CN102653583A - Preparation method of amphiphilic segmented copolymer - Google Patents
Preparation method of amphiphilic segmented copolymer Download PDFInfo
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- CN102653583A CN102653583A CN2012100413039A CN201210041303A CN102653583A CN 102653583 A CN102653583 A CN 102653583A CN 2012100413039 A CN2012100413039 A CN 2012100413039A CN 201210041303 A CN201210041303 A CN 201210041303A CN 102653583 A CN102653583 A CN 102653583A
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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
- 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
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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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
Abstract
The invention discloses a preparation method of an amphiphilic segmented copolymer, and the method comprises the following steps of: preparing seed microemulsion and a pre-emulsified mixed monomer, triggering the seed microemulsion to have a microemulsion polymerization reaction, adding the pre-emulsified mixed monomer to obtain an acrylate polymer, and reacting the acrylate polymer with a hydrophilic monomer, to obtain the amphiphilic segmented copolymer. In the preparation method, the microemulsion polymerization is stable in reaction thermodynamics system, and the dispersed phase is smaller in size, according to the preparation method, the granularity of the polymer emulsion can be evenly distributed, and the emulsion is stable in performance. The segmented copolymer synthesized by the method has better appetency to the hydrophilic fiber and the hydrophobic dye, so that the surface of the natural fiber can be improved, and simultaneously the organic dye dispersing system is good in stability.
Description
Technical field
The present invention relates to the prize pigment dispersing agent of film of liquid-crystal display, be specifically related to a kind of method for preparing amphiphilic block copolymer.
Background technology
Amphiphilic block copolymer is meant and in same polymer, had both contained hydrophilic segment, contains the multipolymer of hydrophobic segment again.With common polymer phase ratio, amphiphilic block copolymer has many special propertys, like surfactivity, lyotropy and thickening property.
Letex polymerization (emulsion polymerization) is a kind of compound method commonly used in the Polymer Synthesizing process, and is because it is with water as solvent, very favourable to environment.Emulsion polymerization is under the effect of emulsifying agent and by mechanical stirring, makes monomer in water, be dispersed into milk sap, the polyreaction of being undertaken by the initiator initiation.
One Chinese patent application CN 101870759A discloses a kind of method of synthesis of amphoteric segmented copolymer, and what this method adopted is common emulsion polymerization synthesis of amphoteric block polymer.Yet this emulsion is muddy Unstable Systems, and its thermodynamic system is unstable, and dispersed phase size is bigger, makes chemical reaction system unstable, and the distribution and the stability of pigment particle size is had certain influence.
Summary of the invention
The technical problem that the present invention will solve is the thermodynamic stability that how to strengthen the amphiphilic block copolymer system.
In order to solve the problems of the technologies described above, the present invention provides a kind of method for preparing amphiphilic block copolymer.
The method that the present invention prepares amphiphilic block copolymer comprises the steps: to prepare seed microemulsion and preparatory emulsification mix monomer; Cause the seed microemulsion and carry out the micro emulsion polyreaction; Add preparatory emulsification mix monomer and obtain acrylic ester polymer; Itself and hydrophilic monomer are reacted, obtain amphiphilic block copolymer.
Said seed microemulsion prepares through following steps: the emulsifying agent with 60～75% mixes with water, obtains emulsion through magnetic agitation, under ultrasonic agitation, adds 25～40% acrylic acid or the like hydrophobic monomer, obtains the seed microemulsion.
Wherein, the volume ratio of emulsifying agent, water, acrylic acid or the like hydrophobic monomer is preferably (1～2): (25～50): (10～20); The rotating speed of magnetic agitation is 300～330rad/min; The time of magnetic agitation is 25～35min.
Said preparatory emulsification mix monomer prepares through following steps: the emulsifying agent with 25～40% mixes with water, under magnetic agitation, adds 60～75% acrylic acid or the like hydrophobic monomer, obtains preparatory emulsification mix monomer.
Wherein the volume ratio of emulsifying agent, water, acrylic acid or the like hydrophobic monomer is preferably (1～2): (50～100): (50～80); The rotating speed of magnetic agitation is 400～430rad/min; The time of magnetic agitation is 25～35min.
Said acrylic ester polymer prepares through following steps: in the seed microemulsion, add alkali, catalyzer, part and initiator, cause the micro emulsion polymerization; , the seed microemulsion is warming up to 80～85 ℃ after presenting blue light; Slowly drip preparatory emulsification mix monomer; Drip off in 2～3h, lower the temperature behind insulation slaking 0.5～1h, regulating pH is 9～11, reaction product is vacuumized, and cooling under shielding gas, suction filtration, washing, drying obtains acrylic ester polymer.
Wherein, used seed microemulsion, the volume ratio of emulsification mix monomer, alkali, catalyzer, part, initiator is preferably (72～144) in advance: (101～182): (0.05～0.15): (1～2): (2～3): (1～2).
Through acrylic ester polymer is mixed with hydrophilic monomer, under shielding gas, in water-bath, react 50～80min, cooling, suction filtration, washing, drying obtains amphiphilic block copolymer.
Wherein, the temperature of water-bath is 25～35 ℃; The volume ratio of acrylic ester polymer and hydrophilic monomer is 1: (2～4).
Said acrylic acid or the like hydrophobic monomer is selected from one or more in methyl acrylate, ethyl propenoate, NSC 20949, TEB 3K and the Jia Jibingxisuanyizhi.
Said hydrophilic monomer is selected from one or more in acrylic amide, USAF RH-1, Ucar 35 and the USP Kosher.
Said initiator is selected from persulphate or hydrogen peroxide or derivatives thereof.Preferably, said initiator is Sodium Persulfate or Potassium Persulphate.
Said emulsifying agent is selected from one or more in Teepol, X 2073 and the triton x-100.
Said catalyzer is selected from one or more in cupric bromide, iron bromide, cupric chloride and the iron(ic)chloride.
Said part is selected from 2-methyl-5-vinylpyrine, 3-vinyl pyridine, 4, a kind of in 4-dipyridyl and the pentamethyl-diethylenetriamine.
Said alkali is selected from one or more in sodium hydrogencarbonate, yellow soda ash and the sodium hydroxide.
Said shielding gas is nitrogen or rare gas element.
The present invention is through adopting microemulsion polymerization method synthesis of amphoteric segmented copolymer.Micro-emulsion polymerization is littler with the droplet size dispersion of disperse phase, and the droplet diameter that can make disperse phase is in 10～100nm scope.In microemulsion system, it is that one deck laminated film that forms through emulsifying agent and assistant for emulsifying agent and interfacial layer keep that it is stable that microballon drips.
Because micro-emulsion polymerization has thermodynamically stable characteristic; And dispersed phase size features of smaller in the microemulsion, the Amphiphilic Block Polymers system Thermodynamically stable that the present invention utilizes the polymerization of microemulsion method to obtain, dispersed phase size is less; Between 21.5～33nm, even size distribution and stable.With this method synthetic amphiphilic block copolymer hydrophilic fiber and hydrophobic pigment all there are avidity preferably, can carry out modification, simultaneously there is excellent stabilization in organic pigment dispersions system surface of natural fibers.Therefore, can be used as the prize pigment dispersing agent of film of liquid-crystal display.
Embodiment
Following examples are used to explain the present invention, but are not used for limiting scope of the present invention.
Each item performance of the amphiphilic block copolymer that compound method of the present invention obtains can adopt following index to detect:
1. multipolymer viscosity: the viscosity that adopts BROOKFIELD DV-C digital display viscometer determining adhesive agent emulsion.
2. copolymer particle particle diameter and size distribution: adopt Nano ZS particle size analyzer determination segmented copolymer particle size of emulsion and size distribution.
3. molecular weight of copolymer and dispersion index: adopt Waters515 gel permeation chromatography test polymer molecular weight and MWD, probe temperature is 25 ℃, and moving phase is THF, and flow velocity is 1.0ml/min, and standard is a PS.
For exemplary but the present invention is described without limitation, in following examples, the acrylic acid or the like hydrophobic monomer is selected from methyl acrylate, NSC 20949 and TEB 3K; Hydrophilic monomer is selected from acrylic amide, USAF RH-1 and Ucar 35; Initiator is selected from Sodium Persulfate and Potassium Persulphate; Emulsifying agent is selected from Teepol and X 2073; Catalyzer is selected from cupric bromide and iron bromide; Part is selected from 2-methyl-5-vinylpyrine, 3-vinyl pyridine and 4,4-dipyridyl; Used alkali is selected from sodium hydrogencarbonate and yellow soda ash.
For exemplary but the present invention is described without limitation, in following examples, when preparation seed microemulsion, the volume ratio of emulsifying agent, water, acrylic acid or the like hydrophobic monomer is (1～2): (25～50): (10～20); When the preparatory emulsification mix monomer of preparation, the volume ratio of emulsifying agent, water, acrylic acid or the like hydrophobic monomer is (1～2): (50～100): (50～80); When the preparation acrylic ester polymer, the volume ratio of used seed microemulsion, preparatory emulsification mix monomer, alkali, catalyzer, part, initiator is (72～144): (101～182): (0.05～0.15): (1～2): (2～3): (1～2); The volume ratio of acrylic ester polymer and hydrophilic monomer is 1: (2～4).
Embodiment 1
(1) 4ml Teepol, 100ml deionized water being joined in the band side-tube flask, is to stir 30min under the magnetic agitation of 300rad/min to obtain emulsion at rotating speed, under ultrasonic stirring, adds the 30ml methyl acrylate and obtains translucent seed microemulsion;
(2) 2ml Teepol, 100ml deionized water being joined in the band side-tube flask, is to add the 60ml methyl acrylate under the magnetic agitation of 400rad/min at rotating speed, and magnetic agitation 30min obtains preparatory emulsification mix monomer;
(3) in the seed microemulsion that step (1) obtains, add 0.1ml yellow soda ash, 2ml cupric bromide, 2ml 2-methyl-5-vinylpyrine, 2ml Sodium Persulfate, cause the micro emulsion polymerization; After the seed microemulsion presents blue light, be warming up to 85 ℃, slowly drip the preparatory emulsification mix monomer that step (2) obtains, drip off in the 2h; Lower the temperature behind the insulation slaking 0.5h, regulate pH to 10, the reaction product sealing is vacuumized; Make vacuum tightness reach behind the 40kPa again applying argon gas to normal pressure, three times repeatedly; Under the argon gas existence condition, reaction product is cooled off 20min in frozen water, to greenhouse cooling to 20 ℃, reaction product is carried out suction filtration; The solid that suction filtration obtains is with deionized water rinsing 3 times, and vacuum drying 4h obtains acrylic ester polymer under 50 ℃ of conditions;
(4) 1 part of (250ml) acrylic ester polymer and 2 parts of (500ml) USAF RH-1s are mixed in the band side-tube flask, sealing vacuumizes, and makes vacuum tightness reach behind the 20kPa applying argon gas to normal pressure, three times repeatedly again; Under the condition in the presence of the argon gas; Flask is put into 30 ℃ of water-baths react 50min; The taking-up flask is put into ice-water bath and is cooled off 30min, reduces to 20 ℃ to temperature, migrates out the reaction product and the suction filtration that obtain; With the solid that obtains with deionized water rinsing 4 times after, vacuum drying 4h obtains amphiphilic block copolymer under 50 ℃ of conditions.
Embodiment 2
(1) 2ml X 2073,50ml deionized water are joined in the band side-tube flask; Be to stir 30min under the magnetic agitation of 330rad/min to obtain emulsion at rotating speed, under ultrasonic stirring, add the 20ml methyl acrylate and obtain translucent seed microemulsion;
(2) 1ml X 2073,50ml deionized water being joined in the band side-tube flask, is to add the 50ml methyl acrylate under the magnetic agitation of 430rad/min at rotating speed, and magnetic agitation 30min obtains preparatory emulsification mix monomer;
(3) in the seed microemulsion that step (1) obtains, add 0.05ml yellow soda ash, 1ml cupric bromide, 2ml 3-vinyl pyridine, 1ml Potassium Persulphate, cause the micro emulsion polymerization; After the seed microemulsion presents blue light, be warming up to 85 ℃, slowly drip the preparatory emulsification mix monomer that step (2) obtains, drip off in the 2h; Lower the temperature behind the insulation slaking 0.5h, regulate pH to 10, the reaction product sealing is vacuumized; Make vacuum tightness reach behind the 40kPa again applying argon gas to normal pressure, three times repeatedly; Under the argon gas existence condition, reaction product is cooled off 20min in frozen water, to greenhouse cooling to 20 ℃, reaction product is carried out suction filtration; The solid that suction filtration obtains is with deionized water rinsing 3 times, and vacuum drying 4h obtains acrylic ester polymer under 50 ℃ of conditions;
(4) 1 part of (100ml) acrylic ester polymer and 2 parts of (200ml) Ucar 35 are mixed in the band side-tube flask, sealing vacuumizes, and makes vacuum tightness reach behind the 20kPa applying argon gas to normal pressure, three times repeatedly again; Under the condition in the presence of the argon gas; Flask is put into 30 ℃ of water-baths react 50min; The taking-up flask is put into ice-water bath and is cooled off 30min, reduces to 20 ℃ to temperature, migrates out the reaction product and the suction filtration that obtain; With the solid that obtains with deionized water rinsing 4 times after, vacuum drying 4h obtains amphiphilic block copolymer under 50 ℃ of conditions.
Embodiment 3
(1) 6ml Teepol, 150ml deionized water are joined in the band side-tube flask; Be to stir 35min under the magnetic agitation of 300rad/min to obtain emulsion at rotating speed, under ultrasonic stirring, add the 45ml TEB 3K and obtain translucent seed microemulsion;
(2) 3ml Teepol, 150ml deionized water being joined in the band side-tube flask, is to add the 90ml TEB 3K under the magnetic agitation of 400rad/min at rotating speed, and magnetic agitation 30min obtains preparatory emulsification mix monomer;
(3) in the seed microemulsion that step (1) obtains, add 0.15ml sodium hydrogencarbonate, 2ml iron bromide, 3ml 4,4-dipyridyl, 2ml Sodium Persulfate cause the micro emulsion polymerization; After the seed microemulsion presents blue light, be warming up to 80 ℃, slowly drip the preparatory emulsification mix monomer that step (2) obtains, drip off in the 3h; Lower the temperature behind the insulation slaking 1h, regulate pH to 9, the reaction product sealing is vacuumized; Make vacuum tightness reach behind the 40kPa again applying argon gas to normal pressure, three times repeatedly; Under the argon gas existence condition, reaction product is cooled off 15min in frozen water, to greenhouse cooling to 20 ℃, reaction product is carried out suction filtration; The solid that suction filtration obtains is with deionized water rinsing 3 times, and vacuum drying 4h obtains acrylic ester polymer under 50 ℃ of conditions;
(4) 1 part of (400ml) acrylic ester polymer and 2 parts of (800ml) acrylic amides are mixed in the band side-tube flask, sealing vacuumizes, and makes vacuum tightness reach behind the 20kPa applying argon gas to normal pressure, three times repeatedly again; Under the condition in the presence of the argon gas; Flask is put into 25 ℃ of water-baths react 60min; The taking-up flask is put into ice-water bath and is cooled off 30min, reduces to 20 ℃ to temperature, migrates out the reaction product and the suction filtration that obtain; With the solid that obtains with deionized water rinsing 4 times after, vacuum drying 4h obtains amphiphilic block copolymer under 50 ℃ of conditions.
Embodiment 4
(1) 40ml X 2073,1000ml deionized water are joined in the band side-tube flask; Be to stir 25min under the magnetic agitation of 320rad/min to obtain emulsion at rotating speed, under ultrasonic stirring, add the 300ml NSC 20949 and obtain translucent seed microemulsion;
(2) 20ml X 2073,1000ml deionized water being joined in the band side-tube flask, is to add the 600ml NSC 20949 under the magnetic agitation of 420rad/min at rotating speed, and magnetic agitation 30min obtains preparatory emulsification mix monomer;
(3) in the seed microemulsion that step (1) obtains, add 1ml yellow soda ash, 20ml cupric bromide, 20ml 3-vinyl pyridine, 20ml Potassium Persulphate, cause the micro emulsion polymerization; After the seed microemulsion presents blue light, be warming up to 85 ℃, slowly drip the preparatory emulsification mix monomer that step (2) obtains, drip off in the 2h; Lower the temperature behind the insulation slaking 0.5h, regulate pH to 11, the reaction product sealing is vacuumized; Make vacuum tightness reach behind the 40kPa again inflated with nitrogen to normal pressure, three times repeatedly; Under the nitrogen existence condition, reaction product is cooled off 20min in frozen water, to greenhouse cooling to 20 ℃, reaction product is carried out suction filtration; The solid that suction filtration obtains is with deionized water rinsing 3 times, and vacuum drying 4h obtains acrylic ester polymer under 50 ℃ of conditions;
(4) 1 part of (1200ml) acrylic ester polymer and 2 parts of (2400ml) Ucar 35 are mixed in the band side-tube flask, sealing vacuumizes, and makes vacuum tightness reach behind the 20kPa inflated with nitrogen to normal pressure, three times repeatedly again; Under the condition in the presence of the nitrogen; Flask is put into 25 ℃ of water-baths react 80min; The taking-up flask is put into ice-water bath and is cooled off 30min, reduces to 20 ℃ to temperature, migrates out the reaction product and the suction filtration that obtain; With the solid that obtains with deionized water rinsing 4 times after, vacuum drying 4h obtains amphiphilic block copolymer under 50 ℃ of conditions.
The amphiphilic block copolymer that embodiment 1～4 is obtained carries out performance test, and the result sees table 1:
Table 1
Can know by table 1, the amphiphilic block copolymer of the present invention's preparation, its particle diameter distribution width is between 21.5～33nm, and the dispersed phase size scope is less; The gained amphiphilic block copolymer all has avidity preferably to hydrophilic fiber and hydrophobic pigment, and its dispersion stabilization can be through characterizing the viscosity of pigment and the long-term follow test of granularity.Half a year to year, the prepared amphiphilic block copolymer of the inventive method is when the pigment dispersing agent, tangible growth takes place in the viscosity of pigment and granularity hardly, explains that it has good stability.
Can know that by technological general knowledge the present invention can realize through other the embodiment that does not break away from its spirit or essential feature.Therefore, above-mentioned disclosed embodiment with regard to each side, just illustrates, and is not only.All within the scope of the present invention or the change in being equal to scope of the present invention all be contained in protection scope of the present invention.
Claims (13)
1. method for preparing amphiphilic block copolymer; It is characterized in that; Comprise the steps: to prepare seed microemulsion and preparatory emulsification mix monomer, cause the seed microemulsion and carry out the micro emulsion polyreaction, add preparatory emulsification mix monomer and obtain acrylic ester polymer; Itself and hydrophilic monomer are reacted, obtain amphiphilic block copolymer.
2. method according to claim 1; It is characterized in that said seed microemulsion prepares through following steps: the emulsifying agent with 60～75% mixes with water, obtains emulsion through magnetic agitation; Under ultrasonic agitation, add 25～40% acrylic acid or the like hydrophobic monomer, obtain the seed microemulsion.
3. method according to claim 2 is characterized in that, the volume ratio of emulsifying agent, water, acrylic acid or the like hydrophobic monomer is (1～2): (25～50): (10～20).
4. method according to claim 2 is characterized in that, the rotating speed of magnetic agitation is 300～330rad/min, and the time of magnetic agitation is 25～35min.
5. method according to claim 1; It is characterized in that; Said preparatory emulsification mix monomer prepares through following steps: the emulsifying agent with 25～40% mixes with water, under magnetic agitation, adds 60～75% acrylic acid or the like hydrophobic monomer, obtains preparatory emulsification mix monomer.
6. method according to claim 5 is characterized in that, the volume ratio of emulsifying agent, water, acrylic acid or the like hydrophobic monomer is (1～2): (50～100): (50～80).
7. method according to claim 5 is characterized in that, the rotating speed of magnetic agitation is 400～430rad/min, and the time of magnetic agitation is 25～35min.
8. method according to claim 1 is characterized in that, said acrylic ester polymer prepares through following steps: in said seed microemulsion, add alkali, catalyzer, part and initiator, cause the micro emulsion polymerization; , the seed microemulsion is warming up to 80～85 ℃ after presenting blue light; Slowly drip said preparatory emulsification mix monomer; Drip off in 2～3h, lower the temperature behind insulation slaking 0.5～1h, regulating pH is 9～11, reaction product is vacuumized, and cooling under shielding gas, suction filtration, washing, drying obtains acrylic ester polymer.
9. method according to claim 8; It is characterized in that the volume ratio of used seed microemulsion, preparatory emulsification mix monomer, alkali, catalyzer, part, initiator is (72～144): (101～182): (0.05～0.15): (1～2): (2～3): (1～2).
10. method according to claim 1 is characterized in that, through acrylic ester polymer is mixed with hydrophilic monomer, under shielding gas, in water-bath, reacts 50～80min, cooling, and suction filtration, washing, drying obtains amphiphilic block copolymer.
11. method according to claim 10 is characterized in that, the temperature of water-bath is 25～35 ℃.
12. method according to claim 10 is characterized in that, the volume ratio of acrylic ester polymer and hydrophilic monomer is 1: (2～4).
13. the amphiphilic block copolymer that each described preparation method of claim 1～12 obtains is as the application of pigment dispersing agent.
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| CN201210041303.9A CN102653583B (en) | 2012-02-21 | 2012-02-21 | Preparation method of amphiphilic segmented copolymer |
| PCT/CN2012/087228 WO2013123811A1 (en) | 2012-02-21 | 2012-12-23 | Process for preparing amphiphilic block copolymer |
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| WO2013123811A1 (en) * | 2012-02-21 | 2013-08-29 | 京东方科技集团股份有限公司 | Process for preparing amphiphilic block copolymer |
| CN109971375A (en) * | 2019-04-15 | 2019-07-05 | 江苏南方卫材医药股份有限公司 | A kind of method of adhesive waterproof tape substrate and gluing |
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| CN115536791B (en) * | 2022-10-26 | 2023-05-26 | 安徽工程大学 | Starch slurry with same substituent group connected into two diblock polymer chains, and preparation method and application thereof |
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| CN101870759A (en) * | 2010-06-24 | 2010-10-27 | 江南大学 | Synthesis method of amphiphilic block copolymer |
| CN102040711A (en) * | 2010-11-09 | 2011-05-04 | 华南理工大学 | Amphiphilic polymer pigment wetting dispersant for water-based coating and preparation method thereof |
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| CN1208359C (en) * | 2002-11-26 | 2005-06-29 | 北京服装学院 | Modified polyacrylate microemulsion, synthesis mehtod and use thereof |
| KR101299148B1 (en) * | 2010-07-21 | 2013-08-22 | (주)바이오제닉스 | Preparation method of microemulsion comprising egcg |
| CN102653583B (en) * | 2012-02-21 | 2014-11-12 | 京东方科技集团股份有限公司 | Preparation method of amphiphilic segmented copolymer |
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| CN101870759A (en) * | 2010-06-24 | 2010-10-27 | 江南大学 | Synthesis method of amphiphilic block copolymer |
| CN102040711A (en) * | 2010-11-09 | 2011-05-04 | 华南理工大学 | Amphiphilic polymer pigment wetting dispersant for water-based coating and preparation method thereof |
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| 郑根稳等: "预乳化法制备纯丙微乳液", 《孝感学院学报》 * |
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| WO2013123811A1 (en) * | 2012-02-21 | 2013-08-29 | 京东方科技集团股份有限公司 | Process for preparing amphiphilic block copolymer |
| CN109971375A (en) * | 2019-04-15 | 2019-07-05 | 江苏南方卫材医药股份有限公司 | A kind of method of adhesive waterproof tape substrate and gluing |
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