CN111285971B - Preparation method of polyvinyl pyrrolidone/chlorinated polyethylene water-swelling rubber - Google Patents
Preparation method of polyvinyl pyrrolidone/chlorinated polyethylene water-swelling rubber Download PDFInfo
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- CN111285971B CN111285971B CN202010154004.0A CN202010154004A CN111285971B CN 111285971 B CN111285971 B CN 111285971B CN 202010154004 A CN202010154004 A CN 202010154004A CN 111285971 B CN111285971 B CN 111285971B
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 65
- 239000005060 rubber Substances 0.000 title claims abstract description 65
- 239000004709 Chlorinated polyethylene Substances 0.000 title claims abstract description 26
- 229920000036 polyvinylpyrrolidone Polymers 0.000 title claims abstract description 26
- 239000001267 polyvinylpyrrolidone Substances 0.000 title claims abstract description 26
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229920006235 chlorinated polyethylene elastomer Polymers 0.000 claims abstract description 18
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000002791 soaking Methods 0.000 claims abstract description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 10
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 abstract description 20
- 229920001477 hydrophilic polymer Polymers 0.000 abstract description 11
- 229920000578 graft copolymer Polymers 0.000 abstract description 8
- 238000010526 radical polymerization reaction Methods 0.000 abstract description 8
- 230000008569 process Effects 0.000 abstract description 7
- 238000011065 in-situ storage Methods 0.000 abstract description 6
- 239000003431 cross linking reagent Substances 0.000 abstract description 5
- 239000000178 monomer Substances 0.000 abstract description 5
- 230000008961 swelling Effects 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 238000004132 cross linking Methods 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000002250 absorbent Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 239000011358 absorbing material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002464 physical blending Methods 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000001902 propagating effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229940080314 sodium bentonite Drugs 0.000 description 1
- 229910000280 sodium bentonite Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
- C08F255/023—On to modified polymers, e.g. chlorinated polymers
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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)
- Graft Or Block Polymers (AREA)
Abstract
The invention belongs to the technical field of high-molecular graft copolymers and preparation thereof, and relates to a preparation method of polyvinyl pyrrolidone/chlorinated polyethylene water-swelling rubber. The invention firstly uses hydrophilic monomer N-vinyl pyrrolidone dissolved with initiator and cross-linking agent to swell chlorinated polyethylene rubber, and then carries out free radical polymerization to obtain the polyvinyl pyrrolidone/chlorinated polyethylene water-absorbing swelling rubber. This first swelling and then polymerizing process allows the hydrophilic polymer formed in situ to be uniformly and efficiently dispersed in the rubber matrix. Further, the preparation method obtains a graft copolymer of a rubber molecular chain grafted with a hydrophilic polymer, and a three-dimensional space network structure is formed in the presence of a cross-linking agent. The combined action of grafting and crosslinking enables the hydrophilic dispersed phase and the rubber matrix to be firmly connected together, effectively inhibits the loss of the hydrophilic polymer after soaking in water, and obviously improves the stability of the water-swellable rubber.
Description
Technical Field
The invention belongs to the technical field of high-molecular graft copolymers and preparation thereof, and particularly relates to a preparation method of polyvinyl pyrrolidone/chlorinated polyethylene water-swelling rubber.
Background
The water-swellable rubber is a composite material composed of a hydrophilic material and rubber, wherein the rubber is used as a continuous phase, and the hydrophilic material is generally dispersed in the rubber in a micron-sized size. After the water-swelling rubber contacts water, the hydrophilic material particles can absorb water to cause the volume expansion of the water-swelling rubber, and when the centripetal contraction force caused by the expansion of the rubber substrate and the expansion force caused by the water absorption of the internal hydrophilic material are balanced, the water-swelling rubber reaches the maximum water-swelling multiplying power. The water-absorbing expansion rubber has the characteristics of water-absorbing expansion sealing and water stopping, and is widely used as sealing and leakage-stopping materials for engineering deformation joints, construction joints, pipeline joints and the like of engineering such as subways, tunnels, highways, underground buildings and the like and for on-site quick leakage stopping of dams. The 1970 s of research and development began in japan, and subsequently, countries in europe and america conducted intensive theoretical and application research thereon. Although the development of China is late, the development is remarkable under the efforts of the majority of scientific researchers.
The preparation methods of the common water-swelling rubber at present mainly comprise two types: physical blending and chemical grafting.
The physical blending type water-swelling rubber is prepared by cutting water-absorbing materials into micron-sized small particles with strong shearing force, dispersing the micron-sized small particles in a rubber matrix, and then vulcanizing and crosslinking the micron-sized small particles. The blending method is simple and low in cost, and both the rubber matrix and the water absorbing material have many choices. Alternative water-absorbing materials are: (1) natural high-molecular high-water-absorption resin, such as starch or cellulose grafted polyacrylate, and polyacrylamide; (2) synthetic super absorbent resins such as crosslinked poly (meth) acrylate, polyacrylamide, polyvinyl alcohol, and the like; (3) inorganic high-sodium bentonite and its modified product. The rubber matrix is generally selected from rubbers with certain polarity, such as chlorinated polyethylene rubber, chloroprene rubber and nitrile rubber, in order to increase the interfacial bonding force between the rubber matrix and the water-absorbent resin and inhibit the loss of the water-absorbent resin. It is preferable to add a graft type (or block type) compatibilizer to further strengthen the interfacial bonding force. However, the water-absorbent resin has poor compatibility with the rubber matrix due to large cohesive force of the water-absorbent resin, and is not well dispersed in the rubber matrix; and the water-absorbent resin and the rubber matrix are not combined by chemical bonds, so the water-absorbent resin is easy to be desorbed from the rubber after being soaked in water, and the water-absorbent expansion rate and the mechanical property are increasingly poor along with the service time.
The chemically grafted water-swellable rubber is obtained by grafting a hydrophilic polymer chain onto a rubber molecule chain through a chemical reaction. Compared with the blended type, the water-absorbing resin has good dispersibility, strong interface binding force with a rubber matrix and strong water-absorbing expansion stability. CN201410122582 discloses a preparation method of a graft modified chlorine-containing polymer film with durable hydrophilicity. The process of this patent application consists in removing the HCl from the chlorine-containing polymer chain by means of a strong base, in forming unsaturated bonds in the chain, and in grafting a hydrophilic polymer onto the chlorine-containing polymer chain by means of free-radical polymerization. The method has the disadvantages of low grafting ratio (more hydrophilic homopolymer is generated), more complicated steps and higher cost.
Disclosure of Invention
Previous research results show that chlorinated polyethylene can be swelled by some vinyl monomers, then free radical polymerization is initiated, and free radical chain transfer occurs in the polymerization process to form a chlorinated polyethylene graft copolymer. Based on this, the present inventors have found that a hydrophilic monomer, N-vinylpyrrolidone (NVP), can swell a chlorinated polyethylene rubber in a wide range of composition ratios, and then initiate polymerization thereof to form a water-swellable rubber.
The invention aims to avoid the defects in the prior art and provides a preparation method of polyvinyl pyrrolidone/chlorinated polyethylene water-swelling rubber. The purpose of the invention is realized by the following technical scheme:
1. a preparation method of polyvinyl pyrrolidone/chlorinated polyethylene water-swelling rubber is characterized by comprising the following steps:
dissolving azodiisobutyronitrile and 1, 6-hexanediol diacrylate in N-vinyl pyrrolidone, then putting the N-vinyl pyrrolidone in which azodiisobutyronitrile and 1, 6-hexanediol diacrylate are dissolved and chlorinated polyethylene rubber into a reactor, uniformly mixing, introducing nitrogen to remove oxygen, heating to 70 ℃, reacting for 6 hours, taking out a product after the reaction is finished, soaking and washing the product in deionized water for 120 hours, and drying in vacuum at 60 ℃ to constant weight to obtain the polyvinyl pyrrolidone/chlorinated polyethylene water-absorbing expansion rubber.
2. The method for preparing polyvinylpyrrolidone/chlorinated polyethylene water-swellable rubber according to claim 1, characterized in that: the mass ratio of the N-vinyl pyrrolidone to the chlorinated polyethylene rubber is 1: 4-1: 2.
3. The method for preparing polyvinylpyrrolidone/chlorinated polyethylene water-swellable rubber according to claim 1, characterized in that: the azodiisobutyronitrile accounts for 0.5mol percent of the N-vinyl pyrrolidone.
4. The method for preparing polyvinylpyrrolidone/chlorinated polyethylene water-swellable rubber according to claim 1, characterized in that: the 1, 6-hexanediol diacrylate accounts for 1-3 mol% of the N-vinyl pyrrolidone.
In the technical scheme, the chlorinated polyethylene rubber (CPE) is rubber with stronger polarity, stronger interaction exists between the chlorinated polyethylene rubber and polar polyvinylpyrrolidone (PVP), and the chlorinated polyethylene rubber and the polar polyvinylpyrrolidone (PVP) have better compatibility, so that the stability of the water-swelling rubber can be improved.
The hydrophilic monomer-N-vinyl pyrrolidone-can swell the chlorinated polyethylene rubber in a wider composition ratio range, namely the N-vinyl pyrrolidone is uniformly distributed in the rubber matrix, so that a hydrophilic dispersion phase of the polyvinyl pyrrolidone can be generated in situ in the rubber matrix through free radical polymerization, and the in-situ polymerization process can ensure that the hydrophilic phase is uniformly dispersed and the size of the dispersion phase is small. Furthermore, chain transfer of the primary radicals (or propagating radicals) to the C-Cl bonds on the rubber molecular chain during in situ free radical polymerization forms a rubber/polyvinylpyrrolidone graft copolymer. The graft copolymer can increase the interface bonding force between the hydrophilic dispersion phase and the rubber matrix, inhibit the loss of hydrophilic components and improve the stability of the water-swelling rubber.
1, 6-hexanediol diacrylate is a diene cross-linking agent with a flexible chain, and after the cross-linking agent is added, a hydrophilic polymer with a three-dimensional network structure is generated, the hydrophilic polymer has the functions of controlling the water absorption expansion rate, and the other functions of inhibiting the loss of a hydrophilic component and increasing the stability. Through the combined action of chain transfer and diene crosslinking agents, the CPE rubber matrix is crosslinked to a certain degree, a special vulcanization step is omitted, the hydrophilic dispersion phase and the rubber matrix are crosslinked into a whole, and the stability of the polyvinyl pyrrolidone/chlorinated polyethylene water-absorbing expansion rubber is greatly improved.
The hydrophilic monomer N-vinyl pyrrolidone inevitably forms a small amount of free oligomer in the in-situ free radical polymerization process, only the cross-linked structure determines the water absorption and expansion performance from the physical perspective of high molecules, and the free oligomer has no effect. Therefore, after the polymerization is completed, the free oligomers are removed by washing with deionized water.
Compared with the prior art, the invention has the following advantages:
(1) the invention uses hydrophilic alkene monomer to swell CPE rubber matrix, then initiates free radical polymerization in the swollen rubber, namely the hydrophilic polymer is generated in situ in the rubber matrix. The process can make the hydrophilic polymer dispersed homogeneously inside the rubber matrix and the dispersed hydrophilic phase has small size.
(2) In addition, the C-Cl bonds on the molecular chain of the CPE rubber are relatively weak and are susceptible to chain transfer with initiating (or propagating) radicals, thus forming a CPE/PVP graft copolymer during free radical polymerization in a swollen rubber matrix. The existence of the graft copolymer strengthens the binding force between the hydrophilic phase of the hydrophilic polymer and the rubber matrix phase, thereby inhibiting the loss of the hydrophilic polymer in the water-absorbing expansion process and improving the stability.
(3) The preparation method of the water-swelling rubber has the advantages of simple process, moderate water-swelling rate of the product and good mechanical property after water-swelling, and can be used for water prevention and water stopping and leakage stopping in various civil construction processes.
Detailed Description
The following examples are further illustrative of the present invention and are not intended to limit the scope of the present invention.
Examples 1 to 4
Dissolving azodiisobutyronitrile and 1, 6-hexanediol diacrylate in N-vinyl pyrrolidone, then putting the N-vinyl pyrrolidone in which azodiisobutyronitrile and 1, 6-hexanediol diacrylate are dissolved and chlorinated polyethylene rubber into a reactor, uniformly mixing, introducing nitrogen to remove oxygen, heating to 70 ℃, reacting for 6 hours, taking out a product, soaking and washing in deionized water for 120 hours, and drying in vacuum at 60 ℃ to constant weight to obtain the polyvinylpyrrolidone/chlorinated polyethylene water-absorbing expansion rubber.
The polyvinyl pyrrolidone/chlorinated polyethylene water swellable rubbers of examples 1 to 4 were prepared in the same manner, but in which the weight ratio (or molar ratio) of azobisisobutyronitrile, 1, 6-hexanediol diacrylate and chlorinated polyethylene rubber was different. The composition ratios of examples 1 to 4 are shown in Table 1.
The hardness of the sample after water absorption and expansion is tested according to the standard GB/T531-2008, and the tensile strength and the elongation at break of the sample after water absorption and expansion are tested according to the standard GB/T528-2009.
Testing water absorption expansion ratio: the size of the sample is 20mm multiplied by 2mm, the original weight of the sample is weighed, the sample is soaked in deionized water, the sample is taken out and weighed at different soaking time, the surface moisture is quickly absorbed by filter paper during each weighing, the operation is repeated until the weight of the weighed soaked sample is not changed, namely the sample reaches the water absorption swelling balance. The calculation formula of the water absorption expansion ratio is as follows:
water absorption expansion ratio (water absorption balance weight-sample original weight)/sample original weight × 100%
Testing the mass loss rate: the size of the sample is 20mm multiplied by 2mm, the original weight of the sample is weighed, the sample is soaked in deionized water for 120 hours, water is changed every 24 hours, then the sample is taken out and placed in a vacuum drying oven at 60 ℃ to be dried to constant weight, and the calculation formula of the mass loss rate of the sample is as follows:
the mass loss rate (original weight of sample-weight of sample after water absorption and drying)/original weight of sample x 100%
The test results are shown in Table 1.
TABLE 1
Claims (4)
1. A preparation method of polyvinyl pyrrolidone/chlorinated polyethylene water-swelling rubber is characterized by comprising the following steps: dissolving azodiisobutyronitrile and 1, 6-hexanediol diacrylate in N-vinyl pyrrolidone, then putting the N-vinyl pyrrolidone in which azodiisobutyronitrile and 1, 6-hexanediol diacrylate are dissolved and chlorinated polyethylene rubber into a reactor, uniformly mixing, introducing nitrogen to remove oxygen, heating to 70 ℃, reacting for 6 hours, taking out a product after the reaction is finished, soaking and washing the product in deionized water for 120 hours, and drying in vacuum at 60 ℃ to constant weight to obtain the polyvinyl pyrrolidone/chlorinated polyethylene water-absorbing expansion rubber.
2. The method for preparing polyvinylpyrrolidone/chlorinated polyethylene water-swellable rubber according to claim 1, characterized in that: the mass ratio of the N-vinyl pyrrolidone to the chlorinated polyethylene rubber is 1: 4-1: 2.
3. The method for preparing polyvinylpyrrolidone/chlorinated polyethylene water-swellable rubber according to claim 1, characterized in that: the azodiisobutyronitrile accounts for 0.5mol percent of the N-vinyl pyrrolidone.
4. The method for preparing polyvinylpyrrolidone/chlorinated polyethylene water-swellable rubber according to claim 1, characterized in that: the 1, 6-hexanediol diacrylate accounts for 1-3 mol% of the N-vinyl pyrrolidone.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998040425A1 (en) * | 1997-03-07 | 1998-09-17 | Sulc Jiri | Composite water swellable elastomers and method of preparation thereof |
| CN1450105A (en) * | 2003-04-29 | 2003-10-22 | 上海交通大学 | High-performace water-absorbing expansion rubber and process for preparing same |
| CN104086699A (en) * | 2014-07-04 | 2014-10-08 | 青岛科技大学 | Non-blending type high-stability polyacrylate water absorption swelling rubber and preparation method thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998040425A1 (en) * | 1997-03-07 | 1998-09-17 | Sulc Jiri | Composite water swellable elastomers and method of preparation thereof |
| CN1450105A (en) * | 2003-04-29 | 2003-10-22 | 上海交通大学 | High-performace water-absorbing expansion rubber and process for preparing same |
| CN104086699A (en) * | 2014-07-04 | 2014-10-08 | 青岛科技大学 | Non-blending type high-stability polyacrylate water absorption swelling rubber and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| Synthesis and Swelling Properties of Grafting-Type and Crosslinking-Type Water-Swellable Elastomers;Peixin He;《Journal of applied polymer Science》;20071231;第104卷;2637–2642 * |
| 原位合成丙烯酸盐改性氯化聚乙烯制备吸水膨胀橡胶的研究;任文坛;《橡胶化工》;20051231;第52卷;69-74 * |
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