CN106543362B - A kind of preparation method of C5/C10 copolymer resins - Google Patents
A kind of preparation method of C5/C10 copolymer resins Download PDFInfo
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Abstract
The present invention relates to a kind of preparation method of C5/C10 copolymer resins, the C10 fraction As by Crude products.deep process C10 fraction rectifications under vacuum interception boiling point at 140~210 DEG C, the polymer raw B for then obtaining fraction A after 30~60 DEG C of C 5 fraction mixes with boiling point；In solvent be added polymer raw B, add Friedel Crafts catalyst, at 10~80 DEG C react 2.5~5h, obtain polymer fluid, then post-processed to get.The C5/C10 copolymer resins compatibility of this method preparation is good, lighter color, softening point is adjustable, this method simple process, is applicable in multiple types C5 and C10 raw material, and operability is strong, has wide popularizing application prospect.
Description
Technical field
The invention belongs to Petropols preparation field, more particularly to a kind of preparation method of C5/C10 copolymer resins.
Background technology
Petropols are with by-product C5, C9 fraction of ethylene unit etc. for primary raw material, through catalytic polymerization or free radical
It polymerize low average molecular weight polymers in obtained solid-state or viscous liquid.By resin constitute monomer and molecular structure,
Aromatic Petroleum Resins, aliphatic petroleum resin and alicyclic petroleum resin etc. can be roughly divided into.
Ethylene by-product C 5 fraction is widely used to resins synthesis, wherein pentadiene (PD), cyclopentadiene (CPD) at present
Deng for Petropols synthesize in principal monomer.Ethylene by-product C10 fractions, that is, C10 raffinates oil, and naphthalene is extracted for cracking naphthalene fraction
After obtain, wherein containing indenes (Indene), methyl indenes (Methyl-Indene), methyl styrene (Methyl-Styrene),
Naphthalene, methyl naphthalene etc. be suitable for synthesis aromatic monomer, these aromatic monomers all contain big conjugated electrons cloud structure, be easy with it is certain
Possess electrophilic group monomer to be copolymerized；In addition aromatic ring is also an ideal electrophilic substitution reaction substrate, is easily introduced on aromatic ring
All kinds of polar groups carry out chemical modification.
Patent CN94110604.7, which is provided, a kind of to be urged using the compound alchlor dication complex compound (LAL) of liquid
Agent prepares 11# colors by raw material of the C9 fractions rich in styrene, indenes, can be used for the styrene indene resin of rubber tyre industry
Method；Lv Jingfeng etc. is referred to produces 97 DEG C of softening point using petroleum cracking byproduct C9, and color number is styrene-indenes of 12#
Resin；US4113931 provides the continuous production processes that a kind of catalytic polymerization prepares indene resin；Patent US2285416 provides one
Preparation method of the kind suitable for the coumarone-indene copolymer resins of adhesive field；US4603186 provides a kind of low inherent viscosity
Acrylonitrile-methacylate methyl esters-methyl styrene/styrene-indenes quadripolymer preparation method；
JP2014237620A refers to the preparation of high-purity indenes and indene resin, but indene resin preparation process is not discussed in detail.
Invention content
Technical problem to be solved by the invention is to provide a kind of preparation method of C5/C10 copolymer resins, the method for the present invention
Polymerizing condition is mild, and gained copolymerized petroleum resin has shallow, the suitable softening point of form and aspect and excellent compatible properties.
A kind of preparation method of C5/C10 copolymer resins of the present invention, including：
(1) prepared by raw material
C10 fraction As by Crude products.deep process C10 fraction rectifications under vacuum interception boiling point at 140~210 DEG C, then by fraction A
The polymer raw B obtained after 30~60 DEG C of C 5 fraction mixes with boiling point；Wherein the mass ratio of fraction A and C5 is 1: (0.1~
10)；
(2) catalytic polymerization and post-processing
It is slowly added to polymer raw B in solvent, is slow added into Friedel-Crafts catalyst, at -10~80 DEG C
2.5~5h is reacted, rufous polymer fluid is obtained, is then post-processed to get C5/C10 copolymer resins；Wherein solvent is total object
30~60wt% of material, catalyst are 0.2~2wt% of total material.
Rectification under vacuum is the rectification under vacuum at vacuum degree -0.085~-0.096MPa in the step (1).
The component of C10 fraction As includes in the step (1)：0.5~10wt% of styrene, methyl styrene 5~
25wt%, 8~40wt% of indenes, methyl 5~50wt% of indenes, 0~2wt% of dicyclopentadiene, remaining is the saturation aromatic hydrocarbons of C8~C10
Component.
C 5 fraction component includes in the step (1)：1,3-pentadiene (pentadiene), isoprene, Isosorbide-5-Nitrae-pentadiene,
The diolefins such as cyclopentadiene and iso-amylene, diisobutylene, cyclopentene, 1- hexenes, 1- amylenes, 2- amylenes.
Solvent is saturated alkane, cycloalkane one or more of of the boiling point at 40~80 DEG C in the step (2), or
Saturation aromatic hydrocarbons mixture for boiling point at 80~200 DEG C.
Solvent is saturated alkane, cycloalkane one or more of of the boiling point at 40~80 DEG C, as pentane, isopentane,
Pentamethylene, methylpentane, n-hexane etc., or the saturation aromatic hydrocarbons mixture for boiling point at 80~200 DEG C, such as benzene, toluene, diformazan
Benzene, trimethylbenzene etc.
Freidel-Crafts catalyst is gas boron trifluoride, boron trifluoride complex, anhydrous three in the step (2)
One kind in aluminium chloride, anhydrous ferric trichloride.
It is post-processed in the step (2) and is specially：Polymer fluid is with alkali cleaning at a temperature of 30~90 DEG C of 5wt%NaOH aqueous solutions
Then Removal of catalyst is washed with clear water to neutrality, obtain milky to light yellow resin liquid, then by resin liquid warp -0.075
Under~-0.090MPa pressure, temperature is that 210~250 DEG C of rectifications under vacuum remove solvent and oligomer.
Gardner colors number≤7# of C5/C10 copolymer resins in the step (2).
The C5 raw materials of C5/C10 copolymer resins mostly come from ethylene unit by-product in the present invention, wherein pentadiene, different
The diolefins such as pentadiene, 1,4- pentadienes, cyclopentadiene, hexadiene and iso-amylene, diisobutylene, cyclopentene, 1- hexenes, 1- penta
The monoolefines such as alkene, 2- amylenes are used equally for the preparation of Petropols.The following table 1 is the typical composition of common C5 raw materials：
The typical composition of 1 common C5 raw materials of table, wt%
Single, double alkene in above-mentioned raw materials can under certain catalytic condition in C10 fractions can polycondensation monomer copolymerization obtain
Obtain Petropols.
As polymer raw, the copolymer resins of preparation after being mixed using C5 raw materials in table 1 with C10 fraction As in mass ratio 1: 1
It can be such as the following table 2：
2 different material of table prepares the performance of copolymer resins
| (1) | (2) | (3) | (4) | |
| Softening point, DEG C | 108.6 | 123.5 | 117.0 | 95.4 |
| Gardner color number, # | 5 | 6 | 7 | 3 |
| Melt viscosity, mPas | 178 | 225 | 130 | 113 |
Note：(1) raw material 1~4 and C10 fraction A mixed raw materials are corresponded to respectively to (4), catalyst is the anhydrous trichlorines of 1.0wt%
Change aluminium, 45 DEG C of reaction temperature, reaction time 3h.
C5 monoolefines, diolefin differ greatly on resin property influence when being copolymerized with C10 fractions.When in polymer raw
When monoolefine is main, the copolymer resins of acquisition have significantly low softening point and color number；Conversely, the then softening point and color number of resin
It can increase.The melt viscosity of Petropols characterizes its molecular size range and molecular structure property.Possess lower molecular weight or
There is intramolecular (3) (4) resin sample compared with polycyclic groups, melt viscosity to be substantially less than with diolefin as main C5 raw materials
(1) (2) resin sample.
Advantageous effect
(1) present invention polymerize to obtain copolymerization tree through Friedel-Crafts catalysts with C10 fractions using C5 alkene
Fat has both aliphatic hydrocarbon and fragrant hydrocarbon structure in molecular resin, has excellent gluing performance and compatibility performance；
(2) by adjusting C5 in raw material and C10 can poly group divide ratio, can effectively adjust resin softening point, color number, melting
The performances such as viscosity, make resin have a wide range of applications field；
(3) the method for the present invention simple process is applicable in multiple types C5 and C10 raw material, and operability is strong, has wide push away
Wide application prospect.
Specific implementation mode
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, people in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
The C5 raw materials of C5/C10 copolymer resins mostly come from ethylene unit by-product in the present invention, wherein pentadiene, different
The diolefins such as pentadiene, 1,4- pentadienes, cyclopentadiene, hexadiene and iso-amylene, diisobutylene, cyclopentene, 1- hexenes, 1- penta
The monoolefines such as alkene, 2- amylenes are used equally for the preparation of Petropols.Following table is the typical composition of common C5 raw materials：
The typical composition of common C5 raw materials, wt%
| Component | Raw material 1 | Raw material 2 | Raw material 3 | Raw material 4 |
| 3-methyl-1-butene | 0 | 0.88 | 0 | 4.50 |
| 1,4- pentadienes | 0 | 2.87 | 0 | 0.53 |
| 1- amylenes | 0.10 | 4.84 | 0 | 7.82 |
| 2-methyl-1-butene alkene | 0.05 | 6.13 | 0 | 21.38 |
| Isoprene | 0.10 | 19.45 | 0 | 0.79 |
| Trans- 2 amylene | 0.15 | 3.30 | 0.10 | 19.80 |
| Cis- 2- amylenes | 0.33 | 2.15 | 0.09 | 9.63 |
| 2- methyl-2-butenes | 0.40 | 2.60 | 0.32 | 18.05 |
| Trans- 1,3- pentadienes | 41.85 | 10.77 | 0.15 | 0.14 |
| Cyclopentadiene | 0.32 | 1.32 | 15.20 | 0.05 |
| Cis- 1,3- pentadienes | 20.35 | 7.63 | 0.22 | 0.63 |
| Cyclopentene | 17.80 | 5.10 | 0.70 | 1.78 |
| 1- hexenes | 0 | 0 | 0.63 | 0.90 |
| 1,5- hexadienes | 0 | 4.00 | 0 | 0 |
| Dicyclopentadiene | 0 | 0 | 60.32 | 0 |
The typical composition of ethylene by-product C10 raw materials, C10 fraction As：
The typical composition of C10 fractions, wt%
Embodiment 1-6
Different ratios of raw materials influences copolymer resins performance
Give tacit consent to C10 raw materials and boiling point is intercepted in 140~210 DEG C of components by step (1) rectifying.
Reaction condition is：It is previously added the n-hexane solvent for accounting for total material 55wt% in reaction kettle, is slowly added dropwise
The boron trifluoride ether catalyst of 0.5wt%, while being slowly added to above-mentioned mixture polymer raw.Then 2.5 are reacted at 10 DEG C
Hour, obtain rufous polymer fluid.Above-mentioned polymer fluid alkali cleaning Removal of catalyst at a temperature of 70 DEG C with 5wt%NaOH aqueous solutions,
Then it is washed to neutrality with clear water, obtains light yellow resin liquid；Under above-mentioned resin liquid warp -0.085MPa pressure, temperature is 230 DEG C
Rectification under vacuum removes solvent and oligomer to get copolymer resins.
Embodiment 7
The C5 raw materials 2 of the C10 fraction As of 70wt%, the C5 raw materials 1 of 20wt% and 10wt% are taken to be mixed to get polymer raw B.
It is previously added the toluene solvant for accounting for total material 60wt% in the autoclave with stirring, is slowly added to polymer raw B later,
The gas boron trifluoride catalyst for accounting for total quality of material 0.3wt% is added simultaneously, is reacted 3 hours at 10 DEG C, obtains rufous
Polymer fluid.Above-mentioned polymer fluid alkali cleaning Removal of catalyst at a temperature of 70 DEG C with 5wt%NaOH aqueous solutions, then with clear water wash to
Neutrality obtains light yellow resin liquid；Under above-mentioned resin liquid warp -0.085MPa pressure, temperature is that 230 DEG C of rectifications under vacuum remove solvent
And oligomer, to get being 105 DEG C to softening point, Gardner colors number are the C5/C10 copolymerized petroleum resins of 3.5#.
Embodiment 8
The C5 raw materials 4 of the C10 fraction As of 30wt%, the C5 raw materials 1 of 40wt% and 30wt% are taken to be mixed to get polymer raw B.
It is previously added the pentane solvent for accounting for total material 50wt% in the autoclave with stirring, is slowly added to polymer raw later
B, while the Catalyzed by Anhydrous Aluminium Chloride agent for accounting for total quality of material 1.0wt% is added, it reacts 2.5 hours, obtains red at 50 DEG C
Brown polymer fluid.Above-mentioned polymer fluid alkali cleaning Removal of catalyst at a temperature of 90 DEG C with 5wt%NaOH aqueous solutions, is then washed with clear water
It washs to neutrality, obtains light yellow resin liquid；Under above-mentioned resin liquid warp -0.085MPa pressure, temperature is that 240 DEG C of rectifications under vacuum remove
To get being 101 DEG C to softening point, Gardner colors number are the C5/C10 copolymerized petroleum resins of 5# for solvent and oligomer.
Embodiment 9
The C5 raw materials 4 of the C10 fraction As of 30wt%, the C5 raw materials 1 of 40wt% and 30wt% are taken to be mixed to get polymer raw B.
It is previously added the BTX aromatics solvent for accounting for total material 50wt% in the autoclave with stirring, it is former to be slowly added to polymerization later
Expect B, while the anhydrous ferric trichloride catalyst for accounting for total quality of material 1.5wt% is added, reacts 3 hours, obtain red at 25 DEG C
Brown polymer fluid.Above-mentioned polymer fluid alkali cleaning Removal of catalyst at a temperature of 90 DEG C with 5wt%NaOH aqueous solutions, is then washed with clear water
It washs to neutrality, obtains light yellow resin liquid；Under above-mentioned resin liquid warp -0.085MPa pressure, temperature is that 240 DEG C of rectifications under vacuum remove
To get being 94 DEG C to softening point, Gardner colors number are the C5/C10 copolymerized petroleum resins of 7# for solvent and oligomer.
Embodiment 10
The C5 raw materials 4 of the C10 fraction As of 50wt%, the C5 raw materials 2 of 25wt% and 25wt% are taken to be mixed to get polymer raw B.
It is previously added the xylene solvent for accounting for total material 50wt% in the autoclave with stirring, is slowly added to polymer raw later
B, while the Catalyzed by Anhydrous Aluminium Chloride agent for accounting for total quality of material 1.5wt% is added, it reacts 2.5 hours, obtains red at 30 DEG C
Brown polymer fluid.Above-mentioned polymer fluid alkali cleaning Removal of catalyst at a temperature of 75 DEG C with 5wt%NaOH aqueous solutions, is then washed with clear water
It washs to neutrality, obtains light yellow resin liquid；Under above-mentioned resin liquid warp -0.085MPa pressure, temperature is that 210 DEG C of rectifications under vacuum remove
To get being 89 DEG C to softening point, Gardner colors number are the C5/C10 copolymerized petroleum resins of 5# for solvent and oligomer.
Claims (6)
1. a kind of preparation method of C5/C10 copolymer resins, including：
(1) the C10 fraction As by Crude products.deep process C10 fraction rectifications under vacuum interception boiling point at 140~210 DEG C, then by fraction A
The polymer raw B obtained after 30~60 DEG C of C 5 fraction mixes with boiling point；Wherein the mass ratio of fraction A and C5 is 1: (0.1~
10)；
(2) in solvent be added polymer raw B, add Friedel-Crafts catalyst, at -10~80 DEG C react 2.5~
5h, obtains polymer fluid, is then post-processed to get C5/C10 copolymer resins；Wherein solvent is 30~60wt% of total material,
Catalyst is 0.2~2wt% of total material；Wherein Freidel-Crafts catalyst is gas boron trifluoride, boron trifluoride network
Close one kind in object, anhydrous ferric trichloride；Gardner colors number≤7# of C5/C10 copolymer resins in step (2).
2. a kind of preparation method of C5/C10 copolymer resins according to claim 1, it is characterised in that：The step (1)
Middle rectification under vacuum is the rectification under vacuum at vacuum degree -0.085~-0.096MPa.
3. a kind of preparation method of C5/C10 copolymer resins according to claim 1, it is characterised in that：The step (1)
The component of middle C10 fraction As includes：0.5~10wt% of styrene, 5~25wt% of methyl styrene, 8~40wt% of indenes, methyl indenes
5~50wt%, 0~2wt% of dicyclopentadiene, remaining is the saturation aromatic component of C8~C10.
4. a kind of preparation method of C5/C10 copolymer resins according to claim 1, it is characterised in that：The step (1)
Middle C 5 fraction component includes：1,3-pentadiene (pentadiene), isoprene, Isosorbide-5-Nitrae-pentadiene, cyclopentadiene, iso-amylene, two
Isobutene, cyclopentene, 1- hexenes, 1- amylenes, 2- amylenes.
5. a kind of preparation method of C5/C10 copolymer resins according to claim 1, it is characterised in that：The step (2)
Middle solvent is saturated alkane, cycloalkane one or more of of the boiling point at 40~80 DEG C, or is boiling point at 80~200 DEG C
It is saturated aromatic hydrocarbons mixture.
6. a kind of preparation method of C5/C10 copolymer resins according to claim 1, it is characterised in that：The step (2)
Middle post-processing is specially：Then polymer fluid is washed with clear water into alkali cleaning at a temperature of 30~90 DEG C of 5wt%NaOH aqueous solutions
Property, obtain milky to light yellow resin liquid, then by under resin liquid warp -0.075~-0.090MPa pressure, temperature is 210~
250 DEG C of rectifications under vacuum.
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| CN109679011B (en) * | 2017-10-18 | 2021-08-27 | 抚顺齐隆化工有限公司 | Production method of copolymerized petroleum resin |
| CN108239224B (en) * | 2018-01-10 | 2021-03-23 | 安徽同心新材料科技有限公司 | High-performance copolymer resin product for producing tire tread rubber and preparation method thereof |
| CN108219068B (en) * | 2018-01-10 | 2024-04-05 | 安徽同心新材料科技有限公司 | High-performance polymer resin with controllable melt viscosity and preparation method thereof |
| CN109337012B (en) * | 2018-08-31 | 2021-07-09 | 恒河材料科技股份有限公司 | Preparation method of phenol modified copolymerized petroleum resin |
| CN110003388B (en) * | 2019-03-26 | 2021-09-07 | 恒河材料科技股份有限公司 | Preparation method of hydrogenated modified C5 petroleum resin |
| CN111592617B (en) * | 2020-05-18 | 2021-04-02 | 恒河材料科技股份有限公司 | Preparation method of high aromatic hydrogenated resin |
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