the following steps：
Step 1：Prepare tall oil diethanol amine；
Tall oil is weighed in reaction bulb, inert gas shielding is heated to 150 DEG C, then presses diethanol amine and tall oil
Molar ratio 1:1.5 ratio, diethanol amine, which is added, makes it be reacted with tall oil, and product at reduced pressure is distilled off in reaction and generates
Water, tall oil diethanol amine is made；
Step 2：Prepare intermediate polyester；
By the tall oil diethanol amine obtained in 5-sodium sulfo isophthalate, step 1, a certain amount of pentanediol, go
Ionized water and dibutyl tin dilaurate are added in reaction vessel, are passed through nitrogen heating reaction, reaction temperature is at 170 DEG C, instead
7 hours between seasonable, intermediate polyester is made；
The dicarboxylic acids molar ratio of glycol and 5-sodium sulfo isophthalate in tall oil diglycollic amide and pentanediol
It is 3:1, deionized water dosage is the 15wt% that deionized water dosage is reaction raw materials gross mass, acid catalyst dibutyl tin osmanthus
The amount of sour tin is the 0.08wt% of reaction raw materials gross mass；The gross mass of the reaction raw materials is the gross mass of alcohol and acid；
Step 3：Prepare alkyd resin aqueous dispersion；
35 parts of intermediate polyester, soya-bean oil 25, the pentaerythrite obtained in step 2 is added by mass fraction in the reactor
0.05 part of 20 parts, 20 parts of maleic anhydride and acid catalyst lead to nitrogen temperature, and for controlling reaction temperature at 200 DEG C, reaction 6 is small
When, until acid value is down to 10mgKOH/g hereinafter, stopping reaction；Then cooling discharge obtains tall oil alkyd resin；By above-mentioned alcohol
Deionized water is added in acid resin, and high-speed stirred obtains the alkide resin emulsion that solid content is 60wt%.
Embodiment three
A kind of preparation method of aqueous tall oil alkyd resin lotion, includes the following steps：
Step 1：Prepare tall oil diethanol amine；
Tall oil is weighed in reaction bulb, inert gas shielding is heated to 140 DEG C, then presses diethanol amine and tall oil
Molar ratio 1:1.25 ratio, diethanol amine, which is added, makes it be reacted with tall oil, and product at reduced pressure is distilled off raw in reaction
At water, tall oil diethanol amine is made；
Step 2：Prepare intermediate polyester；
By the tall oil diethanol amine obtained in terephthaldehyde's disulfonate acid, step 1, ethylene glycol, deionized water and two fourths
Base tin dilaurate tin is added in reaction vessel, is passed through nitrogen heating reaction, 180 DEG C of reaction temperature, 5 hours reaction time, system
Obtain intermediate polyester；
The dicarboxylic acids molar ratio of glycol and terephthaldehyde's disulfonate acid in tall oil diglycollic amide and ethylene glycol is
3:1, deionized water dosage is the 15wt% that deionized water dosage is reaction raw materials gross mass, acid catalyst dibutyl tin cinnamic acid
The amount of tin is the 0.1wt% of reaction raw materials gross mass；
Step 3：Prepare alkyd resin aqueous dispersion；
30 parts of 40 parts of intermediate polyester, tall oil, three hydroxyls obtained in step 2 are added by mass fraction in the reactor
0.01 part of 10 parts of methylpropane, 20 parts of phthalic anhydride and dibutyl tin dilaurate lead to nitrogen temperature, controlling reaction temperature
It at 160 DEG C, reacts 6 hours, until acid value is down to 10mgKOH/g hereinafter, stopping reaction；Then cooling discharge obtains tall oil oleyl alcohol
Acid resin；Deionized water is added in above-mentioned alkyd resin, high-speed stirred obtains the alkide resin emulsion that solid content is 50wt%.
Example IV
A kind of preparation method of aqueous tall oil alkyd resin lotion, includes the following steps：
Step 1：Prepare tall oil diethanol amine；
Tall oil is weighed in reaction bulb, inert gas shielding is heated to 165 DEG C, then presses diethanol amine and tall oil
Molar ratio 1:1.5 ratio, diethanol amine, which is added, makes it be reacted with tall oil, and product at reduced pressure is distilled off in reaction and generates
Water, tall oil diethanol amine is made；
Step 2：Prepare intermediate polyester；
By the tall oil diethanol amine obtained in diphenyldicarboxylic acid sodium sulfonate, step 1, ethylene glycol, deionized water and two
Butyl tin dilaurate tin is added in reaction vessel, is passed through nitrogen heating and is reacted, 140 DEG C of reaction temperature, 10 hours reaction time,
Intermediate polyester is made；
The dicarboxylic acids molar ratio of glycol and diphenyldicarboxylic acid sodium sulfonate in tall oil diglycollic amide and ethylene glycol
It is 3:1, deionized water dosage is the 20wt% that deionized water dosage is reaction raw materials gross mass, acid catalyst dibutyl tin osmanthus
The amount of sour tin is the 0.1wt% of reaction raw materials gross mass；The gross mass of the reaction raw materials is the gross mass of alcohol and acid；
Step 3：Prepare alkyd resin aqueous dispersion；
40 parts of 30 parts of intermediate polyester, linseed oil, three hydroxyls obtained in step 2 are added by mass fraction in the reactor
0.02 part of 10 parts of methylpropane, 20 parts of phthalic anhydride and dibutyl tin dilaurate lead to nitrogen temperature, controlling reaction temperature
It at 150 DEG C, reacts 6 hours, until acid value is down to 10mgKOH/g hereinafter, stopping reaction；Then cooling discharge obtains tall oil oleyl alcohol
Acid resin；Deionized water is added in above-mentioned alkyd resin, high-speed stirred obtains the alkide resin emulsion that solid content is 60wt%.
Claims (7)
1. a kind of preparation method of aqueous tall oil alkyd resin lotion, which is characterized in that include the following steps：
Step (1)：Prepare tall oil diglycollic amide；
Tall oil is weighed in reaction bulb, inert gas shielding is heated to 140~160 DEG C, then presses diethanol amine and tall oil
Molar ratio 1:1~1:2 ratio, diethanol amine, which is added, makes it be reacted with tall oil, and obtained product at reduced pressure is distilled off
Tall oil diglycollic amide is made in the water generated in reaction；
Step (2)：Prepare intermediate polyester；
By the tall oil diglycollic amide obtained in dicarboxylic acids and step (1) with sulfonate groups, a certain amount of binary
Alcohol, deionized water and acid catalyst are added in reaction vessel, be passed through nitrogen heating reaction, reaction temperature at 140~200 DEG C,
Intermediate polyester was made in 5~10 hours reaction time；
Step (3)：Prepare alkyd resin aqueous dispersion；
In the reactor by mass fraction be added 20~30 parts of 30~40 parts of intermediate polyester, the vegetable oil obtained in step (2),
10~20 parts of 10~20 parts of polyalcohol, polyacid or acid anhydrides and 0.01~0.05 part of acid catalyst lead to nitrogen temperature, control reaction
Temperature is reacted 6~10 hours at 120 DEG C~230 DEG C, until acid value is down to 10mgKOH/g hereinafter, stopping reaction；Then cool down
Discharging, obtains tall oil alkyd resin；Deionized water is added in tall oil alkyd resin, it is 30wt% that high-speed stirred, which obtains solid content,
~60wt%, viscosity are the tall oil alkyd resin lotion of 600mPas~2000mPas.
2. a kind of preparation method of aqueous tall oil alkyd resin lotion according to claim 1, which is characterized in that step
(2) molar ratio of the glycol in tall oil diglycollic amide, dihydric alcohol and the dicarboxylic acids with sulfonic acid group is 2~5:1,
Deionized water dosage is 10wt%~20wt% of reaction raw materials gross mass, and the amount of acid catalyst is reaction raw materials gross mass
0.05wt%~0.1wt%；The gross mass of the reaction raw materials is the gross mass of alcohol and acid.
3. a kind of preparation method of aqueous tall oil alkyd resin lotion according to claim 1, which is characterized in that the step
Suddenly the dicarboxylic acids with sulfonate groups is M-phthalic acid, terephthalic acid (TPA), dicarboxyl naphthalene or diphenyl dicarboxyl in (2)
Acid；Acid catalyst in the step (2) is dibutyl tin dilaurate.
4. a kind of preparation method of aqueous tall oil alkyd resin lotion according to claim 1, which is characterized in that the step
Suddenly dihydric alcohol is that ethylene glycol, propylene glycol, pentanediol, butanediol are one such in (2).
5. a kind of preparation method of aqueous tall oil alkyd resin lotion according to claim 1, which is characterized in that step
(2) and one kind in following organic tin compound of the acid catalyst in step (3)：Mono-n-butyltin, dibutyl oxygen
Change tin, Dibutyltin oxide chloride, dibutyl tin dilaurate, dibutyl tin acetate or monobutyl-tin-trichloride.
6. the preparation method of aqueous tall oil alkyd resin lotion according to claim 1, which is characterized in that the step
(3) polyacid or acid anhydrides are one or both of following polyacid or acid anhydrides in：Phthalic anhydride, phthalic acid,
Phthalic acid, trimellitic anhydride, terephthalic acid (TPA), adipic acid, maleic acid, maleic anhydride；The polyalcohol is
One or both of following polyalcohol：Pentaerythrite, trimethylolpropane, glycerine and trimethylolethane.
7. the preparation method of aqueous tall oil alkyd resin lotion according to claim 1, which is characterized in that the step
(3) vegetable oil is one kind in tall oil, linseed oil, soya-bean oil in.
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| CN107459633A (en) * | 2017-08-22 | 2017-12-12 | 太仓市芸芸化纤有限公司 | The synthesis technique of aqueous alkide resin |
| CN112143363A (en) * | 2019-06-28 | 2020-12-29 | 广东顺德三和化工有限公司 | Low-odor, high-fullness and smooth polyurethane varnish and preparation method thereof |
| CN116970319B (en) * | 2023-04-15 | 2024-05-17 | 千浪化研新材料(上海)有限公司 | Environment-friendly water-based UV quick-drying coating and preparation method thereof |
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| CN105601898B (en) * | 2015-12-30 | 2018-08-24 | 帝斯曼先达合成树脂(佛山)有限公司 | A kind of water soluble alkyd resin and preparation method thereof with antiseptic property |
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