CN106554460A - Low temperature resistant polyacrylate composition and preparation method thereof - Google Patents
Low temperature resistant polyacrylate composition and preparation method thereof Download PDFInfo
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- CN106554460A CN106554460A CN201611090388.4A CN201611090388A CN106554460A CN 106554460 A CN106554460 A CN 106554460A CN 201611090388 A CN201611090388 A CN 201611090388A CN 106554460 A CN106554460 A CN 106554460A
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- acrylate
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- acrylic acid
- temperature resistant
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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
- C08F220/16—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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions 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; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a kind of low temperature resistant polyacrylate composition and preparation method thereof, compositionss are the one kind in acrylic acid methyl ester. and ethyl acrylate, one kind in butyl acrylate and Isooctyl acrylate monomer, and the one kind in methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl butyl ester and acrylic acid tirethylene glycol methyl ether ester, the copolymer with cross-linkable monomer；Preparation method is：The various raw material monomers and regulator that constitute low temperature resistant polyacrylate composition are added in emulsifier aqueous solution, under nitrogen protection, copolymerization is caused by free radical.The low temperature resistant polyacrylate composition of the present invention, the analysis of Jing differentials scanning calorimetry, glass transition temperature are relatively low, minimum up to 40 DEG C, and oil resistivity is good；And the completely no additional heat exchange means of preparation method, reaction system temperature rise are less than 20 DEG C, polymerisation conversion up to 98 99%, mild condition possesses industrial applications condition completely.
Description
Technical field
The present invention relates to rubber synthesis technical field, more particularly to a kind of esters of acrylic acid rubber and preparation method thereof.
Background technology
Acrylate rubber (abbreviation ACM), be with acrylate as main monomer Jing copolymerization obtained by elastomer, its main chain is
Saturated carbon chains, side base are polar ester groups.As special construction gives its many excellent performance, such as heatproof, oil resistant, it is ageing-resistant,
Compression resistant, it is not cracked, does not produce thick smoke and harmful gass in flame, and resistance to ozone, uvioresistant etc..Its mechanical property and
Processing characteristics is better than fluorubber and silicone rubber, and heat-resisting, oxygen aging and oil resistivity are better than nitrile rubber, are widely used in various height
In warm, resistance to oil environment, particularly for automobile crane, valve rod, cylinder liner, hydraulic oil pipeline etc., there is the laudatory title of " automobile glue ".
Emulsion polymerization prepares the existing many parts of document reports of esters of acrylic acid rubber, but emulsion polymerization prepares esters of acrylic acid
The greatest problem that rubber is present is that polyreaction heat release is wayward, has severely impacted the industrial metaplasia of esters of acrylic acid rubber
Produce.Heat release control of the existing document also not to the polymerization of esters of acrylic acid rubber latex is illustrated.
The means of generally control heat release include the methods such as forced heat-exchanging, continuous Deca, but these methods all have polymerization
Reaction is discontinuous, and degree of polymerization fluctuation is big, and polymerisation conversion is low, and residue is too many, the problems such as quality fluctuation is big.Seek gentle
Esters of acrylic acid rubber latex polymerizing condition is the premise that esters of acrylic acid rubber industry metaplasia is produced.
And the low-temperature characteristics of acrylate rubber is determined by pendant group chain length, but longer side chain, such as butyl acrylate
Or the polymer of Isooctyl acrylate monomer, the oil resistivity of serious infringement acrylate rubber.Develop a class both low temperature resistant, and do not damage
The rubber of oil resistivity has become the problem that acrylate rubber must face.
The low-temperature characteristics of generally acrylate rubber is to measure glass transition temperature, ballistic method with differential scanning calorimetry
There is larger distortion.
By to existing document methods described research, certain methods do not put forward oil resistivity substantially, certain methods are excessively loaded down with trivial details, its
Cannot ensure in fact to obtain steady quality product, also certain methods are to add to soften in the course of processing of acrylate rubber
Agent, but this can damage the vulcanization characteristics of acrylate rubber again.
The content of the invention
In view of this, it is an object of the invention to provide a kind of low temperature resistant polyacrylate composition and preparation method thereof, with
Reduce the glass transition temperature of polyacrylate composition.
The low temperature resistant polyacrylate composition of the present invention, is the one kind in acrylic acid methyl ester. and ethyl acrylate, acrylic acid
One kind in butyl ester and Isooctyl acrylate monomer, and methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl
One kind in butyl ester and acrylic acid tirethylene glycol methyl ether ester, the copolymer with cross-linkable monomer；
The cross-linkable monomer be vinyl chloroacetate, allyl chloroacetate, ethyl maleate, monobutyl itaconate,
One or two in glycidyl methacrylate, allyl glycidyl ether and ethylidene norbornene；
The mass fraction of the acrylic acid methyl ester. or ethyl acrylate is 0-85%,
The mass fraction of the butyl acrylate or Isooctyl acrylate monomer is 5-70%,
The methoxyethyl acrylate, ethoxyethyl acrylate, two contracting second of methoxyethyl butyl ester or acrylic acid
The mass fraction of glycol methyl ether ester is 5-30%,
The mass fraction of the cross-linkable monomer is 1-10%.
Preferably, the methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl butyl ester or propylene
The mass fraction of sour tirethylene glycol methyl ether ester is 20%-30%.
The preparation method of the low temperature resistant polyacrylate composition of the present invention：
The various raw material monomers and regulator that constitute low temperature resistant polyacrylate composition are added in emulsifier aqueous solution,
Under nitrogen protection, copolymerization is caused by free radical；After the completion of copolymerization, adding reducing agent carries out post processing；
Flocculating agent breakdown of emulsion is added finally, the rinsing of Jing clear water, dehydration obtain compositionss product；
The regulator be n- dodecyl mereaptan, tert-dodecyl mercaptan and diisopropylbenzene (DIPB) xanthate in one kind, two kinds or three
Kind, consumption is the 0-0.2% of various raw material monomer gross weights；
Water in the emulsifier aqueous solution is deionized water, and consumption is the 150-500% of various raw material monomer gross weights；
The emulsifying agent is dodecyl sodium sulfate, dodecylbenzene sodium sulfonate, sodium lauryl sulphate, disproportionated rosin soap
In one or two, concentration is 2-10%；
The free radical is decomposed by free radical donor and provides, and consumption is a ten thousandth of various raw material monomer gross weights to thousand
/ bis-, the free radical donor is that two isobutyl of azo is fine, two different heptan of azo is fine, isopropyl benzene hydroperoxide, tert-butyl hydroperoxide
Hydrogen, benzoyl peroxide, cumyl peroxide, di-t-butyl peroxide, Ammonium persulfate., potassium peroxydisulfate and sodium peroxydisulfate
In one kind；
The reducing agent is sodium sulfite, sodium thiosulfate, sodium sulfite, sodium dithionite, sodium pyrosulfite, first
Aldehyde closes sodium bisulphite or the one kind in ferrous sulfate；
The flocculating agent is dilute sulfuric acid, dilute hydrochloric acid, Sodium Chloride, magnesium chloride, calcium chloride, aluminum chloride, poly-ferric chloride, poly-
The one kind or several in aluminum chloride, polyacrylamide, ethanol is closed, consumption is the 1-5% of various raw material monomer gross weights.
Beneficial effects of the present invention：
1st, low temperature resistant polyacrylate composition of the invention, the analysis of Jing differentials scanning calorimetry, glass transition temperature are equal
It is relatively low, minimum reachable -40 DEG C, and oil resistivity is good.
2nd, the preparation method of low temperature resistant polyacrylate composition of the invention, its completely no additional heat exchange means, reaction
System temperature rise is less than 20 DEG C, and polymerisation conversion is up to 98-99%, and mild condition possesses industrial applications condition completely.
Specific embodiment
With reference to embodiment, the invention will be further described.
Embodiment one：The preparation method of the low temperature resistant polyacrylate composition of the present embodiment：
1) formula meter includes：
2) isopropyl benzene hydroperoxide, sodium sulfite, dilute hydrochloric acid and polyacrylamide deionized water are diluted to 1% molten
Liquid is standby；
3) methoxyethyl acrylate, Isooctyl acrylate monomer, ethyl maleate, diisopropylbenzene (DIPB) xanthate and go from
Sub- water, disproportionated rosin soap, dodecyl sodium sulfate input stirring container, stir 1 hour, are passed through nitrogen.Container is heated to 40 DEG C,
Stop heating, input isopropyl benzene hydroperoxide, half amount sodium sulfite, emulsion system start temperature rise, and polyreaction starts, polymerization
About 1 hour time, 59 DEG C of temperature rise peak.Half amount sodium sulfite of input, continues stirring 1 hour.Treat that container is cooled to often
Wen Hou, adds dilute hydrochloric acid and polyacrylamide, separates out white rubber granule, and Jing rinsing dehydrations obtain finished product, and yield is
98.5%, -40 DEG C of glass transition temperature, rubber are tested with No. 1 standard oil volume change 6%.
Embodiment two：The preparation method of the low temperature resistant polyacrylate composition of the present embodiment：
1) formula meter includes：
2) two isobutyl of azo fine, ferrous sulfate, calcium chloride deionized water are diluted to 1% solution for standby；
3) ethyl acrylate, butyl acrylate, acrylic acid tirethylene glycol methyl ether ester, allyl chloroacetate, positive 12
Mercaptan and deionized water, sodium lauryl sulphate input stirring container, stir 1 hour, are passed through nitrogen.Container is heated to 20 DEG C,
Stop heating, input two isobutyl of azo is fine, half amount ferrous sulfate, emulsion system starts temperature rise, and polyreaction starts, polymerization time
About 1 hour, 38.8 DEG C of temperature rise peak.Half amount ferrous sulfate of input, continues stirring 1 hour.After container is cooled to room temperature,
Calcium chloride is added, white rubber granule is separated out, Jing rinsing dehydrations obtain finished product, and yield is 99%, glass transition temperature-
30.1 DEG C, rubber is tested with No. 1 standard oil volume change 4%.
Embodiment three：The preparation method of the low temperature resistant polyacrylate composition of the present embodiment：
2) formula meter includes：
2) Ammonium persulfate., sodium sulfite, polyacrylamide, Sodium Chloride deionized water are diluted to 1% solution for standby；
3) ethyl acrylate, butyl acrylate, methoxyethyl butyl ester, allyl glycidyl ether and deionization
Water, sodium lauryl sulphate input stirring container, stir 1 hour, are passed through nitrogen.Container is heated to 30 DEG C, stops heating, input
Ammonium persulfate., half amount sodium sulfite, emulsion system start temperature rise, and polyreaction starts, polymerization time about 1 hour, and temperature rise is most
49.1 DEG C of high point.Half amount sodium sulfite of input, continues stirring 1 hour.After container is cooled to room temperature, add Sodium Chloride, poly- third
Acrylamide, separates out white rubber granule, and Jing rinsing dehydrations obtain finished product, and yield is 98.8%, glass transition temperature -24.3
DEG C, rubber is tested with No. 1 standard oil volume change 4%.
In a word in being embodied as, the mass fraction of the acrylic acid methyl ester. or ethyl acrylate can be 0-85% scopes
In arbitrary value, the mass fraction of the butyl acrylate or Isooctyl acrylate monomer can be the arbitrary value in 5-70% scopes,
The methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl butyl ester or acrylic acid tirethylene glycol methyl ether
The mass fraction of ester can be the arbitrary value in 5-30% scopes, and the mass fraction of the cross-linkable monomer can be 1-10% models
Arbitrary value in enclosing.
And the regulator in the preparation method of low temperature resistant polyacrylate composition can be n- dodecyl mereaptan, 12 sulfur of uncle
One kind in alcohol and diisopropylbenzene (DIPB) xanthate, two or three, consumption can be the 0- of various raw material monomer gross weights
0.2%；Water in the emulsifier aqueous solution is deionized water, and consumption can be the 150- of various raw material monomer gross weights
500%；The emulsifying agent can be dodecyl sodium sulfate, dodecylbenzene sodium sulfonate, sodium lauryl sulphate, disproportionated rosin
Any one in soap or two kinds, concentration can be 2-10%；The free radical decomposes offer by free radical donor, and consumption is each
The a ten thousandth of raw material monomer gross weight is planted to 2/1000ths, the free radical donor can, azo two fine for two isobutyl of azo
Different heptan is fine, isopropyl benzene hydroperoxide, tert-butyl hydroperoxide, benzoyl peroxide, cumyl peroxide, two tertiary fourth of peroxidating
Any one in base, Ammonium persulfate., potassium peroxydisulfate and sodium peroxydisulfate；And the polyreaction of free radical donor is used alone
Temperature is 50-100 DEG C, and the polymeric reaction temperature being used in conjunction with reducing agent is 5-50 DEG C；The reducing agent can be sulfurous acid
Sodium, sodium thiosulfate, sodium sulfite, sodium dithionite, sodium pyrosulfite, sodium formaldehyde sulphoxylate or ferrous sulfate
In any one；The flocculating agent is dilute sulfuric acid, dilute hydrochloric acid, Sodium Chloride, magnesium chloride, calcium chloride, aluminum chloride, polyaluminium
In ferrum, aluminium polychlorid, polyacrylamide, ethanol any one or it is several, consumption is various raw material monomer gross weights
1-5%.
The low temperature resistant polyacrylate composition of various embodiments above, the analysis of Jing differentials scanning calorimetry, glass transition temperature
Degree is relatively low, minimum reachable -40 DEG C, and oil resistivity is good；And the preparation method of low temperature resistant polyacrylate composition of the invention
Completely no additional heat exchange means, reaction system temperature rise are less than 20 DEG C, and polymerisation conversion is up to 98-99%, and mild condition is complete
Possesses full industrial applications condition.
Finally illustrate, above example is only unrestricted to illustrate technical scheme, although with reference to compared with
Good embodiment has been described in detail to the present invention, it will be understood by those within the art that, can be to the skill of the present invention
Art scheme is modified or equivalent, and without deviating from the objective and scope of technical solution of the present invention, which all should be covered at this
In the middle of the right of invention.
Claims (3)
1. a kind of low temperature resistant polyacrylate composition, it is characterised in that：For the one kind in acrylic acid methyl ester. and ethyl acrylate,
One kind in butyl acrylate and Isooctyl acrylate monomer, and methoxyethyl acrylate, ethoxyethyl acrylate, acrylic acid
One kind in methoxybutyl and acrylic acid tirethylene glycol methyl ether ester, the copolymer with cross-linkable monomer；
The cross-linkable monomer is vinyl chloroacetate, allyl chloroacetate, ethyl maleate, monobutyl itaconate, methyl
One or two in glycidyl acrylate, allyl glycidyl ether and ethylidene norbornene；
The mass fraction of the acrylic acid methyl ester. or ethyl acrylate is 0-85%,
The mass fraction of the butyl acrylate or Isooctyl acrylate monomer is 5-70%,
The methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl butyl ester or acrylic acid tirethylene glycol
The mass fraction of methyl ether ester is 5-30%,
The mass fraction of the cross-linkable monomer is 1-10%.
2. according to the low temperature resistant polyacrylate composition described in claim 1, it is characterised in that：The methoxyethyl
The mass fraction of ethyl ester, ethoxyethyl acrylate, methoxyethyl butyl ester or acrylic acid tirethylene glycol methyl ether ester is
20%-30%.
3. the preparation method of low temperature resistant polyacrylate composition described in a kind of claim 1, it is characterised in that：
The various raw material monomers and regulator that constitute low temperature resistant polyacrylate composition are added in emulsifier aqueous solution, in nitrogen
Under gas shielded, copolymerization is caused by free radical；After the completion of copolymerization, adding reducing agent carries out post processing；Finally
Flocculating agent breakdown of emulsion is added, the rinsing of Jing clear water, dehydration obtain compositionss product；
The regulator be n- dodecyl mereaptan, tert-dodecyl mercaptan and diisopropylbenzene (DIPB) xanthate in one kind, two or three, use
Measure the 0-0.2% for various raw material monomer gross weights；
Water in the emulsifier aqueous solution is deionized water, and consumption is the 150-500% of various raw material monomer gross weights；
The emulsifying agent be dodecyl sodium sulfate, dodecylbenzene sodium sulfonate, sodium lauryl sulphate, in disproportionated rosin soap
One or two, concentration is 2-10%；
The free radical is decomposed by free radical donor and provides, consumption be various raw material monomer gross weights a ten thousandth to thousand/
Two, the free radical donor is that two isobutyl of azo is fine, two different heptan of azo is fine, isopropyl benzene hydroperoxide, tert-butyl hydroperoxide, mistake
In BP, cumyl peroxide, di-t-butyl peroxide, Ammonium persulfate., potassium peroxydisulfate and sodium peroxydisulfate one
Kind；
The reducing agent is sodium sulfite, sodium thiosulfate, sodium sulfite, sodium dithionite, sodium pyrosulfite, formaldehyde conjunction
One kind in sodium bisulphite or ferrous sulfate；
The flocculating agent is dilute sulfuric acid, dilute hydrochloric acid, Sodium Chloride, magnesium chloride, calcium chloride, aluminum chloride, poly-ferric chloride, polymerization chlorine
Change the one kind or several in aluminum, polyacrylamide, ethanol, consumption is the 1-5% of various raw material monomer gross weights.
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| CN201611090388.4A CN106554460A (en) | 2016-12-01 | 2016-12-01 | Low temperature resistant polyacrylate composition and preparation method thereof |
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| CN201611090388.4A CN106554460A (en) | 2016-12-01 | 2016-12-01 | Low temperature resistant polyacrylate composition and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108164641A (en) * | 2018-02-01 | 2018-06-15 | 重庆金茂达特种橡胶有限公司 | Polyacrylate composition |
| CN108276519A (en) * | 2018-02-01 | 2018-07-13 | 重庆金茂达特种橡胶有限公司 | Acrylic ester polymerization reaction retarder and its acrylate composition |
| CN110498880A (en) * | 2019-07-16 | 2019-11-26 | 九江杜威橡胶科技有限公司 | A kind of manufacturing method of extremely cold-resistant carboxyl type acrylic rubber |
| CN110527013A (en) * | 2019-07-16 | 2019-12-03 | 九江杜威橡胶科技有限公司 | A kind of preparation method of the double cross-linked acrylate rubbers of hardy type |
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| CN1552748A (en) * | 2003-05-30 | 2004-12-08 | 北京化工大学 | Method for decreasing acrylic ester rubber glass-transition temperature |
| CN101787098A (en) * | 2010-02-26 | 2010-07-28 | 华南理工大学 | Preparation method and application of acrylate heterozygotic emulsion |
| CN102167772A (en) * | 2011-01-20 | 2011-08-31 | 安徽大学 | Fluorine-containing easily processed acrylate rubber and preparation method thereof |
| CN102643383A (en) * | 2012-04-01 | 2012-08-22 | 安徽大学 | Preparation method of raw oil-extended alkyl acrylate copolymer (ACM) |
| CN103396508A (en) * | 2013-07-29 | 2013-11-20 | 华南理工大学 | Low-temperature self-crosslinked water-based acrylate resin, and preparation method and application thereof |
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2016
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1552748A (en) * | 2003-05-30 | 2004-12-08 | 北京化工大学 | Method for decreasing acrylic ester rubber glass-transition temperature |
| CN101787098A (en) * | 2010-02-26 | 2010-07-28 | 华南理工大学 | Preparation method and application of acrylate heterozygotic emulsion |
| CN102167772A (en) * | 2011-01-20 | 2011-08-31 | 安徽大学 | Fluorine-containing easily processed acrylate rubber and preparation method thereof |
| CN102643383A (en) * | 2012-04-01 | 2012-08-22 | 安徽大学 | Preparation method of raw oil-extended alkyl acrylate copolymer (ACM) |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108164641A (en) * | 2018-02-01 | 2018-06-15 | 重庆金茂达特种橡胶有限公司 | Polyacrylate composition |
| CN108276519A (en) * | 2018-02-01 | 2018-07-13 | 重庆金茂达特种橡胶有限公司 | Acrylic ester polymerization reaction retarder and its acrylate composition |
| CN110498880A (en) * | 2019-07-16 | 2019-11-26 | 九江杜威橡胶科技有限公司 | A kind of manufacturing method of extremely cold-resistant carboxyl type acrylic rubber |
| CN110527013A (en) * | 2019-07-16 | 2019-12-03 | 九江杜威橡胶科技有限公司 | A kind of preparation method of the double cross-linked acrylate rubbers of hardy type |
| CN110498880B (en) * | 2019-07-16 | 2022-04-19 | 九江杜威橡胶科技有限公司 | Preparation method of extremely cold-resistant carboxyl acrylate rubber |
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Application publication date: 20170405 |
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| RJ01 | Rejection of invention patent application after publication |