JP2020083972A - ウレタンプレポリマー、それを用いたポリウレタン及びシーリング材 - Google Patents
ウレタンプレポリマー、それを用いたポリウレタン及びシーリング材 Download PDFInfo
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- JP2020083972A JP2020083972A JP2018217773A JP2018217773A JP2020083972A JP 2020083972 A JP2020083972 A JP 2020083972A JP 2018217773 A JP2018217773 A JP 2018217773A JP 2018217773 A JP2018217773 A JP 2018217773A JP 2020083972 A JP2020083972 A JP 2020083972A
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- JP
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- Prior art keywords
- group
- urethane prepolymer
- examples
- diisocyanate
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000004814 polyurethane Substances 0.000 title claims abstract description 34
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 34
- 239000003566 sealing material Substances 0.000 title description 26
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 150000001875 compounds Chemical group 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 6
- 229920005862 polyol Polymers 0.000 claims description 69
- 150000003077 polyols Chemical class 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 239000004014 plasticizer Substances 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 239000006260 foam Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- -1 oxypropylene group Chemical class 0.000 abstract description 84
- 229920000570 polyether Polymers 0.000 description 43
- 239000004721 Polyphenylene oxide Substances 0.000 description 42
- 229910052736 halogen Inorganic materials 0.000 description 40
- 150000002367 halogens Chemical class 0.000 description 40
- 239000012948 isocyanate Substances 0.000 description 26
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 23
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 22
- 238000001723 curing Methods 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 17
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- 230000001588 bifunctional effect Effects 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000010276 construction Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 5
- 239000011968 lewis acid catalyst Substances 0.000 description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 5
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 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 3
- 238000004807 desolvation Methods 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 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 3
- 150000002902 organometallic compounds 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
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 210000003813 thumb Anatomy 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- BQAQHFMZRLEURF-UHFFFAOYSA-N bromo(butyl)phosphane Chemical compound CCCCPBr BQAQHFMZRLEURF-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 210000003811 finger Anatomy 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 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 2
- 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 2
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 2
- PHFDTSRDEZEOHG-UHFFFAOYSA-N hydron;octan-1-amine;chloride Chemical compound Cl.CCCCCCCCN PHFDTSRDEZEOHG-UHFFFAOYSA-N 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 150000004693 imidazolium salts Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 125000001905 inorganic group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
[1]NCO末端の液状ウレタンプレポリマーであり、
該ウレタンプレポリマーは、
式(1)で示される、数平均分子量が200以上3,000以下の構造単位を含み、かつ、
不飽和度が、0.020meq/g以下であり、
末端がNCO基である液状ウレタンプレポリマー:
Qは、式[I]で示される構造単位を含む重合体成分を表し、
mは、2〜8の整数を表し、
R1は、活性水素含有化合物残基を表す;
[2]
不飽和度が、0.016meq/g以下であることを特徴とする[1に記載の液状ウレタンプレポリマー。
[3]
[1]乃至[2]のいずれかに記載のウレタンプレポリマーと、充填剤及び他のポリオール、ウレタン化触媒、整泡剤、酸化防止剤、可塑剤のうち1種又は2種以上とを含む、液状ウレタンプレポリマー組成物。
[4]
[1]乃至[2]のいずれかに記載の液状ウレタンプレポリマー又は、[3]に記載の液状ウレタンプレポリマー組成物が、空気中の水又は硬化剤(活性水素含有化合物)との反応により硬化してなる、ポリウレタン。
[5]
[1]乃至[2]のいずれかに記載のウレタンプレポリマー又は、[3]に記載のウレタンプレポリマー組成物を含む、シーリング材用組成物。
[6]
[5]に記載のシーリング材用組成物が、空気中の水又は硬化剤(活性水素含有化合物)との反応により硬化してなる、シーリング材
<ウレタンプレポリマー>
本発明の一態様にかかるウレタンプレポリマーは、
ハロゲン含有ポリエーテルポリオールとイソシアネート化合物を反応させることにより得ることができる。
<<ハロゲン含有ポリエーテルポリオール>>
該ハロゲン含有ポリエーテルポリオールは、
式(2)で示され、
平均分子量が200以上3,000以下である
:
Qは、式[I]で示される構造単位を含む重合体成分を表し、
mは、2〜8の整数を表し、
R1は、活性水素含有化合物残基を表す;
<<ハロゲン含有ポリエーテルポリオールの製造方法>>
ハロゲン含有ポリエーテルポリオールの製造方法としては、特に制限はなく、従来公知の製造方法で製造することができる。
R2及びR3は、各々独立して、
水素原子、
炭素数1〜20の炭化水素基、
R2とR3とが互いに結合した環構造、
R2同士もしくはR3同士が互いに結合した環構造を表し;
Z−は、ヒドロキシアニオン、炭素数1〜4のアルコキシアニオン、カルボキシアニオン、炭素数2〜5のアルキルカルボキシアニオン、塩素アニオン、臭素アニオン、よう素アニオン又は炭酸水素アニオンを表し;
Yは、炭素原子又はリン原子を表し;
aは、
Yが炭素原子のとき2であり、
Yがリン原子のとき3である。
Dは、窒素原子又はリン原子を表し;
R4、R5、R6及びR7は、それぞれ独立して、
炭素数1〜20の、アルキル基、アリール基、アルコキシ基、もしくは、ジアルキルアミノ基、
ハロゲン原子、又は、
水素原子を表し;
E−は、無機又は有機の基からなる対イオンを表し;
R4〜R7のうち2〜4つが結合して環状構造を形成していてもよく、またその環状構造中にヘテロ原子を含んでいてもよい。
<<イソシアネート化合物>>
イソシアネート化合物としては特に限定されず、例えば、芳香族イソシアネート化合物、脂肪族イソシアネート化合物、脂環族イソシアネート化合物(単環式脂環族イソシアネート化合物、架橋環式脂環族イソシアネート化合物)、及びこれらのポリイソシアネート誘導体等が挙げられる。
<<液状ウレタンプレポリマー組成物>>
本発明の一態様にかかるウレタンプレポリマー組成物は、充填剤及び他のポリオール、ウレタン化触媒、整泡剤、酸化防止剤、可塑剤のうち1種又は2種以上とを含む。これらを用いる際の混合順序は特に制限はなく、適宜選択することができる。
<ポリウレタン>
本発明の一態様にかかるポリウレタンは、上記の液状ウレタンプレポリマー、又はウレタンプレポリマー組成物が空気中の水又は硬化剤(活性水素含有化合物)との反応により硬化してなる。
<シーリング材用組成物>
本発明のシーリング材用組成物は、均一な組成を形成して硬化し耐発泡性に優れやすいため、1液型が好ましい。
<シーリング材>
本発明の一態様にかかるシーリング材は、上記のポリウレタンを含むものである。
<ポリオール>
実施例、比較例では、式(5)に示される構造をもつポリオールを用いた。ポリオールの性状は表1に示す。
<<ハロゲン含有ポリエーテルポリオール(A)、(C)>>
テトラノルマルブチルアンモニウムブロミド(富士フイルム和光純薬工業社製)と、トリイソプロポキシアルミニウムを併用して脱水・脱溶媒を十分に行い、分子量400のポリプロピレングリコール(三洋化成工業社製、商品名:サンニックスPP−400)に対して、17.3mol当量のエピクロロヒドリン(富士フイルム和光純薬社製)を付加することで、分子量が2,000で2官能のハロゲン含有ポリエーテルポリオール(A)を作製した。
<<ハロゲン含有ポリエーテルポリオール(B)、(D)>>
テトラノルマルブチルアンモニウムブロミド(富士フイルム和光純薬工業社製)と、トリイソプロポキシアルミニウムを併用して脱水・脱溶媒を十分に行い、1,6−ヘキサンジオール(富士フイルム和光純薬工業社製)に対して、エピクロロヒドリン(富士フイルム和光純薬工業社製)を20.3mol当量付加することで、分子量が2000で2官能のハロゲン含有ポリエーテルポリオール(B)を作製した。
<<ハロゲン含有ポリエーテルポリオール(E)>>
テトラノルマルブチルアンモニウムブロミド(富士フイルム和光純薬工業社製)と、トリイソプロポキシアルミニウムを併用して脱水・脱溶媒を十分に行い、分子量600のポリプロピレングリコール(三洋化成工業社製、商品名:サンニックスPP−600)に対して、4.3mol当量のエピクロロヒドリン(富士フイルム和光純薬工業社製)を付加することで、分子量が1,000で2官能のハロゲン含有ポリエーテルポリオール(E)を作製した。
<<ハロゲン含有ポリエーテルポリオール(F)>>
ルイス酸触媒のBF3−Et2Oを用いて、分子量400のポリプロピレングリコール(三洋化成工業社製、商品名:サンニックスPP−400)にエピクロロヒドリンを付加することで、分子量が2,000で2官能のポリエーテルポリオール(F)を作製した。
<イソシアネート化合物>
いずれの実施例、比較例においても、4,4‘−MDI(アルドリッチ社製)を、精製することなくそのまま使用した。
(ポリオール性状の分析)
<不飽和度>
JIS−K1557−6の方法に従い、測定した。
<分子量分布(Mw/Mn)>
ポリオール10mgとTHF10mlをサンプル瓶に添加し、1終夜静置することで溶解し、PTFEカートリッジフィルター(0.5μm)でろ過することでサンプルを得た。
撹拌翼を付した4つ口のセパラブルフラスコに、ハロゲン含有ポリエーテルポリオールAを100g投入し、80℃2時間で減圧脱水を行った。室温に冷却後、窒素下で4,4’−MDIを25g投入し100℃で反応を行った。反応器内容物のジブチルアミンを用いた逆滴定により、NCO基の消費が停止するまで攪拌し、プレポリマー1を合成した。
<ポリウレタンシートの作製>
NCO末端プレポリマー合成例にて得られたプレポリマーを、離型処理したPETフィルム(帝人フィルムソリューション社製、ピューレックスA31)上にアプリケーター(YOSHIMITSU SEIKI社製)を用いて150μmなるように卓上コーター(三井電気精機社製、TC−1)にて1.0m/分の速度で塗工し、23〜25℃、50%RHの恒温室で7日間静置してポリウレタンシートを作製した。
<破断強度>
JIS3号ダンベル状に打ち抜き、 引張試験機(エー・アンド・デイ社製テンシロンTG−1210)を用いて、引張速度200mm/分での引張試験を行い、破断強度を測定した。測定は、23〜25℃、50%RHの雰囲気下で行った。試験回数は5回とし、最大値と最小値を含まない平均値を算出し破断強度とした。
A:10MPa以上
B:5MPa以上10MPa未満
C:5MPa未満
<タック性>
作製したポリウレタンに親指を押し付け、引きはがしたときの抵抗感を評価した。
A:抵抗感を殆ど感じない
B:抵抗感有り
C:べたつく
<透明性>
作製したポリウレタンシートをヘーズメーター(日本電色工業社製NDH−5000)にてヘーズを測定した。
A:5%未満
B:5%以上10%未満
C:10%以上
実施例1〜5.
ポリウレタンの評価方法に従い、プレポリマー1〜5を用いてポリウレタンシートを作製し、評価を行った。いずれも破断強度は強く、低タック性、高透明なポリウレタンシートであった。
比較例1.
ポリウレタンの評価方法に従い、プレポリマー7を用いてポリウレタンシートを作製し、評価を行った。透明性は良好だったが、硬化不良で、べたつきが生じ、破断強度に劣るものであった。
比較例2.
ポリウレタンの評価方法に従い、プレポリマー8を用いてポリウレタンシートを作製し、評価を行った。ダンベル片の破断強度は強かったが、シート表面に親指を押し付けると抵抗感が感じられ、透明性が低いものだった。
比較例3.
ポリウレタンの評価方法に従い、プレポリマー8を用いてポリウレタンシートを作製し、評価を行った。ダンベル片の破断強度は劣り、シート表面に親指を押し付けると抵抗感が感じられ、透明性が低いものだった。
<シーリング材の作製>
NCO末端プレポリマー合成例にて得られたプレポリマー100重量部に、充填剤として重質炭酸カルシウム(丸尾カルシウム社製ホワイトンSB)を80重量部、酸化防止剤としてIganox1010(BASF社製)を0.1重量部、触媒としてオクチル酸ビスマス(日本化学産業社製プキャット25)を0.1重量部加え、ニーダーで混練しペースト状のシーリング材組成物を得た。
<硬化性>
上記で得られた試験片を24時間静置後、シーリング材部分を指で触ったときの感触を評価した。
A:べたつかない
B:べたつく
C:指にシーリング材が付着する(硬化していない)
<接着性>
上記で得られた試験片を手剥離試験し、破断面を目視することにより評価した。
A:凝集破壊
B:界面剥離
<せん断剥離強度>
引張試験機(エー・アンド・デイ社製テンシロンTG−1210)を用いて、引張速度50mm/分でのせん断剥離試験を行い、せん断剥離強度を測定した。
A:5MPa以上
B:2MPa以上、5MPa未満
C:2MPa未満
応用例1.
シーリング材の評価方法に従い、プレポリマー3を用いてシーリング材を作製し、評価した。容易に施工でき、良好な硬化性、接着性、せん断剥離強度を示した。
応用比較例1.
シーリング材の評価方法に従い、プレポリマー6を用いてシーリング材を作製し、評価した。塗工時に、垂れが生じて施工性が悪く、十分に硬化せず、接着性およびせん断剥離強度に劣った。
Claims (6)
- NCO末端の液状ウレタンプレポリマーであり、
該ウレタンプレポリマーは、
式(1)で示される、数平均分子量が200以上3,000以下の構造単位を含み、かつ、
不飽和度が、0.020meq/g以下であり、
末端がNCO基である液状ウレタンプレポリマー:
Qは、式[I]で示される構造単位を含む重合体成分を表し、
mは、2〜8の整数を表し、
R1は、活性水素含有化合物残基を表す;
- 不飽和度が、0.016meq/g以下であることを特徴とする請求項1に記載の液状ウレタンプレポリマー。
- 請求項1乃至2のいずれか1項に記載のウレタンプレポリマーと、充填剤及び他のポリオール、ウレタン化触媒、整泡剤、酸化防止剤、可塑剤のうち1種又は2種以上とを含む、液状ウレタンプレポリマー組成物。
- 請求項1乃至2のいずれか1項に記載の液状ウレタンプレポリマー又は、請求項3に記載の液状ウレタンプレポリマー組成物が、空気中の水又は硬化剤(活性水素含有化合物)との反応により硬化してなる、ポリウレタン。
- 請求項1乃至2のいずれか1項に記載のウレタンプレポリマー又は、請求項3に記載のウレタンプレポリマー組成物を含む、シーリング材用組成物。
- 請求項5に記載のシーリング材用組成物が、空気中の水又は硬化剤(活性水素含有化合物)との反応により硬化してなる、シーリング材。
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