CN106496405A - Polyacrylate composition and preparation method thereof - Google Patents
Polyacrylate composition and preparation method thereof Download PDFInfo
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- CN106496405A CN106496405A CN201611091589.6A CN201611091589A CN106496405A CN 106496405 A CN106496405 A CN 106496405A CN 201611091589 A CN201611091589 A CN 201611091589A CN 106496405 A CN106496405 A CN 106496405A
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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
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/14—Treatment of polymer emulsions
- C08F6/22—Coagulation
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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
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a kind of polyacrylate composition and preparation method thereof, copolymer of the polyacrylate composition for the acrylic ester monomer that mass fraction is 90 99% and the cross-linkable monomer that mass fraction is 1 10%；Preparation method is：Acrylic ester monomer raw material, cross-linkable monomer raw material and regulator are added in emulsifier aqueous solution, under nitrogen protection, copolymerization is caused by free radical；And after the completion of copolymerization, add reducing agent to carry out post processing；Flocculating agent breakdown of emulsion is eventually adding, is rinsed through clear water, dehydration obtains polyacrylate composition.Polyacrylate composition of the present invention and preparation method thereof, preparation process are carried out in the case of completely without additional heat exchange means, and reaction system temperature rise is less than 20 DEG C, polymerisation conversion up to 98 99%, and 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), it is main monomer through elastomer obtained by copolymerization with acrylate to be, 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, 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 nitrile rubber better than fluorubber and silicone rubber, heat-resisting, oxygen aging and oil resistivity, is widely used in various height
In warm, resistance to oil environment, particularly it is used for automobile crane, valve rod, cylinder liner, hydraulic oil pipeline etc., has 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.The heat release control that existing document is not also polymerized to 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.
Content of the invention
In view of this, it is an object of the invention to provide a kind of polyacrylate composition and preparation method thereof, to solve third
The heat release control problem of olefin(e) acid ester rubber emulsion polymerization.
Polyacrylate composition of the present invention, is the copolymer of acrylic ester monomer and cross-linkable monomer, the copolymerization
In thing, the mass fraction of acrylic ester monomer is 90-99%, and the mass fraction of cross-linkable monomer is 1-10%, the acrylic acid
Esters monomer is acrylic acid methyl ester., ethyl acrylate, butyl acrylate, Isooctyl acrylate monomer, methoxyethyl acrylate, propylene
One kind or several in sour ethoxy ethyl ester, methoxyethyl butyl ester and acrylic acid tirethylene glycol methyl ether ester, described
Cross-linkable monomer is vinyl chloroacetate, allyl chloroacetate, ethyl maleate, monobutyl itaconate, methacrylic acid contracting
One or two in water glyceride, allyl glycidyl ether, ethylidene norbornene.
The preparation method of polyacrylate composition of the present invention：By acrylic ester monomer raw material, cross-linkable monomer raw material,
And regulator is added in emulsifier aqueous solution, under nitrogen protection, causes copolymerization by free radical；And it is anti-in combined polymerization
Should after the completion of, add reducing agent carry out post processing, the consumption of reducing agent is consistent with free radical donor, reducing agent be sodium sulfite,
In sodium thiosulfate, sodium sulfite, sodium dithionite, sodium pyrosulfite, sodium formaldehyde sulphoxylate, ferrous sulfate one
Kind；Flocculating agent breakdown of emulsion is eventually adding, is rinsed through clear water, dehydration obtains polyacrylate composition；
The regulator be n- dodecyl mereaptan, tert-dodecyl mercaptan and diisopropylbenzene (DIPB) xanthate in one kind, two kinds or three
Kind, the consumption of the regulator is the 0-0.2% of acrylic ester monomer raw material and cross-linkable monomer raw material gross mass；
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, free radical donor is that two isobutyl of azo is fine, two different heptan of azo is fine,
Isopropyl benzene hydroperoxide, tert-butyl hydroperoxide, benzoyl peroxide, cumyl peroxide, di-t-butyl peroxide, over cure
One kind in sour ammonium, potassium peroxydisulfate and sodium peroxydisulfate；The consumption of the free radical donor be acrylic ester monomer raw material and
The a ten thousandth of cross-linkable monomer raw material gross mass is to 2/1000ths；
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 and ethanol is closed, it is acrylic ester monomer that the flocculating agent is consumption
Raw material and the 1-5% of cross-linkable monomer raw material gross mass.
Beneficial effects of the present invention：
Polyacrylate composition of the present invention and preparation method thereof, preparation process are completely without additional heat exchange means
In the case of carry out, reaction system temperature rise be less than 20 DEG C, polymerisation conversion is up to 98-99%, and mild condition possesses industry completely
Change application conditions.
Specific embodiment
With reference to embodiment, the invention will be further described.
Embodiment one：The preparation method of the present embodiment polyacrylate composition：
1) formula meter includes：
2) potassium peroxydisulfate, sodium formaldehyde sulphoxylate and aluminium polychlorid deionized water are diluted to 1% solution for standby；
3) ethyl acrylate, allyl chloroacetate, tert-dodecyl mercaptan and deionized water and dodecylbenzene sodium sulfonate
Input stirring container, stirs 1 hour, is passed through nitrogen.Container is heated to 60 DEG C, stops heating, puts into potassium peroxydisulfate, emulsion system
Start temperature rise, polyreaction starts, polymerization time about 1 hour, 79.2 DEG C of temperature rise peak.Input formaldehyde closes bisulphite
Sodium, continues stirring 1 hour.After container is cooled to room temperature, aluminium polychlorid is added, separate out white rubber granule, de- through rinsing
Water obtains finished product, and yield is 98.9%.
Embodiment two：The preparation method of the present embodiment polyacrylate composition：
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, ethyl maleate, diisopropylbenzene (DIPB) xanthate and deionized water, disproportionated rosin
Soap, dodecyl sodium sulfate input stirring container, stir 1 hour, are passed through nitrogen.Container is heated to 40 DEG C, stops heating, input
Isopropyl benzene hydroperoxide, half amount sodium sulfite, emulsion system start temperature rise, and polyreaction starts, and polymerization time about 1 is little
When, 59 DEG C of temperature rise peak.Input half measures sodium sulfite, continues stirring 1 hour.After container is cooled to room temperature, add dilute
Hydrochloric acid and polyacrylamide, separate out white rubber granule, obtain finished product through rinsing dehydration, and yield is 98.5%.
Embodiment three：The preparation method of the present embodiment polyacrylate composition：
1) formula meter includes：
2) fine for two isobutyl of azo, ferrous sulfate, calcium chloride deionized water are diluted to 1% solution for standby；
3) acrylic acid methyl ester., monobutyl itaconate, vinyl chloroacetate, n- dodecyl mereaptan and deionized water, dodecane
Base sodium sulfate puts into stirring container, stirs 1 hour, is passed through nitrogen.Container is heated to 20 DEG C, stops heating, and input azo two is different
Ding Qing, half amount ferrous sulfate, emulsion system start temperature rise, and polyreaction starts, polymerization time about 1 hour, temperature rise peak
38.8℃.Input half measures ferrous sulfate, continues stirring 1 hour.After container is cooled to room temperature, calcium chloride is added, separate out white
Rubber grain, obtains finished product through rinsing dehydration, and yield is 98.1%.
Example IV：The preparation method of the present embodiment polyacrylate composition：
1) formula meter includes：
2) benzoyl peroxide, sodium thiosulfate, magnesium chloride, ethanol deionized water are diluted to 1% solution for standby
3) butyl acrylate, acrylic acid tirethylene glycol methyl ether ester, glycidyl methacrylate, n- dodecyl mereaptan
With deionized water, sodium lauryl sulphate input stirring container, stir 1 hour, be passed through nitrogen.Container is heated to 80 DEG C, stops
Heating, puts into benzoyl peroxide, and emulsion system starts temperature rise, and polyreaction starts, polymerization time about 1 hour, and temperature rise is most
99.5 DEG C of high point.Input sodium thiosulfate, continues stirring 1 hour.After container is cooled to room temperature, magnesium chloride, ethanol, analysis is added
Going out white rubber granule, finished product being obtained through rinsing dehydration, yield is 98.7%.
Embodiment five：The preparation method of the present embodiment polyacrylate composition：
1) formula meter includes：
2) Ammonium persulfate., sodium sulfite, polyacrylamide, sodium chloride deionized water are diluted to 1% solution for standby
3) acrylic acid methyl ester., ethylidene norbornene and deionized water, sodium lauryl sulphate input stirring container, stirring
1 hour, it is passed through nitrogen.Container is heated to 30 DEG C, stops heating, and input Ammonium persulfate., half amount sodium sulfite, emulsion system start
Temperature rise, polyreaction start, polymerization time about 1 hour, 49.1 DEG C of temperature rise peak.Input half measures sodium sulfite, continues to stir
Mix 1 hour.After container is cooled to room temperature, sodium chloride, polyacrylamide is added, separate out white rubber granule, through rinsing dehydration
Finished product is obtained, and yield is 99%.
In a word in being embodied as, generate polyacrylate composition acrylic ester monomer can be acrylic acid methyl ester.,
Ethyl acrylate, butyl acrylate, Isooctyl acrylate monomer, methoxyethyl acrylate, ethoxyethyl acrylate, acrylic acid first
One kind or several in epoxide butyl ester and acrylic acid tirethylene glycol methyl ether ester, the cross-linkable monomer can be monoxone
Vinyl acetate, allyl chloroacetate, ethyl maleate, monobutyl itaconate, glycidyl methacrylate, allyl glycidyl
One or two in glycerin ether, ethylidene norbornene.
And in the preparation method of polyacrylate composition, the regulator can be n- dodecyl mereaptan, tert-dodecyl mercaptan and
One kind in diisopropylbenzene (DIPB) xanthate, two or three；The emulsifying agent can be dodecyl sodium sulfate, detergent alkylate sulphur
One or two in sour sodium, sodium lauryl sulphate, disproportionated rosin soap；The free radical donor can be two isobutyl of azo fine,
Two different heptan of azo is fine, isopropyl benzene hydroperoxide, tert-butyl hydroperoxide, benzoyl peroxide, cumyl peroxide, peroxidating
One kind in di-t-butyl, Ammonium persulfate., potassium peroxydisulfate and sodium peroxydisulfate, when free radical donor is used alone, polyreaction
Temperature is 50-100 DEG C, and when free radical donor and reducing agent are used in conjunction with, polymeric reaction temperature is 5-50 DEG C；The flocculating agent
Can be dilute sulfuric acid, dilute hydrochloric acid, sodium chloride, magnesium chloride, calcium chloride, aluminum chloride, poly-ferric chloride, aluminium polychlorid, polypropylene
One kind or several in amide and ethanol.
Various embodiments above polyacrylate composition and preparation method thereof, preparation process are completely without additional heat exchange
Carry out in the case of means, reaction system temperature rise is less than 20 DEG C, and polymerisation conversion is up to 98-99%, and mild condition has completely
Standby industrial applications condition.
Finally illustrate, above example is only unrestricted in order to technical scheme to be described, 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 (2)
1. a kind of polyacrylate composition, it is characterised in that：For acrylic ester monomer and the copolymer of cross-linkable monomer, institute
The mass fraction for stating acrylic ester monomer in copolymer is 90-99%, and the mass fraction of cross-linkable monomer is 1-10%；Described
Acrylic ester monomer is acrylic acid methyl ester., ethyl acrylate, butyl acrylate, Isooctyl acrylate monomer, methoxyethyl second
One kind or some in ester, ethoxyethyl acrylate, methoxyethyl butyl ester and acrylic acid tirethylene glycol methyl ether ester
Kind, the cross-linkable monomer is vinyl chloroacetate, allyl chloroacetate, ethyl maleate, monobutyl itaconate, methyl-prop
One or two in olefin(e) acid ethylene oxidic ester, allyl glycidyl ether, ethylidene norbornene.
2. the preparation method of polyacrylate composition described in a kind of claim 1, it is characterised in that：
Acrylic ester monomer raw material, cross-linkable monomer raw material and regulator are added in emulsifier aqueous solution, is protected in nitrogen
Under shield, copolymerization is caused by free radical；And after the completion of copolymerization, add reducing agent to carry out post processing；Finally plus
Enter flocculating agent breakdown of emulsion, rinse through clear water, dehydration obtains polyacrylate composition；
The regulator be n- dodecyl mereaptan, tert-dodecyl mercaptan and diisopropylbenzene (DIPB) xanthate in one kind, two or three, institute
The consumption for stating regulator is the 0-0.2% of acrylic ester monomer raw material and cross-linkable monomer raw material gross mass；
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, and free radical donor is that two isobutyl of azo is fine, two different heptan of azo is fine, isopropyl
Benzene hydrogen peroxide, tert-butyl hydroperoxide, benzoyl peroxide, cumyl peroxide, di-t-butyl peroxide, persulfuric acid
One kind in ammonium, potassium peroxydisulfate and sodium peroxydisulfate；The consumption of the free radical donor is acrylic ester monomer raw material and friendship
The a ten thousandth of connection property raw material monomer gross mass is to 2/1000ths；
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 and ethanol, it is acrylic ester monomer raw material that the flocculating agent is consumption
1-5% with cross-linkable monomer raw material gross mass.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201611091589.6A CN106496405A (en) | 2016-12-01 | 2016-12-01 | Polyacrylate composition and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611091589.6A CN106496405A (en) | 2016-12-01 | 2016-12-01 | Polyacrylate composition and preparation method thereof |
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| CN201611091589.6A Pending CN106496405A (en) | 2016-12-01 | 2016-12-01 | Polyacrylate composition and preparation method thereof |
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Cited By (2)
| 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 |
| CN110181957A (en) * | 2019-05-23 | 2019-08-30 | 新乡市新贝尔信息材料有限公司 | A kind of stamp colour band of low temperature resistant printing and preparation method thereof |
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| CN101597355A (en) * | 2009-05-27 | 2009-12-09 | 彭文表 | A kind of water-based room temperature crosslinking acrylic acid emulsion and preparation method thereof |
| CN102140150A (en) * | 2011-03-11 | 2011-08-03 | 安徽时代创新科技投资发展有限公司 | Preparation method for acrylic ester rubber |
| CN104558382A (en) * | 2014-12-26 | 2015-04-29 | 上海金兆节能科技有限公司 | Polyacrylate composition, preparation method of polyacrylate composition and environment friendly micro lubricating oil prepared from polyacrylate |
| CN104804126A (en) * | 2015-04-17 | 2015-07-29 | 广州杰锐体育设施有限公司 | Modified self-crosslinking water-based acrylic resin and preparation method thereof |
| CN105085785A (en) * | 2015-08-13 | 2015-11-25 | 新东方油墨有限公司 | Environmentally-friendly cross-linked acrylate polymer emulsion and preparation method thereof |
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2016
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101597355A (en) * | 2009-05-27 | 2009-12-09 | 彭文表 | A kind of water-based room temperature crosslinking acrylic acid emulsion and preparation method thereof |
| CN102140150A (en) * | 2011-03-11 | 2011-08-03 | 安徽时代创新科技投资发展有限公司 | Preparation method for acrylic ester rubber |
| CN104558382A (en) * | 2014-12-26 | 2015-04-29 | 上海金兆节能科技有限公司 | Polyacrylate composition, preparation method of polyacrylate composition and environment friendly micro lubricating oil prepared from polyacrylate |
| CN104804126A (en) * | 2015-04-17 | 2015-07-29 | 广州杰锐体育设施有限公司 | Modified self-crosslinking water-based acrylic resin and preparation method thereof |
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Cited By (2)
| 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 |
| CN110181957A (en) * | 2019-05-23 | 2019-08-30 | 新乡市新贝尔信息材料有限公司 | A kind of stamp colour band of low temperature resistant printing and preparation method thereof |
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