CN110396206B - Preparation method of hydrogenated nitrile rubber latex - Google Patents
Preparation method of hydrogenated nitrile rubber latex Download PDFInfo
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- CN110396206B CN110396206B CN201910779053.0A CN201910779053A CN110396206B CN 110396206 B CN110396206 B CN 110396206B CN 201910779053 A CN201910779053 A CN 201910779053A CN 110396206 B CN110396206 B CN 110396206B
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/07—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from polymer solutions
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Abstract
The invention discloses a preparation method of hydrogenated nitrile rubber latex. The method comprises the following steps: (1) mixing solid hydrogenated nitrile-butadiene rubber and an organic solvent to obtain a hydrogenated nitrile-butadiene rubber solution; (2) mixing an anionic emulsifier, a nonionic emulsifier and water to obtain an emulsifier aqueous solution; (3) shearing and emulsifying a pre-emulsified mixed solution formed by mixing the hydrogenated nitrile-butadiene rubber solution obtained in the step (1) and the emulsifier aqueous solution obtained in the step (2) to form an emulsion; (4) carrying out reduced pressure distillation on the emulsion obtained in the step (3) to obtain hydrogenated nitrile-butadiene rubber latex; the organic solvent is selected from chloroform, butanone, chlorobenzene or tetrahydrofuran; the mass ratio of the anionic emulsifier to the nonionic emulsifier is 1: 1-1: 2.
Description
Technical Field
The invention relates to the field of organic polymers, in particular to a preparation method of hydrogenated nitrile rubber latex.
Background
Hydrogenated nitrile rubber latex refers to a stable colloidal dispersion of particles of hydrogenated nitrile rubber dispersed in an aqueous medium. CN101704909/CN101367887 has disclosed a process for preparing hydrogenated nitrile latex by direct hydrogenation using nitrile rubber (NBR) latex. The hydrogenated nitrile latex obtained by the method has low hydrogenation degree which can only reach 85 percent at most, and gel is generated in the hydrogenation process. In addition, in recent years, foreign companies such as Good Yeast, Oline, JSR and the like have carried out some work on the NBR latex direct hydrogenation technology on the basis of Wilkinson catalytic hydrogenation and hydrazine hydrate hydrogenation NBR latex methods, but no breakthrough progress exists.
Therefore, the adoption of the inverse emulsion method of the hydrogenated nitrile rubber solution is the only effective and feasible technical way for preparing the hydrogenated nitrile rubber latex at present. The method comprises the steps of firstly dissolving solid hydrogenated nitrile rubber in an organic solvent, then mixing an emulsifier, water and a rubber solution, emulsifying to obtain an oil-in-water emulsion, removing the organic solvent through reduced pressure distillation to obtain a dilute latex, and further concentrating to obtain the ideal hydrogenated nitrile rubber latex.
When the hydrogenated nitrile rubber latex is produced by emulsification in a reverse phase method, the selection of the emulsifier is very important. The choice of emulsifier influences not only the process for the production of the latex but also the properties of the latex. There is therefore a great need in the art to find suitable emulsifiers which improve the properties of the latex and corresponding processes for the production of hydrogenated nitrile rubber latices.
Disclosure of Invention
The invention aims to provide a preparation method of hydrogenated nitrile rubber latex capable of effectively improving the performance of the latex.
In a first aspect of the present invention, there is provided a process for the preparation of a hydrogenated nitrile rubber latex, said process comprising the steps of:
(1) mixing solid hydrogenated nitrile-butadiene rubber and an organic solvent to obtain a hydrogenated nitrile-butadiene rubber solution;
(2) mixing an anionic emulsifier, a nonionic emulsifier and water to obtain an emulsifier aqueous solution;
(3) shearing and emulsifying a pre-emulsified mixed solution formed by mixing the hydrogenated nitrile-butadiene rubber solution obtained in the step (1) and the emulsifier aqueous solution obtained in the step (2) to form an emulsion; and
(4) carrying out reduced pressure distillation on the emulsion obtained in the step (3) to obtain hydrogenated nitrile-butadiene rubber latex;
the organic solvent is selected from chloroform, butanone, chlorobenzene or tetrahydrofuran;
the mass ratio of the anionic emulsifier to the nonionic emulsifier is 1: 1-1: 2.
in another preferred embodiment, the mass ratio of the anionic emulsifier to the nonionic emulsifier is 1: 1-1: 1.5.
in another preferred embodiment, the anionic emulsifier is selected from potassium disproportionate abietate or sodium disproportionate abietate; the non-ionic emulsifier is sorbitan monooleate (Span-80).
In another preferred example, the aqueous emulsifier solution obtained in the step (2) further contains a co-emulsifier; the coemulsifier is 2-phenyl-2-propanol.
In another preferred embodiment, the co-emulsifier is used in an amount of 1-10 wt%, based on the total weight of the emulsifiers used.
In another preferred embodiment, the hydrogenated nitrile rubber solution obtained in step (1) and the aqueous emulsifier solution obtained in step (2) are mixed in a ratio of 2.5: 1.0-1.0: 1.0 mass ratio; more preferred ratios are 2.0: 1.0-1.0: 1.0.
in another preferred example, step (3) is shear emulsification using a high-speed shear emulsifier.
In another preferred example, the reduced pressure distillation is carried out under conditions of 50 to 80 ℃ and negative pressure of-0.01 to-0.1 MPa.
In another preferred embodiment, the saturation degree of the hydrogenated nitrile rubber in the step (1) is 85-99%, and the Mooney viscosity ML is(1+4)20-30 ℃ at 100 ℃ and 28-43% of acrylonitrile.
In a second aspect of the present invention, there is provided a hydrogenated nitrile rubber latex obtained by the above-mentioned preparation method provided by the present invention, having a solid content of 30 to 35% and a latex particle size distribution of 0.3 to 0.8. mu.m.
In another preferred embodiment, the saturation degree of the hydrogenated nitrile rubber latex is 85-99%.
In a third aspect of the invention there is provided the use of a hydrogenated nitrile rubber latex as described above in accordance with the invention.
Accordingly, the invention provides a method for producing hydrogenated nitrile rubber latex, and various properties of the obtained latex are improved.
Detailed Description
The inventor prepares the hydrogenated nitrile rubber latex with different acrylonitrile contents and saturation, high solid content and storage stability by adopting a reverse phase emulsification method after dissolving the solid hydrogenated nitrile rubber through an emulsifier compounding test and an emulsification process improvement adjustment. On the basis of this, the present invention has been completed.
Specifically, the invention provides a preparation method of hydrogenated nitrile rubber latex, which comprises the following steps:
firstly, respectively obtaining a hydrogenated nitrile-butadiene rubber solution and an emulsifier aqueous solution;
secondly, mixing the hydrogenated nitrile-butadiene rubber solution and an emulsifier aqueous solution to form a uniformly dispersed pre-emulsified mixed solution;
thirdly, the pre-emulsified mixed solution becomes emulsion with good dispersibility;
and fourthly, distilling the emulsion with good dispersibility under reduced pressure to remove the organic solvent, thereby obtaining the hydrogenated nitrile rubber latex.
The preparation method comprises the following raw materials: 10-20 parts of solid hydrogenated nitrile rubber, 80-100 parts of organic solvent, 0.08-2.4 parts of compound emulsifier and 40-80 parts of water.
In one embodiment of the present invention, the raw materials may further comprise 1-10 wt% of a co-emulsifier, based on the total weight of the compound emulsifier in the raw materials.
The water in the feedstock may be conventional in the art, and in one embodiment deionized water may be used.
In the first step, a hydrogenated nitrile rubber solution can be obtained by mixing solid hydrogenated nitrile rubber with an organic solvent; the organic solvent is selected from chloroform, butanone, chlorobenzene or tetrahydrofuran; chloroform is preferred.
In one embodiment of the present invention, the Mooney viscosity ML is used at a saturation of 95 to 99%(1+4)20-30 ℃ and 28-43% acrylonitrile content.
In the first step, the emulsifier aqueous solution can be obtained by dissolving the compound emulsifier in water; the compound emulsifier consists of an anionic emulsifier and a nonionic emulsifier, wherein the mass ratio of the anionic emulsifier to the nonionic emulsifier is 1: 1 to 2.
In one embodiment of the present invention, the anionic emulsifier includes, but is not limited to, potassium disproportionate rosinate, sodium disproportionate rosinate; the nonionic emulsifier includes, but is not limited to, sorbitan monooleate (Span-80).
In one embodiment of the present invention, the aqueous emulsifier solution may further contain a co-emulsifier; the coemulsifier is 2-phenyl-2-propanol.
In one embodiment of the present invention, the pH of the emulsifier aqueous solution may be adjusted to 9-13 using an alkaline solution; the alkaline solution includes, but is not limited to, sodium hydroxide, potassium hydroxide.
In the second step, the mixing ratio of the hydrogenated nitrile rubber solution to the emulsifier aqueous solution is 2.5-1.0: 1.0; in one embodiment, the hydrogenated nitrile rubber solution and the aqueous emulsifier solution are stirred mechanically in a stirrer to form a pre-emulsified mixture which is uniformly dispersed.
In an embodiment of the present invention, in the third step, a high-speed shearing emulsifying machine is used to perform shearing emulsification so that the pre-emulsified mixed solution becomes an emulsion with good dispersibility; shear emulsification conditions that may be employed include, but are not limited to, shear emulsification at a linear velocity of 27m/s for 5 to 15 minutes.
In one embodiment of the present invention, the vacuum distillation conditions in the fourth step may be 50 to 80 ℃ and a negative pressure of-0.01 to-0.1 MPa.
According to the preparation method, the hydrogenated nitrile rubber latex with the solid content of 30-35% and the milk particle size distribution of 0.3-0.8 mu m can be obtained; the saturation degree of the hydrogenated nitrile rubber latex is 85-99%.
Compared with the general latex such as NBR latex, the hydrogenated nitrile-butadiene rubber latex prepared by the invention has excellent performance without ethical ratio, and is expected to be used for manufacturing latex products, adhesives and coatings with high performance such as chemical resistance, high temperature resistance, ozone resistance, wear resistance, high strength and the like and for treating the surface of fabrics of rubber composite materials.
The features mentioned above with reference to the invention, or the features mentioned with reference to the embodiments, can be combined arbitrarily. All the features disclosed in this specification may be combined in any combination, and each feature disclosed in this specification may be replaced by alternative features serving the same, equivalent or similar purpose. Thus, unless expressly stated otherwise, the features disclosed are merely generic examples of equivalent or similar features.
The main advantages of the invention are: according to the preparation method of the hydrogenated nitrile rubber latex, the hydrogenated nitrile rubber latex with different acrylonitrile contents and saturation, high solid content and storage stability is prepared by dissolving solid hydrogenated nitrile rubber and adopting a reverse phase emulsification method through an emulsifier compounding test and an emulsification process improvement adjustment.
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Experimental procedures without specific conditions noted in the following examples, generally according to conventional conditions or according to conditions recommended by the manufacturers. All percentages, ratios, proportions, or parts are by weight unless otherwise specified. The units in weight volume percent in the present invention are well known to those skilled in the art and refer to, for example, the weight (g) of solute in 100 ml of solution. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present invention. The preferred embodiments and materials described herein are intended to be exemplary only.
The effect test methods of the following examples and comparative examples visually observe the latex stabilization time based on no significant two-phase delamination; measuring a latex sample according to SH/T1154-2011 and calculating the solid content of the latex sample by a gravimetric method; diluting the latex with deionized water, placing the latex into a sample cell after the latex is transparent and clear, and measuring the particle size and distribution of the latex by using a laser light scattering instrument; and measuring and calculating the distillation demulsification rate of the latex sample by adopting a mass difference method.
Example 1
Raw materials:
the solid hydrogenated nitrile rubber is hydrogenated nitrile rubber ZN35253 produced by Zhannan science and technology (Shanghai) Co., Ltd., the saturation is 90%, the acrylonitrile content is 34%, and the Mooney viscosity ML is(1+4)30 at 100 DEG C
Anionic emulsifiers: disproportionated potassium abietate
Non-ionic emulsifier: span-80
Organic solvent: chloroform
Auxiliary emulsifier: 2-phenyl-2-propanol
The process comprises the following steps:
dissolving 15g of solid hydrogenated nitrile rubber in 85g of organic solvent to prepare 15% rubber solution; adding 0.3g of anionic emulsifier and 0.45g of nonionic emulsifier into a co-emulsifier accounting for 5% of the mass of the main emulsifier, adjusting the pH value to 9-13 by using a 10% potassium hydroxide solution to prepare an emulsifier aqueous solution, and mixing the rubber solution and the emulsifier aqueous solution in a ratio of 2: pouring 1 part by weight of the mixture into a stirrer, mixing and performing strong mechanical stirring to form a macroscopic homogeneous pre-emulsified mixed solution; emulsifying the pre-emulsified emulsion for 10 minutes by using a high-speed shearing emulsifying machine at a linear speed of 27 m/s; and (3) distilling the emulsified emulsion under reduced pressure of-0.01 to-0.1 MPa at 63-73 ℃ until the solvent is completely removed to obtain the hydrogenated nitrile-butadiene rubber latex with the solid content of 30%, the saturation of 90% and the particle size distribution of 0.3-0.8 um.
Example 2
Raw materials:
solid hydrogenated butylThe nitrile rubber is hydrogenated nitrile rubber ZN35052 produced by Zhannan science and technology (Shanghai) Co., Ltd., saturation degree is 99%, acrylonitrile content is 34%, and Mooney viscosity ML(1+4)20 at 100 DEG C
Anionic emulsifiers: disproportionated sodium abietate
Non-ionic emulsifier: span-80
Organic solvent: chloroform
Auxiliary emulsifier: 2-phenyl-2-propanol
The process comprises the following steps:
firstly, 20g of solid hydrogenated nitrile rubber is dissolved in 80g of organic solvent by weight to prepare 20 wt% of rubber solution; adding 0.48g of anionic emulsifier and 0.6g of nonionic emulsifier into a co-emulsifier accounting for 5% of the mass of the main emulsifier, adjusting the pH value to 9-13 by using a 10% potassium hydroxide solution to prepare an emulsifier aqueous solution, and mixing the rubber solution and the emulsifier aqueous solution in a ratio of 2: pouring 1 part by weight of the mixture into a stirrer, mixing and performing strong mechanical stirring to form a macroscopic homogeneous pre-emulsified mixed solution; emulsifying the pre-emulsified emulsion for 10 minutes by using a high-speed shearing emulsifying machine at a linear speed of 27 m/s; and (3) carrying out reduced pressure distillation on the emulsified emulsion at 63-73 ℃ under the negative pressure of-0.01-0.1 MPa, removing the solvent to obtain hydrogenated butyronitrile latex with the solid content of 35%, wherein the saturation is 99%, and the particle size distribution of the hydrogenated butyronitrile latex is 0.3-0.8 um.
Example 3
Raw materials:
the solid hydrogenated nitrile rubber is hydrogenated nitrile rubber ZN43153 produced by Zhannan science and technology (Shanghai) Co., Ltd., and has a saturation of 95%, an acrylonitrile content of 42%, and a Mooney viscosity ML(1+4)30 at 100 DEG C
Anionic emulsifiers: disproportionated potassium abietate
Non-ionic emulsifier: span-80
Organic solvent: chloroform
Auxiliary emulsifier: 2-phenyl-2-propanol
The process comprises the following steps:
firstly, dissolving 15g of solid hydrogenated nitrile rubber in 85g of organic solvent by weight to prepare 15 wt% of rubber solution; adding 0.3g of anionic emulsifier and 0.0.53g of nonionic emulsifier into a co-emulsifier accounting for 5% of the mass of the main emulsifier, adjusting the pH value to 9-13 by using 10% potassium hydroxide solution to prepare an emulsifier aqueous solution, mixing the rubber solution and the emulsifier aqueous solution according to the weight ratio of 1.75: pouring 1 part by weight of the mixture into a stirrer, mixing and performing strong mechanical stirring to form a macroscopic homogeneous pre-emulsified mixed solution; emulsifying the pre-emulsified emulsion for 10 minutes by using a high-speed shearing emulsifying machine at a linear speed of 27 m/s; and (3) carrying out reduced pressure distillation on the emulsified emulsion at 63-73 ℃ under the negative pressure of-0.01-0.1 MPa, and removing the solvent to obtain hydrogenated butyronitrile latex with the solid content of 28%, wherein the saturation is 95%, and the particle size distribution of the hydrogenated butyronitrile latex is 0.3-0.8 um.
Comparative example 1
Raw materials:
same as in example 1
The process comprises the following steps:
essentially the same as in example 1, except that the emulsified emulsion was rotary evaporated under reduced pressure at 60 ℃ to remove the solvent, and the rubber precipitated during the rotary evaporation.
Comparative example 2
Raw materials:
same as in example 1
The process comprises the following steps:
firstly, dissolving 15 parts by weight of solid hydrogenated nitrile rubber in 85 parts by weight of organic solvent to prepare a rubber solution; mixing 0.5 weight part of anionic emulsifier and 0.25 weight part of nonionic emulsifier, adding a co-emulsifier accounting for 5% of the mass of the main emulsifier, adjusting the pH value to 9-13 by using a 10% potassium hydroxide solution to prepare an emulsifier aqueous solution, mixing the rubber solution and the emulsifier aqueous solution according to the weight ratio of 2: pouring 1 part by weight of the mixture into a stirrer, mixing and performing strong mechanical stirring to form a macroscopic homogeneous pre-emulsified mixed solution; emulsifying the pre-emulsified emulsion for 10 minutes by using a high-speed shearing emulsifying machine at a linear speed of 27 m/s; and (3) distilling the emulsified emulsion under reduced pressure of-0.01 to-0.1 MPa at 63-73 ℃ until all the solvent is removed to obtain the hydrogenated butyronitrile emulsion, wherein the emulsion has poor stability and can be immediately layered.
Comparative example 3
Raw materials:
essentially as in example 1, the emulsifier is polyethylene glycol
The process comprises the following steps:
firstly, dissolving 15 parts by weight of solid hydrogenated nitrile rubber in 85 parts by weight of organic solvent to prepare a rubber solution with the mass fraction of 15%; mixing 0.25 weight part of anionic emulsifier and 0.5 weight part of nonionic emulsifier, adding a co-emulsifier accounting for 5% of the mass of the main emulsifier, and adjusting the pH value to 9-13 by using potassium hydroxide to prepare an emulsifier aqueous solution; mixing the rubber solution and an emulsifier aqueous solution in a ratio of 2.0: pouring 1.0 part by weight of the mixture into a stirrer, mixing and carrying out strong mechanical stirring to form a macroscopic homogeneous pre-emulsified mixed solution; emulsifying the pre-emulsified emulsion for 5-15 minutes by using a high-speed shearing emulsifying machine at a linear speed of 27 m/s; and (3) carrying out reduced pressure low temperature distillation on the emulsified emulsion at 50-80 ℃, wherein the negative pressure is-0.01-0.1 MPa, until the solvent is completely removed and water is evaporated, thus obtaining the hydrogenated butyronitrile latex with the solid content of 30%.
Comparative example 4
Raw materials:
essentially the same as in example 1, except that the organic solvent used was acetone
The process comprises the following steps:
firstly, dissolving 15 parts by weight of solid hydrogenated nitrile rubber in 85 parts by weight of organic solvent to prepare a rubber solution with the mass fraction of 15%; adding 0.3g of anionic emulsifier and 0.45g of nonionic emulsifier into a co-emulsifier accounting for 5% of the mass of the main emulsifier, adjusting the pH value to 9-13 by using a 10% potassium hydroxide solution to prepare an emulsifier aqueous solution, and mixing the rubber solution and the emulsifier aqueous solution in a ratio of 2: pouring 1 part by weight of the mixture into a stirrer, and continuously precipitating the rubber as a solid phase under the strong mechanical stirring along with the addition of the rubber solution, so that a macroscopic homogeneous pre-emulsified mixed solution cannot be formed.
Emulsion results and stability comparisons of examples and comparative examples
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the scope of the invention, which is defined by the claims appended hereto, and any other technical entity or method that is encompassed by the claims as broadly defined herein, or equivalent variations thereof, is contemplated as being encompassed by the claims.
Claims (10)
1. A process for the preparation of a hydrogenated nitrile rubber latex, said process comprising the steps of:
(1) mixing solid hydrogenated nitrile-butadiene rubber and an organic solvent to obtain a hydrogenated nitrile-butadiene rubber solution;
(2) mixing an anionic emulsifier, a nonionic emulsifier and water to obtain an emulsifier aqueous solution;
(3) shearing and emulsifying a pre-emulsified mixed solution formed by mixing the hydrogenated nitrile-butadiene rubber solution obtained in the step (1) and the emulsifier aqueous solution obtained in the step (2) to form an emulsion;
(4) carrying out reduced pressure distillation on the emulsion obtained in the step (3) to obtain hydrogenated nitrile-butadiene rubber latex;
the organic solvent is selected from chloroform, butanone, chlorobenzene or tetrahydrofuran;
the mass ratio of the anionic emulsifier to the nonionic emulsifier is 1: 1-1: 2;
the anionic emulsifier is selected from potassium disproportionated rosin or sodium disproportionated rosin; the nonionic emulsifier is sorbitan monooleate; the emulsifier aqueous solution obtained in the step (2) also contains a co-emulsifier; the auxiliary emulsifier is 2-phenyl-2-propanol;
the reduced pressure distillation condition is 50-80 ℃ and negative pressure of-0.01 to-0.1 MPa.
2. The method according to claim 1, wherein the mass ratio of the anionic emulsifier to the nonionic emulsifier is 1: 1-1: 1.5.
3. the method of claim 1, wherein the co-emulsifier is used in an amount of 1 to 10 wt% based on the total weight of the emulsifier used.
4. The process according to claim 1, wherein the hydrogenated nitrile rubber solution obtained in step (1) and the aqueous emulsifier solution obtained in step (2) are mixed in a ratio of 2.5: 1.0-1.0: 1.0 mass ratio.
5. The process according to claim 1, wherein the ratio of the hydrogenated nitrile rubber solution obtained in step (1) to the aqueous emulsifier solution obtained in step (2) is from 2.0: 1.0-1.0: 1.0 mass ratio.
6. The method of claim 1, wherein step (3) is shear emulsification using a high shear emulsifier.
7. The process according to any one of claims 1 to 6, wherein the hydrogenated nitrile rubber in step (1) has a saturation of 85 to 99% and a Mooney viscosity ML(1+4)20-30 ℃ at 100 ℃ and 28-43% of acrylonitrile.
8. A hydrogenated nitrile rubber latex obtained by the production process according to any one of claims 1 to 7, having a solid content of 30 to 35% and a particle size distribution of 0.3 to 0.8. mu.m.
9. The hydrogenated nitrile rubber latex according to claim 8, wherein the saturation of the hydrogenated nitrile rubber latex is 90 to 99%.
10. Use of the hydrogenated nitrile rubber latex according to claim 8 or 9.
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| CA2209442A1 (en) * | 1996-09-16 | 1998-03-16 | The Goodyear Tire & Rubber Company | Hydrogenated nitrile rubber latex composition |
| DE102005059625A1 (en) * | 2005-12-14 | 2007-06-21 | Lanxess Deutschland Gmbh | Microgel-containing vulcanizable composition based on hydrogenated nitrile rubber |
| EP2325237A1 (en) * | 2009-11-19 | 2011-05-25 | LANXESS Deutschland GmbH | Stable fine-particle suspensions of functionalised, wholly or partially hydrated nitrile rubbers |
| WO2019093248A1 (en) * | 2017-11-10 | 2019-05-16 | 日本ゼオン株式会社 | Method for manufacturing hydrogenated nitrile rubber |
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