JPWO2019146132A1 - 光学的立体造形用組成物、並びに立体造形物、及びその製造方法 - Google Patents
光学的立体造形用組成物、並びに立体造形物、及びその製造方法 Download PDFInfo
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- JPWO2019146132A1 JPWO2019146132A1 JP2019567829A JP2019567829A JPWO2019146132A1 JP WO2019146132 A1 JPWO2019146132 A1 JP WO2019146132A1 JP 2019567829 A JP2019567829 A JP 2019567829A JP 2019567829 A JP2019567829 A JP 2019567829A JP WO2019146132 A1 JPWO2019146132 A1 JP WO2019146132A1
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- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 238000004090 dissolution Methods 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
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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
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- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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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
- C08F263/00—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00
- C08F263/06—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00 on to polymers of esters with polycarboxylic acids
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- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2351/08—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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Abstract
Description
ことができる。
実施例1〜12の及び比較例1〜4の光学的立体造形用組成物を、以下の手順で調整した。表1に示す組成の重量比に従って全ての成分を、撹拌容器に仕込み、20〜40℃で2時間撹拌して液体組成物を得た。この液体組成物を、10ミクロンフイルターバッグ(PO−10−PO3A−503、Xinxiang D.King industry社製)でろ過して異物を除去し、一晩放置後に脱気して透明な液体組成物を得た。なお、調整した光学的立体造形用組成物の各々を数ml取って台の上に配置し、イソプロピルアルコールをかけると、いずれも容易に洗い流すことができた。
・ダイソーダップA:成分(A)のジアリルフタレート系ポリマー、ヨウ素価(g/100g)50〜60、粘度70〜110mPa・s/30℃(50%MEK粘度)、大阪ソーダ社製
・ダイソーダップK:成分(A)のジアリルフタレート系ポリマー、ヨウ素価(g/100g)50〜60、粘度30〜50mPa・s/30℃(50%MEK粘度)、大阪ソーダ社製
・EBECRYL 600:成分(B1)のビスフェノールA系エポキシジアクリレート、粘度3000(60℃)mPa.s、平均分子量500、酸価<1、OH価220mgKOH/g、ダイセル・オルネックス社製
・KAYARAD R−604:成分(B2)のジオキサングリコールジアクリレート、粘度200〜400mPa・s(25℃)、酸価<1.0、日本化薬社製
・アロニックスM−306:成分(B)の他のラジカル重合性化合物のペンタエリスリトールトリ及びテトラアクリレートの混合物(トリ体65〜70%)、粘度400〜650mPa・s/25℃、東亜合成社製
・イルガキュアー907:成分(C)の2−メチル−1−(4−メチルチオフェニル)−2−モルホリノプロパン−1−オン、BASF社製
・カレンズMTNR1:成分(D)の1,3,5−トリス(3−メルカプトブチリルオキシエチル)−1,3,5−トリアジン−2,4,6−(1H,3H,5H)−トリオン、昭和電工社製
・ダイソーダップ100モノマー:成分(E)のイソフタル酸ジアリル、大阪ソーダ社製
・SA−ZE6:成分(F)のポリオキシエチレンポリグリセリンエーテル・(6)アクリル酸付加物、硬化収縮率8.7%、鉛筆硬度H、粘度600/25℃mPa・s、溶解性;水×、メタノール〇、アセトン◎(◎:透明溶解、〇:くすみあり、△:一部分散・沈降、×:不溶)、坂本薬品工業社製
・SA−ZE12:成分(F)のポリオキシエチレンポリグリセリンエーテル・(12)アクリル酸付加物、硬化収縮率7.4%、鉛筆硬度F、粘度1700/25℃mPa・s、溶解性;水△、メタノール◎、アセトン◎(◎:透明溶解、〇:くすみあり、△:一部分散・沈降、×:不溶)、坂本薬品工業社製
光学的立体造形用組成物の硬化時間を評価するために、以下の手順でサンプルを製作した。実施例1の光学的立体造形用組成物を手製のポリエチレン製長方形型(幅約10mm×長さ100mm×、深さ5mm)に1mm液膜になるように流し込み、3kw高圧水銀等(波長365nm、距離1m)で、5秒間、10秒間、15秒間、20秒間、25秒間、30秒間、各々照射し、評価サンプルAを得た。実施例2〜12及び比較例1〜4の光学的立体造形用組成物についても、同様にして評価サンプルAを得た。
光学的立体造形用組成物の硬化時間を評価するために、以下の手順でサンプルを製作した。実施例1の光学的立体造形用組成物を手製のポリエチレン製長方形型(幅約10mm×長さ100mm×、深さ5mm)に1mm液膜になるように流し込み、3kw高圧水銀灯(波長365nm、距離1m)で20秒間照射し、これを合計4回繰り返して厚さ約4mmの平面板(幅約10mm×長さ100mm)を作成した。さらに平面板を30分間再照射し、光学的立体造形物である評価サンプルBを得た。実施例2〜12及び比較例1〜4の光学的立体造形用組成物についても、同様にして評価サンプルBを得た。
1.光学的立体造形用組成物の硬化時間の評価
評価サンプルAを用いて、照謝時間の短いサンプルからその表面状態を観察し、表面のタックが無い評価サンプルAに係る照射時間を硬化時間とした。なお、「表面のタックの有無」は、評価サンプルAをオーブンに入れて35℃で30分間処理し、室温(25℃)まで冷却した後、評価サンプルAの表面にポリエステルフイルムを手で押し当て、ポリエステルフイルムが簡単に剥がれなければタック有りとし、剥がれればタック無しとして判断した。評価サンプルAの硬化時間を表2に示した。
評価サンプルBを用いて、平面板の層(側面)を日本電子JSM−5600型走査電子顕微鏡(加速電圧7kv、倍率200倍)で観察した。評価の基準は、層間の隙間が存在する場合は(「×」)、層間の隙間がない場合は(「〇」)、とした。結果を表2に示した。
評価サンプルBの平面板を平台に置いて、その端部が平台から浮いた距離を測定する。判定の基準は、浮いた距離2mm以上の場合は(「×」)、浮いた距離2mm以下で浮いている場合は(「△」)、浮いた距離0mmつまり浮いていない場合は(「〇」)、とした。結果を表2に示した。
評価サンプルBの平面板について、ISO527−1に準拠して、以下の測定条件で引張り強度及び伸度を測定した。伸度は、破断時の最大の伸び率として測定した。結果を表2に示した。
測定装置 : インストロン社製3366型万能試験機
引張速度(クロスヘッド速度) : 5mm/分
測定環境 : 温度25℃、湿度45%RH
標点間距離 : 80mm
評価サンプルBの平面板の3点曲げ試験を、ISO527−1に準拠して、以下の測定条件で行い、曲げ強度及び曲げ弾性率を測定した。結果を表2に示した。
測定装置 : インストロン社製3366型万能試験機
試験条件 : 3点曲げ試験治具 圧子半径5mm
支点間距離 64mm
負荷速度(クロスヘッド速度)2mm/分
測定環境 : 温度25℃、湿度45%RH
評価サンプルBについて、以下の測定条件で裸落下試験を行い、割れの有無を目視で観察し、落下割れ観察をした。結果を表2に示した。
落下床面 : 大理石床タイル
落下高さ : 3m
サンプルの重さ : 14.5g
サンプルの落下角度 : 大理石床タイル面に対して60度
判定の基準は、サンプル5つを落下させて、ヒビを含めた割れサンプル個数を記録した。
評価サンプルBの端部10mmを万力で挟んで固定した。評価サンプルBの片方の端部をペンチで挟み、往復10回左右に折り曲げた。試験後、折り曲げた部位の外観を目視で観察する。判定の基準は、〇:変化なし、△:白く変色、▲:ひび割れ、×:割れた、とした。
Claims (6)
- (A)ジアリルフタレート系ポリマーと、
(B)メタクリル基及び/又はアクリル基を有するラジカル重合性化合物と、
(C)ラジカル重合開始剤と、
(D)増感剤と
を含む光学的立体造形用組成物であって、
前記(B)のメタクリル基及び/又はアクリル基を有するラジカル重合性化合物として、
(B1)メタクリル基及び/若しくはアクリル基を有するエポキシ(メタ)アクリレートのラジカル重合性化合物、及び/又は
(B2)メタクリル基及び/若しくはアクリル基を有するジオキサン(メタ)アクリレートのラジカル重合性化合物
を少なくとも含み、
前記(A)のジアリルフタレート系ポリマーを0.5〜10質量%、
前記(B1)及び前記(B2)のラジカル重合性化合物を合計で5〜43質量%、
前記(B)のラジカル重合性化合物のうち、前記(B1)及び前記(B2)以外のラジカル重合性化合物を20〜95質量%、
前記(C)のラジカル重合開始剤を0.1〜5質量%、及び、
前記(D)の増感剤を0.1〜5質量%を含有する、光学的立体造形用組成物。 - さらに、(E)ジアリルフタレート系ポリマーではないアリル基を有する化合物を0.125〜2.5質量%含有する、請求項1に記載の光学的立体造形用組成物。
- 前記(A)のジアリルフタレート系ポリマーが、ジアリルオルソフタレートポリマー又はジアリルイソフタレートポリマーである、請求項1又は2に記載の光学的立体造形用組成物。
- 請求項1〜4のいずれか一項に記載の光学的立体造形用組成物に、活性エネルギー線を照射して硬化させる工程を含む、光学的立体造形物の製造方法。
- 請求項1〜4のいずれか一項に記載の光学的立体造形用組成物の硬化物を含む光学的立体造形物。
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Application Number | Priority Date | Filing Date | Title |
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JP2018011658 | 2018-01-26 | ||
JP2018011658 | 2018-01-26 | ||
PCT/JP2018/013222 WO2019146132A1 (ja) | 2018-01-26 | 2018-03-29 | 光学的立体造形用組成物、並びに立体造形物、及びその製造方法 |
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JP7279942B2 (ja) | 2023-05-23 |
EP3744740A4 (en) | 2021-10-20 |
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