CN113980453A - Antistatic polyurethane solid tire material - Google Patents
Antistatic polyurethane solid tire material Download PDFInfo
- Publication number
- CN113980453A CN113980453A CN202111565094.3A CN202111565094A CN113980453A CN 113980453 A CN113980453 A CN 113980453A CN 202111565094 A CN202111565094 A CN 202111565094A CN 113980453 A CN113980453 A CN 113980453A
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- CN
- China
- Prior art keywords
- antistatic
- modified
- parts
- solid tire
- polyurethane solid
- 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.)
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 68
- 239000004814 polyurethane Substances 0.000 title claims abstract description 68
- 239000007787 solid Substances 0.000 title claims abstract description 56
- 239000000463 material Substances 0.000 title claims abstract description 46
- 239000002216 antistatic agent Substances 0.000 claims abstract description 49
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 22
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003063 flame retardant Substances 0.000 claims abstract description 20
- 229920005862 polyol Polymers 0.000 claims abstract description 16
- 150000003077 polyols Chemical class 0.000 claims abstract description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 14
- 229920000570 polyether Polymers 0.000 claims abstract description 14
- 239000004970 Chain extender Substances 0.000 claims abstract description 13
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 11
- 239000012948 isocyanate Substances 0.000 claims abstract description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 6
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims description 45
- 238000010438 heat treatment Methods 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 23
- -1 polysiloxane Polymers 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
- 229920001296 polysiloxane Polymers 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical class C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 claims description 13
- 238000002390 rotary evaporation Methods 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 238000001291 vacuum drying Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 238000000967 suction filtration Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 150000003242 quaternary ammonium salts Chemical group 0.000 abstract description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000001105 regulatory effect Effects 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- 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
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3889—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having nitrogen in addition to phosphorus
-
- 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
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6611—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/001—Conductive additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/04—Antistatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention relates to an anti-static polyurethane solid tire material, and belongs to the technical field of polyurethane tire manufacturing. The anti-static polyurethane solid tire material comprises the following raw materials: polyether polyol, polyester polyol, a chain extender, isocyanate, a cross-linking agent, modified conductive carbon black, a modified antistatic agent and a reactive flame retardant. The modified conductive carbon black can not only reinforce the polyurethane solid wheelThe mechanical strength of the tire can be improved by utilizing the conductivity of the conductive carbon black, but the antistatic effect of the tire is limited, therefore, the invention also introduces a modified antistatic agent which has FeCl3The antistatic polyurethane solid tire has the double conductive function with the quaternary ammonium salt structure, has excellent antistatic effect, and improves the antistatic performance of the polyurethane solid tire in cooperation with conductive carbon black; the reactive flame retardant has a DOPO flame retardant structure, contains fluoromethyl and amino, and improves the thermal stability of the polyurethane solid tire.
Description
Technical Field
The invention belongs to the technical field of polyurethane tire manufacturing, and particularly relates to an anti-static polyurethane solid tire material.
Background
Tires, which are main accessories of vehicles, are classified into pneumatic tires and solid tires. The pneumatic tire has good buffering effect, but is easy to wear and leak, so the pneumatic tire is generally applied to vehicles with higher requirements on comfort level and running speed; the solid tire has the advantages of high load resistance, high strength, high tearing resistance, puncture resistance and the like, and is mainly used for vehicles which have requirements on load and are used outdoors for a long time. Compared with the traditional rubber solid tire, the polyurethane solid tire has the characteristics of good elasticity and easy recycling, and is widely popular in the market. For example, the patent CN106800637A discloses a wear-resistant polyurethane solid tire, which is formed by casting a polyol, wherein the polyol which is one of the main raw materials is polyether polyol with the molecular weight of 6000-; the polyurethane solid tire reported in patent CN104497252A adopts two polyether polyols with different molecular weights and 3 functionalities, and the method for manufacturing the solid tire is simple and easy to implement and has high production efficiency; the patent CN105330811A discloses a polyurethane solid tire material, which comprises a component A and a component B, wherein the component A is polyester polyol, a chain extender, a foaming agent, a catalyst A and a foam stabilizer, and the component B is isocyanate, polyester polyol and polyether polyol.
However, in the application process of the polyurethane solid tire, because of heavy load, the friction with the ground is serious, and a large amount of static charges and a large amount of heat are easily accumulated on a contact surface, so that the polyurethane chain is softened and decomposed, and the service life of the polyurethane solid tire is shortened. Therefore, the technical problems to be solved by the polyurethane solid tire are that the thermal stability and the antistatic capability of the polyurethane solid tire are improved, the electric charge generated by friction is reduced, and the service life of the polyurethane solid tire is prolonged.
For example, the polyurethane for manufacturing the solid tire disclosed in the Chinese patent CN104497252A is prepared from a component A and a component B according to the following parts by weight: the component A comprises: 180-90 parts of polyether polyol, 210-20 parts of polyester polyol, 0.1-0.2 part of foam stabilizer, 0.3-0.40 part of amine catalyst, 0.05-0.10 part of metal catalyst, 3-5 parts of cross-linking agent and 1 part of chain extender: 5-7 parts of a chain extender 2: 10-12 parts of physical foaming agent, 5-10 parts of component B, and 110 parts of modified black material. However, the polyurethane has low thermal stability.
Therefore, the invention provides an antistatic polyurethane solid tire material.
Disclosure of Invention
The invention aims to provide an antistatic polyurethane solid tire material to solve the technical problems mentioned in the background technology.
The purpose of the invention can be realized by the following technical scheme:
the anti-static polyurethane solid tire material comprises the following raw materials in parts by weight: 100-170 parts of polyether polyol, 140-250 parts of polyester polyol, 15-23 parts of chain extender, 18-40 parts of isocyanate, 4-8.5 parts of cross-linking agent, 5-18 parts of modified conductive carbon black, 8-20 parts of modified antistatic agent and 25-55 parts of reactive flame retardant.
Further, the polyether polyol has a number average molecular weight of 2000-3000 and an average hydroxyl functionality of 2-3.
Further, the number average molecular weight of the polyester polyol is 2500-3500, and the average hydroxyl functionality is 2-3.
Further, the chain extender is a mixture of ethylene glycol, butanediol and hexanediol in any ratio.
Further, the cross-linking agent is a mixture of trimethylolpropane, pentaerythritol and maleic anhydride in any ratio.
Furthermore, the modified conductive carbon black is the conductive carbon black modified by a silane coupling agent, the dispersion degree of the conductive carbon black in a polyurethane system is improved, the enhancement effect of the conductive carbon black on the polyurethane strength is promoted, and the silane coupling agent is selected from one of KH560, KH550 and KH 570.
Further, the modified antistatic agent is prepared by the following steps:
x1, uniformly mixing 4-vinylpyridine, 1,3, 3-tetramethylsilane and toluene, heating to 93 ℃ under the protection of nitrogen, adding chloroplatinic acid isopropanol solution, reacting for 5 hours, adsorbing a platinum catalyst by using activated carbon after the reaction is finished, filtering, and removing the solvent by rotary evaporation to obtain the modified polysiloxane, wherein the molar ratio of the 4-vinylpyridine to the 1,1,3, 3-tetramethylsilane is 1: 1, the adding amount of the chloroplatinic acid isopropanol solution is 0.5-3.5 percent of the total mass of the 4-vinylpyridine and the 1,1,3, 3-tetramethylsilane, and the mass fraction of the chloroplatinic acid isopropanol solution is 1 percent;
in the reaction, the modified polysiloxane is obtained by utilizing the addition polymerization reaction of double bonds and silicon hydrogen under the action of chloroplatinic acid, and the molecular structural formula of the modified polysiloxane is shown as follows;
x2, sequentially adding modified polysiloxane and nitromethane into a three-neck flask, stirring until the modified polysiloxane is completely dissolved, then adding 1-bromon-hexane under the conditions of nitrogen and stirring, heating to 65 ℃, stirring for reacting for 24 hours, after the reaction is finished, precipitating with methanol, filtering, washing, and drying in vacuum to obtain the antistatic agent, wherein the dosage ratio of the modified polysiloxane, the nitromethane and the 1-bromon-hexane is 10-14 g: 100 and 200 mL: 0.7-1.8 g;
in the X2 reaction, the reaction of nitrogen atoms in pyridine rings and bromine in 1-bromine n-hexane is utilized, so that a molecular chain of the modified polysiloxane is introduced into a quaternary ammonium structure to obtain the antistatic agent, wherein the molecular structural formula is shown as follows;
x3, heating and stirring the antistatic agent and anhydrous chloroform until the antistatic agent is completely dissolved, controlling the temperature not to exceed 55 ℃ in the stirring process, then stopping heating, cooling to room temperature, dropwise adding FeCl3The methanol solution is dropwise added at the speed of 1 drop/3 seconds, after the dropwise addition is completed, the stirring reaction is continued for 40-60min, the solvent is removed by rotary evaporation, and then the vacuum drying is carried out to obtain the modified antistatic agent, wherein the antistatic agent, chloroform and FeCl are adopted as raw materials3The dosage ratio of the methanol is 20 g: 70-90 mL: 12 g: 60-80 mL.
In the X3 reaction, nitrogen atoms in non-quaternized pyridine rings in the antistatic agent and iron ions form coordinate bonds, so that iron ions are wrapped by molecular chains of the antistatic agent to obtain the modified antistatic agent.
Further, the reactive flame retardant is prepared by the following steps:
b1, adding 5-nitro-2-chlorotrifluoromethane, DOPO-BQ, potassium carbonate and DMF (dimethyl formamide) into a three-neck flask with a stirring device, heating to 130 ℃ in an oil bath, stirring for reacting for 24 hours, cooling, carrying out suction filtration, removing precipitates to obtain a filtrate, carrying out rotary evaporation and concentration on the filtrate, and drying in a vacuum drying oven to obtain the DOPO derivative, wherein the molar ratio of the 5-nitro-2-chlorotrifluoromethane to the DOPO-BQ to the potassium carbonate is 2.1-2.3: 1: 2;
in the reaction, the substitution reaction of chlorine in 5-nitro-2-chlorotrifluoromethane and hydroxyl in DOPO-BQ is utilized to obtain the DOPO derivative, and the molecular structural formula of the DOPO derivative is shown as follows;
b2, adding iron powder, ethanol and deionized water into a four-neck flask with a condensation reflux and stirring device, regulating the pH value of a solution to be 4-5 by hydrochloric acid, stirring and boiling for 30-40min to activate the iron powder, stopping heating, cooling to room temperature, adding a DOPO derivative under a stirring state, heating to 80 ℃, reacting for 4h, stopping reaction, cooling to room temperature, performing suction filtration, regulating the pH value to be 9-10, generating precipitates, performing suction filtration again, concentrating the filtrate in a rotary evaporator, pouring the concentrated solution into deionized water, separating out gray products, filtering, recrystallizing and performing vacuum drying to obtain the reactive flame retardant, wherein the dosage ratio of the iron powder, the ethanol, the deionized water and the DOPO derivative is 30-40 g: 100mL of: 100mL of: 60-70g, the nitro group in the DOPO derivative is reduced into amino group by utilizing the reduction effect of iron powder.
The invention has the beneficial effects that:
in order to improve the antistatic performance of the polyurethane solid tire, the invention introduces the modified conductive carbon black and the modified antistatic agent, firstly, the conductive carbon black is low in price, and the modified conductive carbon black is modified by the silane coupling agent, has good dispersion performance in the polyurethane base material, andthe conductive performance is realized, the antistatic capacity of the polyurethane solid tire can be improved to a certain extent, but more of the antistatic capacity is shown in the strength enhancement of the polyurethane solid tire; in order to improve the antistatic performance of the polyurethane solid tire, the invention introduces the modified antistatic agent which is quaternary ammonium salt antistatic agent loaded FeCl3Of FeCl3The double conductive function with the quaternary ammonium salt structure, the antistatic effect is excellent; the main chain of the modified antistatic agent contains a siloxane chain, so that the modified antistatic agent has good compatibility with the polyurethane base material, and the introduction of the siloxane chain improves the thermal stability of the polyurethane base material to a certain extent; meanwhile, in order to improve the thermal stability of polyurethane to the maximum extent, the invention introduces a reactive flame retardant, the reactive flame retardant is obtained by taking 5-nitro-2-chlorotrifluoromethane and DOPO-BQ as raw materials to react step by step, and has a DOPO flame retardant structure, a fluoromethyl group and an amino group, the amino group endows the reactive flame retardant with reactivity, and the amino group reacts with groups such as isocyanate group, carboxyl group and the like in a polyurethane system to participate in the formation of a polyurethane material crosslinking network, so that the crosslinking degree of the polyurethane material is improved, and the hardness of the polyurethane material is improved; the fluorine-containing methyl group endows the polyurethane material with waterproof, acid and alkali resistant properties; the DOPO flame-retardant structure endows the polyurethane material with thermal stability;
in conclusion, the anti-static polyurethane solid tire material provided by the invention has excellent anti-static, thermal stability, water resistance and acid and alkali resistance.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparation of reactive flame retardant:
b1, adding 0.21mol of 5-nitro-2-chlorotrifluoromethane, 0.1mol of DOPO-BQ, 0.2mol of potassium carbonate and 100mL of DMF into a three-neck flask with a stirring device, heating to 130 ℃ in an oil bath, stirring for reaction for 24 hours, cooling, carrying out suction filtration, removing precipitates to obtain a filtrate, carrying out rotary evaporation and concentration on the filtrate, and drying in a vacuum drying oven to obtain the DOPO derivative;
b2, adding 30g of iron powder, 100mL of ethanol and 100mL of deionized water into a four-neck flask with a condensation reflux and stirring device, regulating the pH value of the solution to be 4 by hydrochloric acid, stirring and boiling for 30min to activate the iron powder, stopping heating, cooling to room temperature, adding 60g of DOPO derivative under the stirring state, heating to 80 ℃, reacting for 4h, stopping reaction, cooling to room temperature, performing suction filtration, regulating the pH value to be 9 to generate precipitates, performing suction filtration again, concentrating the filtrate in a rotary evaporator, pouring the concentrated solution into deionized water, separating out a gray product, filtering, recrystallizing and performing vacuum drying to obtain the reactive flame retardant.
Example 2
Preparation of reactive flame retardant:
b1, adding 0.23mol of 5-nitro-2-chlorotrifluoromethane, 0.1mol of DOPO-BQ, 0.2mol of potassium carbonate and 100mL of DMF into a three-neck flask with a stirring device, heating to 130 ℃ in an oil bath, stirring for reaction for 24 hours, cooling, carrying out suction filtration, removing precipitates to obtain a filtrate, carrying out rotary evaporation and concentration on the filtrate, and drying in a vacuum drying oven to obtain the DOPO derivative;
b2, adding 40g of iron powder, 100mL of ethanol and 100mL of deionized water into a four-neck flask with a condensation reflux and stirring device, regulating the pH value of the solution to 5 by hydrochloric acid, stirring and boiling for 40min to activate the iron powder, stopping heating, cooling to room temperature, adding 70g of DOPO derivative under the stirring state, heating to 80 ℃, reacting for 4h, stopping reaction, cooling to room temperature, performing suction filtration, regulating the pH value to 10 to generate a precipitate, performing suction filtration again, concentrating the filtrate in a rotary evaporator, pouring the concentrated solution into deionized water, separating out a gray product, filtering, recrystallizing and performing vacuum drying to obtain the reactive flame retardant.
Example 3
Preparing a modified antistatic agent:
x1, uniformly mixing 0.1mol of 4-vinylpyridine, 0.1mol of 1,1,3, 3-tetramethylsilane and toluene, heating to 93 ℃ under the protection of nitrogen, adding 11.85g of chloroplatinic acid isopropanol solution, reacting for 5 hours, adsorbing a platinum catalyst by using activated carbon after the reaction is finished, filtering, and removing the solvent by rotary evaporation to obtain modified polysiloxane, wherein the mass fraction of the chloroplatinic acid isopropanol solution is 1%;
x2, sequentially adding 10g of modified polysiloxane and 100mL of nitromethane into a three-neck flask, stirring until the modified polysiloxane is completely dissolved, then adding 0.7g of 1-bromon-hexane under the conditions of nitrogen and stirring, heating to 65 ℃, stirring for reacting for 24 hours, after the reaction is finished, precipitating with methanol, filtering, washing, and drying in vacuum to obtain the antistatic agent;
x3, heating and stirring 20g of antistatic agent and 70mL of anhydrous chloroform until the antistatic agent is completely dissolved, controlling the temperature to be not more than 55 ℃ in the stirring process, then stopping heating, cooling to room temperature, and dropwise adding 60mL of FeCl containing 12g3The dropping speed of the methanol solution is 1 drop/3 seconds, after the dropping is completed, the stirring reaction is continued for 40min, the solvent is removed by rotary evaporation, and then the modified antistatic agent is obtained by vacuum drying.
Example 4
Preparing a modified antistatic agent:
x1, uniformly mixing 0.1mol of 4-vinylpyridine, 0.1mol of 1,1,3, 3-tetramethylsilane and toluene, heating to 93 ℃ under the protection of nitrogen, adding 83.55g of chloroplatinic acid isopropanol solution, reacting for 5 hours, adsorbing a platinum catalyst by using activated carbon after the reaction is finished, filtering, and removing the solvent by rotary evaporation to obtain modified polysiloxane, wherein the mass fraction of the chloroplatinic acid isopropanol solution is 1%;
x2, sequentially adding 14g of modified polysiloxane and 200mL of nitromethane into a three-neck flask, stirring until the modified polysiloxane is completely dissolved, then adding 1.8g of 1-bromon-hexane under the conditions of nitrogen and stirring, heating to 65 ℃, stirring for reacting for 24 hours, after the reaction is finished, precipitating with methanol, filtering, washing, and drying in vacuum to obtain the antistatic agent;
x3, heating and stirring 20g of antistatic agent and 90mL of anhydrous chloroform until the antistatic agent is completely dissolved, and controlling the temperature to be not more than 5 in the stirring processStopping heating at 5 ℃, cooling to room temperature, and dropwise adding 80mL of FeCl containing 12g3The dropping speed of the methanol solution is 1 drop/3 seconds, after the dropping is completed, the stirring reaction is continued for 60min, the solvent is removed by rotary evaporation, and then the modified antistatic agent is obtained by vacuum drying.
Example 5
The anti-static polyurethane solid tire material comprises the following raw materials in parts by weight: 100 parts of polyether polyol, 140 parts of polyester polyol, 15 parts of chain extender, 18 parts of isocyanate, 4 parts of cross-linking agent, 5 parts of modified conductive carbon black, 8 parts of modified antistatic agent prepared in example 3 and 25 parts of reactive flame retardant prepared in example 1, wherein the polyether polyol has the number average molecular weight of 2000-2500 and the average hydroxyl functionality of 2-3, the polyester polyol has the number average molecular weight of 2500-2500 and the average hydroxyl functionality of 2-3, the chain extender is ethylene glycol and butanediol according to the mass ratio of 1: 1, and the cross-linking agent is trimethylolpropane and pentaerythritol in a mass ratio of 1: 1, and the modified conductive carbon black is conductive carbon black modified by a silane coupling agent KH 560.
Example 6
The anti-static polyurethane solid tire material comprises the following raw materials in parts by weight: 130 parts of polyether polyol, 200 parts of polyester polyol, 17 parts of chain extender, 26 parts of isocyanate, 6 parts of cross-linking agent, 11 parts of modified conductive carbon black, 15 parts of modified antistatic agent prepared in example 4 and 30 parts of reactive flame retardant prepared in example 2, wherein the polyether polyol has the number average molecular weight of 2500-3000, the average hydroxyl functionality of 2-3, the polyester polyol has the number average molecular weight of 3000-3500 and the average hydroxyl functionality of 2-3, the chain extender is ethylene glycol, butanediol and hexanediol according to the mass ratio of 1: 1: 1, the cross-linking agent is a mixture of trimethylolpropane, pentaerythritol and maleic anhydride in any ratio, and the modified conductive carbon black is conductive carbon black modified by a silane coupling agent KH 550.
Example 7
The anti-static polyurethane solid tire material comprises the following raw materials in parts by weight: 170 parts of polyether polyol, 250 parts of polyester polyol, 23 parts of chain extender, 40 parts of isocyanate, 8.5 parts of cross-linking agent, 18 parts of modified conductive carbon black, 20 parts of modified antistatic agent prepared in example 3 and 55 parts of reactive flame retardant prepared in example 1, wherein the polyether polyol has the number average molecular weight of 2500-3000, the average hydroxyl functionality of 2-3, the polyester polyol has the number average molecular weight of 2500-3000 and the average hydroxyl functionality of 2-3, and the chain extender is ethylene glycol and hexanediol according to the mass ratio of 1: 2, and the cross-linking agent is trimethylolpropane and pentaerythritol in a mass ratio of 3: 1, and the modified conductive carbon black is conductive carbon black modified by a silane coupling agent KH 570.
Comparative example 1
The antistatic agent was prepared as in example 3 step X2.
Comparative example 2
Preparing a modified antistatic agent:
x1, uniformly mixing 0.1mol of 4-vinylpyridine, 0.1mol of 1,1,3, 3-tetramethylsilane and toluene, heating to 93 ℃ under the protection of nitrogen, adding 11.85g of chloroplatinic acid isopropanol solution, reacting for 5 hours, adsorbing a platinum catalyst by using activated carbon after the reaction is finished, filtering, and removing the solvent by rotary evaporation to obtain modified polysiloxane, wherein the mass fraction of the chloroplatinic acid isopropanol solution is 1%;
x2, heating and stirring 20g of antistatic agent and 70mL of anhydrous chloroform until the antistatic agent is completely dissolved, controlling the temperature to be not more than 55 ℃ in the stirring process, then stopping heating, cooling to room temperature, and dropwise adding 60mL of FeCl containing 12g3The dropping speed of the methanol solution is 1 drop/3 seconds, after the dropping is completed, the stirring reaction is continued for 40min, the solvent is removed by rotary evaporation, water is added for recrystallization, and then the modified antistatic agent is obtained by vacuum drying.
Comparative example 3
Compared with example 5, the antistatic polyurethane solid tire material has the same modification antistatic agent prepared in the comparative example 1 replaced by the modification antistatic agent.
Comparative example 4
Compared with example 6, the antistatic polyurethane solid tire material replaces the modified antistatic agent prepared in the proportion 2 with the modified antistatic agent, and the rest is the same.
Comparative example 5
Compared with the material of the solid polyurethane tire in the embodiment 7, the material of the solid polyurethane tire has the same material except that the modified carbon black in the raw material is deleted.
Comparative example 6
Compared with the material of the solid polyurethane tire in the embodiment 5, the material of the solid polyurethane tire is the same except that the modified antistatic agent in the raw material is deleted.
Comparative example 7
Compared with the material of the solid polyurethane tire in the example 6, the material of the solid polyurethane tire has the same material except that the reactive flame retardant in the raw material is replaced by DOPO-BQ.
Comparative example 8
Compared with the material of the solid polyurethane tire in the embodiment 6, the material of the solid polyurethane tire is the same except that the reactive flame retardant in the raw materials is deleted.
Example 9
The polyurethane solid tire materials obtained in examples 5 to 7 and comparative examples 3 to 8 were mixed and injection-molded to obtain a polyurethane solid tire, and the polyurethane solid tire was prepared as a test sample, and then the following performance tests were performed:
tensile property: testing according to GB/T528;
tear strength: testing according to GB/T529;
hardness: testing the Shore A hardness on a CYX-A type durometer according to GB/T531;
thermal stability: thermogravimetric analysis (TG) is tested by adopting a TG209 type thermogravimetric analyzer, the test temperature range is 20-600 ℃, the heating rate is 10 ℃/min, and N is used2The flow rate is 20mL/min for blowing gas and protective gas;
surface resistance: the test was carried out using a model PC68 digital high impedance meter. And (3) testing conditions are as follows: drying the sample before testing, and placing the sample in an oven at 80 ℃ for 4 hours; selecting 1000V for the voltage in the test;
hydrolysis resistance: after being placed in an environment with 70 ℃ and 95% humidity for 14 days, the tensile strength (b) is tested according to GB/T528, and the retention rate (a) of the tensile strength is calculated, wherein a is b/b0 multiplied by 100%;
the above test data are shown in table 1.
TABLE 1
From the data, the tire prepared from the polyurethane solid tire material obtained by the invention has excellent antistatic property, thermal stability and hydrolysis resistance.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is illustrative and explanatory only and is not intended to be exhaustive or to limit the invention to the precise embodiments described, and various modifications, additions, and substitutions may be made by those skilled in the art without departing from the scope of the invention or exceeding the scope of the claims.
Claims (8)
1. The anti-static polyurethane solid tire material is characterized in that: the feed comprises the following raw materials in parts by weight: 100-170 parts of polyether polyol, 140-250 parts of polyester polyol, 15-23 parts of chain extender, 18-40 parts of isocyanate, 4-8.5 parts of cross-linking agent, 5-18 parts of modified conductive carbon black, 8-20 parts of modified antistatic agent and 25-55 parts of reactive flame retardant;
the modified antistatic agent is prepared by the following steps:
heating and stirring the antistatic agent and anhydrous chloroform until the antistatic agent is completely dissolved, controlling the temperature to be not more than 55 ℃ in the stirring process, stopping heating, cooling to room temperature, dropwise adding FeCl3And (3) after the methanol solution is completely dripped, continuously stirring and reacting for 40-60min, and removing the solvent by rotary evaporation to obtain the modified antistatic agent.
2. The antistatic polyurethane solid tire material of claim 1, wherein: the antistatic agent, anhydrous chloroform and FeCl3The dosage ratio of the methanol is 20 g: 70-90 mL: 12 g: 60-80 mL.
3. The antistatic polyurethane solid tire material of claim 1, wherein: the antistatic agent is prepared by the following steps:
mixing modified polysiloxane and nitromethane, stirring until the modified polysiloxane is completely dissolved, then adding 1-bromon-hexane under the conditions of nitrogen and stirring, heating to 65 ℃, stirring for reacting for 24 hours, and carrying out post-treatment to obtain the antistatic agent.
4. The antistatic polyurethane solid tire material of claim 3, wherein: the dosage ratio of the modified polysiloxane, the nitromethane and the 1-bromon-hexane is 10-14 g: 100 and 200 mL: 0.7-1.8 g.
5. The antistatic polyurethane solid tire material of claim 3, wherein: the modified polysiloxane alkane is prepared by the following steps:
uniformly mixing 4-vinylpyridine, 1,3, 3-tetramethylsilane and toluene, heating to 93 ℃ under the protection of nitrogen, adding a chloroplatinic acid isopropanol solution, reacting for 5 hours, and performing post-treatment to obtain the modified polysiloxane.
6. The antistatic polyurethane solid tire material of claim 5, wherein: the mol ratio of the 4-vinylpyridine to the 1,1,3, 3-tetramethylsilane is 1: 1.
7. the antistatic polyurethane solid tire material of claim 1, wherein: the reactive flame retardant is prepared by the following steps:
mixing iron powder, ethanol and deionized water, adjusting the pH value of the solution to 4-5, stirring and boiling for 30-40min, stopping heating, cooling to room temperature, adding DOPO derivative under stirring, heating to 80 ℃, reacting for 4h, and performing post-treatment to obtain the reactive flame retardant.
8. The antistatic polyurethane solid tire material of claim 7, wherein: the DOPO derivative is prepared by the following steps:
mixing 5-nitro-2-chlorotrifluoromethane, DOPO-BQ, potassium carbonate and DMF, heating to 130 ℃, stirring for reaction for 24 hours, cooling, performing suction filtration, performing rotary evaporation and concentration on the filtrate, and performing vacuum drying to obtain the DOPO derivative.
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