JP7474200B2 - 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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- JP7474200B2 JP7474200B2 JP2020561324A JP2020561324A JP7474200B2 JP 7474200 B2 JP7474200 B2 JP 7474200B2 JP 2020561324 A JP2020561324 A JP 2020561324A JP 2020561324 A JP2020561324 A JP 2020561324A JP 7474200 B2 JP7474200 B2 JP 7474200B2
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- 125000004122 cyclic group Chemical group 0.000 claims description 65
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 59
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y80/00—Products made by additive manufacturing
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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
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
- B29C64/124—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
- B29C64/129—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified characterised by the energy source therefor, e.g. by global irradiation combined with a mask
- B29C64/135—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified characterised by the energy source therefor, e.g. by global irradiation combined with a mask the energy source being concentrated, e.g. scanning lasers or focused light sources
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/30—Auxiliary operations or equipment
- B29C64/307—Handling of material to be used in additive manufacturing
- B29C64/314—Preparation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y10/00—Processes of additive manufacturing
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
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Description
[1]窒素原子を含有する環状構造(a)を有するα,β-不飽和二重結合基含有化合物(A)、常圧沸点280℃以上で、炭素環基を有し、含窒素複素環基を有しない(メタ)アクリル酸エステル化合物(B)、及び光重合開始剤(C)、並びに、必要に応じて、前記α,β-不飽和二重結合基含有化合物(A)及び前記(メタ)アクリル酸エステル化合物(B)に含まれない、分子量500以下の多官能性重合性単量体(E)を含有し、
前記分子量500以下の多官能性重合性単量体(E)の含有量が、光造形用樹脂組成物に含まれる重合性化合物の総量に対して20質量%以下である、光造形用樹脂組成物。
[2]さらに、ウレタン化(メタ)アクリル化合物(D)を含有する、[1]に記載の光造形用樹脂組成物。
[3]前記α,β-不飽和二重結合基含有化合物(A)が、環状構造(a)中に酸素原子及び硫黄原子のいずれも含有しない、[1]又は[2]に記載の光造形用樹脂組成物。
[4]前記α,β-不飽和二重結合基含有化合物(A)が、環状構造(a)を有するN-ビニル基含有化合物(A)-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α,β-不飽和二重結合基含有化合物(A)が、環状構造(a)を有する(メタ)アクリル酸エステル類(A)-2及び/又は環状構造(a)を有する(メタ)アクリルアミド類(A)-3を含有する、[1]~[4]のいずれかに記載の光造形用樹脂組成物。
[6]前記窒素原子を含有する環状構造(a)がピペリジン環である、[1]~[5]のいずれかに記載の光造形用樹脂組成物。
[7]前記α,β-不飽和二重結合基含有化合物(A)が、単官能である、[1]~[6]のいずれかに記載の光造形用樹脂組成物。
[8]前記N-ビニル基含有化合物(A)-1が、N-ビニルカルバゾール、N-ビニル-ε-カプロラクタム、及びN-ビニル-2-ピロリドンからなる群から選ばれる少なくとも1種である、[4]に記載の光造形用樹脂組成物。
[9]前記(メタ)アクリル酸エステル化合物(B)が単官能(メタ)アクリル酸エステル化合物を含有する、[1]~[8]のいずれかに記載の光造形用樹脂組成物。
[10]前記分子量500以下の多官能性重合性単量体(E)を含有しない、[1]~[9]のいずれかに記載の光造形用樹脂組成物。
[11]前記(メタ)アクリル酸エステル化合物(B)が、ホモポリマーのガラス転移温度が40℃以下である単官能(メタ)アクリル酸エステル化合物(B)-1を含有する、[1]~[10]のいずれかに記載の光造形用樹脂組成物。
[12]さらに、ウレタン化(メタ)アクリル化合物(D)を含有し、前記ウレタン化(メタ)アクリル化合物(D)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、[1]~[11]のいずれかに記載の光造形用樹脂組成物。
[13][1]~[12]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。
[14][1]~[12]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、歯科用咬合スプリント。
[15][1]~[12]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。
[16][1]~[12]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、医療材料。
[17][1]~[12]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、睡眠時無呼吸症候群用治療具。
[18][1]~[12]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。
窒素原子を含有する環状構造(a)を有するα,β-不飽和二重結合基含有化合物(A)(以下、単に「α,β-不飽和二重結合基含有化合物(A)」と称することがある)は、窒素原子を含有する環状構造(a)を有するため、光照射後の立体造形物に、環状構造由来の剛直性のため、造形物のガラス転移点(Tg)が向上することで、内部凝集力の向上がさらに図られ、強度や靭性の良好な立体造形物を形成することが可能となり、かつ嵩高い炭化水素基で覆われた窒素原子が樹脂組成物内に含まれるウレタン結合等の極性官能基を保護し、耐水性に優れた立体造形物を形成することも可能となる。このような窒素原子を含有する環状構造(a)としては、例えばヘテロ原子に着目した場合、環状構造(a)上に窒素原子だけを1個以上含有している環状構造、環状構造(a)上に窒素原子と酸素原子との双方を含有している環状構造、及び環状構造(a)上に窒素原子と硫黄原子との双方を含有している環状構造が挙げられる。これらの中でも、環状構造(a)上に窒素原子だけを1個以上含有している環状構造が、耐水性の観点から特に好ましい。なお、本発明における「環状構造(a)上」とは環状骨格及び環状骨格に直接結合している原子までを含む。「環状構造(a)中」とは環状骨格のみを意味し、環状骨格に直接結合している原子を含まない。さらに、α,β-不飽和二重結合基含有化合物(A)は、靭性に優れる観点から単官能であること、すなわちα,β-不飽和二重結合基を1つ有することが好ましい。
本発明の光造形用樹脂組成物は、常圧沸点280℃以上で、炭素環基を有し、含窒素複素環基を有しない(メタ)アクリル酸エステル化合物(B)(以下、単に「(メタ)アクリル酸エステル化合物(B)」と称することがある)を含有する。(メタ)アクリル酸エステル化合物(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及び耐水性を付与するために用いられる。
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。
本発明の光造形用樹脂組成物は、さらに、ウレタン化(メタ)アクリル化合物(D)を含有することが好ましい。ウレタン化(メタ)アクリル化合物(D)は、本発明の光造形用樹脂組成物において硬化性を付与し低粘度化する目的で、また光造形用樹脂組成物の硬化物に靭性を付与する目的で用いられる。
本発明の光造形用樹脂組成物は、靭性の観点から、必要に応じて、前記α,β-不飽和二重結合基含有化合物(A)及び前記(メタ)アクリル酸エステル化合物(B)に含まれない、分子量500以下の多官能性重合性単量体(E)(以下、単に「分子量500以下の多官能性重合性単量体(E)」と称することがある)を含有し、前記分子量500以下の多官能性重合性単量体(E)の含有量が、光造形用樹脂組成物に含まれる重合性化合物の総量に対して20質量%以下であることが重要であり、10質量%以下であることが好ましく、5質量%以下であることがより好ましく、0質量%である(すなわち、分子量500以下の多官能性重合性単量体(E)を含有しない)ことがさらに好ましい。なお、該分子量500以下の多官能性重合性単量体(E)としては、例えば、ネオペンチルグリコールジ(メタ)アクリレート、ジシクロペンタニルジ(メタ)アクリレート、(グリセロールジ(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ブチレングリコールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、1,3-ブタンジオールジ(メタ)アクリレート、1,4-ブタンジオールジ(メタ)アクリレート、1,6-ヘキサンジオールジ(メタ)アクリレート、2-エチル-1,6-ヘキサンジオールジ(メタ)アクリレート、1,9-ノナンジオールジ(メタ)アクリレート、1,10-デカンジオールジ(メタ)アクリレート、1,2-ビス(3-(メタ)アクリロイルオキシ-2-ヒドロキシプロポキシ)エタン、2,2-ビス((メタ)アクリロイルオキシフェニル)プロパン、2,2-ビス〔4-(3-(メタ)アクリロイルオキシ-2-ヒドロキシプロポキシ)フェニル〕プロパン、2,2-ビス(4-(メタ)アクリロイルオキシエトキシフェニル)プロパン、2,2-ビス(4-(メタ)アクリロイルオキシポリエトキシフェニル)プロパン(エトキシ基の平均付加モル数が2.6程度のもの)等の二官能性重合性単量体;トリメチロールプロパントリ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、トリメチロールメタントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート)等の三官能性以上の重合性単量体等が挙げられる。
NVCZ:N-ビニルカルバゾール(東京化成工業株式会社製)
NVCP:N-ビニル-ε-カプロラクタム(東京化成工業株式会社製)
PMPA:ペンタメチルピペリジニルアクリレート(日立化成株式会社製)
PMPMA:ペンタメチルピペリジニルメタクリレート(東京化成工業株式会社製)
[(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)(常圧換算沸点300℃以上、ホモポリマーのTg=30℃)
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)(常圧換算沸点300℃以上、ホモポリマーのTg=-35℃)
[(メタ)アクリル酸エステル化合物(B)-2]
AMA:メタクリル酸9-アントリルメチル(東京化成工業株式会社製)(固体・常圧換算沸点300℃以上、ホモポリマーのTg>40℃)
DCPA:ジシクロペンタニルアクリレート(日立化成株式会社製)(常圧換算沸点260℃)
ATHFA:(5-エチル-1,3-ジオキサン-5-イル)メチルアクリレート(サートマー社製)(常圧換算沸点277℃)
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
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(D-1)及び(D-2)を用いた。
NPGDA:ネオペンチルグリコールジアクリレート(新中村化学工業株式会社製)(常圧換算沸点300℃以上)
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(D-1)を得た。GPC分析によるウレタン化(メタ)アクリル化合物(D-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(D-2)を得た。GPC分析によるウレタン化(メタ)アクリル化合物(D-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1~9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、厚さ3.3mm×幅10.0mm×長さ64mmの試験片の造形を行った(n=5)。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について、JIS T 6501:2012(義歯床用アクリル系レジン)に記載の寸法の、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、曲げ強さ試験を行って評価した。JIS T 6501:2012に従って、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で曲げ強さ試験を実施した(n=5)。各試験片の測定値の平均値を算出し、曲げ強さ及び曲げ弾性率とした。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。
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24時間後、上記曲げ強さ試験と同様に、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24時間後の曲げ強さの変化率(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。
曲げ強さの変化率(低下率)(%)=〔{初期の曲げ強さ(MPa)-37℃水中浸漬24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 (18)
- 窒素原子を含有する環状構造(a)を有するα,β-不飽和二重結合基含有化合物(A)、常圧沸点280℃以上で、炭素環基を有し、含窒素複素環基を有しない(メタ)アクリル酸エステル化合物(B)、光重合開始剤(C)、及びウレタン化(メタ)アクリル化合物(D)、並びに、必要に応じて、前記α,β-不飽和二重結合基含有化合物(A)及び前記(メタ)アクリル酸エステル化合物(B)に含まれない、分子量500以下の多官能性重合性単量体(E)を含有し、
前記(メタ)アクリル酸エステル化合物(B)が有する前記炭素環基が、ビフェニル環、フェノキシベンゼン環、ビシクロ[1.1.1]ペンタン環、(1r,4r)-ビシクロ[2.1.1]ヘキサン環、(1s,4s)-ビシクロ[2.2.1]ヘプタン環、(3aR,4R,7S,7aS)-オクタヒドロ-1H-4,7-メタノインデン環、アダマンタン環、(1s,4s)-ビシクロ[2.2.1]ヘプト-2-エン環、(3aR,4R,7R,7aR)-ヘキサヒドロ-1H-4,7-メタノインデン環、シクロペンタン環、シクロヘキサン環、シクロヘプタン環、シクロペンテン環、シクロヘキセン環、シクロヘプテン環、ベンゼン環、ナフタレン環、フルオレン環、フェナントレン環、及びアントラセン環からなる群より選ばれる少なくとも1種であり、
前記α,β-不飽和二重結合基含有化合物(A)の含有量が、α,β-不飽和二重結合基含有化合物(A)、(メタ)アクリル酸エステル化合物(B)、及びウレタン化(メタ)アクリル化合物(D)の総量において、1.0~80質量%であり、
前記(メタ)アクリル酸エステル化合物(B)の含有量が、前記総量において、1.0~90質量%であり、
前記光重合開始剤(C)の含有量が前記総量100質量部に対して、0.01~20質量部であり、
前記ウレタン化(メタ)アクリル化合物(D)の含有量が、前記総量において、1~98質量%であり、
前記分子量500以下の多官能性重合性単量体(E)の含有量が、光造形用樹脂組成物に含まれる重合性化合物の総量に対して20質量%以下である、歯科材料用又は医療材料用光造形用樹脂組成物。 - 前記α,β-不飽和二重結合基含有化合物(A)が、環状構造(a)中に酸素原子及び硫黄原子のいずれも含有しない、請求項1に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記α,β-不飽和二重結合基含有化合物(A)が、環状構造(a)を有するN-ビニル基含有化合物(A)-1を含有する、請求項1又は2に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記α,β-不飽和二重結合基含有化合物(A)が、環状構造(a)を有する(メタ)アクリル酸エステル類(A)-2及び/又は環状構造(a)を有する(メタ)アクリルアミド類(A)-3を含有する、請求項1~3のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記窒素原子を含有する環状構造(a)がピペリジン環である、請求項1~4のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記α,β-不飽和二重結合基含有化合物(A)が、単官能である、請求項1~5のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記N-ビニル基含有化合物(A)-1が、N-ビニルカルバゾール、N-ビニル-ε-カプロラクタム、及びN-ビニル-2-ピロリドンからなる群から選ばれる少なくとも1種である、請求項3に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記(メタ)アクリル酸エステル化合物(B)が単官能(メタ)アクリル酸エステル化合物を含有する、請求項1~7のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記単官能(メタ)アクリル酸エステル化合物が、芳香環を2個以上含有する単官能(メタ)アクリル酸エステル化合物を含有する、請求項8に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記分子量500以下の多官能性重合性単量体(E)を含有しない、請求項1~9のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 前記(メタ)アクリル酸エステル化合物(B)が、ホモポリマーのガラス転移温度が40℃以下である単官能(メタ)アクリル酸エステル化合物(B)-1を含有する、請求項1~10のいずれか1項に記載の歯科材料用又は医療材料用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(D)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1~11のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物。
- 請求項1~12のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物の硬化物からなる、歯科材料。
- 請求項1~12のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物の硬化物からなる、歯科用咬合スプリント。
- 請求項1~12のいずれか1項に記載の歯科材料用又は医療材料用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1~12のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物の硬化物からなる、医療材料。
- 請求項1~12のいずれか1項に記載の歯科材料用又は医療材料用光造形用樹脂組成物の硬化物からなる、睡眠時無呼吸症候群用治療具。
- 請求項1~12のいずれか1項に記載の歯科材料用又は医療材料用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歯科材料用又は医療材料を製造する方法。
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