CN113692269B - 牙科组合物 - Google Patents
牙科组合物 Download PDFInfo
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- CN113692269B CN113692269B CN202080028690.5A CN202080028690A CN113692269B CN 113692269 B CN113692269 B CN 113692269B CN 202080028690 A CN202080028690 A CN 202080028690A CN 113692269 B CN113692269 B CN 113692269B
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- alkyl
- substituted
- dental material
- unsubstituted
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- 239000000203 mixture Substances 0.000 title claims abstract description 40
- -1 polycyclic amide Chemical class 0.000 claims abstract description 168
- 239000000178 monomer Substances 0.000 claims abstract description 65
- 239000005548 dental material Substances 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 30
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 28
- 239000000945 filler Substances 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000012966 redox initiator Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000003368 amide group Chemical group 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000011350 dental composite resin Substances 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 239000010703 silicon Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 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 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000003479 dental cement Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- MKVYSRNJLWTVIK-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O MKVYSRNJLWTVIK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- NJWJLMYWQCXQOZ-UHFFFAOYSA-N [2-hydroxy-3-(4-propylphenoxy)propyl] 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 NJWJLMYWQCXQOZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000002245 particle Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000000463 material Substances 0.000 description 18
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000003638 chemical reducing agent Substances 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 239000002105 nanoparticle Substances 0.000 description 11
- 239000007800 oxidant agent Substances 0.000 description 11
- YIWFBNMYFYINAD-UHFFFAOYSA-N ethenylcyclopropane Chemical class C=CC1CC1 YIWFBNMYFYINAD-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 150000003141 primary amines Chemical group 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 150000003335 secondary amines Chemical group 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 125000002720 diazolyl group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000011877 solvent mixture Substances 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
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 125000002971 oxazolyl group Chemical group 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 102100035593 POU domain, class 2, transcription factor 1 Human genes 0.000 description 3
- 101710084414 POU domain, class 2, transcription factor 1 Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 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 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005594 diketone group Chemical group 0.000 description 3
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000001363 water suppression through gradient tailored excitation Methods 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 2
- UEKHZPDUBLCUHN-UHFFFAOYSA-N 2-[[3,5,5-trimethyl-6-[2-(2-methylprop-2-enoyloxy)ethoxycarbonylamino]hexyl]carbamoyloxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)NCCC(C)CC(C)(C)CNC(=O)OCCOC(=O)C(C)=C UEKHZPDUBLCUHN-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- 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 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 150000000996 L-ascorbic acids Chemical class 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
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- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/61—Cationic, anionic or redox initiators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
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Abstract
本文公开了一种牙科材料,其含有可聚合的水解稳定的多环酰胺单体。本公开涉及可聚合的水解稳定的多环酰胺单体的制造方法及其用于制备牙科可聚合的水解稳定的多环酰胺单体组合物的用途。本公开进一步涉及通过聚合牙科材料而获得的固化的牙科材料。
Description
发明领域
本公开涉及一种牙科材料,其含有可聚合的水解稳定的多环酰胺单体。本公开涉及所述可聚合的水解稳定的多环酰胺单体的制造方法及其用于制备牙科可聚合的水解稳定的多环酰胺单体组合物的用途。本公开进一步涉及通过聚合所述牙科材料而获得的固化的牙科材料。
发明背景
在牙科复合材料修复程序期间,由所述复合材料树脂聚合而发生聚合收缩应力。这种聚合应力向与牙科的界面的转移导致许多临床问题如牙釉质开裂、受损的结合性、术后敏感性和二次龋齿。
在本上下文中,现有技术已知的是环状的单体如单官能乙烯基环丙烷衍生物以比线性单体如(甲基)丙烯酸酯显著更低的聚合应力来反应。在聚合期间,单官能乙烯基环丙烷衍生物以开环机理来聚合。但是通常,单官能乙烯基环丙烷酯具有慢的聚合动力学。
美国专利号6136887公开了可聚合的乙烯基环丙烷衍生物,和美国专利号7365222公开了双环的环丙烷衍生物;其在聚合期间表现出低体积收缩率,并且同时可与(甲基)丙烯酸酯自由基共聚。
美国专利申请号2018/0036209公开了可自由基聚合的牙科材料,其含有至少一种乙烯基环丙烷,其在自由基聚合时仅轻微收缩,并且其具有高自由基聚合反应性,特别是在光聚合时。
美国专利申请号2008/0058443公开了具有低聚合收缩率和可比的力学性能的牙科材料,其包含至少一种可聚合的具有可聚合基团的杯[n]芳烃,其中所述可聚合基团是能够在自由基条件下聚合的基团如能够在自由基条件下通过开环聚合的(甲基)丙烯酸酯或(甲基)丙烯酰胺、环状基团,或是能够在阳离子条件下聚合的基团如脂环族环氧化物或氧杂环丁烷基团或多反应性硝酮基团。
美国专利号9580524公开了在均聚时表现出体积膨胀并且能够改进溶剂溶解性的乙烯基环丙烷,包含所述乙烯基环丙烷的单体组合物,乙烯基环丙烷的聚合物,包含所述聚合物的聚合物组合物,和通过固化所述单体组合物可获得的制品。所述乙烯基环丙烷可以合适地用于生产光学材料、模制材料、复合材料、铸造材料、密封材料、医用材料、牙科材料、记录材料、水门汀、涂层材料、粘合剂、用于全息光学记录介质的材料等。
Alupei等(Polymer 45(2004),2111-2117)已经表明3-乙氧基羰基-三环[3.2.1.02,4]辛-6-烯可以在自由基引发剂存在下转化成具有去甲三环烯(nortricyclene)重复主链单元的稳定聚合物。代替正常的乙烯基聚合,所述聚合机理是基于分子内的环丙烷化,伴随着开环过程,并且减少了聚合应力。
通过使用单官能乙烯基环丙烷酰胺,提高了聚合速率。
双(多环酰胺)化合物适于这种单官能乙烯基环丙烷结构。所述酰胺结构是水解稳定的并且具有足够的聚合动力学。
发明内容
一直需要开发散装填充修复物,其同时具有良好保持的结合、容易处置和期望的美学,例如通过将可聚合的水解稳定的多环酰胺单体作为牙科组合物中的添加剂来进行。
本公开的目标是提供一种可聚合的水解稳定的多环酰胺单体以及其作为添加剂用于牙科组合物的用途,以便与具有可比的双键含量的(甲基)丙烯酸酯相比显著降低聚合应力。含有可聚合的水解稳定的多环酰胺单体的组合物特别适合作为牙科材料,特别是作为牙科复合材料、牙科玻璃离聚物、牙科密封剂、牙科粘合剂、粘合促进剂、防粘材料、水门汀、牙冠形成材料或压印材料。
在本公开的第一方面,提供一种牙科材料,其包含:
(i)可聚合的水解稳定的多环酰胺单体,其包含式(I)的化合物:
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是亚烷基、O、S或CO;
n是整数0-1;
m是整数1-6;和
Z是(m+1)价未取代的或取代的C1-C18亚烷基,未取代的或取代的C3-C8环亚烷基,未取代的或取代的芳亚烷基,未取代的或取代的C5-C18亚芳基或未取代的或取代的C3-C18杂亚芳基;其中每个未取代的或取代的基团Z任选地包括下面的至少一种:1-6个氧、硅、硫原子或NR9,其中R9表示氢原子、直链或支化的或环状的C1-6烷基;
(ii)至少一种可聚合的树脂单体,其具有至少一个(甲基)丙烯酸酯基团、(甲基)丙烯酰胺基团、烯丙基或乙烯基;
(iii)任选的颗粒状填料;和
(iv)光引发剂和氧化还原引发剂中的至少一种。
本公开提供所述可聚合的水解稳定的多环酰胺单体用于制备牙科材料的用途。
在本公开的第二方面,提供一种制备包含式(I)的化合物的可聚合的水解稳定的多环酰胺单体的方法。该方法包括将包含以下各项的混合物进行反应:
(i)x当量的至少一种组分A,其具有式(II)的化合物:
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是亚烷基、O、S或CO;
n是整数0-1;和
T是羟基或卤素原子。
(ii)y当量的组分B,其具有式III化合物的伯胺官能团和仲胺官能团中的至少一种:
其中
R7是(r+1)价脂族C2-10基团、脂环族C3-C6基团或具有7-24个碳原子的芳亚烷基,其中每个基团R7任选地包含氧或硫原子,并且每个基团R7任选地经C1-4烷基取代;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基或(甲基)丙烯酰基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
L1和L2独立地是相同或不同的具有1-4个碳的直链或支链亚烷基;
X1是直接键或经R5取代的氮原子;
X2是氧原子;
p和q是整数0-4;和
r是整数1-6;
其中x和y是组分(i)和(ii)的摩尔当量。
以便形成包含下式(I)的化合物的可聚合的水解稳定的多环酰胺单体
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是亚烷基、O、S或CO;
n是整数0-1;
m是整数1-6;和
Z是(m+1)价未取代的或取代的C1-C18亚烷基、未取代的或取代的C3-C8环亚烷基、未取代的或取代的芳亚烷基、未取代的或取代的C5-C18亚芳基或未取代的或取代的C3-C18杂亚芳基;其中每个未取代的或取代的基团Z任选地包括下面的至少一种:1-6个氧、硅、硫原子或NR9,其中R9表示氢原子、直链或支化的或环状的C1-6烷基。
附图说明
图1描绘了在CDCl3中的双(降冰片烯环丙烷酰氨基)化合物1的1H NMR光谱。
图2描绘了关于CMX-树脂的双(降冰片烯环丙烷酰氨基)化合物1(HLU18-150-N5T5)的聚合收缩应力数据比较。
曲线1:t00182 Nov 6 2018 2 11pm张力计HLU18-150-N5T5_L 103118_QHL-2min_S1.tsd
0=束文件中的线数,
曲线2:t00183 Nov 6 2018 4 25pm张力计HLU18-150-N5T5_L 103118_QHL-2min_S2.tsd
0=束文件中的线数,
曲线3:t00008 Oct 1 2018 10 24am张力计CMX-树脂_K 900833_L 1802000718_后处理(PostRepair)_S1.tsd,
曲线4:t00009 Oct 1 2018 11 31am张力计CMX-树脂_K900833_L 1802000718_后处理(PostRepair)_S2.tsd,
曲线5:t00011 Oct 1 2018 2 50pm张力计CMX-树脂_K 900833_L 1802000718_后处理(PostRepair)_S3.tsd。
具体实施方式
下面结合各种实施方案,并且参考附图来描述本公开的上述方面以及其他方面、特征和优点。本公开中所用的一些术语定义如下:
除非另有规定,否则术语“烷基”指的是具有1-18个碳原子的单基团支化的或未支化的饱和烃链。这个术语可以通过基团如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、正己基、正癸基、十二烷基、十四烷基等来示例。烷基可以进一步用选自烯基、烷氧基和羟基的一种或多种取代基来取代。
除非另有规定,否则术语“亚烷基”指的是1-18个碳原子的线性饱和的二价烃基或3-18个碳原子的支化饱和的二价烃基,例如亚甲基、亚乙基、2,2-二甲基亚乙基、亚丙基、2-甲基亚丙基、亚丁基等,优选亚甲基、亚乙基或亚丙基。
术语“烷氧基”是含有键合到氧原子上的烷基的官能团。C1-4烷氧基可以包括具有1-4个碳原子的线性或支化的烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基。
术语“亚芳基”是“芳基”的二价结构部分。术语“芳基”指的是C5-C18元芳族、杂环、稠合芳族、稠合杂环、双芳族或双杂环的环体系。如本文所用,宽泛定义的“芳基”包括5元、6元、7元、8元、9元和10元单环芳族基团,其可以包括0-4个杂原子,例如苯、吡咯、呋喃、噻吩、咪唑、唑、噻唑、三唑、吡唑、吡啶、吡嗪、哒嗪、嘧啶等。在环结构中具有杂原子的那些“芳基”也可以称作“杂芳基”或“杂环”或“杂芳烃”。所述芳环可以在一个或多个环位置上用一个或多个包括但不限于以下的取代基取代:卤素,叠氮化物,烷基,芳烷基,烯基,炔基,环烷基,羟基,烷氧基,氨基(或季化氨基),硝基,巯基,亚氨基,酰氨基,膦酸酯,次膦酸酯,羰基,羧基,甲硅烷基,醚,烷基硫基,磺酰基,磺酰氨基,酮,醛,酯,杂环基,芳族或杂芳族结构部分,--CF3,--CN及其组合。
术语“芳基”还包括多环环体系,其具有两个或更多个环状环,在其中两个或更多个碳是两个相邻的环共用的(即,“稠环”),其中至少一个环是芳族的,例如另一环状环可以是环烷基、环烯基、环炔基、芳基和/或杂环基。杂环环的实例包括但不限于苯并咪唑基,苯并呋喃基,苯并硫代呋喃基,苯并硫苯基,苯并唑基,苯并/>唑啉基,苯并噻唑基,苯并三唑基,苯并四唑基,苯并异/>唑基,苯并异噻唑基,苯并咪唑啉基,咔唑基,4aH咔唑基,咔啉基,苯并二氢吡喃基,色烯基,噌啉基,十氢喹啉基,2H,6H-1,5,2-二噻嗪基,二氢芴基[2,3b]四氢呋喃,呋喃基,呋咱基,咪唑烷基,咪唑啉基,咪唑基,1H-吲唑基,吲哚烯基(indolenyl),二氢吲哚基,中氮茚基,吲哚基,3H-吲哚基,靛红酰基,异苯并呋喃基,异苯并二氢吡喃基,异吲唑基,异二氢吲哚基,异吲哚基,异喹啉基,异噻唑基,异/>唑基,亚甲基二氧苯基,吗啉基,萘啶基(naphthyridinyl),八氢异喹啉基,/>二唑基,1,2,3-/>二唑基,1,2,4-/>二唑基,1,2,5-/>二唑基,1,3,4-/>二唑基,/>唑烷基,/>唑基,羟吲哚基,嘧啶基,菲啶基,菲咯啉基,吩嗪基,吩噻嗪基,苯氧基噻吩基,吩嗪基,酞嗪基,哌嗪基,哌啶基,哌啶酮基,4-哌啶酮基,胡椒基,蝶啶基,嘌呤基,吡喃基,吡嗪基,吡唑烷基,吡唑啉基,吡唑基,哒嗪基,吡啶并/>唑,吡啶并咪唑,吡啶并噻唑,吡啶基(pyridinyl),吡啶基(pyridyl),嘧啶基,吡咯烷基,吡咯啉基,2H-吡咯基,吡咯基,喹唑啉基,喹啉基,4H-喹嗪基,喹喔啉基,喹宁环基,四氢呋喃基,四氢异喹啉基,四氢喹啉基,四唑基,6H-1,2,5-噻二嗪基,1,2,3-噻二唑基,1,2,4-噻二唑基,1,2,5-噻二唑基,1,3,4-噻二唑基,噻蒽基,噻唑基,噻吩基,噻吩并噻唑基,噻吩并/>唑基,噻吩并咪唑基,苯硫基和呫吨基。
术语“杂亚芳基”是“杂芳基”的二价结构部分。
术语“芳亚烷基”是“芳烷基”的二价结构部分。术语“芳烷基”指的是式-R’-芳基的基团,其中R’是如上所定义的亚烷基,例如亚甲基、亚乙基等。芳基部分是如上针对芳基所述任选取代的。
术语“环亚烷基”是“环烷基”的二价结构部分。术语“环烷基”指的是单环或多环的环烷基。单环环烷基的实例包括环丙基、环丁基、环戊基、环己基、环庚基和环辛基。多环环烷基的实例包括例如金刚烷基、降冰片基、十氢萘基、7,7-二甲基-双环[2.2.1]庚基、三环[5.2.1.02,6]癸基等。除非说明书另有明确规定,否则术语“环烷基”表示包括单环或多环的环烷基,其是经选自烷基、卤素、氧基或亚烷基链的一种或多种取代基任选取代的。
术语“环烷基亚烷基”指的是基团-R’-环烷基-”,其中R’是如上所定义的亚烷基如亚甲基、亚乙基等。如本文所用,C1-C8环烷基亚烷基指的是通过C1-C8亚烷基连接的环烷基。
术语“二价烃基”指的是具有2-18个碳原子的二价烃基,包括亚烷基如亚乙基,甲基亚甲基,亚丙基,亚丁基,亚戊基,亚己基和亚十八烷基;亚烷基如亚乙烯基、亚烯丙基和亚丁二烯基;环亚烷基如环亚丁基,环亚戊基和环亚己基;环亚烯基如环亚戊烯基和环亚己烯基;亚芳基如亚苯基和二甲苯撑(xenylene);芳亚烷基如亚苄基;和烷亚芳基如甲代亚苯基。
关于自由基聚合,术语“可聚合的结构部分”经常指的是任何能够加聚的双键如碳-碳双键。
术语“(甲基)丙烯酸酯”在本公开的上下文中意指丙烯酸酯以及相应的甲基丙烯酸酯。
术语“(甲基)丙烯酰基”在本公开的上下文中意指丙烯酰基以及相应的甲基丙烯酰基。
本公开涉及一种牙科材料,其含有可聚合的水解稳定的多环酰胺单体。本公开涉及制造所述可聚合的水解稳定的多环酰胺单体的方法。本公开涉及所述可聚合的水解稳定的多环酰胺单体用于制备牙科可聚合的水解稳定的多环酰胺单体组合物的用途。所述含有可聚合的水解稳定的多环酰胺单体的组合物特别适合作为牙科材料,特别是牙科复合材料、牙科玻璃离聚物、牙科密封剂、牙科粘合剂、粘合促进剂、防粘材料、水门汀、牙冠形成材料或压印材料。
在本公开的一方面,提供一种牙科材料,其包含:
(i)可聚合的水解稳定的多环酰胺单体,其包含式(I)的化合物:
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是亚烷基、O、S或CO;
n是整数0-1;
m是整数1-6;和
Z是(m+1)价未取代的或取代的C1-C18亚烷基、未取代的或取代的C3-C8环亚烷基、未取代的或取代的芳亚烷基、未取代的或取代的C5-C18亚芳基或未取代的或取代的C3-C18杂亚芳基;其中每个未取代的或取代的基团Z任选地包括下面的至少一种:1-6个氧、硅、硫原子或NR9,其中R9表示氢原子、直链或支化的或环状的C1-6烷基;
(ii)至少一种可聚合的树脂单体,其具有至少一个(甲基)丙烯酸酯基团、(甲基)丙烯酰胺基团、烯丙基或乙烯基;
(iii)任选的颗粒状填料;和
(iv)光引发剂和氧化还原引发剂中的至少一种。
I.可聚合的水解稳定的多环酰胺单体
可聚合的水解稳定的多环酰胺单体是式(I)的化合物
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是亚烷基、O、S或CO;
n是整数0-1;
m是整数1-6;和
Z是(m+1)价未取代的或取代的C1-C18亚烷基、未取代的或取代的C3-C8环亚烷基、未取代的或取代的芳亚烷基、未取代的或取代的C5-C18亚芳基或未取代的或取代的C3-C18杂亚芳基;其中每个未取代的或取代的基团Z任选地包括下面的至少一种:1-6个氧、硅、硫原子或NR9,其中R9表示氢原子、直链或支化的或环状的C1-6烷基。
术语“可聚合的水解稳定的多环酰胺单体”表示包含多于一个含有环丙基和酰胺基的环状结构部分。所述多环酰胺单体是水解稳定的。具体地,所述可聚合的多环酰胺单体在主链中不包含基团如酯,该基团在含水介质中在酸性条件下在约23-27℃的温度下在1个月内水解。酸性条件指的是pH为1-5,例如2-4或pH是3。
在某些实施方案中,所述可聚合的多环酰胺单体是具有式I的化合物含有环丙基的多环烯烃,其中R1,R2,R3,R4和R6是氢;X是亚烷基且n是1。
在一种具体实施方案中,所述可聚合的多环酰胺单体是降冰片烯类型的结构部分,其含有环丙基,具有式I的化合物,其中R1,R2,R3,R4和R6是氢;X是亚甲基且n是1。
在一种实施方案中,所述可聚合的多环酰胺是含取代的三环[3.2.1.02,4]辛-6-烯的单体。
在一种具体实施方案中,所述可聚合的多环酰胺单体是式I的化合物,其中m是1且R5是氢。
在式I化合物的某些实施方案中,Z是未取代的或取代的C1-C18亚烷基,其可以任选地包括下面的至少一种:1-6个氧、硅、硫原子或NR9,其中R9表示氢原子、直链或支化的或环状的C1-6烷基。
在一种实施方案中,Z表示根据式IV的基团:
其中
Ra和Rb独立地是相同或不同的氢原子,C1-6线性或支化的烷基或C4-10芳基;和
a是整数1-18。
在一种具体实施方案中,Z选自:
在某些实施方案中,Z表示根据式V的基团:
其中
Rc、Rd、Re和Rf独立地是相同或不同的氢原子,C1-6线性或支化的烷基或C4-10芳基;
X3和X4独立地是相同或不同的氧原子、硫原子和基团NR9,其中R9是氢原子或C1-4烷基;
L3是二价烃基,其选自线性或支化的C2-3亚烷基或C5-C18亚芳基。
b是整数1-10;
c是整数1-10;和
d是整数0-1。
在某些实施方案中,Z表示根据式VI的基团:
其中
R8表示直链、支化或环状的烷基。
L4和L5独立地是相同或不同的C2-20亚烷基;
e是整数1-10;和
f是整数0-1。
式I的化合物可以是选自下面的化合物:
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在本文公开的牙科材料的一种实施方案中,所述可聚合的水解稳定的多环酰胺单体的存在量可以是1-99%,基于牙科材料总重量。可替代地是2-95%;可替代地是5-90%或它们之间的任何值、范围或子范围,基于牙科材料的总重量。
在本公开的一方面,描述了制备可聚合的水解稳定的具有式I的化合物的多环酰胺单体的方法。
在一种实施方案中,式(I)的化合物通过使包含以下各项的混合物进行反应来获得:
(i)x当量的至少一种组分A,其具有式(II)的化合物:
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是亚烷基、O、S或CO;
n是整数0-1;和
T是羟基或卤素原子;
(ii)y当量的组分B,其具有式III化合物的伯胺官能团和仲胺官能团中的至少一种:
其中
R7是(r+1)价脂族C2-10基团、脂环族C3-C6基团或具有7-24个碳原子的芳亚烷基,其中每个基团R7任选地包含氧或硫原子,并且每个基团R7任选地经C1-4烷基取代;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基或(甲基)丙烯酰基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
L1和L2独立地是相同或不同的具有1-4个碳的直链或支链亚烷基;
X1是直接键或经R5取代的氮原子;
X2是氧原子;
p和q是整数0-4;和
r是整数1-6;
其中x和y是组分(i)和(ii)的摩尔当量。
在一种实施方案中,具有式(II)的化合物的组分A可以是降冰片烯环丙烷羧酸或降冰片烯环丙烷羰基卤化物。
所述卤化物可以选自溴或氯。
在一种具体实施方案中,具有式(II)的化合物的组分A可以是降冰片烯环丙烷羰基氯化物。
在本文公开的牙科材料的一种实施方案中,具有伯胺官能团和仲胺官能团中至少一种的组分B是式II的化合物:
其中
R7是(r+1)价脂族C2-10基团、脂环族C3-C6基团或具有7-24个碳原子的芳亚烷基,其中每个基团R7任选地包含氧或硫原子,并且每个基团R7任选地经C1-4烷基取代;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基或(甲基)丙烯酰基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
L1和L2独立地是相同或不同的具有1-4个碳的直链或支链亚烷基;
X1是直接键或经R5取代的氮原子;
X2是氧原子;
p和q是整数0-4;和
r是整数1-6;
措词“伯胺官能团和仲胺官能团中的至少一种”应当理解为表示“仅伯胺官能团”、“仅仲胺官能团”或“伯胺官能团和仲胺官能团二者”。
在式III的一种实施方案中,R7是(r+1)价脂族C2-10基团,脂环族C3-C6基团或具有7-24个碳原子的芳亚烷基。R7可以是二价(r=1),三价(r=2),四价(r=3),五价(r=5),六价(r=5)或七价(r=6)。
在本文公开的牙科材料的某些实施方案中,式III的化合物可以是式IIIa的二胺:
其中R5如上所定义;和
W是二价脂族C2-10基团,脂环族C3-C6基团或具有7-24个碳原子的芳亚烷基,其中每个基团任选地包含氧或硫原子,并且其任选地经C1-4烷基取代。
在本文公开的牙科材料的某些实施方案中,式III的化合物可以是式IIIb的化合物:
其中R5和X1如上所定义。
在本文公开的牙科材料的某些实施方案中,式III的化合物可以是式IIIc的单胺:
H2N-R5
式IIIc
其中R5是单价脂族C1-10基团,脂环族C3-C6基团或具有7-24个碳原子的芳亚烷基。
在本文公开的牙科材料的某些实施方案中,式III的化合物可以是式IIId的胺:
其中R5和R7如上所定义。
式III的化合物可以选自乙二胺,丙二胺,丁二胺,五亚甲基二胺,六亚甲基二胺,七亚甲基二胺,四亚甲基二胺,八亚甲基二胺,三甲基六亚甲基二胺,二亚乙基三胺,三亚乙基四胺,四亚乙基五胺,4,7,10-三氧杂-1,13-十三烷二胺,2,2'-(亚乙基氧)二乙胺,1,3-双-(氨基甲基)环己烷,1,3-双-(4-氨基苯氧基)苯,4,4'-亚甲基双-环己基胺,5-氨基-1,3,3-三甲基环己烷甲基胺,Jeffamine T403,Jeffamine T3000,Jeffamine T5000,氨基醇,丙醇胺,N,N’-二甲基乙二胺,N,N’-二苄基乙二胺,N,N’-二苄基5-氧杂壬烷二胺-1,9,N,N’-二苄基3,6-二氧杂辛烷二胺-1,8,N,N’-二乙基丙烷二胺,N,N’-二甲基丙二胺,正丁基胺,己基胺,环己基胺或苄胺。
在制备可聚合的水解稳定的具有式I的化合物的多环酰胺单体的方法的某些实施方案中,x当量的至少一种具有式(II)的化合物的组分A和y当量的组分B(具有式III的化合物的伯胺官能团和仲胺官能团中的至少一种)可以溶解在溶剂中并且在反应温度下搅拌。
在制备可聚合的水解稳定的具有式I的化合物的多环酰胺单体的方法的某些实施方案中,所述溶剂可以选自二氯甲烷、四氢呋喃、氯仿、二甲基亚砜和二甲基甲酰胺。反应温度可以例如是0℃-60℃,例如30℃-55℃。
在可聚合的水解稳定的具有式I的化合物的多环酰胺单体的制备中,可以使用碱。所述碱选自三乙胺、1,4-二氮杂双环[2.2.2]辛烷、二异丙基乙胺和二甲基氨基吡啶。
填料
本公开的牙科材料可以包括颗粒状填料。“颗粒状填料”是粉末状金属氧化物或氢氧化物、矿物硅酸盐或离子可沥滤的玻璃或陶瓷。颗粒状填料的实例可以选自通常用于牙科修复组合物的填料。
所述颗粒状填料可以具有单峰或多峰(例如双峰)粒度分布。所述颗粒状填料可以是无机材料。它也可以是交联的有机材料,其不溶于可聚合树脂中并且任选地用无机填料填充。所述颗粒状填料可以是辐射不透过的、辐射可透过的或非辐射不透过的。
合适的颗粒状无机填料的实例是天然存在的或合成的材料如石英,氮化物如氮化硅,得自例如Ce、Sb、Sn、Zr、Sr、Ba和Al的玻璃,胶体二氧化硅,长石,硼硅酸盐玻璃,高岭土,滑石,二氧化钛和锌玻璃,以及亚微米二氧化硅颗粒如热解法二氧化硅。
合适的填料颗粒的实例包括但不限于锶硅酸盐,锶硼硅酸盐,钡硅酸盐,钡硼硅酸盐,钡氟铝硼硅酸盐玻璃,钡铝硼硅酸盐,钙硅酸盐,钙铝钠氟磷硅酸盐,镧硅酸盐,铝硅酸盐,和包含前述填料中至少一种的组合物。所述填料颗粒可以进一步包含气相法二氧化硅。气相法二氧化硅的实例包括来自DeGussa AG的OX-50(平均粒度40nm),来自DeGussa AG的Aerosil R-972(平均粒度16nm),来自DeGussa AG的Aerosil 9200(平均粒度20nm),其他Aerosil气相法二氧化硅可以包括Aerosil 90,Aerosil 150,Aerosil 200,Aerosil 300,Aerosil 380,Aerosil R711,Aerosil R7200和Aerosil R8200,以及来自Cabot Corp.的Cab-O-Sil M5,Cab-O-Sil TS-720,Cab-O-Sil TS-610。合适的颗粒状有机填料颗粒的实例包括填充的或未填充的粉化聚碳酸酯或聚环氧化物。
用于本文公开的材料的填料颗粒可以在它们与有机化合物共混之前进行表面处理。使用硅烷偶联剂或其他化合物的表面处理是有益的,因为它们提升了颗粒状填料和基质的结合,并且使得填料颗粒能够更均匀地分散在有机树脂基质中,以及改进物理和力学性能。合适的硅烷偶联剂包括3-甲基丙烯酰氧基丙基三甲氧基硅烷,甲基丙烯酰氧基辛基三甲氧基硅烷,苯乙烯基乙基三甲氧基硅烷,3-巯基丙基三甲氧基硅烷,γ-巯基丙基三乙氧基硅烷,γ-氨基丙基三甲氧基硅烷及其混合物。
所述颗粒状填料通常的平均粒度是0.005-100μm,例如0.01-40μm,其使用例如通过电镜法或通过使用由MALVERN Mastersizer S或MALVERN Mastersizer 2000设备所体现的常规激光衍射颗粒尺寸化法测量。
本公开的牙科组合物可以包含纳米尺寸的颗粒。作为本公开中的纳米尺寸的颗粒,可以使用牙科组合物中所用的任何已知的纳米尺寸颗粒,而没有任何限制。纳米尺寸颗粒优选的实例包括无机氧化物如二氧化硅、氧化铝、二氧化钛、氧化锆的颗粒,任何这些氧化物的复合氧化物的颗粒,以及磷酸钙、羟基磷灰石、氟化钇和氟化镱的颗粒。优选地,所述纳米尺寸颗粒是二氧化硅、氧化铝、二氧化钛的颗粒,其通过火焰热解法制备。
所述纳米尺寸颗粒的平均粒度是1-50nm,例如3-40nm。所述纳米尺寸颗粒的平均粒度可以通过如下来测量:拍摄这些纳米尺寸颗粒的电镜照片,并且计算100个随机选择的纳米尺寸颗粒的直径的平均值。期望的是无机纳米尺寸颗粒事先经受利用表面处理剂的表面处理来改进无机填料和本公开的可聚合组合物之间的亲和性,和增加无机填料和可聚合组合物之间的化学键合以提升固化产物的力学强度。
在一种实施方案中,颗粒状填料可以是有机改性的二氧化硅纳米颗粒,其用乙氧基化双酚A二甲基丙烯酸酯(Ormosil II)稀释。
本公开的牙科材料可以包括10-90%w/w量的颗粒状填料,基于所述牙科材料的总重量。可替代地是30-85%或它们之间的任何值、范围或子范围,基于所述牙科材料的总重量。
光引发剂
本公开的牙科材料包括光引发剂和氧化还原引发剂中的至少一种。
措词“光引发剂和氧化还原引发剂中的至少一种”应当理解为表示“仅光引发剂”、“仅氧化还原引发剂”或“光引发剂和氧化还原引发剂二者”。
合适的光引发剂包括I型和II型。它们可以单独使用或作为不同的光引发剂加上另外的助引发剂的混合物来使用。一些优选的光敏剂可以包括单酮和二酮(例如α二酮),其吸收约300nm至约800nm(优选约400nm至约500nm)范围内的一些光,例如樟脑醌,偶苯酰,糠偶酰,3,3,6,6-四甲基环己二酮,菲醌和其他环状α二酮。在它们之中樟脑醌典型地是优选的。优选的给电子化合物包括取代的胺,例如4-(N,N-二甲基氨基)苯甲酸乙酯作为促进剂。
根据另外优选的实施方案,光引发剂进一步包含下式的碘化合物:
R10-I+-R11A-
其中
R10和R11是彼此独立地,表示有机结构部分,和
A-是阴离子;
例如二芳基碘盐可以选自(4-甲基苯基)[4-(2-甲基丙基)苯基]碘/>六氟锑酸盐,(4-甲基苯基)[4-(2-甲基丙基)苯基]碘/>四氟硼酸盐,二苯基碘/>(DPI)四氟硼酸盐,二(4-甲基苯基)碘/>(Me2-DPI)四氟硼酸盐,苯基-4-甲基苯基碘/>四氟硼酸盐,二-(4-叔丁基苯基)-碘/>六氟磷酸盐,双(4-叔丁基苯基)碘/>对甲苯磺酸盐,二(4-庚基苯基)碘/>四氟硼酸盐,二(3-硝基苯基)碘/>六氟磷酸盐,二(4-氯苯基)碘/>六氟磷酸盐,二(萘基)碘/>四氟硼酸盐,二(4-三氟甲基苯基)碘/>四氟硼酸盐,DPI六氟磷酸盐,Me2-DPI六氟磷酸盐;DPI六氟砷酸盐,二(4-苯氧基苯基)碘/>四氟硼酸盐,苯基-2-噻吩基碘/>六氟磷酸盐,3,5-二甲基吡唑基-4-苯基碘/>六氟磷酸盐,DPI六氟锑酸盐,2,2'-DPI四氟硼酸盐,二(2,4-二氯苯基)碘/>六氟磷酸盐,二(4-溴苯基)碘/>六氟磷酸盐,二(4-甲氧基苯基)碘/>六氟磷酸盐,二(3-羧基苯基)碘/>六氟磷酸盐,二(3-甲氧基羰基苯基)碘/>六氟磷酸盐,二(3-甲氧基磺酰基苯基)碘/>六氟磷酸盐,二(4-乙酰氨基苯基)碘/>六氟磷酸盐,二(2-苯并噻吩基)碘/>六氟磷酸盐和DPI六氟磷酸盐。/>
具体地,碘化合物包括二苯基碘/>(DPI)六氟磷酸盐,二(4-甲基苯基)碘/>(Me2-DPI)六氟磷酸盐,二-(4-叔丁基苯基)-碘/>六氟磷酸盐,二芳基碘/>六氟锑酸盐,(4-甲基苯基)[4-(2-甲基丙基)苯基]碘/>六氟锑酸盐,(4-甲基苯基)[4-(2-甲基丙基)苯基]碘/>六氟磷酸盐(/>250,k可获自BASF SE的商业产品),(4-甲基苯基)[4-(2-甲基丙基)苯基]碘/>四氟硼酸盐,4-辛氧基苯基苯基碘/>六氟锑酸盐,4-(2-羟基十四烷氧基苯基)苯基碘/>六氟锑酸盐,和4-异丙基-4'-甲基二苯基碘/>硼酸盐。
根据一种具体的实施方案,碘化合物是二(4-甲基苯基)碘/>(Me2-DPI)六氟磷酸盐。
用于聚合可自由基光聚合的组合物的其他合适的光引发剂可以包括氧化膦类,其典型地的官能波长是约380nm至约1200nm。官能波长范围为约380nm至约450nm的优选的氧化膦自由基引发剂是酰基和双酰基氧化膦。
当在大于约380nm至约450nm的波长范围下照射时,能够自由基引发的可商购氧化膦光引发剂可以包括1-羟基环己基苯基酮(IRGACURE 184),2,2-二甲氧基-1,2-二苯基乙-1-酮(IRGACURE 651),双(2,4,6-三甲基苯甲酰基)苯基氧化膦(IRGACURE 819),1-[4-(2-羟基乙氧基)苯基]-2-羟基-2-甲基-1-丙烷-1-酮(IRGACURE 2959),2-苄基-2-二甲基氨基-1-(4-吗啉基苯基)丁酮(IRGACURE 369),2-甲基-1-[4-(甲基硫基)苯基]-2-吗啉基丙-1-酮(IRGACURE 907),2-羟基-2-甲基-1-苯基丙-1-酮(DAROCUR 1173),双(2,4,6-三甲基苯甲酰基)苯基氧化膦(IRGACURE 819),双(2,6-二甲氧基苯甲酰基)-(2,4,4-三甲基戊基)氧化膦(CGI 403),双(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦和2-羟基-2-甲基-1-苯基丙-1-酮的25:75重量比的混合物(IRGACURE 1700),双(2,4,6-三甲基苯甲酰基)苯基氧化膦和2-羟基-2-甲基-1-苯基丙-1-酮的1:1重量比混合物(DAROCUR 4265),和2,4,6-三甲基苄基苯基次膦酸乙酯(LUCIRIN LR 8893X)。
合适的氧化还原引发剂包含还原剂和氧化剂,其典型地彼此反应或不然彼此协同以产生能够在独立于光的存在的暗反应中引发可聚合双键聚合的自由基。选择还原剂和氧化剂,以使得聚合引发剂体系是足够储存稳定的,并且没有不期望的变色以允许在典型的牙科条件下储存和使用。此外,选择还原剂和氧化剂,以使得聚合引发剂体系与树脂体系足够可混溶,以允许聚合引发剂体系在组合物中溶解。
有用的还原剂包括抗坏血酸,抗坏血酸衍生物,和金属络合的抗坏血酸化合物,如美国专利号5501727中所述;胺,即叔胺如4-叔丁基二甲基苯胺。其他次级还原剂可以包括氯化钴(II),氯化亚铁,硫酸铁,肼,羟胺,连二亚硫酸盐或亚硫酸盐阴离子的盐,及其混合物。
合适的氧化剂包括过硫酸及其盐,例如铵、钠、钾、铯和烷基铵盐。另外的氧化剂包括过氧化物如过氧化苯甲酰,氢过氧化物如氢过氧化异丙苯,叔丁基氢过氧化物,过氧化(2-乙基己基)碳酸叔丁酯,叔丁基氢过氧化物,二(叔丁基)过氧化物,过氧化-3,5,5-三甲基-己酸叔丁酯,戊基氢过氧化物和过氧化二硫酸钾,以及过渡金属的盐如氯化钴(III)和氯化铁,硫酸铈(IV),过硼酸及其盐,高锰酸及其盐,过磷酸及其盐,及其混合物。一种或多种不同的氧化剂或一种或多种不同的还原剂可以用于聚合引发剂体系。
也可以加入少量的过渡金属化合物来加速氧化还原固化速率。过渡金属化合物可以是V、Fe、Cu、Ti、Mn、Ni和Zn的盐。最优选地,Fe或Cu的过渡金属盐。四价和/或五价钒化合物是优选的,包括氧化钒(IV),乙酰丙酮酸氧钒(IV),草酸氧钒(IV),硫酸氧钒(IV),氧双(1-苯基-1,3-丁二酸根合)钒(IV),双(麦芽酸根合)氧钒(IV),氧化钒(V),偏钒酸钠(V)和偏钒酸铵(V)。铜化合物的实例包括乙酰丙酮酸铜,乙酸铜(II),油酸铜,氯化铜(II)和溴化铜(II)。
氧化还原引发剂体系可以任选地包括聚合促进剂。
聚合促进剂选自芳族磺酸盐,亚硫酸盐,亚硫酸氢盐和硫脲化合物。
可以用作聚合促进剂的芳族磺酸盐的实例包括但不限于对甲苯磺酸盐如对甲苯亚磺酸钠,对甲苯亚磺酸钾,对甲苯亚磺酸钙;苯亚磺酸盐如苯亚磺酸钠,苯亚磺酸钾,苯亚磺酸钙,2,4,6-三乙基苯亚磺酸,2,4,6-三乙基苯亚磺酸钠,2,4,6-三乙基苯亚磺酸钾,2,4,6-三乙基苯亚磺酸钙,2,4,6-三异丙基苯亚磺酸,2,4,6-三异丙基苯亚磺酸钠,2,4,6-三异丙基苯亚磺酸钾和2,4,6-三异丙基苯亚磺酸钙。
可以用作聚合促进剂的亚硫酸盐的实例包括但不限于亚硫酸钠,亚硫酸钾,亚硫酸钙,亚硫酸铵,亚硫酸氢钠和亚硫酸氢钾。
可以用作聚合促进剂的硫脲的实例包括但不限于1-乙基-2-硫脲,1-(2-吡啶基)-2-硫脲,硫脲,乙基硫脲,甲基硫脲,N,N'-二甲基硫脲,N,N'-二乙基硫脲,N,N'-二正丙基硫脲,N,N'-二环己基硫脲,三甲基硫脲,三乙基硫脲,三正丙基硫脲,三环己基硫脲,四甲基硫脲,四乙基硫脲,四正丙基硫脲,四环己基硫脲,3,3-二甲基亚乙基硫脲,4,4-二甲基-2-咪唑啉硫酮,1,1-二丁基硫脲,1,3-二丁基硫脲;及其混合物。
还原剂和氧化剂的存在量足以允许充足的自由基反应速率。
还原剂或氧化剂可以微胶囊化来提升组合物的贮藏稳定性,和如果需要的话允许将还原剂和氧化剂包装在一起(美国专利号5154762)。恰当选择包封剂可允许将氧化剂和还原剂和甚至酸性官能组分和任选的填料以储存稳定态相组合。此外,恰当选择水不溶性包封剂允许将还原剂和氧化剂与颗粒状反应性玻璃和水以储存稳定态相组合。
双固化引发剂体系将光引发剂体系和氧化还原引发剂体系相组合。
在牙科材料的一种实施方案中,光引发剂和氧化还原引发剂中至少一种的存在量可以是牙科材料的0.1重量%至约5重量%。
均聚/共聚
根据本公开的可聚合的水解稳定的多环酰胺单体可以单独聚合或与可自由基聚合单体混合来聚合。
可聚合单体
在牙科材料的一种实施方案中,可聚合单体的存在量可以是该牙科材料的1重量%至约99重量%。
可聚合单体可以是丙烯酸酯,甲基丙烯酸酯,烯属不饱和化合物,含羧基的不饱和单体,(甲基)丙烯酸的C2-8羟烷基酯,(甲基)丙烯酸的C1-24烷基酯或环烷基酯,(甲基)丙烯酸的C2-18烷氧基烷基酯,烯烃或二烯化合物,单酯/二酯,单醚,加合物,乙烯基单体,苯乙烯基单体,TPH树脂,SDR树脂,PBA树脂和/或不含BPA的树脂。
具体的丙烯酸酯单体的实例包括但不限于丙烯酸甲基酯,丙烯酸乙基酯,丙烯酸丙基酯,丙烯酸异丙基酯,丙烯酸2-羟乙基酯,丙烯酸羟丙基酯,丙烯酸四氢糠基酯,丙烯酸缩水甘油基酯,甘油单丙烯酸酯和二丙烯酸酯,乙二醇二丙烯酸酯,聚乙二醇二丙烯酸酯,新戊二醇二丙烯酸酯,三羟甲基丙烷三丙烯酸酯,单丙烯酸酯,二丙烯酸酯,三丙烯酸酯,季戊四醇和二季戊四醇的单丙烯酸酯、二丙烯酸酯、三丙烯酸酯和四丙烯酸酯,1,3-丁二醇二丙烯酸酯,1,4-丁二醇二丙烯酸酯,1,6-己二醇二丙烯酸酯,2,2’-双[3(4-苯氧基)-2-羟基丙烷-1-丙烯酸酯]丙烷,2,2'-双(4-丙烯酰氧苯基)丙烷,2,2'-双[4(2-羟基-3-丙烯酰氧-苯基)]丙烷,2,2'-双(4-丙烯酰氧乙氧基苯基)丙烷,2,2'-双(4-丙烯酰氧丙氧基苯基)丙烷,2,2'-双(4-丙烯酰氧二乙氧基苯基)丙烷,2'-双[3(4-苯氧基)-2-羟基丙烷-1-丙烯酸酯]丙烷和二季戊四醇五丙烯酸酯酯。
具体的常规甲基丙烯酸酯单体的实例包括但不限于甲基丙烯酸甲基酯,甲基丙烯酸乙基酯,甲基丙烯酸丙基酯,甲基丙烯酸异丙基酯,甲基丙烯酸四氢糠基酯,甲基丙烯酸缩水甘油基酯,双酚A的甲基丙烯酸二缩水甘油基酯(2,2-双[4-(2-羟基-3-甲基丙烯酰氧丙氧基)苯基]丙烷)(BisGMA),4,4,6,16(或4,6,6,16)-四甲基-10,15-二氧-11,14-二氧杂-2,9-二氮杂十七-16-烯酸2-[(2-甲基-1-氧-2-丙烯-1-基)氧]乙基酯(CAS号72869-86-4)(UDMA),甘油单甲基丙烯酸酯和二甲基丙烯酸酯,乙二醇二甲基丙烯酸酯,聚乙二醇二甲基丙烯酸酯,三甘醇二甲基丙烯酸酯(TEGDMA),新戊二醇二甲基丙烯酸酯,三羟甲基丙烷三甲基丙烯酸酯,季戊四醇和二季戊四醇的单甲基丙烯酸酯、二甲基丙烯酸酯、三甲基丙烯酸酯和四甲基丙烯酸酯,1,3-丁二醇二甲基丙烯酸酯,1,4-丁二醇二甲基丙烯酸酯,双[2-(甲基丙烯酰氧)乙基]磷酸酯(BisMEP),1,6-己二醇二甲基丙烯酸酯,2-2'-双(4-甲基丙烯酰氧苯基)丙烷,2,2'-双[4(2-羟基-3-甲基丙烯酰氧-苯基)]丙烷,2,2'-双(4-甲基丙烯酰氧乙氧基苯基)丙烷,2,2'-双(4-甲基丙烯酰氧丙氧基苯基)丙烷,2,2'-双(4-甲基丙烯酰氧二乙氧基苯基)丙烷,2,2'-双[3(4-苯氧基)-2-羟基丙烷-1-甲基丙烯酸酯]丙烷,二-2-甲基丙烯酰氧乙基六亚甲基二氨基甲酸酯,二-2-甲基丙烯酰氧乙基三甲基六亚乙基二氨基甲酸酯,二-2-甲基丙烯酰氧乙基二甲基苯二氨基甲酸酯,亚甲基-双-2-甲基丙烯酰氧乙基-4-环己基氨基甲酸酯,二-2-甲基丙烯酰氧乙基-二甲基环己烷二氨基甲酸酯,亚甲基-双-2-甲基丙烯酰氧乙基-4-环己基氨基甲酸酯,二-1-甲基-2-甲基丙烯酰氧乙基-三甲基-六亚甲基二氨基甲酸酯,二-1-甲基-2-甲基丙烯酰氧乙基-二甲基苯二氨基甲酸酯,二-1-甲基-2-甲基丙烯酰氧乙基-二甲基环己烷二氨基甲酸酯,亚甲基-双-1-甲基-2-甲基丙烯酰氧乙基-4-环己基氨基甲酸酯,二-1-氯甲基-2-甲基丙烯酰氧乙基-六亚甲基二氨基甲酸酯,二-1-氯甲基-2-甲基丙烯酰氧乙基-三甲基六亚甲基二氨基甲酸酯,二-1-氯甲基-2-甲基丙烯酰氧乙基-二甲基苯二氨基甲酸酯,二-1-氯甲基-2-甲基丙烯酰氧乙基-二甲基环己烷二氨基甲酸酯,亚甲基-双-2-甲基丙烯酰氧乙基-4-环己基氨基甲酸酯,二-1-甲基-2-甲基丙烯酰氧乙基-六亚甲基二氨基甲酸酯,二-1-甲基-2-甲基丙烯酰氧乙基-三甲基六亚甲基二氨基甲酸酯,二-1-甲基-2-甲基丙烯酰氧乙基-二甲基苯二氨基甲酸酯,二-1-甲基-2-甲基丙烯酰氧乙基-二甲基环己烷二氨基甲酸酯,亚甲基-双-1-甲基-2-甲基丙烯酰氧乙基-4-环己基氨基甲酸酯,二-1-氯甲基-2-甲基丙烯酰氧乙基-六亚甲基二氨基甲酸酯,二-1-氯甲基-2-甲基丙烯酰氧乙基-三甲基六亚甲基二氨基甲酸酯,二-1-氯甲基-2-甲基丙烯酰氧乙基-二甲基苯二氨基甲酸酯,二-1-氯甲基-2-甲基丙烯酰氧乙基-二甲基环己烷二氨基甲酸酯,和亚甲基-双-1-氯甲基-2-甲基丙烯酰氧乙基-4-环己基氨基甲酸酯。
烯属不饱和化合物的实例包括但不限于丙烯酸酯,甲基丙烯酸酯,羟基官能的丙烯酸酯,羟基官能的甲基丙烯酸酯,含卤素和羟基的甲基丙烯酸酯及其组合。这样的可自由基聚合的化合物包括甲基丙烯酸正丁基酯、仲丁基酯或叔丁基酯,甲基丙烯酸己基酯,甲基丙烯酸2-乙基己基酯,甲基丙烯酸辛基酯,甲基丙烯酸癸基酯,甲基丙烯酸月桂基酯,甲基丙烯酸环己基酯,(甲基)丙烯酸硬脂酯,(甲基)丙烯酸烯丙基酯,三(甲基)丙烯酸甘油酯,二甘醇二(甲基)丙烯酸酯,三甘醇二(甲基)丙烯酸酯,1,3-丙二醇二(甲基)丙烯酸酯,1,2,4-丁三醇三(甲基)丙烯酸酯,1,4-环己烷二醇二(甲基)丙烯酸酯,季戊四醇四(甲基)丙烯酸酯,山梨糖醇六(甲基)丙烯酸酯,双[1-(2-丙烯酰氧)]-对乙氧基苯基二甲基甲烷,双[1-(3-丙烯酰氧-2-羟基)]-对丙氧基苯基二甲基甲烷,乙氧基化的双酚A二(甲基)丙烯酸酯,和三羟乙基-异氰尿酸酯三(甲基)丙烯酸酯;氨基甲酸酯(甲基)丙烯酸酯;((二)氨基甲酸酯二甲基丙烯酸酯),聚乙二醇的双(甲基)丙烯酸酯,和含氯基团、溴基团、氟基团和羟基基团的单体如3-氯-2-羟丙基(甲基)丙烯酸酯;2,2-双[4-(2-羟基-3-甲基丙烯酰氧丙氧基)苯基]丙烷和六亚甲基二异氰酸酯(HMDI)的反应产物。
含羧基的不饱和单体的实例包括但不限于例如丙烯酸,甲基丙烯酸,巴豆酸,衣康酸,马来酸和富马酸。
(甲基)丙烯酸的C2-8羟烷基酯的实例包括但不限于(甲基)丙烯酸2-羟乙基酯,(甲基)丙烯酸2-羟丙基酯,(甲基)丙烯酸3-羟丙基酯和(甲基)丙烯酸羟丁基酯。
(甲基)丙烯酸的C2-18烷氧基烷基酯的实例包括但不限于甲基丙烯酸甲氧基丁基酯,甲基丙烯酸甲氧基乙基酯,甲基丙烯酸乙氧基乙基酯和甲基丙烯酸乙氧基丁基酯。
烯烃或二烯化合物包括但不限于乙烯,丙烯,丁烯,异丁烯,异戊二烯,氯丙烯,含氟烯烃和氯乙烯。
单酯的实例可以包括聚醚多元醇(例如聚乙二醇、聚丙二醇或聚丁二醇)和不饱和羧酸(优选甲基丙烯酸)之间的单酯,含酸酐基团的不饱和化合物(例如马来酸酐或衣康酸酐)和二醇(例如乙二醇,1,6-己二醇或新戊二醇)之间的单酯或二酯。
单醚的实例可以包括聚醚多元醇(例如聚乙二醇、聚丙二醇或聚丁二醇)和含羟基的不饱和单体(例如甲基丙烯酸2-羟基酯)之间的单醚。
加合物的实例可以包括但不限于不饱和羧酸和单环氧化合物之间的加合物;(甲基)丙烯酸缩水甘油基酯(优选甲基丙烯酸缩水甘油基酯),一元酸(例如乙酸、丙酸、对叔丁基苯甲酸或脂肪酸)之间的加合物。
乙烯基单体的实例包括但不限于氨丙基乙烯基醚,氨乙基乙烯基醚,N-乙烯基甲酰胺,碳酸亚乙烯基酯,乙酸乙烯酯,二乙烯基苯,琥珀酸二乙烯基酯,己二酸二乙烯基酯,邻苯二甲酸二乙烯基酯,乙烯基吡啶,N-乙烯基吡咯烷酮,乙烯基咔唑,亚乙烯基卤化物,和(甲基)丙烯酸乙烯基酯。
苯乙烯基单体的实例包括但不限于苯乙烯和2-甲基苯乙烯。
(甲基)丙烯酰胺可以选自下面的化合物:
(甲基)丙烯酰胺,亚甲基双-(甲基)丙烯酰胺,二丙酮(甲基)丙烯酰胺,
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另外的组分
根据本公开的牙科组合物可以包含另外的组分,例如紫外线稳定剂,一种或多种阻聚剂,一种或多种溶剂,着色剂,荧光剂,遮光剂,颜料,粘度改变剂,氟化物释放剂及其组合。
紫外线稳定剂的实例可以包括2-(2'-羟基-5'-甲基苯基)-2H-苯并三唑,2-(2'-羟基-5'-叔辛基苯基)-2H-苯并三唑,2-羟基-4-甲氧基二苯甲酮(UV-9),2-(2'-羟基-4',6'-二叔戊基苯基)-2H-苯并三唑,2-羟基-4-正辛氧基二苯甲酮,2-(2'-羟基-5'-甲基丙烯酰氧乙基苯基)-2H-苯并三唑,吩噻嗪和HALS(受阻胺光稳定剂)。
用于自由基体系的典型的阻聚剂可以包括对苯二酚单甲醚(MEHQ),丁基化羟基甲苯(BHT),叔丁基对苯二酚(TBHQ),对苯二酚,苯酚,3,5-二叔丁基-4-羟基苯甲醚(2,6-二叔丁基-4-乙氧基酚),2,6-二叔丁基-4-(二甲基氨基)甲基苯酚或2,5-二叔丁基对苯二酚,丁基羟基苯胺等。所述阻聚剂充当自由基清除剂来捕获组合物中的自由基和延长牙科材料的贮藏寿命稳定性。所述阻聚剂如果存在的话,则存在量可以是牙科材料的约0.001重量%至约1.5重量%,例如牙科材料的约0.005重量%至约1.1重量%或约0.01重量%至约0.08重量%。所述牙科材料可以包括一种或多种阻聚剂。
本公开的牙科材料包含含有水和有机溶剂的溶剂混合物。所述溶剂混合物可以包含一种或多种有机溶剂。
如本文所用,术语“有机溶剂”表示任何这样的有机化合物,其在室温是流体或液体,并且其能够溶解或至少部分地溶解本公开的牙科组合物的组分。所述有机溶剂根据它的挥发性和生理学无害性来合适选择。优选地,所述有机溶剂与水相比是更挥发性的,也就是说,它在20℃的蒸气压高于水。此外,优选的是所述有机溶剂对于要治疗的患者来说,特别是对于人类患者来说是无毒的。
优选地,所述溶剂混合物的有机溶剂选自正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、丙酮和甲乙酮。优选地,所述牙科材料包含25-50重量%,更优选27-47重量%,最优选29-44重量%量的溶剂混合物,基于所述牙科材料的总重量。
优选的是溶剂混合物中包含的有机溶剂是正丙醇或异丙醇,优选异丙醇。
可聚合的水解稳定的多环酰胺单体作为牙科材料的用途
牙科组合物通过将本公开牙科组合物的组分混合来制备。所述牙科组合物的组分可以以各种方式和量组合(例如混合或共混),以便形成本公开的牙科组合物。
可固化的牙科材料组合物可以包含:
a)1-99%w/w的可聚合的水解稳定的多环酰胺单体;
b)0.01-5%w/w的用于自由基聚合的光引发剂;和
c)1-99%的可聚合的单体。
本公开的牙科材料可以是复合材料,并且可以包括约30至约90重量%量的填料。
本公开的牙科材料可以是粘合剂,并且可以包括约50至约65重量%量的填料,以及0-70重量%的溶剂。
根据本公开的牙科材料可以是水门汀,并且可以包括约50至约90重量%量的填料。
所述牙科复合材料可以通过混合所述可聚合的水解稳定的多环酰胺单体基质和填料来配制。
现在将通过下面的实施例来进一步说明本公开。
实施例:
合成水解稳定的双(降冰片烯环丙烷酰氨基)化合物
将5.9g(35mmol)的降冰片烯环丙烷羰基氯化物溶解在75mL二氯甲烷中,并且置于冰浴中。将2.7g(17mmol)的二胺异构体混合物、TMHDA(CAS 25620-58-0)和3.44g(34mmol)三甲基胺溶解在20mL二氯甲烷中,并且逐滴加入至反应混合物中。反应在室温进行30min,并且通过加入150mL水来淬灭。将水层分离,并且用50mL二氯甲烷洗涤3次。将全部有机层合并,干燥和在减压下除去溶剂。双(降冰片烯环丙烷酰氨基)化合物(1)是无色固体。产物通过1H NMR光谱表征,如图1所示。
应用实施例1
收缩应力:
收缩应力用称作张力计的收缩应力测量装置来测量,该装置是由美国牙科学会基金会(ADAF)的Paffenbarger研究中心设计和制作的。这个装置是基于悬臂梁理论,即在聚合期间通过收缩样品所产生的弯曲力引起悬臂梁挠曲。将牙科树脂或复合材料注入6.0mm直径和2.25mm厚度的两个玻璃棒之间的小室中。将材料用QHL-75卤灯以400mW/cm2的光强度固化60秒。张力计的更详细描述、实验程序和表征在(H.Lu等,Journal of MaterialsScience,Materials in Medicine,2004,第15卷,1097-1103)中进行了讨论,其以其全部通过引用并入本文。
双(降冰片烯环丙烷酰氨基)化合物(1)与三甘醇二甲基丙烯酸酯(TEGDMA)的共聚
为了测定聚合收缩率、应力,将表1中所示成分的混合物进行混合,然后用可见光源进行照射。
HLU18-150-N5T5的成分的最大收缩应力是1.5MPa(如图2所示)。
对比例
评价了CMX-树脂的收缩应力,观察到最大收缩应力是4.5MPa(如图2所示);CMX-树脂还表现出明显更高的收缩应力形成速率。
虽然已经参考一种或多种实施方案来描述了本公开,但是本领域技术人员将理解可以进行各种改变,和对其要素进行等价取代,而不脱离本公开的范围。另外,可以进行许多改动来将具体的情形或材料用于本公开的教导,而不脱离其基本范围。所以,意图是本公开不限于作为进行本公开的预期的最佳模式而公开的具体实施方案,而是本公开将包括落入附加的权利要求范围中的所有实施方案。另外,详细描述中确定的所有数值应当解释为如同明确地确定了精确值和近似值二者。
Claims (13)
1.一种牙科材料,包含:
(i)可聚合的水解稳定的多环酰胺单体,其包含式(I)的化合物:
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是-CH2;
m是整数1-6;和
Z是m价未取代的或取代的C1-C18亚烷基、未取代的或取代的C3-C8环亚烷基、未取代的或取代的芳亚烷基、未取代的或取代的C5-C18亚芳基或未取代的或取代的C3-C18杂亚芳基;其中每个未取代的或取代的基团Z任选地包括下面的至少一种:1-6个氧、硅、硫原子或NR9,其中R9表示氢原子、直链或支化或环状的C1-6烷基;
(ii)至少一种可聚合的树脂单体,其具有至少一个(甲基)丙烯酸酯基团、(甲基)丙烯酰胺基团、烯丙基或乙烯基;
(iii)任选的颗粒状填料;和
(iv)光引发剂和氧化还原引发剂中的至少一种。
2.根据权利要求1所述的牙科材料,其中R1、R2、R3、R4和R6是氢。
3.根据权利要求1所述的牙科材料,其中R1、R2、R3、R4、R5和R6是氢。
4.根据权利要求1所述的牙科材料,其中Z表示式IV、V或VI的基团;
其中
Ra、Rb、Rc、Rd、Re和Rf独立地是相同或不同的氢原子、C1-6线性或支化的烷基或C4-10芳基;
R8表示直链、支化的或环状的烷基;
X3和X4独立地是相同或不同的氧原子、硫原子或基团NR9,其中R9是氢原子或C1-4烷基;
L3是二价烃基,其选自线性或支化的C2-3亚烷基或C5-C18亚芳基;
L4和L5独立地是相同或不同的C2-20亚烷基;
a是整数1-18;
b是整数1-10;
c是整数1-10;
d是整数0-1,
e是整数1-10;和
f是整数0-1。
5.根据权利要求1所述的牙科材料,其中式(I)的化合物通过使包含以下各项的混合物反应来获得:
(i)x当量的至少一种组分A,其具有式(II)的化合物:
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是-CH2;和
T是羟基或卤素原子;
(ii)y当量的组分B,其具有式III化合物的伯胺官能团和仲胺官能团中的至少一种:
其中
R7是(r+1)价脂族C2-10基团、脂环族C3-C6基团或具有7-24个碳原子的芳亚烷基,其中每个基团R7任选地包含氧或硫原子,并且每个基团R7任选地经C1-4烷基取代;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基或(甲基)丙烯酰基团;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
L1和L2独立地是相同或不同的具有1-4个碳的直链或支链亚烷基;
X1是直接键或经R5取代的氮原子;
X2是氧原子;
p和q是整数0-4;和
r是整数1-6;
其中x和y是组分(i)和(ii)的摩尔当量。
6.根据权利要求1所述的牙科材料,其中所述至少一种可聚合的树脂单体选自2,2′-双[4-(3-甲基丙烯酰氧-2-羟基丙氧基)-苯基]丙烷(bis-GMA)、四甘醇二(甲基)丙烯酸酯(TEGDMA)、氨基甲酸酯二甲基丙烯酸酯(UDMA)、三羟甲基丙烷三甲基丙烯酸酯、(甲基)丙烯酸C1-C20烷基酯、芳族甲基丙烯酸酯和(甲基)丙烯酸羟烷基酯。
7.根据权利要求1所述的牙科材料,其中所述可聚合的水解稳定的多环酰胺单体的存在量是1-99%w/w,基于所述牙科材料的总重量。
8.根据权利要求1所述的牙科材料,其中所述光引发剂和氧化还原引发剂中的至少一种的存在量是0.01-5%w/w,基于所述牙科材料的总重量。
9.根据权利要求1所述的牙科材料,其中所述至少一种可聚合的树脂单体的存在量是1-99%w/w,基于所述牙科材料的总重量。
10.根据权利要求1所述的牙科材料,其中所述牙科材料是牙科复合材料或牙科水门汀并且包括颗粒状填料。
11.根据权利要求10所述的牙科材料,其中所述颗粒状填料的存在量是10-90%w/w,基于所述牙科复合材料的总重量。
12.根据权利要求1所述的牙科材料,其进一步包含稳定剂、一种或多种阻聚剂、一种或多种溶剂及其组合。
13.一种固化的牙科材料,其通过聚合包含以下各项的混合物来获得:
(i)可聚合的水解稳定的多环酰胺单体,其包含式(I)的化合物:
其中
R1、R2、R3和R4是彼此独立的,并且表示氢、C1-4烷基或C5-C18芳基;
R5是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基;其中每个基团R5任选地经C1-4烷基、C1-4烷氧基或羟基中的一种或多种取代;
R6是氢原子、C1-6烷基、C3-10环烷基、C7-C12芳烷基、C6-C10芳基、酯或酰胺基团,
X是-CH2;
m是整数1-6;和
Z是m价未取代的或取代的C1-C18亚烷基、未取代的或取代的C3-C8环亚烷基、未取代的或取代的芳亚烷基、未取代的或取代的C5-C18亚芳基或未取代的或取代的C3-C18杂亚芳基;其中每个未取代的或取代的基团Z任选地包括下面的至少一种:1-6个氧、硅、硫原子或NR9,其中R9表示氢原子、直链或支化或环状的C1-6烷基;
(ii)至少一种可聚合的树脂单体,其具有至少一个(甲基)丙烯酸酯基团、(甲基)丙烯酰胺基团、烯丙基或乙烯基;
(iii)任选的颗粒状填料;和
(iv)光引发剂和氧化还原引发剂中的至少一种。
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AU2020259278A1 (en) | 2021-10-07 |
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