CN108774296A - A kind of preparation method of modified petroleum resin - Google Patents
A kind of preparation method of modified petroleum resin Download PDFInfo
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- CN108774296A CN108774296A CN201810721743.6A CN201810721743A CN108774296A CN 108774296 A CN108774296 A CN 108774296A CN 201810721743 A CN201810721743 A CN 201810721743A CN 108774296 A CN108774296 A CN 108774296A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
Abstract
The invention belongs to Petropols production technical fields, and in particular to a kind of preparation method of modified petroleum resin.A kind of preparation method of modified petroleum resin; using mixture one or more of in petroleum cracking by-product C 5 fraction, C9 fractions, dicyclopentadiene fraction and other fractions rich in unsaturated olefin as raw material; through thermal polymerization; it is isolated molten state Petropols; under inert gas protection; polar functional group modification is introduced, the polarity of Petropols molecule is increased, changes chemical property；Then it is fully dissolved with hydrogen solvent is added, obtains Petropols solution；Above-mentioned Petropols solution is conveyed into the reactor with hydrogenation catalyst together with hydrogen, selective hydrogenation is carried out and obtains modified petroleum resin.Modified petroleum resin prepared by this method have many advantages, such as shallow, tasteless, solvent the intermiscibility of color it is good, with the compatibility of polar resin is good, thermostabilization and oxidative resistance are good, meet client's multiscale demand, improve economic benefit.
Description
Technical field
The invention belongs to Petropols production technical fields, and in particular to a kind of preparation method of modified petroleum resin.
Background technology
At present there are mainly two types of the polymerization techniques in Petropols preparation process：1, polymerization processes therewith, its advantage is that raw
The molecular resin amount narrowly distributing of production, dissolubility in a solvent is preferable, and smell is smaller.The disadvantage is that needing to use catalyst, catalysis
Agent has certain danger and toxicity；And the catalyst of present Resin Industry handle will urge after the completion of polymerization from polymer fluid
Agent removes, and a large amount of waste water and waste residue are generated in subtractive process, and processing cost is high；Catalyst amount is larger, higher price, raw
It produces of high cost.2, thermal polymerization process：Advantage is to be not required to catalyst, and production process does not generate waste water and dregs, simple for process at low cost.
The disadvantage is that the molecular resin amount distribution of production is wide, has in common solvent that insoluble matter, poor transparency, photo and thermal stability be poor, smell
Greatly；Especially photo and thermal stability is poor, smell limits greatly its application field.The Petropols of both the above polymerization production
There are two common ground, first, have a large amount of unsaturated bond, stability poor, second is that all by it is hydrocarbon form, resin polarity it is small, attached
Put forth effort relatively low.
In order to improve the performance of Petropols, need to be modified it, modified method is mainly divided to two kinds：One is with
The method of hydrogen is added to be modified, main purpose is to reduce form and aspect in order to eliminate the residual double bonds and aromatic ring in Petropols molecule, improve
Thermal stability, weatherability etc., major defect are since resin saturation degree rises, cohesive force is deteriorated, with the phases such as EVA, SIS, SBS
Capacitive is decreased obviously, and adhesive force declines；Hydroconversion condition needs carry out under the conditions of high temperature, high pressure and high activated catalyst, equipment
Invest danger that is larger, and having certain.Patent CN1485352A, CN1485353A discloses a kind of dicyclopentadiene hydrogenated stone
The preparation method and its catalyst of oleoresin, although hydrogenated petroleum resin thermal stability, oxidation stability and form and aspect obtained obtain
Improve to corresponding, but is decreased obviously with polar resin compatibility performance；Another method of modifying is to introduce functional group modification, one
As refer to introducing to be modified with the monomer of polar functional group.Such as a kind of acid-modified petroleum resin patent
CN200480018371.7 is led in the Petropols based on the ethylenically unsaturated hydrocarbons monomer with carbon atom number 4~6
Enter from 8 ethylenic unsaturated carboxylic acid below of carbon atom number or the carboxyl of its acid anhydrides or the sour modified petroleum tree of anhydride group
Fat, which has preferable mobility and compatibility, but form and aspect are deeper, and smell is larger；Its Petropols before modified is catalysis
It polymerize synthesis technology, production cost is higher.
Invention content
It is an object of the invention to provide a kind of preparation side of modified petroleum resin for problems of the prior art
Method, modified petroleum resin prepared by this method have shallow, tasteless, solvent the intermiscibility of color it is good, with the compatibility of polar resin it is good,
The advantages that thermostabilization and good oxidative resistance, meets client's multiscale demand, improves economic benefit.
The technical scheme is that：
A kind of preparation method of modified petroleum resin, includes the following steps:
(1) prepared by base resin, by C 5 fraction, C9 fractions, the dicyclopentadiene fraction and other in petroleum cracking product
One or more of mixtures are raw material in fraction rich in unsaturated olefin, are added in the reaction kettle with blender, carry out heat
Unpolymerized component and oligomer is distilled off in polymerisation, then isolated molten state basis Petropols；
(2) polar functional group modification reacts, by the molten state Petropols obtained in above-mentioned steps in inert gas shielding
Under, the monomer with polar functional group is added and carries out functional group modification reaction, increases the polarity of Petropols molecule, changes chemistry
Property obtains the functional group modification Petropols of molten condition；
(3) hydrogenation modification reacts, by the functional group modification Petropols of the molten condition obtained in above-mentioned steps and plus hydrogen
After solvent is mixed by quality 1 to 0.5~4, it is conveyed into together with hydrogen in the reactor with hydrogenation catalyst, in hydrogenation catalyst
Selective hydrogenation is carried out under the catalysis of agent, solvent and oligomer are removed by rectification under vacuum after reaction, and one kind is made
Modified petroleum resin.
Specifically, the condition of the heat polymerization is：180~280 DEG C, 0.2~3.5MPa of pressure of temperature, time 2
~50 hours.
Specifically, the basic Petropols of the molten condition are under inert gas protection, introduce polar functional group and change
Property reaction, reaction temperature be 140~260 DEG C, 10 minutes~10 hours reaction time.
Specifically, the dosage with polar functional group monomer is the 0.2~10% of molten state Petropols quality.
Specifically, the condition of the hydrogenation reaction is：Temperature is 100~250 DEG C, and pressure is 2.0~14.0MPa, instead
It is 0.2~6h between seasonable.
Specifically, the monomer with polar functional group is acrylic acid, methacrylic acid, butenoic acid, ethyl propylene
The ethylenic bonds unsaturated monocarboxylic such as acid；The ethylene linkages such as maleic acid, itaconic acid, citraconic acid, maleic anhydride, itaconic anhydride, citraconic anhydride
Formula unsaturation polybasic carboxylic acid and its acid anhydrides；The ethylenic bonds unsaturation polybasic carboxylic acid such as monomethyl maleate, monomethyl ester it is inclined
One kind in ester.
Specifically, described plus hydrogen solvent is n-hexane, normal heptane, hexamethylene, hexahydrotoluene, ethyl cyclohexane, adds
A kind of or several combination in hydrogen cracking aviation kerosine, solvent naphtha.
The beneficial effects of the invention are as follows：(1) base resin is Petropols made from thermal polymerization, pollution-free, at low cost；
The Petropols of molten condition after heat polymerization carry out addition reaction with the monomer with polar functional group immediately, make production
Expense reduces, because needing substantially without outer heat or only few heat, heats and convey related energy consumption and equipment with auxiliary
Expense also reduces；(2) hydrogenation modification reacts, and is that selective hydrogenation is carried out in the presence of hydrogenation catalyst, and selectivity adds
Hydrogen reacts general temperature, pressure than adding hydrogen low entirely, and low-temp low-pressure, low energy consumption, danger are small, at low cost；(3) plus hydrogen solvent can be with
For boiling point in the solvent naphtha of 70~250 DEG C (without containing halogens and sulphur such as chlorine atom, bromine atom), dissolubility is good, loss is easy to less
It recycles, price is low is easy to buy；(4) modified petroleum resin made from has the two kinds of modifications of functional group modification and hydrogenation modification
The advantages of Petropols：It is tasteless, form and aspect are shallow, good thermal stability, photostability, also have adhesive property it is good, with natural rubber
Glue (NR), synthetic rubber, styrene polymer (such as SIS, SBS, SEBS), EVA have good compatibility, with natural thickening
Resin is (such as：Terpenes, rosin and its derivative) compatibility is also good.The modified petroleum resin that the method provided through the invention makes
It can be widely applied to road marking paint, extraordinary adhesive, high-grade rubber, high-grade ink, papermaking, adhesive, amenities, medical
In the industries such as container and packaging material additive.
Specific implementation mode
The present invention provides a kind of preparation method of modified petroleum resin, includes mainly three steps：One, base resin system
It is standby：With in the C 5 fraction of petroleum cracking by-product, C9 fractions, dicyclopentadiene fraction and other fractions rich in unsaturated olefin one
Kind or several mixtures are raw material, are added in the reaction kettle with blender, 180~280 DEG C of hot polymerization reaction temperature, pressure
0.2~3.5MPa, reaction time 2~50 hours, polymerisation can be intermittent reaction, can also be successive reaction, polymerization knot
Beam distills out the basic Petropols that unpolymerized component and oligomer obtain molten condition；Two, polar functional group modification：Lazy
Property gas shield under, in the Petropols of the molten condition obtained into above-mentioned steps, be added with polar functional group monomer
Carry out functional group modification reaction, with polar functional group monomer dosage be molten condition Petropols quality 0.2~
10%, 140~260 DEG C of reaction temperature, the reaction time 10 minutes~10 hours, obtains the functional group modification resin of molten condition；
Three, hydrogenation modification reacts：The functional group modification Petropols for the molten condition that above-mentioned steps are made press quality 1 with hydrogen solvent is added
After 0.5~4 mixing, it is conveyed into together with hydrogen in the reactor with hydrogenation catalyst, in the presence of hydrogenation catalyst
Selective hydrogenation is carried out, hydrogenation temperature is 100~250 DEG C, and reactive hydrogen presses 2.0~14MPa, and the reaction time is 0.2~6h,
Solvent and oligomer are removed by rectification under vacuum after reaction, and a kind of modified petroleum resin is made, solvent is Ke Xunhuanliyong.
In order to which clearer explanation method provided by the invention is described in detail by following embodiment, in following implementation
The test method of each index of the modified petroleum resin made in example is as follows：
Softening point：Ring and ball method (GB/T4507)；
Form and aspect：ASTM D-1544；
Bromine number：GB/T24138-2009 appendix As；
Melt viscosity (200 DEG C)：ASTM D-3236；
Acid value：GB/T 2895.
Embodiment 1
In autoclaves of the 5L with blender, thick dicyclopentadiene 1900g, the C 5 fraction that purity is 83% is added
900g and toluene 1000g, stirs evenly, and is to slowly warm up to 260 DEG C, reaction pressure 2.0MPa, after being reacted 6 hours at 260 DEG C,
First air-distillation goes out unpolymerized light component, then is evaporated under reduced pressure out oligomer, obtains the basic Petropols liquid of molten condition
2000g；Under nitrogen protection, 26g modifying agent maleic anhydrides are added, addition reaction in 2 hours, the stone after addition are carried out at 200 DEG C
Oleoresin fully dissolves after being mixed with 6000g solvent naphthas, obtains functional group modification Petropols solution；By above-mentioned functional group modification
Petropols solution is conveyed into the reactor with hydrogenation catalyst together with hydrogen, carries out adding hydrogen in the presence of a hydrogenation catalyst
Reaction, for controlling reaction temperature at 140 DEG C, reactive hydrogen presses 4.0MPa, obtains modified Petropols solution, above-mentioned modified
Petropols solution is -0.098MPa by pressure, and temperature is that 240 DEG C of rectifications under vacuum remove solvent and oligomer, is modified
Petroleum resin products, product carry out index analysis such as the following table 1.
Product index analytical table 1
Embodiment 2
In autoclaves of the 5L with blender, thick dicyclopentadiene 1900g, the C 5 fraction that purity is 83% is added
900g and toluene 1000g, stirs evenly, and is to slowly warm up to 260 DEG C, reaction pressure 2.0MPa, after being reacted 6 hours at 260 DEG C,
First air-distillation goes out unpolymerized light component, then is evaporated under reduced pressure out oligomer, obtains the basic Petropols of molten condition
2000g；Under nitrogen protection, 26g modifying agent maleic anhydrides are added, addition reaction in 2 hours, the stone after addition are carried out at 200 DEG C
Oleoresin fully dissolves after being mixed with 6000g solvent naphthas, obtains functional group modification Petropols solution；By above-mentioned functional group modification
Resin solution is conveyed into the reactor with hydrogenation catalyst together with hydrogen, carries out in the presence of a hydrogenation catalyst plus hydrogen is anti-
It answers, for controlling reaction temperature at 160 DEG C, reactive hydrogen presses 4.0MPa, obtains modified Petropols solution, will be above-mentioned modified
Petropols solution is -0.098MPa by pressure, and temperature is that 240 DEG C of rectifications under vacuum remove solvent and oligomer, is modified
Petroleum resin products, product carry out index analysis such as the following table 2.
Product index analytical table 2
Embodiment 3：
In autoclaves of the 5L with blender, thick dicyclopentadiene 1900g, the C 5 fraction that purity is 83% is added
900g and toluene 1000g, stirs evenly, and is to slowly warm up to 260 DEG C, reaction pressure 2.0MPa, after being reacted 6 hours at 260 DEG C,
First air-distillation goes out unpolymerized light component, then is evaporated under reduced pressure out oligomer, obtains the basic Petropols of molten condition
2000g；Under nitrogen protection, 26g modifying agent maleic anhydrides are added, addition reaction in 2 hours, the stone after addition are carried out at 200 DEG C
Oleoresin fully dissolves after being mixed with 6000g solvent naphthas, obtains functional group modification Petropols solution；By above-mentioned functional group modification
Resin solution is conveyed into the reactor with hydrogenation catalyst together with hydrogen, carries out in the presence of a hydrogenation catalyst plus hydrogen is anti-
It answers, for controlling reaction temperature at 200 DEG C, reactive hydrogen presses 4.0MPa, obtains modified Petropols solution, above-mentioned modified stone
Oleoresin solution is -0.098MPa by pressure, and temperature is that 240 DEG C of rectifications under vacuum remove solvent and oligomer, obtains modified stone
Oleoresin product, product carry out index analysis such as the following table 3.
Product index analytical table 3
Embodiment 4：
5L with blender autoclave in, be added fractionation after nine 3000g of Beijing carbon, stir evenly, slowly
240 DEG C, reaction pressure 0.9MPa are warming up to, after being reacted 12 hours at 240 DEG C, first air-distillation goes out unpolymerized light component,
It is evaporated under reduced pressure out oligomer again, obtains the basic Petropols 2200g of molten condition；Under nitrogen protection, 28.6g is added to be modified
Agent maleic anhydride, addition reaction in 2 hours is carried out at 220 DEG C, and the Petropols after addition are fully molten after being mixed with 6600g solvent naphthas
Solution, obtains functional group modification Petropols solution；Above-mentioned functional group modification Petropols solution is conveyed into band together with hydrogen
There is the reactor of hydrogenation catalyst, carry out hydrogenation reaction in the presence of a hydrogenation catalyst, controlling reaction temperature is at 200 DEG C, reaction
Hydrogen presses 4.0MPa, obtains modified Petropols solution, above-mentioned modified Petropols solution, be by pressure-
0.098MPa, temperature are that 240 DEG C of rectifications under vacuum remove solvent and oligomer, obtain modified petroleum resin product, product is referred to
Mark is analyzed as follows table 4.
Product index analytical table 4
Embodiment 5
5L with blender autoclave in, be added fractionation after nine 3000g of Beijing carbon, stir evenly, slowly
240 DEG C, reaction pressure 0.9MPa are warming up to, after being reacted 12 hours at 240 DEG C, first air-distillation goes out unpolymerized light component,
It is evaporated under reduced pressure out oligomer again, obtains the basic Petropols 2200g of molten condition；Under nitrogen protection, 28.6g is added to be modified
Agent maleic anhydride, addition reaction in 2 hours is carried out at 220 DEG C, and the Petropols after addition are fully molten after being mixed with 6600g solvent naphthas
Solution, obtains functional group modification Petropols solution；Above-mentioned functional group modification Petropols solution is conveyed into band together with hydrogen
There is the reactor of hydrogenation catalyst, carry out hydrogenation reaction in the presence of a hydrogenation catalyst, controlling reaction temperature is at 200 DEG C, reaction
Hydrogen presses 8.0MPa, obtains modified Petropols solution, above-mentioned modified Petropols solution, be by pressure-
0.098MPa, temperature are that 240 DEG C of rectifications under vacuum remove solvent and oligomer, obtain modified petroleum resin product, product is referred to
Mark is analyzed as follows table 5.
Product index analytical table 5
Finally it should be noted that:The above embodiments are merely illustrative of the technical scheme of the present invention and are not intended to be limiting thereof；To the greatest extent
The present invention is described in detail with reference to preferred embodiments for pipe, those of ordinary skills in the art should understand that：Still
It can modify to the specific implementation mode of the present invention or equivalent replacement is carried out to some technical characteristics；Without departing from this hair
The spirit of bright technical solution should all cover within the scope of the technical scheme claimed by the invention.
Claims (7)
1. a kind of preparation method of modified petroleum resin, which is characterized in that include the following steps:
(1) prepared by base resin, by petroleum cracking product C 5 fraction, C9 fractions, dicyclopentadiene fraction and other be rich in
One or more of mixtures are raw material in the fraction of unsaturated olefin, are added in the reaction kettle with blender, carry out thermal polymerization
Reaction, is distilled off unpolymerized component and oligomer, then isolated molten state basis Petropols；
(2) polar functional group modification reacts, and under inert gas protection by the molten state Petropols obtained in above-mentioned steps, adds
Enter the monomer with polar functional group and carry out functional group modification reaction, increase the polarity of Petropols molecule, changes chemical property,
Obtain the functional group modification Petropols of molten condition；
(3) hydrogenation modification reacts, by the functional group modification Petropols of the molten condition obtained in above-mentioned steps and plus hydrogen solvent
After being mixed by quality 1 to 0.5~4, it is conveyed into together with hydrogen in the reactor with hydrogenation catalyst, in hydrogenation catalyst
Catalysis is lower to carry out selective hydrogenation, removes solvent and oligomer by rectification under vacuum after reaction, a kind of modification is made
Petropols.
2. the preparation method of modified petroleum resin according to claim 1, which is characterized in that the item of the heat polymerization
Part is：180~280 DEG C, 0.2~3.5MPa of pressure of temperature, 2~50 hours time.
3. the preparation method of modified petroleum resin according to claim 1, which is characterized in that the basis of the molten condition
Petropols under inert gas protection, introduce polar functional group modification's reaction, and reaction temperature is 140~260 DEG C, the reaction time
10 minutes~10 hours.
4. the preparation method of modified petroleum resin according to claim 1, which is characterized in that described carries polar functional group
The dosage of monomer is the 0.2~10% of molten state Petropols quality.
5. the preparation method of modified petroleum resin according to claim 1, which is characterized in that the condition of the hydrogenation reaction
It is：Temperature is 100~250 DEG C, and pressure is 2.0~14.0MPa, and the reaction time is 0.2~6h.
6. the preparation method of modified petroleum resin according to claim 1, which is characterized in that described carries polar functional group
Monomer be the ethylenic bonds unsaturated monocarboxylic such as acrylic acid, methacrylic acid, butenoic acid, ethylacrylic acid；Maleic acid, clothing health
The ethylenic bonds unsaturation polybasic carboxylic acid such as acid, citraconic acid, maleic anhydride, itaconic anhydride, citraconic anhydride and its acid anhydrides；Maleic acid list first
One kind in the partial ester of the ethylenic bonds unsaturation polybasic carboxylic acid such as ester, monomethyl ester.
7. the preparation method of modified petroleum resin according to claim 1, which is characterized in that described plus hydrogen solvent be just oneself
Alkane, normal heptane, hexamethylene, hexahydrotoluene, ethyl cyclohexane, be hydrocracked in aviation kerosine, solvent naphtha it is a kind of either
Several combinations.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109880109A (en) * | 2019-01-28 | 2019-06-14 | 陶乐敏 | A kind of aromatic modified Petropols and preparation method thereof |
| CN111187383A (en) * | 2020-02-19 | 2020-05-22 | 濮阳市瑞森石油树脂有限公司 | Preparation method of hydrogenated low-softening-point petroleum resin |
| CN112795006A (en) * | 2020-12-02 | 2021-05-14 | 宁波职业技术学院 | Method for modifying MC nylon by using flexible hydrogenated C9 petroleum resin |
| CN113248655A (en) * | 2021-03-26 | 2021-08-13 | 广东新华粤树脂科技有限公司 | Unsaturated phenol modified C9 petroleum resin and preparation method thereof |
| CN113956460A (en) * | 2021-09-27 | 2022-01-21 | 万华化学集团股份有限公司 | Petroleum resin-based surfactant and preparation method thereof |
| CN115216141A (en) * | 2022-08-10 | 2022-10-21 | 横店集团得邦工程塑料有限公司 | High-gloss high-glass-fiber reinforced PA6 material and preparation method thereof |
| CN115926031A (en) * | 2022-12-04 | 2023-04-07 | 新疆力铭鑫通石油化工有限公司 | Method for preparing hydrogenated petroleum resin |
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| CN112795006B (en) * | 2020-12-02 | 2022-07-08 | 宁波职业技术学院 | Method for modifying MC nylon by using flexible hydrogenated C9 petroleum resin |
| CN113248655A (en) * | 2021-03-26 | 2021-08-13 | 广东新华粤树脂科技有限公司 | Unsaturated phenol modified C9 petroleum resin and preparation method thereof |
| CN113956460A (en) * | 2021-09-27 | 2022-01-21 | 万华化学集团股份有限公司 | Petroleum resin-based surfactant and preparation method thereof |
| CN113956460B (en) * | 2021-09-27 | 2023-05-26 | 万华化学集团股份有限公司 | Petroleum resin-based surfactant and preparation method thereof |
| CN115216141A (en) * | 2022-08-10 | 2022-10-21 | 横店集团得邦工程塑料有限公司 | High-gloss high-glass-fiber reinforced PA6 material and preparation method thereof |
| CN115926031A (en) * | 2022-12-04 | 2023-04-07 | 新疆力铭鑫通石油化工有限公司 | Method for preparing hydrogenated petroleum resin |
| CN115926031B (en) * | 2022-12-04 | 2024-04-16 | 新疆力铭鑫通石油化工有限公司 | Method for preparing hydrogenated petroleum resin |
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Application publication date: 20181109 |