CN103772422B - A kind of boric acid monoesters as antistatic additive and preparation method thereof - Google Patents
A kind of boric acid monoesters as antistatic additive and preparation method thereof Download PDFInfo
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Abstract
The present invention relates to a kind of boric acid monoesters as antistatic additive and preparation method thereof, it is for antistatic. Should be called N as the boric acid monoesters name of antistatic additive, N-ethoxy fatty acid amine boric acid monoesters, structure is shown in general formula (I); The method of preparing this boric acid monoesters comprises three steps: the esterification of a. diethanol amine and aliphatic acid; B. the molecular clock of mono fatty acid monoethanolamine ester; C. the supercritical esterification of boric acid reaction. Boric acid monoesters Stability Analysis of Structures of the present invention, antistatic property are good, can high temperature resistant, resistance to low humidity as antistatic additive; The present invention prepares the method for boric acid monoesters, avoided borate at high temperature intramolecular dehydration cause variable color, coking and the problem that is difficult to esterification, and owing to reacting under super critical condition, the reaction time shortens greatly.
Description
Technical field
The present invention relates to a kind of boric acid monoesters and preparation method thereof, be specifically related to a kind of boric acid as antistatic additiveMonoesters and preparation method thereof.
Background technology
Most polymers material has stronger electrical insulation capability, and they have obtained widely should in many aspectsWith. But the high resistivity of polymeric material in use often easily produces build-up of static charges, these electrostatic chargesCan stop several hours even several days at polymer surfaces, cause attraction and repulsion, produce sometimes electroshock,Electric shock, even spark discharge. At present, the industrial effective method of this type of phenomenon that forfends is to add antistatic additive.
Known according to existing theory, antistatic additive is generally the organic substance with surfactant structure feature.Boracic surfactant is taking boric acid as parent, forms the compound of the borate ester of B, O key, is solely a kind ofSpecial surfactant. Boric acid construction unit is plane triangle, and each boron atom is with SP2Hydridization and oxygen atomIn conjunction with, now boron is still electron deficient structure, and the hydroxyl easily and in organic compound reacts, and after dehydration, formsBorate. According to the ratio of boric acid and hydroxy compounds and the difference of type, its can form boric acid monoesters, dibasic acid esters,Three esters and four replace spirane structure.
The method great majority that at present synthetic borate adopts are direct method, ester-interchange method and solvent method, and forBorate surfactant, most study be boric acid diglycerol mono fatty acid ester and boric acid diacylglycerol polyoxyethyleneThe cationic surfactant of mono fatty acid ester.
Dong Bang chemical industrial company of Japan utilizes glycerine and acid reaction to generate glycerine borate, then usesAliphatic acid carboxylated can obtain fatty acid ester, and the product making is widely used in fiber process, as emulsifying agent,Antistatic additive, flexible smooth agent etc. Dong Bang chemical industrial company is water-soluble in order to improve it, synthetic point three stepsCarry out: glycerine elder generation and boric acid effect, generate glycerine borate; Then introduce oxirane, play polymerization anti-Should, generate glycerine APEO; Finally, with aliphatic acid effect, make product.
Ciba company utilizes octadecylamine with glycidol two (2,3-hydroxypropyl octadecylamine) reaction, then with boronAcid reaction generates Spirocyclic product.
Chinese scholar Zhang Xiuling etc. has reported that in the Speciality Petrochemicals of the 5th phase in 1997 " boron system lives on surfaceProperty agent synthetic and performance study " literary composition, it determines glycerine, aliphatic acid, boric acid mol ratio according to esterificationFor 2:0.9:0.4, synthesize BOR; And 4 parts of alkyl alcoholamines are added to reactor, be warmed up to 60 DEG C and add5 parts of aliphatic acid, keep 60-70 DEG C, and reaction lh generates alkylolamides, then adds acid reaction to obtainBONR. Test shows: they have good diffusion permeability, emulsibility, spumescence.
In the patent CN101029151B of China's on December 8th, 2012 bulletin, disclose and to have adopted borateThe composition of antistatic additive, and disclose its synthesis technique, be: first by glycerine and the reaction of boric acid decompression esterification,Then add aliphatic acid to synthesize.
Above borate ester mainly with glycerine (glycerine) as polyol, although the source of glycerine is wideGeneral, but glycerine is aspect processing organic synthesis, and intramolecular dehydration polymerization easily occurs, and forms diester, three estersCompound, reduces the antistatic property of synthetic greatly. Specifically with regard to Chinese patent CN101029151B,Author of the present invention takes the technology identical with this patent, and the product obtaining cannot reach any antistatic effectReally; The technique that this patent discloses cannot ensure the reaction production monoesters of glycerine and boric acid, more cannot ensure follow-up mistakeWhether the aliphatic acid of amount reacts with aliphatic acid, in its structure of title compound formula, there is no hydrophilic radical, and anti-quietElectricity agent is to utilize hydrophilic radical to absorb airborne water to reach the object of moving electric charge.
Chinese scholar poplar is washed etc. at " the synthetic and character of boric acid alkylolamides ester " (fine chemistry industry, 3(13),1～27,1996) in, reported and utilized 6501 (being 2:1 type) lauric acid amide of ethanol and boric acid not on year-on-year basisUnder example, synthesize boric acid alkylamide ester, belonged to boron oxa-ring surface activating agent through characterizing this product, both belonged to non-Ionic surface active agent has again some characteristic of anion surfactant, has the capillary performance of reductionStronger emulsifying ability.
Chinese scholar Wang Hui quick " ricinoleic alkyl alcohol amide borate synthetic and application study " (fine chemistry industry,6(16), 24～27,1999) in, utilize castor oil, diethanol amine and boric acid are that raw material has synthesized castor oil alkaneAlkylolamides borate. This synthesis technique, can take off in molecule under residual diethanol amine (not molecular clock) high temperatureWater, causes monoester content low; Synthetic product makes an addition in polyethylene, only taking poly mass ratio as 2%Make its sheet resistance drop to 109Ω, the antistatic property of visible product is very low.
Summary of the invention
The object of the present invention is to provide a kind of boric acid monoesters as antistatic additive, this boric acid monoesters antistatic additiveStability Analysis of Structures, antistatic property are good, and high temperature resistant, resistance to low humidity.
Correspondingly, another object of the present invention is to provide a kind of above-mentioned boric acid as antistatic additive of preparingThe method of monoesters.
Boric acid monoesters as antistatic additive provided by the invention, its name is called N, N-ethoxy fatty acid amine boronAcid monoester, its structure is shown in general formula (I):
Wherein R is C12～C22Straight chain or branched saturated or unsaturated alkyl.
The above-mentioned boric acid monoesters as antistatic additive, the preferred C of R in general formula (I)15～C17Straight chain or branchedSaturated or unsaturated alkyl, most preferred R is C15Or C17Straight chain saturation alkane base.
The method of preparing the above-mentioned boric acid monoesters as antistatic additive, comprises following three step (following force valueFront "-" only represents vacuum, and for example " 0.06～-0.1Mpa " expression vacuum is 0.06～0.1Mpa):
The esterification of step a. diethanol amine and aliphatic acid: the diethanol amine that is 2.2～2.8:1 by mol ratio(seeing structural formula I) drops in reactor with aliphatic acid, is under the pressure of-0.06～-0.1Mpa at vacuum conditionCarry out esterification, the temperature of esterification is 100 DEG C～180 DEG C, and esterification time is 2～8 hours, withTime reactor stir with the speed of 400～1000r/min (r/min represent rev/min). Diethanol amine and aliphatic acidCarbonyl displacement has occurred in esterification reaction process, and the principle of the silver mirror reaction of carbonyl, this esterification are followed in reactionObtain mono fatty acid monoethanolamine ester (seeing general formula II) and bis-fatty acid monoethanolamine ester (seeing general formula III) mixture.
The molecular clock of step b. mono fatty acid monoethanolamine ester: will (fall after the mixture cooling of step a gainedTemperature after temperature, without specific requirement, can be made as 60～120 DEG C), be driven in molecular clock system and carry out threeLevel molecular clock, obtains mono fatty acid monoethanolamine ester; The temperature of first order molecular clock is 120 DEG C～140 DEG C,Vacuum pressure is :-0.08～-0.1Mpa; The temperature of second level molecular clock is 140 DEG C～160 DEG C, vacuumPressure is :-1000～-10pa; The temperature of third level molecular clock is 160 DEG C～180 DEG C, and vacuum pressure is:-50～-0.1pa; In three grades of molecule still-process, blade applicator rotating speed is 50r/min left and right.
The supercritical esterification reaction of step c boric acid: the boric acid that is 2～10:1 by mol ratio and above-mentioned steps bThe mono fatty acid monoethanolamine ester of gained is put in overcritical synthesis reactor, esterification at the temperature of 10 DEG C～40 DEG C10～50 minutes, obtain N, N-ethoxy fatty acid amine boric acid monoesters; Supercritical reaction medium is carbon dioxide,Supercritical pressure is: 18～25Mpa.
In above-mentioned steps a, the preferred molar ratio of described diethanol amine and aliphatic acid is 2.4～2.6:1, vacuumPressure preferred value is-0.08～-0.1Mpa, and esterification temperature is preferably 140 DEG C～160 DEG C, and esterification time is preferredValue is 3～5 hours, and reactor mixing speed recommendation is 600～8000r/min.
Aliphatic acid described in step a, its alkyl is C12～C22Straight chain or branched saturated or unsaturated hydrocarbonsBase, preferably C15～C17, for example, aliphatic acid can be stearic acid, palmitic acid. Above-mentioned aliphatic acid can derive from waterThe grease of separating, as the hydrolysate of tallow or vegetable fat.
Detect through chromatogram, find in mixture that above-mentioned steps a esterification makes mono fatty acid monoethanolamine ester andBis-fatty acid monoethanolamine ester respectively accounts for 50%. Meanwhile, detect also and find by chromatogram, through above-mentioned steps bThree grades of molecular clocks after, the content of gained mono fatty acid monoethanolamine ester is more than 90%.
The preferred molar ratio of the boric acid described in above-mentioned steps c and mono fatty acid monoethanolamine ester is 6～8:1, esterificationTemperature preferred value is 20 DEG C～30 DEG C, and esterification time is preferably 20～30 minutes, and supercritical pressure is preferably20～22Mpa。
Upper step c is the esterification of carrying out under super critical condition, and it is non-toxic and not that supercritical fluid hasCombustion property, it is as reaction medium, and not only solvability is high, diffusion coefficient is large, and can effectively control reaction and liveProperty and selective. Under super critical condition, accelerated by the homogeneous reaction speed of diffusion rate control, simultaneously pressureThe impact of reaction rate constant is strengthened. In addition the chemical reaction carrying out under super critical condition, can also realization responseWith the coupling separating: in supercritical fluid, the solubility of solute is with its relative molecular mass, temperature and pressureChange have obvious variation, can utilize this character in time product to be removed from reaction system, withObtain larger conversion ratio.
The invention has the advantages that: reactant diethanol amine of the present invention is more stable compared with glycerine, be not easy to send outPolymerization in son estranged; The present invention makes with diethanol amine the boric acid monoesters that reactant generates, because it is for containing nitrogen elementBoric acid structure, therefore be the most stable borate ester; Again because this boric acid monoesters contains boric acid hydroxyl and long-chainAlkyl, good as antistatic additive antistatic property, and can high temperature resistant, resistance to low humidity. In addition, the present invention adopts woundThe technological design of new property, is used supercritical extract reactor, make reactant in supercritical carbon dioxide in oftenTemperature lower reaction, avoided borate at high temperature intramolecular dehydration cause variable color, coking and the problem that is difficult to esterification;And under super critical condition, react, the reaction time shortens greatly.
Detailed description of the invention
Further illustrate the present invention below by embodiment and application examples. In embodiment in three grades of molecule still-processBlade applicator rotating speed is 50r/min, and the medium of supercritical esterification reaction is carbon dioxide. Each embodiment's is anti-Answer parameter in table 1.
Embodiment 1
Boric acid monoesters as antistatic additive is: N, and N-ethoxy Stearyl Amine boric acid monoesters, its structural formula is willN, the R in N-ethoxy fatty acid amine boric acid monoesters general formula (I) is changed to n-heptadecane base, specifically sees structural formula（Ⅱ）。
N, the preparation method of N-ethoxy Stearyl Amine boric acid monoesters is:
Step a: take 56 kilograms of 50 kilograms of diethanol amine, stearic acid (diethanol amine and stearic moleThan for 2.4::1), put in the reactor of 200 kilograms, at vacuum condition be-enter under the pressure of 0.1MpaRow esterification, esterification temperature is 140 DEG C, and esterification time is 4 hours, and reactor speed of agitator is 700R/min, obtains monostearate monoethanolamine ester and two stearic acid monoethanolamine ester admixture through reaction.
Step b: cool to 100 DEG C after esterification is complete, step a reaction gained mixture is driven into molecular clockIn system, carry out three grades of molecular clocks, keeping first order molecular clock temperature is 130 DEG C, and vacuum is-0.1Mpa, blade applicator rotating speed is 50r/min; Second level molecular clock temperature is 150 DEG C, and vacuum is-100pa,Blade applicator rotating speed is 50r/min; Third level molecular clock temperature is 170 DEG C, and vacuum pressure is-5pa, knifingDevice rotating speed 50r/min. After three grades of molecular clocks, obtain the monostearate monoethanolamine that 55.4 kilograms of content are 95%Ester.
Step c: by 55.4 kilograms of monostearate monoethanolamine esters of above-mentioned steps b gained and 54 kilograms of boric acid (boronAcid is 5.9:1 with the mol ratio of monostearate monoethanolamine ester) put in 100 liters of overcritical synthesis reactors and carry out esterChange reaction. The temperature of synthesis reactor is 25 DEG C, and esterification time is 25 minutes; Supercritical reaction medium is titanium dioxideCarbon, supercritical pressure is 21Mpa, obtains final products N after reaction, N-ethoxy Stearyl Amine boric acid monoesters98.6 kilograms.
Embodiment 2
Boric acid monoesters as antistatic additive is: N, and N-ethoxy palm acid amide boric acid monoesters, its structural formula is willN, the R in N-ethoxy fatty acid amine boric acid monoesters general formula (I) is changed to n-pentadecane base, specifically sees structureFormula (III):
N, the preparation method of N-ethoxy palm acid amide boric acid monoesters is:
Step a: take 50 kilograms of diethanol amine and 52 kilograms of palmitic acids (diethanol amine and palmitic acid moleThan for 2.3:1), put in the reactor of 200 kilograms, under vacuum condition, carry out esterification. Vacuum PressurePower, esterification temperature, esterification time, reactor mixing speed, in table 1, obtain single palmitic acid monoethanolamine through reactionEster and two palmitic acid monoethanolamine ester admixture.
Step b: cool to 100 DEG C after esterification is complete, step a reaction gained mixture is driven into molecular clockIn system, carry out three grades of molecular clocks. In three grades of molecule still-process, blade applicator rotating speed is 50r/min, eachThe quality of gained list palmitic acid monoethanolamine ester and containing after level molecule vapo(u)rizing temperature, vacuum pressure, three grades of molecular clocksAmount is in table 1.
Step c: boric acid and step b gained list palmitic acid monoethanolamine ester are put into 100 liters of overcritical synthesis reactorsIn carry out esterification. Mol ratio, esterification temperature, the ester of boric acid quality, boric acid and single palmitic acid monoethanolamine esterChange time, supercritical pressure are in table 1. Above-mentioned reactant carries out after supercritical esterification reaction in carbon dioxide,Obtain final products N, 103.8 kilograms of N-ethoxy palm acid amide boric acid monoesters.
Embodiment 3
Boric acid monoesters as antistatic additive is: N, and N-ethoxy 11-methyl dodecane acid amide boric acid monoesters, itsStructural formula (IV) is:
N, the preparation method of N-ethoxy 11-methyl dodecane acid amide boric acid monoesters is:
Repeat embodiment 2 according to Parameter Conditions in table 1, but with 11-methyl dodecylic acid replacement palmitic acid,The quality of diethanol amine and 11-methyl dodecylic acid is respectively 50 kilograms, 46.2 kilograms, and the mol ratio of the two is2.2:1; After step a, b, c, finally obtain N, N-ethoxy 11-methyl dodecane acid amide boric acid monoesters68 kilograms.
Embodiment 4
Boric acid monoesters as antistatic additive is: N, N-ethoxy DHA amine boric acid monoesters, its knotStructure formula (V) is:
N, the preparation method of N-ethoxy DHA amine boric acid monoesters is:
Repeat embodiment 2 according to the Parameter Conditions in table 1, but replace brown with DHA (DHA)Palmitic acid acid, the quality of diethanol amine and DHA is respectively 50 kilograms, 55.8 kilograms, the two rubYou are than being 2.8:1; After step a, b, c, finally obtain N, N-ethoxy DHA amine boron110 kilograms of acid monoesters.
Table 1
Application examples
Make 15% master batch with preparing gained boric acid monoesters in embodiment 1,15 parts of boronic acid containing monoesters in master batch,85 parts, PVC material, it is normally extruded with twin-screw. Master batch is added in PVC to preparation experiment sample.The sample making is that (it adopts the Hai Tian molding machine company sharp injection machine in sky to the thick white injection moulding PVC sheet material of 3mmTR-D03 makes), its size is 10 × 10cm; In laboratory sample, contain antistatic additive 1%, nano-calcium carbonate 5%,Proportioning 94% HHP3-PP of China Petrochemical Industry.
Replace the boric acid list of preparing gained in embodiment 1 with Armostat600 (production of Aksu-Nobel company)Ester, prepares control sample with above-mentioned same procedure.
Using laboratory sample and control sample as test sample, test its sheet resistance. Testing standard is: " GB1410 solid insulating material specific insulations and surface resistivity test method ", " SJ/T10694 electronic productManufacture anti-static system method of testing "; Tester is: the limited public affairs of HY-779(Tianjin this measuring technology of NicoDepartment).
Sample test Pretreatment is: represent relative humidity at 50%RH(RH), place 12 at 20 DEG CHour. The test result of laboratory sample and control sample sheet resistance (unit is Ω, and Ω represents ohm) is as follows:One, water-fastness test
When water-fastness test, the sample through above-mentioned pre-treatment is soaked to 1h in 20 DEG C of distilled water, test itThe sheet resistance of soaking (washing) front and back in water, test result is in table 2.
Table 2
| Laboratory sample sheet resistance/Ω | Control sample sheet resistance/Ω | |
| Before washing | 108 | 1010-1011 |
| After washing | 108-109 | 1010-1011 |
Two, weather-proof test
While carrying out weather-proof test, first will under 80 DEG C, 20%RH condition, place 3 days through the sample of pre-treatmentTest it and placed before 3 days and the sheet resistance of placing different time after 3 days, test result is in table 3.
Table 3#
| Laboratory sample sheet resistance/Ω | Control sample sheet resistance/Ω | |
| Before processing | 108 | 1010-1011 |
| Process latter 1 day | 108-109 | 1010-1011 |
| Process latter 7 days | 108-109 | 1011-1012 |
| Process latter 14 days | 108-109 | 1011 |
| Process latter 30 days | 108-109 | Nothing |
| Process latter 60 days | 109-1010 | Nothing |
#: the processing in table refers to place 3 days under 80 DEG C, 20%RH condition.
Three, normal temperature humidity measurement
Respectively test through the sample of pre-treatment at 20 DEG C in 20%RH, 60%RH, 80%RH, 100%RHUnder condition, place the sheet resistance after 24h, test result is in table 4.
Table 4
| Placement condition | Laboratory sample sheet resistance/Ω | Control sample sheet resistance/Ω |
| Before placement | 108 | 1010-1011 |
| 20%RH | 109-1010 | 1011 |
| 60%RH | 109 | 1011 |
| 80%RH | 109 | 1011 |
| 100%RH | 109 | 1010 |
Can find out from the data of table 2～table 4, product of the present invention has outstanding antistatic property, specialUnder the condition of low humidity.
Claims (7)
1. prepare the method as the boric acid monoesters of antistatic additive, its feature with: preparation N, N-ethoxy fatThe method of fat acid amide boric acid monoesters comprises the following steps:
A) esterification of diethanol amine and aliphatic acid: the diethanol amine that is 2.2～2.8:1 by mol ratio and fatFat acid drops in reactor, at vacuum condition is to carry out esterification under the pressure of-0.06～-0.1Mpa,The temperature of esterification is 100 DEG C～180 DEG C, and esterification time is 2～8 hours, and simultaneous reactions still is with 400The speed of～1000 revs/min stirs, and esterification obtains mono fatty acid monoethanolamine ester and bis-fatty acid monoethanolamineEster admixture;
B) molecular clock of mono fatty acid monoethanolamine ester: by after the mixture cooling of step a gained, be driven into pointIn sub-Distallation systm, carry out three grades of molecular clocks, obtain mono fatty acid monoethanolamine ester; First order molecular clockTemperature be 120 DEG C～140 DEG C, vacuum pressure is :-0.08～-0.1Mpa; Second level molecular clockTemperature is 140 DEG C～160 DEG C, and vacuum pressure is :-1000～-10pa; The temperature of third level molecular clockDegree is 160 DEG C～180 DEG C, and vacuum pressure is :-50～-0.1pa; Knifing in three grades of molecule still-processDevice rotating speed is 50 revs/min;
C) supercritical esterification of boric acid reaction: the boric acid that is 2～10:1 by mol ratio and above-mentioned steps b gainedMono fatty acid monoethanolamine ester is put in overcritical synthesis reactor, esterification 10 at the temperature of 10 DEG C～40 DEG C～50 minutes, obtain N, N-ethoxy fatty acid amine boric acid monoesters; Supercritical reaction medium is titanium dioxideCarbon, supercritical pressure is: 18～25Mpa.
2. a kind of method of preparing as the boric acid monoesters of antistatic additive according to claim 1, its feature existsIn: the mol ratio of diethanol amine described in step a and aliphatic acid is 2.4～2.6:1, and vacuum pressure is-0.08～-0.1Mpa, reactor mixing speed is 600～8000 revs/min.
3. a kind of method of preparing as the boric acid monoesters of antistatic additive according to claim 1, its feature existsIn: the esterification temperature described in step a is 140 DEG C～160 DEG C, and esterification time is 3～5 hours.
4. a kind of method of preparing as the boric acid monoesters of antistatic additive according to claim 1, its feature existsIn: the mol ratio of the boric acid described in step c and mono fatty acid monoethanolamine ester is 6～8:1.
5. a kind of method of preparing as the boric acid monoesters of antistatic additive according to claim 4, its feature existsIn: the esterification temperature described in step c is 20 DEG C～30 DEG C.
6. a kind of method of preparing as the boric acid monoesters of antistatic additive according to claim 4, its feature existsIn: the esterification time described in step c is 20～30 minutes.
7. a kind of method of preparing as the boric acid monoesters of antistatic additive according to claim 4, its feature existsIn: the supercritical pressure described in step c is 20～22Mpa.
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| CN105859552A (en) * | 2016-05-25 | 2016-08-17 | 张秀勇 | Synthesis and purification method of propanediol lactate |
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| CN105949055A (en) * | 2016-05-25 | 2016-09-21 | 张秀勇 | Method for synthesizing and purifying glycerin lactate |
| CN107353220B (en) * | 2017-08-09 | 2023-05-16 | 赞宇科技集团股份有限公司 | Process and device for continuously producing fatty acid alkanolamide by taking fatty acid as raw material |
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