CN100360599C - PVC antistatic elasticizer synthesis process - Google Patents
PVC antistatic elasticizer synthesis process Download PDFInfo
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Abstract
The present invention relates to a PVC antistatic plasticizing agent synthesis technology which needs to solve the technical problem that products produced by the technology need to resist static electricity and plasticize. The present invention is characterized in that the mole ratio of dibasic acid to diethylene glycol ether in an esterification reaction is 1.0: 0.5 to 6.0, the reaction is carried out under a heating vacuum condition, and then, paratoluenesulfonic acid as a catalyst is added for full reaction under the heating vacuum condition; neutralization, water washing and still stratification are carried out, ether and colors are removed from an ester taking layer, and thus, esterified objects are obtained; 2) in a synthesis reaction, bi-polyoxyethylene alkyl amine is added in the esterified objects, the esterified objects taking 10 to 80 % of the total weight are acidized by acid and dewatered via vacuum, temperature is lowered, epoxyethane is added in a dripping way, and the epoxyethane has the dripping quantity that the mole ratio of the polyoxyethylene alkyl amine to the epoxyethane is 0.5 to 4.0: 1.0, reaction is carried out fully, and finial products are obtained after temperature drop and material discharge.
Description
Technical field
The present invention relates to a kind of auxiliary agent, specifically is a kind of synthesis technique of PVC antistatic elasticizer.
Background technology
Polyvinyl chloride is a kind of versatility plastics, is widely used.But itself electrical insulating property after it contacts with other material or rubs, can produce accumulation of static electricity.Therefore become a kind of harm in many occasions.As plastic conveyor belt or plastics tubing when carrying inflammable and explosive material, often because of the mobile generation static discharge or the blast of material; In precision instrument watch-keeping cubicle and computer house, because plastic static causes the error of instrument; Plastics in the colliery (ventilating duct, safety helmet, tool housing etc.) produce static, can cause gas explosion; The plastics film work in-process produces static adhering device difficult drop-off, and the plastics bag heat sealing fastness of making is poor, and breakage rate is high and print bad.In recent years, a large amount of uses of plastics, attractive in appearance impaired as polyvinyl chloride door and window, window shutter etc. because static causes dust suction, and easy cleaning not, reduce use value.
Different plastics will use different static inhibitor just can receive effective result.Igelite has its singularity, other resin relatively, and its static inhibitor research is difficulty.In addition, the affiliation that adds of some static inhibitor changes the physical and mechanical properties of polyvinyl chloride, degenerates such as the adding of meetings such as the tensile strength of goods, elongation at break because of static inhibitor, requires static inhibitor to have certain plasticity.The development of China's softening agent is started late, no matter produce, still there are a certain distance in everyway such as processing unit, kind, function and developed country in research.At present, the kind of China's softening agent roughly has more than 100, and commonly used has 20～30, based on general kind.And the static inhibitor that is used for PVC is few, does not then see the report that scale production is arranged and be used for the both antistatic plastifying auxiliary agent of PVC.
Summary of the invention
The technical issues that need to address of the present invention are, the synthesis technique of a kind of not only antistatic but also plastifying PVC used additives is provided.
The synthesis technique of PVC antistatic elasticizer of the present invention is characterized in that,
1) esterification---diprotic acid: the mol ratio of diethylene glycol ether=1.0: 0.5～6.0, under the heating, vacuum condition, react, add the catalyzer tosic acid then, fully reaction under the heating, vacuum condition, neutralization washing, standing demix, get ester pull-up ether, decolouring, promptly get carboxylate; Described diprotic acid is the aliphatic alkyl that contains saturated divalence, the aliphatic alkyl of undersaturated divalence, the ester ring type alkyl of divalence, a kind of acid in the aromatic hydrocarbyl of divalence;
2) building-up reactions---in carboxylate, add two polyoxyethylene alkyl amines, make carboxylate account for 10～80% of gross weight, carry out acidifying with acid, through vaccum dewatering, cooling drips oxyethane, and its dripping quantity is two polyoxyethylene alkyl amines: the mol ratio of oxyethane=0.5～4.0: 1.0, fully reaction again, cooling discharge gets the finished product (AP).
As preferably, the synthesis technique of PVC antistatic elasticizer of the present invention is,
1) esterification---diprotic acid: the mol ratio of diethylene glycol ether=1.0: 0.5～4.0, under the heating, vacuum condition, react, add the catalyzer tosic acid then, fully reaction under the heating, vacuum condition, neutralization washing, standing demix, get ester pull-up ether, decolouring, promptly get carboxylate; Described diprotic acid is the aliphatic alkyl that contains saturated divalence, the aliphatic alkyl of undersaturated divalence, the ester ring type alkyl of divalence, a kind of acid in the aromatic hydrocarbyl of divalence;
2) building-up reactions---in carboxylate, add two polyoxyethylene alkyl amines, make carboxylate account for 30～80% of gross weight, carry out acidifying with acid, through vaccum dewatering, cooling drips oxyethane, and its dripping quantity is two polyoxyethylene alkyl amines: the mol ratio of oxyethane=0.5～3.5: 1.0, fully reaction again, cooling discharge gets the finished product (AP).
Synthesis technique commonly used is,
1) 1) esterification---diprotic acid: the mol ratio of diethylene glycol ether=1.0: 0.5～4.0, at 110～170 ℃, vacuum condition reacted 0.5～3 hour down, adding consumption then is the catalyzer tosic acid of principal goods material weight 0.1～1.5%, at 100～190 ℃, react under the vacuum about 1～7 hour, reactant is again through 10%Na
2CO
3In the aqueous solution and the washing, standing demix, get the ester layer add 2% gac 110～200 ℃ of underpressure distillation slough excessive ether and the decolouring, promptly get carboxylate;
2) building-up reactions---in carboxylate, add two polyoxyethylene alkyl amines, make carboxylate account for 30～80% of gross weight, carry out acidifying with acid, the dropping time is 1 hour, 70 ℃ of temperature of reaction, slaking is 1 hour then, through vaccum dewatering, cooling, under 50～150 ℃ of temperature, slowly drip oxyethane, the two polyoxyethylene alkyl amines of its dripping quantity: the mol ratio of oxyethane=0.5～3.5: 1.0, add afterreaction a few hours, cooling discharge gets yellow to brown xanchromatic thick liquid, i.e. the finished product (AP).
As preferably, described diprotic acid is that the carbon number of R is 1～12 aliphatic dibasic acid.
Above-mentioned esterification reaction tech flow process is:
Catalyzer
Acid+ether---〉esterification → neutralization → washing → layering → distillation (decolouring)---〉is filtered---〉esterified prod
Above-mentioned esterification formula is:
HOOC-R-COOH+C
mH
2m+1OCH
2CH
2OCH
2CH
2The OH tosic acid
M=1 in the formula～10,
Above-mentioned diprotic acid is saturated or the aliphatic alkyl of undersaturated divalence, or the ester ring type alkyl of divalence, or the aromatic hydrocarbyl of divalence, and optimal diprotic acid is that the carbon number of R is 1～12 aliphatic dibasic acid.
Above-mentioned synthesis process flow process is seen accompanying drawing 1.
Above-mentioned building-up reactions formula is:
In the formula: a=b+c, R are C
12-C
18Straight chained alkyl, m, n are 〉=1, and acid is mineral acid.
Synthesis technique of the present invention has following characteristics:
The unique easily row of operational path adopts diprotic acid and diethylene glycol ether esterification, is catalyzer with the tosic acid, the synthetic esterification products that makes.Two polyoxyethylene alkyl amines and acid and reacting ethylene oxide, esterification products make antistatic elasticizer as synergist.Esterification products can play the effect that makes the system homodisperse as synergist in reaction, promote reaction to carry out smoothly.In use can improve the plasticizing capacity of product, and can help product to move to the PVC frosting.The product that obtains by above technological reaction is a kind of compound antistatic elasticizer of being formed with a certain proportion of cation quaternary ammonium salt type surfactant, nonionogenic tenside and synergist.Nonionogenic tenside during product is formed is an intermediate feed of making cats product, like this as long as reasonably control in quaterisation
Proportioning between the reactant just can synthesize the desirable mixture of forming.The antistatic elasticizer that obtains, its plasticizing efficiency and conventional PVC plasticizer DOP are similar, and the extender plasticizer that can be used as the PVC plastics uses.Product just has good static resistance in the extremely short time simultaneously, even after processing one month, antistatic effect does not weaken, and indivedual batches of effects are better.The product water-wash resistance is good, and weather resistance is good.
Description of drawings
Fig. 1 is the synthesis process schema.
Embodiment
Below by embodiment, technical scheme of the present invention is described in further detail.
1, embodiment
Embodiment 1.Propanedioic acid: diethylene glycol ether=1.0: 1.5 (mol ratio) is catalyzer (consumption be principal goods material weight 0.6%) with the tosic acid.At first under the catalyst-free situation, at 110～170 ℃, vacuum condition reacted 3 hours down, added the catalyzer tosic acid then, and at 110～170 ℃, reaction is about 1 hour under the vacuum, and product is through 10%Na then
2CO
3In the aqueous solution and the washing, standing demix, get the ester layer add 2% gac 110～200 ℃ of underpressure distillation slough excessive ether and the decolouring, promptly get carboxylate.
Adopt two polyoxyethylene alkyl amines to add quantitative carboxylate, carboxylate content is 25% of total amount, carries out acidifying with hydrochloric acid, the dropping time is 1 hour, 70 ± 5 ℃ of temperature of reaction, and slaking is 1 hour then, remove moisture with vacuum again, the no globule distillates promptly and ends in visor.Being cooled to following pair polyoxyethylene alkyl amine of certain temperature and oxyethane mol ratio then is 1.0: 1.0, slowly feeds oxyethane, drips 55 ± 5 ℃ of oxyethane temperature, 1 hour time, add afterreaction a few hours, and cooling discharge promptly gets product (AP).
Embodiment 2.Pentanedioic acid: diethylene glycol ether=1.0: 4.0 (mol ratio) is catalyzer (consumption be principal goods material weight 0.5%) with the tosic acid.At first under the catalyst-free situation, at 110～170 ℃, vacuum condition reacted 0.5 hour down, added the catalyzer tosic acid then, and at 110～170 ℃, reaction is about 7 hours under the vacuum, and product is through 10%Na then
2CO
3In the aqueous solution and the washing, standing demix, get the ester layer add 2% gac 110～200 ℃ of underpressure distillation slough excessive ether and the decolouring, promptly get carboxylate.
Adopt two polyoxyethylene alkyl amines to add quantitative carboxylate, carboxylate content is 55% of total amount, carries out acidifying with nitric acid, the dropping time is 1 hour, 70 ± 5 ℃ of temperature of reaction, and slaking is 1 hour then, remove moisture with vacuum again, the no globule distillates promptly and ends in visor.Being cooled to following pair polyoxyethylene alkyl amine of certain temperature and oxyethane mol ratio then is 2.0: 1.0, slowly feeds oxyethane, drips 115 ± 5 ℃ of oxyethane temperature, 1 hour time, add afterreaction a few hours, and cooling discharge promptly gets product (AP).
Embodiment 3.Oxalic acid: diethylene glycol dimethyl ether=1.0: 4.0 (mol ratio) is catalyzer (consumption be principal goods material weight 0.5%) with the tosic acid.At first under the catalyst-free situation, at 110～170 ℃, vacuum condition reacted 3 hours down, added the catalyzer tosic acid then, and at 110～170 ℃, reaction is about 7 hours under the vacuum, and product is through 10%Na then
2CO
3In the aqueous solution and the washing, standing demix, get the ester layer add 2% gac 110～200 ℃ of underpressure distillation slough excessive ether and the decolouring, promptly get carboxylate.
Adopt two polyoxyethylene alkyl amines to add quantitative carboxylate, carboxylate content is 40% of total amount, carries out acidifying with nitric acid, the dropping time is 1 hour, 70 ± 5 ℃ of temperature of reaction, and slaking is 1 hour then, remove moisture with vacuum again, the no globule distillates promptly and ends in visor.Being cooled to following pair polyoxyethylene alkyl amine of certain temperature and oxyethane mol ratio then is 1.5: 1.0, slowly feeds oxyethane, drips 95 ± 5 ℃ of oxyethane temperature, 1 hour time, add afterreaction a few hours, and cooling discharge promptly gets product (AP).
Other embodiment also has:
| Sequence number | Diprotic acid | Diprotic acid: diethylene glycol ether (mol ratio) | Carboxylate accounts for the % of gross weight | Two polyoxyethylene alkyl amines: oxyethane (mol ratio) | Product (AP) |
| 1 | Propanedioic acid | 1.0∶0.8 | 10 | 0.5∶1.0 | |
| 2 | Propanedioic acid | 1.0∶1.5 | 25 | 1.0∶1.0 | Embodiment 1 |
| 3 | Propanedioic acid | 1.0∶6.0 | 50 | 4.0∶1.0 | |
| 4 | Propanedioic acid | 1.0∶0.5 | 80 | 0.7∶1.0 | |
| 5 | Propanedioic acid | 1.0∶4.0 | 30 | 3.5∶1.0 | |
| 6 | Pentanedioic acid | 1.0∶1.0 | 10 | 4.0∶1.0 | |
| 7 | Pentanedioic acid | 1.0∶4.0 | 55 | 2.0∶1.0 | Embodiment 2 |
| 8 | Pentanedioic acid | 1.0∶6.0 | 80 | 0.5∶1.0 | |
| 9 | Pentanedioic acid | 1.0∶0.5 | 60 | 3.2∶1.0 | |
| 10 | Pentanedioic acid | 1.0∶0.6 | 30 | 1.0∶1.0 | |
| 11 | Oxalic acid | 1.0∶1.0 | 80 | 3.5∶1.0 | |
| 12 | Oxalic acid | 1.0∶4.0 | 40 | 1.5∶1.0 | Embodiment 3 |
| 13 | Oxalic acid | 1.0∶6.0 | 10 | 0.5∶1.0 | |
| 14 | Oxalic acid | 1.0∶0.5 | 60 | 4.0∶1.0 | |
| 15 | Oxalic acid | 1.0∶0.6 | 35 | 1.0∶1.0 |
2, put into practice, test effect
(1) performance test
Product (AP-1, AP-2) is made an addition in the transparent PVC sheet material formula, adopt Φ 160 double roll mills in blocks, 170～180 ℃ of temperature, 5 minutes time.Carry out the test of the every physicals of test piece then, test recipe is as shown in table 1.
Table 1 basic recipe
Table 2 The performance test results
| Project | 1 (blank) | 2(AP-1) | 3(AP-2) |
| Tensile strength, MPa | 9.73 | 10.8 | 10.7 |
| Transmittance, % | 88.9 | 91.1 | 91.4 |
| Elongation at break, % | 320 | 320 | 320 |
| Turbidity | 5.55 | 2.2 | 3.7 |
In test, blank sample adds 40 parts of plasticizer DOPs (with respect to 100 parts of PVC amounts), and AP-1, AP-2 sample add 10 parts of antistatic elasticizers respectively, and corresponding plasticizer DOP umber reduces 10 parts, to test the plasticizing capacity of this antistatic elasticizer.By above test as can be seen, this antistatic elasticizer has improved tensile strength, the transmittance of PVC sheet material, and turbidity reduces, and elongation at break is constant, and the plasticizing capacity to the PVC goods increases generally.Illustrate that this antistatic elasticizer plasticizing efficiency wants a little higher than conventional PVC plasticizer DOP, the extender plasticizer that can be used as the PVC plastics uses.
(2) application test
1. flexible PVC material
With following four prescription (table 3) mixing one-tenth sheet materials on twin-roll machine, temperature about 180 ℃, pressure 0.7Mpa, time 5min carries out test piece antistatic property test, result such as table 4 then.
From table 4, can reach a conclusion, this type of antistatic elasticizer can make four to five orders of magnitude of surface resistivity decline of flexible PVC sheet material, reaches 107-8 ohm, shows that product has tangible antistatic property.And just have good static resistance in the extremely short time, even after processing one month, antistatic effect does not weaken yet, and antistatic effect is better on the contrary.
Table 3 flexible PVC sheet material basic recipe
| Test number | 1 (blank) | 2(AP-3) | 3(AP-4) | 4(AP-5) |
| PVC | 100 | 100 | 100 | 100 |
| Stablizer | 1.0 | 1.0 | 1.0 | 1.0 |
| ESO | 2.0 | 2.0 | 2.0 | 2.0 |
| DOP | 40 | 32 | 32 | 32 |
| Lubricant | 0.5 | 0.5 | 0.5 | 0.5 |
| AP | / | 8 | 8 | 8 |
Table 4 test condition: 23～25 ℃, 60～65%R.H.
2. semi-rigid PVC material
Table 5 basic recipe:
| Test number | 1(AP-6) | 2(AP-7) | 3(AP-8) |
| PVC | 100 | 100 | 100 |
| Stablizer | 1.0 | 1.0 | 1.0 |
| DOP | 20 | 20 | 20 |
| Lubricant | In right amount | In right amount | In right amount |
| AP | 5 | 5 | 5 |
Table 6 performance situation
Can find out that from table 6 antistatic elasticizer also has antistatic property preferably for semi-rigid PVC, promptly usage quantity has only 5% also can work.
3. water-wash test
The flexible PVC sheet that will contain 8% content antistatic elasticizer dries to be measured with cotton and distilled water flushing, wiping twice then.The results are shown in Table 8
Table 7 basic recipe:
| Test number | 1(AP-9) | 2(AP-10) | 3(AP-11) |
| PVC | 100 | 100 | 100 |
| Stablizer | 1.0 | 1.0 | 1.0 |
| ESO | 2.0 | 2.0 | 2.0 |
| DOP | 32 | 32 | 32 |
| Lubricant | 0.5 | 0.5 | 0.5 |
| AP | 8 | 8 | 8 |
Table 8 test condition: 23～25 ℃, 60～65%R.H.
As can be seen from the above table, this antistatic elasticizer water-wash resistance is fine, and washing can recover static resistance one day after, illustrates that also product transport property in material is good, and reaches optimum regime very soon.This has good use prospect at aspects such as some outdoor materials useds or PVC water pipes.
4. endurance test
Select a collection of flexible PVC slice, thin piece, from processing after the 1st day with regard to tracking and testing, see its weather resistance situation.Concrete prescription sees Table 9.
Table 9 flexible PVC prescription
| Test number | 1 (blank) | 2(AP-12) | 3(AP-13) | 4(AP-14) |
| PVC | 100 | 100 | 100 | 100 |
| Stablizer | 1.0 | 1.0 | 1.0 | 1.0 |
| ESO | 2.0 | 2.0 | 2.0 | 2.0 |
| DOP | 40 | 32 | 32 | 32 |
| Lubricant | 0.5 | 0.5 | 0.5 | 0.5 |
| AP | / | 8 | 8 | 8 |
Table 10 endurance test
As seen from Table 10, sample still keeps antistatic property preferably through processing back 15 days, one month, 3 months, and the durable of static inhibitor plays a role clearly.
Claims (6)
1, a kind of synthesis technique of PVC antistatic elasticizer is characterized in that,
1) esterification---diprotic acid: the mol ratio of diethylene glycol ether=1.0: 0.5～6.0, under the heating, vacuum condition, react, add the catalyzer tosic acid then, fully reaction under the heating, vacuum condition, neutralization washing, standing demix, get ester pull-up ether, decolouring, promptly get carboxylate; Described diprotic acid is the aliphatic alkyl that contains saturated divalence, the aliphatic alkyl of undersaturated divalence, the ester ring type alkyl of divalence, a kind of acid in the aromatic hydrocarbyl of divalence;
2) building-up reactions---in carboxylate, add two polyoxyethylene alkyl amines, make carboxylate account for 10～80% of gross weight, carry out acidifying with mineral acid, through vaccum dewatering, cooling drips oxyethane, and its dripping quantity is two polyoxyethylene alkyl amines: the mol ratio of oxyethane=0.5～4.0: 1.0, fully reaction again, cooling discharge gets the finished product.
2, the synthesis technique of PVC antistatic elasticizer according to claim 1 is characterized in that,
1) esterification---diprotic acid: the mol ratio of diethylene glycol ether=1.0: 0.5～4.0, under the heating, vacuum condition, react, add the catalyzer tosic acid then, fully reaction under the heating, vacuum condition, neutralization washing, standing demix, get ester pull-up ether, decolouring, promptly get carboxylate; Described diprotic acid is the aliphatic alkyl that contains saturated divalence, the aliphatic alkyl of undersaturated divalence, the ester ring type alkyl of divalence, a kind of acid in the aromatic hydrocarbyl of divalence;
2) building-up reactions---in carboxylate, add two polyoxyethylene alkyl amines, make carboxylate account for 30～80% of gross weight, carry out acidifying with mineral acid, through vaccum dewatering, cooling drips oxyethane, and its dripping quantity is two polyoxyethylene alkyl amines: the mol ratio of oxyethane=0.5～3.5: 1.0, fully reaction again, cooling discharge gets the finished product.
3, the synthesis technique of PVC antistatic elasticizer according to claim 2 is characterized in that,
1) esterification---diprotic acid: the mol ratio of diethylene glycol ether=1.0: 0.5～4.0, at 110～170 ℃, vacuum condition reacted 0.5～3 hour down, adding consumption then is the catalyzer tosic acid of principal goods material weight 0.1～1.5%, at 100～190 ℃, react under the vacuum about 1～7 hour, reactant is again through 10%Na
2CO
3In the aqueous solution and the washing, standing demix, get the ester layer add 2% gac 110～200 ℃ of underpressure distillation slough excessive ether and the decolouring, promptly get carboxylate;
2) building-up reactions---in carboxylate, add two polyoxyethylene alkyl amines, make carboxylate account for 30～80% of gross weight, carry out acidifying with mineral acid, the dropping time is 1 hour, 70 ℃ of temperature of reaction, slaking is 1 hour then, through vaccum dewatering, and cooling, under 50～150 ℃ of temperature, slowly drip oxyethane, the two polyoxyethylene alkyl amines of its dripping quantity: the mol ratio of oxyethane=0.5～3.5: 1.0, add afterreaction a few hours, cooling discharge gets the finished product.
According to the synthesis technique of claim 1 or 2 or 3 described PVC antistatic elasticizers, it is characterized in that 4, described diprotic acid is that general formula is the aliphatic dibasic acid of HOOC-R-COOH, wherein the carbon number of R is 1～12.
According to the synthesis technique of claim 1 or 2 or 3 described PVC antistatic elasticizers, it is characterized in that 5, the consumption of described catalyzer tosic acid is 0.1～1.5% of a principal goods material weight.
6, the synthesis technique of PVC antistatic elasticizer according to claim 4 is characterized in that, the consumption of described catalyzer tosic acid is 0.1～1.5% of a principal goods material weight.
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| CN101358126B (en) * | 2008-09-09 | 2012-05-30 | 四川大学 | Method for preparing permanent antistatic agents |
| KR20140027014A (en) | 2012-08-23 | 2014-03-06 | 주식회사 엘지화학 | Plasticizer composition |
| CN108728074A (en) * | 2018-06-29 | 2018-11-02 | 成都菲尔特技术开发有限公司 | A kind of liquid and supercritical carbon dioxide thickening switch surfactant and its compound system |
| CN111748137B (en) * | 2019-03-26 | 2022-12-02 | 杭实科技发展(杭州)有限公司 | Low-humidity-resistant antistatic agent special for polyolefin |
| CN111269502B (en) * | 2020-02-28 | 2021-11-05 | 杭实科技发展(杭州)有限公司 | Low-addition-amount long-acting low-humidity-resistant water-washing-resistant antistatic agent special for polyvinyl chloride |
| CN113214468B (en) * | 2021-06-07 | 2022-07-01 | 陕西科技大学 | Polyvinyl chloride plasticizing antistatic agent and preparation method thereof |
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