CN116396605A - New energy automobile tire puncture-preventing disc-covered self-repairing sealing material and preparation method thereof - Google Patents
New energy automobile tire puncture-preventing disc-covered self-repairing sealing material and preparation method thereof Download PDFInfo
- Publication number
- CN116396605A CN116396605A CN202310386169.4A CN202310386169A CN116396605A CN 116396605 A CN116396605 A CN 116396605A CN 202310386169 A CN202310386169 A CN 202310386169A CN 116396605 A CN116396605 A CN 116396605A
- Authority
- CN
- China
- Prior art keywords
- sealing material
- mass ratio
- repairing
- modified polyurethane
- energy automobile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003566 sealing material Substances 0.000 title claims abstract description 93
- 238000002360 preparation method Methods 0.000 title claims abstract description 41
- 229920002635 polyurethane Polymers 0.000 claims abstract description 77
- 239000004814 polyurethane Substances 0.000 claims abstract description 77
- 239000000945 filler Substances 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 150000003568 thioethers Chemical class 0.000 claims abstract description 21
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 239000012295 chemical reaction liquid Substances 0.000 claims description 67
- 238000003756 stirring Methods 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
- 239000000243 solution Substances 0.000 claims description 44
- 238000002156 mixing Methods 0.000 claims description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- 238000001035 drying Methods 0.000 claims description 30
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 28
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 26
- 239000011259 mixed solution Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000005303 weighing Methods 0.000 claims description 19
- 239000008367 deionised water Substances 0.000 claims description 15
- 229910021641 deionized water Inorganic materials 0.000 claims description 15
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 14
- 239000011261 inert gas Substances 0.000 claims description 14
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 238000004321 preservation Methods 0.000 claims description 12
- XOPCHXSYQHXLHJ-UHFFFAOYSA-N 1-(4-aminophenyl)pyrrole-2,5-dione Chemical compound C1=CC(N)=CC=C1N1C(=O)C=CC1=O XOPCHXSYQHXLHJ-UHFFFAOYSA-N 0.000 claims description 11
- DCPSTSVLRXOYGS-UHFFFAOYSA-N 6-amino-1h-pyrimidine-2-thione Chemical compound NC1=CC=NC(S)=N1 DCPSTSVLRXOYGS-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000012265 solid product Substances 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 9
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical group [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 5
- 239000006229 carbon black Substances 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 238000011010 flushing procedure Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000006228 supernatant Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical group [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 3
- 229910021389 graphene Inorganic materials 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- QAWTYRYXDYHQNU-UHFFFAOYSA-N diazathiane Chemical compound NSN QAWTYRYXDYHQNU-UHFFFAOYSA-N 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 239000013049 sediment Substances 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 9
- 230000007547 defect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 125000003636 chemical group Chemical group 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract description 2
- 239000003223 protective agent Substances 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 12
- 239000003292 glue Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 241000872198 Serjania polyphylla Species 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000012650 click reaction Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- -1 polydimethylsiloxane Polymers 0.000 description 2
- WKEMQIMZFDORDJ-UHFFFAOYSA-N 1,1-diaminobutane-1,4-diol Chemical compound NC(N)(O)CCCO WKEMQIMZFDORDJ-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
- C08K3/042—Graphene or derivatives, e.g. graphene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
- C08K7/26—Silicon- containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
- C08K2003/265—Calcium, strontium or barium carbonate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Sealing Material Composition (AREA)
Abstract
The invention relates to the field of new energy automobile tires, in particular to a disk-covered self-repairing sealing material for puncture prevention of a new energy automobile tire and a preparation method thereof. The components of the disc-covered self-repairing sealing material comprise a modified polyurethane sealing material and an active filler, wherein the mass ratio of the modified polyurethane sealing material to the active filler is 8.5-9.3:0.7-1.5; wherein the modified polyurethane sealing material is a product obtained by using a thioether-based compound containing double amino groups to participate in the preparation process of polyurethane. The modified polyurethane sealing material prepared by the invention belongs to a polymer polyurethane variety containing various chemical groups, can be used as a self-repairing sealing material of a new energy automobile tire material, has better cohesiveness with rubber, has stronger high-temperature resistance stability, and can fill the defects of poor repairing effect and short service life of the tire protective agent in the current market.
Description
Technical Field
The invention relates to the field of new energy automobile tires, in particular to a disk-covered self-repairing sealing material for puncture prevention of a new energy automobile tire and a preparation method thereof.
Background
At present, the new energy automobile tire mainly has two types, one is an automobile wheel with an inner tube, the other is an automobile wheel without an inner tube, and the most common requirement is the automobile wheel without the inner tube. The tubeless automobile wheel has many advantages such as good heat dissipation and softness, good air tightness and riding comfort, long air charging interval time and the like. However, the tubeless automobile tire has a serious defect that when the tire rolls to a sharp object, the tire is easy to be punctured by the sharp object, and two situations can occur, wherein when part of the sharp object remains in the tire body, the high-pressure gas of the tire can leak outwards at the puncture part; the second is that when the sharp object pierces the tire and breaks away from the tire, the high-pressure gas of the tire leaks rapidly, which can cause the tire burst or rapid leakage of the automobile during the high-speed running process, and in serious cases, the automobile can be destroyed.
Therefore, in order to improve the safety of the new energy automobile tires, some enterprises begin to study self-sealing liquid glue at present, and the principle is that the liquid glue can be uniformly distributed on the inner surface of the tire along with the rotation of the automobile wheels, and the glue reacts with oxygen in the air to generate solidification, so that the purpose of preventing leakage of the tire is achieved. However, most of the liquid glue in the current market cannot play a good role, and the hard crystals generated after the liquid glue reacts with oxygen in the air and is solidified can reduce the elasticity of the tire, seriously affect the performance and service life of the tire, and also can generate larger potential safety hazards.
Disclosure of Invention
Aiming at the problems existing in the prior art, the invention aims to provide the disk-covered self-repairing sealing material for preventing the puncture of the tire of the new energy automobile and the preparation method thereof.
The aim of the invention is realized by adopting the following technical scheme:
in a first aspect, the invention provides a novel energy automobile tire puncture-preventing disc-covered self-repairing sealing material, which comprises a modified polyurethane sealing material and an active filler, wherein the mass ratio of the modified polyurethane sealing material to the active filler is 8.5-9.3:0.7-1.5.
Preferably, the modified polyurethane sealing material is a product obtained by using a sulfide-based compound containing a diamino group to participate in the preparation process of polyurethane.
Preferably, the active filler is obtained by activating and modifying the nano filler by using a surfactant; wherein the surfactant is dodecyl trimethyl ammonium chloride or hexadecyl trimethyl ammonium bromide; the nanometer filler is at least one of white carbon black, calcium carbonate, graphene oxide and active carbon.
Preferably, the preparation process of the active filler comprises the following steps:
firstly mixing a surfactant and deionized water in a beaker, then adding a nano filler, stirring for 4-8 hours at room temperature, removing a solvent, collecting a solid product, then flushing the solid product with deionized water for three times, and drying to obtain an active filler; wherein, the grain diameter of the nanometer filler is 250-500 nm; the mass ratio of the surfactant, the nano filler and the deionized water is 0.2-0.6:1:10-20.
Preferably, the preparation process of the double-amino thioether-based compound comprises the following steps:
s1, weighing 4-amino-2-mercaptopyrimidine and N- (4-aminophenyl) maleimide, and mixing in a reaction bottle to form a first mixed solution;
s2, dropwise adding dichloromethane into the first mixed solution, fully stirring until the dichloromethane is dissolved, dropwise adding triethylamine, and uniformly stirring at room temperature to form a second mixed solution;
and S3, continuously stirring the second mixed solution at room temperature, stopping stirring and standing when solid is precipitated in the solution, gradually precipitating the solid, washing the lower layer precipitate with petroleum ether for three times, and then drying under reduced pressure to obtain the thioether-based compound containing the diamino.
More preferably, in the step S1, the mass ratio of the 4-amino-2-mercaptopyrimidine to the N- (4-aminophenyl) maleimide is 1.3-1.8:1.9-2.4.
More preferably, in the step S2, the mass ratio of the triethylamine to the dichloromethane to the first mixed solution is 0.01-0.05:0.2-0.4:10.
More preferably, in the step S3, the solid is gradually precipitated, and then the mixture is allowed to stand for 10 to 20 minutes, and then the supernatant is separated, and the lower precipitate is washed.
Preferably, the preparation process of the modified polyurethane sealing material comprises the following steps:
p1, weighing dicyclohexylmethane diisocyanate and an organotin catalyst, mixing in a reaction container, introducing inert gas as shielding gas, and fully stirring to form a first reaction solution;
p2, weighing polytetrahydrofuran and N, N-dimethylacetamide, and fully mixing to obtain a second reaction solution;
p3, placing the reaction container in the step P1 in a water bath kettle with the temperature of 78-85 ℃, dropwise adding the second reaction liquid under the protection of inert gas, and stirring for 2-5 hours at a constant temperature after all dropwise adding to obtain an intermediate reaction liquid;
p4, mixing a thioether-based compound containing double amino groups, 1, 4-butanediol and N, N-dimethylacetamide, and uniformly stirring to obtain a third reaction solution;
p5, dropwise adding the third reaction solution into the intermediate reaction solution, carrying out heat preservation and stirring for 3-5 h to obtain a mixed reaction solution, and drying the mixed reaction solution to obtain the modified polyurethane sealing material.
More preferably, in the step P1, the organotin catalyst is stannous octoate, and the addition amount of the organotin catalyst is 0.3-0.5% of the mass of dicyclohexylmethane diisocyanate.
More preferably, in the step P2, the mass ratio of polytetrahydrofuran to N, N-dimethylacetamide is 1:1.5-2.
More preferably, in the step P3, the mass ratio of the first reaction solution to the second reaction solution is 2.8-3.6:10.
More preferably, in the step P4, the mass ratio of the thioether-based compound containing diamino, 1, 4-butanediol and N, N-dimethylacetamide is 0.8-1:0.43-0.58:15.
More preferably, in the step P5, the drying process is as follows: the mixed reaction solution is firstly placed at the temperature of 85-98 ℃ for 18-24 h, and then dried for 10-15 h under vacuum.
More preferably, in the step P5, the mass ratio of the third reaction solution to the intermediate reaction solution is 1:2-4.
In a second aspect, the invention provides a preparation method of a new energy automobile tire puncture-proof disc-covered self-repairing sealing material, which comprises the following steps: mixing the modified polyurethane sealing material and the active filler in absolute ethyl alcohol, fully and uniformly stirring, coating the mixture on the inner surface of an automobile tire, and then drying the mixture for at least 24 hours at room temperature to finish the preparation; wherein the mass ratio of the modified polyurethane sealing material to the active filler to the absolute ethyl alcohol is 8.5-9.3:0.7-1.5:20-30.
The beneficial effects of the invention are as follows:
1. the modified polyurethane sealing material prepared by the invention belongs to a polymer polyurethane variety containing various chemical groups, can be used as a self-repairing sealing material of a new energy automobile tire material, has better cohesiveness with rubber, has stronger high-temperature resistance stability, and can fill the defects of poor repairing effect and short service life of the tire protective agent in the current market.
2. The invention synthesizes a thioether-based compound containing double amino groups through chemical Click Reactions (Click Reactions) by using 4-amino-2-mercaptopyrimidine containing amino groups and mercapto groups and N- (4-aminophenyl) maleimide containing amino groups and maleimide groups. The compound can be used as a chain extender to participate in the synthesis of polyurethane, and compared with the conventional polyurethane, the prepared modified polyurethane has better self-repairing effect and plays a role in enhancing the performance of the polyurethane.
3. Rubber tires are generally used outdoors, and are inevitably exposed to a severe environment, and meanwhile, the rubber tires generate a large amount of heat due to friction force in the process of high-speed running, and the conventional polyurethane material type repairing agent is poor in hydrolysis resistance under the high-temperature condition, so that the durability of the conventional polyurethane repairing agent is poor. In addition, polyurethane itself has poor adhesion and is not highly resistant to peeling in combination with other materials, which is also a factor that affects its repairability.
4. The modified polyurethane sealing material prepared by the invention adopts the compound containing diamino, pyrimidine and covalent S-C bond to participate in chain extension modification of the polyurethane material, and various groups of the compound form hydrogen bond action, so that the self-repairing property of the polyurethane material is enhanced, the elasticity and the bonding property are enhanced, the compound can be bonded on the surface of the rubber material well, and the repairing of the rubber material can be completed smoothly in the use process.
Detailed Description
The technical features, objects and advantages of the present invention will be more clearly understood from the following detailed description of the technical aspects of the present invention, but should not be construed as limiting the scope of the invention.
The invention is further described with reference to the following examples.
Example 1
The novel energy automobile tire puncture-preventing disc-covered self-repairing sealing material comprises a modified polyurethane sealing material and an active filler, wherein the mass ratio of the modified polyurethane sealing material to the active filler is 8.9:1.1.
The preparation method of the self-repairing sealing material comprises the steps of preparing an active filler and preparing a modified polyurethane sealing material.
(1) The preparation process of the active filler comprises the following steps:
firstly mixing a surfactant dodecyl trimethyl ammonium chloride and deionized water in a beaker, then adding nano filler white carbon black, stirring for 6 hours at room temperature, removing a solvent, collecting a solid product, flushing the solid product with deionized water for three times, and drying to obtain an active filler; wherein, the grain diameter of the nanometer filler is 250-500 nm; the mass ratio of the surfactant, the nano filler and the deionized water is 0.4:1:15.
(2) The modified polyurethane sealing material is a product obtained by using a thioether-based compound containing a diamino group to participate in the preparation process of polyurethane.
The preparation process of the double-amino thioether-based compound comprises the following steps:
s1, weighing 4-amino-2-mercaptopyrimidine and N- (4-aminophenyl) maleimide, and mixing in a reaction bottle to form a first mixed solution; the mass ratio of the 4-amino-2-mercaptopyrimidine to the N- (4-aminophenyl) maleimide is 1.6:2.1.
S2, dropwise adding dichloromethane into the first mixed solution, fully stirring until the dichloromethane is dissolved, dropwise adding triethylamine, and uniformly stirring at room temperature to form a second mixed solution; the mass ratio of the triethylamine to the dichloromethane to the first mixed solution is 0.03:0.3:10.
S3, continuously stirring the second mixed solution at room temperature, stopping stirring and standing when solids are precipitated in the solution, continuously standing for 15min after the solids are gradually precipitated, separating out supernatant, washing the lower-layer precipitate separated out with petroleum ether for three times, and then drying under reduced pressure to obtain the thioether-based compound containing the diamino;
the preparation process of the modified polyurethane sealing material comprises the following steps:
p1, weighing dicyclohexylmethane diisocyanate and an organotin catalyst stannous octoate, mixing in a reaction container, wherein the adding amount of the catalyst is 0.4% of the mass of dicyclohexylmethane diisocyanate, introducing inert gas as shielding gas, and fully stirring to form a first reaction solution;
p2, weighing polytetrahydrofuran and N, N-dimethylacetamide, and fully mixing to obtain a second reaction solution; the mass ratio of polytetrahydrofuran to N, N-dimethylacetamide is 1:1.8.
P3, placing the reaction container in the step P1 in a water bath kettle at 80 ℃, dropwise adding a second reaction liquid under the protection of inert gas, and carrying out heat preservation and stirring for 3 hours after all dropwise adding to obtain an intermediate reaction liquid; the mass ratio of the first reaction liquid to the second reaction liquid is 3.2:10.
P4, mixing a thioether-based compound containing double amino groups, 1, 4-butanediol and N, N-dimethylacetamide, and uniformly stirring to obtain a third reaction solution; the mass ratio of the thioether-based compound containing the diamino, the 1, 4-butanediol and the N, N-dimethylacetamide is 0.9:0.51:15.
P5, dropwise adding the third reaction liquid into the intermediate reaction liquid, wherein the mass ratio of the third reaction liquid to the intermediate reaction liquid is 1:3, carrying out heat preservation and stirring for 4 hours to obtain a mixed reaction liquid, then drying the mixed reaction liquid, firstly placing the mixed reaction liquid at 90 ℃ for 24 hours, and then drying the mixed reaction liquid under vacuum for 12 hours to obtain the modified polyurethane sealing material.
The preparation method of the disk-covered self-repairing sealing material for preventing the puncture of the new energy automobile tire comprises the following steps:
mixing the modified polyurethane sealing material and the active filler in absolute ethyl alcohol, fully and uniformly stirring, coating the mixture on the inner surface of an automobile tire, and then drying the mixture for at least 24 hours at room temperature to finish the preparation; wherein the mass ratio of the modified polyurethane sealing material to the active filler to the absolute ethyl alcohol is 8.9:1.1:25.
Example 2
The novel energy automobile tire puncture-preventing disc-covered self-repairing sealing material comprises a modified polyurethane sealing material and an active filler, wherein the mass ratio of the modified polyurethane sealing material to the active filler is 8.5:1.5.
The preparation method of the self-repairing sealing material comprises the steps of preparing an active filler and preparing a modified polyurethane sealing material.
(1) The preparation process of the active filler comprises the following steps:
firstly mixing a surfactant cetyl trimethyl ammonium bromide and deionized water in a beaker, then adding nano filler graphene oxide, stirring for 4 hours at room temperature, removing a solvent, collecting a solid product, flushing the solid product with deionized water for three times, and drying to obtain an active filler; wherein, the grain diameter of the nanometer filler is 250-500 nm; the mass ratio of the surfactant, the nano filler and the deionized water is 0.2:1:10.
(2) The modified polyurethane sealing material is a product obtained by using a thioether-based compound containing a diamino group to participate in the preparation process of polyurethane.
The preparation process of the double-amino thioether-based compound comprises the following steps:
s1, weighing 4-amino-2-mercaptopyrimidine and N- (4-aminophenyl) maleimide, and mixing in a reaction bottle to form a first mixed solution; the mass ratio of the 4-amino-2-mercaptopyrimidine to the N- (4-aminophenyl) maleimide is 1.3:1.9.
S2, dropwise adding dichloromethane into the first mixed solution, fully stirring until the dichloromethane is dissolved, dropwise adding triethylamine, and uniformly stirring at room temperature to form a second mixed solution; the mass ratio of the triethylamine to the dichloromethane to the first mixed solution is 0.01:0.2:10.
S3, continuously stirring the second mixed solution at room temperature, stopping stirring and standing when solids are precipitated in the solution, continuously standing for 10min after the solids are gradually precipitated, separating out supernatant, washing the lower-layer precipitate separated out with petroleum ether for three times, and then drying under reduced pressure to obtain the thioether-based compound containing the diamino;
the preparation process of the modified polyurethane sealing material comprises the following steps:
p1, weighing dicyclohexylmethane diisocyanate and an organotin catalyst stannous octoate, mixing in a reaction container, wherein the adding amount of the catalyst is 0.3% of the mass of dicyclohexylmethane diisocyanate, introducing inert gas as shielding gas, and fully stirring to form a first reaction solution;
p2, weighing polytetrahydrofuran and N, N-dimethylacetamide, and fully mixing to obtain a second reaction solution; the mass ratio of polytetrahydrofuran to N, N-dimethylacetamide is 1:1.5.
P3, placing the reaction container in the step P1 in a water bath kettle at 78 ℃, dropwise adding a second reaction liquid under the protection of inert gas, and carrying out heat preservation and stirring for 2 hours after all dropwise adding to obtain an intermediate reaction liquid; the mass ratio of the first reaction liquid to the second reaction liquid is 2.8:10.
P4, mixing a thioether-based compound containing double amino groups, 1, 4-butanediol and N, N-dimethylacetamide, and uniformly stirring to obtain a third reaction solution; the mass ratio of the thioether-based compound containing the diamino, the 1, 4-butanediol and the N, N-dimethylacetamide is 0.8:0.43:15.
P5, dropwise adding the third reaction liquid into the intermediate reaction liquid, wherein the mass ratio of the third reaction liquid to the intermediate reaction liquid is 1:2, carrying out heat preservation and stirring for 3h to obtain a mixed reaction liquid, then drying the mixed reaction liquid, firstly placing the mixed reaction liquid at 85 ℃ for 18h, and then drying the mixed reaction liquid under vacuum for 10h to obtain the modified polyurethane sealing material.
The preparation method of the disk-covered self-repairing sealing material for preventing the puncture of the new energy automobile tire comprises the following steps:
mixing the modified polyurethane sealing material and the active filler in absolute ethyl alcohol, fully and uniformly stirring, coating the mixture on the inner surface of an automobile tire, and then drying the mixture for at least 24 hours at room temperature to finish the preparation; wherein the mass ratio of the modified polyurethane sealing material to the active filler to the absolute ethyl alcohol is 8.5:1.5:20.
Example 3
The novel energy automobile tire puncture-preventing disc-covered self-repairing sealing material comprises a modified polyurethane sealing material and an active filler, wherein the mass ratio of the modified polyurethane sealing material to the active filler is 9.3:0.7.
The preparation method of the self-repairing sealing material comprises the steps of preparing an active filler and preparing a modified polyurethane sealing material.
(1) The preparation process of the active filler comprises the following steps:
firstly mixing a surfactant dodecyl trimethyl ammonium chloride and deionized water in a beaker, then adding a nano calcium carbonate filler, stirring for 4-8 hours at room temperature, removing a solvent, collecting a solid product, flushing the solid product with deionized water for three times, and drying to obtain an active filler; wherein, the grain diameter of the nano calcium carbonate filler is 250-500 nm; the mass ratio of the surfactant, the nano calcium carbonate filler and the deionized water is 0.6:1:20.
(2) The modified polyurethane sealing material is a product obtained by using a thioether-based compound containing a diamino group to participate in the preparation process of polyurethane.
The preparation process of the double-amino thioether-based compound comprises the following steps:
s1, weighing 4-amino-2-mercaptopyrimidine and N- (4-aminophenyl) maleimide, and mixing in a reaction bottle to form a first mixed solution; the mass ratio of the 4-amino-2-mercaptopyrimidine to the N- (4-aminophenyl) maleimide is 1.8:2.4.
S2, dropwise adding dichloromethane into the first mixed solution, fully stirring until the dichloromethane is dissolved, dropwise adding triethylamine, and uniformly stirring at room temperature to form a second mixed solution; the mass ratio of the triethylamine to the dichloromethane to the first mixed solution is 0.05:0.4:10.
And S3, continuously stirring the second mixed solution at room temperature, stopping stirring and standing when solid is precipitated in the solution, continuously standing for 15min after the solid is gradually precipitated, separating out supernatant, washing the lower-layer precipitate separated out by using petroleum ether for three times, and then drying under reduced pressure to obtain the thioether-based compound containing the diamino.
The preparation process of the modified polyurethane sealing material comprises the following steps:
p1, weighing dicyclohexylmethane diisocyanate and an organotin catalyst stannous octoate, mixing in a reaction container, wherein the adding amount of the catalyst is 0.5% of the mass of dicyclohexylmethane diisocyanate, introducing inert gas as shielding gas, and fully stirring to form a first reaction solution;
p2, weighing polytetrahydrofuran and N, N-dimethylacetamide, and fully mixing to obtain a second reaction solution; the mass ratio of polytetrahydrofuran to N, N-dimethylacetamide is 1:2.
P3, placing the reaction container in the step P1 in a water bath kettle at 85 ℃, dropwise adding a second reaction liquid under the protection of inert gas, and carrying out heat preservation and stirring for 5 hours after all dropwise adding to obtain an intermediate reaction liquid; the mass ratio of the first reaction liquid to the second reaction liquid is 3.6:10.
P4, mixing a thioether-based compound containing double amino groups, 1, 4-butanediol and N, N-dimethylacetamide, and uniformly stirring to obtain a third reaction solution; the mass ratio of the thioether-based compound containing the diamino, the 1, 4-butanediol and the N, N-dimethylacetamide is 1:0.58:15.
P5, dropwise adding the third reaction liquid into the intermediate reaction liquid, wherein the mass ratio of the third reaction liquid to the intermediate reaction liquid is 1:4, carrying out heat preservation and stirring for 5 hours to obtain a mixed reaction liquid, then drying the mixed reaction liquid, firstly placing the mixed reaction liquid at 98 ℃ for 24 hours, and then drying for 15 hours under vacuum to obtain the modified polyurethane sealing material.
The preparation method of the disk-covered self-repairing sealing material for preventing the puncture of the new energy automobile tire comprises the following steps:
mixing the modified polyurethane sealing material and the active filler in absolute ethyl alcohol, fully and uniformly stirring, coating the mixture on the inner surface of an automobile tire, and then drying the mixture for at least 24 hours at room temperature to finish the preparation; wherein the mass ratio of the modified polyurethane sealing material to the active filler to the absolute ethyl alcohol is 9.3:0.7:30.
Comparative example 1
The self-repairing sealing material comprises the following components of common polyurethane sealing material and common filler, and is different from the embodiment 1: the modified polyurethane sealing material was replaced with a normal polyurethane sealing material, the active filler was replaced with a normal filler, and the remainder was the same as in example 1.
The preparation method of the common polyurethane sealing material comprises the following steps:
p1, weighing dicyclohexylmethane diisocyanate and an organotin catalyst stannous octoate, mixing in a reaction container, wherein the adding amount of the catalyst is 0.4% of the mass of dicyclohexylmethane diisocyanate, introducing inert gas as shielding gas, and fully stirring to form a first reaction solution;
p2, weighing polytetrahydrofuran and N, N-dimethylacetamide, and fully mixing to obtain a second reaction solution; the mass ratio of polytetrahydrofuran to N, N-dimethylacetamide is 1:1.8.
P3, placing the reaction container in the step P1 in a water bath kettle at 80 ℃, dropwise adding a second reaction liquid under the protection of inert gas, and carrying out heat preservation and stirring for 3 hours after all dropwise adding to obtain an intermediate reaction liquid; the mass ratio of the first reaction liquid to the second reaction liquid is 3.2:10.
P4, mixing 1, 4-butanediol with N, N-dimethylacetamide, and uniformly stirring to obtain a third reaction solution; the mass ratio of the 1, 4-butanediol to the N, N-dimethylacetamide is 0.51:15.
P5, dropwise adding the third reaction liquid into the intermediate reaction liquid, wherein the mass ratio of the third reaction liquid to the intermediate reaction liquid is 1:3, carrying out heat preservation and stirring for 4 hours to obtain a mixed reaction liquid, then drying the mixed reaction liquid, firstly placing the mixed reaction liquid at 90 ℃ for 24 hours, and then drying the mixed reaction liquid under vacuum for 12 hours to obtain the modified polyurethane sealing material.
Wherein the common filler is nano filler white carbon black with the particle size of 250-500 nm.
Comparative example 2
The self-repairing sealing material comprises the following components of common polyurethane sealing material and active filler, and is different from the embodiment 1: the modified polyurethane sealing material was replaced with a general polyurethane sealing material, the active filler component was unchanged, and the rest was the same as in example 1.
Among them, the general polyurethane sealing material was prepared in the same manner as in comparative example 1.
Comparative example 3
The self-repairing sealing material comprises a modified polyurethane sealing material and a common filler, and is different from the embodiment 1 in that: the active filler was replaced with a normal filler, and the composition of the modified polyurethane sealing material was unchanged, and the remainder was the same as in example 1.
Wherein the common filler is nano filler white carbon black with the particle size of 250-500 nm.
Comparative example 4
The self-repairing sealing material comprises a modified polyurethane sealing material and an active filler, and is different from the embodiment 1 in that: the modified polyurethane sealing material was prepared in the same manner as in example 1.
In the preparation of the comparative modified polyurethane sealing material, the compound containing the same diamino group (diamino terminated polydimethyl siloxane) is used for replacing the diamino thioether-based compound, and the rest steps are unchanged, namely the preparation process comprises the following steps:
p1, weighing dicyclohexylmethane diisocyanate and an organotin catalyst stannous octoate, mixing in a reaction container, wherein the adding amount of the catalyst is 0.4% of the mass of dicyclohexylmethane diisocyanate, introducing inert gas as shielding gas, and fully stirring to form a first reaction solution;
p2, weighing polytetrahydrofuran and N, N-dimethylacetamide, and fully mixing to obtain a second reaction solution; the mass ratio of polytetrahydrofuran to N, N-dimethylacetamide is 1:1.8.
P3, placing the reaction container in the step P1 in a water bath kettle at 80 ℃, dropwise adding a second reaction liquid under the protection of inert gas, and carrying out heat preservation and stirring for 3 hours after all dropwise adding to obtain an intermediate reaction liquid; the mass ratio of the first reaction liquid to the second reaction liquid is 3.2:10.
P4, mixing the diamino end-capped polydimethylsiloxane, the 1, 4-butanediol and the N, N-dimethylacetamide, and uniformly stirring to obtain a third reaction solution; the mass ratio of the diamino terminated polydimethylsiloxane, the 1, 4-butanediol and the N, N-dimethylacetamide is 0.9:0.51:15.
P5, dropwise adding the third reaction liquid into the intermediate reaction liquid, wherein the mass ratio of the third reaction liquid to the intermediate reaction liquid is 1:3, carrying out heat preservation and stirring for 4 hours to obtain a mixed reaction liquid, then drying the mixed reaction liquid, firstly placing the mixed reaction liquid at 90 ℃ for 24 hours, and then drying the mixed reaction liquid under vacuum for 12 hours to obtain the modified polyurethane sealing material.
Experimental example
In order to make the content of the invention more clear, the self-repairing sealing materials obtained in the example 1 and the comparative examples 1-3 are subjected to performance detection, and the self-repairing is completed after the fracture surface is soaked with water under the normal temperature condition. Mechanical test was referred to GB/T2941, adhesion was referred to GB/T30774, and the results are shown in Table 1:
TABLE 1 Performance of different self-healing materials
| Example 1 | Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | |
| Tensile Strength (MPa) | 6.5 | 4.7 | 5.2 | 6.3 | 6.1 |
| Elongation at break (%) | 884 | 813 | 829 | 861 | 852 |
| Elastic recovery (%) | 99 | 96 | 96 | 98 | 97 |
| Normal temperature and rubber adhesion (N/m) | 625 | 538 | 552 | 603 | 568 |
| Adhesion to rubber after high temperature treatment (N/m) | 597 | 503 | 515 | 564 | 547 |
| Self-repairing rate at normal temperature (25 ℃ C., 48 h) | 90.5 | 81.2 | 83.4 | 89.2 | 85.6 |
| High temperature self-repairing property (60 ℃ C., 20 h) | 93.8 | 84.7 | 86.1 | 91.4 | 89.2 |
As can be seen from table 1, the self-repairing sealing material prepared in example 1 of the present invention has good self-repairing property at normal temperature and high temperature, and also has good strength and elasticity, and strong adhesion to rubber. The comparative example 4, although also obtaining a certain performance improvement compared with the conventional polyurethane, has a far lower improvement amplitude than that of the example 1, and more importantly, is obviously weaker than that of the example 1 in terms of adhesion with rubber and self-repairing property, and shows that the self-repairing sealing material obtained in the example 1 of the invention has better performance than that of the product in the prior art, and is very suitable for being used as the self-repairing of automobile tires.
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made to the technical solution of the present invention without departing from the spirit and scope of the technical solution of the present invention.
Claims (8)
1. The disc-covered self-repairing sealing material for preventing the puncture of the new energy automobile tire is characterized by comprising the following components of a modified polyurethane sealing material and an active filler, wherein the mass ratio of the modified polyurethane sealing material to the active filler is 8.5-9.3:0.7-1.5; wherein the modified polyurethane sealing material is a product obtained by using a thioether-based compound containing double amino groups to participate in the preparation process of polyurethane.
2. The new energy automobile tire puncture-preventing disc-covered self-repairing sealing material according to claim 1, wherein the active filler is obtained by activating and modifying a nano filler by using a surfactant; wherein the surfactant is dodecyl trimethyl ammonium chloride or hexadecyl trimethyl ammonium bromide; the nanometer filler is at least one of white carbon black, calcium carbonate, graphene oxide and active carbon.
3. The new energy automobile tire puncture-preventing disc-covered self-repairing sealing material according to claim 3, wherein the preparation process of the active filler comprises the following steps:
firstly mixing a surfactant and deionized water in a beaker, then adding a nano filler, stirring for 4-8 hours at room temperature, removing a solvent, collecting a solid product, then flushing the solid product with deionized water for three times, and drying to obtain an active filler; wherein, the grain diameter of the nanometer filler is 250-500 nm; the mass ratio of the surfactant, the nano filler and the deionized water is 0.2-0.6:1:10-20.
4. The novel energy automobile tire puncture-preventing disc-covered self-repairing sealing material according to claim 1, wherein the preparation process of the diamino thioether-based compound comprises the following steps:
s1, weighing 4-amino-2-mercaptopyrimidine and N- (4-aminophenyl) maleimide, and mixing in a reaction bottle to form a first mixed solution;
s2, dropwise adding dichloromethane into the first mixed solution, fully stirring until the dichloromethane is dissolved, dropwise adding triethylamine, and uniformly stirring at room temperature to form a second mixed solution;
and S3, continuously stirring the second mixed solution at room temperature, stopping stirring and standing when solid is precipitated in the solution, gradually precipitating the solid, washing the lower layer precipitate with petroleum ether for three times, and then drying under reduced pressure to obtain the thioether-based compound containing the diamino.
5. The novel energy automobile tire puncture-preventing disc-covered self-repairing sealing material according to claim 1, wherein in the step S1, the mass ratio of 4-amino-2-mercaptopyrimidine to N- (4-aminophenyl) maleimide is 1.3-1.8:1.9-2.4;
in the step S2, the mass ratio of the triethylamine to the dichloromethane to the first mixed solution is 0.01-0.05:0.2-0.4:10;
in the step S3, after the solid is gradually precipitated, the solid is kept still for 10 to 20 minutes, and then the supernatant is separated out, and the lower-layer sediment is washed.
6. The novel energy automobile tire puncture-preventing disc-covered self-repairing sealing material according to claim 1, wherein the preparation process of the modified polyurethane sealing material comprises the following steps:
p1, weighing dicyclohexylmethane diisocyanate and an organotin catalyst, mixing in a reaction container, introducing inert gas as shielding gas, and fully stirring to form a first reaction solution;
p2, weighing polytetrahydrofuran and N, N-dimethylacetamide, and fully mixing to obtain a second reaction solution;
p3, placing the reaction container in the step P1 in a water bath kettle with the temperature of 78-85 ℃, dropwise adding the second reaction liquid under the protection of inert gas, and stirring for 2-5 hours at a constant temperature after all dropwise adding to obtain an intermediate reaction liquid;
p4, mixing a thioether-based compound containing double amino groups, 1, 4-butanediol and N, N-dimethylacetamide, and uniformly stirring to obtain a third reaction solution;
p5, dropwise adding the third reaction solution into the intermediate reaction solution, carrying out heat preservation and stirring for 3-5 h to obtain a mixed reaction solution, and drying the mixed reaction solution to obtain the modified polyurethane sealing material.
7. The novel energy automobile tire puncture-preventing disc-covered self-repairing sealing material according to claim 1, wherein in the step P1, the organotin catalyst is stannous octoate, and the addition amount of the organotin catalyst is 0.3-0.5% of the mass of dicyclohexylmethane diisocyanate;
in the step P2, the mass ratio of polytetrahydrofuran to N, N-dimethylacetamide is 1:1.5-2;
in the step P3, the mass ratio of the first reaction liquid to the second reaction liquid is 2.8-3.6:10;
in the step P4, the mass ratio of the thioether-based compound containing the diamino, the 1, 4-butanediol and the N, N-dimethylacetamide is 0.8-1:0.43-0.58:15;
in the step P5, the drying treatment process is as follows: firstly, placing the mixed reaction solution at 85-98 ℃ for 18-24 hours, and then drying the mixed reaction solution for 10-15 hours under vacuum;
in the step P5, the mass ratio of the third reaction liquid to the intermediate reaction liquid is 1:2-4.
8. A method for preparing the puncture-preventing disc-covered self-repairing sealing material for a new energy automobile tire according to any one of claims 1 to 7, which is characterized by comprising the following steps: mixing the modified polyurethane sealing material and the active filler in absolute ethyl alcohol, fully and uniformly stirring, coating the mixture on the inner surface of an automobile tire, and then drying the mixture for at least 24 hours at room temperature to finish the preparation; wherein the mass ratio of the modified polyurethane sealing material to the active filler to the absolute ethyl alcohol is 8.5-9.3:0.7-1.5:20-30.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310386169.4A CN116396605B (en) | 2023-04-12 | 2023-04-12 | New energy automobile tire puncture-preventing disc-covered self-repairing sealing material and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310386169.4A CN116396605B (en) | 2023-04-12 | 2023-04-12 | New energy automobile tire puncture-preventing disc-covered self-repairing sealing material and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN116396605A true CN116396605A (en) | 2023-07-07 |
| CN116396605B CN116396605B (en) | 2023-09-19 |
Family
ID=87015650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310386169.4A Active CN116396605B (en) | 2023-04-12 | 2023-04-12 | New energy automobile tire puncture-preventing disc-covered self-repairing sealing material and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116396605B (en) |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000038567A (en) * | 1998-07-22 | 2000-02-08 | Nippon Polyurethane Ind Co Ltd | Thermally curable urethane sealing material |
| JP2007224232A (en) * | 2006-02-27 | 2007-09-06 | Yokohama Rubber Co Ltd:The | Puncture sealing material for tire |
| WO2021062571A1 (en) * | 2019-09-30 | 2021-04-08 | Universidad Tecnológica Metropolitana | Cross-linked and recyclable electroconductive carbonaceous nanocompounds and polymers capable of dispersing and stabilising them, method, derived materials and uses |
| CN113249025A (en) * | 2021-06-16 | 2021-08-13 | 四川大学 | Near-infrared quick response accurate self-repairing anticorrosive coating and preparation method thereof |
| JP2021152115A (en) * | 2020-03-24 | 2021-09-30 | 東ソー株式会社 | Multimer composition, blocked multimer composition and method for producing the same |
| CN113563562A (en) * | 2021-08-23 | 2021-10-29 | 无锡安睿驰科技有限公司 | Disc-type self-repairing safety tire rubber material and preparation method thereof |
| CN113583237A (en) * | 2021-08-23 | 2021-11-02 | 无锡安睿驰科技有限公司 | Self-repairing coating material and coating type punctured self-sealing tire based on same |
| WO2022039927A1 (en) * | 2020-08-18 | 2022-02-24 | Covestro Llc | One-component waterborne polyurethane self-healing coatings using hydrophobic blocked polyisocyanates |
| CN115873251A (en) * | 2022-12-27 | 2023-03-31 | 苏州生益科技有限公司 | Modified maleimide prepolymer, preparation method thereof and resin composition |
| CN115948112A (en) * | 2023-01-03 | 2023-04-11 | 成都鑫岩乔新材料科技有限公司 | Waterborne polyurethane coating and preparation process thereof |
-
2023
- 2023-04-12 CN CN202310386169.4A patent/CN116396605B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000038567A (en) * | 1998-07-22 | 2000-02-08 | Nippon Polyurethane Ind Co Ltd | Thermally curable urethane sealing material |
| JP2007224232A (en) * | 2006-02-27 | 2007-09-06 | Yokohama Rubber Co Ltd:The | Puncture sealing material for tire |
| WO2021062571A1 (en) * | 2019-09-30 | 2021-04-08 | Universidad Tecnológica Metropolitana | Cross-linked and recyclable electroconductive carbonaceous nanocompounds and polymers capable of dispersing and stabilising them, method, derived materials and uses |
| JP2021152115A (en) * | 2020-03-24 | 2021-09-30 | 東ソー株式会社 | Multimer composition, blocked multimer composition and method for producing the same |
| WO2022039927A1 (en) * | 2020-08-18 | 2022-02-24 | Covestro Llc | One-component waterborne polyurethane self-healing coatings using hydrophobic blocked polyisocyanates |
| CN113249025A (en) * | 2021-06-16 | 2021-08-13 | 四川大学 | Near-infrared quick response accurate self-repairing anticorrosive coating and preparation method thereof |
| CN113563562A (en) * | 2021-08-23 | 2021-10-29 | 无锡安睿驰科技有限公司 | Disc-type self-repairing safety tire rubber material and preparation method thereof |
| CN113583237A (en) * | 2021-08-23 | 2021-11-02 | 无锡安睿驰科技有限公司 | Self-repairing coating material and coating type punctured self-sealing tire based on same |
| CN115873251A (en) * | 2022-12-27 | 2023-03-31 | 苏州生益科技有限公司 | Modified maleimide prepolymer, preparation method thereof and resin composition |
| CN115948112A (en) * | 2023-01-03 | 2023-04-11 | 成都鑫岩乔新材料科技有限公司 | Waterborne polyurethane coating and preparation process thereof |
Non-Patent Citations (4)
| Title |
|---|
| NORTHROP, BH，等: "Thiol-maleimide "click" chemistry: evaluating the influence of solvent, initiator, and thiol on the reaction mechanism, kinetics, and selectivity", POLYMER CHEMISTRY, vol. 06, no. 18, pages 3415 - 3430, XP055559389, DOI: 10.1039/C5PY00168D * |
| SUGANE, K，等: "Thermally healable/heat-resistant properties of thermosets bearing dynamic and thermally stable bonds formed by the Diels-Alder and thiol-maleimide "click" reactions", REACTIVE & FUNCTIONAL POLYMERS, vol. 131, pages 211 - 218 * |
| 谢永生，等: "碱催化C-S偶联反应——"绿色的"巯基-马来酰亚胺点击化学教学实验", 重庆三峡学院学报, vol. 29, no. 145, pages 117 - 119 * |
| 郭亚昆，等: "外援型自修复体系及其在环氧基复合材料中的应用", 材料导报, no. 01, pages 72 - 76 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN116396605B (en) | 2023-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111117546B (en) | High-temperature-resistant silane modified adhesive, and preparation method and application thereof | |
| WO2022147914A1 (en) | Solvent-free polyurethane resin for high-flame-retardancy automobile leather, and preparation method therefor | |
| CN116396605B (en) | New energy automobile tire puncture-preventing disc-covered self-repairing sealing material and preparation method thereof | |
| CN113563562B (en) | Disc-type self-repairing safety tire rubber material and preparation method thereof | |
| CN112409854A (en) | Stone-impact-resistant coating for low-density aluminum substrate | |
| CN114395297A (en) | Sealing gasket coated with fluororubber and production process thereof | |
| CN107555460A (en) | A kind of Nano calcium carbonate dedicated preparation method of rubber tyre | |
| CN108641666B (en) | Sealant for aircraft fuel tank and preparation method thereof | |
| CN114163698B (en) | High-durability low-heat-generation mining engineering tire belt rubber and preparation method thereof | |
| CN115926714A (en) | Single-component polyurethane adhesive and preparation method and application thereof | |
| CN112898672B (en) | Rubber composition with self-sealing function, preparation method and tire | |
| CN101323175B (en) | Radial tire ring traveler component and preparation technique | |
| CN113150409A (en) | Rubber composition for all-steel radial tire body and preparation method thereof | |
| WO2019213948A1 (en) | Butadiene rubber-polyurethane elastomer material having ultra-low rolling resistance and preparation method therefor | |
| CN107502070A (en) | A kind of tire protection agent and preparation method thereof | |
| JP2020125457A (en) | Adhesive composition and method of manufacturing nonpneumatic tire using the same | |
| CN113105823B (en) | Polyurethane finish paint and preparation method and application thereof | |
| CN113683985B (en) | Environment-friendly foaming butyl sealant composition, environment-friendly foaming butyl sealant, and preparation method and application thereof | |
| CN116655988B (en) | Surface treatment method of vulcanized rubber, application of surface treatment method, rubber-polyurethane composite tire and preparation method of rubber-polyurethane composite tire | |
| CN111320789B (en) | Environment-friendly efficient tire repairing agent and preparation method thereof | |
| CN114836041B (en) | Composite insulator rubber compound and preparation method and application thereof | |
| CN117186832A (en) | Storage-stable one-component dealcoholized organosilicon sealant composition and preparation method thereof | |
| CN117165254A (en) | Single-component dealcoholized organosilicon sealant composition for anti-fog car lamp, and preparation method and application thereof | |
| CN115948100B (en) | Composite material composition, preparation method of composite material, composite material and application | |
| CN111825891B (en) | High-performance automobile tire steel wire rubber and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |