JP2016513071A5 - - Google Patents
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- JP2016513071A5 JP2016513071A5 JP2015547398A JP2015547398A JP2016513071A5 JP 2016513071 A5 JP2016513071 A5 JP 2016513071A5 JP 2015547398 A JP2015547398 A JP 2015547398A JP 2015547398 A JP2015547398 A JP 2015547398A JP 2016513071 A5 JP2016513071 A5 JP 2016513071A5
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- 239000000203 mixture Substances 0.000 claims 13
- 238000003776 cleavage reaction Methods 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 9
- 239000000178 monomer Substances 0.000 claims 5
- 239000011347 resin Substances 0.000 claims 5
- 229920005989 resin Polymers 0.000 claims 5
- 125000000524 functional group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000005842 heteroatoms Chemical group 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000004851 dental resin Substances 0.000 claims 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims 2
- 239000003999 initiator Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000758 substrate Substances 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- VIYWVRIBDZTTMH-UHFFFAOYSA-N 2-[4-[2-[4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCCOC(=O)C(C)=C)C=C1 VIYWVRIBDZTTMH-UHFFFAOYSA-N 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N 2-hydroxyethyl 2-methylacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N Cyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 1
- UBJVUCKUDDKUJF-UHFFFAOYSA-N Diallyl sulfide Chemical compound C=CCSCC=C UBJVUCKUDDKUJF-UHFFFAOYSA-N 0.000 claims 1
- 229940116336 Glycol Dimethacrylate Drugs 0.000 claims 1
- 229940117969 NEOPENTYL GLYCOL Drugs 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 claims 1
- BIAPHJKUKHWRMP-UHFFFAOYSA-N [SiH4].C=C1CCCCSS1 Chemical compound [SiH4].C=C1CCCCSS1 BIAPHJKUKHWRMP-UHFFFAOYSA-N 0.000 claims 1
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 1
- 229940008075 allyl sulfide Drugs 0.000 claims 1
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- BHBPJIPGXGQMTE-UHFFFAOYSA-N ethane-1,2-diol;2-methylprop-2-enoic acid Chemical compound OCCO.CC(=C)C(O)=O.CC(=C)C(O)=O BHBPJIPGXGQMTE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000000945 filler Substances 0.000 claims 1
- 229910052809 inorganic oxide Inorganic materials 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- QPUODVCELBQSLF-UHFFFAOYSA-N oxiran-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CO1.CC(=C)C(=O)OCC1CO1 QPUODVCELBQSLF-UHFFFAOYSA-N 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
Claims (20)
- Zが、(メタ)アクリレート又はビニル基を含む、請求項1に記載の付加開裂オリゴマー。
- yが1である、請求項1に記載の付加開裂オリゴマー。
- yが0である、請求項1に記載の付加開裂オリゴマー。
- x+yが0〜60である、請求項1に記載の付加開裂オリゴマー。
- 請求項1に記載の付加開裂オリゴマーを調製する方法であって、
式a)R1−O−CO−RA−CO−O−R1で表される化合物[式中、RAが(ヘテロ)ヒドロカルビル基であり、R1がH又はアルキルである。]を、
式b)X2−RB−X2で表される化合物[式中、RBが(ヘテロ)ヒドロカルビル基であり、X2が、化合物a)の酸官能基又はエステル官能基と反応する官能基である。]、及び
式c)(Z)d−X3で表される化合物[式中、Zがエチレン性不飽和基を含み、X3が、化合物a)又はb)の前記官能基と反応する反応性官能基であり、dが1又は2である。]と組み合わせることによって、調製する方法。 - 化合物a)が、化合物b)に対して化学量論的に過剰である、請求項7に記載の方法。
- R1がHであり、X2がエポキシ基を含み、X3がイソシアネート基を含む、請求項8に記載の方法。
- 化合物c)の量のモル当量が、化合物a)の量から化合物b)の量を引いたものの2倍以上である、請求項8に記載の方法。
- 化合物b)が、化合物a)に対して化学量論的に過剰である、請求項7に記載の方法。
- 請求項1〜6のいずれか一項に記載の付加開裂オリゴマー、少なくとも1つのフリーラジカル重合性モノマー、及び開始剤を含む、重合性組成物。
- 全モノマーa)〜d)100重量部に基づいて、
a)85〜100重量部の(メタ)アクリル酸エステルと、
b)0〜15重量部の酸官能性エチレン性不飽和モノマーと、
c)0〜10重量部の非酸官能性エチレン性不飽和極性モノマーと、
d)0〜5部のビニルモノマーと、
e)0〜100部の多官能性(メタ)アクリレートと、
f)a)〜e)100重量部に基づいて0.1〜12重量部の前記付加開裂オリゴマーと、
g)開始剤と、を含む、請求項12に記載の重合性組成物。 - 0.01〜100部の多官能性(メタ)アクリレートを更に含む、請求項13に記載の重合性組成物。
- 2つの基材を共に結合する方法であって、
請求項12〜14のいずれか一項に記載の重合性組成物を一方又は両方の基材の表面にコーティングする工程と、
前記コーティングされた表面を、任意に圧力と共に、接触させる工程と、
前記重合性組成物を硬化させる工程と、を含む、方法。 - 1つ以上の多官能性(メタ)アクリレートモノマー又は(メタ)アクリレートオリゴマー、及び請求項1〜6のいずれか一項に記載の付加開裂オリゴマーを含む、ハードコート組成物。
- a)0.1〜10重量%の前記付加開裂オリゴマーと、
b)20〜80重量%の多官能性(メタ)アクリレートモノマー及び/又は多官能性(メタ)アクリレートオリゴマーと、
c)0〜25重量%範囲の(メタ)アクリレート希釈剤と、
d)20〜75重量%のシリカと、を含む、請求項16に記載のハードコート組成物。 - a)少なくとも2つのエチレン性不飽和基を含む少なくとも1つの歯科用樹脂と、
b)請求項1〜6のいずれか一項に記載の付加開裂オリゴマーと、
c)任意に無機酸化物フィラーと、を含む、硬化性歯科用組成物。 - 前記歯科用樹脂が、イソシアヌレート樹脂、トリシクロデカン樹脂、環状アリルスルフィド樹脂;メチレンジチエパンシラン樹脂;及びポリ(メタ)アクリロイル含有樹脂、又はこれらの混合物である、請求項18に記載の歯科用組成物。
- 前記歯科用組成物が、エトキシ化ビスフェノールAジメタクリレート、2−ヒドロキシエチルメタクリレート、ビスフェノールAジグリシジルジメタクリレート、ウレタンジメタクリレート、トリエチレングリコールジメタクリレート、グリセロールジメタクリレート、エチレングリコールジメタクリレート、ネオペンチルグリコールジメタクリレート(NPGDMA)、ポリエチレングリコールジメタクリレート、及びこれらの混合物から選択される少なくとも1つの他の(メタ)アクリレートモノマーを更に含む、請求項18又は19に記載の歯科用組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261738067P | 2012-12-17 | 2012-12-17 | |
US61/738,067 | 2012-12-17 | ||
PCT/US2013/072250 WO2014099317A1 (en) | 2012-12-17 | 2013-11-27 | Addition-fragmentation oligomers |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2016513071A JP2016513071A (ja) | 2016-05-12 |
JP2016513071A5 true JP2016513071A5 (ja) | 2016-12-22 |
JP6306044B2 JP6306044B2 (ja) | 2018-04-04 |
Family
ID=49780392
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015547398A Expired - Fee Related JP6306044B2 (ja) | 2012-12-17 | 2013-11-27 | 付加開裂オリゴマー |
Country Status (6)
Country | Link |
---|---|
US (1) | US9463146B2 (ja) |
EP (1) | EP2931756B1 (ja) |
JP (1) | JP6306044B2 (ja) |
KR (1) | KR102008353B1 (ja) |
CN (1) | CN104870484B (ja) |
WO (1) | WO2014099317A1 (ja) |
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WO2014172138A1 (en) | 2013-04-15 | 2014-10-23 | 3M Innovative Properties Company | Dental composition containing high refractive index monomers |
EP3046962B1 (en) | 2013-09-20 | 2018-05-23 | 3M Innovative Properties Company | Trithiocarbonate-containing addition-fragmentation agents |
CN105683257B (zh) | 2013-10-16 | 2018-02-13 | 3M创新有限公司 | 包含烯丙基二硫化物的加成‑断裂低聚物 |
US9730864B2 (en) * | 2014-02-18 | 2017-08-15 | 3M Innovative Properties Company | Addition-fragmentation oligomers having high refractive index groups |
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US10479848B2 (en) * | 2015-02-20 | 2019-11-19 | 3M Innovative Properties Company | Addition-fragmentation oligomers |
CN109476987A (zh) * | 2016-07-20 | 2019-03-15 | 3M创新有限公司 | 用于量子点的稳定苯乙烯系聚合物 |
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JP2022533453A (ja) | 2019-05-24 | 2022-07-22 | コベストロ (ネザーランズ) ビー.ヴィー. | 強化された高速加工性を備えた光ファイバーをコーティングするための放射線硬化性組成物 |
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-
2013
- 2013-11-27 US US14/652,134 patent/US9463146B2/en active Active
- 2013-11-27 EP EP13808374.6A patent/EP2931756B1/en active Active
- 2013-11-27 CN CN201380065942.1A patent/CN104870484B/zh active Active
- 2013-11-27 JP JP2015547398A patent/JP6306044B2/ja not_active Expired - Fee Related
- 2013-11-27 KR KR1020157018846A patent/KR102008353B1/ko active IP Right Grant
- 2013-11-27 WO PCT/US2013/072250 patent/WO2014099317A1/en active Application Filing
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