JPWO2020130143A1 - 歯科用接着性組成物 - Google Patents
歯科用接着性組成物 Download PDFInfo
- Publication number
- JPWO2020130143A1 JPWO2020130143A1 JP2020561549A JP2020561549A JPWO2020130143A1 JP WO2020130143 A1 JPWO2020130143 A1 JP WO2020130143A1 JP 2020561549 A JP2020561549 A JP 2020561549A JP 2020561549 A JP2020561549 A JP 2020561549A JP WO2020130143 A1 JPWO2020130143 A1 JP WO2020130143A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- polymerizable monomer
- meth
- dental
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 113
- 239000003479 dental cement Substances 0.000 title claims abstract description 109
- 239000000178 monomer Substances 0.000 claims abstract description 163
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 145
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 77
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 230000002378 acidificating effect Effects 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000003505 polymerization initiator Substances 0.000 claims description 29
- 230000002209 hydrophobic effect Effects 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000000101 thioether group Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract description 101
- 239000000853 adhesive Substances 0.000 abstract description 80
- 230000001070 adhesive effect Effects 0.000 abstract description 76
- -1 acryloyloxy group Chemical group 0.000 description 119
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 44
- 239000000945 filler Substances 0.000 description 37
- 239000002245 particle Substances 0.000 description 33
- 238000006116 polymerization reaction Methods 0.000 description 25
- 239000000463 material Substances 0.000 description 24
- 239000001294 propane Substances 0.000 description 24
- 150000002430 hydrocarbons Chemical group 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000011521 glass Substances 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 159000000000 sodium salts Chemical class 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000011256 inorganic filler Substances 0.000 description 12
- 229910003475 inorganic filler Inorganic materials 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 229910052796 boron Inorganic materials 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 210000004268 dentin Anatomy 0.000 description 9
- UCGPLXCYJOIXCO-UHFFFAOYSA-N 10-hydroxydecyl dihydrogen phosphate Chemical compound OCCCCCCCCCCOP(O)(O)=O UCGPLXCYJOIXCO-UHFFFAOYSA-N 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 229910052788 barium Inorganic materials 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 150000003863 ammonium salts Chemical class 0.000 description 7
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 7
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 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 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000005488 sandblasting Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- VNYQODQNITTWTO-UHFFFAOYSA-N 8-hydroxyoctyl dihydrogen phosphate Chemical compound OCCCCCCCCOP(O)(O)=O VNYQODQNITTWTO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 6
- 230000001588 bifunctional effect Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004575 stone Substances 0.000 description 6
- CJSXYPVHJPHCCG-UHFFFAOYSA-N 2-(prop-2-enoylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(=O)C=C CJSXYPVHJPHCCG-UHFFFAOYSA-N 0.000 description 5
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical class [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 5
- 241000705989 Tetrax Species 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 125000004450 alkenylene group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 235000011180 diphosphates Nutrition 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 159000000003 magnesium salts Chemical class 0.000 description 5
- ATTSZAWLFKAZTF-UHFFFAOYSA-N (3-nitrophenyl)boron Chemical compound [B]C1=CC=CC([N+]([O-])=O)=C1 ATTSZAWLFKAZTF-UHFFFAOYSA-N 0.000 description 4
- PVLNHYPAZWPHDM-UHFFFAOYSA-N (4-chlorophenyl)boron Chemical compound [B]C1=CC=C(Cl)C=C1 PVLNHYPAZWPHDM-UHFFFAOYSA-N 0.000 description 4
- YGGMQWSJXSNGDT-UHFFFAOYSA-N (4-fluorophenyl)boron Chemical compound [B]C1=CC=C(F)C=C1 YGGMQWSJXSNGDT-UHFFFAOYSA-N 0.000 description 4
- RVSLSGJUKZJRIW-UHFFFAOYSA-N (4-nitrophenyl)boron Chemical compound [B]C1=CC=C([N+]([O-])=O)C=C1 RVSLSGJUKZJRIW-UHFFFAOYSA-N 0.000 description 4
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical class CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 4
- AZWDISHHPONIAX-UHFFFAOYSA-N 1-butylquinolin-1-ium Chemical class C1=CC=C2[N+](CCCC)=CC=CC2=C1 AZWDISHHPONIAX-UHFFFAOYSA-N 0.000 description 4
- OIDIRWZVUWCCCO-UHFFFAOYSA-N 1-ethylpyridin-1-ium Chemical class CC[N+]1=CC=CC=C1 OIDIRWZVUWCCCO-UHFFFAOYSA-N 0.000 description 4
- CBMDQVNFHVUOIB-UHFFFAOYSA-N 1-ethylquinolin-1-ium Chemical class C1=CC=C2[N+](CC)=CC=CC2=C1 CBMDQVNFHVUOIB-UHFFFAOYSA-N 0.000 description 4
- ZWBGKXMWYNNSRH-UHFFFAOYSA-N C(CCC)C1=CC=C(C=C1)[B] Chemical compound C(CCC)C1=CC=C(C=C1)[B] ZWBGKXMWYNNSRH-UHFFFAOYSA-N 0.000 description 4
- VEQIGVGWYNVQHM-UHFFFAOYSA-N C(CCC)C=1C=C(C=CC=1)[B] Chemical compound C(CCC)C=1C=C(C=CC=1)[B] VEQIGVGWYNVQHM-UHFFFAOYSA-N 0.000 description 4
- UFUGBQFBWUBVSP-UHFFFAOYSA-N C(CCCCCCC)OC=1C=C(C=CC1)[B] Chemical compound C(CCCCCCC)OC=1C=C(C=CC1)[B] UFUGBQFBWUBVSP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical class C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 4
- LCKNZCHKSVSFHH-UHFFFAOYSA-N [3,5-bis(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)phenyl]boron Chemical compound [B]C1=CC(C(OC)(C(F)(F)F)C(F)(F)F)=CC(C(OC)(C(F)(F)F)C(F)(F)F)=C1 LCKNZCHKSVSFHH-UHFFFAOYSA-N 0.000 description 4
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical class CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 239000011350 dental composite resin Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000007561 laser diffraction method Methods 0.000 description 4
- 229910003002 lithium salt Inorganic materials 0.000 description 4
- 159000000002 lithium salts Chemical class 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 4
- 239000012766 organic filler Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 125000005385 peroxodisulfate group Chemical group 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 238000000790 scattering method Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 4
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- 150000003682 vanadium compounds Chemical class 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 3
- KCWWCWMGJOWTMY-UHFFFAOYSA-N 1-benzyl-5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1C(C=2C=CC=CC=2)C(=O)NC(=O)N1CC1=CC=CC=C1 KCWWCWMGJOWTMY-UHFFFAOYSA-N 0.000 description 3
- RTQPKEOYPPMVGQ-UHFFFAOYSA-N 1-methylquinolin-1-ium Chemical class C1=CC=C2[N+](C)=CC=CC2=C1 RTQPKEOYPPMVGQ-UHFFFAOYSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 3
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 description 3
- ZKFOEDSYSPDTEB-UHFFFAOYSA-N 2-prop-2-enoyloxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C=C ZKFOEDSYSPDTEB-UHFFFAOYSA-N 0.000 description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- HWPDIBGCECPDNL-UHFFFAOYSA-N C(CCC)OC1=CC=C(C=C1)[B] Chemical compound C(CCC)OC1=CC=C(C=C1)[B] HWPDIBGCECPDNL-UHFFFAOYSA-N 0.000 description 3
- JTPHDBMUAITJHP-UHFFFAOYSA-N C(CCC)OC=1C=C(C=CC1)[B] Chemical compound C(CCC)OC=1C=C(C=CC1)[B] JTPHDBMUAITJHP-UHFFFAOYSA-N 0.000 description 3
- SXNICUVVDOTUPD-UHFFFAOYSA-N CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 SXNICUVVDOTUPD-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 150000007656 barbituric acids Chemical class 0.000 description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 3
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- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- YGHIIBLLAKLTBT-UHFFFAOYSA-N ethyl 6-methoxy-2-oxochromene-3-carboxylate Chemical compound COC1=CC=C2OC(=O)C(C(=O)OCC)=CC2=C1 YGHIIBLLAKLTBT-UHFFFAOYSA-N 0.000 description 1
- ATXWFSDEXYKQST-UHFFFAOYSA-N ethyl 8-methoxy-2-oxochromene-3-carboxylate Chemical compound C1=CC(OC)=C2OC(=O)C(C(=O)OCC)=CC2=C1 ATXWFSDEXYKQST-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229940091249 fluoride supplement Drugs 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000003178 glass ionomer cement Substances 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LIIALPBMIOVAHH-UHFFFAOYSA-N herniarin Chemical compound C1=CC(=O)OC2=CC(OC)=CC=C21 LIIALPBMIOVAHH-UHFFFAOYSA-N 0.000 description 1
- JHGVLAHJJNKSAW-UHFFFAOYSA-N herniarin Natural products C1CC(=O)OC2=CC(OC)=CC=C21 JHGVLAHJJNKSAW-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229940079826 hydrogen sulfite Drugs 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- NZPIUJUFIFZSPW-UHFFFAOYSA-H lanthanum carbonate Chemical compound [La+3].[La+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O NZPIUJUFIFZSPW-UHFFFAOYSA-H 0.000 description 1
- 229960001633 lanthanum carbonate Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- NVBMGOHJUIFNAH-UHFFFAOYSA-M lithium;2,4,6-tri(propan-2-yl)benzenesulfinate Chemical compound [Li+].CC(C)C1=CC(C(C)C)=C(S([O-])=O)C(C(C)C)=C1 NVBMGOHJUIFNAH-UHFFFAOYSA-M 0.000 description 1
- XFBCAFRNNFDRNG-UHFFFAOYSA-M lithium;2,4,6-triethylbenzenesulfinate Chemical compound [Li+].CCC1=CC(CC)=C(S([O-])=O)C(CC)=C1 XFBCAFRNNFDRNG-UHFFFAOYSA-M 0.000 description 1
- MIVOPSLBXCQIBW-UHFFFAOYSA-M lithium;2,4,6-trimethylbenzenesulfinate Chemical compound [Li+].CC1=CC(C)=C(S([O-])=O)C(C)=C1 MIVOPSLBXCQIBW-UHFFFAOYSA-M 0.000 description 1
- MSUZXYWQEDRGFN-UHFFFAOYSA-M lithium;4-methylbenzenesulfinate Chemical compound [Li+].CC1=CC=C(S([O-])=O)C=C1 MSUZXYWQEDRGFN-UHFFFAOYSA-M 0.000 description 1
- NVSKMOMNGUJKCL-UHFFFAOYSA-M lithium;benzenesulfinate Chemical compound [Li+].[O-]S(=O)C1=CC=CC=C1 NVSKMOMNGUJKCL-UHFFFAOYSA-M 0.000 description 1
- DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- LKNDYQNNDRTHFP-UHFFFAOYSA-N n,n,3,4-tetramethylaniline Chemical compound CN(C)C1=CC=C(C)C(C)=C1 LKNDYQNNDRTHFP-UHFFFAOYSA-N 0.000 description 1
- NBFRQCOZERNGEX-UHFFFAOYSA-N n,n,3,5-tetramethylaniline Chemical compound CN(C)C1=CC(C)=CC(C)=C1 NBFRQCOZERNGEX-UHFFFAOYSA-N 0.000 description 1
- CWOMTHDOJCARBY-UHFFFAOYSA-N n,n,3-trimethylaniline Chemical compound CN(C)C1=CC=CC(C)=C1 CWOMTHDOJCARBY-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- MJRUTYCVCLZWSR-UHFFFAOYSA-N n,n-dimethyl-4-propan-2-ylaniline Chemical compound CC(C)C1=CC=C(N(C)C)C=C1 MJRUTYCVCLZWSR-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- OGUCKKLSDGRKSH-UHFFFAOYSA-N oxalic acid oxovanadium Chemical compound [V].[O].C(C(=O)O)(=O)O OGUCKKLSDGRKSH-UHFFFAOYSA-N 0.000 description 1
- MHHDXUNFNAZUGB-UHFFFAOYSA-N oxidovanadium(2+) Chemical compound [V+2]=O MHHDXUNFNAZUGB-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BFYJDHRWCNNYJQ-UHFFFAOYSA-N oxo-(3-oxo-3-phenylpropoxy)-(2,4,6-trimethylphenyl)phosphanium Chemical compound CC1=CC(C)=CC(C)=C1[P+](=O)OCCC(=O)C1=CC=CC=C1 BFYJDHRWCNNYJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- NPUSTSBKXOLJIC-UHFFFAOYSA-N phenyl(2-prop-2-enoyloxyethoxy)phosphinic acid Chemical compound C=CC(=O)OCCOP(=O)(C1=CC=CC=C1)O NPUSTSBKXOLJIC-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- HPWMVNFJSFHJIW-UHFFFAOYSA-M potassium;2,4,6-tri(propan-2-yl)benzenesulfinate Chemical compound [K+].CC(C)C1=CC(C(C)C)=C(S([O-])=O)C(C(C)C)=C1 HPWMVNFJSFHJIW-UHFFFAOYSA-M 0.000 description 1
- SCRWQCKSJIHKKV-UHFFFAOYSA-M potassium;2,4,6-trimethylbenzenesulfinate Chemical compound [K+].CC1=CC(C)=C(S([O-])=O)C(C)=C1 SCRWQCKSJIHKKV-UHFFFAOYSA-M 0.000 description 1
- YVHWGMMGEAQQRT-UHFFFAOYSA-M potassium;4-methylbenzenesulfinate Chemical compound [K+].CC1=CC=C(S([O-])=O)C=C1 YVHWGMMGEAQQRT-UHFFFAOYSA-M 0.000 description 1
- LZSBNSVOXWMXLL-UHFFFAOYSA-M potassium;benzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=CC=C1 LZSBNSVOXWMXLL-UHFFFAOYSA-M 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- SLUHLANJIVXTRQ-UHFFFAOYSA-N pyridin-2-ylthiourea Chemical compound NC(=S)NC1=CC=CC=N1 SLUHLANJIVXTRQ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- VFTILSBBLXWMQK-UHFFFAOYSA-M sodium;1-cyclohexyl-5-ethyl-4,6-dioxopyrimidin-2-olate Chemical compound [Na+].O=C1C(CC)C(=O)[N-]C(=O)N1C1CCCCC1 VFTILSBBLXWMQK-UHFFFAOYSA-M 0.000 description 1
- KNHRGMOGYVTHPU-UHFFFAOYSA-M sodium;2,4,6-triethylbenzenesulfinate Chemical compound [Na+].CCC1=CC(CC)=C(S([O-])=O)C(CC)=C1 KNHRGMOGYVTHPU-UHFFFAOYSA-M 0.000 description 1
- GRBCNEIBDFNEES-UHFFFAOYSA-M sodium;2,4,6-trimethylbenzenesulfinate Chemical compound [Na+].CC1=CC(C)=C(S([O-])=O)C(C)=C1 GRBCNEIBDFNEES-UHFFFAOYSA-M 0.000 description 1
- LCJZXLDPIPCLEJ-UHFFFAOYSA-M sodium;acetyl(phenyl)phosphinate Chemical compound [Na+].CC(=O)P([O-])(=O)C1=CC=CC=C1 LCJZXLDPIPCLEJ-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 description 1
- 229940041260 vanadyl sulfate Drugs 0.000 description 1
- 229910000352 vanadyl sulfate Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- QVOIJBIQBYRBCF-UHFFFAOYSA-H yttrium(3+);tricarbonate Chemical compound [Y+3].[Y+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O QVOIJBIQBYRBCF-UHFFFAOYSA-H 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- QSGNKXDSTRDWKA-UHFFFAOYSA-N zirconium dihydride Chemical compound [ZrH2] QSGNKXDSTRDWKA-UHFFFAOYSA-N 0.000 description 1
- 229910000568 zirconium hydride Inorganic materials 0.000 description 1
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
Abstract
Description
〔1〕一般式(1)で表されるリン酸二水素モノエステル基含有重合性単量体(A)、および一般式(2)で表されるリン酸二水素モノエステル基含有化合物(B)を含む、歯科用接着性組成物;
〔2〕リン酸二水素モノエステル基含有重合性単量体(A)と共重合可能な重合性単量体(C)を含む、前記〔1〕に記載の歯科用接着性組成物;
〔3〕重合開始剤(D)をさらに含む、前記〔1〕または〔2〕に記載の歯科用接着性組成物;
〔4〕前記一般式(1)中のX1および前記一般式(2)中のX2が同一である、前記〔1〕から〔3〕のいずれかに記載の歯科用接着性組成物;
〔5〕前記リン酸二水素モノエステル基含有化合物(B)の含有量が、前記リン酸二水素モノエステル基含有重合性単量体(A)100質量部に対して、0.05〜5.0質量部である、前記〔1〕〜〔4〕のいずれかに記載の歯科用接着性組成物;
〔6〕X1およびX2が、それぞれ独立して、直鎖状の無置換の炭素数8〜16のアルキレン基である、前記〔1〕〜〔5〕のいずれかに記載の歯科用接着性組成物;
〔7〕リン酸二水素モノエステル基含有重合性単量体(A)と共重合可能な重合性単量体(C)を含み、前記重合性単量体(C)が、酸性基を有しない疎水性重合性単量体(C−1)を含む、前記〔1〕〜〔6〕のいずれかに記載の歯科用接着性組成物
を包含する。
リン酸二水素モノエステル基含有重合性単量体(A)は、サンドブラスト処理されたジルコニアに対して化学的に結合すると同時に、重合可能であり硬化作用も付与する。また、リン酸二水素モノエステル基含有化合物(B)と併用することで、長い炭素鎖を有することからサンドブラスト処理されたジルコニア表面に規則的に配列される。そのため、サンドブラスト処理されたジルコニアに対して高い初期接着力のみならず、高い接着耐久性を示す。
リン酸二水素モノエステル基含有化合物(B)はジルコニアと化学的に結合する。また、リン酸二水素モノエステル基含有化合物(B)は、リン酸二水素モノエステル基含有重合性単量体(A)と同様の長い炭素鎖を有しており、かつ末端の水酸基がリン酸二水素モノエステル基含有重合性単量体(A)の(メタ)アクリロイルオキシ基に含まれる酸素原子と水素結合を形成することから、サンドブラスト処理されたジルコニア表面において、リン酸二水素モノエステル基含有重合性単量体(A)との間に適度に配列されると推定される。そのため、サンドブラスト処理されたジルコニアに対して高い初期接着力のみならず、高い接着耐久性を示す。
本発明の歯科用接着性組成物は、接着性および機械的強度の観点からリン酸二水素モノエステル基含有重合性単量体(A)と共重合可能な重合性単量体(C)(以下、単に「重合性単量体(C)」と略することがある)を含むことが好ましい。当該重合性単量体(C)としては公知の重合性単量体を使用することができ、例えば、酸性基を有しない疎水性重合性単量体(C−1)、酸性基を有しない親水性重合性単量体(C−2)などが挙げられ、硬化物の機械的強度、取り扱い性などの点から、当該重合性単量体(C)が、酸性基を有しない疎水性重合性単量体(C−1)を含むことが好ましい。重合性単量体(C)は、1種を単独で使用してもよいし、2種以上を併用してもよく、例えば、酸性基を有しない疎水性重合性単量体(C−1)と酸性基を有しない親水性重合性単量体(C−2)とを併用してもよい。なお、本発明における重合性単量体(C)には、リン酸二水素モノエステル基含有重合性単量体(A)に該当する重合性単量体は含まれない。
本発明の歯科用接着性組成物が酸性基を有しない疎水性重合性単量体(C−1)を含むことにより、硬化物(歯科用接着性組成物が硬化してなる硬化物)の機械的強度、取り扱い性などを向上させることができる。酸性基を有しない疎水性重合性単量体(C−1)としては、酸性基を有さず、重合性基を有するラジカル重合性単量体が好ましい。当該重合性基としては、ラジカル重合が容易であることなどから、(メタ)アクリロイル基、(メタ)アクリルアミド基が好ましい。酸性基を有しない疎水性重合性単量体(C−1)としては、25℃における水に対する溶解度が10質量%未満のものを用いることができ、例えば、単官能性重合性単量体、芳香族系の二官能性単量体、脂肪族系の二官能性単量体、三官能性以上の単量体といった架橋性重合性単量体などが挙げられる。
これらの中でも、2,2−ビス〔4−(3−メタクリロイルオキシ−2−ヒドロキシプロポキシ)フェニル〕プロパン、2,2−ビス(4−(メタ)アクリロイルオキシエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシポリエトキシフェニル)プロパン(エトキシ基の平均付加モル数が2.6のもの)、2,2−ビス(4−(メタ)アクリロイルオキシジエトキシフェニル)プロパン、2,2−ビス(4−(メタ)アクリロイルオキシトリエトキシフェニル)プロパン、2,2−ビス(4−(メタ)アクリロイルオキシテトラエトキシフェニル)プロパン、2,2−ビス(4−(メタ)アクリロイルオキシペンタエトキシフェニル)プロパンが好ましく、2,2−ビス〔4−(3−メタクリロイルオキシ−2−ヒドロキシプロポキシ)フェニル〕プロパン、2,2−ビス(4−メタクリロイルオキシポリエトキシフェニル)プロパン(エトキシ基の平均付加モル数が2.6のもの)がより好ましい。
本発明のある実施形態としては、酸性基を有しない親水性重合性単量体(C−2)を含む歯科用接着性組成物が挙げられる。本発明の歯科用接着性組成物を歯質に適用する場合、酸性基を有しない親水性重合性単量体(C−2)を含むことにより、歯科用接着性組成物中の成分が歯質へ浸透するのを促進することができると共に、それ自体も歯質に浸透して歯質中の有機成分(コラーゲン等)に接着することができる。酸性基を有しない親水性重合性単量体(C−2)としては、酸性基を有さず、重合性基を有するラジカル重合性単量体が好ましい。当該重合性基としては、ラジカル重合が容易であることなどから、(メタ)アクリロイル基、(メタ)アクリルアミド基が好ましい。酸性基を有しない親水性重合性単量体(C−2)としては、25℃における水に対する溶解度が10質量%以上のものを用いることができ、当該溶解度が30質量%以上のものが好ましく、25℃において水に任意の割合で溶解可能なものがより好ましい。
本発明の歯科用接着性組成物は、接着性の観点から、重合開始剤(D)をさらに含むことが好ましい。当該重合開始剤(D)としては公知の重合開始剤を使用することができ、例えば、光重合開始剤(D−1)、化学重合開始剤(D−2)などを使用することができる。重合開始剤(D)は、1種を単独で使用してもよいし、2種以上を併用してもよく、例えば、光重合開始剤(D−1)と化学重合開始剤(D−2)とを併用してもよい。
光重合開始剤(D−1)としては、例えば、(ビス)アシルホスフィンオキシド類(その塩を含む)、チオキサントン類(第4級アンモニウム塩等の塩を含む)、ケタール類、α−ジケトン類、クマリン類、アントラキノン類、ベンゾインアルキルエーテル類、α−アミノケトン系化合物などが挙げられる。
化学重合開始剤(D−2)としては従来公知のものを用いることができ、具体的には有機過酸化物および無機過酸化物が挙げられる。
本発明の歯科用接着性組成物は、重合促進剤(E)をさらに含むことができる。当該重合促進剤(E)は上記重合開始剤(D)と共に用いることが好ましい。当該重合促進剤(E)としては公知の重合促進剤を使用することができ、例えば、アミン類、スルフィン酸類(塩を含む)、ボレート化合物、バルビツール酸誘導体、トリアジン化合物、銅化合物、スズ化合物、バナジウム化合物、ハロゲン化合物、アルデヒド類、チオール化合物、亜硫酸塩、亜硫酸水素塩、チオ尿素化合物などが挙げられる。重合促進剤(E)は、1種を単独で使用してもよいし、2種以上を併用してもよい。
本発明の歯科用接着性組成物に、実施形態に応じて、さらにフィラー(F)を配合してもよい。フィラー(F)としては、通常、有機フィラー、無機フィラーおよび有機−無機複合フィラーに大別される。有機フィラーの素材としては、例えばポリメタクリル酸メチル、ポリメタクリル酸エチル、メタクリル酸メチル−メタクリル酸エチル共重合体、架橋型ポリメタクリル酸メチル、架橋型ポリメタクリル酸エチル、ポリアミド、ポリ塩化ビニル、ポリスチレン、クロロプレンゴム、ニトリルゴム、エチレン−酢酸ビニル共重合体、スチレン−ブタジエン共重合体、アクリロニトリル−スチレン共重合体、アクリロニトリル−スチレン−ブタジエン共重合体などが挙げられ、これらは1種を単独で用いてもよく、2種以上の混合物として用いることができる。有機フィラーの形状は特に限定されず、フィラーの粒子径を適宜選択して使用することができる。得られる歯科用接着性組成物のハンドリング性および機械的強度などの観点から、前記有機フィラーの平均粒子径は、0.001〜50μmが好ましく、0.001〜10μmがより好ましい。
本発明の歯科用接着性組成物は、その具体的な実施形態によっては、溶媒(G)を含むことが好ましい。溶媒(G)としては、水、有機溶媒、およびこれらの混合溶媒等が挙げられる。
本発明の歯科用接着性組成物は、さらにフッ素イオン放出性物質(H)を含んでいてもよい。フッ素イオン放出性物質(H)を配合することによって、歯質に耐酸性を付与することができる歯科用接着性組成物が得られる。前記フッ素イオン放出性物質(H)としては、例えば、フッ化ナトリウム、フッ化カリウム、モノフルオロリン酸ナトリウム、フッ化リチウム、フッ化イッテルビウムなどの金属フッ化物などが挙げられる。上記フッ素イオン放出性物質(H)は、1種を単独で配合してもよく、2種以上を組み合わせて配合してもよい。
歯科用プライマーは、酸性基含有重合性単量体を含む公知のプライマーにおいて、酸性基含有重合性単量体の一部または全部を本発明のリン酸二水素モノエステル基含有重合性単量体(A)、およびリン酸二水素モノエステル基含有化合物(B)に置き換えることで構成することができる。歯科用プライマーに用いる場合の歯科用接着性組成物(以下、単に「プライマー組成物」と略すことがある)の例としては、リン酸二水素モノエステル基含有重合性単量体(A)、リン酸二水素モノエステル基含有化合物(B)、および溶媒(G)を含むプライマー組成物が挙げられる。また、他の好適なプライマー組成物としては、前記したプライマー組成物において、さらに重合性単量体(C)を含むもの、ならびに、さらに重合開始剤(D)および重合促進剤(E)を含むものが挙げられる。さらに、他の好適なプライマー組成物としては、前記したいずれかのプライマー組成物が、重合性単量体成分の全量100質量部において、リン酸二水素モノエステル基含有重合性単量体(A)、およびリン酸二水素モノエステル基含有化合物(B)との混合物0.1〜100質量部、ならびに溶媒(G)6〜3500質量部を含むことが好ましく、リン酸二水素モノエステル基含有重合性単量体(A)、およびリン酸二水素モノエステル基含有化合物(B)との混合物0.25〜50質量部、ならびに溶媒(G)7〜2000質量部を含むことがより好ましく、リン酸二水素モノエステル基含有重合性単量体(A)、およびリン酸二水素モノエステル基含有化合物(B)との混合物0.5〜25質量部、重合性単量体(C)20〜99質量部、ならびに溶媒(G)7〜2000質量部を含むことがさらに好ましい。さらに、他の好適なプライマー組成物としては、前記した重合開始剤(D)および重合促進剤(E)を含むプライマー組成物が、重合性単量体成分の全量100質量部に対し、重合開始剤(D)0.001〜30質量部および重合促進剤(E)0.001〜30質量部を含むことが好ましく、重合開始剤(D)0.05〜20質量部および重合促進剤(E)0.05〜20質量部を含むことがより好ましい。また、前記したいずれかのプライマー組成物は、粘度調整などの目的で、重合性単量体成分の全量100質量部に対し、フィラー(F)を0〜5質量部含んでもよい。
本発明において、歯科用接着性組成物を歯科用セメントとして用いることも好適な実施形態の一つである。歯科用セメントとしては、レジンセメント、レジン強化型グラスアイオノマーセメントなどが好適なものとして例示される。歯科用セメントは、セルフエッチングプライマーなどを前処理剤として用いてもよい。歯科用セメントに用いる場合の歯科用接着性組成物(以下、単に「歯科用セメント」と略すことがある)の例としては、リン酸二水素モノエステル基含有重合性単量体(A)、リン酸二水素モノエステル基含有化合物(B)、重合性単量体(C)、重合開始剤(D)、重合促進剤(E)およびフィラー(F)を含むものが好ましい。また、他の好適な歯科用セメントとしては、前記した歯科用セメントにおいて、前記重合性単量体(C)が、酸性基を有しない疎水性重合性単量体(C−1)を含むものが挙げられる。さらに、他の好適な歯科用セメントとしては、前記したいずれかの歯科用セメントにおいて、前記重合性単量体(C)が、酸性基を有しない親水性重合性単量体(C−2)を含むものが挙げられる。さらに、他の好適な歯科用セメントとしては、前記したいずれかの歯科用セメントにおいて、重合開始剤(D)が化学重合開始剤(D−2)を含むものが挙げられる。また、他の好適な歯科用セメントとしては、前記したいずれかの歯科用セメントにおいて、重合開始剤(D)が光重合開始剤(D−1)および化学重合開始剤(D−2)を含む、デュアルキュア型のものが挙げられる。また、前記したいずれかの歯科用セメントは、第1材と第2材に分けられた2材型(2ペースト型)であってもよい。この場合、重合開始剤(D)と重合促進剤(E)は、第1材が重合開始剤(D)(例えば、化学重合開始剤(D−2))を含有し、第2材が重合促進剤(E)を含有するように、別々に配合することが好ましい。
MDP:10−メタクリロイルオキシデシルジヒドロジェンホスフェート
MOP:8−メタクリロイルオキシオクチルジヒドロジェンホスフェート
HDP:10−ヒドロキシデシルジヒドロジェンホスフェート
HOP:8−ヒドロキシオクチルジヒドロジェンホスフェート
(i)酸性基を有しない疎水性重合性単量体(C−1)
Bis−GMA:2,2−ビス〔4−(3−メタクリロイルオキシ−2−ヒドロキシプロポキシ)フェニル〕プロパン
D2.6E:2,2−ビス(4−メタクリロイルオキシポリエトキシフェニル)プロパン(エトキシ基の平均付加モル数が2.6のもの)
3G:トリエチレングリコールジメタクリレート
MAEA:N−メタクリロイルオキシエチルアクリルアミド
HEMA:2−ヒドロキシエチルメタクリレート
DEAA:N,N−ジエチルアクリルアミド
(i)光重合開始剤(D−1)
CQ:DL−カンファーキノン
BAPO:ビス(2,4,6−トリメチルベンゾイル)フェニルホスフィンオキシド
(ii)化学重合開始剤(D−2)
BPB:t−ブチルペルオキシベンゾエート
BPO:ベンゾイルペルオキシド
KPS:ペルオキソ二硫酸カリウム
DABE:4−(N,N−ジメチルアミノ)安息香酸エチル
DEPT:N,N−ジ(2−ヒドロキシエチル)−p−トルイジン
TPSS:2,4,6−トリイソプロピルベンゼンスルフィン酸ナトリウム
無機フィラー1:日本アエロジル株式会社製、微粒子シリカ「AEROSIL(登録商標) R 972」、平均粒子径:16nm
無機フィラー2:日本アエロジル株式会社製、酸化アルミニウム「AEROXIDE(登録商標)AluC」、平均粒子径:13nm
無機フィラー3:シラン処理珪石粉
珪石粉(株式会社ニッチツ製、商品名:ハイシリカ)をボールミルで粉砕し、粉砕珪石粉を得た。得られた粉砕珪石粉の平均粒子径をレーザー回折式粒度分布測定装置(株式会社島津製作所製、型式「SALD−2300」)を用いて測定したところ、2.2μmであった。この粉砕珪石粉100質量部に対して、常法により4質量部のγ−メタクリロイルオキシプロピルトリメトキシシランで表面処理を行い、シラン処理珪石粉を得た。
無機フィラー4:シラン処理バリウムガラス粉
バリウムガラス(エステック社製、商品名「E−3000」)をボールミルで粉砕し、バリウムガラス粉を得た。得られたバリウムガラス粉の平均粒子径をレーザー回折式粒度分布測定装置(株式会社島津製作所製、型式「SALD−2300」)を用いて測定したところ、2.4μmであった。このバリウムガラス粉100質量部に対して常法により3質量部のγ−メタクリロイルオキシプロピルトリメトキシシランで表面処理を行い、シラン処理バリウムガラス粉を得た。
BHT:2,6−ジ−t−ブチル−4−メチルフェノール(安定剤(重合禁止剤))
300mLの4つ口フラスコにTHF100mL、1,10−デカンジオール21.6g(0.124モル)、トリエチルアミン13.8g(0.136モル)を順次仕込み、−40℃まで冷却した。次いで、オキシ塩化リン19.0g(0.124モル)のTHF30mL溶液を1時間かけて4つ口フラスコ内に滴下した後、得られた溶液を−30℃で3時間撹拌した。次に、室温まで昇温させ水200mLに注入し、80℃まで加熱し5時間撹拌した。室温まで冷却し酢酸エチル150mLで3回抽出した。硫酸マグネシウムで乾燥後、減圧濃縮した。得られた残渣の一部を分取薄層クロマトグラフィー(以下、「PTLC」と略す)で分離精製し、目的化合物である10−ヒドロキシデシルジヒドロジェンホスフェート(HDP)1.1gを無色油状物として得た。
1H−NMR(400MHz,CDCl3):1.17−1.78(m,18H),3.51(m,2H),4.71(s,1H)
300mLの4つ口フラスコにTHF100mL、1,8−オクタンジオール18.1g(0.124モル)、トリエチルアミン13.8g(0.136モル)を順次仕込み、−40℃まで冷却した。次いで、オキシ塩化リン19.0g(0.124モル)のTHF30mL溶液を1時間かけて4つ口フラスコ内に滴下した後、得られた溶液を−30℃で3時間撹拌した。次に、室温まで昇温させ水200mLに注入し、80℃まで加熱し5時間撹拌した。室温まで冷却し酢酸エチル150mLで3回抽出した。硫酸マグネシウムで乾燥後、減圧濃縮した。得られた残渣の一部をPTLCで分離精製し、目的化合物である8−ヒドロキシオクチルジヒドロジェンホスフェート(HOP)0.8gを無色油状物として得た。
1H−NMR(400MHz,CDCl3):1.15−1.76(m,14H),3.51(s,2H),4.68(s,1H)
<実施例1−1〜1−9および比較例1−1>
前記した成分を用いて、表1に記載の各成分を常温下で混合することにより、実施例1−1〜1−9および比較例1−1の歯科用プライマー組成物を調製した。次いで、得られた歯科用プライマー組成物を用い、後述の方法に従って、サンドブラスト処理されたジルコニアに対する引張り接着強さを測定した。表1に、各実施例および比較例の歯科用プライマーの配合比(質量部)および試験結果を示す。
<実施例2−1〜2−10および比較例2−1>
前記した成分を用いて、表2に記載の各成分を常温下で混合および混練することにより、実施例2−1〜2−10および比較例2−1の2材型の歯科用セメントを調製した。次いで、これらの歯科用セメントを用い、後述の方法に従って、サンドブラスト処理されたジルコニアに対する引張り接着強さを測定した。表2に、各実施例および比較例の歯科用セメントの配合比(質量部)および試験結果を示す。
Claims (7)
- リン酸二水素モノエステル基含有重合性単量体(A)と共重合可能な重合性単量体(C)を含む、請求項1に記載の歯科用接着性組成物。
- 重合開始剤(D)をさらに含む、請求項1または2に記載の歯科用接着性組成物。
- 前記一般式(1)中のX1および前記一般式(2)中のX2が同一である、請求項1〜3のいずれか1項に記載の歯科用接着性組成物。
- 前記リン酸二水素モノエステル基含有化合物(B)の含有量が、前記リン酸二水素モノエステル基含有重合性単量体(A)100質量部に対して、0.05〜5.0質量部である、請求項1〜4のいずれか1項に記載の歯科用接着性組成物。
- X1およびX2が、それぞれ独立して、直鎖状の無置換の炭素数8〜16のアルキレン基である、請求項1〜5のいずれか1項に記載の歯科用接着性組成物。
- リン酸二水素モノエステル基含有重合性単量体(A)と共重合可能な重合性単量体(C)を含み、前記重合性単量体(C)が、酸性基を有しない疎水性重合性単量体(C−1)を含む、請求項1〜6のいずれか1項に記載の歯科用接着性組成物。
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