CN111548502A - Preparation method of modified synthetic rubber through chain extension reaction - Google Patents
Preparation method of modified synthetic rubber through chain extension reaction Download PDFInfo
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- CN111548502A CN111548502A CN202010493218.0A CN202010493218A CN111548502A CN 111548502 A CN111548502 A CN 111548502A CN 202010493218 A CN202010493218 A CN 202010493218A CN 111548502 A CN111548502 A CN 111548502A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2380/00—Tyres
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a preparation method of a modified synthetic rubber through chain extension reaction, which comprises the following steps: firstly, dehydrating dihydric alcohol or a dihydric alcohol polymer, then dripping the dihydric alcohol or the dihydric alcohol polymer into diisocyanate in a nitrogen atmosphere, and when the content of isocyanic acid radical reaches a certain requirement, obtaining an isocyanate-terminated polyurethane prepolymer; adding a sealing agent and a catalyst into the generated isocyanate-terminated polyurethane prepolymer for end group sealing, and stopping the reaction when the content of the isocyanate group is lower than 0.01% to prepare a rubber chain extender; adding the prepared rubber chain extender into the synthetic rubber at the synthetic rubber mixing stage, carrying out deblocking reaction on the chain extender in the rubber material vulcanization process, carrying out chain extension reaction with the terminal group of the synthetic rubber molecular chain, and finishing the modification of the rubber in the rubber vulcanization molding process to prepare the modified synthetic rubber. The invention solves the balance problem between the hysteresis loss and the wet skid resistance of the rubber material.
Description
Technical Field
The invention relates to a preparation method of synthetic rubber, in particular to a preparation method of synthetic rubber modified through chain extension reaction.
Background
Rubber has strong viscoelastic properties, and hysteresis loss of rubber, which is a main raw material of a tire, greatly affects the rolling resistance of the tire. In general, since the rolling resistance and wear resistance of a tire are reduced and the wet skid resistance of the tire is greatly affected, it is necessary to reduce the rolling resistance and wear resistance and wet skid resistance of the tire while ensuring the safety of the use of the tire.
The microstructure is a key factor for determining the macroscopic performance of the polymer, so the microstructure of the rubber needs to be designed, and the problem of balance between the hysteresis loss and the wet skid resistance of the rubber material is solved. Therefore, researchers at home and abroad research and develop novel polymers with excellent performance and modify the existing rubber materials so as to meet the mutual balance among rolling resistance, wet-skid resistance and wear resistance of tires. In view of the problems mainly existing in the use of tire materials, despite much work, the research and development and partial industrialization of products are limited to rubber varieties and reinforcing materials.
Disclosure of Invention
In order to solve the balance problem between the hysteresis loss and the wet skid resistance of rubber materials, the invention provides a preparation method of a synthetic rubber modified through a chain extension reaction, which reduces the kinetic energy loss of the tail end of a free chain, reduces the hysteresis loss of a polymer and improves the wear resistance of a rubber material by chemically modifying the synthetic rubber through introducing a rubber chain extender.
The technical scheme adopted by the invention for realizing the purpose is as follows:
a preparation method of a synthetic rubber modified by chain extension reaction comprises the following steps:
1) preparing a polyurethane prepolymer, namely dehydrating a small amount of water contained in dihydric alcohol or a dihydric alcohol polymer, dripping the dihydric alcohol or the dihydric alcohol polymer into diisocyanate under the nitrogen atmosphere while stirring, controlling the ratio of isocyanate groups to hydroxyl groups to synthesize the isocyanate-terminated polyurethane prepolymer with the molecular weight M of 500-10000, removing the heat generated by reaction in time, controlling the temperature to be 60-95 ℃, and stirring to react until the content of isocyanate groups meets the requirement, thus obtaining the isocyanate-terminated polyurethane prepolymer; the molar ratio of the diisocyanate to the dihydric alcohol or the dihydric alcohol polymer is (1-2): 1;
2) preparing a chain extender: adding a sealing agent and a catalyst into the isocyanate-terminated polyurethane prepolymer generated in the step 1) to seal the end groups, and stopping the reaction when the content of the isocyanate groups is lower than 0.01% to prepare a rubber chain extender;
3) adding the rubber chain extender prepared in the step 2) into the synthetic rubber in the synthetic rubber mixing stage, mixing uniformly, carrying out deblocking reaction on the chain extender in the rubber material vulcanization process, carrying out chain extension reaction with the terminal group of the synthetic rubber molecular chain, connecting the synthetic rubber chain and the chain extender chain by a polyurethane group, reducing the hysteresis loss of the rubber material, improving the wear resistance of the rubber material, and modifying the rubber in the rubber vulcanization molding process to prepare modified synthetic rubber; the weight parts of the rubber material and the rubber chain extender are as follows: 100 parts of rubber material, and 3-10 parts of chain extender; the deblocking temperature of the rubber chain extender is 130-160 ℃.
When the isocyanate-terminated polyurethane prepolymer is sealed, the performance of a rubber product is required not to be reduced by the sealant, and the deblocking temperature of the rubber chain extender is ensured to be basically consistent with the vulcanization temperature of rubber and slightly higher than the mixing temperature of the rubber by 80-130 ℃, so that the rubber chain extender can be uniformly dispersed in the rubber during rubber mixing and does not react with the terminal group of a rubber molecular chain, otherwise, the Mooney viscosity of the rubber material is improved, and the post-processing performance of the rubber material is influenced. And deblocking is carried out in the vulcanization process, so that the chain extension reaction and the vulcanization reaction are carried out synchronously, and the performance of the rubber material is improved.
Further, the calculation steps for the content of the isocyanate group reaching the required value b are as follows:
a＝n(NCO):n(OH)
M＝[m(NCO)+m(OH)]/[n(NCO)-n(OH)]
a molar ratio of diisocyanate to diol (greater than 1)
N (NCO) amount of diisocyanate (mol)
n (OH) amount of substance of glycol (mol)
M: molecular weight of prepolymer
mass (g) of m (NCO) diisocyanate
m (OH) mass (g) of glycol
b is the content (%) of isocyanate groups.
Preferably, the diol polymer is a low molecular diol, a polyether diol or a polyester diol.
Preferably, the blocking agent and the catalyst are oximes and imidazoles.
The invention mainly adds a chain extender into the synthetic rubber, and utilizes the active group of the chain extender to carry out chain extension reaction with the terminal group of the synthetic rubber, thereby achieving the following purposes: 1) the mass fraction of the bonding rubber is improved, and the energy loss of the motion of the free chain end is reduced; 2) the urethane group with excellent wear resistance is introduced through reaction, so that the wear resistance of the rubber material is greatly improved; 3) the interaction between the polymer and the carbon black can be enhanced, and the dispersibility of the carbon black is improved; 4) a layer of polymer is formed on the surface of the carbon black, so that the carbon black is prevented from aggregating, and the hysteresis loss of the polymer is reduced.
Detailed Description
Example 1
The preparation method of the modified synthetic rubber through the chain extension reaction of the embodiment comprises the following steps:
1) preparing a polyurethane prepolymer, namely dehydrating a small amount of water contained in dihydric alcohol or a dihydric alcohol polymer, dropwise adding the dihydric alcohol or the dihydric alcohol polymer into diisocyanate under the nitrogen atmosphere while stirring, controlling the ratio of isocyanate groups to hydroxyl groups to synthesize an isocyanate-terminated polyurethane prepolymer with the molecular weight M of 1000, removing heat generated by reaction in time, controlling the temperature to be 60 ℃, and stirring to react until the content of isocyanate groups meets the requirement, thus obtaining the isocyanate-terminated polyurethane prepolymer; the molar ratio of the diisocyanate to the diol or the diol polymer is 2: 1;
2) preparing a chain extender: adding a sealing agent and a catalyst into the isocyanate-terminated polyurethane prepolymer generated in the step 1) to seal the end groups, and stopping the reaction when the content of the isocyanate groups is lower than 0.01% to prepare a rubber chain extender;
3) adding the rubber chain extender prepared in the step 2) into the synthetic rubber in the synthetic rubber mixing stage, mixing uniformly, carrying out deblocking reaction on the chain extender in the rubber material vulcanization process, carrying out chain extension reaction with the terminal group of the synthetic rubber molecular chain, connecting the synthetic rubber chain and the chain extender chain by a polyurethane group, reducing the hysteresis loss of the rubber material, improving the wear resistance of the rubber material, and modifying the rubber in the rubber vulcanization molding process to prepare modified synthetic rubber; the weight parts of the rubber material and the rubber chain extender are as follows: 100 parts of rubber material, and 3 parts of chain extender; the deblocking temperature of the rubber chain extender is 130 ℃.
When the isocyanate-terminated polyurethane prepolymer is sealed, the performance of a rubber product is required not to be reduced by the sealant, and the deblocking temperature of the rubber chain extender is ensured to be basically consistent with the vulcanization temperature of rubber and slightly higher than the rubber mixing temperature by 80 ℃, so that the rubber chain extender can be uniformly dispersed in the rubber mixing process and does not react with the terminal group of the rubber molecular chain, otherwise, the Mooney viscosity of the rubber material is improved, and the post-processing performance of the rubber material is influenced. And deblocking is carried out in the vulcanization process, so that the chain extension reaction and the vulcanization reaction are carried out synchronously, and the performance of the rubber material is improved.
Further, the calculation steps for the content of the isocyanate group reaching the required value b are as follows:
a＝n(NCO):n(OH)
M＝[m(NCO)+m(OH)]/[n(NCO)-n(OH)]
a molar ratio of diisocyanate to diol (greater than 1)
N (NCO) amount of diisocyanate (mol)
n (OH) amount of substance of glycol (mol)
M: molecular weight of prepolymer
mass (g) of m (NCO) diisocyanate
m (OH) mass (g) of glycol
b is the content (%) of isocyanate groups.
Preferably, the diol polymer is an oligomer diol, a polyether diol or a polyester diol.
Preferably, the blocking agent and the catalyst are oximes and imidazoles.
Example 2
The preparation method of the modified synthetic rubber through the chain extension reaction of the embodiment comprises the following steps:
1) preparing a polyurethane prepolymer, namely dehydrating a small amount of water contained in dihydric alcohol or a dihydric alcohol polymer, dropwise adding the dihydric alcohol or the dihydric alcohol polymer into diisocyanate under the nitrogen atmosphere while stirring, controlling the ratio of isocyanate groups to hydroxyl groups to synthesize an isocyanate-terminated polyurethane prepolymer with the molecular weight M of 5000, removing heat generated by reaction in time, controlling the temperature to be 75 ℃, and stirring to react until the content of isocyanate groups meets the requirement, thus obtaining the isocyanate-terminated polyurethane prepolymer; the molar ratio of the diisocyanate to the diol or the diol polymer is 1.5: 1;
2) preparing a chain extender: adding a sealing agent and a catalyst into the isocyanate-terminated polyurethane prepolymer generated in the step 1) to seal the end groups, and stopping the reaction when the content of the isocyanate groups is lower than 0.01% to prepare a rubber chain extender;
3) adding the rubber chain extender prepared in the step 2) into the synthetic rubber in the synthetic rubber mixing stage, mixing uniformly, carrying out deblocking reaction on the chain extender in the rubber material vulcanization process, carrying out chain extension reaction with the terminal group of the synthetic rubber molecular chain, connecting the synthetic rubber chain and the chain extender chain by a polyurethane group, reducing the hysteresis loss of the rubber material, improving the wear resistance of the rubber material, and modifying the rubber in the rubber vulcanization molding process to prepare modified synthetic rubber; the weight parts of the rubber material and the rubber chain extender are as follows: 100 parts of rubber material, and 7 parts of chain extender; the deblocking temperature of the rubber chain extender is 150 ℃.
When the isocyanate-terminated polyurethane prepolymer is sealed, the performance of a rubber product is required not to be reduced by the sealant, and the deblocking temperature of the rubber chain extender is ensured to be basically consistent with the vulcanization temperature of rubber and slightly higher than the mixing temperature of the rubber by 110 ℃, so that the rubber chain extender can be uniformly dispersed in the rubber during rubber mixing and does not react with the terminal group of a rubber molecular chain, otherwise, the Mooney viscosity of the rubber material is improved, and the post-processing performance of the rubber material is influenced. And deblocking is carried out in the vulcanization process, so that the chain extension reaction and the vulcanization reaction are carried out synchronously, and the performance of the rubber material is improved.
Further, the calculation steps for the content of the isocyanate group reaching the required value b are as follows:
a＝n(NCO):n(OH)
M＝[m(NCO)+m(OH)]/[n(NCO)-n(OH)]
a molar ratio of diisocyanate to diol (greater than 1)
N (NCO) amount of diisocyanate (mol)
n (OH) amount of substance of glycol (mol)
M: molecular weight of prepolymer
mass (g) of m (NCO) diisocyanate
m (OH) mass (g) of glycol
b is the content (%) of isocyanate groups.
Preferably, the diol polymer is an oligomer diol, a polyether diol or a polyester diol.
Preferably, the blocking agent and the catalyst are oximes and imidazoles.
Example 3
The preparation method of the modified synthetic rubber through the chain extension reaction of the embodiment comprises the following steps:
1) preparing a polyurethane prepolymer, namely dehydrating a small amount of water contained in dihydric alcohol or a dihydric alcohol polymer, dropwise adding the dihydric alcohol or the dihydric alcohol polymer into diisocyanate under the nitrogen atmosphere while stirring, controlling the ratio of isocyanate groups to hydroxyl groups to synthesize an isocyanate-terminated polyurethane prepolymer with the molecular weight M of 10000, removing heat generated by reaction in time, controlling the temperature to be 95 ℃, and stirring to react until the content of isocyanate groups meets the requirement, thus obtaining the isocyanate-terminated polyurethane prepolymer; the molar ratio of the diisocyanate to the diol or the diol polymer is 1.1: 1;
2) preparing a chain extender: adding a sealing agent and a catalyst into the isocyanate-terminated polyurethane prepolymer generated in the step 1) to seal the end groups, and stopping the reaction when the content of the isocyanate groups is lower than 0.01% to prepare a rubber chain extender;
3) adding the rubber chain extender prepared in the step 2) into the synthetic rubber in the synthetic rubber mixing stage, mixing uniformly, carrying out deblocking reaction on the chain extender in the rubber material vulcanization process, carrying out chain extension reaction with the terminal group of the synthetic rubber molecular chain, connecting the synthetic rubber chain and the chain extender chain by a polyurethane group, reducing the hysteresis loss of the rubber material, improving the wear resistance of the rubber material, and modifying the rubber in the rubber vulcanization molding process to prepare modified synthetic rubber; the weight parts of the rubber material and the rubber chain extender are as follows: 100 parts of rubber material, and 10 parts of chain extender; the deblocking temperature of the rubber chain extender is 160 ℃.
When the isocyanate-terminated polyurethane prepolymer is sealed, the performance of a rubber product is required not to be reduced by the sealant, and the deblocking temperature of the rubber chain extender is ensured to be basically consistent with the vulcanization temperature of rubber and slightly higher than the rubber mixing temperature by 130 ℃, so that the rubber chain extender can be uniformly dispersed in the rubber during rubber mixing and does not react with the terminal group of a rubber molecular chain, otherwise, the Mooney viscosity of the rubber material is improved, and the post-processing performance of the rubber material is influenced. And deblocking is carried out in the vulcanization process, so that the chain extension reaction and the vulcanization reaction are carried out synchronously, and the performance of the rubber material is improved.
Further, the calculation steps for the content of the isocyanate group reaching the required value b are as follows:
a＝n(NCO):n(OH)
M＝[m(NCO)+m(OH)]/[n(NCO)-n(OH)]
a molar ratio of diisocyanate to diol (greater than 1)
N (NCO) amount of diisocyanate (mol)
n (OH) amount of substance of glycol (mol)
M: molecular weight of prepolymer
mass (g) of m (NCO) diisocyanate
m (OH) mass (g) of glycol
b is the content (%) of isocyanate groups.
Preferably, the diol polymer is an oligomer diol, a polyether diol or a polyester diol.
Preferably, the blocking agent and the catalyst are oximes and imidazoles.
Claims (4)
1. A preparation method of a synthetic rubber modified by chain extension reaction is characterized by comprising the following steps:
1) preparing a polyurethane prepolymer, namely dehydrating a small amount of water contained in dihydric alcohol or a dihydric alcohol polymer, dripping the dihydric alcohol or the dihydric alcohol polymer into diisocyanate under the nitrogen atmosphere while stirring, controlling the ratio of isocyanate groups to hydroxyl groups to synthesize the isocyanate-terminated polyurethane prepolymer with the molecular weight M of 500-10000, removing the heat generated by reaction in time, controlling the temperature to be 60-95 ℃, and stirring to react until the content of isocyanate groups meets the requirement, thus obtaining the isocyanate-terminated polyurethane prepolymer; the molar ratio of the diisocyanate to the dihydric alcohol or the dihydric alcohol polymer is (1-2): 1;
2) preparing a chain extender: adding a sealing agent and a catalyst into the isocyanate-terminated polyurethane prepolymer generated in the step 1) to seal the end groups, and stopping the reaction when the content of the isocyanate groups is lower than 0.01% to prepare a rubber chain extender;
3) adding the rubber chain extender prepared in the step 2) into the synthetic rubber at the synthetic rubber mixing stage, mixing uniformly, carrying out deblocking reaction on the chain extender in the rubber material vulcanization process, carrying out chain extension reaction with the terminal group of the synthetic rubber molecular chain, and finishing the modification of the rubber in the rubber vulcanization molding process to prepare modified synthetic rubber; the weight parts of the rubber material and the rubber chain extender are as follows: 100 parts of rubber material, and 3-10 parts of chain extender; the deblocking temperature of the rubber chain extender is 130-160 ℃.
2. The method for preparing the synthetic rubber modified by the chain extension reaction according to claim 1, wherein the calculation step of the content of the isocyanate group reaching the required value b is as follows:
a＝n(NCO):n(OH)
M＝[m(NCO)+m(OH)]/[n(NCO)-n(OH)]
a molar ratio of diisocyanate to diol (greater than 1)
N (NCO) amount of diisocyanate (mol)
n (OH) amount of substance of glycol (mol)
M: molecular weight of prepolymer
mass (g) of m (NCO) diisocyanate
m (OH) mass (g) of glycol
b is the content (%) of isocyanate groups.
3. The method for preparing the synthetic rubber modified by the chain extension reaction according to claim 1 or 2, wherein the diol polymer is a low molecular diol, a polyether diol or a polyester diol.
4. The method for preparing the synthetic rubber modified by the chain extension reaction according to claim 1 or 2, wherein the blocking agent and the catalyst are oximes and imidazoles.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9303914D0 (en) * | 1992-02-28 | 1993-04-14 | Goodyear Tire & Rubber | A method of adhering cured rubber to uncured or cured urethane and the resulting product |
| CN101395195A (en) * | 2006-03-03 | 2009-03-25 | 茵迪斯佩克化学公司 | Resorcinol-blocked isocyanate compositions and their applications |
| CN110317560A (en) * | 2018-03-30 | 2019-10-11 | 住友橡胶工业株式会社 | Organic fiber adhesive composition, the processing method of organic fiber, organic fiber and tire |
-
2020
- 2020-06-03 CN CN202010493218.0A patent/CN111548502A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9303914D0 (en) * | 1992-02-28 | 1993-04-14 | Goodyear Tire & Rubber | A method of adhering cured rubber to uncured or cured urethane and the resulting product |
| CN101395195A (en) * | 2006-03-03 | 2009-03-25 | 茵迪斯佩克化学公司 | Resorcinol-blocked isocyanate compositions and their applications |
| CN110317560A (en) * | 2018-03-30 | 2019-10-11 | 住友橡胶工业株式会社 | Organic fiber adhesive composition, the processing method of organic fiber, organic fiber and tire |
Non-Patent Citations (2)
| Title |
|---|
| LIGANG YIN ET AL.: ""Toughening effects of poly(butylene terephthalate) with blocked isocyanate-functionalized poly(ethylene octene)"", 《POLYMER INTERNATIONAL》 * |
| LOU CH ET AL.: ""Toughening Epoxy Resin with Blocked Isocyanate Containing Soft Chain"", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
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Application publication date: 20200818 |