CN106496402A - A kind of high oil-absorbing resin and preparation method thereof - Google Patents

A kind of high oil-absorbing resin and preparation method thereof Download PDF

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Publication number
CN106496402A
CN106496402A CN201611074569.8A CN201611074569A CN106496402A CN 106496402 A CN106496402 A CN 106496402A CN 201611074569 A CN201611074569 A CN 201611074569A CN 106496402 A CN106496402 A CN 106496402A
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parts
oil
absorbing resin
resin
reaction system
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郝静
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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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/32—Materials not provided for elsewhere for absorbing liquids to remove pollution, e.g. oil, gasoline, fat
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
    • C08J2333/12—Homopolymers or copolymers of methyl methacrylate

Abstract

The present invention relates to a kind of high oil-absorbing resin and preparation method thereof, belongs to oil-absorbing resin technical field.The present invention adopts process for suspension polymerization, with methyl methacrylate, octadecyl acrylate, dodecyl acrylate as primary raw material, with dimethacrylate diethylene glycol ester as cross-linking agent, the mechanical property of oil-absorbing resin is improved by adding acrylonitrile, and increase the porous of resin with toluene as porogen, it is initiator in initiator dibenzoyl peroxide, is prepared for a kind of high oil-absorbing resin.The oil-absorbing resin to the adsorbance of 120# gasoline up to 20 25g/g, with preferable application prospect.

Description

A kind of high oil-absorbing resin and preparation method thereof
Technical field
The present invention relates to a kind of resin and preparation method thereof, it is more particularly related to a kind of high oil-absorbing resin and Its preparation method, belongs to oil-absorbing resin technical field.
Background technology
As offshore oil exploitation is increasingly frequent with transport, marine oil spill accident happens occasionally.Oils enters ocean, right Natural environment, aquaculture, shallow water seashore, harbour industry etc. can all cause harm difficult to the appraisal, therefore, develop dynamical Oil suction product has important practical usage.High oil-absorbing resin is low crosslinking degree polymer obtained in oleophylic monomer, with three-dimensional Cross-linked structure, inside have certain micropore, this material can effective process marine oil overflow and oily waste water, reduce to ring The harm in border.
Initiation polymerization is carried out with oleosoluble radical initiators as initiator, synthetic method has mainly adopted suspension polymerisation and breast Liquid is polymerized.Conventional acrylic oil-absorbing resin has that mechanical property is not good enough, easily broken, oil absorption is not high lacks in use Fall into, limit its further application.In recent years, with constantly improve and the development of polymerization technique, and to acrylic resin The continuous improvement that combination property is required, in addition attention of the people to environment-friendly products using environmentally-friendly technique and pass through macromolecule MOLECULE DESIGN prepares the acrylic resin that combination property is preferable, oil absorption is high and gets more and more people's extensive concerning.
Existing oil-absorbing resin oil absorption is relatively low.
Content of the invention
Present invention seek to address that the relatively low problem of oil-absorbing resin oil absorption in prior art, there is provided a kind of high oil-absorbing resin, The oil-absorbing resin has the advantages that oil absorption is higher.
In order to realize foregoing invention purpose, its specific technical scheme is as follows：
A kind of high oil-absorbing resin, it is characterised in that：Including following raw materials by weight：
Oil phase：
Methyl methacrylate 30-40 parts
Butyl methacrylate 10-15 parts
Acrylonitrile 5-10 parts
Octadecyl acrylate 30-35 parts
Dodecyl acrylate 25-30 parts
Dimethacrylate diethylene glycol ester 1-2 parts
Toluene 50-60 parts
Azodiisobutyronitrile (AIBN) 1-3 parts；
Water phase：
10% polyvinyl alcohol（PVA1788）Aqueous 5-10 part
Gelatin 5-10 parts
NaCl 10-20 parts
CaSO43-5 parts
0.1% methylene blue aqueous 5-10 part
Deionized water 600-800 parts.
A kind of preparation method of high oil-absorbing resin, it is characterised in that：Comprise the following steps that：
A, accurately weigh according to recipe requirements methyl methacrylate, butyl methacrylate, acrylonitrile, octadecyl acrylate, Dodecyl acrylate, dimethacrylate diethylene glycol ester, toluene and azodiisobutyronitrile are sufficiently mixed in container uniformly, standby With；
B, according to water phase recipe requirements, each component is added in the 1000ml there-necked flasks of a tool stirring, condensing tube and charge door；
C, system temperature is risen to 40-50 DEG C, stirring is started until each component is sufficiently mixed dissolving；The oil phase for preparing is mixed Thing is poured in the water phase there-necked flask for preparing；It is 150-200 rev/min to keep the speed stirred in reactor, is formed oil phase Uniform bead is dispersed in the water phase for preparing in advance；75-80 DEG C is warming up to, and the reaction temperature is kept until scattered oil droplet Sizing is not broken；
D, polymerization reaction system temperature is raised to 80-85 DEG C, is incubated 2-3 hour；Polymerization reaction system is warming up to 85-90 DEG C, it is incubated 2-3 hour；Polymerization reaction system is warming up to 95 DEG C, 2-3 hour is incubated；Reaction system is cooled to room temperature, Leach resin bead；
E, drip washing being carried out using ethanol to resin, removing the porogen in resin, vacuum drying obtains high oil-absorbing resin.
The Advantageous Effects that the present invention brings：
The present invention adopts process for suspension polymerization, with methyl methacrylate, octadecyl acrylate, dodecyl acrylate as main former Material, with dimethacrylate diethylene glycol ester as cross-linking agent, improves the mechanical property of oil-absorbing resin by adding acrylonitrile, and with Toluene is the porous that porogen increases resin, is initiator in initiator dibenzoyl peroxide, is prepared for a kind of high oil absorption Resin.The oil-absorbing resin to the adsorbance of 120# gasoline up to 20-25g/g, with preferable application prospect.
Specific embodiment
Embodiment 1
A kind of high oil-absorbing resin, including following raw materials by weight：
Oil phase：
30 parts of methyl methacrylate
10 parts of butyl methacrylate
5 parts of acrylonitrile
30 parts of octadecyl acrylate
25 parts of dodecyl acrylate
1 part of dimethacrylate diethylene glycol ester
50 parts of toluene
1 part of azodiisobutyronitrile (AIBN)；
Water phase：
10% polyvinyl alcohol（PVA1788）5 parts of aqueous
5 parts of gelatin
10 parts of NaCl
CaSO43 parts
0.1% 5 parts of methylene blue aqueous
600 parts of deionized water.
Embodiment 2
A kind of high oil-absorbing resin, including following raw materials by weight：
Oil phase：
40 parts of methyl methacrylate
15 parts of butyl methacrylate
10 parts of acrylonitrile
35 parts of octadecyl acrylate
30 parts of dodecyl acrylate
2 parts of dimethacrylate diethylene glycol ester
60 parts of toluene
3 parts of azodiisobutyronitrile (AIBN)；
Water phase：
10% polyvinyl alcohol（PVA1788）10 parts of aqueous
10 parts of gelatin
20 parts of NaCl
CaSO45 parts
0.1% 10 parts of methylene blue aqueous
800 parts of deionized water.
Embodiment 3
A kind of high oil-absorbing resin, including following raw materials by weight：
Oil phase：
35 parts of methyl methacrylate
12 parts of butyl methacrylate
7 parts of acrylonitrile
33 parts of octadecyl acrylate
28 parts of dodecyl acrylate
1.5 parts of dimethacrylate diethylene glycol ester
55 parts of toluene
2 parts of azodiisobutyronitrile (AIBN)；
Water phase：
10% polyvinyl alcohol（PVA1788）8 parts of aqueous
7 parts of gelatin
15 parts of NaCl
CaSO44 parts
0.1% 7 parts of methylene blue aqueous
700 parts of deionized water.
Embodiment 4
A kind of preparation method of high oil-absorbing resin, comprises the following steps that：
A, accurately weigh according to recipe requirements methyl methacrylate, butyl methacrylate, acrylonitrile, octadecyl acrylate, Dodecyl acrylate, dimethacrylate diethylene glycol ester, toluene and azodiisobutyronitrile are sufficiently mixed in container uniformly, standby With；
B, according to water phase recipe requirements, each component is added in the 1000ml there-necked flasks of a tool stirring, condensing tube and charge door；
C, system temperature is risen to 40 DEG C, stirring is started until each component is sufficiently mixed dissolving；By the oil mixture for preparing Pour in the water phase there-necked flask for preparing；It is 150 revs/min to keep the speed stirred in reactor, oil phase is formed uniformly Bead is dispersed in the water phase for preparing in advance；75 DEG C are warming up to, and the reaction temperature are kept until scattered oil droplet does not break sizing；
D, polymerization reaction system temperature is raised to 80 DEG C, is incubated 2 hours；Polymerization reaction system is warming up to 85 DEG C, 2 are incubated Hour；Polymerization reaction system is warming up to 95 DEG C, 2 hours are incubated；Reaction system is cooled to room temperature, resin bead is leached；
E, drip washing being carried out using ethanol to resin, removing the porogen in resin, vacuum drying obtains high oil-absorbing resin.
Embodiment 5
A kind of preparation method of high oil-absorbing resin, comprises the following steps that：
A, accurately weigh according to recipe requirements methyl methacrylate, butyl methacrylate, acrylonitrile, octadecyl acrylate, Dodecyl acrylate, dimethacrylate diethylene glycol ester, toluene and azodiisobutyronitrile are sufficiently mixed in container uniformly, standby With；
B, according to water phase recipe requirements, each component is added in the 1000ml there-necked flasks of a tool stirring, condensing tube and charge door；
C, system temperature is risen to 50 DEG C, stirring is started until each component is sufficiently mixed dissolving；By the oil mixture for preparing Pour in the water phase there-necked flask for preparing；It is 200 revs/min to keep the speed stirred in reactor, oil phase is formed uniformly Bead is dispersed in the water phase for preparing in advance；80 DEG C are warming up to, and the reaction temperature are kept until scattered oil droplet does not break sizing；
D, polymerization reaction system temperature is raised to 85 DEG C, is incubated 3 hours；Polymerization reaction system is warming up to 90 DEG C, 3 are incubated Hour；Polymerization reaction system is warming up to 95 DEG C, 3 hours are incubated；Reaction system is cooled to room temperature, resin bead is leached；
E, drip washing being carried out using ethanol to resin, removing the porogen in resin, vacuum drying obtains high oil-absorbing resin.
Embodiment 6
A kind of preparation method of high oil-absorbing resin, comprises the following steps that：
A, accurately weigh according to recipe requirements methyl methacrylate, butyl methacrylate, acrylonitrile, octadecyl acrylate, Dodecyl acrylate, dimethacrylate diethylene glycol ester, toluene and azodiisobutyronitrile are sufficiently mixed in container uniformly, standby With；
B, according to water phase recipe requirements, each component is added in the 1000ml there-necked flasks of a tool stirring, condensing tube and charge door；
C, system temperature is risen to 45 DEG C, stirring is started until each component is sufficiently mixed dissolving；By the oil mixture for preparing Pour in the water phase there-necked flask for preparing；It is 170 revs/min to keep the speed stirred in reactor, oil phase is formed uniformly Bead is dispersed in the water phase for preparing in advance；77 DEG C are warming up to, and the reaction temperature are kept until scattered oil droplet does not break sizing；
D, polymerization reaction system temperature is raised to 82 DEG C, is incubated 2.5 hours；Polymerization reaction system is warming up to 88 DEG C, is incubated 2.5 hours；Polymerization reaction system is warming up to 95 DEG C, 2.5 hours are incubated；Reaction system is cooled to room temperature, tree is leached Fat bead；
E, drip washing being carried out using ethanol to resin, removing the porogen in resin, vacuum drying obtains high oil-absorbing resin.

Claims (2)

1. a kind of high oil-absorbing resin, it is characterised in that：Including following raw materials by weight：
Oil phase：
Methyl methacrylate 30-40 parts
Butyl methacrylate 10-15 parts
Acrylonitrile 5-10 parts
Octadecyl acrylate 30-35 parts
Dodecyl acrylate 25-30 parts
Dimethacrylate diethylene glycol ester 1-2 parts
Toluene 50-60 parts
Azodiisobutyronitrile (AIBN) 1-3 parts；
Water phase：
10% polyvinyl alcohol（PVA1788）Aqueous 5-10 part
Gelatin 5-10 parts
NaCl 10-20 parts
CaSO43-5 parts
0.1% methylene blue aqueous 5-10 part
Deionized water 600-800 parts.
2. the preparation method of a kind of high oil-absorbing resin according to claim 1, it is characterised in that：Walk including following technique Suddenly：
A, accurately weigh according to recipe requirements methyl methacrylate, butyl methacrylate, acrylonitrile, octadecyl acrylate, Dodecyl acrylate, dimethacrylate diethylene glycol ester, toluene and azodiisobutyronitrile are sufficiently mixed in container uniformly, standby With；
B, according to water phase recipe requirements, each component is added in the 1000ml there-necked flasks of a tool stirring, condensing tube and charge door；
C, system temperature is risen to 40-50 DEG C, stirring is started until each component is sufficiently mixed dissolving；The oil phase for preparing is mixed Thing is poured in the water phase there-necked flask for preparing；It is 150-200 rev/min to keep the speed stirred in reactor, is formed oil phase Uniform bead is dispersed in the water phase for preparing in advance；75-80 DEG C is warming up to, and the reaction temperature is kept until scattered oil droplet Sizing is not broken；
D, polymerization reaction system temperature is raised to 80-85 DEG C, is incubated 2-3 hour；Polymerization reaction system is warming up to 85-90 DEG C, it is incubated 2-3 hour；Polymerization reaction system is warming up to 95 DEG C, 2-3 hour is incubated；Reaction system is cooled to room temperature, Leach resin bead；
E, drip washing being carried out using ethanol to resin, removing the porogen in resin, vacuum drying obtains high oil-absorbing resin.
CN201611074569.8A 2016-11-30 2016-11-30 A kind of high oil-absorbing resin and preparation method thereof Pending CN106496402A (en)

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Application Number Priority Date Filing Date Title
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Publication Number Publication Date
CN106496402A true CN106496402A (en) 2017-03-15

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107099003A (en) * 2017-05-25 2017-08-29 北京宝辰联合科技股份有限公司 A kind of polyacrylate high oil-absorbing resin and preparation method thereof
CN110052253A (en) * 2019-04-12 2019-07-26 华北水利水电大学 A kind of reinforcing filler in high oil-absorbing resin

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1948357A (en) * 2006-10-27 2007-04-18 东华大学 High oil absorption resin and its preparation method
CN103145927A (en) * 2013-03-13 2013-06-12 河南科技大学 High oil-absorbing resin and preparation method for same
CN104672372A (en) * 2013-11-28 2015-06-03 天津市耀新科技发展有限公司 High-oil-absorptivity resin and preparation method thereof
CN104693380A (en) * 2014-07-03 2015-06-10 中国科学院西北高原生物研究所 High oil absorption resin and preparation method thereof
CN104744626A (en) * 2013-12-31 2015-07-01 天津帅耀生产力促进有限公司 Oil-absorbing resin and preparation method thereof
CN105254818A (en) * 2015-10-23 2016-01-20 蓝星（成都）新材料有限公司 High-oil-absorption resin and preparation method thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1948357A (en) * 2006-10-27 2007-04-18 东华大学 High oil absorption resin and its preparation method
CN103145927A (en) * 2013-03-13 2013-06-12 河南科技大学 High oil-absorbing resin and preparation method for same
CN104672372A (en) * 2013-11-28 2015-06-03 天津市耀新科技发展有限公司 High-oil-absorptivity resin and preparation method thereof
CN104744626A (en) * 2013-12-31 2015-07-01 天津帅耀生产力促进有限公司 Oil-absorbing resin and preparation method thereof
CN104693380A (en) * 2014-07-03 2015-06-10 中国科学院西北高原生物研究所 High oil absorption resin and preparation method thereof
CN105254818A (en) * 2015-10-23 2016-01-20 蓝星（成都）新材料有限公司 High-oil-absorption resin and preparation method thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107099003A (en) * 2017-05-25 2017-08-29 北京宝辰联合科技股份有限公司 A kind of polyacrylate high oil-absorbing resin and preparation method thereof
CN107099003B (en) * 2017-05-25 2019-07-30 北京宝辰联合科技股份有限公司 A kind of polyacrylate high oil-absorbing resin and preparation method thereof
CN110052253A (en) * 2019-04-12 2019-07-26 华北水利水电大学 A kind of reinforcing filler in high oil-absorbing resin

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Application publication date: 20170315