JP2022510574A - 歯科用組成物のための抗菌性ナノゲルおよび加水分解的に安定な抗菌性ナノゲルのための組成物および方法 - Google Patents
歯科用組成物のための抗菌性ナノゲルおよび加水分解的に安定な抗菌性ナノゲルのための組成物および方法 Download PDFInfo
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- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000012708 photoinduced radical polymerization Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000004928 piperidonyl group Chemical group 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000000565 sealant 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
- 150000004756 silanes Chemical class 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- CSKKAINPUYTTRW-UHFFFAOYSA-N tetradecoxycarbonyloxy tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCC CSKKAINPUYTTRW-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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Abstract
Description
(a)イミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基のうちの少なくとも1つおよび少なくとも1つのエチレン性不飽和基を有する、重合可能な抗菌性モノマー、
(b)少なくとも1つの(メタ)アクリレートもしくは(メタ)アクリルアミド基を有する、少なくとも1種の重合可能な樹脂モノマー、
(c)少なくとも1種の連鎖移動剤、および
(d)開始剤
を含むモノマー混合物から得られる。
式中、
Mはビニルエーテル、ビニルエステル、ビニルアミン、アリル、アクリルアミド、メタクリルアミド、アクリレートもしくはメタクリレート部分であり、
YおよびZは、独立して、同じもしくは異なる、1~4個の炭素を有する、アルキレン、オキシアルキレン、アミノアルキレンもしくはチオアルキレンであるか、または、アリーレン、カーボネート、カルボキシレート、エステル基、アミドまたは直接結合であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2およびR3は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンまたは直接結合であり、
Bはイミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基であり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルまたは直接結合であり、
Xは対イオン部分であり、かつ
nは0~4の整数である。
式中、
Mはビニルエーテル、ビニルエステル、ビニルアミン、アリル、アクリルアミド、メタクリルアミド、アクリレートもしくはメタクリレート部分であり、
Yは1~4個の炭素を有する、アルキレン、オキシアルキレンもしくはチオアルキレンであるか、または、カーボネート、カルボキシレート、エステル基または直接結合であり、
WはO、NR4または直接結合であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2およびR3は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mであり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、
Xは対イオン部分であり、かつ
nは0~1の整数である。
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mであり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、かつ
Xは対イオン部分である。
(a)以下の式:
マイケルドナーはイミダゾールである工程と、
(b)以下の式III:
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mであり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、かつ
Xは対イオン部分である
工程と
を含む。
(a)マイクロ波反応器において溶媒の存在下で、イミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基のうちの少なくとも1つおよび少なくとも1つの(メタ)アクリレート基を有する重合可能な抗菌性モノマー、少なくとも1つの(メタ)アクリレートもしくは(メタ)アクリルアミド基を有する少なくとも1種の重合可能な樹脂モノマー、少なくとも1種の連鎖移動剤および開始剤を1つに合わせる工程と、
(b)重合反応を開始する工程と、
(c)重合後に溶媒から本重合可能な抗菌性ナノゲルを回収する工程と
を含む。
本開示の一態様では、(a)イミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基のうちの少なくとも1つおよび少なくとも1つのエチレン性不飽和基を有する重合可能な抗菌性モノマー、(b)少なくとも1つの(メタ)アクリレートもしくは(メタ)アクリルアミド基を有する少なくとも1種の重合可能な樹脂モノマー、(c)少なくとも1種の連鎖移動剤、および(d)開始剤を含むモノマー混合物から得られる重合可能な抗菌性ナノゲルが提供される。
式中、
Mはビニルエーテル、ビニルエステル、ビニルアミン、アリル、アクリルアミド、メタクリルアミド、アクリレートもしくはメタクリレート部分であり、
YおよびZは、独立して、同じもしくは異なる、1~4個の炭素を有する、アルキレン、オキシアルキレン、アミノアルキレンもしくはチオアルキレンであるか、または、アリーレン、カーボネート、カルボキシレート、エステル基、アミドまたは直接結合であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2およびR3は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンまたは直接結合であり、
Bはイミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基であり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルまたは直接結合であり、
Xは対イオン部分であり、かつ
nは0~4の整数である。
式中、
Mはビニルエーテル、ビニルエステル、ビニルアミン、アリル、アクリルアミド、メタクリルアミド、アクリレートもしくはメタクリレート部分であり、
Yは1~4個の炭素を有する、アルキレン、オキシアルキレンもしくはチオアルキレンであるか、または、カーボネート、カルボキシレート、エステル基または直接結合であり、
WはO、NR4または直接結合であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2およびR3は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mであり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、
Xは対イオン部分であり、かつ
nは0~1の整数である。
本開示の一態様は、一置換の非対称ポリアクリルアミドを得るためのマイケルアクセプターとしての非対称ポリアクリルアミドへの、チオール、アミン、イミダゾールなどのマイケルドナーの選択的付加を伴う、それぞれ加水分解的に安定な樹脂および水溶性の重合可能な樹脂として重合可能な樹脂を調製する方法開発に関する。
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mである。
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mである。
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mであり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、かつ
Xは対イオン部分である。
a)非対称ポリアクリルアミドを、一置換の非対称ポリアクリルアミドを得るために選択される条件下においてマイケルドナーの存在下で反応させる工程であって、
マイケルドナーはイミダゾールである工程と、
(b)一置換の非対称ポリアクリルアミドモノマーのイミダゾールをイミダゾリウムに転換させて、以下の式:
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、かつ
R4は1~4個の炭素を有するアルキルまたはR2Mである
工程と
を含む。
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、かつ
R4は1~4個の炭素を有するアルキルまたはR2Mである。
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、かつ
R4は1~4個の炭素を有するアルキルまたはR2Mである。
本重合可能な抗菌性ナノゲルの特定の実施形態では、少なくとも1つの(メタ)アクリレートまたは(メタ)アクリルアミド基を有する重合可能な樹脂モノマーは、単官能性、二官能性、三官能性もしくは四官能性モノマーからなる群から選択される。
本明細書に開示されている歯科用組成物は、(a)重合可能な抗菌性ナノゲル、(b)重合可能な樹脂、(c)開始剤、(d)充填剤粒子、(e)安定化剤および(f)他の添加剤からなっていてもよい。
歯科用組成物の一実施形態では、重合可能な樹脂は歯科用組成物の10重量%~約95重量%の量で存在してもよい。
ラジカル重合などの連鎖重合では開始剤を使用して熱または光による開始を調節することが多い。
本開示の歯科用組成物は充填剤を含んでいてもよい。
抗菌性ナノゲル改質された樹脂マトリックスと充填剤粒子とを混合することにより抗菌性歯科用複合材を製剤化してもよい。
以下の略語を使用する場合がある。
UDMA:ジ(メタクリロキシエチル)トリメチル-1,6-ヘキサエチレンジウレタン
HEMA:ヒドロキシルエチルメタクリレート
E-BPAD:
NMR分析:300MHzのNMR(Varian社)を使用して構造を解明し、かつ反応処理を監視した。
モノイミダゾール-ビスアクリルアミド(XJ10-123/スキーム1)を以下に記載されているように一段階溶解法により非対称トリスアクリルアミド(FFM3)から調製した。
加水分解的に安定な抗菌性モノマー(ABR-HS3、XJ10-118、スキーム3)をE-BPADのイミダゾール誘導体(モノイミダゾール-モノアクリルアミド、ABR-HS2、スキーム2)から調製することに成功した。
Claims (30)
- (a)(i)イミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基のうちの少なくとも1つおよび(ii)少なくとも1つのエチレン性不飽和基を有する、重合可能な抗菌性モノマー、
(b)少なくとも1つの(メタ)アクリレートもしくは(メタ)アクリルアミド基を有する、少なくとも1種の重合可能な樹脂モノマー、
(c)少なくとも1種の連鎖移動剤、および
(d)開始剤
を含むモノマー混合物から得られる重合可能な抗菌性ナノゲル。 - 前記重合可能な抗菌性モノマーは、式I:
式中、
Mはビニルエーテル、ビニルエステル、ビニルアミン、アリル、アクリルアミド、メタクリルアミド、アクリレートもしくはメタクリレート部分であり、
YおよびZは、独立して、同じもしくは異なる、1~4個の炭素を有する、アルキレン、オキシアルキレン、アミノアルキレンもしくはチオアルキレンであるか、または、アリーレン、カーボネート、カルボキシレート、エステル基、アミドまたは直接結合であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2およびR3は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンまたは直接結合であり、
Bはイミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基であり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルまたは直接結合であり、
Xは対イオン部分であり、かつ
nは0~4の整数である、
請求項1に記載の重合可能な抗菌性ナノゲル。 - 前記重合可能な抗菌性モノマーは、式II:
式中、
Mはビニルエーテル、ビニルエステル、ビニルアミン、アリル、アクリルアミド、メタクリルアミド、アクリレートもしくはメタクリレート部分であり、
Yは1~4個の炭素を有する、アルキレン、オキシアルキレンもしくはチオアルキレンであるか、または、カーボネート、カルボキシレート、エステル基または直接結合であり、
WはO、NR4または直接結合であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2およびR3は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mであり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、
Xは対イオン部分であり、かつ
nは0~1の整数である、
請求項2に記載の重合可能な抗菌性ナノゲル。 - 前記少なくとも1つの(メタ)アクリレートもしくはメタクリルアミド基を有する重合可能な樹脂モノマーは、モノ、ジ、トリおよびテトラ官能性モノマーからなる群から選択される、請求項1に記載の重合可能な抗菌性ナノゲル。
- 前記重合可能な樹脂モノマーは、2,2’-ビス[4-(3-メタクリロキシ-2-ヒドロキシプロポキシ)-フェニル]プロパン(Bis-GMA)、テトラエチレングリコールジ(メタ)アクリレート(TEGDMA)、ウレタンジメタクリレート(UDMA)、トリメチロールプロパントリメタクリレート、C1~C20アルキル(メタ)アクリレート、芳香族メタクリレート、ヒドロキシアルキル(メタ)アクリレートおよび(メタ)アクリルアミドからなる群から選択される、請求項1に記載の重合可能な抗菌性ナノゲル。
- nは1である、請求項3に記載の重合可能な抗菌性ナノゲル。
- 前記重合可能な抗菌性モノマーは前記モノマー混合物のモル全体に対して5~45モル%の範囲で存在する、請求項6に記載の重合可能な抗菌性ナノゲル。
- nは0である、請求項3に記載の重合可能な抗菌性ナノゲル。
- 前記重合可能な抗菌性モノマーは前記モノマー混合物のモル全体に対して5~95モル%の範囲で存在する、請求項8に記載の重合可能な抗菌性ナノゲル。
- 前記重合可能な抗菌性モノマーの前記少なくとも1つのエチレン性不飽和基はメタクリレート基であり、かつ前記重合可能な樹脂モノマーの前記少なくとも1つの(メタ)アクリレート基は、前記重合可能な抗菌性モノマーのメタクリレート基と前記重合可能な樹脂モノマーの前記メタクリレート基との組み合わせが前記モノマー混合物のモル全体に対して50~90モル%の範囲で存在するようなメタクリレート基である、請求項1に記載の重合可能な抗菌性ナノゲル。
- 前記重合可能な樹脂モノマーはC1~C20アルキル(メタ)アクリレートである、請求項10に記載の重合可能な抗菌性ナノゲル。
- 前記重合可能な樹脂モノマーは芳香族メタクリレートである、請求項10に記載の重合可能な抗菌性ナノゲル。
- 前記重合可能な樹脂モノマーはヒドロキシルアルキルアクリレート、ヒドロキシルアルキルメタクリレート、ヒドロキシルアルキルアクリルアミドまたはヒドロキシルアルキル(メタ)アクリルアミドである、請求項10に記載の重合可能な抗菌性ナノゲル。
- 前記連鎖移動剤は1-ドデカンチオールである、請求項1に記載の重合可能な抗菌性ナノゲル。
- 前記開始剤はアゾビスイソブチロニトリルである、請求項1に記載の重合可能な抗菌性ナノゲル。
- 前記開始剤は前記モノマー混合物中の前記エチレン性不飽和基全体の0.5~2.0wt/wtの濃度で存在する、請求項1に記載の重合可能な抗菌性ナノゲル。
- 前記連鎖移動剤は前記モノマー混合物中の前記エチレン性不飽和基全体の25~35%モル/モルの濃度で存在する、請求項1に記載の重合可能な抗菌性ナノゲル。
- 前記重合可能な抗菌性ナノゲルは加水分解的に安定かつ水溶性である、請求項18に記載の重合可能な抗菌性ナノゲル。
- 非対称ポリアクリルアミドを含有する加水分解的に安定かつ水溶性の重合可能なモノマーを形成する方法であって、
前記非対称ポリアクリルアミドを、一置換の非対称ポリアクリルアミドを得るために選択される条件下においてマイケルドナーの存在下で反応させる工程であって、
前記マイケルドナーはイミダゾールである工程を含む方法。 - 前記非対称ポリアクリルアミドを前記マイケルドナーと反応させる前記工程の後に前記一置換の非対称ポリアクリルアミドモノマーの前記イミダゾールをイミダゾリウムに転換させる工程をさらに含む、請求項20に記載の方法。
- 前記一置換の非対称ポリアクリルアミドモノマーの前記イミダゾールをイミダゾリウムに転換する前記工程は、前記一置換の非対称ポリアクリルアミドモノマーをRXと反応させることを含み、
式中、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、かつ
Xは対イオン部分である、
請求項21に記載の方法。 - 以下の式III:
(a)以下の式:
前記マイケルドナーはイミダゾールである工程と、
(b)以下の式III:
式中、
Mはアリル、アクリルアミドもしくはメタクリルアミド部分であり、
R1は2~18個の炭素を有する二価の炭化水素ラジカルであり、
R2は、独立して、同じもしくは異なる、1~4個の炭素を有する直鎖状もしくは分岐鎖状アルキレンであり、
R4は1~4個の炭素を有するアルキルまたはR2Mであり、
Rは4~16個の炭素原子を有する直鎖状もしくは分岐鎖状アルキルであり、かつ
Xは対イオン部分である
工程と
を含む方法。 - (a)マイクロ波反応器において溶媒の存在下で、(i)イミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基のうちの少なくとも1つおよび少なくとも1つの(メタ)アクリレート基を有する重合可能な抗菌性モノマー、(ii)少なくとも1つの(メタ)アクリレートもしくは(メタ)アクリルアミド基を有する少なくとも1種の重合可能な樹脂モノマー、(iii)少なくとも1種の連鎖移動剤および(iv)開始剤を1つに合わせる工程、
(b)重合反応を開始する工程、および
(c)重合後に前記溶媒から重合可能な抗菌性ナノゲルを回収する工程
を含む、前記重合可能な抗菌性ナノゲルを調製する方法。 - 前記溶媒はメチルエチルケトンまたはトルエンである、請求項24に記載の方法。
- 前記溶媒はメチルエチルケトンである、請求項25に記載の方法。
- 抗菌性ナノゲル改質された樹脂マトリックスおよび充填剤粒子を含む抗菌性歯科用複合材であって、
前記抗菌性ナノゲル改質された樹脂マトリックスは重合可能な抗菌性ナノゲル、重合可能な樹脂、開始剤および安定化剤を含み、かつ
前記重合可能な抗菌性ナノゲルは、(i)イミダゾリウム、ピリジニウム、アンモニウムもしくはスルホニウム基のうちの1つおよび少なくとも1つのエチレン性不飽和基を有する重合可能な抗菌性モノマー、(ii)少なくとも1つの(メタ)アクリレートもしくは(メタ)アクリルアミド基を有する重合可能な樹脂モノマー、(iii)少なくとも1種の連鎖移動剤、および(iv)開始剤を含む混合物から得られる、
抗菌性歯科用複合材。 - 前記抗細菌性ナノゲル改質された樹脂マトリックスは前記複合材の総重量に対して0.5~10.0重量%の濃度で前記複合材中に存在する、請求項27に記載の抗菌性歯科用複合材。
- 前記充填剤粒子は前記複合材の総重量に対して30~90重量%の濃度で前記複合材中に存在する、請求項27に記載の抗菌性歯科用複合材。
- 前記複合材は黄色ブドウ球菌に対する抗菌活性を示す、請求項27に記載の抗菌性複合材。
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CN113164329B (zh) | 2023-10-03 |
CN113164329A (zh) | 2021-07-23 |
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