CN114149615A - Highly dispersible metal acrylate composition, method for producing the same, and resin composition containing the same - Google Patents
Highly dispersible metal acrylate composition, method for producing the same, and resin composition containing the same Download PDFInfo
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- CN114149615A CN114149615A CN202010919407.XA CN202010919407A CN114149615A CN 114149615 A CN114149615 A CN 114149615A CN 202010919407 A CN202010919407 A CN 202010919407A CN 114149615 A CN114149615 A CN 114149615A
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- Prior art keywords
- ethylene
- metal
- metal acrylate
- acrylate composition
- composition
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- 239000000203 mixture Substances 0.000 title claims abstract description 190
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 128
- 239000002184 metal Substances 0.000 title claims abstract description 128
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 96
- 239000011342 resin composition Substances 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 104
- 239000000843 powder Substances 0.000 claims abstract description 91
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 52
- 229910002804 graphite Inorganic materials 0.000 claims abstract description 25
- 239000010439 graphite Substances 0.000 claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 229920001577 copolymer Polymers 0.000 claims description 43
- 229920001971 elastomer Polymers 0.000 claims description 42
- 239000000806 elastomer Substances 0.000 claims description 37
- -1 polyethylene, ethylene Polymers 0.000 claims description 35
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 32
- 239000005977 Ethylene Substances 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 229920000098 polyolefin Polymers 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 229920006124 polyolefin elastomer Polymers 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 229910044991 metal oxide Inorganic materials 0.000 claims description 8
- 150000004706 metal oxides Chemical class 0.000 claims description 8
- 229920002943 EPDM rubber Polymers 0.000 claims description 7
- 239000005062 Polybutadiene Substances 0.000 claims description 7
- 239000012454 non-polar solvent Substances 0.000 claims description 7
- 150000001451 organic peroxides Chemical class 0.000 claims description 7
- 229920002857 polybutadiene Polymers 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000004604 Blowing Agent Substances 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 229920001038 ethylene copolymer Polymers 0.000 claims description 6
- 239000004711 α-olefin Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 4
- 239000012933 diacyl peroxide Substances 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 claims description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 3
- 244000043261 Hevea brasiliensis Species 0.000 claims description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 3
- 239000004566 building material Substances 0.000 claims description 3
- 229920005549 butyl rubber Polymers 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229920003049 isoprene rubber Polymers 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229920003052 natural elastomer Polymers 0.000 claims description 3
- 229920001194 natural rubber Polymers 0.000 claims description 3
- 150000002832 nitroso derivatives Chemical class 0.000 claims description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 claims description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 claims description 2
- 229910001425 magnesium ion Inorganic materials 0.000 claims description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 14
- 238000004132 cross linking Methods 0.000 abstract description 7
- 239000012752 auxiliary agent Substances 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract description 4
- 239000005022 packaging material Substances 0.000 abstract description 2
- 238000005034 decoration Methods 0.000 abstract 2
- 239000011521 glass Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 72
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 69
- 238000012360 testing method Methods 0.000 description 51
- 239000002245 particle Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 22
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 238000007906 compression Methods 0.000 description 15
- 230000006835 compression Effects 0.000 description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- PRIFGVOVRHAALC-UHFFFAOYSA-N tert-butyl 3,3-dimethylbutaneperoxoate Chemical compound CC(C)(C)CC(=O)OOC(C)(C)C PRIFGVOVRHAALC-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 12
- 239000012043 crude product Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000011787 zinc oxide Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 229920002545 silicone oil Polymers 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000004088 foaming agent Substances 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- BMFMTNROJASFBW-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfinyl)acetic acid Chemical compound OC(=O)CS(=O)CC1=CC=CO1 BMFMTNROJASFBW-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 4
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000005054 agglomeration Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 230000002087 whitening effect Effects 0.000 description 3
- PIMBTRGLTHJJRV-UHFFFAOYSA-L zinc;2-methylprop-2-enoate Chemical compound [Zn+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O PIMBTRGLTHJJRV-UHFFFAOYSA-L 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 2
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- 239000004156 Azodicarbonamide Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 235000019399 azodicarbonamide Nutrition 0.000 description 2
- TXTCTCUXLQYGLA-UHFFFAOYSA-L calcium;prop-2-enoate Chemical compound [Ca+2].[O-]C(=O)C=C.[O-]C(=O)C=C TXTCTCUXLQYGLA-UHFFFAOYSA-L 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000013211 curve analysis Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- QTBYJJMYUHJEAU-UHFFFAOYSA-K gold(3+) prop-2-enoate Chemical compound [Au+3].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C QTBYJJMYUHJEAU-UHFFFAOYSA-K 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- DWLAVVBOGOXHNH-UHFFFAOYSA-L magnesium;prop-2-enoate Chemical compound [Mg+2].[O-]C(=O)C=C.[O-]C(=O)C=C DWLAVVBOGOXHNH-UHFFFAOYSA-L 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 2
- OIQNWJHRBIPDFR-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate 2-tert-butylbenzenecarboperoxoic acid Chemical compound C(C)(C)(C)C1=C(C(=O)OO)C=CC=C1.C(C1=CC=CC=C1)(=O)OOC(C)(C)C OIQNWJHRBIPDFR-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- SZHMINOUAKXKQB-UHFFFAOYSA-N (2-tert-butylcyclohexyl) (2-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound CC(C)(C)C1CCCCC1OC(=O)OOC(=O)OC1C(C(C)(C)C)CCCC1 SZHMINOUAKXKQB-UHFFFAOYSA-N 0.000 description 1
- AGKBXKFWMQLFGZ-UHFFFAOYSA-N (4-methylbenzoyl) 4-methylbenzenecarboperoxoate Chemical compound C1=CC(C)=CC=C1C(=O)OOC(=O)C1=CC=C(C)C=C1 AGKBXKFWMQLFGZ-UHFFFAOYSA-N 0.000 description 1
- CJVROGOPKLYNSX-UHFFFAOYSA-N (4-tert-butylcyclohexyl) carboxyoxy carbonate Chemical compound CC(C)(C)C1CCC(OC(=O)OOC(O)=O)CC1 CJVROGOPKLYNSX-UHFFFAOYSA-N 0.000 description 1
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 1
- ISNKSXRJJVWFIL-UHFFFAOYSA-N (sulfonylamino)amine Chemical class NN=S(=O)=O ISNKSXRJJVWFIL-UHFFFAOYSA-N 0.000 description 1
- RQHGZNBWBKINOY-PLNGDYQASA-N (z)-4-tert-butylperoxy-4-oxobut-2-enoic acid Chemical compound CC(C)(C)OOC(=O)\C=C/C(O)=O RQHGZNBWBKINOY-PLNGDYQASA-N 0.000 description 1
- KHAPTVFTVICAJJ-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane 3-tert-butylperoxy-1,1,5-trimethylcyclohexane Chemical compound C(C)(C)(C)OOC1(CC(CC(C1)C)(C)C)OOC(C)(C)C.C(C)(C)(C)OOC1CC(CC(C1)C)(C)C KHAPTVFTVICAJJ-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- CUOSYYRDANYHTL-UHFFFAOYSA-N 1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid;sodium Chemical class [Na].CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC CUOSYYRDANYHTL-UHFFFAOYSA-N 0.000 description 1
- KEFKGTYAXAQBCF-UHFFFAOYSA-N 1-methyl-4-[(4-methylphenyl)methylperoxymethyl]benzene Chemical compound C1=CC(C)=CC=C1COOCC1=CC=C(C)C=C1 KEFKGTYAXAQBCF-UHFFFAOYSA-N 0.000 description 1
- CQSQUYVFNGIECQ-UHFFFAOYSA-N 1-n,4-n-dimethyl-1-n,4-n-dinitrosobenzene-1,4-dicarboxamide Chemical compound O=NN(C)C(=O)C1=CC=C(C(=O)N(C)N=O)C=C1 CQSQUYVFNGIECQ-UHFFFAOYSA-N 0.000 description 1
- IHJGEUZIBARDOP-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound C(C)(C)(C)OOC(C)(CC)OOC(C)(C)C.C(C)(C)(C)OOC(C)(CC)OOC(C)(C)C IHJGEUZIBARDOP-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- HQLWSPAOVXYSSG-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C.CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C HQLWSPAOVXYSSG-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- HTCRKQHJUYBQTK-UHFFFAOYSA-N 2-ethylhexyl 2-methylbutan-2-yloxy carbonate Chemical compound CCCCC(CC)COC(=O)OOC(C)(C)CC HTCRKQHJUYBQTK-UHFFFAOYSA-N 0.000 description 1
- SKVOYPCECYQZAI-UHFFFAOYSA-N 2-ethylhexyl 2-methylbutan-2-ylperoxy carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)CC SKVOYPCECYQZAI-UHFFFAOYSA-N 0.000 description 1
- JXGGWQKLAMYJLK-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CC1=C(C(=CC(=C1)CSCCCCCCCC)CSCCCCCCCC)O.CC1=C(C(=CC(=C1)CSCCCCCCCC)CSCCCCCCCC)O JXGGWQKLAMYJLK-UHFFFAOYSA-N 0.000 description 1
- ZZKRLIVGACQJAB-UHFFFAOYSA-N 2-methylidenehexanoic acid Chemical compound CCCCC(=C)C(O)=O.CCCCC(=C)C(O)=O ZZKRLIVGACQJAB-UHFFFAOYSA-N 0.000 description 1
- WPIYAXQPRQYXCN-UHFFFAOYSA-N 3,3,5-trimethylhexanoyl 3,3,5-trimethylhexaneperoxoate Chemical compound CC(C)CC(C)(C)CC(=O)OOC(=O)CC(C)(C)CC(C)C WPIYAXQPRQYXCN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- FZACIZFMQSYWOM-UHFFFAOYSA-N C(C)(C)(C)C(C(=O)OO)CCCCC(C)(C)C.C(CCCCCC(C)(C)C)(=O)OOC(C)(C)C Chemical compound C(C)(C)(C)C(C(=O)OO)CCCCC(C)(C)C.C(CCCCCC(C)(C)C)(=O)OOC(C)(C)C FZACIZFMQSYWOM-UHFFFAOYSA-N 0.000 description 1
- NNHDHXUFNNAHNN-UHFFFAOYSA-N C(C)(C)(C)OOC(C)(C)C1=C(C=CC=C1)C(C)(C)OOC(C)(C)C.C(C)(C)(C)OOC(C)(C)C1=C(C=CC=C1)C(C)(C)OOC(C)(C)C Chemical compound C(C)(C)(C)OOC(C)(C)C1=C(C=CC=C1)C(C)(C)OOC(C)(C)C.C(C)(C)(C)OOC(C)(C)C1=C(C=CC=C1)C(C)(C)OOC(C)(C)C NNHDHXUFNNAHNN-UHFFFAOYSA-N 0.000 description 1
- YQVMGICKJZMQFT-UHFFFAOYSA-N C(CC)C(C(=O)O)=C.C(CC)C(C(=O)O)=C Chemical compound C(CC)C(C(=O)O)=C.C(CC)C(C(=O)O)=C YQVMGICKJZMQFT-UHFFFAOYSA-N 0.000 description 1
- ZIFXZHWDFOUOGX-UHFFFAOYSA-N C(CCCCC)C(C(=O)O)=C.C(CCCCC)C(C(=O)O)=C Chemical compound C(CCCCC)C(C(=O)O)=C.C(CCCCC)C(C(=O)O)=C ZIFXZHWDFOUOGX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- MWRWFPQBGSZWNV-UHFFFAOYSA-N Dinitrosopentamethylenetetramine Chemical compound C1N2CN(N=O)CN1CN(N=O)C2 MWRWFPQBGSZWNV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- VBKRXPZQAMBGCG-UHFFFAOYSA-N a805811 Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VBKRXPZQAMBGCG-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000000445 field-emission scanning electron microscopy Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000013101 initial test Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- ALIFPGGMJDWMJH-UHFFFAOYSA-N n-phenyldiazenylaniline Chemical compound C=1C=CC=CC=1NN=NC1=CC=CC=C1 ALIFPGGMJDWMJH-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000003921 particle size analysis Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000011359 shock absorbing material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OQXKWNNTBOKHCC-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate 2,2,4,4-tetramethylpentaneperoxoic acid Chemical compound C(C)(C)(C)CC(C(=O)OO)(C)C.C(C(C)(C)C)(=O)OOC(C)(C)C OQXKWNNTBOKHCC-UHFFFAOYSA-N 0.000 description 1
- YUMFXXAAFYXASW-UHFFFAOYSA-N tert-butyl ethaneperoxoate 3,3-dimethylbutaneperoxoic acid Chemical compound C(C)(C)(C)CC(=O)OO.C(C)(C)(C)OOC(C)=O YUMFXXAAFYXASW-UHFFFAOYSA-N 0.000 description 1
- GSECCTDWEGTEBD-UHFFFAOYSA-N tert-butylperoxycyclohexane Chemical compound CC(C)(C)OOC1CCCCC1 GSECCTDWEGTEBD-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
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- C08J9/0023—Use of organic additives containing oxygen
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0095—Mixtures of at least two compounding ingredients belonging to different one-dot groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
- C08J9/10—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond
- C08J9/102—Azo-compounds
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- C08J2203/00—Foams characterized by the expanding agent
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Abstract
The invention discloses a high-dispersity metal acrylate composition, a preparation method thereof and a resin composition containing the same. Specifically, the invention aims to provide a high-dispersity metal acrylate composition which comprises a compound shown as a formula (I) (wherein M is2+And R1 are as defined in the specification), and contains a specific content of graphene, flake graphite, or a combination thereof as a heat conductive powder, thereby having excellent stability and dispersibility, and having advantages of being less likely to adhere to a metal surface and being easily blended in a resin. In addition, the cross-linking auxiliary agent can be used in the resin composition to improve the mechanical strength of the finished product, and simultaneously, the foamed finished product has good cell uniformity, so that the cross-linking auxiliary agent can be widely applied to interior and exterior decoration materials, civil article materials, interior decoration materials for vehicles, door and window and glass frame buffer materials, packaging materials, sports pad materials, shoe materials and the like.
Description
Technical Field
The present invention relates to a metal salt applied to a resin, and more particularly, to a metal acrylate composition having high dispersibility, a method for manufacturing the same, and a resin composition comprising the same.
Background
The metal acrylate is a conventional metal-type crosslinking aid, can be used in combination with a crosslinking agent as a compounding agent in vulcanization of a rubber composition, can also be used as a modifier in synthetic resins, and has the functions of improving the hardness and compression rebound of materials, increasing the affinity between the materials and metals, improving the compatibility between the materials, and improving the mechanical strength, stretchability, heat resistance, wear resistance, solvent resistance, tear strength and metal adhesion of plasticized materials, so that the metal acrylate is widely applied and added to various plasticized molded products such as golf balls, rollers, sealing strips, cables, belts, building materials and the like.
The metal acrylate structure is shown by the following formula:
wherein M is2+Is a divalent metal ion, and R is a hydrogen radical (-H) or a saturated alkyl radical.
Common metal acrylates such as Zinc Diacrylate (ZDA), calcium diacrylate (calcium diacrylate), magnesium diacrylate (magnesium diacrylate). Commercially available related products such as Dymalink 633, Dymalink 634, Dymalink 705 and Dymalink 706 from kreviley (CRAY VALLEY) france; K-CURE 339, K-CURE 439, K-CURE 633 and K-CURE 634 of Sanwa corporation (SUNKO INK) of Taiwan; and ZN-DA 90 and ZN-DA 100 from Japan catalyst Co. The production method is disclosed in the patent contents of Taiwan patent publication No. 530062, Japanese patent publication No. Sho 58-14416, Japanese patent publication No. Hei 4-10463, Japanese patent publication No. 4041175, Japanese patent publication No. 4286018, Japanese patent publication No. 4398157, US patent publication No. 5789616, US patent publication No. 6278010, US patent publication No. 7217829, etc.
However, metal acrylates tend to self-polymerize at high temperatures and agglomerate at high temperatures with moisture, and in addition, when the metal acrylates are left for a long time or stacked and pressed heavily, the problem of agglomeration due to aggregation and compaction is more pronounced, especially for metal acrylates with smaller particle sizes.
Generally, after the metal acrylate is agglomerated, it is not easy to knead and disperse in the rubber, and during the kneading, the agglomerated metal acrylate is easy to generate self-polymerization due to heat generated by friction, generates viscosity, and further adheres more metal acrylate; in addition, the metal acrylate is also easy to stick to the metal surface of the equipment, which causes plate-out and is difficult to remove, and once peeled off, the surface of the rubber product is flawed or flawed, which affects the quality and appearance.
The difficulty in dispersing the metal acrylate may further affect the preparation of the foamed elastomer, mainly because the uneven dispersion of the metal acrylate may cause uneven bridge density, resulting in uneven cell size, uneven cell wall thickness, air inclusion, foam breaking and other phenomena of the prepared foamed elastomer, and may also result in poor appearance and insufficient mechanical properties such as tear strength.
Regarding the above problems, U.S. patent publication No. 6720364 and taiwan patent publication No. 574296 disclose that a foamed polyolefin composition containing zinc diacrylate or zinc dimethacrylate is prepared by a secondary pressing process, which can avoid the surface of the foamed molded product from breaking bubbles to meet the physical property requirement, however, the secondary pressing process is time-consuming, labor-consuming and increases the manufacturing cost.
It is mentioned that the storage stability of the metal acrylate can be improved by using polytetrafluoroethylene wax or polytetrafluoroethylene-modified polyethylene wax as a dispersant according to the disclosure of taiwan patent publication No. 648097 and U.S. patent publication No. 10550259B 2. In addition, according to the content of taiwan patent publication No. 647262B, the metal acrylate is applied to a polyolefin elastomer composition to obtain a foamed molded article with high reverse elasticity and low compression set without secondary pressing, however, the above patent documents do not mention how to avoid the problem of metal acrylate adhering to the metal surface during transportation to cause precipitation, nor do they discuss the effect of the metal acrylate on the uniformity of cell dispersion of the foamed molded article.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, it is an object of the present invention to provide a highly dispersible metal acrylate composition which is less likely to stick to metal surfaces during transportation.
Another object of the present invention is to provide a highly dispersible metal acrylate composition which can be used as a crosslinking assistant in a resin composition to improve the mechanical strength of the final product and at the same time, can provide a foamed final product with good uniformity of cell dispersion.
To achieve the above object, the present invention provides a metal acrylate composition comprising:
a metal salt of monoacrylate represented by the formula (I);
in formula (I), M2+Is zinc ion, magnesium ion or calcium ion, R1 is hydrogen radical or saturated alkyl with 1-6 carbon atoms; and
the heat conducting powder is graphene, crystalline flake graphite or a combination thereof, and the content of the heat conducting powder is 0.3 to 25 weight percent based on the total weight of the metal acrylate composition.
The metal acrylate composition of the invention can improve the stability and the dispersibility by containing the metal acrylate and the graphene, the crystalline flake graphite or the combination thereof with specific content, is not easy to stick to the metal surface and easy to be mixed in resin in the transportation process besides being beneficial to long-time storage or transportation without caking, and simultaneously, the metal acrylate composition of the invention can further be applied to the resin composition to ensure that the finished product has better mechanical strength and the foamed finished product has better cell dispersion uniformity.
According to the present invention, the WI value of the hue of the aforementioned metal acrylate composition is greater than or equal to 20 and less than or equal to 70.
Preferably, the content of the heat conductive powder is 0.3 to 8 weight percent based on the total weight of the metal acrylate composition; further, the WI value of the hue of the metal acrylate composition is 30 or more and 70 or less.
More preferably, the content of the thermally conductive powder is 0.3 to 2 wt% based on the total weight of the metal acrylate composition. By controlling the content of the heat-conducting powder in the specific range and applying the heat-conducting powder in the resin composition, a finished product obtained after foaming can further have the effects of whitening, yellow light removal and fogging surface, and can provide very good appearance and texture; further, the WI value of the hue of the metal acrylate composition is 45 or more and 70 or less.
Preferably, the graphene comprises reduced graphene oxide (rGO) having a carbon content of 40% or more and 3 to 30 layers; the flake graphite (flake graphite) comprises flake graphite with a carbon content of more than 95% and a particle size D90 of 5-30 microns. More preferably, the graphene includes a thin layer reduced graphene oxide having a carbon content of 60% or more and a number of layers of 3 to 10 and an ash content of 0.1 to 2.5 wt%, and a multi-layer reduced graphene oxide having a carbon content of 60% or more and a number of layers of 10 to 20 and an ash content of 0.1 to 2.5 wt%; the flake graphite comprises flake graphite with carbon content of more than 98%, particle size D90 of 10-25 microns and ash content of 0.1-1 wt%.
The metal acrylate composition of the present invention may optionally contain additives such as, but not limited to, an antioxidant, a polymerization inhibitor, a heat resistant agent, a lubricant, a surfactant, or a combination thereof.
The invention also provides a preparation method of the metal acrylate composition, which comprises the following steps: step (a): reacting acrylic acid, divalent metal oxide and heat-conducting powder in a non-polar solvent at a temperature of 30-100 ℃ to obtain a first mixture; and a step (b): removing the solvent from the first mixture to obtain the metal acrylate composition; wherein the heat-conducting powder is graphene, crystalline flake graphite or a combination thereof, and the content of the heat-conducting powder is 0.3 to 25 weight percent based on the total weight of the metal acrylate composition.
Preferably, the step (a) further comprises the steps of: step (a 1): mixing the acrylic acid and the heat-conducting powder to obtain a second mixture; and step (a 2): reacting the second mixture and the divalent metal oxide in the non-polar solvent at a temperature of 30 ℃ to 100 ℃ to obtain the first mixture.
Preferably, the molar ratio of the acrylic acid and the divalent metal oxide is 1.4:1 to 2.1: 1. More preferably, the molar ratio of the acrylic acid and the divalent metal oxide is 1.85:1 to 2.05: 1.
In the above-mentioned production method, acrylic acid is applicable, for example: 2-acrylic acid (2-propenoic acid), 2-methacrylic acid (2-methylpropenoic acid), 2-ethacrylic acid (2-ethylpropenoic acid), 2-propylacrylic acid (2-propylpropenoic acid), 2-butylacrylic acid (2-butylpropenoic acid), 2-pentylacrylic acid (2-pentylpropenoic acid), 2-hexylacrylic acid (2-hexylpropenoic acid), but is not limited thereto.
In the above-mentioned production method, applicable divalent metal oxides are, for example: zinc oxide, magnesium oxide, calcium oxide, zinc hydroxide, magnesium hydroxide, or calcium hydroxide, but is not limited thereto.
In the preparation method, the graphene comprises reduced graphene oxide with carbon content of more than 40% and 3-30 layers; the flake graphite comprises flake graphite with carbon content of more than 95% and particle size D90 of 5-30 microns. Preferably, the graphene includes a thin layer reduced graphene oxide having a carbon content of 60% or more and a number of layers of 3 to 10 and an ash content of 0.1 to 2.5 wt%, and a multi-layer reduced graphene oxide having a carbon content of 60% or more and a number of layers of 10 to 20 and an ash content of 0.1 to 2.5 wt%; the flake graphite comprises flake graphite with carbon content of more than 98%, particle size D90 of 10-25 microns and ash content of 0.1-1 wt%.
In the above preparation method, the nonpolar solvent refers to a hydrocarbon-based solvent having a boiling point of 50 ℃ to 150 ℃ at normal pressure; non-polar solvents to which the present process is applicable may be, but are not limited to: benzene, toluene, xylene, cyclohexane, hexane, heptane or octane.
An additive may be optionally added in the above manufacturing method, and the applicable additive includes, but is not limited to, an antioxidant, a polymerization inhibitor, a heat resistant agent, a lubricant, a surfactant, or a combination thereof.
According to the present invention, the content of the aforementioned additive is 0.02 to 10% by weight based on the total weight of the metal acrylate composition.
According to the present invention, the addition of the antioxidant can inhibit or prevent oxidative destruction from occurring in the subsequent production of the elastomer, and can inhibit or prevent the reaction initiated by oxygen radicals, for example: quinoline-based antioxidants, amine-based antioxidants, phenol-based antioxidants, sulfur-based antioxidants, and the like, and specific illustrative examples include: the reaction product of N-phenylaniline with 2,4,4-trimethylpentene (product of N-phenylaniline reacted with 2,4,4-trimethylpentene, CAS No.68411-46-1), 2, 6-di-t-butyl-p-cresol (2, 6-di-t-butyl-4-methyl-phenol), 2'-methylene-bis (4-methyl-6-t-butylphenol) (2,2' -methyl-bis (6-t-butyl-4-methylphenol), 4, 6-di (octylthiomethyl) o-cresol (2-methyl-4,6-bis (octylthiomethyl) phenol), but not limited thereto, and the addition of polymerization inhibitors, such as monomethyl ether (monomethylhydroquinone), 2, 6-di-t-butyl-p-methylphenol (dimethylamine), 6-di-tert-butyl-4- (dimethylamino) phenol), 2,6, 6-tetramethylpiperidine oxide (2,2,6, 6-tetramethylpiperidine), but is not limited thereto; the addition of heat resistance agents can improve thermal stability, for example: fatty acid metal salts, but are not limited thereto; the addition of the lubricant can reduce the friction heat in the powder conveying process, such as: fatty acids, low molecular weight polyethylene, but are not limited thereto; the addition of surfactants can improve dispersibility, for example: polyoxyethylene alkyl ethers (polyoxyethylene alkyl ether), sorbitan fatty acid esters (polyoxyethylene fatty acid ester), polyoxyethylene sorbitan fatty acid esters (polyoxyethylene sorbitan fatty acid ester), silicone oils (silicone oil), sodium alkylbenzenesulfonates (sodium alkylbenzenesulfonates), and sodium dioctyl sulfosuccinates (sodium dioctyl sulfosuccinate), and the like, but are not limited thereto.
The invention also provides a resin composition, which comprises an unsaturated aliphatic polyolefin and the metal acrylate composition.
Preferably, the metal acrylate composition is used in an amount of 0.1 to 30 parts by weight based on 100 parts by weight of the unsaturated aliphatic polyolefin. More preferably, the metal acrylate composition is used in an amount of 0.1 to 5 parts by weight based on 100 parts by weight of the unsaturated aliphatic polyolefin.
Preferably, the unsaturated aliphatic polyolefin is selected from the group consisting of ethylene propylene diene monomer rubber (EPDM), Butadiene Rubber (BR), butyl rubber (IIR), Natural Rubber (NR), Isoprene Rubber (IR), and combinations thereof. More preferably, the unsaturated aliphatic polyolefin is selected from the group consisting of ethylene propylene diene monomer, butadiene rubber, and combinations thereof.
Preferably, the resin composition may further comprise a copolymer, an organic peroxide, a blowing agent, an auxiliary agent or a combination thereof.
Preferably, the applicable copolymer comprises an ethylene copolymer (ethylene copolymer), a polyolefin block copolymer (olefin block copolymer), or a combination thereof.
Preferably, the ethylene copolymer is selected from the group consisting of ethylene/vinyl acetate copolymer (ethylene/vinyl acetate copolymer), ethylene/octene copolymer (ethylene/octene copolymer), Polyethylene (PE), ethylene/alpha-olefin copolymer (ethylene/alpha-olefin copolymer), ethylene/alpha-olefin non-conjugated diene copolymer (ethylene/alpha-olefin non-conjugated diene copolymer), ethylene/acrylic acid copolymer (ethylene/acrylic copolymer), ethylene/methacrylic acid copolymer (ethylene/methyl acrylate copolymer), ethylene/methyl acrylate copolymer (ethylene/methyl acrylate copolymer), ethylene/methyl methacrylate copolymer (ethylene/methyl methacrylate copolymer), ethylene/ethyl acrylate copolymer (ethylene/ethyl acrylate copolymer), ethylene/vinyl acetate copolymer (ethylene/vinyl acetate copolymer), ethylene/vinyl acrylate copolymer (ethylene/vinyl acrylate copolymer), and ethylene/vinyl acrylate copolymer (ethylene/vinyl acrylate copolymer), Ethylene/ethyl methacrylate copolymer, ethylene/butyl acrylate copolymer, ethylene/butyl methacrylate copolymer, and combinations thereof. Even more preferably, the copolymer is selected from the group consisting of ethylene/vinyl acetate copolymers, ethylene/octene copolymers, polyolefin block copolymers, and combinations thereof.
In the resin composition, the weight ratio of the copolymer to the unsaturated aliphatic polyolefin is 1:3 to 3: 1.
Preferably, the applicable organic peroxides include: alkyl hydroperoxides (alkyl hydroperoxides), dialkyl hydroperoxides (dialkyl hydroperoxides), aromatic hydroperoxides (aromatic hydroperoxides), peroxyesters (perheaters), diperoxyketals (diperoxyketals), diacyl peroxides (diacyl peroxides), or peroxydicarbonates, but are not limited thereto.
More specifically, the alkyl hydroperoxide may be, but is not limited to: tert-butyl hydroperoxide (tert-butyl-hydroperoxide), tert-amyl hydroperoxide (tert-amyl-hydroperoxide) or 2,5-dimethyl-2, 5-bis (hydroperoxide) hexane (2,5-dimethyl-hexane-2, 5-hydroperoxide); the dialkyl hydroperoxide may be, but is not limited to: di-tert-butyl hydroperoxide (di-tert-butyl-hydroperoxide), di-tert-amyl hydroperoxide (di-tert-amyl-hydroperoxide), 2,5-dimethyl-2, 5-bis (tert-butylperoxy) hexane (2,5-bis (tert-butylperoxy) -2,5-dimethylhexane) or 2,5-dimethyl-2, 5-bis (tert-butylperoxy) hexyne (2,5-dimethyl-2,5-di (tert-butylperoxy) -hexyne-3); the aromatic hydroperoxide can be, but is not limited to: dicumyl peroxide (dicumyl peroxide), benzoyl peroxide (benzoyl peroxide), cumene hydroperoxide (cumene hydroperoxide), dicumyl hydroperoxide (diisopropybenzene hydroperoxide), tert-butyl peroxybenzoate (tert-butyl peroxybenzoate), di (tert-butylperoxyisopropyl) benzene (di (tert-butyl peroxyisopropyl) benzene), di (4-methylbenzoyl) peroxide (bis (4-methylbenzyl) peroxide); the peroxyacid ester may be, but is not limited to: tert-butyl peroxybenzoate (tert-butyl peroxybenzoate), tert-butyl peroxybenzoate (tert-amyl peroxybenzoate), tert-butyl peroxyacetate (tert-butyl peroxyacetate), tert-butyl peroxymaleate (tert-butyl monoperoxide), tert-butyl peroxypivalate (tert-butyl peroxypivalate), tert-butyl peroxyneodecanoate (tert-butyl peroxyneodecanoate), tert-butyl peroxyneodecanoate (tert-butyl peroxyhexanoate), tert-butyl peroxy2-ethylhexanoate (tert-butyl peroxy-2-ethylhexanoate), tert-butyl peroxyisobutyrate (tert-butyl peroxyisobutoxybutyrate), tert-butyl peroxyneoheptanoate (tert-butyl peroxyhexanoate), tert-butyl peroxyneohexanoate (tert-butyl peroxyhexanoate-3, 5-tert-butyl peroxyhexanoate (tert-butyl-5-tert-butyl peroxy5-hexanoate), tert-butyl peroxyneoheptanoate (tert-butyl peroxyneohexanoate), tert-butyl peroxyneohexanoate (tert-butyl peroxy5-tert-butyl 2, 5-hexanoate), tert-butyl peroxyneohexanoate (tert-butyl peroxyneohexanoate), tert-butyl peroxyneohexanoate (tert-2, 5-2-tert-butyl peroxyneohexanoate), tert-butyl peroxyneohexanoate (tert-2-butyl peroxyneohexanoate), tert-2-tert-butyl peroxyneohexanoate), tert-butyl peroxyneohexanoate (tert-2-butyl peroxyneohexanoate), tert-butyl peroxyneohexanoate), tert-butyl peroxyneohexanoate (tert-butyl peroxyneohexanoate), tert-2-butyl peroxyneohexanoate, tert-butyl peroxyneohexanoate, tert-2-tert-butyl peroxyneohexanoate, tert-2-butyl peroxyneohexanoate, 5-tert-butyl peroxyneohexanoate, tert-butyl peroxyneohexanoate, tert-butyl peroxyneohexanoate, tert-butyl peroxyneohexanoate, tert-butyl peroxytert-tert-butyl peroxyneohexanoate, tert-butyl peroxytert-tert-butyl peroxyneohexanoate, tert-butyl peroxyneohexanoate, tert-butyl peroxyneohexanoate, tert-butyl peroxyneohexanoate, tert-butyl peroxyneohexanoate, tert-butyl peroxyneo, T-amyl peroxy-2-ethylhexyl carbonate (tert-amyl peroxy-2-ethylhexyl carbonate) or 2,5-dimethyl-2, 5-bis (2-ethylhexanoylperoxy) hexane (2,5-dimethyl-2,5-di (2-ethylhexyloxy) hexane); the diperoxyketal can be, but is not limited to: 3,6,9-triethyl-3,6,9-trimethyl-1,4, 7-triperoxonane (3,6, 9-trietyl-3, 6,9-trimethyl-1,4, 7-trioxynonane), 1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane (1,1-bis (tert-butylperoxy) -3,3,5-trimethylcyclohexane), 1-bis (tert-butylperoxy) cyclohexane or 2, 2-bis (tert-butylperoxy) butane (2,2-di (tert-butylperoxy) butane); the diacyl peroxide can be, but is not limited to: benzoyl peroxide (benzoyl peroxide), bis- (3,3, 5-trimethylhexanoyl) peroxide (bis (3,5, 5-trimethy-1-oxyhexyl) peroxide) or dilauroyl peroxide (dilauroyl peroxide); the peroxydicarbonate may be, but is not limited to: bis (2-ethylhexyl) peroxydicarbonate, bis (2-tert-butylcyclohexyl) peroxydicarbonate, bist (4-tert-butyl-cyclohexyl) peroxydicarbonate, bistetradecyl peroxydicarbonate, or dicetyl peroxydicarbonate.
Preferably, applicable blowing agents include: azo compounds, nitroso compounds or sulfonyl hydrazines, wherein the azo compounds can be azodicarbonamide, azodicarboxylic acid amide, azodiisobutyronitrile, diisopropyl azodicarboxylate, diethyl azodicarboxylate, diazoaminobenzene or barium azodicarboxylate; the nitroso compound can be N, N ' -dinitrosopentamethylenetetramine or N, N ' -dimethyl-N, N ' -dinitrosoterephthalamide; the sulfonyl hydrazide compound may be 4,4 ' -disulfonyl hydrazide diphenyl ether, p-benzenesulfonyl hydrazide, 3 ' -disulfonyl hydrazide diphenyl sulfone, 4 ' -diphenyl disulfonyl hydrazide, 1, 3-benzenesulfonyl hydrazide, 1, 4-benzenesulfonyl hydrazide, but is not limited thereto.
According to the present invention, suitable auxiliaries include fatty acids having 12 to 20 carbon atoms, fatty acid metal salts (e.g., zinc stearate, calcium stearate, barium stearate, etc.), polyethylene wax, zinc oxide, urea, talc, calcium carbonate, titanium dioxide, kaolin, carbon black, coloring materials, stabilizers, auxiliary crosslinking aids containing a vinyl group (e.g., triallyl cyanurate, triallyl isocyanurate, divinylbenzene, triallyl phosphate), or combinations thereof, but are not limited thereto.
The invention also provides a polyolefin elastomer prepared from the resin composition. Specifically, the polyolefin elastomer can be produced by a conventional molding process, such as hot press molding, injection molding, or extrusion molding, but is not limited thereto.
Preferably, the polyolefin elastomer has a maximum tensile strength of greater than or equal to 110kg/cm2And less than or equal to 160kg/cm2. More preferably, the polyolefin elastomer has a maximum tensile strength of greater than or equal to 115kg/cm2And is less than or equal to 140kg/cm2。
Preferably, the polyolefin elastomer has a tear strength of greater than or equal to 25kg/cm and less than or equal to 50 kg/cm. More preferably, the polyolefin elastomer has a tear strength of greater than or equal to 30kg/cm and less than or equal to 45 kg/cm.
Preferably, the polyolefin elastomer has a compression set of greater than or equal to 10% and less than or equal to 30%.
The invention also provides a foaming elastomer prepared from the resin composition. Specifically, the foamed elastomer can be produced by a conventional foaming method, for example, but not limited to, compression molding, in-mold foaming, or injection foaming.
Preferably, the foamed elastomer has a maximum tensile strength of greater than or equal to 10kg/cm2And less than or equal to 25kg/cm2. More preferably, the foamed elastomer has a maximum tensile strength greater than or equal to 17kg/cm2And less than or equal to 25kg/cm2。
Preferably, the tear strength of the foamed elastomer is greater than or equal to 5kg/cm and less than or equal to 15 kg/cm. More preferably, the tear strength of the foamed elastomer is greater than or equal to 9.7kg/cm and less than or equal to 15 kg/cm.
Preferably, the foamed elastomer has a compression set of greater than or equal to 10% and less than or equal to 40%. More preferably, the foamed elastomer has a compression set of greater than or equal to 10% and less than or equal to 35%.
Preferably, the foamed elastomer has a hue WI value of greater than or equal to 20 and less than or equal to 70, a YI value of greater than or equal to-2 and less than or equal to 16, and a L value of greater than or equal to 45 and less than or equal to 85. More preferably, the foamed elastomer has a hue WI value of 40 or more and 70 or less, a YI value of 1 or more and 11 or less, and an L value of 70 or more and 85 or less.
According to the present invention, the foamed elastomer has good uniformity of cell dispersion and mechanical strength, and thus has a wide range of applications, such as building materials, vehicle materials, cushioning materials, shock-absorbing materials, packaging materials, sports mat materials, or footwear materials, and the like.
In the specification, a range represented by "a small value to a large value" means a range from greater than or equal to the small value to less than or equal to the large value, if not specifically indicated. For example, "0.3 weight percent to 25 weight percent" means that the range is "greater than or equal to 0.3 weight percent and less than or equal to 25 weight percent".
Drawings
Fig. 1A is a field emission scanning electron microscope photograph of example 2.
Fig. 1B is a field emission scanning electron microscope photograph of comparative example 1.
Fig. 2A to 2C are scanning electron micrographs of the foamed elastomer of example 12A in the field emission type at different positions above, in the middle, and below.
Fig. 2D to 2F are scanning electron micrographs of the foamed elastomer of comparative example 3A of field emission type at different positions above, in the middle, and below.
Detailed Description
The following describes embodiments of the present invention by way of example of a metal acrylate composition and a resin composition containing the same; those skilled in the art can readily appreciate from the disclosure of the present invention that the advantages and utilities of the present invention may be realized and attained without departing from the spirit and scope of the present invention as defined by the appended claims.
Metal acrylate composition
The characteristics of the metal acrylate composition of each example are shown in the description by the physical and chemical properties such as the effective zinc acrylate content, the heat conductive powder content, the ash content (ash), the hue, and the particle diameter. Each physicochemical property was obtained as described below.
1. Effective content of zinc acrylate: the double bond content was analyzed by redox titration to calculate the effective [ zinc acrylate salt ] weight percentage of the sample (unit:%).
2. Ash content: finely weighing 1 g of sample (initial weight W0), placing the sample into a high-temperature furnace, heating to 600 +/-25 ℃ for 3 hours, taking out and observing the color of the powder, placing the sample into the high-temperature furnace again, heating to 800 +/-25 ℃ and then keeping the temperature for 2 hours, confirming that the carbon is completely consumed, taking out and placing the residue in a drying oven when the residue is grey white, cooling to room temperature and weighing (residual weight W1); and then calculating the ash content value according to the following formula: [ (W0-W1)/W0] times 100% (unit:%).
3. Content of heat conductive powder: the content of the heat-conducting powder refers to the content of graphene, crystalline flake graphite or a combination thereof in the metal acrylate composition, namely the weight of the graphene, the crystalline flake graphite or the combination thereof is divided by the total weight of the actually obtained metal acrylate (unit:%).
4. Hue: selecting HunterLab
And the EZ color difference meter measures the whiteness and the yellowness of the samples, and each sample is measured for three times to obtain the average whiteness (WI value) and the average yellowness (YI value).
5. Particle size: selecting Beckman
LS 13320/ISO 13320-1 model laser particle size analyzer, using a micromodule for analysis. Weighing samples (the sampling amount of the heat-conducting powder is2 mg; the sampling amount of the metal acrylate composition is 0.15 g), adding ethanol, dispersing to 100 ml, oscillating for 1 minute by ultrasonic waves, injecting into a container of a micromodule until the shielding rate reaches 10%, starting analysis, recording the particle size (D90) of 90% of particles and the average particle size (D50) of the particles, testing each sample for three times, averaging and counting by the Volume (Volume) (unit: micron).
Example 1
Graphene (5.83 g, obtained from taiwan anguojia corporation, with a carbon content of 99% or more, an ash content of 0.5 wt% or less, and 10 to 20 layers of multi-layer reduced graphene oxide) was selected as the heat conductive powder, and was uniformly mixed with acrylic acid (1048 g, 14.55 mol, obtained from taiwan plastics industry ltd, and containing 200 ± 20ppm of hydroquinone monomethyl ether) to obtain a second mixture.
A6L stainless steel reaction tank is selected, 2000 ml of toluene, 586.4 g (7.24 mol) of zinc oxide, 102.3 g (0.36 mol) of stearic acid and 4.8 g of nonionic surfactant (Sinopol 1807) are added into the stainless steel reaction tank, the mixture is stirred uniformly and then heated to 50 +/-5 ℃, and then the second mixture is added for reaction, the temperature is controlled between 50 ℃ and 80 ℃, and the stirring is continued for 2 hours to obtain a first mixture.
The first mixture is distilled under reduced pressure to remove about 129 ml of water generated in the reaction, toluene is recovered, the first mixture is continuously dried until the water content of the first mixture is lower than 2000ppm, a crude product is obtained after the first mixture is cooled to room temperature, and the crude product is placed into an airflow type superfine powder high-speed pulverizer (model number is RT-25) for being pulverized to obtain 1587 g of a powdery product, namely the zinc acrylate composition of the example 1. The zinc acrylate salt composition of example 1 was characterized in the manner described above to give an effective zinc acrylate content: 92.3 percent; ash content value: 36.7 percent; particle size: d50 was 6.42 microns, D90 was 21.0 microns; hue: WI 65.5, YI-1.8; content of heat conductive powder: 0.367 percent.
Example 2
This example generally employs the preparation method described in the foregoing example 1 to prepare the zinc acrylate composition, except that: in example 2, 12.19 g of graphene (a multilayer reduced graphene oxide having a carbon content of 99% or more, an ash content of 0.5 wt% or less, and 10 to 20 layers obtained from taiwan anguong) is selected as the thermal conductive powder, and 1577 g of a powdery product, that is, the zinc acrylate salt composition of example 2, is finally obtained. The zinc acrylate salt composition of example 2 was characterized in the manner described above to give an effective zinc acrylate content: 91.2 percent; ash content value: 36.8 percent; particle size: d50 was 5.66 microns, D90 was 17.9 microns; hue: WI is 55.0, YI is-2.0; content of heat conductive powder: 0.773 percent.
Example 3
This example generally employs the preparation method described in the foregoing example 1 to prepare the zinc acrylate composition, except that: in example 3, 24.57 g of graphene (a multilayer reduced graphene oxide having a carbon content of 99% or more, an ash content of 0.5 wt% or less, and 10 to 20 layers obtained from taiwan anguong) is selected as the thermal conductive powder, and 1600 g of a powder product, that is, the zinc acrylate salt composition of example 3, is finally obtained. The zinc acrylate salt composition of example 3 was characterized in the manner described above to give an effective zinc acrylate content: 91.8 percent; ash content value: 36.8 percent; particle size: d50 was 7.41 microns, D90 was 20.8 microns; hue: WI is 50.8, YI is-2.5; content of heat conductive powder: 1.54 percent.
Example 4
This example generally employs the preparation method described in the foregoing example 1 to prepare the zinc acrylate composition, except that: in example 4, 32.92 g of graphene (a multilayer reduced graphene oxide having a carbon content of 99% or more, an ash content of 0.5 wt% or less, and 10 to 20 layers obtained from taiwan anguong) is selected as the thermal conductive powder, and 1605 g of a powder product, that is, the acrylic zinc salt composition of example 4, is finally obtained. The zinc acrylate salt composition of example 4 was characterized in the manner described above to give an effective zinc acrylate content: 90.4 percent; ash content value: 36.2 percent; particle size: d50 was 7.47 microns, D90 was 22.6 microns; hue: WI 49.6, YI-3.0; content of heat conductive powder: 2.05 percent.
Example 5
This example generally employs the preparation method described in the foregoing example 1 to prepare the zinc acrylate composition, except that: in example 5, 139.3 g of graphene (a multilayer reduced graphene oxide obtained from taiwan angungqiang, ltd., having a carbon content of 99% or more, an ash content of 0.5 wt% or less, and 10 to 20 layers) is selected as the heat conductive powder, and 1752 g of a powdery product, that is, the zinc acrylate salt composition of example 5, is finally obtained. The zinc acrylate salt composition of example 5 was characterized in the manner described above to give an effective zinc acrylate content: 86.9 percent; ash content value: 36.8 percent; particle size: 8.43 microns for D50, 20.7 microns for D90; hue: WI 33.0, YI-2.9; content of heat conductive powder: 7.95 percent.
Example 6
Selecting 5.83 g of graphene (purchased from taiwan angungtonics, with a carbon content of 60% to 80%, an ash content of less than or equal to 2.5 wt%, and 3 to 10 layers of thin-layer reduced graphene oxide) as heat-conducting powder, placing the heat-conducting powder into a 6-liter stainless steel reaction tank, simultaneously adding 2000 ml of toluene, 1048 g (14.55 mol) of acrylic acid, 586.4 g (7.24 mol) of zinc oxide, 102.3 g (0.36 mol) of stearic acid and 4.8 g of silicone oil, uniformly stirring, heating to 50 +/-5 ℃ for reaction, controlling the temperature between 50 ℃ and 80 ℃ in the reaction process, and continuously stirring for 2 hours to obtain a first mixture.
The first mixture was distilled under reduced pressure to remove about 129 ml of water produced by the reaction while recovering toluene, followed by continuous drying until the water content of the first mixture was less than 2000ppm, cooling to room temperature to obtain a crude product, and then the crude product was disintegrated in an air-flow type ultra-fine powder high-speed disintegrator (model RT-25) to obtain 1587 g of a powdery product, which was the zinc acrylate salt composition of example 6. The zinc acrylate salt composition of example 6 was characterized in the manner described above to give an effective zinc acrylate content: 92.3 percent; ash content value: 36.7 percent; particle size: d50 was 7.85 microns, D90 was 20.3 microns; hue: WI 59.4, YI-1.3; content of heat conductive powder: 0.367 percent.
Example 7
This example generally employs the preparation method described in the aforementioned example 6 to prepare the zinc acrylate composition, except that: in example 7, 12.19 g of graphene (a multilayer reduced graphene oxide having a carbon content of 99% or more, an ash content of 0.5 wt% or less, and 10 to 20 layers obtained from taiwan anguong) was selected as the thermal conductive powder, and 1624 g of a powder product was finally obtained, which was the zinc acrylate salt composition of example 7. The zinc acrylate salt composition of example 7 was characterized in the manner described above to give an effective zinc acrylate content: 91.65 percent; ash content value: 37.2 percent; particle size: d50 was 10.1 microns, D90 was 22.7 microns; hue: WI of 64.46, YI of-2.37; content of heat conductive powder: 0.751%.
Example 8
This example generally employs the preparation method described in the aforementioned example 6 to prepare the zinc acrylate composition, except that: in example 8, 12.19 g of flake graphite (obtained from Qingdao Tian and Dai, China, and containing 99.48% of carbon, 0.52% of ash, and 12.27 μm of particle size D90) was selected as the heat conductive powder, and 1626 g of a powder product, i.e., the zinc acrylate salt composition of example 8, was finally obtained. The zinc acrylate salt composition of example 8 was characterized in the manner described above to give an effective zinc acrylate content: 91.39 percent; ash content value: 37.13 percent; particle size: d50 was 18 microns, D90 was 29.8 microns; hue: WI is 62.12, YI is-2.29; content of heat conductive powder: 0.750 percent.
Example 9
This example generally employs the preparation method described in the aforementioned example 6 to prepare the zinc acrylate composition, except that: in example 9, 403.3 g of graphene (a multilayer reduced graphene oxide having a carbon content of 99% or more, an ash content of 0.5 wt% or less, and 10 to 20 layers obtained from taiwan anguong) was selected as the heat conductive powder, and 1936 g of a powdery product, that is, the zinc acrylate salt composition of example 9, was finally obtained. The zinc acrylate salt composition of example 9 was characterized in the manner described above to give an effective zinc acrylate content: 78.9 percent; ash content value: 34.6 percent; particle size: d50 was 8.64 microns, D90 was 23.9 microns; hue: WI 25.8, YI-2.75; content of heat conductive powder: 20.8 percent.
Example 10
13.3 g of graphene (purchased from taiwan angungsteng company, taiwan, with a carbon content of more than 99%, an ash content of less than or equal to 0.5 wt%, and 10 to 20 layers of multilayer reduced graphene oxide) is selected as heat-conducting powder to be placed in a 6-liter stainless steel reaction tank, 2000 ml of cyclohexane, 1252 g (14.55 mol) of methacrylic acid, 586.4 g (7.24 mol) of zinc oxide and 4.8 g of silicone oil are added into the heat-conducting powder, the mixture is stirred uniformly and then heated to 50 +/-5 ℃ for reaction, the temperature is controlled between 50 ℃ and 80 ℃ in the reaction process, and the mixture is continuously stirred for 2 hours to obtain a first mixture.
The first mixture was distilled under reduced pressure to remove about 129 ml of water produced by the reaction while recovering cyclohexane, followed by drying continuously until the water content of the first mixture was less than 2000ppm, cooling to room temperature to obtain a crude product, and then disintegrating the crude product in an air flow type ultra-fine powder high speed pulverizer (model RT-25) to obtain 1794 g of a powdery product, which was the zinc methacrylate composition of example 10. The zinc methacrylate salt composition of example 10 was characterized in the manner described above to give an effective zinc methacrylate content: 96.14 percent; ash content value: 31.65 percent; particle size: d50 was 8.7 microns, D90 was 24.6 microns; hue: WI is 49.28, YI is 4.14; content of heat conductive powder: 0.74 percent.
Comparative example 1
A6-liter stainless steel reaction tank is selected, 2000 ml of toluene, 1048 g (14.55 mol) of acrylic acid, 586.4 g (7.24 mol) of zinc oxide, 102.3 g (0.36 mol) of stearic acid and 4.8 g of silicone oil are added into the stainless steel reaction tank, the mixture is heated to 50 +/-5 ℃ after being uniformly stirred for reaction, the temperature is controlled between 50 ℃ and 80 ℃ in the reaction process, and the mixture is obtained after the continuous stirring for 2 hours.
The mixture was distilled under reduced pressure to remove about 129 ml of water produced by the reaction while recovering toluene, followed by continuous drying until the water content of the mixture was less than 2000ppm, cooling to room temperature to obtain a crude product, and then crushing the crude product in an air-flow type ultrafine high-speed pulverizer (model No. RT-25) to obtain 1581 g of a powdery product, which was the zinc acrylate salt composition of comparative example 1. The zinc acrylate salt composition of comparative example 1 was analyzed for its characteristics in the foregoing manner to obtain an effective zinc acrylate content: 91.6 percent; ash content value: 36.0 percent; particle size: d50 was 7.55 microns, D90 was 20.1 microns; hue: WI is 91.6, YI is-0.27.
Comparative example 2
A6-liter stainless steel reaction tank is selected, 2000 ml of cyclohexane, 1252 g (14.55 mol) of methacrylic acid, 586.4 g (7.24 mol) of zinc oxide and 4.8 g of silicone oil are added into the stainless steel reaction tank, the mixture is heated to 50 +/-5 ℃ after being uniformly stirred to react, the temperature is controlled between 50 ℃ and 80 ℃ in the reaction process, and the mixture is obtained after the mixture is continuously stirred for 2 hours.
The mixture was distilled under reduced pressure to remove about 129 ml of water produced by the reaction while recovering cyclohexane, followed by continuous drying until the water content of the mixture was less than 2000ppm, cooling to room temperature to obtain a crude product, and then crushing the crude product in an air-flow type ultrafine high-speed pulverizer (model No. RT-25) to obtain 1788.9 g of a powdery product, which was the zinc methacrylate composition of comparative example 2. The zinc methacrylate salt composition of comparative example 2 was analyzed for characteristics in the foregoing manner to obtain an effective zinc methacrylate content: 97.65 percent; ash content value: 32.36 percent; particle size: d50 was 7.8 microns, D90 was 37.9 microns; hue: WI is 89.85 and YI is 1.95.
As can be seen from the above processes of examples 1 to 10 and comparative examples 1 to 2, the main difference is whether graphene or flake graphite is added as a thermal conductive powder during the preparation process. The differences between the heat conductive powder of each example and the comparative example are shown in table 1.
Table 1: comparison of heat conductive powder contained in the zinc acrylate salt compositions of examples 1 to 10 and comparative examples 1 to 2.
To confirm that the metal acrylate composition of the present invention has better stability, dispersibility and anti-tack properties during storage or transportation, the following test example 1 simulates the effect of the metal acrylate composition after being stressed during storage or transportation; the morphology of the metal acrylate composition at the microscopic level was directly observed in test example 2 to evaluate the dispersibility; the procedure of conveying the metal acrylate composition in the feeder was simulated in test example 3 to observe the anti-sticking property to the metal equipment after the completion of the conveying. In addition, the thermal conductivity of the metal acrylate composition is presented in test example 4; the dispersibility of the heat conductive powder in the metal acrylate composition was observed by an optical microscope in test example 5.
Test example 1: metal acrylate composition weight pressure test
This test example was tested with the zinc acrylate salt compositions of examples 2, 8 and 9 and comparative example 1. The specific steps are that 3 bags of samples with the weight of 100 g are taken from the zinc acrylate salt compositions of different groups and are respectively placed in aluminum foil bags with the size of 10 centimeters multiplied by 10 centimeters, heat sealing is carried out after air in the aluminum foil bags is extruded out, and then a flange (flange) with the weight of 4 kilograms is placed on the aluminum foil bags after heat sealing and is placed in an oven with the temperature of 50 ℃, so that the conditions of weight pressure and temperature possibly applied to the metal acrylate salt composition in the process of transportation or storage can be simulated. The test time of test example 1 was measured in months, and the appearance states of the groups, which were determined to be one month, two months, and three months under stress, are shown in Table 2.
Table 2: appearance state of zinc acrylate salt compositions of examples 2, 8 and 9 and comparative example 1 at one month of stress, two months of stress and three months of stress.
As can be seen from the results in table 2, the heat conductive powder contained in the zinc acrylate salt composition of examples 2, 8 and 9 has better stability and dispersibility during storage or transportation than the comparative example 1 without the heat conductive powder, and the content of the heat conductive powder contained in the zinc acrylate salt composition of example 9 is the highest (20.8 wt%), so that the powder agglomeration phenomenon does not occur even in the appearance state after three months of the re-pressing.
Test example 2: observation of the form of the Metal acrylate composition
The shapes of the zinc acrylate salt compositions of example 2 and comparative example 1 were photographed at a magnification of 2000 times using a field-emission scanning electron microscope (FE-SEM; model JOEL JSM-6700F), and the results are shown in FIGS. 1A and 1B.
Comparing fig. 1A and 1B, it can be seen that the composition of zinc acrylate salt of example 2 has a clear shape and no large agglomeration; larger agglomerates were observed against the zinc acrylate salt composition of comparative example 1. It can be seen that the zinc acrylate salt composition of example 2 has better dispersibility than that of comparative example 1.
Test example 3: evaluation of adhesion of Metal acrylate composition to Metal surface
Before the test, the zinc acrylate salt compositions of example 2 and comparative example 1 were dried in an oven at 50 ℃ for 3 hours and then returned to room temperature, 100 g of each composition was sampled and placed in a two-axis screw feeder for carrying out the procedure of conveying powder, the powder sticking and residue on the surface of the metal member of the feeder were observed after the conveying procedure was completed, and then the powder remaining on the surface of the metal member was collected and weighed to evaluate the sticking property of the powder to the metal surface.
The weight of the powder remained on the surface of the metal component of the zinc acrylate salt composition of the embodiment 2 is 2.92 g after measurement; the zinc acrylate salt composition of comparative example 1 had a powder weight remaining on the surface of the metal member of 10.23 g. As can be seen from the measured powder residual weight, the zinc acrylate salt composition of example 2 hardly adhered to the surface of the metal member, showing a considerably small amount of powder residue; in contrast, the zinc acrylate salt composition of comparative example 1 has a higher adhesion to the surface of the metal member, which results in a large amount of powder remaining on the metal surface, that is, compared to comparative example 1, the zinc acrylate salt composition of example 2 has a lower adhesion to the metal surface, and thus a large amount of powder does not remain on the metal surface.
Test example 4: thermal conductivity of metal acrylate composition
In this test example, the heat conductivity was measured using a Hot Disk thermal conductivity meter (available from TechMark, inc., model TPS3500) according to ISO-DIS22007-2.2 standard using a multi-layer reduced graphene oxide (available from taiwan's firm and having a carbon content of 99% or more and a number of layers of 10 to 20 layers) and the zinc acrylate salt compositions of example 5 and comparative example 1 as samples. The concrete steps are that the sample is pressed into an ingot shape, and then a Hot Disk thermal conductivity meter is used for measuring the thermal conductivity, and the results are shown in table 3.
Table 3: thermal conductivity of the multi-layer reduced graphene oxide, the zinc acrylate salt compositions of example 5 and comparative example 1.
As can be seen from the results in table 3, compared to the zinc acrylate salt composition without the thermal conductive powder in comparative example 1, the thermal conductivity of the gold acrylate salt composition in example 5 is significantly improved by about 2.5 times and is close to that of the multi-layer reduced graphene oxide because the gold acrylate salt composition contains a certain proportion of thermal conductive powder (graphene).
Test example 5: evaluation of dispersibility of Heat conductive powder in Metal acrylate composition
The test examples were conducted using three groups of multilayer reduced graphene oxide (available from taiwan's inc., 99% or more carbon content and 10 to 20 layers), the zinc acrylate salt composition of example 2, and the zinc acrylate salt composition of comparative example 1, in addition to the aforementioned multilayer reduced graphene oxide, as samples. There are two methods for evaluating dispersibility in this test example: the evaluation method comprises the steps of (1) mixing 6 mg of the samples with 250 mg of silicone oil respectively, observing the samples with an optical microscope after uniformly stirring, selecting a numerical value with the first five major diameters in the observed black sheet-shaped objects (representing the aggregates of the heat-conducting powder) under the condition that the brightness of lamp light is brightest, and recording the average value; evaluation method (2) particle sizes of the sample dispersed in ethanol by ultrasonic oscillation for 1 minute were recorded as D90 and D50 by laser particle size analysis. The results of the foregoing evaluation methods (1) and (2) are shown in Table 4.
Table 4: the dispersibility evaluation results of three groups of the multilayered reduced graphene oxide, the zinc acrylate salt composition of example 2, and the zinc acrylate salt composition of comparative example 1, with the addition of the multilayered reduced graphene oxide.
As can be seen from the results in table 4, the black flakes in example 2 having the lowest average flake diameter, i.e., the aggregates containing the heat conductive powder with the smallest size, showed good dispersibility in the heat conductive powder in example 2, and further, the black flakes in example 2 having a smaller flake diameter and closer flake diameters were observed from the results of the five-step size, thereby showing good dispersibility. In addition, with respect to the results of the evaluation method (2), example 2 also had the lowest particle diameter D90 and particle diameter D50, and thus it could also be confirmed that it had good dispersibility.
Resin composition
The foregoing metal acrylate composition was further applied to a resin composition and simultaneously compared with the groups to which the metal acrylate composition was not added to evaluate the difference in properties of hardness, specific gravity, maximum tensile strength, elongation at break, tear strength, compression set, reverse elasticity, hue, and the like, for each group. The foregoing characteristics are obtained by the following methods.
1. Hardness: the samples were cut into round or square test pieces having a thickness of at least 6 mm according to ASTM Standard D2240, and the center of the test piece was spaced at least 12 mm from each side, as measured using a Shore A (shore A) durometer on samples of polyolefin elastomers (manufacturer: TECCLOCK; model: GS-709N); the hardness of the foamed elastomer was measured by a Shore C (Shore C) hardness tester (trade name: TECLOCK; model number: GS-701N TYPE C), the measurement was performed at a temperature of 23. + -. 2 ℃ and the measurement was performed by hand and the data was read within 1 second, and the average of the five times of the data was taken as the hardness obtained by the measurement.
2. Specific gravity: according to ASTM standard D792, samples are cut into test pieces with dimensions of 3 × 2.5 × 1 cm, placed in an environment with a temperature of 23 + -2 deg.C and a humidity of 50 + -10% for at least 40 hours, weighed at a temperature of 23 + -2 deg.C with an electronic balance (manufacturer: Percisa; model: 125A SCS), three sets of weight data are taken, averaged, and specific gravity (unit: g/cm) is calculated3)。
3. Maximum tensile strength: according to the D412 standard defined in ASTM, the sample was cut into test pieces with a C-type die, and the test pieces were measured at a tensile rate of 500. + -.50 mm per minute in a tensile tester (manufacturer: high-speed railway technology; model: AI-7000S) at a temperature of 23. + -. 2 ℃ in three groups, and the average of the three data was taken as the maximum tensile strength (unit: kg/cm)2)。
4. Elongation at break: the test pieces were cut with a C-type cutter of a mold according to the D412 standard specified in ASTM, and the test pieces were measured at a tensile rate of 500. + -. 50 mm per minute using a tensile tester (manufacturer: high-speed rail technology; model: AI-7000S) under a temperature environment of 23. + -. 2 ℃ in three groups, and the average of the data of the three groups was taken as the elongation at break (unit:%).
5. Tear strength: according to the D624 standard defined by ASTM, a sample was cut with a mold C type cutter into test pieces having a thickness of 1 cm, the test pieces were measured at a tensile speed of 500 + -50 mm per minute in a temperature environment of 23 + -2 ℃ using a tensile tester (manufacturer: high-speed railway technology; model: AI-7000S), the number of the measurements was three groups, and the average of the three groups of data was taken as the tear strength (unit: kg/cm).
6. Compression set: method B (C) according to ASTM Standard D395B) The samples were cut into circular test pieces having a diameter of 29.0 ± 0.5 mm, and the permanent compression distortion measuring device (manufacturer: high-speed rail technology; the model is as follows: GT-7049) and test pieces were placed in an environment of a temperature of 23 ± 2 ℃ and a humidity of 50 ± 10% for at least 3 hours, then the test pieces were placed on a pad in a permanent compression skewness measuring instrument and compressed to 50% of the original thickness of the test pieces, and compressed at a temperature of 23 ± 2 ℃ for 22 hours, the thickness of the test pieces was measured 30 minutes after releasing the pressure, at least 2 groups of test pieces were measured, and the compression set was calculated after calculating the average value thereof, and the calculation formula of the compression set was as follows (unit: %):
CB＝[(to-ti)/(to-tn)]×100％；
CBpercent compression set;
toinitial test piece thickness (original thickness of the specimen);
titest piece final thickness (final thickness of the specimen);
tnthickness of the mat (thickness of the space bars used).
7. Reverse poking elasticity: a sample was cut into test pieces having a thickness of 12.5. + -. 0.5 mm according to ASTM D2632-2001(2008), and the center of the test piece was spaced at least 14 mm from each side, and then, 28 g of an impact hammer was dropped onto the test piece from a release height of 40 cm by using a vertical elasticity tester (manufacturer: high-speed railway technology, model: GT-7042-V1) at a temperature of 23. + -. 2 ℃ and the vertical rebound height of the impact hammer was visually read with a ruler, and 3 sets of test pieces were measured in total for 6 times per test piece, and the ratio (unit:%) of the average vertical rebound height of the impact hammers from 4 th to 6 th to the release height was taken.
8. Hue: selecting HunterLab
The EZ color difference meter measures the whiteness, yellowness and brightness of the foamed elastomer without the outer skin and averages out the average value of three tests per sample to obtain the average whiteness (WI value), the average yellowness (YI value) and the average brightness (L x value).
Test example 6: assisted Cross-Linkability testing of Metal acrylate compositions
This test example was conducted to test the auxiliary crosslinking property of the zinc acrylate salt compositions of example 2 and comparative example 1. The formulation of the resin composition sample used in the measurement and the preparation thereof were as follows, based on 100 wt% of butadiene rubber (product No. BR40 and available from Taiwan Chimei Co., Ltd.), 29 wt% of the metal acrylate composition, 18 wt% of zinc oxide and 1.5 wt% of dicumyl peroxide were used, and then the above-mentioned raw materials were kneaded uniformly by a plastograph at a process control temperature of 45 ℃ to 65 ℃ until the kneaded material was uniform, 6 g of the mixture was weighed out and subjected to vulcanization curve analysis (control parameter 170 ℃/10 min/swing angle of 0.5 ℃) by a closed type sulfur analyzer (manufacturer: middle model No. EKT-2000S), and the lowest torque (M) was recordedL) Maximum torque (M)H) Scorch time (Ts2) and sulfur transition time (Tc90) are listed in Table 5 below.
Table 5: the results of the vulcanization curve analysis of the resin compositions added in example 2 and comparative example 1.
From the results in table 5, it is understood that the zinc acrylate salt composition of example 2 does not affect the progress of vulcanization even when graphene is contained as the heat conductive powder, and shows that the zinc acrylate salt composition of example 2 has good auxiliary crosslinking properties as well.
Examples 11 to 21: resin composition
The raw materials of the "resin composition" of the following examples include the copolymer (A), the unsaturated aliphatic polyolefin (B), the organic peroxide (C), the metal acrylate composition (D), the auxiliary (E) and the foaming agent (F). In addition, the resin composition may further include a filler (G).
Wherein the copolymer (A) can be selected from ethylene/vinyl acetate copolymer (A1) (available from Taiwan polymers, Inc.; trade name: EVATHENE UE-634); the unsaturated aliphatic polyolefin (B) may be selected from: ethylene propylene diene monomer (B1) (available from DOW; trade name: Nordel IP 4570), butadiene rubber (B2) (available from Taiwan Qimei, China; trade name: BR40), or mixtures thereof; the organic peroxide (C) can be dicumyl peroxide (C1) (available from Juntai chemical company; trade name: ACEOX DCP); the metal acrylate composition (D) may be selected from the metal acrylate compositions of the foregoing examples 1 to 10; the auxiliary agent (E) can be selected from: stearic acid (E1), zinc stearate (E2), zinc oxide (E3), or mixtures thereof; the foaming agent (F) can be selected from azodicarbonamide (F1) (available from Jun Tai chemical company; trade name: ACEOX AC 3000); the filler (G) may be calcium carbonate (G1).
First, the copolymer (A), the unsaturated aliphatic polyolefin (B), the metal acrylate composition (D) and the auxiliary (E) were put into a kneader (manufacturer: Linay machine; type: KD-3-20), melt-kneaded at a temperature of 60 ℃ to 100 ℃ for 5 minutes at a rotational speed of 40rpm, then the organic peroxide (C) and the foaming agent (F) were added, and melt-kneaded at a temperature of 80 ℃ to 100 ℃ for 5 minutes at a rotational speed of 40rpm to form a resin composition.
In the resin compositions of examples 11 to 21, the amounts of stearic acid (E1), zinc stearate (E2) and zinc oxide (E3) as the auxiliary (E) were fixed to 0.88 parts by weight, 1.36 parts by weight and 2.24 parts by weight, respectively, based on 100 parts by weight of the unsaturated aliphatic polyolefin (B) and the relative parts by weight of the other materials. The ingredients and amounts of the remaining components in the resin compositions of examples 11 to 21, except for the fixed amounts of the auxiliary, are listed in the following table 6. The effect of the metal acrylate composition (D) on the properties of the resin composition was examined by controlling the compounding ratio.
Comparative examples 3 to 6 and comparative example 1: resin composition
Comparative examples 3 to 6 and comparative example 1 resin compositions were prepared substantially as in examples 11 to 21 except that the metal acrylate salt composition (D) in the resin compositions of comparative examples 3 to 6 was selected from the zinc acrylate salt compositions of comparative examples 1 and 2; the resin composition of comparative example 1 was not added with the metal acrylate composition (D). The constituent components and the amounts of the respective components of the resin compositions of comparative examples 3 to 6 and comparative example 1 are also shown in Table 6 below.
Table 6: the constituent components and the amounts of the respective components of the resin compositions of examples 11 to 21, comparative examples 3 to 6 and comparative example 1.
Examples 19A to 21A and comparative examples 5A, 6A: polyolefin elastomer
The blowing agent-free resin compositions of examples 19 to 21 and comparative examples 5 and 6 were selected and calendered into a film by means of a double-roller mixer (manufacturer: Asaheng, type: HF-2 RM).
Then, 32 g of the above-mentioned foaming agent-free film was sampled and placed at the center of a metal mold having a thickness of 2 mm, a length of 120 mm and a width of 120 mm, and then heated at 165. + -. 5 ℃ and a temperature of 100. + -.5 kg/cm2Was heated under pressure for 10 minutes to give examples 19A to 21A and ratiosThe polyolefin elastomers of comparative examples 5A and 6A.
Examples 11A to 18A, comparative examples 3A, 4A, and comparative example 1A: foamed elastomer
The resin compositions containing a foaming agent of examples 11 to 18, comparative examples 3 and 4 and comparative example 1 were selected and cut into rubber pellets having a length of about 3 mm by a pelletizer (manufacturer: Linay machine, type: KD-FR-50) or calendered into a rubber sheet by a double-roll mixer (manufacturer: Asaheng, type: HF-2 RM).
Then, 42 g of the above-mentioned prepared crumb or film was sampled and placed in a metal mold having a thickness of 8 mm, a length of 120 mm and a width of 50 mm at a temperature of 165. + -. 5 ℃ and a weight of 160. + -. 10kg/cm2The foamed elastomers of examples 11A to 18A, comparative examples 3A, 4A and comparative example 1A were obtained in this order by heating under pressure for 10 to 20 minutes.
The polyolefin elastomers of examples 19A to 21A and comparative examples 5A and 6A and the foamed elastomers of examples 11A to 18A, comparative examples 3A and 4A and comparative example 1A were tested by the above-mentioned methods to obtain the results of hardness, specific gravity, maximum tensile strength, elongation at break, tear strength, compression set, reverse elasticity, hue and the like, and are shown in Table 7. In addition, in order to evaluate the influence of the content of the heat conductive powder contained in the metal acrylate composition of the present invention on the characteristics of the resin composition, the content of the heat conductive powder in the resin composition (abbreviated as heat conductive powder content [ resin ] in table 7) is also shown in table 7, which is calculated by multiplying the weight of the metal acrylate composition (D) by the content of the heat conductive powder shown in table 1, and dividing by the total weight of the resin composition, and the unit thereof is expressed in parts per million (ppm).
Table 7: the polyolefin elastomers of examples 19A to 21A and comparative examples 5A, 6A and the foamed elastomers of examples 11A to 18A, comparative examples 3A, 4A and comparative example 1A.
First, examples 11A to 17A and comparative example 3A are all groups in which ethylene-propylene-diene rubber (B1) was used as the unsaturated aliphatic polyolefin (B) and a blowing agent was added, and the composition components were controlled to be the same except for the metal acrylate composition, and therefore, the difference in the results of the groups was estimated to be due to the difference in the components and the amounts of the metal acrylate composition added. For the evaluation of the mechanical properties such as the maximum tensile strength and the tear strength of the foamed elastomers, please refer to the test results of the maximum tensile strength and the tear strength of the foamed elastomers of examples 11A to 16A and comparative example 3A in table 7, the maximum tensile strength and the tear strength are 16.6kg/cm respectively compared to comparative example 3A2And 9.58kg/cm, the maximum tensile strength and tear strength of examples 11A to 16A are clearly considerably improved. It can be seen that the foamed elastomers of examples 11A to 16A exhibit better maximum tensile strength and tear strength, i.e., have the effect of increasing mechanical strength, due to the inclusion of the metal acrylate composition containing the thermally conductive powder of the present invention. Furthermore, referring back to example 17A, which is a group with additional calcium carbonate as filler, it can also be observed from the experimental results of maximum tensile strength and tear strength in table 7 that the maximum tensile strength and tear strength of example 17A are still significantly better than those of comparative example 3A.
In example 18A and comparative example 4, which are both groups using a butadiene rubber (B2) as the unsaturated aliphatic polyolefin (B) and a foaming agent, the composition components were controlled to be the same except for the metal acrylate composition, and therefore, the difference in the results between the groups was estimated to be due to the difference in the components and the amounts of the metal acrylate composition added. As is clear from the test results in Table 7, the maximum tensile strength and the tear strength were 13.4kg/cm, respectively, as compared with comparative example 4A2And 7.5kg/cm, example 18A has a maximum tensile strength and tear strength of 13.5kg/cm2And 8.2kg/cm, also show improved mechanical properties, not only, example 18A compression setThe deformation was 13.5%, which was also superior to the compression set (15.1%) of comparative example 4A.
In addition, please refer to the hue test results of examples 11A to 13A and comparative example 3A. Generally, when graphene, flake graphite, or a combination thereof is added as a heat conductive powder to a resin composition, a decrease in Whiteness (WI) can be expected, however, it can be found from the results of WI of examples 11A to 13A and comparative example 3A that, when the heat conductive powder is present in a specific amount in the resin composition, it is unexpectedly possible to further produce the effect of whitening, and furthermore, as compared with the results of Yellowness (YI) and brightness (L) of examples 11A to 13A and comparative example 3A, it is shown that the heat conductive powder having a specific amount in the resin composition can also simultaneously have the effects of lowering yellowness and generating haze. That is, the metal acrylate composition with specific content of the heat conductive powder is applied to the resin composition, and can further provide whitening, yellow light removing and matte effects, thereby having good appearance and texture.
On the other hand, examples 19A to 21A and comparative examples 5A and 6A are also groups in which ethylene-propylene-diene rubber (B1) was used as the unsaturated aliphatic polyolefin (B) but no blowing agent was added, and the composition components were controlled to be the same except for the metal acrylate composition, and therefore, the difference in the results of the groups was estimated to be due to the difference in the components derived from the metal acrylate composition added. From the results of examples 19A to 21A and comparative examples 5A and 6A in table 7, it can be seen that the polyolefin elastomers of examples 19A to 21A have significantly improved maximum tensile strength compared to those of comparative examples 5A and 6A to which the metal acrylate composition containing no heat conductive powder is added, thereby showing that the metal acrylate composition containing heat conductive powder of the present invention has the effect of improving mechanical strength when applied to the unfoamed resin composition. In addition, the results of the maximum tensile strength tests of examples 19A and 20A and comparative example 5A at three different positions of the test piece are compared with comparative example 5A (106.8 kg/cm each)2、83.6kg/cm2、127.1kg/cm2Average 105.8kg/cm2) Example 19A (126.2 kg/cm, respectively)2、116.7kg/cm2、123.4kg/cm2Average of 122.1kg/cm2) And example 20A (137.1 kg/cm, respectively)2、137.6kg/cm2、132.4kg/cm2Average of 135.7kg/cm2) The higher consistency of the maximum tensile strength at different positions shows that the addition of the metal acrylate composition containing the heat-conducting powder also has the effect of improving the mechanical strength on average.
Test example 7: observation of cell dispersibility of foamed elastomer
The results of imaging the foamed elastomers of example 12A and comparative example 3A at a magnification of 100 times using a field emission scanning electron microscope (model No. JOEL JSM-6700F) are shown in fig. 2A to 2C and fig. 2D to 2F, in which fig. 2A to 2C correspond to the upper, middle and lower portions of the foamed elastomer of example 12A, respectively; FIGS. 2D to 2F correspond to the upper, middle and lower portions of the foamed elastomer of comparative example 3A, respectively.
It can be observed from fig. 2A to 2C that the foamed elastomer of example 12A has a relatively similar number and distribution of cells in the upper, middle and lower three parts, i.e., shows that the cells have good dispersibility in the foamed elastomer of example 12A; in contrast to fig. 2D to 2F, the foamed elastomer of comparative example 3A has a significant difference in the number and distribution of cells in the upper, middle and lower portions, and particularly, the number of cells of fig. 2D is significantly greater than that of fig. 2F, so that it can be seen that the foamed elastomer of example 12A indeed has good uniformity of cell dispersion, i.e., by adding the metal acrylate composition containing graphene or flake graphite to the resin composition and forming the foamed elastomer, the uniformity of dispersion of cells in the foamed elastomer can be improved indeed.
Claims (20)
1. A metal acrylate composition comprising:
a metal salt of monoacrylate, represented by formula I;
in formula I, M2+Is zinc ion, magnesium ion or calcium ion, R1 is hydrogen radical or saturated alkyl with 1-6 carbon atoms; and
the heat conducting powder is graphene, crystalline flake graphite or a combination thereof, and the content of the heat conducting powder is 0.3 to 25 weight percent based on the total weight of the metal acrylate composition.
2. The metal acrylate composition according to claim 1, wherein the thermally conductive powder is present in an amount of 0.3 to 8 wt%, based on the total weight of the metal acrylate composition.
3. The metal acrylate composition according to claim 2, wherein the thermally conductive powder is contained in an amount of 0.3 to 2 wt% based on the total weight of the metal acrylate composition.
4. The metal acrylate composition according to any one of claims 1 to 3, wherein the graphene comprises reduced graphene oxide having a carbon content of 40% or more and a number of layers of 3 to 30; the flake graphite comprises flake graphite with carbon content of more than 95%.
5. The metal acrylate composition according to claim 4, wherein the graphene comprises reduced graphene oxide having a carbon content of 60% or more and a number of layers of 3 to 20; the flake graphite comprises flake graphite with the carbon content of more than 98 percent.
6. A method of making the metal acrylate composition of any one of claims 1 to 5 comprising the steps of:
step a): reacting acrylic acid, divalent metal oxide and heat-conducting powder in a non-polar solvent at a temperature of 30-100 ℃ to obtain a first mixture; and
step b): removing the solvent from the first mixture to obtain the metal acrylate composition;
wherein the heat-conducting powder is graphene, crystalline flake graphite or a combination thereof, and the content of the heat-conducting powder is 0.3 to 25 weight percent based on the total weight of the metal acrylate composition.
7. The method for preparing a metal acrylate composition according to claim 6, wherein the step a) further comprises the steps of:
step a 1): mixing the acrylic acid and the heat-conducting powder to obtain a second mixture; and
step a 2): reacting the second mixture and the divalent metal oxide in the non-polar solvent at a temperature of 30 ℃ to 100 ℃ to obtain the first mixture.
8. The method of claim 6 or 7, wherein the first mixture further comprises an additive comprising an antioxidant, a polymerization inhibitor, a heat resistant agent, a lubricant, a surfactant, or a combination thereof, and the amount of the additive is 0.02 wt% to 10 wt% based on the total weight of the metal acrylate composition.
9. The method for producing a metal acrylate composition according to claim 6 or 7, wherein the molar ratio of the acrylic acid to the divalent metal oxide is 1.4:1 to 2.1: 1.
10. The method for producing a metal acrylate composition according to claim 6 or 7 wherein the non-polar solvent comprises benzene, toluene, xylene, cyclohexane, hexane, heptane or octane.
11. A resin composition comprising an unsaturated aliphatic polyolefin and a metal acrylate composition according to any one of claims 1 to 5.
12. The resin composition according to claim 11, wherein the metal acrylate composition is used in an amount of 0.1 to 30 parts by weight based on 100 parts by weight of the unsaturated aliphatic polyolefin.
13. The resin composition of claim 11, wherein the unsaturated aliphatic polyolefin is selected from the group consisting of ethylene-propylene-diene monomer, butadiene rubber, butyl rubber, natural rubber, isoprene rubber, and combinations thereof.
14. The resin composition of claim 11, further comprising a copolymer, wherein the copolymer comprises an ethylene copolymer, a polyolefin block copolymer, or a combination thereof.
15. The resin composition of claim 14, wherein the ethylene copolymer is selected from the group consisting of ethylene/vinyl acetate copolymers, ethylene/octene copolymers, polyethylene, ethylene/alpha-olefin copolymers, ethylene/alpha-olefin non-conjugated diene copolymers, ethylene/acrylic acid copolymers, ethylene/methacrylic acid copolymers, ethylene/methyl acrylate copolymers, ethylene/methyl methacrylate copolymers, ethylene/ethyl acrylate copolymers, ethylene/ethyl methacrylate copolymers, ethylene/butyl acrylate copolymers, ethylene/butyl methacrylate copolymers, and combinations thereof.
16. The resin composition of claim 11, further comprising an organic peroxide, wherein the organic peroxide comprises an alkyl hydroperoxide, a dialkyl hydroperoxide, an aromatic hydroperoxide, a peroxyester, a diperoxyketal, a diacyl peroxide, or a peroxydicarbonate.
17. Resin composition according to any one of claims 11 to 16, further comprising a blowing agent, wherein the blowing agent comprises an azo compound, a nitroso compound or a sulfonyl hydrazide compound.
18. A polyolefin elastomer prepared from the resin composition of any one of claims 11 to 16.
19. A foamed elastomer prepared from the resin composition of any one of claims 11 to 17.
20. The foamed elastomer according to claim 19, which is applied to building materials, vehicle materials, cushioning materials, shock-proof materials, packing materials, sports pad materials, or footwear materials.
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