CN104448267A - Method for preparing solid epoxy resin toughened polyester - Google Patents
Method for preparing solid epoxy resin toughened polyester Download PDFInfo
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- CN104448267A CN104448267A CN201410812408.9A CN201410812408A CN104448267A CN 104448267 A CN104448267 A CN 104448267A CN 201410812408 A CN201410812408 A CN 201410812408A CN 104448267 A CN104448267 A CN 104448267A
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Abstract
The invention discloses a method for preparing solid epoxy resin toughened polyester. The method comprises the following steps: weighing, mixing, heating and stirring a terephthalic acid and polyol mixture and an esterification catalyst, performing esterification reaction at 175-185 DEG C, heating to 250-260 DEG C for 3.5-4.5 hours, draining the produced water, adding a defoaming agent into the mixture, controlling the vacuum degree to be less than -0.08MPa, vacuumizing for 3-5 hours, cooling, and discharging, thus obtaining a product, wherein the polyol mixture is a mixture of alkylene glycol and an organic waste liquid, and the organic waste liquid is a polyhydroxy organic compound recovered after a saturated salt water byproduct of an epoxy resin active diluent is evaporated and salted out. The solid epoxy resin toughened polyester is prepared by sufficiently using the organic waste liquid produced by preparing the solid epoxy resin active diluent as one of the raw materials, so that the production cost is reduced, the economic benefit of enterprise production is improved, direct discharge of the organic waste liquid is effectively avoided, then resource utilization of wastes is realized, and the method has certain economic benefits and social benefits.
Description
Technical field
The invention belongs to chemical technology field, be specifically related to the preparation method of the toughness reinforcing polyester of a kind of solid epoxy.
Background technology
Epoxy resin applies Organic chemical products very widely, its wide market, excellent economic benefit is brought to affiliated industry, at present, the production of single stage method epoxy resin adopts dihydroxyphenyl propane and epoxy chloropropane under the effect of sodium hydroxide, to react generation as raw material, and its by product is NaCl and H
2o, concrete reaction formula is as follows:
The epoxy resin E-12 that One-step production prepares cross-linking density after solidification is high, but has that internal stress is large, matter is crisp and the shortcoming such as shock-resistance, resistance to cracking and humidity resistance be poor, thus causes its application to be subject to certain restrictions.
Epoxide resin reactive diluent refers to the low molecular weight epoxy compound containing epoxide group, it participates in the curing reaction of epoxy resin, the viscosity of curing system can not only be reduced, and it is less to the performance impact after epoxy resin cure, concrete, the by product that epoxide resin reactive diluent produces in preparation process is mainly Yan Heshui, described separation of by-products can be made to form saturated brine and solid salt by the solid-liquid separation of routine, saturated brine is wherein again by neutralization, multiple-effect evaporation is recyclable obtains technical grade solid salt, and be dissolved in organism in saturated brine and can reclaim from concentrated mother liquor and obtain, it is flaxen thick for reclaiming this organic liquid waste obtained, analyze it after testing for polyhydroxy organic compound, hydroxyl value is mainly between 600-1000mgKOH/g, therefore this organic liquid waste is directly done offal treatment and is not only wasted resource, contaminate environment, also the health of the mankind is threatened, therefore how above-mentioned organic liquid waste is fully utilized effectively, avoid environmental pollution, it is the technical bottleneck that the personnel that require study solve.
Summary of the invention
The object of this invention is to provide that a kind of technique is simple, the preparation method of the toughness reinforcing polyester of solid epoxy of low stain, low cost.The polyhydroxy organic compound that salt recovery is analysed in the evaporation of the method epoxide resin reactive diluent saturated brine prepares the toughness reinforcing polyester of solid epoxy as one of raw material, effectively realizes the Appropriate application of waste resource, reduces environmental stress.
For achieving the above object, the technical solution used in the present invention is: the preparation method of the toughness reinforcing polyester of a kind of solid epoxy, and step is as follows:
Take the mixing of terephthalic acid, polyol blends and esterifying catalyst, heated and stirred, esterification is carried out under 175-185 DEG C of condition, and be warming up to 250-260 DEG C in 3.5-4.5h, the water produced is discharged, in mixture, adds defoamer, control vacuum tightness and be less than-0.08MPa, vacuumize 3-5h, cooling discharging, obtain product;
Described terephthalic acid, polyol blends according to the carboxyl in terephthalic acid and the hydroxyl in polyol blends with the mixed in molar ratio of 1.05-1.5:1; The quality addition of esterifying catalyst, defoamer is 0.1-0.2%, 0.1-0.2% of terephthalic acid respectively; Polyol blends is the mixture of aklylene glycol and organic liquid waste, and described organic liquid waste is the polyhydroxy organic compound reclaimed after salt is analysed in the by product saturated brine evaporation of epoxide resin reactive diluent.
The beneficial effect adopting technique scheme to produce is: the organic liquid waste that the present invention makes full use of Chemical Manufacture carries out the preparation of the toughness reinforcing polyester of solid epoxy as one of raw material, not only save production cost, improve the economic benefit that enterprise produces, and effectively avoid organic liquid waste directly to discharge, thus improve environmental quality, there is certain economic benefit and social benefit, concrete, prior art prepares the by product that produces in epoxide resin reactive diluent process by obtaining saturated brine after solid-liquid separation, the waste liquid that these saturated brines reclaim after analysing salt by evaporation is organic liquid waste, these organic liquid wastes are be dissolved in saturated brine before recovery.The toughness reinforcing polyester of the solid epoxy adopting method disclosed by the invention to prepare adds toughening effect and the physical strength that effectively can ensure epoxy resin in epoxy resin to.
As further preferred version: described aklylene glycol is one or more in ethylene glycol, Diethylene Glycol and neopentyl glycol.Preferably, described aklylene glycol is obtained by the mixed in molar ratio preparation according to 1.5 ~ 1.6:1.0 ~ 1.2:0.5 ~ 0.6 of ethylene glycol, Diethylene Glycol and neopentyl glycol, and the hydroxyl molar weight in described organic liquid waste is no more than 10% of hydroxyl mole total amount in ethylene glycol and Diethylene Glycol.Through verification experimental verification, the organic liquid waste Substitute For Partial ethylene glycol that the application adopts saturated brine desalination to reclaim and Diethylene Glycol, the physical and chemical performance that the toughness reinforcing polyester of the solid epoxy prepared like this is specifically good, thus make organic liquid waste be recycled utilization, not only increase economic efficiency, and effectively reduce environmental pollution.
Concrete scheme is: described esterifying catalyst is organotin or organic titanium class catalyzer, and described organic tin catalyzer is the one in butyl stannic oxide, butyl stannic oxide muriate, butyl tin acetate; Described defoamer is the one of three iso-butyl ester of phosphoric acid or tributyl phosphate.In fact, just list several conventional esterifying catalyst and defoamer herein, polyester esterifying catalyst used is prepared and defoamer can be applied and the esterification described in the application and polycondensation in prior art, that is the toughness reinforcing polyester of solid epoxy disclosed in the present application has no special requirements to the kind of esterifying catalyst and defoamer in preparation, and versatility is stronger.
In addition, for ensureing preparation efficiency, preferably, the mixture that described terephthalic acid, polyol blends and esterifying catalyst are formed is heated to 175-185 DEG C in 1h, described mixture is vacuumize 3-5h, cooling discharging under vacuum tightness is less than the condition of-0.08MPa after adding defoamer.
Embodiment
For clearer explanation technical scheme disclosed in this invention, be further described below by way of following 8 embodiments.
Embodiment 1: the preparation (not adding organic liquid waste) of the toughness reinforcing polyester of solid epoxy
98g ethylene glycol, 116.5g Diethylene Glycol, 58g neopentyl glycol, 480g terephthalic acid and 0.75g butyl stannic oxide is added in the 500ml four-hole boiling flask that electric heating cover, agitator and reflux exchanger be housed, in 1h, mixture is heated to 175-180 DEG C and carries out esterification, and in 4h, mixture is slowly heated to 255 DEG C, the water produced is discharged, add 0.8g three iso-butyl ester of phosphoric acid, control vacuum tightness and be less than-0.08MPa, vacuumize 4h, cooling discharging, obtains product.
Embodiment 2: the preparation (organic liquid waste replaces the Diethylene Glycol of 2.5% hydroxyl molar weight in embodiment 1) of the toughness reinforcing polyester of solid epoxy
To electric heating cover is housed, 98g ethylene glycol is added in the 500ml four-hole boiling flask of agitator and reflux exchanger, 110.5g Diethylene Glycol, 62g neopentyl glycol, 473g terephthalic acid, 9.3g organic liquid waste and 0.75g butyl stannic oxide, in 1h, mixture is heated to 175-180 DEG C and carries out esterification, and in 4h, mixture is slowly heated to 255 DEG C, water outlet is complete, add 1.0g three iso-butyl ester of phosphoric acid, control vacuum tightness and be less than-0.08MPa, vacuumize 4h, cooling discharging, obtain product, described organic liquid waste is the polyhydroxy organic compound reclaimed after salt is analysed in the by product saturated brine evaporation of epoxide resin reactive diluent, lower same.
Embodiment 3: the preparation (organic liquid waste replaces the ethylene glycol of 2.5% hydroxyl molar weight in embodiment 1) of the toughness reinforcing polyester of solid epoxy
93.1g ethylene glycol, 116.5g Diethylene Glycol, 62g neopentyl glycol, 480g terephthalic acid, 9.3g organic liquid waste and 0.8g butyl stannic oxide is added in the 500ml four-hole boiling flask that electric heating cover, agitator and reflux exchanger be housed, in 1h, mixture is heated to 175-180 DEG C and carries out esterification, and in 4h, mixture is slowly heated to 255 DEG C, the water produced is discharged, add 1.0g three iso-butyl ester of phosphoric acid, control vacuum tightness and be less than-0.08MPa, vacuumize 4h, cooling discharging, obtains product.
Embodiment 4: the preparation (organic liquid waste replaces the Diethylene Glycol of 2.5% hydroxyl molar weight and the ethylene glycol of 2.5% hydroxyl molar weight in embodiment 1) of the toughness reinforcing polyester of solid epoxy
95.5g ethylene glycol, 113.6g Diethylene Glycol, 58g neopentyl glycol, 480g terephthalic acid, 11g organic liquid waste and 0.75g butyl stannic oxide is added in the 500ml four-hole boiling flask that electric heating cover, agitator and reflux exchanger be housed, in 1h, mixture is heated to 175-180 DEG C and carries out esterification, and in 4h, mixture is slowly heated to 255 DEG C, the water produced is discharged, add 0.8g three iso-butyl ester of phosphoric acid, control vacuum tightness and be less than-0.08MPa, vacuumize 4h, cooling discharging, obtains product.
Embodiment 5: the preparation (organic liquid waste replaces the Diethylene Glycol of 5% hydroxyl molar weight and the ethylene glycol of 5% hydroxyl molar weight in embodiment 1) of the toughness reinforcing polyester of solid epoxy
93g ethylene glycol, 110.7g Diethylene Glycol, 58g neopentyl glycol, 473g terephthalic acid, 22g organic liquid waste and 0.75g butyl stannic oxide is added in the 500ml four-hole boiling flask that electric heating cover, agitator and reflux exchanger be housed, in 1h, mixture is heated to 175-180 DEG C and carries out esterification, and in 4h, mixture is slowly heated to 255 DEG C, the water produced is discharged, add 0.8g three iso-butyl ester of phosphoric acid, control vacuum tightness and be less than-0.08MPa, vacuumize 4h, cooling discharging, obtains product.
Embodiment 6: the preparation (organic liquid waste replaces the Diethylene Glycol of 5% hydroxyl molar weight and the ethylene glycol of 5% hydroxyl molar weight in embodiment 1) of the toughness reinforcing polyester of solid epoxy
93g ethylene glycol, 110.7g Diethylene Glycol, 47g neopentyl glycol, 510g terephthalic acid, 22g organic liquid waste and 0.6g butyl tin acetate is added in the 500ml four-hole boiling flask that electric heating cover, agitator and reflux exchanger be housed, in 1h, mixture is heated to 180-185 DEG C and carries out esterification, and in 4h, mixture is slowly heated to 255 DEG C, the water produced is discharged, add 0.5g tributyl phosphate, control vacuum tightness and be less than-0.08MPa, vacuumize 3h, cooling discharging, obtains product.
Embodiment 7: the preparation (organic liquid waste replaces the Diethylene Glycol of 5% hydroxyl molar weight and the ethylene glycol of 5% hydroxyl molar weight in embodiment 1) of the toughness reinforcing polyester of solid epoxy
93g ethylene glycol, 110.7g Diethylene Glycol, 63g neopentyl glycol, 460g terephthalic acid, 22g organic liquid waste and 0.5g butyl tin acetate is added in the 500ml four-hole boiling flask that electric heating cover, agitator and reflux exchanger be housed, in 1h, mixture is heated to 180-185 DEG C and carries out esterification, and in 4h, mixture is slowly heated to 255 DEG C, the water produced is discharged, add 0.46g tributyl phosphate, control vacuum tightness and be less than-0.08MPa, vacuumize 5h, cooling discharging, obtains product.
Adopt GB/T 12007.6-1989 " epoxy resin softening point measurement method ring and ball method ", GB/T2895-2008 " mensuration of plastic polyester resin portion acid number and total acid value ", GB/T 22295-2008 " epoxy resin color measurenent method Gardner Color method " detects the softening temperature of increasing polyester prepared by embodiment 1-5 respectively, acid number and colourity, result is as shown in table 1 below, as can be seen from the table, adopt organic liquid waste to substitute the solid epoxy toughened resin that aklylene glycol prepares and there is good physicals, so effectively can ensure the rational utilization of waste resource, thus reduce the pollution of environment.
The physical properties of the toughness reinforcing polyester of table 1
| Project | Acid number (mgKOH/g) | Softening temperature (DEG C) | Gardner Color |
| Embodiment 1 | 2.84 | 92 | ≤1 |
| Embodiment 2 | 4.61 | 88 | ≤2 |
| Embodiment 3 | 4.70 | 89 | ≤2 |
| Embodiment 4 | 3.70 | 94.5 | ≤3 |
| Embodiment 5 | 3.50 | 98 | ≤3 |
Embodiment 8: the application of the toughness reinforcing polyester of solid epoxy
In E-12 epoxy resin, add according to 5-25% ratio the toughness reinforcing polyester that embodiment 1,4 and 5 prepares respectively to be cured, performance test is carried out to the E-12 epoxy resin of solidification, after testing, the draw a design test result of E-12 epoxy resin under mat black condition of adding different toughness reinforcing polyester is as shown in table 2 below, it can be seen from the table, adopt organic liquid waste to substitute the curing reaction of the toughness reinforcing polyester participation epoxy resin that dialkyl group glycol prepares, effectively can ensure the physical and chemical performance of epoxy resin.
The physical properties of the toughness reinforcing polyester of table 2
Claims (7)
1. a preparation method for the toughness reinforcing polyester of solid epoxy, step is as follows:
Take the mixing of terephthalic acid, polyol blends and esterifying catalyst, heated and stirred, esterification is carried out under 175-185 DEG C of condition, and be warming up to 250-260 DEG C in 3.5-4.5h, the water produced is discharged, in mixture, adds defoamer, control vacuum tightness and be less than-0.08MPa, vacuumize 1-2h, cooling discharging, obtain product;
Described terephthalic acid, polyol blends according to the carboxyl in terephthalic acid and the hydroxyl in polyol blends with the mixed in molar ratio of 1.05-1.5:1; The quality addition of esterifying catalyst, defoamer is 0.1-0.2%, 0.1-0.2% of terephthalic acid respectively; Polyol blends is the mixture of aklylene glycol and organic liquid waste, and described organic liquid waste is the polyhydroxy organic compound reclaimed after salt is analysed in the by product saturated brine evaporation of epoxide resin reactive diluent.
2. the preparation method of the toughness reinforcing polyester of solid epoxy according to claim 1, is characterized in that: described aklylene glycol is one or more in ethylene glycol, Diethylene Glycol, neopentyl glycol.
3. the preparation method of the toughness reinforcing polyester of solid epoxy according to claim 1 or 2, it is characterized in that: described aklylene glycol is obtained by the mixed in molar ratio preparation according to 1.5 ~ 1.6:1.0 ~ 1.2:0.5 ~ 0.6 of ethylene glycol, Diethylene Glycol and neopentyl glycol, and the hydroxyl molar weight in described organic liquid waste is no more than 10% of hydroxyl mole total amount in ethylene glycol and Diethylene Glycol.
4. the preparation method of the toughness reinforcing polyester of solid epoxy according to claim 3, it is characterized in that: described esterifying catalyst is organotin or organic titanium class catalyzer, described organic tin catalyzer is the one in butyl stannic oxide, butyl stannic oxide muriate, butyl tin acetate.
5. the preparation method of the toughness reinforcing polyester of solid epoxy according to claim 3, is characterized in that: described defoamer is three iso-butyl ester of phosphoric acid or tributyl phosphate.
6. the preparation method of the toughness reinforcing polyester of solid epoxy according to claim 3, is characterized in that: described mixture is heated to 175-185 DEG C in 1h.
7. the preparation method of the toughness reinforcing polyester of solid epoxy according to claim 6, is characterized in that: described mixture is vacuumize 3-5h, cooling discharging under vacuum tightness is less than the condition of-0.08MPa after adding defoamer.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566679A (en) * | 2015-12-29 | 2016-05-11 | 浙江荣泰科技企业有限公司 | Ester compound, and preparation method and application thereof to epoxy resin casting system |
| CN110408002A (en) * | 2019-08-27 | 2019-11-05 | 黄山五环科技有限公司 | Preparation method based on automotive hub film epoxy resin |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101265323A (en) * | 2007-03-16 | 2008-09-17 | 张鹏飞 | Polyester polyol |
| CN103467714A (en) * | 2013-09-05 | 2013-12-25 | 安徽神剑新材料股份有限公司 | Polyester resin and synthesis method thereof |
| CN103755940A (en) * | 2013-12-21 | 2014-04-30 | 安徽神剑新材料股份有限公司 | Preparation method and application of polyester resin applied to thermo-sensitive base material powder coating |
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- 2014-12-23 CN CN201410812408.9A patent/CN104448267B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101265323A (en) * | 2007-03-16 | 2008-09-17 | 张鹏飞 | Polyester polyol |
| CN103467714A (en) * | 2013-09-05 | 2013-12-25 | 安徽神剑新材料股份有限公司 | Polyester resin and synthesis method thereof |
| CN103755940A (en) * | 2013-12-21 | 2014-04-30 | 安徽神剑新材料股份有限公司 | Preparation method and application of polyester resin applied to thermo-sensitive base material powder coating |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566679A (en) * | 2015-12-29 | 2016-05-11 | 浙江荣泰科技企业有限公司 | Ester compound, and preparation method and application thereof to epoxy resin casting system |
| CN110408002A (en) * | 2019-08-27 | 2019-11-05 | 黄山五环科技有限公司 | Preparation method based on automotive hub film epoxy resin |
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