CN118043020A - Dental adhesive composition - Google Patents
Dental adhesive composition Download PDFInfo
- Publication number
- CN118043020A CN118043020A CN202280066283.2A CN202280066283A CN118043020A CN 118043020 A CN118043020 A CN 118043020A CN 202280066283 A CN202280066283 A CN 202280066283A CN 118043020 A CN118043020 A CN 118043020A
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- CN
- China
- Prior art keywords
- meth
- adhesive composition
- parts
- mass
- dental
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 98
- 239000003479 dental cement Substances 0.000 title claims abstract description 60
- 239000002253 acid Substances 0.000 claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 57
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 239000003999 initiator Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- -1 siloxanes Chemical class 0.000 abstract description 54
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract description 8
- 230000001070 adhesive effect Effects 0.000 description 58
- 239000000853 adhesive Substances 0.000 description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- 210000004268 dentin Anatomy 0.000 description 25
- 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 20
- 229930006711 bornane-2,3-dione Natural products 0.000 description 20
- CFKBCVIYTWDYRP-UHFFFAOYSA-N 10-phosphonooxydecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOP(O)(O)=O CFKBCVIYTWDYRP-UHFFFAOYSA-N 0.000 description 18
- 239000012153 distilled water Substances 0.000 description 18
- RMCCONIRBZIDTH-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 1,3-dioxo-2-benzofuran-5-carboxylate Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 RMCCONIRBZIDTH-UHFFFAOYSA-N 0.000 description 16
- 238000002156 mixing Methods 0.000 description 16
- 239000000919 ceramic Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 239000003505 polymerization initiator Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000000945 filler Substances 0.000 description 9
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 8
- 210000003298 dental enamel Anatomy 0.000 description 8
- 150000003512 tertiary amines Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000805 composite resin Substances 0.000 description 7
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical group OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 150000003585 thioureas Chemical class 0.000 description 7
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 150000001451 organic peroxides Chemical class 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 150000003682 vanadium compounds Chemical class 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 235000011180 diphosphates Nutrition 0.000 description 5
- 229940048084 pyrophosphate Drugs 0.000 description 5
- 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 4
- 239000000178 monomer Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000011247 coating layer Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005115 demineralization Methods 0.000 description 3
- 230000002328 demineralizing effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 2
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 2
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- GMEGXJPUFRVCPX-UHFFFAOYSA-N butylthiourea Chemical compound CCCCNC(N)=S GMEGXJPUFRVCPX-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000011350 dental composite resin Substances 0.000 description 2
- 239000005548 dental material Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005641 methacryl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000051 modifying effect Effects 0.000 description 2
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- JLAVFLRQAWOKRL-UHFFFAOYSA-N propyl 3-methylbut-2-enoate Chemical compound CCCOC(=O)C=C(C)C JLAVFLRQAWOKRL-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- MMEJYPZZFYTVLJ-WAYWQWQTSA-N (z)-2-(2-prop-2-enoyloxyethyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\CCOC(=O)C=C MMEJYPZZFYTVLJ-WAYWQWQTSA-N 0.000 description 1
- JAEZSIYNWDWMMN-UHFFFAOYSA-N 1,1,3-trimethylthiourea Chemical compound CNC(=S)N(C)C JAEZSIYNWDWMMN-UHFFFAOYSA-N 0.000 description 1
- JTXGASNAYIXEBQ-UHFFFAOYSA-N 1,1-didodecylthiourea Chemical compound CCCCCCCCCCCCN(C(N)=S)CCCCCCCCCCCC JTXGASNAYIXEBQ-UHFFFAOYSA-N 0.000 description 1
- FPZXQVCYHDMIIA-UHFFFAOYSA-N 1,1-diphenylthiourea Chemical compound C=1C=CC=CC=1N(C(=S)N)C1=CC=CC=C1 FPZXQVCYHDMIIA-UHFFFAOYSA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- XIBAZLLABMNRRJ-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.CC(C)C1=CC=C(C(C)C)C=C1 XIBAZLLABMNRRJ-UHFFFAOYSA-N 0.000 description 1
- VUVPNTYTOUGMDG-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-prop-2-enylthiourea Chemical compound OCCNC(=S)NCC=C VUVPNTYTOUGMDG-UHFFFAOYSA-N 0.000 description 1
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-UHFFFAOYSA-N 0.000 description 1
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- JKZGKJJRHXYLRI-UHFFFAOYSA-N 1-tert-butyl-3-propan-2-ylthiourea Chemical compound CC(C)NC(=S)NC(C)(C)C JKZGKJJRHXYLRI-UHFFFAOYSA-N 0.000 description 1
- DRIRMYPZOAOUPR-UHFFFAOYSA-N 10,10-dioxothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=C1 DRIRMYPZOAOUPR-UHFFFAOYSA-N 0.000 description 1
- YEZOVIIHKKPUOS-UHFFFAOYSA-N 10-oxothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)C2=C1 YEZOVIIHKKPUOS-UHFFFAOYSA-N 0.000 description 1
- NTMDDSQESSRCTM-UHFFFAOYSA-N 10-phosphonooxydecyl prop-2-enoate Chemical compound OP(O)(=O)OCCCCCCCCCCOC(=O)C=C NTMDDSQESSRCTM-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- YVJVQYNIANZFFM-UHFFFAOYSA-N 2-(4-methylanilino)ethanol Chemical compound CC1=CC=C(NCCO)C=C1 YVJVQYNIANZFFM-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
- LIZVXGBYTGTTTI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-UHFFFAOYSA-N 0.000 description 1
- LBNDGEZENJUBCO-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethyl]butanedioic acid Chemical compound CC(=C)C(=O)OCCC(C(O)=O)CC(O)=O LBNDGEZENJUBCO-UHFFFAOYSA-N 0.000 description 1
- KIWRLBQZUHYWJI-UHFFFAOYSA-N 2-[hydroxy(phenoxy)phosphoryl]oxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOP(=O)(O)OC1=CC=CC=C1 KIWRLBQZUHYWJI-UHFFFAOYSA-N 0.000 description 1
- RQFJTNXBAXGRSZ-UHFFFAOYSA-N 2-benzylanthracene-9,10-dione Chemical compound C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=1CC1=CC=CC=C1 RQFJTNXBAXGRSZ-UHFFFAOYSA-N 0.000 description 1
- SQOUGRMFFXWSRY-UHFFFAOYSA-N 2-chloro-7-(trifluoromethyl)thioxanthen-9-one Chemical compound C1=C(Cl)C=C2C(=O)C3=CC(C(F)(F)F)=CC=C3SC2=C1 SQOUGRMFFXWSRY-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- ASEUXRQULQEGGL-UHFFFAOYSA-N 2-decyl-2-prop-2-enoyloxypropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)(C(O)=O)OC(=O)C=C ASEUXRQULQEGGL-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- AUZRCMMVHXRSGT-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CC(C)CS(O)(=O)=O AUZRCMMVHXRSGT-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- DYRJLHNVMSBZLR-UHFFFAOYSA-N 2-nitrothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3SC2=C1 DYRJLHNVMSBZLR-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UXTGJIIBLZIQPK-UHFFFAOYSA-N 3-(2-prop-2-enoyloxyethyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(CCOC(=O)C=C)=C1C(O)=O UXTGJIIBLZIQPK-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- ZLTXRFUVPRWFGH-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid ethyl 4-(dimethylamino)benzoate Chemical compound C(C)OC(C1=CC=C(C=C1)N(C)C)=O.CN(C1=CC=C(C(=O)O)C=C1)C ZLTXRFUVPRWFGH-UHFFFAOYSA-N 0.000 description 1
- UNLGHUTUQNFLSO-UHFFFAOYSA-N 6-phosphonooxyhexyl prop-2-enoate Chemical compound OP(O)(=O)OCCCCCCOC(=O)C=C UNLGHUTUQNFLSO-UHFFFAOYSA-N 0.000 description 1
- GZEYLLPOQRZUDF-UHFFFAOYSA-N 7-(dimethylamino)-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(N(C)C)=CC=C21 GZEYLLPOQRZUDF-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
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- MRCMTIRVXOVDMR-UHFFFAOYSA-N [3-oxo-3-(5-prop-2-enoyloxypentoxy)propyl]phosphonic acid Chemical compound OP(O)(=O)CCC(=O)OCCCCCOC(=O)C=C MRCMTIRVXOVDMR-UHFFFAOYSA-N 0.000 description 1
- LIPZALUJBHGKGU-UHFFFAOYSA-N [3-oxo-3-(6-prop-2-enoyloxyhexoxy)propyl]phosphonic acid Chemical compound OP(O)(=O)CCC(=O)OCCCCCCOC(=O)C=C LIPZALUJBHGKGU-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound 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 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- LEEHHPPLIOFGSC-UHFFFAOYSA-N cyclohexylthiourea Chemical compound NC(=S)NC1CCCCC1 LEEHHPPLIOFGSC-UHFFFAOYSA-N 0.000 description 1
- 239000000001 dental powder Substances 0.000 description 1
- PSYDSRLQABJJAD-UHFFFAOYSA-N dodecylthiourea Chemical compound CCCCCCCCCCCCNC(N)=S PSYDSRLQABJJAD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XPKFLEVLLPKCIW-UHFFFAOYSA-N ethyl 4-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=C(N(CC)CC)C=C1 XPKFLEVLLPKCIW-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- ZFHOULOIWZOZQS-UHFFFAOYSA-N hexane;hydrogen peroxide Chemical compound OO.CCCCCC ZFHOULOIWZOZQS-UHFFFAOYSA-N 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 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
- 239000007800 oxidant agent Substances 0.000 description 1
- DYYSJNQVLWANCC-UHFFFAOYSA-N oxolan-2-ylmethylthiourea Chemical compound NC(=S)NCC1CCCO1 DYYSJNQVLWANCC-UHFFFAOYSA-N 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- KSOMQZOHPWJPMM-UHFFFAOYSA-N propyl 4-(diethylamino)benzoate Chemical compound CCCOC(=O)C1=CC=C(N(CC)CC)C=C1 KSOMQZOHPWJPMM-UHFFFAOYSA-N 0.000 description 1
- SCNYCWQULCHALD-UHFFFAOYSA-N propyl 4-(dimethylamino)benzoate Chemical compound CCCOC(=O)C1=CC=C(N(C)C)C=C1 SCNYCWQULCHALD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 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
- 239000003566 sealing material Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 238000002791 soaking Methods 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Dental Preparations (AREA)
Abstract
A dental adhesive composition comprising: (meth) acrylic acid esters having an acid group, and linear siloxanes represented by the following general formula (1),(In the above general formula (1), X 1～X6 is each independently an alkyl group having 1 to 6 carbon atoms or an ethylenically unsaturated group, m is an integer of 0 to 500, when m is 2 or more, X 3、X4 is the same or different in each repeating unit, Y 1、Y2 is each independently a linear or branched hydrocarbon group having 1 to 20 carbon atoms, Z 1～Z4 is each independently a hydrogen atom or an ethylenically unsaturated group, and at least 1 of X 1～X6 and Z 1～Z4 is an ethylenically unsaturated group).
Description
Technical Field
The present invention relates to an adhesive composition for dental use.
Background
In the dental field, with the popularization of dental restorative materials such as composite resins, dental adhesive compositions capable of obtaining an adhesive effect between dentin and dental restorative materials are used. For example, an adhesive composition for dental use containing a phosphoric acid group-containing polymerizable monomer is disclosed (for example, see patent document 1).
In addition, a dental composition is used in which a uniform coating surface is formed on dentin (enamel, ivory) as an adherend. For example, a dental composition containing a copolymer having a monomer unit having a perfluoroalkyl group at a position at least not at the terminal, or a copolymer having a monomer unit having a siloxy group at a position at least not at the terminal is disclosed (for example, refer to patent document 2).
Prior art literature
Patent literature
Patent document 1: international publication No. 2019/203356;
patent document 2: japanese patent application laid-open No. 2020-2076.
Disclosure of Invention
Problems to be solved by the invention
However, in the conventional adhesive composition for dental use, the adhesion between dentin and ceramic is not sufficiently obtained.
The present invention aims to provide a dental adhesive composition which has excellent adhesion between dentin and ceramic.
Means for solving the problems
The dental adhesive composition according to one embodiment of the present invention is a dental adhesive composition comprising: (meth) acrylic acid esters having an acid group, and linear siloxanes represented by the following general formula (1).
In the general formula (1), X 1～X6 is each independently an alkyl group having 1 to 6 carbon atoms or an ethylenically unsaturated group, m is an integer of 0 to 500, X 3、X4 is the same or different in each repeating unit when m is 2 or more, Y 1、Y2 is each independently a linear or branched hydrocarbon group having 1 to 20 carbon atoms, Z 1～Z4 is each independently a hydrogen atom or an ethylenically unsaturated group, and at least one of X 1～X6 and Z 1～Z4 is an ethylenically unsaturated group.
ADVANTAGEOUS EFFECTS OF INVENTION
According to one embodiment of the present invention, a dental adhesive composition having excellent adhesion between dentin and ceramic can be provided.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail.
The adhesive composition for dental use of the present embodiment contains a (meth) acrylate having an acid group and a linear siloxane having a predetermined structure.
In the present specification, (meth) acrylate means a monomer, oligomer or prepolymer of (meth) acrylate having one or more (meth) acryloyloxy groups. Here, (meth) acrylate refers to one or both of acrylate and methacrylate.
The siloxane has a structure represented by-silicon (Si) -oxygen (O) - [ -silicon (Si) -oxygen (O) - ] L-silicon (Si) - (L is an integer of 0 or more).
The (meth) acrylate having an acid group contained in the adhesive composition for dental use is not particularly limited, but is preferably, for example, a (meth) acrylate having an acid group such as a phosphoric acid group, a pyrophosphoric acid group, a thiophosphoric acid group, a carboxylic acid group, a sulfonic acid group, or a phosphonic acid group. In addition, the (meth) acrylate having an acid group may have a plurality of acid groups.
Examples of the (meth) acrylic acid ester having a phosphate group include 2- (meth) acryloyloxyethyl dihydrogen phosphate, bis [2- (meth) acryloyloxyethyl ] hydrogen phosphate, 2- (meth) acryloyloxyethyl phenyl hydrogen phosphate, 6- (meth) acryloyloxyhexyl dihydrogen phosphate, 6- (meth) acryloyloxyhexyl phenyl hydrogen phosphate, 10- (meth) acryloyloxydecyl dihydrogen phosphate, 1, 3-di (meth) acryloylpropane-2-phenyl hydrogen phosphate, and bis [5- {2- (meth) acryloyloxyethoxycarbonyl } heptyl ] hydrogen phosphate.
Examples of the (meth) acrylic acid ester having a pyrophosphoric acid group include bis [2- (meth) acryloyloxyethyl ] pyrophosphate, bis [4- (meth) acryloyloxybutyl ] pyrophosphate, bis [6- (meth) acryloyloxyhexyl ] pyrophosphate, bis [8- (meth) acryloyloxyoctyl ] pyrophosphate, and bis [10- (meth) acryloyloxydecyl ] pyrophosphate.
Examples of the (meth) acrylic acid ester having a phosphorothioate group include 2- (meth) acryloyloxyethyl dihydrophosphorothioate, 3- (meth) acryloyloxypropyl dihydrophosphorothioate, 4- (meth) acryloyloxybutyl dihydrophosphorothioate, 5- (meth) acryloyloxypentyl dihydrophosphorothioate, 6- (meth) acryloyloxyhexyl dihydrophosphorothioate, 7- (meth) acryloyloxyheptyl dihydrophosphorothioate, 8- (meth) acryloyloxyoctyl dihydrophosphorothioate, 9- (meth) acryloyloxynonyl dihydrophosphorothioate, 10- (meth) acryloyloxydecyl dihydrophosphorothioate, 11- (meth) acryloyloxyundecyl dihydrophosphorothioate, 12- (meth) acryloyloxydodecyl dihydrophosphorothioate, 13- (meth) acryloyloxytridecyl dihydrophosphorothioate, 14- (meth) acryloyloxytetradecyl dihydrophosphorothioate, 15- (meth) acryloyloxyheptyl dihydrophosphorothioate, 8- (meth) acryloyloxyoctyl dihydrophosphorothioate, 9- (meth) acryloyloxydecyl dihydrophosphorothioate, 11- (meth) acryloyloxyundecyl dihydrophosphorothioate, 12- (meth) acryloyloxydodecyl dihydrophosphorothioate, 13- (meth) acryloyloxytridecyl dihydrophosphorothioate, and octadecyl dihydrophosphorothioate, 20- (meth) acryloyloxy eicosanyl dihydro-phosphorothioate, and the like.
Examples of the (meth) acrylic acid ester having a carboxylic acid group include 2-methacryloxyethyl succinic acid, 4- (meth) acryloxyethyl trimellitic anhydride, 4- (meth) acryloxydecyl trimellitic acid, 4- (meth) acryloxydecyl trimellitic anhydride, 11- (meth) acryloxy1, 1-undecanedicarboxylic acid, 1, 4-di (meth) acryloxypyromellitic acid, 2- (meth) acryloxyethyl maleic acid, 2- (meth) acryloxyethyl phthalic acid, and 2- (meth) acryloxyethyl hexahydrophthalic acid.
Examples of the (meth) acrylate having a sulfonic acid group include 2- (meth) acrylamide-2-methylpropanesulfonic acid, styrenesulfonic acid, and 2-sulfoethyl (meth) acrylate.
Examples of the (meth) acrylate having a phosphonic acid group include 2- (meth) acryloyloxyethyl phenyl phosphonate, 5- (meth) acryloyloxypentyl-3-phosphonopropionate, 6- (meth) acryloyloxyhexyl-3-phosphonopropionate, 10- (meth) acryloyloxydecyl-3-phosphonopropionate, 6- (meth) acryloyloxyhexyl-3-phosphonoacetate, and 10- (meth) acryloyloxydecyl-3-phosphonoacetate.
These (meth) acrylic acid esters having an acid group may be used alone or in combination of 1 or more than 2.
Among these (meth) acrylates having an acid group, from the viewpoint of solubility of a coating layer on a tooth surface of a dental adhesive composition or decalcification of dentin, particularly adhesion to enamel, it is preferable to have 1 or more (meth) acrylates selected from a phosphate group, a thiophosphate group and a carboxylate group.
Further, from the viewpoint of improving the adhesiveness of the dental adhesive composition, the (meth) acrylate having an acid group is preferably 1 or more selected from 10-Methacryloyloxydecyl Dihydrogen Phosphate (MDP), 4-methacryloyloxyethyl trimellitic anhydride (4-META), and the like.
The content of the (meth) acrylate having an acid group in the adhesive composition for dental use is not particularly limited, but is preferably 0.1 mass% or more and 40 mass% or less, more preferably 1 mass% or more and 25 mass% or less, and still more preferably 5 mass% or more and 25 mass% or less.
If the content of the (meth) acrylate having an acid group in the dental adhesive composition is 0.1 mass% or more, the demineralization force of the dental adhesive composition to dentin is further improved, and if it is 40 mass% or less, the curability of the dental adhesive composition is improved.
The siloxane having a predetermined structure contained in the adhesive composition for dental use is a linear siloxane represented by the following general formula (1).
In the general formula (1), each X 1～X6 is independently an alkyl group having 1 to 6 carbon atoms or an ethylenically unsaturated group. Here, each independently means that the structure and the number of carbon atoms between X 1～X6 may be different.
The upper limit of the number of carbon atoms in X 1～X6 is not particularly limited, but is preferably 4, more preferably 3, and further preferably 2.
The alkyl group having 1 to 6 carbon atoms in X 1～X6 is not particularly limited, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl, 3-methylpentyl, 2-ethylbutyl, 1, 2-dimethylbutyl, 2, 3-dimethylbutyl, and n-heptyl.
The ethylenically unsaturated group is not particularly limited, and examples thereof include a vinyl group, an allyl group, an acryl group (also referred to as an acryl group), a methacryl group (also referred to as a methacryl group), and the like. The ethylenically unsaturated group may have an alkylene group having 1 to 6 carbon atoms.
In the general formula (1), m is an integer of 0 to 500, preferably 0 to 300, more preferably 0 to 100, still more preferably 0 to 50, and particularly preferably 0 to 10.
When m is 2 or more, X 3、X4 may be the same or different in each repeating unit. Specifically, for example, when m is 2, it may be an alkyl group having 1 carbon atom of one of the repeating units X 3 and X 4, and an alkyl group having 2 carbon atoms of the other repeating units X 3 and X 4.
In the general formula (1), Y 1、Y2 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms independently. In addition, Y 1、Y2 may have an ether linkage.
The term "linear or branched hydrocarbon group having 1 to 20 carbon atoms" as used herein means a linear hydrocarbon group having 1 to 20 carbon atoms or a branched hydrocarbon group having 1 to 20 carbon atoms.
The upper limit of the number of carbon atoms in Y 1、Y2 is preferably 16, more preferably 8, and further preferably 2.
The linear or branched hydrocarbon group having 1 to 20 carbon atoms in Y 1、Y2 is not particularly limited, and examples thereof include a structure represented by C αH2α、CαH2α-1 (α is an integer of 1 to 20).
In the general formula (1), each Z 1～Z4 is independently a hydrogen atom or an ethylenically unsaturated group. For example, when one of Z 1 and Z 2 is hydrogen and the other is an ethylenically unsaturated group, the ethylenically unsaturated group is a terminal group of a linear siloxane represented by the general formula (1). When both Z 1 and Z 2 are hydrogen atoms, Y 1 is a terminal group of the linear siloxane represented by the general formula (1).
When either one of Z 3 and Z 4 is hydrogen and the other is an ethylenically unsaturated group, the ethylenically unsaturated group becomes a terminal group of the linear siloxane represented by the general formula (1). When both Z 3 and Z 4 are hydrogen atoms, Y 2 is a terminal group of the linear siloxane represented by the general formula (1).
In formula (1), at least one of X 1～X6 and Z 1～Z4 is an ethylenically unsaturated group.
That is, the linear siloxane represented by the general formula (1) may have an ethylenically unsaturated group at one end of the siloxane, may have an ethylenically unsaturated group at both ends, or may have an ethylenically unsaturated group in a side chain.
The linear siloxane represented by the general formula (1) is preferable because it has an ethylenically unsaturated group in a side chain, and thus, it has a surface modifying effect, and the crosslinking density and hardness are improved. In addition, in the case where one or both ends of the siloxane have an ethylenically unsaturated group, the surface modifying effect, the crosslinking density and the hardness can be improved.
Specific examples of the linear siloxane having at least 1 ethylenically unsaturated group include linear siloxane having (meth) acryloyl groups at both ends of the siloxane, linear siloxane having (meth) acryloyloxy groups at one end of the siloxane, and linear siloxane having (meth) acryloyloxy groups in side chains of the siloxane.
Examples of the linear siloxane having (meth) acryloyl groups at both ends thereof include "X-22-164"、"X-22-164AS"、"X-22-164A"、"X-22-164B"、"X-22-164C"、"X-22-164E"、"KP-410"、"KP-411"、"KP-412"、"KP-413"、"KP-414"、"KP-415"、"KP-423"( or more, and "DMS-C21", "DMS-E21", "DMS-T21", "DMS-U21" (manufactured by Gelest corporation).
Examples of the linear siloxane having a (meth) acryloyloxy group at one end include "X-22-174ASX", "X-22-174BX", "KF-2012", "X-22-2426", "X-22-2404", "KP-416", "KP-418", "KP-422" (manufactured by the above-mentioned Xinyue chemical industries, ltd.).
Examples of the linear siloxane having a (meth) acryloyloxy group in its side chain include "KP-420" (manufactured by Xin Yue chemical industries Co., ltd.).
These linear siloxanes may be used singly or in combination of 1 or more than 2.
The content of the linear siloxane in the dental adhesive composition is not particularly limited, but is preferably 0.01 mass% or more and 30 mass% or less, more preferably 0.1 mass% or more and 25 mass% or less, and still more preferably 0.5 mass% or more and 20 mass% or less.
If the content of the linear siloxane in the dental adhesive composition is 0.01 mass% or more, the adhesion strength to ceramics is improved by lowering the surface tension, and if it is 30 mass% or less, the hydrophilicity of the dental adhesive composition is maintained, and the adhesion to dentin is improved.
The dental adhesive composition of the present embodiment may contain a (meth) acrylate having no acid group.
The (meth) acrylate having no acid group is not particularly limited. Examples thereof include methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, hydroxypropyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, glycidyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxy-1, 3-di (meth) acryloxypropane, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate, 1, 4-di (meth) acrylate, 1, 6-butanediol di (meth) acrylate, trimethylolpropane, and trimethylolpropane (meth) acrylate, pentaerythritol tri (meth) acrylate, trimethylol methane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, polybutylene glycol di (meth) acrylate, bisphenol A diglycidyl (meth) acrylate, di-2- (meth) acryloyloxyethyl-2, 4-trimethylhexamethylene dicarbamate, 1,3, 5-tris [1, 3-bis { (meth) acryloyloxy } -2-propoxyaminohexane ] -1,3,5- (1H, 3H, 5H) triazine-2, 4, 6-trione, 2-bis [4- (3- (meth) acryloyloxy-2-hydroxypropyl) phenyl ] propane, N' - (2, 4-trimethylhexamethylene) bis [2- (aminocarboxyl) propane-1, 3-diol ] tetramethyl acrylate, and the like.
These (meth) acrylic acid esters having no acid group may be used alone or in combination of 1 or more than 2.
The (meth) acrylate having no acid group is preferably 2-hydroxy-1, 3-dimethylacryloxypropane (GDMA), triethylene glycol dimethacrylate (TEGDMA) or bisphenol a diglycidyl methacrylate from the viewpoints of improving the mechanical strength of a cured product of the adhesive composition for dental use and improving the adhesion to ceramics and dentin.
The content of the (meth) acrylate having no acid group in the dental adhesive composition may be 3 mass% or more and 50 mass% or less, preferably 5 mass% or more and 40 mass% or less, and more preferably 10 mass% or more and 30 mass% or less.
If the content of the (meth) acrylate having no acid group in the dental adhesive composition is 3 mass% or more, the workability of the dental adhesive composition can be improved. In addition, if the content of the (meth) acrylate having no acid group in the dental adhesive composition is 50 mass% or less, the mechanical strength of the dental polymerizable composition can be improved.
The dental adhesive composition of the present embodiment may contain other components as long as the object of the present invention is not impaired. Examples of the other components contained in the dental adhesive composition include a polymerization initiator, a polymerization inhibitor, a filler, and a solvent. Further, as the polymerization initiator, a chemical polymerization initiator and a photopolymerization initiator can be mentioned.
The chemical polymerization initiator is not particularly limited, and for example, thiourea derivatives, vanadium compounds, tertiary amines, and organic peroxides can be used.
Even in the chemical polymerization initiator, the thiourea derivative acts as a reducing agent.
The thiourea derivative is not particularly limited, and examples thereof include ethylene thiourea, N-methyl thiourea, N-ethyl thiourea, N-propyl thiourea, N-butyl thiourea, N-lauryl thiourea, N-phenyl thiourea, N-cyclohexyl thiourea, N-dimethyl thiourea, N-diethyl thiourea, N-dipropyl thiourea, N-dibutyl thiourea, N, N-dilaurylthiourea, N-diphenylthiourea, N-dicyclohexylthiourea, trimethylthiourea, tetramethylthiourea, N-acetylthiourea, N-benzoylthiourea, 1-allyl-3- (2-hydroxyethyl) -2-thiourea, 1- (2-tetrahydrofurfuryl) -2-thiourea, N-t-butyl-N' -isopropylthiourea, 2-pyridylthiourea and the like.
These thiourea derivatives may be used alone or in combination of 1 or more than 2. Among them, N-benzoylthiourea is preferable from the viewpoint of improving the curability of the dental adhesive composition.
The content of the thiourea derivative in the adhesive composition for dental use is not particularly limited, but is preferably 0.1% by mass or more and 5% by mass or less, more preferably 0.1% by mass or more and 3% by mass or less, and still more preferably 0.1% by mass or more and 1% by mass or less. If the content of the thiourea derivative in the adhesive composition for dental use is 0.1 mass% or more, the curability of the adhesive composition for dental use is further improved, and if it is 5 mass% or less, the solubility of the thiourea derivative in the adhesive composition for dental use with respect to the (meth) acrylate is improved.
The vanadium compound also acts as a reducing agent in the chemical polymerization initiator.
The vanadium compound is not particularly limited, and examples thereof include vanadyl oxalate, vanadyl acetylacetonate, vanadyl stearate, vanadyl naphtalate, vanadyl benzoylacetate, and the like.
These vanadium compounds may be used alone or in combination of 2 or more. Among them, vanadyl acetylacetonate is preferable in terms of curability of the dental adhesive composition.
The content of the vanadium compound in the adhesive composition for dental use is not particularly limited, but is preferably 0.001 mass% to 5 mass%, more preferably 0.0015 mass% to 1 mass%, and still more preferably 0.002 mass% to 0.1 mass%. The curing property of the adhesive composition for dental use is further improved if the content of the vanadium compound in the adhesive composition for dental use is 0.001 mass% or more, and the storage stability of the adhesive composition for dental use is further improved if it is 5 mass% or less.
Tertiary amines also function as reducing agents in chemical polymerization initiators. In addition, tertiary amines may also function as photopolymerization promoters.
The tertiary amine is not particularly limited, and examples thereof include aliphatic tertiary amines and aromatic tertiary amines.
Examples of the aliphatic tertiary amine include N, N-dimethylaminoethyl methacrylate and triethanolamine.
Examples of the aromatic tertiary amine include alkyl p-dialkylaminobenzoate, 7-dimethylamino-4-methylcoumarin, N-dimethylaniline, N-dibenzylamine, N-dimethyl-p-toluidine, N, N-diethyl-p-toluidine, N-bis (2-hydroxyethyl) -p-toluidine, N,2,4, 6-pentamethyl aniline, N,2, 4-tetramethylaniline, N-diethyl-2, 4, 6-trimethylaniline, and the like.
Among these tertiary amines, aromatic tertiary amines are preferable, and alkyl p-dialkylaminobenzoate is more preferable.
Examples of the alkyl p-dialkylaminobenzoate include methyl p-dimethylaminobenzoate, ethyl p-dimethylaminobenzoate (4-dimethylaminobenzoate) (EPA), propyl p-dimethylaminobenzoate, pentyl p-dimethylaminobenzoate, isopentyl p-dimethylaminobenzoate, ethyl p-diethylaminobenzoate, and propyl p-diethylaminobenzoate.
These tertiary amines may be used singly or in combination of 1 kind or 2 or more kinds. Among them, ethyl 4-dimethylaminobenzoate (EPA) is preferable from the viewpoint of improving the curability of the dental adhesive composition.
The content of the tertiary amine in the adhesive composition for dental use is not particularly limited, but is preferably 0.01 mass% to 10 mass%, more preferably 0.05 mass% to 8 mass%, and still more preferably 1 mass% to 5 mass%. If the content of the tertiary amine in the adhesive composition for dental use is 0.01 mass% or more, the curability of the adhesive composition for dental use is further improved, and if it is 10 mass% or less, the margin time for handling the adhesive composition for dental use is increased.
Organic peroxides also function as oxidizing agents in chemical polymerization initiators.
Examples of the organic peroxide include benzoyl peroxide, cumene hydroperoxide, t-butyl hydroperoxide, t-amyl hydroperoxide, 1, 3-tetramethylbutyl hydroperoxide, 2, 5-dimethyl-2, 5-di (hydroperoxide) hexane hydroperoxide, p-diisopropylbenzene monohydrogen peroxide, p-methane hydroperoxide, and pinane hydroperoxide.
These organic peroxides may be used singly or in combination of 2 or more. Among them, cumene hydroperoxide is preferable from the viewpoint of curability of the dental adhesive composition.
The content of the organic peroxide in the adhesive composition for dental use is not particularly limited, but is preferably 0.01 mass% to 10 mass%, more preferably 0.05 mass% to 5 mass%, and still more preferably 0.1 mass% to 3 mass%. If the content of the organic peroxide in the adhesive composition for dental use is 0.01 mass% or more, the curability of the adhesive composition for dental use is further improved, and if it is 10 mass% or less, the margin time for handling the adhesive composition for dental use becomes long.
Examples of photopolymerization initiators include, but are not particularly limited to, camphorquinone (CQ), 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide (TPO), phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide, benzyl ketal, diacetyl ketal, benzyl dimethyl ketal, benzyl diethyl ketal, benzyl bis (2-methoxyethyl) ketal, 4' -dimethyl (benzyl dimethyl ketal), anthraquinone, 1-chloroanthraquinone, 2-chloroanthraquinone, 1, 2-benzylanthraquinone, 1-hydroxyanthraquinone, 1-methylanthraquinone, 2-ethylanthraquinone, 1-bromoanthraquinone, thioxanthone, 2-isopropylthioxanthone, 2-nitrothioxanthone, 2-methylthioxanthone, 2, 4-dimethylthioxanthone, 2, 4-diisopropylthioxanthone, 2-chloro-7-trifluoromethylthioxanthone, thioxanthone-10, 10-dioxide, thioxanthone-10-oxide, benzoin-4-dimethyl ether, benzoin-2-benzoin, benzoin-2-ethyl ether, benzoin-2-benzoin, benzoin-4-diethyl ether, and benzoin-4-diethyl ether.
These photopolymerization initiators may be used alone or in combination of 2 or more. Among them, camphorquinone (CQ) and 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide (TPO) are preferable from the viewpoint of improving the curability of the dental adhesive composition.
The content of the photopolymerization initiator in the adhesive composition for dental use is not particularly limited, but is preferably 0.01 mass% to 10 mass%, more preferably 0.05 mass% to 8 mass%, and still more preferably 1 mass% to 5 mass%. If the content of the photopolymerization initiator in the adhesive composition for dental use is 0.01 mass% or more, the curability of the adhesive composition for dental use is further improved, and if it is 10 mass% or less, the margin time for handling the adhesive composition for dental use is further improved.
The dental adhesive composition of the present embodiment is often cured by irradiation with ultraviolet rays or the like, and therefore, preferably contains a photopolymerization initiator as a polymerization initiator.
Examples of the polymerization inhibitor include dibutylhydroxytoluene (2, 6-di-t-butyl-p-cresol) (BHT) and 6-t-butyl-2, 4-xylenol.
These polymerization inhibitors may be used singly or in combination of 1 kind or 2 or more kinds. Among them, dibutylhydroxytoluene (BHT) is preferable from the viewpoint of improving the curability of the dental adhesive composition.
The content of the polymerization inhibitor in the adhesive composition for dental use is not particularly limited, but is preferably 0.01 mass% to 5 mass%, more preferably 0.05 mass% to 3 mass%, and still more preferably 0.1 mass% to 1 mass%. If the content of the polymerization inhibitor in the adhesive composition for dental use is 0.01 mass% or more and 5 mass% or less, the storage stability of the adhesive composition for dental use is improved.
The filler is not particularly limited, and examples thereof include colloidal silica, fine silica (hydrophobic fumed silica) whose surface has been subjected to hydrophobization, alumina, fluoroaluminosilicate glass, barium glass, and the like. Among them, hydrophobic fumed silica (e.g., aerosil (registered trademark)) is preferable. These fillers may be used singly or in combination of 2 or more.
The amount of the filler to be blended in the adhesive composition for dental use is, for example, preferably 0.1% by mass or more and 30% by mass or less, more preferably 0.5% by mass or more and 20% by mass or less, and still more preferably 1% by mass or more and 10% by mass or less.
If the amount of the filler in the dental adhesive composition is 0.1 mass% or more, the tackiness of the dental adhesive composition becomes high, and the workability of the dental adhesive composition can be improved. In addition, if the amount of filler in the dental adhesive composition is 30 mass% or less, the viscosity of the dental adhesive composition containing the glass does not become excessively high, and high operability of the dental adhesive composition can be maintained.
The solvent is not particularly limited, and examples thereof include 1 or more selected from water and organic solvents.
The water is not particularly limited, and for example, ion-exchanged water or distilled water may be used. If the dental adhesive composition contains water, the acid group of the (meth) acrylate having an acid group dissociates, and the solubility of the coating layer on the tooth surface, the dentin demineralization property and the permeability into dentin of the primer of the dental adhesive composition are improved, and the adhesiveness of the dental adhesive composition is improved.
The water content in the dental adhesive composition is not particularly limited, and is preferably 1% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 40% by mass or less, and still more preferably 10% by mass or more and 30% by mass or less, for example. If the water content in the dental adhesive composition is 1 mass% or more and 50 mass% or less, the solubility of the coating layer of the dental surface, the dentin demineralization property as a primer of the dental adhesive composition, and the permeability into dentin are improved.
Examples of the organic solvent include ethanol, acetone, 1-propanol, 2-propanol, and ethyl methyl ketone.
The content of the organic solvent in the adhesive composition for dental use is not particularly limited, and is, for example, preferably 5 to 60 mass%, more preferably 10 to 50 mass%, and still more preferably 20 to 40 mass%. If the content of the organic solvent in the dental adhesive composition is 5 mass% or more, the uniformity of the dental adhesive composition is improved, and if it is 60 mass% or less, the adhesiveness of the dental adhesive composition is improved.
In the dental adhesive composition of the present embodiment, as described above, the (meth) acrylate having an acid group and the linear siloxane represented by the general formula (1) are contained, whereby excellent adhesive force can be exhibited not only for dentin but also for ceramics.
Specifically, the adhesive composition for dental use according to the present embodiment can exhibit high adhesion to any of ceramics, enamel, and dentin (dentin). Therefore, according to the dental adhesive composition of the present embodiment, the adhesive force between the dental artifacts (for example, dental restorations) of the ceramic material and the dentin can be improved.
As described above, the (meth) acrylate having no acid group is contained in the adhesive composition for dental use according to the present embodiment, and thus the mechanical strength of the cured product of the adhesive composition for dental use can be improved, and the adhesion to ceramics and dentin can be further improved.
The application of the adhesive composition for dental use of the present embodiment is not particularly limited, and for example, the adhesive composition for dental use can be used for various dental materials.
Examples of the dental material include dental cements, dental adhesives, dental temporary sealing materials, dental primers, dental coating materials, dental composite resins, dental hard resins, dental cutting resin materials, dental temporary restorative materials, dental fillers, and dental powders. Among these, the dental adhesive composition of the present embodiment is suitably used for a dental adhesive, a dental composite resin, and a dental cement.
Examples
The present invention will be further described below using examples. The numerical values "parts" and "%" of the units are not shown below, and are mass references unless otherwise specified.
< Modulation of adhesive Material >
The adhesive materials (examples 1 to 12, comparative examples 1 to 3) having the compositions shown in Table 1 were prepared. The adhesive material is prepared by blending a methacrylate ester having an acid group, a silicone compound, a methacrylate ester having no acid group, a polymerization initiator, a polymerization inhibitor, a filler, an organic solvent, and water.
< Adhesion Strength to ceramic >)
The ceramic was polished with #600 water-resistant polishing paper, and the flat polished surface was coated with hydrofluoric acid, left to stand for 10 seconds, rinsed with distilled water, and subjected to ultrasonic cleaning for 10 minutes×2 times. The adhesive material thus prepared was applied thereto, and immediately dried by blowing.
Then, a plastic mold having a hole of Φ2.38mm was placed on the test surface, and light irradiation was performed for 10 seconds from above the mold by using a light irradiator (manufactured by GC corporation, G-LIGHTPRIMA IIPLUS), and the composite resin was filled, followed by light irradiation for 20 seconds. After immersing it in 37℃water for 24 hours, it was reciprocated 5000 times between 5℃and 55℃and the resultant was subjected to heat cycle treatment to obtain a test body.
The prepared test piece was subjected to a shear test at a crosshead speed of 1 mm/min using an automatic plotter (small bench test machine EZ-S, shimadzu corporation), and after that, an average value of shear adhesion strength was obtained to evaluate adhesion of the composite resin to ceramics when an adhesive material was used.
The adhesion of the composite resin to the ceramic (adhesion strength to the ceramic) when the adhesive material is used was evaluated as follows. Further, the evaluation was determined to be good when A, B was evaluated, and the evaluation was determined to be bad when C was evaluated.
[ Evaluation criteria ]
A when the average shear adhesion strength is 20MPa or more
B the average shear adhesion strength is 15MPa or more and less than 20MPa
When the average of the C shear bonding strength is less than 15MPa
Adhesive strength to enamel and adhesive strength to ivory
Dentin was ground with #400 water-resistant grinding paper to expose fresh face. The adhesive material was coated and immediately dried by air blowing.
A plastic mold having a hole of Φ2.38mm was placed on the test surface, and light irradiation was performed for 10 seconds from a light irradiator (manufactured by GC company, G-LIGHTPRIMA IIPLUS), and the composite resin was filled, followed by light irradiation for 20 seconds. Soaking in 37 deg.c water for 24 hr. The adhesive properties of the composite resin to dentin were evaluated by measuring the average shear adhesion strength of 5 specimens by using an automatic plotter (small bench test machine EZ-S manufactured by Shimadzu corporation) under a crosshead speed of 1 mm/min, and then obtaining an average value of the shear adhesion strength.
When the adhesive material is used, the evaluation criteria of the adhesiveness (adhesive strength to enamel and adhesive strength to dentin) of the composite resin to dentin (enamel, dentin) are as follows. Further, the evaluation was determined to be good when A, B was evaluated, and the evaluation was determined to be bad when C was evaluated.
[ Evaluation criteria ]
A when the average shear adhesion strength is 25MPa or more
B the average shear adhesion strength is 15MPa or more and less than 25MPa
When the average of the C shear bonding strength is less than 15MPa
Hereinafter, examples and comparative examples will be described.
Example 1
5 Parts of 4-methacryloyloxyethyl trimellitic anhydride (4-META) and 5 parts of 10-Methacryloyloxydecyl Dihydrogen Phosphate (MDP) as methacrylic acid esters having an acid group, 1.2 parts of linear siloxane (KP-410 manufactured by Xinyue chemical industry Co., ltd.) having (meth) acryloyl groups at both ends as silicone compounds, 15 parts of 2-hydroxy-1, 3-dimethylacryloxy propane (GDMA parts of methacrylic acid esters having no acid group and 5 parts of triethylene glycol dimethacrylate (TEGDMA), 2 parts of 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide (TPO) as a polymerization initiator, 1.0 part of Camphorquinone (CQ), 1 part of ethyl 4-dimethylaminobenzoate (EPA), 1 part of dibutylhydroxytoluene (2, 6-di-t-butyl-p-cresol) (BHT), 5 parts of hydrophobic fumed silica (produced by Japanese air 97 osil as a filler, air (registered trademark) and 33.8 parts of distilled water as an organic solvent. The results are shown in Table 1.
Example 2
The same procedure as in example 1 was repeated except that 6 parts of 4-META, 12 parts of MDP, 5.0 parts of KP-410, 12 parts of GDMA parts of CQ, 1.2 parts of acetone, 29.8 parts of distilled water and 20 parts of distilled water were used. The results are shown in Table 1.
Example 3
The same procedure as in example 1 was repeated except that 9 parts of 4-META, 7 parts of MDP, 9.9 parts of KP-410, 10 parts of GDMA, 1.8 parts of CQ, 30.3 parts of acetone and 18 parts of distilled water were used. The results are shown in Table 1.
Example 4
The same procedure as in example 1 was repeated except that 2.3 parts of a linear siloxane (KP-422, manufactured by Xinyue chemical industries Co., ltd.) containing a (meth) acryloyl group at one end was used in place of KP-410, and the amount of 4-META was 13 parts, the amount of MDP was 9 parts, the amount of CQ was 0.8 part, the amount of acetone was 24.9 parts, and the amount of distilled water was 21 parts. The results are shown in Table 1.
Example 5
The same procedure as in example 4 was repeated except that the amount of 4-META blended was 6 parts, the amount of MDP blended was 14 parts, the amount of KP-422 blended was 6.1 parts, the amount of GDMA blended was 12 parts, the amount of CQ blended was 1.9 parts, the amount of acetone blended was 31.0 parts, and the amount of distilled water blended was 15 parts. The results are shown in Table 1.
Example 6
The same procedure as in example 4 was repeated except that 11 parts of 4-META, 11 parts of MDP, 12.1 parts of KP-422, 10 parts of GDMA, 2.3 parts of CQ, 24.6 parts of acetone and 15 parts of distilled water were used. The results are shown in Table 1.
Example 7
The same procedure as in example 1 was repeated except that 0.5 part of a linear siloxane (KP-423, manufactured by Xinyue chemical industry Co., ltd.) containing (meth) acryloyl groups at both ends was blended in place of KP-410, and the blending amount of 4-META was 12 parts, the blending amount of MDP was 6 parts, the blending amount of CQ was 1.1 parts, the blending amount of acetone was 30.4 parts, and the blending amount of distilled water was 21 parts. The results are shown in Table 1.
Example 8
The same procedure as in example 7 was repeated except that the amount of 4-META was changed to 13 parts, the amount of MDP was changed to 7 parts, the amount of KP-423 was changed to 4.3 parts, the amount of GDMA was changed to 12 parts, the amount of CQ was changed to 1.0 part, and the amount of acetone was changed to 27.7 parts. The results are shown in Table 1.
Example 9
The same procedure as in example 7 was repeated except that 7 parts of 4-META, 12 parts of MDP, 14.8 parts of KP-423, 10 parts of GDMA, 1.4 parts of CQ, 25.8 parts of acetone and 15 parts of distilled water were used. The results are shown in Table 1.
Example 10
The same procedure as in example 1 was repeated except that 1.8 parts of a linear siloxane (DMS-U21, manufactured by Gelest Co., ltd.) containing (meth) acryloyl groups at both ends was blended in place of KP-410, and the blending amount of 4-META was 8 parts, the blending amount of MDP was 4 parts, the blending amount of CQ was 2.0 parts, the blending amount of acetone was 27.2 parts, and the blending amount of distilled water was 28 parts. The results are shown in Table 2.
Example 11
The same procedure as in example 10 was repeated except that the amount of 4-META was 5 parts, the amount of MDP was 10 parts, the amount of DMS-U21 was 3.9 parts, the amount of GDMA was 12 parts, the amount of CQ was 1.0 part, the amount of acetone was 35.1 parts, and the amount of distilled water was 19 parts. The results are shown in Table 2.
Example 12
The same procedure as in example 10 was repeated except that 10 parts of 4-META, 8 parts of MDP, 7.5 parts of DMS-U21, 10 parts of GDMA parts of CQ, 2.5 parts of acetone, 32.0 parts of distilled water and 16 parts of distilled water were used. The results are shown in Table 2.
Comparative example 1
The same procedure as in example 1 was repeated except that the silicone compound (0 parts) was not blended, and the blending amount of 4-META was 15 parts, the blending amount of MDP was 8 parts, the blending amount of CQ was 2.3 parts, the blending amount of acetone was 25.7 parts, and the blending amount of distilled water was 20 parts. The results are shown in Table 2.
Comparative example 2
The same procedure as in example 1 was repeated except that 3.6 parts of dimethylsilicone (a (meth) acryl-free siloxane) (KF-96L-2 cs, made by Xinyue chemical Co., ltd.) was used in place of KP-410, and the amount of 4-META was 8 parts, the amount of MDP was 6 parts, the amount of GDMA was 12 parts, the amount of CQ was 2.2 parts, the amount of acetone was 39.2 parts, and the amount of distilled water was 15 parts. The results are shown in Table 2.
Comparative example 3
The same procedure as in example 1 was repeated except that 11.4 parts of a silicone-containing acrylic polymer (KL-700, manufactured by Kyowa chemical Co., ltd.) was used in place of KP-410, and the amount of 4-META was 7 parts, the amount of MDP was 9 parts, the amount of GDMA was 10 parts, the amount of CQ was 1.6 parts, the amount of acetone was 24.0 parts, and the amount of distilled water was 23 parts. The results are shown in Table 2.
TABLE 1
TABLE 2
As is clear from Table 1, the adhesive containing the methacrylic acid ester having an acid group and the linear siloxane having a (meth) acryloyl group was excellent in the adhesive strength to ceramics, enamel and dentin (examples 1 to 12).
On the other hand, the adhesive containing no linear siloxane containing a (meth) acryloyl group was poor in adhesive strength to at least one of ceramics, enamel and dentin (comparative examples 1 to 3).
The embodiments disclosed above include, for example, the following modes.
(Additionally, 1)
A dental adhesive composition comprising: a (meth) acrylate having an acid group, and a linear siloxane represented by the following general formula (1).
(In the above-mentioned general formula (1),
X 1～X6 is independently an alkyl group having 1 to 6 carbon atoms or an ethylenically unsaturated group, m is an integer of 0 to 500,
When m is 2 or more, X 3、X4 may be the same or different in each repeating unit,
Y 1、Y2 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms which may have an ether bond,
Z 1～Z4 is each independently a hydrogen atom or an olefinically unsaturated group,
At least one of X 1～X6 and Z 1～Z4 is an ethylenically unsaturated group. )
(Additionally remembered 2)
The dental adhesive composition according to appendix 1, which comprises a (meth) acrylate having no acid group.
(Additionally, the recording 3)
The dental adhesive composition according to appendix 1 or 2, which contains a photopolymerization initiator.
(Additionally remembered 4)
The dental adhesive composition according to any one of supplementary notes 1 to 3, which comprises water.
While the embodiments of the present invention have been described above, the present invention is not limited to the specific embodiments, and various modifications and changes can be made within the scope of the invention described in the claims.
The present application claims priority based on japanese patent applications 2021-162363 of application No. 2021, 9 and 30 and japanese patent application 2022-141589 of application No. 2022, 9 and 6, the entire contents of which are hereinafter incorporated by reference.
Claims (4)
1. A dental adhesive composition comprising: (meth) acrylate having acid group, and
A linear siloxane represented by the following general formula (1),
In the general formula (1),
X 1～X6 is independently an alkyl group having 1 to 6 carbon atoms or an ethylenically unsaturated group,
M is an integer of 0to 500,
When m is 2 or more, X 3、X4 may be the same or different in each repeating unit,
Y 1、Y2 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms which may have an ether bond,
Z 1～Z4 is each independently a hydrogen atom or an olefinically unsaturated group,
At least one of X 1～X6 and Z 1～Z4 is an ethylenically unsaturated group.
2. The dental adhesive composition according to claim 1, comprising a (meth) acrylate having no acid group.
3. The dental adhesive composition according to claim 1 or 2, which contains a photopolymerization initiator.
4. The dental adhesive composition according to claim 1 or 2, which contains water.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021-162363 | 2021-09-30 | ||
| JP2022-141589 | 2022-09-06 | ||
| JP2022141589 | 2022-09-06 | ||
| PCT/JP2022/035780 WO2023054284A1 (en) | 2021-09-30 | 2022-09-26 | Dental adhesive composition |
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| Publication Number | Publication Date |
|---|---|
| CN118043020A true CN118043020A (en) | 2024-05-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280066283.2A Pending CN118043020A (en) | 2021-09-30 | 2022-09-26 | Dental adhesive composition |
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| CN (1) | CN118043020A (en) |
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- 2022-09-26 CN CN202280066283.2A patent/CN118043020A/en active Pending
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