CN117295776A - Isocyanate-containing composition and two-part reaction type polyurethane resin composition - Google Patents
Isocyanate-containing composition and two-part reaction type polyurethane resin composition Download PDFInfo
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- CN117295776A CN117295776A CN202280034602.1A CN202280034602A CN117295776A CN 117295776 A CN117295776 A CN 117295776A CN 202280034602 A CN202280034602 A CN 202280034602A CN 117295776 A CN117295776 A CN 117295776A
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- China
- Prior art keywords
- isocyanate
- containing composition
- polyol
- group
- general formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 105
- 239000012948 isocyanate Substances 0.000 title claims abstract description 65
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 65
- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 37
- 239000011342 resin composition Substances 0.000 title claims abstract description 28
- 238000006757 chemical reactions by type Methods 0.000 title claims description 11
- 150000003077 polyols Chemical class 0.000 claims abstract description 85
- 229920005862 polyol Polymers 0.000 claims abstract description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 39
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 39
- 239000011256 inorganic filler Substances 0.000 claims abstract description 34
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 34
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000000524 functional group Chemical group 0.000 claims abstract description 23
- 239000004014 plasticizer Substances 0.000 claims abstract description 23
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 150000005690 diesters Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000006353 oxyethylene group Chemical group 0.000 claims description 9
- 230000017525 heat dissipation Effects 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 21
- 238000003860 storage Methods 0.000 abstract description 17
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000006866 deterioration Effects 0.000 abstract 1
- -1 adipic acid diesters Chemical class 0.000 description 55
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 14
- 229910019142 PO4 Inorganic materials 0.000 description 13
- 239000005062 Polybutadiene Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000010452 phosphate Substances 0.000 description 13
- 229920002857 polybutadiene Polymers 0.000 description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- 238000007664 blowing Methods 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 229940087291 tridecyl alcohol Drugs 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002250 absorbent Substances 0.000 description 4
- 230000002745 absorbent Effects 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 125000005591 trimellitate group Chemical group 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- QQVHEQUEHCEAKS-UHFFFAOYSA-N diundecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCC QQVHEQUEHCEAKS-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 244000125380 Terminalia tomentosa Species 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical class CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 125000003901 ceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002818 heptacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- RMIBXGXWMDCYEK-UHFFFAOYSA-N oxonane-2,9-dione Chemical compound O=C1CCCCCCC(=O)O1 RMIBXGXWMDCYEK-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VXZJUYUVOQZBNU-UHFFFAOYSA-N phosphoric acid 1,2-xylene Chemical compound P(=O)(O)(O)O.CC1=C(C=CC=C1)C.CC1=C(C=CC=C1)C.CC1=C(C=CC=C1)C VXZJUYUVOQZBNU-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellityc acid Natural products OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- CTJJGIVJOBVMEO-UHFFFAOYSA-N tetraoctyl benzene-1,2,4,5-tetracarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC(C(=O)OCCCCCCCC)=C(C(=O)OCCCCCCCC)C=C1C(=O)OCCCCCCCC CTJJGIVJOBVMEO-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/10—Metal compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/20—Mountings; Secondary casings or frames; Racks, modules or packs; Suspension devices; Shock absorbers; Transport or carrying devices; Holders
- H01M50/202—Casings or frames around the primary casing of a single cell or a single battery
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Abstract
In a polyurethane resin composition containing an inorganic filler, the mixing property with a polyol-containing composition is improved while suppressing the deterioration of the storage stability of the isocyanate-containing composition. The isocyanate-containing composition of the embodiment may be used as a polyisocyanate component of a two-part reactive polyurethane resin composition, and the isocyanate-containing composition includes: isocyanate group-containing urethane prepolymer obtained by reacting a polyisocyanate with a polyol having an average functional group number of 2.5 or less and a weight average molecular weight of 700 or more, inorganic filler, plasticizer, and method for producing the sameAt least one selected from the group consisting of the compound represented by the general formula (1) and/or the compound represented by the general formula (3).
Description
Technical Field
The present invention relates to a two-part reactive polyurethane resin composition and an isocyanate-containing composition useful as a polyisocyanate component thereof.
Background
It is known that heat dissipation is imparted by blending an inorganic filler into a polyurethane resin composition. For example, patent document 1 discloses that the heat dissipation can be improved by adding an inorganic filler, a plasticizer, and a phosphate to a polyurethane resin obtained by a reaction between a polyisocyanate and a polybutadiene polyol, and by adding the inorganic filler at a high addition ratio.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2010-150473
Disclosure of Invention
Technical problem to be solved by the invention
In the case of adding an inorganic filler to a polyurethane resin composition, in general, an inorganic filler is added to a polyol component, and a polyisocyanate component containing no inorganic filler is added thereto and mixed to react the two components. However, the polyol component containing the inorganic filler has a problem that it is difficult to mix with the polyisocyanate component containing no inorganic filler. In order to improve the mixing property of the inorganic filler and the polyisocyanate component, the storage stability of the polyisocyanate component is lowered when the inorganic filler is blended into the polyisocyanate component.
In view of the above, an object of an embodiment of the present invention is to provide an isocyanate-containing composition capable of improving the miscibility with a polyol-containing composition usable as a polyol component while suppressing the decrease in the storage stability of an isocyanate-containing composition usable as a polyisocyanate component in a polyurethane resin composition containing an inorganic filler.
Means for solving the problems
The present invention includes the following embodiments.
[1]An isocyanate-containing composition which is a polyisocyanate component capable of being used as a two-part reactive polyurethane resin composition, comprising: an isocyanate group-containing urethane prepolymer obtained by reacting a polyisocyanate with a polyol having an average functional group number of 2.5 or less and a weight average molecular weight of 700 or more; an inorganic filler; a plasticizer; and at least one selected from the group consisting of a compound represented by the following general formula (1) and a compound represented by the following general formula (3), wherein R 1 Represents OH or a group represented by the following general formula (2), and the compound represented by the above general formula (1) may be R 1 Compounds represented by OH and R 1 A mixture of compounds represented by the general formula (2), wherein k represents a number of 1 or 0, and X represents a group represented by-CH 2 -、-CO(CH 2 ) p -or-coch=ch-, where p represents an integer of 2 to 6, Z represents a carboxyl group, a sulfo group or a salt thereof, in the general formulae (1), (2) and (3), R 2 R is R 3 Each independently represents a hydrocarbon group having 6 to 30 carbon atoms, A 1 O and A 3 O independently represents an oxyalkylene group having 2 to 4 carbon atoms, m and n are average addition mole numbers of alkylene oxides and independently represent numbers of 1 to 100, respectively, (A) 1 O) m (A) 3 O) n Independently of each other, and the content of the oxyethylene group is 20 mol% or more.
[ chemical 1]
[2] The isocyanate-containing composition of [1], wherein,
the polyisocyanate is aliphatic diisocyanate and/or alicyclic diisocyanate.
[3] The isocyanate-containing composition of [1] or [2], wherein,
the inorganic filler is contained in an amount of 50 to 95 mass% based on 100 mass% of the isocyanate-containing composition.
[4] The isocyanate-containing composition according to any one of [1] to [3], wherein,
the plasticizer is phthalic diester and/or adipic diester.
[5] A two-part reactive polyurethane resin composition comprising: [1] the isocyanate-containing composition according to any one of [4], which comprises a polyol and an inorganic filler.
[6] The two-part reactive polyurethane resin composition of [5], which is useful as a heat dissipating material.
Effects of the invention
According to the embodiment of the present invention, the mixing property with the polyol-containing composition can be improved while suppressing the decrease in the storage stability of the isocyanate-containing composition.
Detailed Description
The two-part reaction type polyurethane resin composition of the present embodiment includes: a polyol-containing composition as a polyol component; and an isocyanate-containing composition as a polyisocyanate component.
< isocyanate-containing composition >
[ urethane prepolymer (a) ]
The isocyanate-containing composition comprises a urethane prepolymer (a). In the present embodiment, as the urethane prepolymer (a), an isocyanate group-containing urethane prepolymer containing a polyol and a polyisocyanate having an average functional group number of 2.5 or less and a weight average molecular weight of 700 or more as constituent components can be used.
By setting the average functional group number (average hydroxyl number) of the polyol to 2.5 or less, the hardness of the cured polyurethane resin can be reduced, and for example, when the two-part reaction type polyurethane resin composition is used as a gap filler for filling a void around a battery, the reaction force caused by external force can be reduced. The average functional group number of the polyol is preferably 2.4 or less, more preferably 2.3 or less. The lower limit of the average functional group number of the polyol is not particularly limited, and for example, the average functional group number may be 1.7 or more. The polyol preferably has hydroxyl groups at both ends, and thus the average functional group number is preferably 2.0 or more.
By setting the weight average molecular weight (Mw) of the polyol to 700 or more, the storage stability of the isocyanate-containing composition can be improved. The weight average molecular weight of the polyol is preferably 800 or more. The upper limit of the weight average molecular weight of the polyol is not particularly limited, and for example, the weight average molecular weight may be 10000 or less or 5000 or less. In the present specification, the weight average molecular weight is a value measured by gel permeation chromatography (GPC (Gel Permeation Chromatography) method) and calculated using a calibration curve based on standard polystyrene.
The polyol is not particularly limited, and examples thereof include: polyether polyol, polyester polyol, polycarbonate polyol, polybutadiene polyol, polyisoprene polyol, etc., which may be used either singly or in combination. Examples of the polyether polyol include polyoxyalkylene polyols obtained by adding ethylene oxide or propylene oxide to a polyol or polyamine. Examples of the polyester polyol include those obtained by dehydrating and condensing carboxylic acids such as adipic acid and phthalic acid with polyhydric alcohols such as ethylene glycol and 1, 4-butanediol. The polybutadiene polyol is more preferably one having hydroxyl groups at both ends of the polybutadiene structure, and may be one obtained by hydrogenation. Among these, polypropylene glycol and/or polybutadiene polyol are preferably used.
The polyisocyanate is not particularly limited, and examples thereof include: aliphatic diisocyanate, alicyclic diisocyanate, aromatic diisocyanate, etc., are preferably used, and both may be used in combination.
Examples of the aliphatic diisocyanate include: tetramethylene diisocyanate, dodecamethylene diisocyanate, hexamethylene Diisocyanate (HDI), 2, 4-trimethylhexamethylene diisocyanate, 2, 4-trimethylhexamethylene diisocyanate, lysine diisocyanate, 2-methylpentane-1, 5-diisocyanate, 3-methylpentane-1, 5-diisocyanate, and the like. In addition, two or more of these may be used in combination.
Examples of the alicyclic diisocyanate include: isophorone diisocyanate, hydrogenated xylylene diisocyanate, 4' -dicyclohexylmethane diisocyanate, 1, 4-cyclohexane diisocyanate, methylcyclohexylene diisocyanate, 1, 3-bis (isocyanatomethyl) cyclohexane, and the like. In addition, two or more of these may be used in combination.
The urethane prepolymer (a) can be obtained by reacting the above polyol with a polyisocyanate under an excess of isocyanate groups. The ratio (molar ratio) of isocyanate groups to hydroxyl groups used to obtain the urethane prepolymer (a) is not particularly limited, and isocyanate groups are preferable:more preferably 1.7 to 2.3:1. the urethane prepolymer (a) is preferably a terminal isocyanate prepolymer having isocyanate groups at both terminals.
The blending amount of the urethane prepolymer (a) is not particularly limited, and is preferably 100% by mass of the isocyanate-containing compositionMore preferably +.>
[ inorganic filler (b) ]
The isocyanate-containing composition comprises an inorganic filler (b). By blending the inorganic filler (b), heat dissipation properties can be imparted to the cured polyurethane resin.
The inorganic filler (b) is not particularly limited, and examples thereof include: metal oxides such as aluminum oxide and magnesium oxide; metal hydroxides such as aluminum hydroxide and magnesium hydroxide; metal nitrides such as aluminum nitride and boron nitride. Any one or a combination of two or more of these may be used.
The amount of the inorganic filler (b) is preferably 50 to 95% by mass based on 100% by mass of the isocyanate-containing composition. By setting the amount of the polyurethane resin to 50 mass% or more, heat dissipation of the polyurethane resin can be improved. By setting the blending amount to 95 mass% or less, the storage stability of the isocyanate-containing composition can be improved. The blending amount is more preferably 60 mass% or more, still more preferably 70 mass% or more, still more preferably 80 mass% or more, and still more preferably 90 mass% or less.
Plasticizer (c)
The isocyanate-containing composition comprises a plasticizer (c). The plasticizer (c) is blended with the component (d) described later, whereby the storage stability of the isocyanate-containing composition is improved and the miscibility with the polyol-containing composition can be improved.
The plasticizer (c) is not particularly limited, and conventionally known plasticizers blended in polyurethane resins can be used, and examples thereof include: diesters of phthalic acid such as dioctyl phthalate, diisononyl phthalate and di-undecyl phthalate; adipic acid diesters such as dioctyl adipate and diisononyl adipate; trioctyl trimellitates, triisononyl trimellitates and other trimellitates; tetraoctyl pyromellitate, tetraisononyl pyromellitate and other pyromellitates; and phosphotriesters such as tricresyl phosphate, tri (xylene) phosphate and cresyl diphenyl phosphate, and any one or a combination of two or more of these may be used. Among these, as the plasticizer (c), phthalic diester and/or adipic diester are preferable.
The amount of the plasticizer (c) to be blended is not particularly limited, and may be, for example, 1 to 40% by mass, 3 to 35% by mass, 5 to 30% by mass, or 10 to 20% by mass based on 100% by mass of the isocyanate-containing composition.
[ Compound (d) ]
The isocyanate-containing composition contains at least one selected from the group consisting of the compound represented by the general formula (1) and the compound represented by the general formula (3) (hereinafter, sometimes referred to as a compound (d)). By blending the compound (d) together with the plasticizer (c), the storage stability of the isocyanate-containing composition is improved, and the miscibility with the polyol-containing composition can be improved.
Of the compounds (d), the compounds represented by the following general formula (1) are phosphoric esters.
[ chemical 2]
In the formula (1), R 1 Represents OH or a group represented by the following general formula (2). The phosphate represented by formula (1) may be R 1 Compounds (monoesters) represented by OH, also R 1 The compound (diester) represented by the general formula (2) may be a mixture of both.
[ chemical 3]
In the formula (1) and the formula (2), R 2 Represents a hydrocarbon group having 6 to 30 carbon atoms, more preferably a hydrocarbon group having 8 to 20 carbon atoms. Examples of the hydrocarbon group include a linear or branched alkyl group, an alkenyl group, an aryl group, or an aralkyl group, and these groups may have a substituent.
Specific examples of the alkyl group include: hexyl, isohexyl, heptyl, isoheptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, isoundecyl, dodecyl, isododecyl, tridecyl, isotridecyl, tetradecyl, isotetradecyl, pentadecyl, isopentdecyl, hexadecyl, isohexadecyl, 2-hexyldecyl, heptadecyl, isoheptadecyl, octadecyl, isostearyl, 2-octyldecyl, 2-hexyldodecyl, nonadecyl, isononadecyl, eicosyl, isoeicosyl, heneicosyl, isoeicosyl, docosyl, isodocosyl, tricosyl, isotricosyl, tetracosyl, pentacosyl, isopentacosyl, hexacosyl, isohexacosyl, heptacosyl, and isoheptacosyl.
Specific examples of the alkenyl group include: hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tetradecenyl, oleyl, and the like.
Specific examples of the aryl group include: phenyl, tolyl, xylyl, isopropylphenyl, mesityl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, styrenated phenyl, p-cumylphenyl, phenylphenyl, benzylphenyl, alpha-naphthyl, beta-naphthyl, and the like.
Specific examples of the aralkyl group include: benzyl, phenethyl, styryl, cinnamyl, benzhydryl, trityl (trityl), and the like.
In the formula (1) and the formula (2), A 1 O represents carbon numberIs an oxyalkylene group of (a). m represents the average molar number of addition of alkylene oxide +.>The number of (2) is preferably->More preferably +.>Is more preferably +.>Is a number of (c). (A) 1 O) m The content of oxyethylene groups in the oxyalkylene chain represented is 20 mol% or more. Namely, in the case of ethylene oxideWhen EO is used and the oxyalkylene other than the oxyethylene is used as AO, the +.> The content of the oxyethylene group is preferably 50 mol% or more, more preferably 70 mol% or more, still more preferably 80 mol% or more, and may be 100 mol% or more. In the case where the oxyalkylene chain contains a plurality of oxyalkylene groups, the oxyalkylene groups may be added randomly or may be added in blocks.
The phosphate represented by the formula (1) can be produced, for example, as follows: after alkylene oxide is added to a monohydric alcohol or phenol having 6 to 30 carbon atoms by a known method, a phosphorylating agent such as phosphoric anhydride, orthophosphoric acid, polyphosphoric acid, oxychlorinated phosphoric acid is reacted with the hydroxyl group at the alkylene oxide terminal of the obtained polyether monol. The monoester-type compound and the diester-type compound may be obtained as a mixture according to the production method, but these may be separated or may be used as a mixture as it is. In addition, the monoester compound may be used by reacting in the presence of water to increase the content of the monoester compound.
Of the compounds (d), the compounds represented by the following general formula (3) are sulfuric acid esters, sulfonic acid or carboxylic acid, and these may be any one or two or more kinds may be used in combination.
[ chemical 4]
In the formula (3), k represents a number of 1 or 0. X represents-CH 2 -、-CO(CH 2 ) p -or-coch=ch-, where p represents an integer from 2 to 6.
Z in formula (3) represents a carboxyl group (-COOH), a sulfo group (-SO) 3 H) Or salts thereof, may also exist in a mixture of an acid form and a salt form. Examples of the salt include: alkali metal salts, alkaline earth metal salts, ammonium salts, alkanolamine salts. Examples of the alkali metal salt include: sodium salt, potassium salt and lithiumSalts, and the like. Examples of the alkaline earth metal salt include calcium salts and magnesium salts. Examples of alkanolamine salts include: monoethanolamine salts, diethanolamine salts, triethanolamine salts, triisopropanolamine salts, and the like.
R in formula (3) 3 Represents a hydrocarbon group having 6 to 30 carbon atoms, more preferably a hydrocarbon group having 8 to 20 carbon atoms. Examples of the hydrocarbon group include a linear or branched alkyl group, an alkenyl group, an aryl group, or an aralkyl group, and these groups may have a substituent. Specific examples of alkyl, alkenyl, aryl, aralkyl and R 2 The same applies.
In the formula (3), A 3 O represents an oxyalkylene group having 2 to 4 carbon atoms. n represents the average addition mole number of alkylene oxide, which isThe number of (2) is preferably 3 to 50, more preferably 5 to 30, and still more preferably 7 to 20. (A) 3 O) m The content of the oxyethylene group in the oxyalkylene chain is 20 mol% or more. That is, when EO is used as the oxyethylene group and AO is used as the oxyalkylene group other than the oxyethylene group, the amount of the oxygen is +.>The content of the oxyethylene group is preferably 50 mol% or more, more preferably 70 mol% or more, still more preferably 80 mol% or more, and may be 100 mol% or more. In the case where the oxyalkylene chain contains a plurality of oxyalkylene groups, the oxyalkylene groups may be added randomly or may be added in blocks.
In the case where Z is a carboxyl group, the compound represented by the formula (3) is a carboxylic acid. In this case, the carboxylic acid of formula (3) can be produced, for example, by: after alkylene oxide is added to a monohydric alcohol or phenol having 6 to 30 carbon atoms by a known method, monohalogenated acetic acid or a salt thereof is used and reacted with a hydroxyl group at the terminal of the alkylene oxide in the presence of a base. Alternatively, the acid anhydride may be produced by a method based on a ring-opening reaction with an alkylene oxide terminal hydroxyl group. In the case of using monohalogenated acetic acid or a salt thereof, k=l, X is-CH in the formula (3) 2 -Z is COOH or a carboxylic acid salt thereof. In addition, in the case of the optical fiber,when an acid anhydride is used, k=1 and X is-CO (CH) 2 ) p -or-coch=ch-, Z is COOH.
In the case where Z is a sulfo group, the compound represented by formula (3) is a sulfate if k=0, and a sulfonic acid if k=l. For example, as for the sulfate, the following can be used: in the method of using known methodAfter addition of alkylene oxide to the mono-or phenols, sulfamic acid is reacted with the hydroxyl groups at the end of the alkylene oxide. In addition, for example, regarding sulfonic acid, it can be produced by: after the addition of the above alkylene oxide, a monohalogenated sulfonic acid or a salt thereof is used and reacted with a hydroxyl group at the terminal of the alkylene oxide.
The amount of the compound (d) to be blended is not particularly limited, and may be, for example, 100% by mass of the isocyanate-containing compositionCan also be +.> Can also be +.>
[ other Components ]
The urethane prepolymer (a) may be used alone as the polyisocyanate compound in the isocyanate-containing composition, or other polyisocyanate compounds may be used in combination with the urethane prepolymer (a).
The other polyisocyanate compounds are not particularly limited, and various polyisocyanate compounds having two or more isocyanate groups in one molecule can be used, and examples thereof include: aliphatic polyisocyanates, alicyclic polyisocyanates and aromatic polyisocyanates, and modified products and polynuclear products thereof, may be used singly or in combination. Specific examples of the aliphatic polyisocyanate and the alicyclic polyisocyanate include the aliphatic diisocyanate and the alicyclic diisocyanate. Examples of the aromatic polyisocyanate include: toluene diisocyanate (Tolylene Diisocyanate, TDI), diphenylmethane diisocyanate (Diphenylmethane Diisocyanate, MDI), 4' -dibenzyl diisocyanate, 1, 5-naphthyl diisocyanate, xylylene diisocyanate (Xylylene Diisocyanate, XDI), 1, 3-phenylene diisocyanate, 1, 4-phenylene diisocyanate, and the like. Examples of the modified polyisocyanate compounds include: isocyanurate modified bodies, allophanate modified bodies, biuret modified bodies, adduct modified bodies, carbodiimide modified bodies, and the like.
Among these, the isocyanurate modified product of the above polyisocyanate compound is preferably used as the other polyisocyanate compound, and more preferably the isocyanurate modified product of an aliphatic polyisocyanate. In this case, the amount of the isocyanurate modified compound to be blended is not particularly limited, and is preferably, for example, 100% by mass of the isocyanate-containing composition More preferably +.>The polyisocyanate compound preferably contains the urethane prepolymer (a) as a main component, and even when other polyisocyanate compounds are used in combination, it is preferable that the urethane prepolymer (a) is contained in an amount of more than 50% by mass, more preferably 60% by mass or more of the entire polyisocyanate compound.
In addition to the above components, various additives such as a moisture absorbent, an antioxidant, a foam stabilizer, a diluent, a flame retardant, an ultraviolet absorber, and a colorant may be added to the isocyanate-containing composition within a range that does not impair the object of the present embodiment.
The isocyanate value (NCOV) of the isocyanate-containing composition is not particularly limited and may beCan be +.>May also be
< polyol-containing composition >
[ polyol (e) ]
The polyol-containing composition comprises a polyol (e). The polyol (e) is not particularly limited, and examples thereof include: polyether polyol, polyester polyol, polycarbonate polyol, polybutadiene polyol, polyisoprene polyol, etc., which may be used either singly or in combination. Among these, polybutadiene polyol is preferably used. The polybutadiene polyol is more preferably one having hydroxyl groups at both ends of the polybutadiene structure, and may be one obtained by hydrogenation. The average functional group number of the polybutadiene polyol is preferablyMore preferably +.>
The blending amount of the polyol (e) is not particularly limited, but is preferably 2 to 30% by mass, more preferably 3 to 25% by mass, and still more preferably 5 to 20% by mass, based on 100% by mass of the polyol-containing composition.
[ inorganic filler (f) ]
The polyol-containing composition contains an inorganic filler (f). By blending the inorganic filler (f), heat dissipation properties can be imparted to the cured polyurethane resin. The inorganic filler (f) is not particularly limited, and examples thereof include: metal oxides such as aluminum oxide and magnesium oxide; metal hydroxides such as aluminum hydroxide and magnesium hydroxide; metal nitrides such as aluminum nitride and boron nitride. Any one or a combination of two or more of these may be used.
The blending amount of the inorganic filler (f) is preferably 50 to 95 mass%, more preferably 60 mass% or more, still more preferably 70 mass% or more, still more preferably 80 mass% or more, and still more preferably 90 mass% or less, based on 100 mass% of the polyol-containing composition.
Plasticizer (g)
The polyol-containing composition may also contain a plasticizer (g). By including the plasticizer (g), the hardness of the polyurethane resin after curing can be reduced. The plasticizer (g) is not particularly limited, and examples thereof include: the above-mentioned phthalic acid diester, adipic acid diester, trimellitic acid ester, pyromellitic acid ester, phosphoric acid triester, etc., may be used either singly or in combination. Among these, as the plasticizer (g), phthalic diester and/or adipic diester are preferable.
The amount of the plasticizer (g) to be blended is not particularly limited, and may be, for example, 1 to 30% by mass, 3 to 25% by mass, 5 to 20% by mass, or 5 to 15% by mass based on 100% by mass of the polyol-containing composition.
[ phosphate (h) ]
The polyol-containing composition may also contain a phosphate ester (h). By including the phosphate ester (h), the viscosity of the polyol-containing composition (h) can be reduced. As the phosphate (h), a compound represented by the above formula (1) is used.
The amount of the phosphoric acid ester (h) to be blended is not particularly limited, and may be, for example, 100% by mass of the polyol-containing compositionCan also be +.> Can also be +.>
[ other Components ]
In addition to the above components, various additives such as a moisture absorbent, a catalyst, an antioxidant, a foam stabilizer, a diluent, a flame retardant, an ultraviolet absorber, and a colorant may be added to the polyol-containing composition within a range that does not impair the object of the present embodiment.
As the catalyst, various urethane polymerization catalysts such as an organotin catalyst, an organolead catalyst, a metal catalyst such as an organobismuth catalyst, and an amine catalyst can be used.
The hydroxyl value (OHV) of the polyol-containing composition is not particularly limited, and may be Can also be +.>
< two-liquid reaction type polyurethane resin composition >
The two-part reactive polyurethane resin composition of the present embodiment is generally composed of a first part as a polyol-containing composition and a second part as an isocyanate-containing composition, and may include, as a third part, the above-mentioned other components as optional components, in addition to the polyol-containing composition and the isocyanate-containing composition.
The two-part reactive polyurethane resin composition may be manufactured by separately preparing the polyol-containing composition and the isocyanate-containing composition, i.e., the polyol-containing composition and the isocyanate-containing composition may be separately filled in different containers. The polyol-containing composition and the isocyanate-containing composition filled in different containers may also be formed into polyurethane resins and cured by mixing the polyol and the polyisocyanate at the time of use. At this time, it may be cured by heating. The two-part reactive polyurethane resin composition of the embodiment may be obtained by mixing a polyol-containing composition and an isocyanate-containing composition, and may be in a liquid state before curing or may be cured.
In the two-part reaction type polyurethane resin composition, the mixing ratio of the polyol-containing composition and the isocyanate-containing composition is not particularly limited, and for example, the molar ratio NCO/OH (index) of the isocyanate groups contained in the isocyanate-containing composition to the hydroxyl groups contained in the polyol-containing composition may be 0.5 to 1.2 or 0.6 to 0.9. Here, NCO/OH is calculated as NCOV/OHV based on the above-mentioned isocyanate value (NCOV) and hydroxyl value (OHV).
In the two-part reaction type polyurethane resin composition, the volume mixing ratio of the polyol-containing composition and the isocyanate-containing composition is not particularly limited, and is preferably More preferably +.>Further preferably +.>
The hardness of the two-part reaction type polyurethane resin composition after curing is not particularly limited, but preferably has a Shore C hardness of 60 or less, and may be
The thermal conductivity (JIS R2618) of the two-part reaction type polyurethane resin composition after curing is not particularly limited, and may be, for example, l.0W/mK or more, 2.0W/mK or more, or 2.0W/mK to 3.0W/mK.
Use of two-liquid reaction type polyurethane resin composition
The use of the two-part reactive polyurethane resin composition of the present embodiment is not particularly limited, and the composition can be used for various applications such as electric and electronic components and vehicle-mounted applications. The inorganic filler is preferably used as a heat dissipating material because of its heat dissipation property. As an embodiment, the heat-dissipating gap filler can be preferably used as a heat-dissipating gap filler for a heat source such as a battery.
Examples
Hereinafter, the two-part reactive polyurethane resin composition will be described in detail based on examples and comparative examples, but the present invention is not limited thereto.
The raw materials used in examples and comparative examples are shown below.
[ inorganic filler ]
Aluminum hydroxide: "CW-350" (density 2.4 g/cm) 3 )
Alumina 1: "DAW-45" (density 4.0 g/cm) 3 )
Alumina 2: "DAW-03" manufactured by DENKA Co., ltd. (density 4.0 g/cm) 3 )
[ polyol ]
Polybutadiene polyol: "POLYVEST HT", manufactured by EVONIK Co., ltd., average functional group number 2.3
Plasticizer (plasticizer)
DUP: di-undecyl phthalate
DOA: adipic acid di-2-ethylhexyl ester
[ polyisocyanate Compound ]
Isocyanurate: isocyanurate modified HDI, "HT600" manufactured by Vanhua chemistry "
[ moisture absorbent ]
Moisture absorbent: "MOLECULAR SIEVE 3AB" manufactured by Union Showa Co., ltd "
Examples of synthesis of prepolymers 1 to 7 used in examples and comparative examples are shown below, wherein prepolymers 1 to 7 are isocyanate group-containing urethane prepolymers.
Prepolymer 1
In a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a nitrogen-blowing tube, 33 parts by mass of Hexamethylene Diisocyanate (HDI) (produced by asahi chemical Co., ltd. "Duranate 50M") and 67 parts by mass of polypropylene glycol (average functional group number 2.0, weight average molecular weight 700 and hydroxyl value 160) (produced by AGC Co., ltd. "Excenol 720") were reacted at 90℃for 2 hours to obtain an isocyanate-terminated urethane prepolymer (prepolymer 1).
Prepolymer 2
In a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a nitrogen-blowing tube, 26 parts by mass of Hexamethylene Diisocyanate (HDI) (produced by asahi chemical Co., ltd. "Duranate 50M") and 74 parts by mass of polypropylene glycol (average functional group number 2.0, weight average molecular weight 1000, hydroxyl value 112) (produced by AGC Co., ltd. "admission 1020") were reacted at 90℃for 2 hours to obtain an isocyanate-terminated urethane prepolymer (prepolymer 2).
[ prepolymer 3]
In a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a nitrogen-blowing tube, 10 parts by mass of Hexamethylene Diisocyanate (HDI) (produced by asahi chemical Co., ltd. "Duranate 50M") and 90 parts by mass of polypropylene glycol (average functional group number 2.0, weight average molecular weight 3000, hydroxyl value 35) (produced by AGC Co., ltd. "Excenol 3020") were reacted at 120℃for 6 hours to obtain an isocyanate-terminated urethane prepolymer (prepolymer 3).
[ prepolymer 4]
In a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a nitrogen-blowing tube, 31 parts by mass of isophorone diisocyanate (IPDI) (manufactured by EVONIK corporation, "IPDI") and 69 parts by mass of polypropylene glycol (average functional group number 2.0, weight average molecular weight 1000, hydroxyl value 112) (manufactured by AGC corporation, "Excenol 1020") were reacted at 90 ℃ for 2 hours to obtain an isocyanate-terminated urethane prepolymer (prepolymer 4).
[ prepolymer 5]
In a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a nitrogen-blowing tube, 46 parts by mass of Hexamethylene Diisocyanate (HDI) (produced by asahi chemical Co., ltd. "Duranate 50M") and 54 parts by mass of polypropylene glycol (average functional group number 2.0, weight average molecular weight 400, hydroxyl value 281) (produced by AGC Co., ltd. "admission 420") were reacted at 90℃for 2 hours to obtain an isocyanate-terminated urethane prepolymer (prepolymer 5).
[ prepolymer 6]
12 parts by mass of Hexamethylene Diisocyanate (HDI) (Duranate 50M manufactured by Asahi chemical Co., ltd.) and 88 parts by mass of polybutadiene polyol (average functional group number 2.3, weight average molecular weight 3000, hydroxyl value 46) (POLYVEST HT manufactured by EVONIK Co., ltd.) were reacted at 90℃for 2 hours in a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a nitrogen-blowing tube, to obtain an isocyanate-terminated urethane prepolymer (prepolymer 6).
[ prepolymer 7]
In a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a nitrogen-blowing tube, 33 parts by mass of Hexamethylene Diisocyanate (HDI) (manufactured by asahi chemical Co., ltd. "Duranate 50M") and 68 parts by mass of castor oil (average functional group number 2.7, weight average molecular weight 941, hydroxyl value 161) (manufactured by ira oil Co., ltd. "URIC H30") were reacted at 90℃for 2 hours to obtain an isocyanate-terminated urethane prepolymer (prepolymer 7).
Examples of synthesis of phosphate 1 to phosphate 3, ammonium sulfate salt, and carboxylic acid 1 to carboxylic acid 3, which are compounds (d) used in examples and comparative examples, are shown below.
[ phosphate 1]
Into an autoclave equipped with a temperature regulator and having a stirrer, a thermometer, a nitrogen introducing pipe, a raw material charging introducing pipe and a pressure reducing exhaust pipe, 200g (1.0 mol) of tridecyl alcohol and 5g of potassium hydroxide as a catalyst were charged, the atmosphere in the autoclave was replaced with nitrogen, 440g (10 mol) of ethylene oxide was successively introduced under a pressure of 0.15MPa and a temperature of 130℃and reacted, and then neutralization was performed with acetic acid. Then, 47g (0.33 mol) of phosphoric anhydride was added to the mixture at 8Reacted with the resulting ethylene oxide 10 mol adduct at 0℃for 5 hours to give a phosphoric acid ester 1 of the general formula (1) (wherein R 2 : tridecyl, A 1 O: EO, m: 10. molar ratio of monoester to diester 1: 1) of a mixture of two or more of the following.
[ phosphate 2]
An autoclave equipped with a temperature regulator and having a stirrer, a thermometer, a nitrogen inlet, a raw material charging inlet and a pressure reducing exhaust pipe was charged with 186g (1.0 mol) of laurel alcohol and 5g of potassium hydroxide as a catalyst, the atmosphere in the autoclave was replaced with nitrogen, 815g (18.5 mol) of ethylene oxide was successively introduced under a pressure of 0.15MPa and a temperature of 130 ℃ and reacted, and then neutralization was performed with acetic acid. Then, 47g (0.33 mol) of phosphoric anhydride was reacted with 18.5 mol of the resulting adduct of ethylene oxide at 80℃for 5 hours to obtain phosphoric ester 2 of the general formula (1) (wherein R 2 : lauryl, A 1 O: EO, m:18.5, molar ratio of monoester to diester 1: 1) of a mixture of two or more of the following.
[ phosphate 3]
An autoclave equipped with a temperature regulator and having a stirrer, a thermometer, a nitrogen inlet, a raw material charging inlet, and a pressure reducing exhaust pipe was charged with 200g (1.0 mol) of tridecyl alcohol and 5g of potassium hydroxide as a catalyst, the atmosphere in the autoclave was replaced with nitrogen, 264g (6 mol) of ethylene oxide and 290g (5 mol) of propylene oxide were simultaneously reacted under a pressure of 0.15MPa and a temperature of 130℃and then neutralized with acetic acid. Then, 47g (0.33 mol) of phosphoric anhydride was reacted with the obtained ethylene oxide and propylene oxide adduct at 80℃for 5 hours to obtain a phosphoric ester 3 of the general formula (1) (wherein R 2 : tridecyl (A) 1 O) m: random adduct EO/PO (oxypropylene) =6/5 (molar ratio), m: 11. molar ratio of monoester to diester 1: 1) of a mixture of two or more of the following.
[ ammonium sulfate salt ]
220g (1.0 mol) of styrenated phenol (monostyrenated phenol: distyrenated phenol: tristyrenated phenol=80:19:1 (mass ratio) mixture) was transferred in a reaction vessel with stirrer, thermometer, return tube792g (18 mol) of ethylene oxide was subjected to an addition reaction in an autoclave at a pressure of 0.15MPa and a temperature of 130℃using potassium hydroxide as a catalyst, to thereby obtain a polyoxyethylene styrenated phenyl ether. Then, the obtained polyoxyethylene styrenated phenyl ether was transferred to a reaction vessel having a stirrer, a thermometer and a nitrogen inlet tube, and 97g (l moles) of sulfamic acid was reacted under a nitrogen atmosphere at a temperature of 120 ℃. Then, monoethanolamine was added to adjust the pH of the 1 mass% aqueous solution to 7.5 to obtain an ammonium sulfate salt of the general formula (3) (wherein R 3 : styrenated phenyl group, A 3 O：EO、n：18、k：0、Z：-SO 3 NH 4 )。
[ Carboxylic acid 1]
Into an autoclave equipped with a temperature regulator and having a stirrer, a thermometer, a nitrogen introducing pipe, a raw material charging introducing pipe and a pressure reducing exhaust pipe, 200g (1.0 mol) of tridecyl alcohol and 5g of potassium hydroxide as a catalyst were charged, the atmosphere in the autoclave was replaced with nitrogen, 440g (10 mol) of ethylene oxide was successively introduced under a pressure of 0.15MPa and a temperature of 130℃and reacted, and then neutralization was performed with acetic acid. Then, 151g (1.3 mol) of the ethylene oxide adduct and sodium monochloroacetate were taken into a reactor in a toluene solvent, and stirred until uniform. Then, 52g (l.3 mol) of sodium hydroxide was added thereto at a temperature of 60℃to raise the temperature of the reaction system to 80℃to react for 3 hours. After the reaction, 120g (1.2 mol) of 98 mass% sulfuric acid was added dropwise to obtain a white suspension. Then, the white suspension was washed with distilled water, and the solvent was distilled off under reduced pressure to obtain carboxylic acid 1 of the general formula (3) (wherein R 3 : tridecyl, A 3 O：EO、n：10、k：l、X：-CH 2 -、Z：-COOH)。
[ Carboxylic acid 2]
Into an autoclave equipped with a temperature regulator and having a stirrer, a thermometer, a nitrogen introducing pipe, a raw material charging introducing pipe and a pressure reducing exhaust pipe, 200g (1.0 mol) of tridecyl alcohol and 5g of potassium hydroxide as a catalyst were charged, and the atmosphere in the autoclave was replaced with nitrogen,440g (10 moles) of ethylene oxide was introduced successively under a pressure of 0.15MPa and a temperature of 130℃and reacted, followed by neutralization with acetic acid. Then, 156g (1 mol) of suberic anhydride was reacted at 120℃for 2 hours to obtain carboxylic acid 2 of the general formula (3) (wherein R 3 : tridecyl, A 3 O：EO、n：10、k：l、X：-CO-(CH 2 ) 6 -、Z：-COOH)。
[ Carboxylic acid 3]
Into an autoclave equipped with a temperature regulator and having a stirrer, a thermometer, a nitrogen introducing pipe, a raw material charging introducing pipe and a pressure reducing exhaust pipe, 200g (1.0 mol) of tridecyl alcohol and 5g of potassium hydroxide as a catalyst were charged, the atmosphere in the autoclave was replaced with nitrogen, 440g (10 mol) of ethylene oxide was successively introduced under a pressure of 0.15MPa and a temperature of 130℃and reacted, and then neutralization was performed with acetic acid. Then, 198g (1 mol) of maleic anhydride was reacted at 120℃for 2 hours to obtain carboxylic acid 3 of the formula (3) (wherein R 3 : tridecyl, A 3 O：EO、n：10、k：l、X：-CO-CH 2 ＝CH 2 -、Z：-COOH)。
The average functional group number, weight average molecular weight, hydroxyl number and isocyanate number were measured as follows.
[ average number of functional groups ]
The average functional group number is a number average molecular weight (Mn) measured by GPC (gel permeation chromatography) and is measured in accordance with JIS K1557-l: 2007A method measures a hydroxyl value (mgKOH/g) and uses a value calculated by the following formula.
Average functional group number = { (hydroxyl value) × (Mn) }/(56.11×1000)
[ weight average molecular weight and number average molecular weight ]
The measurement was performed by GPC (gel permeation chromatography), and a calibration curve prepared from the molecular weight and elution time of standard polystyrene was used, and the value was calculated from the elution time of the measurement sample. The measurement conditions were measured using TSKge1 Hxl (Tosoh Co., ltd.) under conditions that the mobile phase was Tetrahydrofuran (THF), the mobile phase flow rate was 1.0mL/min, the column temperature was 40 ℃, the sample injection amount was 50. Mu.L, and the sample concentration was 0.2 mass%.
[ hydroxyl value ]
According to JIS K1557-l:2007 method A.
[ isocyanate value ]
Is in accordance with JIS K1603-l: 2007A method comprises measuring the isocyanate content and calculating the isocyanate value from the obtained isocyanate content by using the following formula.
[ number 1]
56.11: molecular weight of potassium hydroxide
1000: conversion coefficient from g to mg
42.02: molecular weight of NCO
100: conversion coefficient from percent to/g
[Is->]
Polyol-containing compositions were prepared in accordance with the compounding (mass%) shown in Table 1 below/>And was prepared according to the compounding (mass%) shown in the following Table 2For-> Storage stability was evaluated. In addition, anotherIn addition, the ++were mixed in the combinations and the volume ratios shown in Table 3 below> And (3) with And the miscibility of the two was evaluated. Further, the hardness of the cured product was measured after mixing and curing. The method for measuring/evaluating the storage stability, the miscibility and the hardness is as follows.
[ storage stability ]
The properties of the isocyanate-containing composition thus prepared after storage at 60℃for 1 month were evaluated, and the case of maintaining the liquid state was shown as "liquid" in Table 3, and the case of curing from the liquid was shown as "cured" in Table 3.
[ mixing Property ]
The polyol-containing composition and the isocyanate-containing composition were stirred at 2000 rpm for 30 minutes at normal temperature using a rotation/revolution mixer, and the cases where mixing was possible were indicated by "o" in table 3, and the cases where mixing was impossible were indicated by "x" in table 3.
[ hardness ]
The polyol-containing composition and the isocyanate-containing composition were mixed at normal temperature and cured, and passed through JIS K7312:1996 (spring hardness test type C) hardness (Shore C) after 7 days at normal temperature was measured.
TABLE 1
| Polyol-containing compositions | A1 | A2 | A3 | A4 | A5 | A6 | A7 |
| Compounding (mass%) | |||||||
| Aluminum hydroxide | 82.1 | 60.1 | 40.8 | 82.1 | 87.3 | 81.9 | |
| Alumina 1 | 52.9 | ||||||
| Alumina 2 | 35.3 | 44.4 | |||||
| Polybutadiene polyol | 10.0 | 22.0 | 5.6 | 7.1 | 10.0 | 3.5 | 5.0 |
| DUP | 7.8 | 17.8 | 6.1 | 7.6 | 9.1 | 13.0 | |
| DOA | 7.8 | ||||||
| Phosphoric acid ester 1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Totalizing | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| OHV(mgKOH/g) | 4.7 | 10.3 | 2.6 | 3.3 | 4.7 | 2.3 | 2.3 |
| Inorganic filler amount (vol%) | 64 | 37 | 64 | 64 | 64 | 73 | 64 |
| Inorganic filler amount (mass%) | 82 | 60 | 88 | 85 | 82 | 87 | 82 |
TABLE 2
TABLE 3
The results are shown in Table 3. In comparative example 1, the average functional group number of the polyol constituting the isocyanate group-containing urethane prepolymer is large, and therefore the hardness of the cured product is high. In comparative example 2, the weight average molecular weight of the polyol constituting the isocyanate group-containing urethane prepolymer is small, and therefore the isocyanate group-containing composition solidifies in storage at 60 ℃ for 1 month, and the storage stability is low. In comparative example 3, the compound (d) such as phosphate or ammonium sulfate was not blended in the isocyanate-containing composition, and thus the storage stability was lowered. In comparative example 4, since the inorganic filler was not blended in the isocyanate-containing composition, the mixing property of the isocyanate-containing composition and the polyol-containing composition was poor. In comparative example 5, since a plasticizer was not blended in the isocyanate-containing composition, the storage stability was poor and the miscibility with the polyol-containing composition was also poor.
In contrast, the isocyanate-containing compositions of examples 1 to 16 were excellent in storage stability, good in miscibility with the polyol-containing composition, and 60 or less in hardness after curing, and good results were obtained.
While the present invention has been described with reference to several embodiments, these embodiments are presented as examples and are not intended to limit the scope of the invention. These embodiments can be implemented in various other modes, and various omissions, substitutions, and changes can be made without departing from the spirit of the invention. These embodiments and their omissions, substitutions, modifications and the like are included in the scope and gist of the invention, and are similarly included in the invention described in the claims and their equivalents.
Claims (6)
1. An isocyanate-containing composition characterized in that,
is useful as a polyisocyanate component in a two-part reactive polyurethane resin composition,
the isocyanate-containing composition comprises:
an isocyanate group-containing urethane prepolymer obtained by reacting a polyol having an average functional group number of 2.5 or less and a weight average molecular weight of 700 or more with a polyisocyanate;
an inorganic filler;
a plasticizer; and
at least one selected from the group consisting of a compound represented by the following general formula (1) and a compound represented by the following general formula (3),
in the general formula (1), R 1 Represents OH or a group represented by the following formula (2), or R 1 Compounds represented by OH and R 1 A mixture of compounds represented by the general formula (2),
in the general formula (3), k represents a number of 1 or 0, and X represents a group represented by-CH 2 -、-CO(CH 2 ) p -or-coch=ch-, where p represents an integer from 2 to 6, Z represents a carboxyl group, a sulfo group or a salt thereof,
in the general formula (1), the general formula (2) and the general formula (3), R 2 R is R 3 Each independently represents a hydrocarbon group having 6 to 30 carbon atoms, A 1 O and A 3 O independently represents an oxyalkylene group having 2 to 4 carbon atoms, m and n are average addition mole numbers of alkylene oxides and independently represent numbers of 1 to 100, respectively, (A) 1 O) m (A) 3 O) n Independently of each other and having an oxyethylene group content of 20 mol% or more,
2. the isocyanate-containing composition of claim 1, wherein,
the polyisocyanate is aliphatic diisocyanate and/or alicyclic diisocyanate.
3. The isocyanate-containing composition of claim 1 or 2, wherein,
the inorganic filler is contained in an amount of 50 to 95 mass% based on 100 mass% of the isocyanate-containing composition.
4. The isocyanate-containing composition according to any one of claim 1 to 3, wherein,
the plasticizer is phthalic diester and/or adipic diester.
5. A two-part reactive polyurethane resin composition comprising:
the isocyanate-containing composition of any one of claims 1 to 4; and
a polyol-containing composition comprising a polyol and an inorganic filler.
6. The two-part reactive polyurethane resin composition according to claim 5, wherein,
the two-part reaction type polyurethane resin composition can be used as a heat dissipation material.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2021083460 | 2021-05-17 | ||
| JP2021-083460 | 2021-05-17 | ||
| JP2021-159946 | 2021-09-29 | ||
| JP2021159946A JP7053936B1 (en) | 2021-05-17 | 2021-09-29 | Isocyanate-containing composition and two-component reaction type polyurethane resin composition |
| PCT/JP2022/019775 WO2022244650A1 (en) | 2021-05-17 | 2022-05-10 | Isocyanate-containing composition and two-part reaction type polyurethane resin composition |
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| JP (1) | JP7053936B1 (en) |
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| JP5001033B2 (en) * | 2007-03-09 | 2012-08-15 | オート化学工業株式会社 | Polyurethane curable resin composition and coating material comprising the same |
| JP6427990B2 (en) * | 2014-06-26 | 2018-11-28 | 東ソー株式会社 | Polyurethane elastomer-forming composition used for industrial machine parts and industrial machine parts using the same |
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| JP7053936B1 (en) | 2022-04-12 |
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