CN108203555A - A kind of synthetic method of beta-hydroxy alkylamide - Google Patents
A kind of synthetic method of beta-hydroxy alkylamide Download PDFInfo
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- CN108203555A CN108203555A CN201711487423.0A CN201711487423A CN108203555A CN 108203555 A CN108203555 A CN 108203555A CN 201711487423 A CN201711487423 A CN 201711487423A CN 108203555 A CN108203555 A CN 108203555A
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- reaction
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- synthetic method
- hydroxy alkylamide
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
- C09D5/037—Rheology improving agents, e.g. flow control agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of synthetic methods of β hydroxyalkyl amides, rilanit special is added in into reaction system after the completion of reaction, products obtained therefrom is applied in powder coating formulation, it can reach and improve powdery paints coating gloss, flow leveling, the advantageous effect of pin hole is reduced, while does not influence original curing performance.
Description
Technical field
The present invention relates to the field of chemical synthesis, the synthetic method of specifically a kind of beta-hydroxy alkylamide.
Background technology
As requirement of the people to health environment-friendly is higher and higher, although traditional carboxyl polyester/TGIC systems are uniform, steady
It is fixed, adjustable, have good heat-resisting and weather resistance, can substantially meet user requirement, but its strong skin irritation and
Potential carcinogenicity to withdraw from the market as inevitable.HAA types (hydroxyalkyl amide) compound is generally acknowledged low toxic and environment-friendly type
Object is closed, has been widely used in daily use chemicals, surfactant and paint field, particularly art of powder coatings is as polyester coating
Curing agent, it is strong with reactivity, it is good suitable for low temperature curing conditions, storage characteristics.
The existing HAA products of existing market are in powdery paints in application, tending to pin hole, orange peel, gloss occur poor
The problems such as, seriously affect the aesthetics of its film.What is taken in the prior art is that leveling auxiliary agent is added in powder coating formulation
To solve problems, but the addition of levelling agent can reduce depositing for powdery paints while powdery paints coating levelling is improved
Store up stability.
Invention content
In order to solve the above problem, the invention discloses a kind of β-hydroxyls for enhancing powdery paints flow leveling, improving gloss
The synthetic method of alkylamide.
The purpose of the present invention can be achieved through the following technical solutions：
A kind of synthetic method of beta-hydroxy alkylamide, includes the following steps：
(1) by β-alkanolamine and basic catalyst input reaction kettle, 80-100 is heated under the protection of inert gas
DEG C, after pressure reaches 0.03-0.05MPa in the gas to kettle in extraction kettle, alkyl carboxylates were added dropwise in 1-3 hours, and constantly
Stirring carries out ammonolysis reaction, while persistently steams the alcohol released in reaction process；
(2) alkyl carboxylates drop finishes, and continues to keep the temperature ammonolysis reaction under 0.03-0.05MPa after 0.5-2 hours, adjusts kettle
Interior pressure is normal pressure, and the aqueous solution of phosphoric acid or phosphorous acid is added in into reaction mixture, is thoroughly mixed；
(3) rilanit special is added in into reaction system, reaction system is warming up to 110-150 DEG C and is kept the temperature, by anti-
The gas dispersion apparatus in bottom portion inert gas of the charged pressure not less than 0.1MPa into reaction system is answered to carry out bubbling purging,
Stop inflation after persistently inflating 2-10min, be evaporated under reduced pressure to kettle and force down in 0.005MPa, continue to vacuumize 5-20min, Ran Houting
It only vacuumizes, is re-filled with inert gas and carries out bubbling purging, stop inflation and be evaporated under reduced pressure, such alternate intervals are inflated
With vacuum distillation 2-5 times, until no liquid substance steams；
(4) remaining reaction product is cooled to 90-100 DEG C after steaming liquid substance, then blowing is cooled down, crushed, i.e.,
Obtain white powder product.
Preferably, the alkyl carboxylates and the molar ratio of β-alkanolamine are 1:2-2.1.
Preferably, the alkyl carboxylates and the mass ratio of basic catalyst are 1:0.00001-0.05.
Preferably, phosphoric acid or the minimum molar ratio 1 for its hydrogen ion and hydroxide ion in basic catalyst of phosphorous acid:
1-1.2, maximum are that the molar ratio of its hydroxyl and hydroxyl in β-alkanolamine is 1:8.
Preferably, the phosphoric acid or the concentration of aqueous solution of phosphorous acid are 20-50wt%.
Preferably, the rilanit special dosage is the 8-50% of β-alkanolamine.
Beneficial effects of the present invention：
The present invention is applied by adding in rilanit special, products obtained therefrom into reaction system after the completion of reaction applied to powder
In material formula, it can reach and improve powdery paints coating gloss, flow leveling, reduce the advantageous effect of pin hole, while do not influence original
Some anti-yellowing properties and storage stability.
Specific embodiment
The technical solution in the embodiment of the present invention will be clearly and completely described below, it is clear that described implementation
Example is only part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
All other embodiment that technical staff is obtained without creative efforts belongs to the model that the present invention protects
It encloses.
Embodiment 1
210.0g (2mol) diethanol amine and 2.8g sodium methoxides mixture input bottom are had to the reaction of gas dispersion apparatus
In kettle, it is heated to 100 DEG C under nitrogen protection.After pressure reaches 0.05MPa in extraction gas reactor to kettle, it is added dropwise in 2h
174.0g (1mol) dimethyl adipate, is stirred continuously reaction, and synchronize the methanol for steaming and being released in reaction process.Using 2h
After reaction, 8g20% phosphate aqueous solutions are added in into reaction mixture, rilanit special 17.6g is added in after being thoroughly mixed,
Reaction system is warming up to 150 DEG C and is kept the temperature, 5min is continued with 0.5MPa pressure by the gas dispersion apparatus of reactor bottom
Nitrogen bubbling is filled with into reaction system and is stirred continuously, then stops logical nitrogen, decompression steams liquid substance to kettle pressure and reaches
0.003MPa simultaneously continues to vacuumize 15min, and stopping vacuumizes is filled with nitrogen 3min by preceding method again, then stop inflation again into
Row vacuum distillation, so operates 3 times, then no liquid substance steams repeatedly, and reaction system is cooled to 90 DEG C, blowing, further
It is crushed after cooling, obtains white of the invention and flow freely shape product.
Embodiment 2
210.0g (2.0mol) diethanol amine and 2.8g sodium methoxides mixture input bottom there is into the anti-of gas dispersion apparatus
It answers in kettle, is heated to 80 DEG C under nitrogen protection.After pressure reaches 0.05MPa in extraction gas reactor to kettle, it is added dropwise in 2h
174.0g (1mol) dimethyl adipate, is stirred continuously reaction, and synchronize the methanol for steaming and being released in reaction process.Using 2h
After reaction, 90g20% phosphate aqueous solutions are added in into reaction mixture, rilanit special 61.6g is added in after being thoroughly mixed,
Reaction system is warming up to 130 DEG C and is kept the temperature, 5min is continued with 0.5MPa pressure by the gas dispersion apparatus of reactor bottom
Nitrogen bubbling is filled with into reaction system and is stirred continuously, then stops logical nitrogen, decompression steams liquid substance to kettle pressure and reaches
0.003MPa simultaneously continues to vacuumize 15min, and stopping vacuumizes is filled with nitrogen 3min by preceding method again, then stop inflation again into
Row vacuum distillation, so operates 3 times, then no liquid substance steams repeatedly, and reaction system is cooled to 100 DEG C, blowing, further
It is crushed after cooling, obtains white of the invention and flow freely shape product.
Embodiment 3
210.0g (2.0mol) diethanol amine and 2.8g sodium methoxides mixture input bottom there is into the anti-of gas dispersion apparatus
It answers in kettle, is heated to 100 DEG C under nitrogen protection.After pressure reaches 0.05MPa in extraction gas reactor to kettle, it is added dropwise in 2h
174.0g (1mol) dimethyl adipate, is stirred continuously reaction, and synchronize the methanol for steaming and being released in reaction process.Using 2h
After reaction, 113g20% phosphorous acid aqueous solutions are added in into reaction mixture, rilanit special is added in after being thoroughly mixed
Reaction system is warming up to 110 DEG C and kept the temperature by 105.6g, is held by the gas dispersion apparatus of reactor bottom with 0.5MPa pressure
Continuous 5min is filled with nitrogen bubbling into reaction system and is stirred continuously, and then stops logical nitrogen, and decompression steams liquid substance to kettle pressure
Up to 0.003MPa and continue to vacuumize 15min, stopping vacuumizes is filled with nitrogen 3min by preceding method again, then stops inflation again
It is evaporated under reduced pressure, is so operated 3 times repeatedly, then no liquid substance steams, and reaction system is cooled to 90 DEG C, blowing, into one
It is crushed after step cooling, obtains white of the invention and flow freely shape product.
Embodiment 4
This embodiment is comparative example；
210.0g (2.0mol) diethanol amine and 2.8g sodium methoxides mixture input bottom there is into the anti-of gas dispersion apparatus
It answers in kettle, is heated to 100 DEG C under nitrogen protection.After pressure reaches 0.05MPa in extraction gas reactor to kettle, it is added dropwise in 2h
174.0g (1mol) dimethyl adipate, is stirred continuously reaction, and synchronize the methanol for steaming and being released in reaction process.Using 2h
After reaction, 90g20% phosphate aqueous solutions are added in into reaction mixture, reaction system is warming up to 140 after being thoroughly mixed
DEG C and keep the temperature, continuing 5min by the gas dispersion apparatus of reactor bottom with 0.5MPa pressure is filled with nitrogen into reaction system
Bubbling is simultaneously stirred continuously, and then stops logical nitrogen, and decompression steams liquid substance to kettle pressure up to 0.003MPa and continues to vacuumize
15min, stopping vacuumizes is filled with nitrogen 3min by preceding method again, then stops inflation and is evaporated under reduced pressure again, so repeatedly
Operation 3 times, then no liquid substance steam, and reaction system are cooled to 100 DEG C, blowing further crushes after cooling, obtains white powder
Last shape product.
Product in above-described embodiment is added in 1 powder coating formulation of table：
Table 1：Powder coating formulation
SJ5122 during table 1 is formulated：Anhui Shenjian New Material Co., Ltd.'s Primid polyester, acid value 30-34mgKOH/
g；W-44：Guizhou China adds the barium sulfate of fine mining industry Co., Ltd production；R902：The rutile titanium dioxide of E.I.Du Pont Company's production
Powder；PV88：The polyacrylate levelling agent of Worlee companies production.
Ingredient each in table 1 in the high intensity mixer of 3000rmp/2 minutes is mixed, is then tested in the types of ZS -30
Melting mixing squeezes out in the double screw extruder of room, and temperature is 110 DEG C.Extrudate cools down, and electric coffee grinder crushes, and crosses 160 mesh sieve.
To the mode be electrostatically sprayed of powdery paints be sprayed on Q-Panel models, each sample sprays 110 ± 5 μ m thicks respectively
Model；Baking forms film to model after spraying under the conditions of 190 DEG C, 15 minutes respectively, estimates levelling and surface pinholes, simultaneously
Detect gloss and impact.The results detailed in Table 2.
The performance test methods and evaluation criterion of film are as follows：
The levelability evaluation criterion of film carries out levelling grading according to the levelling effect rating scale plate of U.S. PCI, and 1 is
Difference, 10 be excellent.
The glossiness test of film is with reference to standard GB/T/T9754.
The impact strength of film is with reference to standard GB/T/T1732.
Table 2：Performance powder coating is tested
Finally it should be noted that：Above content is only the design example and explanation to the present invention, this affiliated skills
The technical staff in art field does various modifications or additions to described specific embodiment or replaces in a similar way
In generation, design without departing from invention or surmount range defined in the claims, the protection of the present invention should all be belonged to
Range.
Claims (6)
1. a kind of synthetic method of beta-hydroxy alkylamide, it is characterised in that：Include the following steps：
(1) by β-alkanolamine and basic catalyst input reaction kettle, 80-100 DEG C is heated under the protection of inert gas, is taken out
Go out in the gas to kettle in kettle pressure up to after 0.03-0.05MPa, the dropwise addition alkyl carboxylates in 1-3 hour, and be stirred continuously into
Row ammonolysis reaction, while persistently steam the alcohol released in reaction process；
(2) alkyl carboxylates drop finishes, and continues to keep the temperature ammonolysis reaction under 0.03-0.05MPa after 0.5-2 hours, adjusts kettle internal pressure
It is by force normal pressure, the aqueous solution of phosphoric acid or phosphorous acid is added in into reaction mixture, is thoroughly mixed；
(3) rilanit special is added in into reaction system, reaction system is warming up to 110-150 DEG C and is kept the temperature, passes through reaction kettle
The gas dispersion apparatus of the bottom inert gas of charged pressure not less than 0.1MPa into reaction system carries out bubbling purging, continues
Stop inflation after inflating 2-10mi n, be evaporated under reduced pressure to kettle and force down in 0.005MPa, continue to vacuumize 5-20mi n, then stop
Vacuumize, be re-filled with inert gas carry out bubbling purging, stop inflation being evaporated under reduced pressure, such alternate intervals be inflated and
Vacuum distillation 2-5 times, until no liquid substance steams；
(4) remaining reaction product is cooled to 90-100 DEG C after steaming liquid substance, then blowing is cooled down, crushed to get white
Color powdery product.
2. a kind of synthetic method of beta-hydroxy alkylamide according to claim 1, it is characterised in that：The carboxylic
The molar ratio of acid alkyl ester and β-alkanolamine is 1:2-2.1.
3. a kind of synthetic method of beta-hydroxy alkylamide according to claim 1, it is characterised in that：The carboxylic
The mass ratio of acid alkyl ester and basic catalyst is 1:0.00001-0.05.
4. a kind of synthetic method of beta-hydroxy alkylamide according to claim 1, it is characterised in that：Phosphoric acid or Asia
The minimum molar ratio 1 for its hydrogen ion and hydroxide ion in basic catalyst of phosphoric acid:1-1.2, maximum for its hydroxyl with
The molar ratio of hydroxyl is 1 in β-alkanolamine:8.
5. a kind of synthetic method of beta-hydroxy alkylamide according to claim 1, it is characterised in that：The phosphorus
The concentration of aqueous solution of acid or phosphorous acid is 20-50wt%.
6. a kind of synthetic method of beta-hydroxy alkylamide according to claim 1, it is characterised in that：The hydrogen
Change the 8-50% that castor oil dosage is β-alkanolamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711487423.0A CN108203555A (en) | 2017-12-29 | 2017-12-29 | A kind of synthetic method of beta-hydroxy alkylamide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711487423.0A CN108203555A (en) | 2017-12-29 | 2017-12-29 | A kind of synthetic method of beta-hydroxy alkylamide |
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| CN108203555A true CN108203555A (en) | 2018-06-26 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109535024A (en) * | 2018-11-27 | 2019-03-29 | 黄山华惠科技有限公司 | A kind of color inhibition type beta-hydroxy alkylamide curing agent and the preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104817869A (en) * | 2015-03-30 | 2015-08-05 | 六安市捷通达化工有限责任公司 | Hydroxyalkylamide curing agent composition for powder coating materials, and preparation method thereof |
| CN104926677A (en) * | 2014-07-11 | 2015-09-23 | 六安市捷通达化工有限责任公司 | Production process of beta-hydroxyalkylamide |
-
2017
- 2017-12-29 CN CN201711487423.0A patent/CN108203555A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104926677A (en) * | 2014-07-11 | 2015-09-23 | 六安市捷通达化工有限责任公司 | Production process of beta-hydroxyalkylamide |
| CN104817869A (en) * | 2015-03-30 | 2015-08-05 | 六安市捷通达化工有限责任公司 | Hydroxyalkylamide curing agent composition for powder coating materials, and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 刘国杰: "《现代涂料工艺新技术》", 30 April 2000, 中国轻工业出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109535024A (en) * | 2018-11-27 | 2019-03-29 | 黄山华惠科技有限公司 | A kind of color inhibition type beta-hydroxy alkylamide curing agent and the preparation method and application thereof |
| CN109535024B (en) * | 2018-11-27 | 2021-08-31 | 黄山华惠科技有限公司 | Anti-yellowing beta-hydroxyalkylamide curing agent and preparation method and application thereof |
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