JP2021088150A - 光造形用樹脂組成物 - Google Patents
光造形用樹脂組成物 Download PDFInfo
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- JP2021088150A JP2021088150A JP2019220658A JP2019220658A JP2021088150A JP 2021088150 A JP2021088150 A JP 2021088150A JP 2019220658 A JP2019220658 A JP 2019220658A JP 2019220658 A JP2019220658 A JP 2019220658A JP 2021088150 A JP2021088150 A JP 2021088150A
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- acrylate
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- -1 acryloyloxy group Chemical group 0.000 claims description 102
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 24
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 11
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
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- 239000000178 monomer Substances 0.000 description 5
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
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- 239000010734 process oil Substances 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
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- UCWHUQORPNJRMB-UHFFFAOYSA-N (4-phenoxyphenyl)methyl prop-2-enoate Chemical compound C1=CC(COC(=O)C=C)=CC=C1OC1=CC=CC=C1 UCWHUQORPNJRMB-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-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
- ZUZAETTVAMCNTO-UHFFFAOYSA-N 2,3-dibutylbenzene-1,4-diol Chemical compound CCCCC1=C(O)C=CC(O)=C1CCCC ZUZAETTVAMCNTO-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
[1](メタ)アクリロイルオキシ基が直接結合した多環芳香族炭化水素化合物(A)、多環芳香族炭化水素を含有しないα,β−不飽和二重結合基含有化合物(B)、及び光重合開始剤(C)を含有する光造形用樹脂組成物。
[2]前記(メタ)アクリロイルオキシ基が直接結合した多環芳香族炭化水素化合物(A)がナフタレンを含む化合物である、[1]に記載の光造形用樹脂組成物。
[3]前記(メタ)アクリロイルオキシ基が直接結合した多環芳香族炭化水素化合物(A)が単官能(メタ)アクリロイル基含有化合物である、[1]又は[2]に記載の光造形用樹脂組成物。
[4]前記多環芳香族炭化水素を有しないα,β−不飽和二重結合基含有化合物(B)が、ウレタン結合を有しない単官能(メタ)アクリル酸エステル化合物(B)−1を含有する、[1]〜[3]のいずれかに記載の光造形用樹脂組成物。
[5]前記ウレタン結合を有しない単官能(メタ)アクリル酸エステル化合物(B)−1が、芳香環を少なくとも1個有する単官能(メタ)アクリル酸エステル化合物である、[4]に記載の光造形用樹脂組成物。
[6]前記多環芳香族炭化水素を有しないα,β−不飽和二重結合基含有化合物(B)が、ウレタン化(メタ)アクリル化合物(B)−2を含有する、[1]〜[5]のいずれかに記載の光造形用樹脂組成物。
[7]前記ウレタン化(メタ)アクリル化合物(B)−2が、1分子内に、ポリエステル、ポリカーボネート、ポリウレタン、ポリエーテル、ポリ共役ジエン、及び水添ポリ共役ジエンからなる群より選ばれる少なくとも1種の構造、並びにウレタン結合、を含有する(メタ)アクリレートである、[6]に記載の光造形用樹脂組成物。
[8][1]〜[7]のいずれかに記載の光造形用樹脂組成物の硬化物からなる、歯科材料。
[9][1]〜[7]のいずれかに記載の光造形用樹脂組成物の硬化物からなる、歯科用マウスピース。
[10][1]〜[7]のいずれかに記載の光造形用樹脂組成物の硬化物からなる、義歯床材料。
[11][1]〜[7]のいずれかに記載の光造形用樹脂組成物の硬化物からなる、睡眠障害治療材料。
[12][1]〜[7]のいずれかに記載の光造形用樹脂組成物を用いて、光学的立体造形法によって立体造形物を製造する方法。
(メタ)アクリロイルオキシ基が直接結合した多環芳香族炭化水素化合物(A)(以下、単に「多環芳香族炭化水素化合物(A)」と称することがある)を光造形用樹脂組成物が含むことにより、光照射後の立体造形物の融点(Tm)又はガラス転移温度(Tg)が向上することで、内部凝集力の向上がさらに図られ、強度を含む靭性の良好な立体造形物を形成することが可能となる。
本発明の光造形用樹脂組成物は、多環芳香族炭化水素を含有しないα,β−不飽和二重結合基含有化合物(B)(以下、単にα,β−不飽和二重結合基含有化合物(B)と称することがある)を含有する。α,β−不飽和二重結合基含有化合物(B)は、本発明の光造形用樹脂組成物において、光造形用樹脂組成物の硬化物に靭性を付与するために用いられる。また、α,β−不飽和二重結合基含有化合物(B)を用いることで、光造形用樹脂組成物の臭気を抑えることができる。
本発明に用いられる光重合開始剤(C)は、一般工業界で使用されている光重合開始剤から選択して使用でき、中でも歯科用途に使用されている光重合開始剤が好ましい。
NPA:2−ナフチルアクリレート(共栄社化学株式会社製)
NPMA:2−ナフチルメタクリレート(共栄社化学株式会社製)
[単官能(メタ)アクリル酸エステル化合物(B)−1]
EPPA:エトキシ化−o−フェニルフェノールアクリレート(新中村化学工業株式会社製)
POBA:m−フェノキシベンジルメタクリレート(共栄社化学株式会社製)
後述の合成例1及び2により製造したウレタン化(メタ)アクリル化合物(B)−2−1及び(B)−2−2を用いた。
TPO:2,4,6−トリメチルベンゾイルジフェニルホスフィンオキシド
BAPO:ビス(2,4,6−トリメチルベンゾイル)フェニルホスフィンオキシド
BHT:3,5−ジ−t−ブチル−4−ヒドロキシトルエン
(1)撹拌機、温度調節器、温度計及び凝縮器を備えた内容積5Lの四つ口フラスコに、イソホロンジイソシアネート250g、及びジラウリル酸ジ−n−ブチルスズ0.15gを添加して、撹拌下に70℃に加熱した。
(2)一方、ポリエステルポリオール(株式会社クラレ製「クラレポリオール(登録商標) P−2030」;イソフタル酸と3−メチル−1,5−ペンタンジオールからなるポリオール、重量平均分子量Mw2000)2500gを側管付きの滴下漏斗に添加し、この滴下漏斗の液を、上記(1)のフラスコ中に滴下した。なお、上記(1)のフラスコ中の溶液を撹拌しつつ、フラスコの内温を65〜75℃に保持しながら4時間かけて等速で滴下した。さらに、滴下終了後、同温度で2時間撹拌して反応させた。
(3)次いで、別の滴下漏斗に添加した2−ヒドロキシエチルアクリレート150gとヒドロキノンモノメチルエーテル0.4gとを均一に溶解させた液をフラスコの内温を55〜65℃に保持しながら2時間かけて等速で滴下した後、フラスコ内の溶液の温度を70〜80℃に保持しながら4時間反応させることにより、ウレタン化(メタ)アクリル化合物(B)−2−1を得た。GPC分析によるウレタン化(メタ)アクリル化合物(B)−2−1の重量平均分子量Mwは2700であった。
(1)撹拌機、温度調節器、温度計及び凝縮器を備えた内容積5Lの四つ口フラスコに、イソホロンジイソシアネート250g、及びジラウリル酸ジ−n−ブチルスズ0.15gを添加して、撹拌下に70℃に加熱した。
(2)一方、ポリエステルポリオール(株式会社クラレ製「クラレポリオール(登録商標) P−2050」;セバシン酸と3−メチル−1,5−ペンタンジオールからなるポリオール、重量平均分子量Mw2000)2500gを側管付きの滴下漏斗に添加し、この滴下漏斗の液を、上記(1)のフラスコ中に滴下した。なお、上記(1)のフラスコ中の溶液を撹拌しつつ、フラスコの内温を65〜75℃に保持しながら4時間かけて等速で滴下した。さらに、滴下終了後、同温度で2時間撹拌して反応させた。
(3)次いで、別の滴下漏斗に添加した2−ヒドロキシエチルアクリレート150gとヒドロキノンモノメチルエーテル0.4gとを均一に溶解させた液をフラスコの内温を55〜65℃に保持しながら2時間かけて等速で滴下した後、フラスコ内の溶液の温度を70〜80℃に保持しながら4時間反応させることにより、ウレタン化(メタ)アクリル化合物(B)−2−1を得た。GPC分析によるウレタン化(メタ)アクリル化合物(B)−2−2の重量平均分子量Mwは2600であった。
表1及び表2に示す分量で各成分を常温(20℃±15℃、JIS(日本工業規格) Z 8703:1983)下で混合して、実施例1〜6及び比較例1〜5に係る光造形用樹脂組成物としてのペーストを調製した。
各実施例及び各比較例に係る光造形用樹脂組成物について、光造形機(DWS社製 DIGITALWAX(登録商標) 020D)を用いて硬化させ、厚さ3.3mm×幅10.0mm×長さ64.0mmの試験片の造形を行った(n=5)。試験片として寸法通りのシートが造形可能であった場合を造形可能「○」とし、1回でも立体造形物が得られなかった場合を造形不可「×」とした。なお、造形された試験片を用いて後述の評価を行った。
各実施例及び各比較例に係る光造形用樹脂組成物の硬化物として、JIS T 6501:2012(義歯床用アクリル系レジン)に記載の、造形性の評価で使用した試験片(長さ64.0mm、幅10.0mm、厚さ3.3mm)を作製し、該試験片を空気中で1日保管後、曲げ強さ試験を行って評価し、これを初期値とした。すなわち、万能試験機(株式会社島津製作所製、オートグラフAG−I 100kN)を用いて、クロスヘッドスピード5mm/minで曲げ試験を実施した(n=5)。測定値の平均値を表に示す。試験片の曲げ弾性率としては、0.3〜3.0GPaの範囲が好ましく、0.5〜2.5GPaの範囲がより好ましく、0.8〜2.0GPaの範囲がさらに好ましい。曲げ強さとしては、30MPa以上が好ましく、40MPa以上がより好ましく、50MPa以上がさらに好ましい。破断点変位としては、破断しないことが好ましい。最後まで破断しない、又は変位20mm以上で破断した場合を柔軟性が良好「○」とし、変位10mm超20mm未満で破断した場合を柔軟性が中程度「△」とし、変位10mm以下で破断した場合を柔軟性が悪い「×」とした。靭性としては、破断点変位の評価が「○」であり、曲げ弾性率が0.3〜3.0GPaの範囲であり、かつ曲げ強さが30MPa以上であるものを合格とした。
靭性の測定で作製した硬化物と同様にして作製した、各実施例及び各比較例に係る光造形用樹脂組成物の硬化物について、37℃水中浸漬168時間後、上記曲げ試験と同様に、曲げ強さを測定した(n=5)。上記靭性における曲げ強さの測定結果を初期の曲げ強さとし、初期の曲げ強さに対する、37℃水中浸漬168時間後の曲げ強さの変化率(低下率)を算出した。曲げ強さの変化率(低下率)が10%以下であれば耐水性に優れ、7%以下であればより耐水性に優れる。算出した値の平均値を表に示した。
曲げ強さの変化率(低下率)(%)=〔{初期の曲げ強さ(MPa)−37℃水中浸漬168時間後の曲げ強さ(MPa)}/初期の曲げ強さ(MPa)〕×100
各実施例及び各比較例に係る光造形用樹脂組成物について、10人のパネラーで臭気を評価した(n=1)。10人のパネラーのうち、不快な臭気を感じた人が2人未満であったものを「○」、不快な臭気を感じた人が2人以上5人未満であったものを「△」、不快な臭気を感じた人が5人以上であったものを「×」とした。不快な臭気を感じなければ特に問題はない。
Claims (12)
- (メタ)アクリロイルオキシ基が直接結合した多環芳香族炭化水素化合物(A)、多環芳香族炭化水素を含有しないα,β−不飽和二重結合基含有化合物(B)、及び光重合開始剤(C)を含有する光造形用樹脂組成物。
- 前記(メタ)アクリロイルオキシ基が直接結合した多環芳香族炭化水素化合物(A)がナフタレンを含む化合物である、請求項1に記載の光造形用樹脂組成物。
- 前記(メタ)アクリロイルオキシ基が直接結合した多環芳香族炭化水素化合物(A)が単官能(メタ)アクリロイル基含有化合物である、請求項1又は2に記載の光造形用樹脂組成物。
- 前記多環芳香族炭化水素を有しないα,β−不飽和二重結合基含有化合物(B)が、ウレタン結合を有しない単官能(メタ)アクリル酸エステル化合物(B)−1を含有する、請求項1〜3のいずれか1項に記載の光造形用樹脂組成物。
- 前記ウレタン結合を有しない単官能(メタ)アクリル酸エステル化合物(B)−1が、芳香環を少なくとも1個有する単官能(メタ)アクリル酸エステル化合物である、請求項4に記載の光造形用樹脂組成物。
- 前記多環芳香族炭化水素を有しないα,β−不飽和二重結合基含有化合物(B)が、ウレタン化(メタ)アクリル化合物(B)−2を含有する、請求項1〜5のいずれか1項に記載の光造形用樹脂組成物。
- 前記ウレタン化(メタ)アクリル化合物(B)−2が、1分子内に、ポリエステル、ポリカーボネート、ポリウレタン、ポリエーテル、ポリ共役ジエン、及び水添ポリ共役ジエンからなる群より選ばれる少なくとも1種の構造、並びにウレタン結合、を含有する(メタ)アクリレートである、請求項6に記載の光造形用樹脂組成物。
- 請求項1〜7のいずれか1項に記載の光造形用樹脂組成物の硬化物からなる、歯科材料。
- 請求項1〜7のいずれか1項に記載の光造形用樹脂組成物の硬化物からなる、歯科用マウスピース。
- 請求項1〜7のいずれか1項に記載の光造形用樹脂組成物の硬化物からなる、義歯床材料。
- 請求項1〜7のいずれか1項に記載の光造形用樹脂組成物の硬化物からなる、睡眠障害治療材料。
- 請求項1〜7のいずれか1項に記載の光造形用樹脂組成物を用いて、光学的立体造形法によって立体造形物を製造する方法。
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