JP2016190805A - 歯科用表面処理剤組成物 - Google Patents
歯科用表面処理剤組成物 Download PDFInfo
- Publication number
- JP2016190805A JP2016190805A JP2015071480A JP2015071480A JP2016190805A JP 2016190805 A JP2016190805 A JP 2016190805A JP 2015071480 A JP2015071480 A JP 2015071480A JP 2015071480 A JP2015071480 A JP 2015071480A JP 2016190805 A JP2016190805 A JP 2016190805A
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- Prior art keywords
- surface treatment
- compound
- dental surface
- acid
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 239000012756 surface treatment agent Substances 0.000 title abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 41
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 33
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 22
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 21
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims description 47
- 238000004381 surface treatment Methods 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 239000003505 polymerization initiator Substances 0.000 claims description 25
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 23
- 229910052742 iron Inorganic materials 0.000 claims description 12
- 229940125904 compound 1 Drugs 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 150000003611 tocopherol derivatives Chemical class 0.000 claims description 5
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims 1
- 230000007774 longterm Effects 0.000 abstract description 6
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- 239000002253 acid Substances 0.000 description 18
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- 239000010452 phosphate Substances 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
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- 210000004268 dentin Anatomy 0.000 description 11
- 235000002639 sodium chloride Nutrition 0.000 description 11
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- 159000000000 sodium salts Chemical class 0.000 description 8
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 7
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- 239000000463 material Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 5
- 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 4
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- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000000996 L-ascorbic acids Chemical class 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
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- 238000004040 coloring Methods 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 239000003479 dental cement Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JPFQBQKZQZFGNE-UHFFFAOYSA-N 4-(4-oxo-4-propoxybutanoyl)peroxycarbonylphthalic acid Chemical compound C(CCC(=O)OCCC)(=O)OOC(C1=CC(=C(C=C1)C(=O)O)C(=O)O)=O JPFQBQKZQZFGNE-UHFFFAOYSA-N 0.000 description 3
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 229930003268 Vitamin C Natural products 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
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- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 239000011732 tocopherol Substances 0.000 description 3
- 229930003799 tocopherol Natural products 0.000 description 3
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- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
- 235000019154 vitamin C Nutrition 0.000 description 3
- 239000011718 vitamin C Substances 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JDKSTARXLKKYPS-UHFFFAOYSA-N 2-[10-(2-methylprop-2-enoyloxy)decyl]propanedioic acid Chemical compound CC(=C)C(=O)OCCCCCCCCCCC(C(O)=O)C(O)=O JDKSTARXLKKYPS-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
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- 229910021594 Copper(II) fluoride Inorganic materials 0.000 description 2
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- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
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- 238000004132 cross linking Methods 0.000 description 2
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 2
- FWBOFUGDKHMVPI-UHFFFAOYSA-K dicopper;2-oxidopropane-1,2,3-tricarboxylate Chemical compound [Cu+2].[Cu+2].[O-]C(=O)CC([O-])(C([O-])=O)CC([O-])=O FWBOFUGDKHMVPI-UHFFFAOYSA-K 0.000 description 2
- GNGACRATGGDKBX-UHFFFAOYSA-N dihydroxyacetone phosphate Chemical compound OCC(=O)COP(O)(O)=O GNGACRATGGDKBX-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Dental Preparations (AREA)
Abstract
【解決手段】 (a1)遷移金属化合物と、(b)水と、(c1)一分子中にリン酸基及びアルコール性水酸基をそれぞれ一つ以上含有する化合物、および/または(d1)環状構造を有する共役的パイ電子系に属する水酸基を有する化合物、を含有することを特徴とする、歯科用表面処理剤組成物。
【選択図】なし
Description
酸性基含有重合性単量体は、カルボン酸基、リン酸基、スルホン酸基及びホスホン酸基等の酸性基を1分子中に少なくとも1個含有する単量体を示す。また重合性基として、アクリロイル基、メタクリロイル基、スチリル基、ビニル基、アリル基等のラジカル重合可能な不飽和基を1分子中に少なくとも1個含有するのが好ましい。
これらの酸性基含有重合性単量体は必要に応じて複数を混合して用いることもできる。
上記酸性基含有重合性単量体の中でも、カルボン酸基を含有する重合性単量体及びリン酸基を含有する重合性単量体が歯質に対する接着性に優れることから好ましく、さらに双方を組み合わせることがより好ましい。
重合禁止剤としては、ハイドロキノンモノメチルエーテル、ハイドロキノン、4-tert-ブチルフェノール等を添加する事ができる。
顔料、染料としては、歯科用硬化性組成物または歯科用表面処理剤組成物に公知の染料、顔料を配合する事ができる。
本発明の歯科用表面処理剤組成物を用いて、歯質を前処理し、各種補綴物と歯質を上記のような(メタ)アクリレート系歯科用レジンセメントを用いて接着するのが好ましい。
以下に示される組成を有する実施例1〜4の歯科用表面処理剤組成物を、以下のように調整した。他に記載されない限り、全ての値は、重量(重量部)による。
[(a1)遷移金属化合物]
塩化第一鉄四水和物
[(b)水]
蒸留水
[(c1)一分子中にリン酸基及びアルコール性水酸基をそれぞれ一つ以上含有する化合物]
グリセロリン酸2ナトリウム四水和物
[(d1)環状構造を有する共役的パイ電子系に属する水酸基を有する化合物]
±-α-トコフェロール
アスコルビン酸
[(e)重合性単量体]
4-META
2−ヒドロキシエチルメタクリレート(HEMA)
UDMA
[(f)水溶性有機溶媒]
アセトン
[重合禁止剤]
ジブチルヒドロキシトルエン(BHT)
表1に示す原料を常温下(25℃)で混合して均一溶液を調整した。なお、本溶液は容量100 mlのガラスサンプル瓶中で作製した。次いで、遮光性の樹脂製密閉容器に充填し、接着性能の評価と熱安定性能の評価に使用した。
本発明において、接着性能の評価は、特に限定しない限り次のようにして行ったものである。
接着試験方法の一例として牛歯象牙質を、注水、指圧下で耐水エメリー紙180番まで研削し、平滑な面を得た後、圧縮空気を吹き付けて水分を除去する。こうして形成した研削面に、接着面積を直径4.8mmとなるように規定した。
本発明において、熱安定性能の評価は、特に限定しない限り次のようにして行ったものである。
各実施例及び比較例で製造したプライマー組成物のそれぞれを45℃にて50日で保存した。次いで、色差計(コニカミノルタ製)を用いて上記プライマー組成物の色差を測定する事で、各溶液の着色の程度を調べた。
実施例1〜4及び比較例1の接着性能評価と熱安定性評価の結果について表1に示す。
Claims (9)
- (a1)遷移金属化合物と、(b)水と、(c1)一分子中にリン酸基及びアルコール性水酸基をそれぞれ一つ以上含有する化合物、および/または(d1)環状構造を有する共役的パイ電子系に属する水酸基を有する化合物、を含有することを特徴とする、歯科用表面処理剤組成物。
- 前記(a1)遷移金属化合物が(a1-1)鉄および/または銅よりなる化合物である請求項1記載の歯科用表面処理剤組成物。
- 前記(c1)一分子中にリン酸基及びアルコール性水酸基をそれぞれ一つ以上含有する化合物が(c1-1)モル質量が120〜500g/molとなる範囲の化合物であって、かつ、重量比において前記(a1)遷移金属化合物1に対して40以下の範囲にある請求項1または2に記載の歯科用表面処理剤組成物。
- 前記(d1)環状構造を有する共役的パイ電子系に属する水酸基を有する化合物が(d1-1)トコフェロール誘導体であって、かつ、重量比において前記(a1)遷移金属化合物1に対して40以下の範囲にある請求項1〜3のいずれかに記載の歯科用表面処理剤組成物。
- 前記(d1)環状構造を有する共役的パイ電子系に属する水酸基を有する化合物が(d1-2)アスコルビン酸誘導体であって、かつ、重量比において前記(a1)遷移金属化合物1に対して40以下の範囲にある請求項1〜4のいずれかに記載の歯科用表面処理剤組成物。
- さらに(e)重合性単量体を含む請求項1〜5のいずれかに記載の歯科用表面処理剤組成物。
- さらに(f)水溶性有機溶媒を含む請求項1〜6のいずれかに記載の歯科用表面処理剤組成物。
- さらに(g)重合開始剤を含む請求項1〜7のいずれかに記載の歯科用表面処理剤組成物。
- さらに(h)増粘剤を含む請求項1〜8のいずれかに記載の歯科用表面処理剤組成物。
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CN110859755A (zh) * | 2018-08-27 | 2020-03-06 | 中国科学院化学研究所 | 一种用于治疗牙髓病变的盖髓剂及其制备方法和用途 |
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