JP6790692B2 - 光学的立体造形用活性エネルギー線重合性樹脂組成物、及び立体造形物 - Google Patents
光学的立体造形用活性エネルギー線重合性樹脂組成物、及び立体造形物 Download PDFInfo
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- JP6790692B2 JP6790692B2 JP2016196585A JP2016196585A JP6790692B2 JP 6790692 B2 JP6790692 B2 JP 6790692B2 JP 2016196585 A JP2016196585 A JP 2016196585A JP 2016196585 A JP2016196585 A JP 2016196585A JP 6790692 B2 JP6790692 B2 JP 6790692B2
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- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
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- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- KEDGSDIAPIAOGT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-2-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1OCC1CC KEDGSDIAPIAOGT-UHFFFAOYSA-N 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
これらは、活性エネルギー線で重合し得る樹脂とα,β−不飽和二重結合基を有する単量体とを含有しているが、単量体が溶媒の機能をかねていることから溶剤を必要としないため、塗膜や成型品形成時に溶剤が揮発しないという利点がある。そして、この活性エネルギー線重合性を有する樹脂として、低分子量のポリエステル系樹脂、ポリウレタン系樹脂、ポリエポキシ系樹脂、ポリアクリル系樹脂等の分子末端にα,β−不飽和二重結合基を有するオリゴマーやα,β−不飽和二重結合基を有する単量体等が利用されている。
この光造形法は、従来の切削加工などと比べて、切削困難な複雑な形状にも対応可能、完全自動化プロセスであり取り扱いが容易、製造時間が短くコスト面でも有利などの様々な利点を有しており、樹脂製品の生産の他、デザイン検討、性能試験、広告用等の試作モデルや医療モデルなどの製造に幅広く用いられるようになってきている。
この立体造形法の代表的な例としては、容器に入れた液状の光硬化性樹脂組成物の液面に、所望パターンの重合硬化層が得られるように、光、例えば、活性エネルギー線の一種である紫外線レーザー光を選択的に照射して重合硬化層を得、次に該硬化層の上に液状の光硬化性樹脂組成物を層状に供給し、次いで前記と同様に光を選択的に照射して前記の硬化層と連続した重合硬化層を形成する。この積層操作を繰り返すことにより、最終的に所望の立体造形物を得る方法である。この立体造形法は、製作する造形物の形状が複雑な場合でも、容易にしかも短時間で目的の造形物を得ることができるため注目されている。
さらに、特許文献7には、エチレン系不飽和モノマーや光開始剤との屈折率の差の絶対値が0でない微小中空球を含有する光硬化性液体組成物が開示されており、該光硬化性液体組成物の透明度が減少することが記載されている。さらに、特許文献8には、発色剤を含有する照射硬化性樹脂組成物が開示されており、該照射硬化性樹脂組成物から製造された三次元物品は、硬化の前後で異なる色を示すことが記載されている。
しかしながら、上記樹脂組成物を硬化して得られる樹脂硬化物も、強靭性、耐水性、物性安定性や経時的変形の抑制の全ての要求を満足するには至っていないのが現状である。
分子内に水酸基を有しない、アクリロイル基またはメタクリロイル基含有化合物(B2)とを含有することを特徴とする上記光学的立体造形用活性エネルギー線硬化性樹脂組成物に関する。
なお、本願では、「(メタ)アクリロイル」、「(メタ)アクリル酸」、「(メタ)アクリレート」、及び「(メタ)アクリロイルオキシ」と表記した場合には、特に説明がない限り、それぞれ、「アクリロイル及び/又はメタクリロイル」、「アクリル酸及び/又はメタクリル酸」、「アクリレート及び/又はメタクリレート」、及び「アクリロイルオキシ及び/又はメタクリロイルオキシ」を表すものとする。
ここで、「活性エネルギー線」とは、紫外線、可視光線、赤外線、エレクトロンビーム、及び放射線を含む、化学反応を生じさせるための活性化に必要なエネルギーを提供できる、広義のエネルギー線を意味する。本発明の光学的立体造形用活性エネルギー線硬化性樹脂組成物(以下、「樹脂組成物」と称す)は、上記活性エネルギー線の照射によって、重合反応が進行し、硬化物を形成する。特に限定するものではないが、本発明の一実施形態において、上記活性エネルギー線は、紫外線を含む光エネルギーであることが好ましい。
以下、本発明の樹脂組成物を構成する各成分について詳述する。
まず、本発明の重合体(A)について説明する。本発明の重合体(A)は、ラジカル重合中に酸素分子による重合阻害によって活性が低下したラジカルを再度活性化する機能(連鎖移動)を付与するために用いられ、環状カーボネート基を含んでいれば、その構造が限定されるものではない。
メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、2,2,4−トリメチルシクロヘキシル(メタ)アクリレート、4−t−ブチルシクロヘキシル(メタ)アクリレート、ステアリル(メタ)アクリレート、ラウリル(メタ)アクリレート、イソボルニル(メタ)アクリレート、アダマンチル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、ジシクロぺンテニルオキシエチル(メタ)アクリレート、トリシクロ−[5.2.1.0(2,6)]−デカニル(メタ)アクリレート、トリシクロ−[5.2.1.0(2,6)]−デカニルオキシエチル(メタ)アクリレート等の脂肪族単量体;
フェニル(メタ)アクリレート、ベンジル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、ロジンアクリレート等の芳香族単量体;
本発明において、上記成分(B)は、分子内に少なくとも1個のアクリロイル基またはメタクリロイル基を含有する単量体である。上記成分(B)は、分子内に少なくとも1個の水酸基を有する化合物(B1)と分子内に水酸基を有しない化合物(B2)とに分けられる。
上記化合物(B1)における水酸基は、反応速度の向上や重合硬化収縮の抑制の点で好ましい。水酸基を有することにより分子間での水素結合が働き、樹脂組成物の凝集力や架橋度を向上させることができ、立体造形物としての耐熱性、耐湿熱性、熱的寸法安定性向上に効果を示す。
水酸基を有する化合物(B1)と、水酸基を有しない化合物(B2) の双方が含有されるように適時配合することで、活性エネルギー線照射による重合硬化性、立体造形物の硬化収縮性、及び、耐熱性、耐湿熱性や耐水性等の耐久性の点で良好な、樹脂組成物とすることができる。
分子内に1個以上の水酸基を有する、アクリロイル基またはメタクリロイル基含有化合物(B1)のうち、水酸基を有し、環状構造を有しない化合物(b1)としては、例えば、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸1−ヒドロキシプロピル、(メタ)アクリル酸2−ヒドロキシプロピル、(メタ)アクリル酸3−ヒドロキシプロピル、(メタ)アクリル酸1−ヒドロキシブチル、(メタ)アクリル酸2−ヒドロキシブチル、(メタ)アクリル酸3−ヒドロキシブチル、(メタ)アクリル酸4−ヒドロキシブチル、(メタ)アクリル酸6−ヒドロキシヘキシル、(メタ)アクリル酸8−ヒドロキシオクチル、シクロヘキサンジメタノールモノ(メタ)アクリル酸エステル、(メタ)アクリル酸10−ヒドロキシデシル、(メタ)アクリル酸12−ヒドロキシラウリル、(メタ)アクリル酸エチル−α−(ヒドロキシメチル)、単官能(メタ)アクリル酸グリセロール、あるいは、2−(アクリロイルオキシ)エチル6−ヒドロキシヘキサノネート等の前記水酸基を有する、アクリロイル基またはメタクリロイル基含有化合物に対してε−カプロラクトンラクトンの開環付加により末端に水酸基を有する(メタ)アクリル酸エステルや、前記水酸基含有α,β−エチレン性不飽和二重結合基含有化合物に対してエチレンオキサイド、プロピレンオキサイド、ブチレンオキサイドなどのアルキレンオキサイドを繰り返し付加したアルキレンオキサイド付加(メタ)アクリル酸エステル等の水酸基含有の脂肪族(メタ)アクリル酸エステル類;
化合物(B1)のうち、水酸基を有し、環状構造を有する化合物(b2)は、水酸基と環状構造の双方を有するものであれば、特に制限はなく使用できる。化合物(b2)は、分子内に一つ以上の環構造を有しているため、水酸基を有していても耐熱性や耐湿熱性等の耐久性に加え、耐水性等の面から好ましい。
本発明において化合物(B2)は、分子内に水酸基を有しない、アクリロイル基またはメタクリロイル基含有化合物の単量体であり、樹脂組成物に化合物(B2)を含有することによって、前記化合物(B1)との共重合反応の効率化及び高感度化を図ることが容易であり、活性エネルギー線の照射後に凝集力の高い樹脂硬化物を形成することができる。また、上記樹脂組成物を容易に低粘度化できるとともに、造形時の作業性を向上させることが容易となる。特に限定するものではないが、成分(B2)として使用可能な化合物としては、以下が挙げられる。
本発明の樹脂組成物の一実施形態において、樹脂組成物は、上記必須成分に加えて、カチオン重合性化合物(D)を含んでもよい。カチオン重合性化合物(D)を使用することによって、樹脂組成物を立体造形物として使用した時に、活性エネルギー線照射による異種重合硬化が可能となるため、硬化物が相分離構造を形成し、弾性と応力緩和性やクリープ特性を制御しやすく、適度な弾性や可撓性維持と硬化収縮抑制をより向上させることができる。また、樹脂層の耐熱性又は耐湿熱性を向上させることが容易となる。
エポキシ基含有化合物(d1)としては、例えば、オキシラン、メチルオキシラン、フェニルオキシラン、1,2−ジフェニルオキシラン、メチリデンオキシラン、オキシラニルメチル、オキシラニルメタノール、オキシランカルボン酸、(クロロメチル)オキシラン、(ブロモメチル)オキシラン、オキシラニルアセトニトリル、2,2'−(ジメチルメチレン)ビス[(p−フェニレン)オキシメチレン]ビスオキシラン、2,2'−[メチレンビス(2,1−フェニレンオキシメチレン)]ビスオキシラン等のオキシラン化合物類、あるいは、グリシジルエーテル、グリシジルエステル、グリシジルアミン等のオキシラン環の水素原子がメチレン結合基やメチン結合基が置換されているエポキシ基含有化合物類;
オキセタニル基含有化合物(d2)としては、例えば、3−エチル−3−ヒドロキシメチルオキセタン、1,4−ビス[(3−エチル−3−オキセタニル)メトキシメチル]ベンゼン、ジ(1−エチル−3−オキセタニル)メチルエーテル、3−エチル−3−(フェノキシメチル)オキセタン、3−エチル−3−(2−エチルヘキシロキシメチル)オキセタン、フェノールノボラックオキセタン、3‐エチル−{(3−トリエトキシシリルプロポキシ)メチル}オキセタン等が挙げられる。オキセタニル基含有化合物(d2)は単独で用いてもよいし、2種類以上を併用し用いてもよい。
5員環以上の環状エーテル化合物(d3)としては、例えば、2−メチルテトラヒドロフラン、2,5−ジエトキシテトラヒドロフラン、テトラヒドロフラン−2,2−ジメタノール3−メチル−2,4(3H、5H)−フランジオン、2,4−ジオキソテトラヒドロフラン−3−カルボキシラート、プロパン酸1,5−ジ(テトラヒドロフラン−2−イル)ペンタン−3−イル、4−(2,5−ジオキソテトラヒドロフラン−3−イル)−1,2,3,4−テトラヒドロナフタレン−1,2−ジカルボン酸無水物、メトキシテトラヒドロピラン、2−(プロパジエニルオキシ)テトラヒドロ−2H−ピラン、2−(テトラヒドロフルフリルオキシ)テトラヒドロピラン、N−(2,6−ジオキソテトラヒドロ−2H−ピラン−3−イル)フタルイミド、3−[3−ヒドロキシプロピル]オキシ]オキセパン、(2R,3R)−2−メチル−3−(ベンジルオキシメチル)オキセパン−3−オール、5−クロロ−2−(2−フェニルエチル)オキセパン等が挙げら、単独で用いてもよいし、2種類以上を併用し用いてもよい。
2個以上の酸素又は酸素以外のヘテロ基を有する化合物(d4)としては、環状エステル化合物、環状ホルマール化合物、環状カーボネート化合物、含フッ素環状化合物等がある。環状エステル化合物が、ラクトン類であることが好ましい。環状ホルマール化合物が、ジオキソラン類、ジオキサン類及びトリオキサン類から選択される化合物であることがより好ましい。
工業的には、プロピオラクトン、ブチロラクトン、バレロラクトン、カプロラクトン、1,3−ジオキソラン、1,2−ジオキサン、1,3−ジオキサン、1,4−ジオキサン、1,3,5−トリオキサン、エチレンカーボネート、プロピレンカーボネート、グリセリンカーボネート等が反応性の点で好ましく用いられる。
本発明の樹脂組成物の一実施形態において、樹脂組成物は、上記必須成分に加えて、オリゴマー(E)を含んでもよい。オリゴマー(E)を使用することによって、樹脂組成物を光造形材料として使用した時に、造形性及び硬化収縮性をより向上させることができる。また樹脂層の耐熱性又は耐湿熱性を向上させることが容易となる。
ポリエステル系オリゴマー(e1)としては、主鎖骨格に多塩基酸と多価アルコールを重縮合して得られるポリエステルの末端あるいはポリエステル鎖中の水酸基と(メタ)アクリル酸、マレイン酸などの分子内に1個以上のカルボキシル基を有するα,β−エチレン性不飽和二重結合基含有化合物とのエステル化によって得られる化合物、あるいはポリエステルの末端あるいはポリエステル鎖中のカルボキシル基と(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピルなどの前述の化合物(B1)とのエステル化によって得られる化合物である。その他、酸無水物と(メタ)アクリル酸グリシジルと少なくとも1個の水酸基を有する化合物とから得られるポリエステルオリゴマー等もポリエステルオリゴマー(e1)として使用可能である。
比較的高分子量のポリオール類としては、より具体的には、例えば、高分子量ポリエステルポリオール、高分子量ポリアミドポリオール、高分子量ポリカーボネートポリオール及び高分子量ポリウレタンポリオールが挙げられる。高分子量ポリカーボネートポリオールは、上記の比較的低分子量のジオールと炭酸エステル又はホスゲンとの反応によって得られる。
上記高分子量ポリアミドポリオールの市販品としては、富士化成工業社製のTPAE617等を使用できる。
上記高分子量ポリカーボネートポリオールの市販品としては、例えば、パーストープ社製のオキシマーN112、旭化成ケミカルズ社製のPCDLシリーズ、クラレ社製のクラレポリオールPMHCシリーズ、クラレポリオールCシリーズ等が挙げられる。
その他に、ポリカプロラクトンジオール、ポリ(β−メチル−γ−バレロラクトン)ジオール、ポリバレロラクトンジオール等のラクトン類を開環重合して得られるポリエステルポリオール等も、上記高分子量ポリオールとして使用できる高分子量ポリオールに含まれる。
ポリウレタン系オリゴマー(e2)は、少なくとも1個以上のイソシアネート基を有する化合物と前記化合物(B1)とを反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と上述の多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと前記化合物(B1)とを反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと、更に少なくとも1個以上のアミノ基を有する化合物とを反応させて得られる末端イソシアネート基のウレタンプレポリマーと前記化合物(B1)とを反応させて得られる化合物である。また、イソシアネート基とアミノ基とを反応させて得られるウレア結合基を含有したものもポリウレタン系オリゴマー(e2)に含む。
また、アミノ基を有するアミン類としては、、例えばアミノメタン、アミノエタン、1−アミノプロパン、2−アミノプロパン、1−アミノブタン、2−アミノブタン、1−アミノペンタン、2−アミノペンタン、3−アミノペンタン、イソアミルアミン、1−アミノヘキサン、1−アミノヘプタン、2−アミノヘプタン、2−オクチルアミン、1−アミノノナン、1−アミノデカン、1−アミノドデカン(ラウリルアミン)、1−アミノトリデカン、1−アミノヘキサデカン、1−アミノテトラデデカン(ミリスチルアミン)、1−アミノペンタデカン、セチルアミン、オレイルアミン、ココアルキルアミン、牛脂アルキルアミン、硬化牛脂アルキルアミン、アリルアミン、ステアリルアミン、アミノシクロプロパン、アミノシクロブタン、アミノシクロペンタン、アミノシクロヘキサン、アミノシクロドデカン、1−アミノ−2−エチルヘキサン、1−アミノ−2−メチルプロパン、2−アミノ−2−メチルプロパン、3−アミノ−1−プロペン、3−アミノメチルヘプタン、3−イソプロポキシプロピルアミン、3−ブトキシプロピルアミン、3−イソブトキシプロピルアミン、2−エチルヘキシロキシプロピルアミン、3−デシロキシプロピルアミン、3−ラウリロキシプロピルアミン、3−ミリスチロキシプロピルアミン、2−アミノメチルテトラヒドロフラン、アニリン、o−アミノトルエン、m−アミノトルエン、p−アミノトルエン、o−ベンジルアニリン、p−ベンジルアニリン、1−アニリノナフタレン、1−アミノアントラキノン、2−アミノアントラキノン、1−アミノアントラセン、2−アミノアントラセン、5−アミノイソキノリン、o−アミノジフェニル、4−アミノジフェニルエーテル、2−アミノベンゾフェノン、4−アミノベンゾフェノン、o−アミノアセトフェノン、m−アミノアセトフェノン、p−アミノアセトフェノン、ベンジルアミン、α−フェニルエチルアミン、フェネシルアミン、p−メトキシフェネシルアミン、p−アミノアゾベンゼン、m−アミノフェノール、p−アミノフェノール、アリルアミン等の1級アミン類;
ポリエポキシ系オリゴマー(e3)は、グリシジル基を有する化合物とヒドロキシエチル(メタ)アクリレート、(メタ)アクリル酸、マレイン酸などの分子内に1個以上の水酸基やカルボキシル基を有するα,β−不飽和二重結合基含有化合物との反応により得られる化合物であり、実質的にグリシジル基を有しない、アクリロイル基またはメタクリロイル基含有化合物である。代表例としてビスフェノール型、エポキシ化油型、フェノールノボラック型、脂環型が挙げられる。ビスフェノール型ポリエポキシ系オリゴマーとしては、ビスフェノール類とエピクロルヒドリンとを反応させて得られるビスフェノール型ジグリシジルエーテルと(メタ)アクリル酸などの分子内に1個以上のカルボキシル基を有するα,β−不飽和二重結合基含有化合物とを反応して得られるものである。
本発明では、オリゴマー(E)として、アクリル系オリゴマー(e4)を使用することもできる。使用可能な化合物の具体例として、アクリロイル基またはメタクリロイル基含有変性ポリエーテル、アミン変性されたアクリロイル基またはメタクリロイル基含有化合物、並びに、アルキッド樹脂、スピロアセタール樹脂、ポリブタジエン樹脂、ポリチオールポリエン樹脂及び多価アルコール等の各種化合物にアクリロイル基またはメタクリロイル基を付加させた化合物からなる群より選択される1以上の化合物の、オリゴマーまたはプレポリマーを使用することができる。
本発明の樹脂組成物は、各種活性化エネルギー線の照射によって重合反応が進行し、硬化可能である。しかし、上記樹脂組成物は、必要に応じて活性エネルギー線重合開始剤(F)を含んでもよい。活性エネルギー線重合開始剤(F)を使用することによって、重合反応を促進することができる。本発明の一実施形態において、上記活性化エネルギーは紫外線であることが好ましく、紫外線の照射によって重合反応を進行させる場合、樹脂組成物は、活性エネルギー線重合開始剤(F)を含むことが好ましい。
本発明の樹脂組成物には、シラン化合物(G)を含有することが好ましい。シラン化合物(G)としては、公知のシラン化合物を用いることができ、後述の立体造形物の強度が向上するものであれば特に限定されない。例えば、アルキル系アルコキシシラン、アリール系アルコキシシラン、ビニル系アルコキシシラン、アミノ系アルコキシシラン、エポキシ系アルコキシシラン、ハロゲン系アルコキシシラン、(メタ)アクリロイル系アルコキシシラン、メルカプト系アルコキシシラン、カチオン系アルコキシシラン、イソシアネート系アルコキシシラン等のアルコキシル基を有するアルコキシシラン類、及び/または、珪素原子に水素原子が直接結合して反応性を有する有機シラン類等が挙げられる。より具体的に、例えば、テトラメトキシシラン、テトラエトキシシラン、テトライソプロポキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリイソプロポキシシラン、メチルトリアセトキシシラン、メチルトリス( メトキシエトキシ) シラン、メチルトリス( メトキシプロポキシ)シラン、エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリイソプロポキシシラン、プロピルトリメトキシシラン、プロピルトリエトキシシラン、プロピルトリイソプロポキシシラン、ブチルトリメトキシシラン、ブチルトリエトキシシラン、ヘキシルトリメトキシシラン、ヘキシルトリエトキシシラン、オクチルトリメトキシシラン、オクチルトリエトキシシラン、デシルトリメトキシシラン、デシルトリエトキシシラン、シクロヘキシルトリメトキシシラン、シクロヘキシルトリエトキシシラン、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジイソプロポキシシラン、ジメチルジアセトキシシラン、ジメチルビス(メトキシエトキシ)シラン、ジメチルビス(メトキシプロポキシ)シラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジエチルジイソプロポキシシラン、ジエチルジアセトキシシラン、メチルエチルジメトキシシラン、メチルエチルジエトキシシラン、メチルエチルジイソプロポキシシラン、メチルエチルジアセトキシシラン、メチルプロピルジメトキシシラン、メチルプロピルジエトキシシラン、メチルプロピルジイソプロポキシシラン、メチルプロピルジアセトキシシラン、等のアルキル系アルコキシシラン類;
一方、10質量部を超えると、凝集力が不足して耐熱性や耐湿熱性等の耐久性試験にて重合硬化物に発泡が生じやすく、また、活性エネルギー線で重合硬化した場合には、樹脂硬化物に対する硬度が低下する場合がある。
本発明における樹脂組成物は、更に酸化防止剤を含んでも良い。酸化防止剤(H)を含むことによって、活性エネルギー線重合後の硬化物の経時での着色を抑制することができる。
酸化防止剤としては、例えば、アデカスタブAO−50、アデカスタブAO−80(アデカ社製)などのフェノール系酸化防止剤や、アデカスタブPEP−8(アデカ社製)、IRGAFOS168(BASF社製)などのリン系酸化防止剤、IRGANOX−PS−800FD(BASF社製)などのイオウ系酸化防止剤等の市販品が挙げられるが、これらに限定されるものではない。
酸化防止剤(H)の配合割合は、本発明の樹脂組成物100質量部に対して、0.01〜20質量部であり、0.01〜10質量部であることが好ましい。0.01質量部より少ないと、活性エネルギー線により早期に消費されてしまうため、重合率が下がる場合がある。逆に20質量部より多くなると、重合率は上がるが、硬化物の分子量が低下し、立体造形物としての凝集力が低下するため、耐久性が低下する場合がある。
本発明の樹脂組成物は、上記成分に加えて、色材(J)を含有しても良い。色材(J) を使用することによって、立体造形物とした場合、含有される染料や顔料によって、意匠性だけで無く、熱特性、電気特性、あるいは光学特性等の様々な機能性を付与することが可能となる。
例えば、有機顔料としては、トルイジンレッド、トルイジンマルーン、ハンザエロー、ベンジジンエロー、ピラゾロンレッドなどの不溶性アゾ顔料、
リトールレッド、ヘリオボルドー、ピグメントスカーレット、パーマネントレッド2Bなどの溶性アゾ顔料、
アリザリン、インダントロン、チオインジゴマルーンなどの建染染料からの誘導体、
フタロシアニンブルー、フタロシアニングリーンなどのフタロシアニン系有機顔料、
キナクリドンレッド、キナクリドンマゼンタなどのキナクリドン系有機顔料、
ペリレンレッド、ペリレンスカーレットなどのペリレン系有機顔料、
イソインドリノンエロー、イソインドリノンオレンジなどのイソインドリノン系有機顔料、
ピランスロンレッド、ピランスロンオレンジなどのピランスロン系有機顔料、チオインジゴ系有機顔料、縮合アゾ系有機顔料、ベンズイミダゾロン系有機顔料、
キノフタロンエローなどのキノフタロン系有機顔料、
イソインドリンエローなどのイソインドリン系有機顔料、
その他の顔料として、フラバンスロンエロー、アシルアミドエロー、ニッケルアゾエロー、銅アゾメチンエロー、ペリノンオレンジ、アンスロンオレンジ、ジアンスラキノニルレッド、ジオキサジンバイオレット等の有機顔料類が挙げられる。
これら色素誘導体であれば、特に問題無く使用できる。
分散樹脂は、染料や顔料100質量部に対し、不揮発分換算で10〜60質量部の範囲で使用する事が好ましい。また、重合体(A)、化合物(B)、化合物(D)、あるいはオリゴマー(E)を併用使用する場合には、染料や顔料100質量部に対し、不揮発分換算で100〜800質量部の範囲で使用する事が好ましい。
分散樹脂や重合体(A)、化合物(B)、化合物(D)、あるいはオリゴマー(E)が、この範囲より少ないと分散安定性が低下して、樹脂組成物の分散安定性、保存安定性が悪化する場合がある。一方、この範囲を超えると樹脂組成物の粘度が著しく上昇し、樹脂組成物の保存安定性に悪影響を及ぼす場合があったり、樹脂硬化物の造形不良が発生したり、立体造形物表面へのマイグレーションが発生したりするため、立体造形物の造形性や強度についても低下する場合がある。
このような極性樹脂としては、例えば、ポリビニルアルコール、ポリビニルピロリドン、ポリエチレングリコール、ポリ(メタ)アクリル酸、(メタ)アクリル酸−(メタ)アクリル酸アルキルエステル共重合体、スチレン−マレイン酸共重合体、スチレン−マレイン酸−(メタ)アクリル酸アルキルエステル共重合体、酢酸ビニル−クロトン酸共重合体、酢酸ビニル−(メタ)アクリル酸共重合体、ポリスチレンスルホン酸、ポリスチレンスルホン酸ナトリウム、スチレンスルホン酸−マレイン酸共重合体、ポリイタコン酸等の親水性のビニル系共重合体樹脂;
メチルセルロース、エチルセルロース、プロピルセルロース、エチルメチルセルロース、ヒドロキシアルキルセルロース、ヒドロキシプロピルメチルセルロース、カルボシキメチルスセルロース、アルカリ金属カルボキシメチルセルロース、アルカリ金属セルロース硫酸塩、セルロースグラフト重合体等のセルロース誘導体;
ポリグルタミン酸、ポリアスパラギン酸等のポリペプチド類;
長鎖ポリアミノアマイドと極性酸エステルの塩、長鎖ポリアミノアマイドと高分子量酸エステルの塩、ナフタレンスルホン酸ホルマリン縮合物塩、ステアリルアミンアセテート等のアミドエステル塩;
等が挙げられるが、特にこれらに限定されるものではない。これらは1種類または2種以上を併用して用いることができる。
また、Efka CHEMICALS社製「エフカ44、46、47、48、49、54、63、64、65、66、71、701、764、766」、「エフカポリマー100(変性ポリアクリレート)、150(脂肪族系変性ポリマー)、400、401、402、403、450、451、452、453(変性ポリアクリレート)、745(銅フタロシアニン系)」、共栄社化学社製「フローレン TG−710(ウレタンオリゴマー)、「フローノンSH−290、SP−1000」、「ポリフローNo.50E、No.300(アクリル系共重合物)」、楠本化成社製「ディスパロン KS−860、873SN、874(高分子分散剤)、#2150(脂肪族多価カルボン酸)、#7004(ポリエーテルエステル型)」が挙げられる。
本発明の樹脂組成物は、本発明の効果を損なわない範囲で有れば、前記したような成分の他に各種添加剤(Q)を適宜配合することが可能である。例えば、重合硬化収縮率低減、熱膨張率低減、寸法安定性向上、弾性率向上、粘度調整、熱伝導率向上、強度向上、靭性向上、着色向上等の観点から有機又は無機の充填剤を配合できる。このような充填剤としては、ポリマー、セラミックス、金属、金属酸化物、金属塩等を用いることができ、形状については粒子状、繊維状等特に限定されない。なお、上記ポリマーの配合に当っては、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、消泡剤等、充填剤としてではなくポリマーブレンド、ポリマーアロイとして、光学的立体造形用樹脂組成物中に溶解、半溶解又はミクロ分散させることも可能である。
本発明の樹脂組成物は、上記、重合体(A)、化合物(B)を必須成分とし、更に必要に応じて、化合物(D)、オリゴマー(E)、光重合開始剤(F)、シラン化合物(G)、酸化防止剤(H)、色剤(J)およびその他の各種添加剤(Q)を配合後、均一に混合することによって製造することができる。
なお、本発明における樹脂組成物は、実質的に有機溶剤を含まないことが好ましいが、有機溶剤を含有することも可能である。 例えば、メタノール、エタノール、イソプロピルアルコール、アセトン、メチルエチルケトン、メチルイソブチルケトン、酢酸メチル、酢酸エチル、酢酸ブチル、シクロヘキサン、トルエン、キシレンその他の炭化水素系溶媒等の有機溶剤や、水をさらに添加して、光学的立体造形用樹脂組成物の粘度を調整することもできるし、光学的立体造形用樹脂組成物を加熱して粘度を低下させることもできる。
樹脂組成物の粘度は、化合物(B1)、及び化合物(B2)の粘度で殆ど決定されるため、これらの粘度を1〜100,000mPa・sの範囲で管理することにより、樹脂組成物の粘度も管理が可能である。
本発明の樹脂組成物は、光学的立体造形法における硬化性液状材料として好適に使用される。即ち、この樹脂組成物の特定箇所に、可視光、紫外光、赤外光等の光を選択的に照射して重合硬化に必要な活性エネルギーを供給することにより、所望形状の樹脂硬化物や立体造形物を得ることができる。
活性エネルギー線の照射光源としては、150〜550nm波長域の光を主体としたもので、低圧水銀灯、中圧水銀灯、高圧水銀灯、超高圧水銀灯、ケミカルランプ、ブラックライトランプ、マイクロウェーブ励起水銀灯、LEDランプ、キセノンランプ又はメタルハライドランプなどの他、半導体レーザー光線、電子線なども露光用活性エネルギー線として利用できる。コスト面や指向性、収束性の点で紫外線レーザー光線が好ましい。
活性エネルギー線の照射強度は、0.1〜500mW/cm2であることが好ましい。光照射強度が0.1mW/cm2未満であると、硬化に長時間を必要とし、500mW/cm2を超えると、ランプから輻射される熱により、未硬化の樹脂組成物に劣化が生じる場合がある。照射強度と照射時間の積として表される積算照射量は1〜5,000mJ/cm2とであることが好ましい。積算照射量が1mJ/cm2より少ないと、重合硬化に長時間を必要とし、5,000mJ/cm2より大きいと、照射時間が非常に長くなり、生産性が劣る場合がある。
本発明の樹脂組成物を用いて立体造形物を得る代表的な方法としては、液状である本発明の光学的立体造形用樹脂組成物に、所望のパターンを有する硬化層が得られるように光を選択的に照射して硬化層を形成し、次に該硬化層に隣接する未硬化の組成物層に同様にして光を照射して先に形成された硬化層と連続する新たな硬化層を形成し、この積層操作を繰り返すことにより、最終的に目的とする立体形状の造形物とする方法を挙げることができる。この方法のさらに具体的態様としては、次に例示する方法を挙げることができる。
攪拌機、温度計、還流冷却器、ガス導入管を備えた反応容器にグリセリンカーボネート10部、トリエチルアミン13部、4−メトキシフェノール0.01部、テトラヒドロフラン100部を入れ、容器に乾燥空気を注入しながら、0℃に冷却して、同温度でアクリル酸クロライド12部を1時間かけて滴下した。滴下終了後、NMR測定を行って目的物が生成していることを確認した。室温に冷却後、沈殿物をろ過し、テトラヒドロフランを減圧溜去乾燥することで、環状カーボネート基を含む単量体(a−1)である単量体1を得た。
攪拌機、温度計、還流冷却器、ガス導入管を備えた反応容器にグリセリンカーボネート25部、ジラウリン酸ジブチル錫0.1部を入れ、容器に乾燥空気を注入しながら、60℃に加熱して、同温度で2−イソシアナトエチルアクリレート30部を1時間かけて滴下した。滴下終了後、IR測定を行ってイソシアネート由来のピークが焼失していることを確認した。室温に冷却後、希釈せずに取り出し、環状カーボネート基を含む単量体(a−1)である単量体2を得た。
攪拌機、温度計、滴下装置、還流冷却器、ガス導入管を備えた反応容器にメチルエチルケトン150部を入れ、容器に窒素ガスを注入しながら60℃に加熱して、同温度でメチルメタクリレート90部、単量体1を10部、2,2’−アゾビス(2,4−ジメチルバレロニトリル)2.7部の混合物を2時間かけて滴下して重合反応を行った。滴下終了後、さらに60℃で1時間反応させた後、2,2’−アゾビス(2,4−ジメチルバレロニトリル)0.3部をメチルエチルケトン3部に溶解させたものを添加し、その後3時間、同じ温度で攪拌を続け重合体A−1を得た。GPC測定により、重量平均分子量は18000であった。また、IR測定により、環状カーボネート由来の1810cm-1付近のピークが観測された。
単量体1の代わりに、単量体2を使用した以外は、重合体A−1の製造と同様に重合体A−2を得た。GPC測定により、重量平均分子量は17000であった。また、IR測定により、環状カーボネート由来の1810cm-1付近のピークが観測された。
単量体2を30部、メチルメタクリレートを70部とした以外は、重合体A−2の製造と同様に重合体A−3を得た。GPC測定により、重量平均分子量は16000であった。また、IR測定により、環状カーボネート由来の1810cm-1付近のピークが観測された。
単量体2を5部、メチルメタクリレートを95部とした以外は、重合体A−2の製造と同様に重合体A−4を得た。GPC測定により、重量平均分子量は19000であった。また、IR測定により、環状カーボネート由来の1810cm-1付近のピークが観測された。
攪拌機、温度計、滴下装置、還流冷却器、ガス導入管を備えた反応容器にメチルエチルケトン150部を入れ、容器に窒素ガスを注入しながら60℃に加熱して、同温度でメチルメタクリレート100部、2,2’−アゾビス(2,4−ジメチルバレロニトリル)2.7部の混合物を2時間かけて滴下して重合反応を行った。滴下終了後、さらに60℃で1時間反応させた後、2,2’−アゾビス(2,4−ジメチルバレロニトリル)0.3部をメチルエチルケトン3部に溶解させたものを添加し、その後3時間、同じ温度で攪拌を続けカーボネート基を含まない重合体A−5を得た。GPC測定により、重量平均分子量は20000であった。
[製造例1、2]
化合物(B2)と分散樹脂とを攪拌し、分散樹脂が完全に溶解したことを確認した後、染料、または顔料を投入し、ハイスピードミキサー等で均一になるまで攪拌後、得られたミルベースを横型サンドミルで約2時間分散して製造した。製造した色材(J)の分散体(顔料分散体)の配合(数値は部を表す)を表1に示す。表1において、空欄は、配合なしを意味している。
[実施例1〜35、比較例1〜3]
酸素濃度が10%以下に置換された遮光された300mlのマヨネーズ瓶に、化合物(A)、化合物(B1)および化合物(B2)を必須成分として、さらに必要に応じて、化合物(D)、オリゴマー(E)、活性エネルギー線重合開始剤(F)、シラン化合物(G)、酸化防止剤(H)、色材(J)および各種添加剤(Q)を表2に示す比率で仕込み、攪拌機にて十分に攪拌を行い、十分に脱泡を行うことで、実施例1〜35と比較例1〜3の樹脂組成物を得た。
得られた樹脂組成物について、以下の方法に従って外観および粘度(mPa・s)を求め、結果を表2に示した。
《外観》
樹脂組成物の液体外観を目視にて評価した。
《粘度》
樹脂組成物を23℃の雰囲気下でE型粘度計(東機産業社製 TV−22)にて、約1.2mlを測定用試料とし、回転速度0.5〜100rpm、1分間回転の条件で測定し、溶液粘度(mPa・s)とした。
[実施例36〜70、比較例4〜6]
得られた樹脂組成物について、次の方法で硬化速度、ヤング率、膨潤度、反り、及び表面滑性を測定し、成型試験を行った。結果を表4に示す。
アプリケータを用いて、ガラス板上に樹脂組成物を10μm厚に塗布し、この塗膜にウシオ電気株式会社製の水銀−キセノンランプUXM−200YAの光を405nmの光のみを選択的に透過するバンドパスフィルターおよび光量調節のためのNDフィルターを介して0.1J/cm2照射した。光照射後の膜のタックを触診にて3段階で評価した。評価「×」以外であれば、実際の使用時に特に問題ない。
○:タックなし
△:若干タックがある
×:タックがある
アプリケータを用いてガラス板上に樹脂組成物を250μm厚に塗布し、0.3J/cm2(波長 :405nm)の紫外線を照射して硬化フィルムを得た。次いで、ガラス板上から硬化フィルムを剥離し、23℃、相対湿度50%で24時間状態調節し、試験片とした。測定は23℃、相対湿度50%の恒温湿室内で行った。前記試験片のヤング率を引張り速度1mm/minおよび標線間25mmの条件で測定した。
このヤング率を4段階で評価した。評価「×」以外であれば、実際の使用時に特に問題ない。
◎:120(kg/mm2)以上。全く問題なし。
○:100(kg/mm2)以上〜120(kg/mm2)未満。若干弱いが、問題なし。
△:80(kg/mm2)以上〜100(kg/mm2)未満。実用上、使用可。
×:80(kg/mm2)未満。実用上、問題あり。
光源としてArイオンレーザー(波長 351、385nm)を用いた光造形装置(ソリッドクリエーターJSC−2000:ソニー株式会社製)を使用し、液面でのレーザーパワー40mW、走査速度100cm/minで成形して試験片〔(幅50mm×長さ50mm×高さ1mm):1回の積層厚0.2mm×5回積層〕とした。付着している樹脂液を丁寧に拭き取った後、板の質量W1 を測定した。次いで、該試験片を樹脂液中に25℃で24時間浸漬し、付着した樹脂液を拭き取った後、質量W2 を測定した。
次式により膨潤度を算出し、3段階で評価した。評価「×」以外であれば、実際の使用時に特に問題ない。
膨潤度(%)=〔(W2 −W1 )/W1 〕× 100
○:2(%)未満。全く問題なし。
△:2(%)以上〜5(%)未満。実用上、使用可。
×:5(%)以上。実用上、問題あり。
前述した光造形装置を用いて、液面でのレーザーパワー40mW、走査速度100cm/minで成形して試験片〔(幅50mm×長さ50mm×高さ40mm):1回の積層厚0.2mm×100回積層〕とした。付着した樹脂液を拭き取った後、UVランプを用いてポストキュアーを行った(照射線量:5J/cm2、波長 :365nm)。次いで、試験片の片方を水平な台に固定し、他端の持ち上がり量Δh(mm)で反りの評価を行った。
この反りを4段階で評価した。評価「×」以外であれば、実際の使用時に特に問題ない。
◎:0.2(mm)未満。全く問題なし。
○:0.2(mm)以上〜0.5(mm)未満。若干あるが、問題なし。
△:0.5(mm)以上〜1.0(mm)未満。実用上、使用可。
×:1.0(mm)以上。実用上、問題あり。
アプリケータを用いてガラス板上に樹脂組成物を250μm 厚に塗布し、0.3J/cm2(波長 :405nm)の紫外線を照射してガラス積層硬化フィルムを得、23℃、相対湿度50%で24時間状態調節し、試験片とした。測定23℃、相対湿度50%の恒温湿室内で、前記試験片を#0000のスチールウールにより、硬化フィルムの表面を250g/cm2の荷重をかけながら10回摩擦し、耐擦傷性試験を行った。傷の発生の有無および傷の程度を目視により観察し、表面活性の指標とした。
評価は4段階で行った。評価「×」以外であれば、実際の使用時に特に問題ない。
◎:傷の発生なし。全く問題なし。
○:5本以下の傷が発生する。若干あるが、問題なし。
△:傷が6〜10本発生する。実用上、使用可。
×:傷が無数に発生する。実用上、問題あり。
Claims (6)
- 環状カーボネート基を含む単量体(a−1)と、(a−1)を除く単量体(a−2)とをラジカル重合してなる重合体(A)と、ラジカル重合性化合物(B)とを含有する光学的立体造形用活性エネルギー線硬化性樹脂組成物。
- ラジカル重合性化合物(B)が、分子内に1個以上の水酸基を有する、アクリロイル基またはメタクリロイル基含有化合物(B1)と、
分子内に水酸基を有しない、アクリロイル基またはメタクリロイル基含有化合物(B2)とを含有することを特徴とする請求項1記載の光学的立体造形用活性エネルギー線硬化性樹脂組成物。 - 分子内に1個以上の水酸基を有する、アクリロイル基またはメタクリロイル基含有化合物(B1)が、水酸基を有し、環状構造を有しないアクリロイル基またはメタクリロイル基含有化合物(b1)を含有することを特徴とする請求項2に記載の光学的立体造形用活性エネルギー線硬化性樹脂組成物。
- 分子内に1個以上の水酸基を有する、アクリロイル基またはメタクリロイル基含有化合物(B1)が、水酸基を有し、環状構造を有するアクリロイル基またはメタクリロイル基含有化合物(b2)を含有することを特徴とする請求項2または3に記載の光学的立体造形用活性エネルギー線硬化性樹脂組成物。
- さらに、オリゴマー(E)を含有することを特徴とする請求項1〜4いずれか1項に記載の光学的立体造形用活性エネルギー線硬化性樹脂組成物。
- 光学的立体造形用活性エネルギー線硬化性樹脂組成物全量中、重合体(A)を1〜20質量%含有することを特徴とする請求項1〜5いずれか1項に記載の光学的立体造形用活性エネルギー線硬化性樹脂組成物。
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