JP4865190B2 - オキセタン化合物を含有するステレオリソグラフィー用樹脂 - Google Patents
オキセタン化合物を含有するステレオリソグラフィー用樹脂 Download PDFInfo
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- JP4865190B2 JP4865190B2 JP2004005735A JP2004005735A JP4865190B2 JP 4865190 B2 JP4865190 B2 JP 4865190B2 JP 2004005735 A JP2004005735 A JP 2004005735A JP 2004005735 A JP2004005735 A JP 2004005735A JP 4865190 B2 JP4865190 B2 JP 4865190B2
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 7
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 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 description 3
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
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- XVKKIGYVKWTOKG-UHFFFAOYSA-N diphenylphosphoryl(phenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 XVKKIGYVKWTOKG-UHFFFAOYSA-N 0.000 description 1
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- 239000010459 dolomite Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
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- 239000003063 flame retardant Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HXYCHJFUBNTKQR-UHFFFAOYSA-N heptane-1,2,3-triol Chemical compound CCCCC(O)C(O)CO HXYCHJFUBNTKQR-UHFFFAOYSA-N 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- XYXCXCJKZRDVPU-UHFFFAOYSA-N hexane-1,2,3-triol Chemical compound CCCC(O)C(O)CO XYXCXCJKZRDVPU-UHFFFAOYSA-N 0.000 description 1
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000001812 iodosyl group Chemical group O=I[*] 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
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- 239000012669 liquid formulation Substances 0.000 description 1
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- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007984 tetrahydrofuranes Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004901 trioxanes Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0037—Production of three-dimensional images
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Description
(A) 少なくとも一種類のカチオン重合性有機物質、
(B) 少なくとも一種類のフリーラジカル重合性有機物質、
(C) 少なくとも一種類のカチオン重合開始剤、
(D) 少なくとも一種類のフリーラジカル重合開始剤、
(E) 少なくとも一種類のヒドロキシル官能性化合物、および
(F) 少なくとも一種類のヒドロキシル官能性オキセタン化合物、
を有してなる組成物に関する。
(1) ある表面に放射線硬化性組成物の薄層を被覆する工程、
(2) 薄層を画像様に化学線に露光して、画像断面を形成する工程であって、化学線が、露光された区域において薄層を実質的に硬化させるのに十分な強度のものである工程、
(3) 先に露光された画像断面上に組成物の薄層を被覆する工程、
(4) 工程(3)からの薄層を画像様に化学線に露出して、追加の画像断面を形成する工程であって、化学線が、露光された区域において薄層を実質的に硬化させ、かつ先に露光された画像断面に付着させるのに十分な強度のものである工程、
(5) 三次元物品を構築するために、十分な回数だけ工程(3)および(4)を繰り返す工程、
を有してなり、
放射線硬化性組成物が上述したものである方法に関する。
カチオン重合性化合物は、脂肪族、脂環式または芳香族ポリグリシジル化合物、もしくは脂環式ポリエポキシドもしくはエポキシクレゾールノボラックもしくはエポキシフェノールノボラック化合物であってよく、平均で、分子中に1より多いエポキシド基(オキシラン環)を持つ。そのような樹脂は、脂肪族、芳香族、脂環式、芳香脂肪族または複素環構造を有していてもよく、それら樹脂はエポキシド基または側基を含有する、またはこれらの基が脂環または複素環系の一部を形成する。これらのタイプのエポキシ樹脂は、一般的な用語として知られており、市販されている。
フリーラジカル硬化性成分は、少なくとも一種類の固体または液体のポリ(メタ)アクリレートを含む、例えば、二、三、四または五官能モノマーまたはオリゴマー脂肪族、脂環式または芳香族アクリレートまたはメタクリレートであることが好ましい。これらの化合物は200から500の分子量を有することが好ましい。
本発明による組成物において、化学線への露光の際に、エポキシ材料の反応を開始させるカチオンを形成するどのようなタイプの光開始剤を用いても差し支えない。公知であり、技術的に実証されたエポキシ樹脂のための適切なカチオン光開始剤は数多くある。これら光開始剤は、例えば、求核性の弱いアニオンを持つオニウム塩を含む。それらの例としては、欧州特許出願公開第153904号明細書に記載されているものなどのハロニウム塩、ヨードシル塩またはスルホニウム塩;例えば、欧州特許出願公開第35969号、同第44274号、同第54509号、および同第164314号の各明細書に記載されたものなどのスルホキソニウム塩;または例えば、米国特許第3708296号および同第5002856号の各明細書に記載されたものなどのジアゾニウム塩が挙げられる。他のカチオン光開始剤は、例えば、欧州特許出願公開第94914号および同第94915号の各明細書に記載されたものなどのメタロセン塩である。他の好ましいカチオン光開始剤が、特許文献3(シュタインマン(Steinmann)等)、4(パン(Pang)等)および10(メリサリス(Melisaris)等)に述べられている。
本発明による組成物において、適切な照射が行われたときにフリーラジカルを形成するどのようなタイプの光開始剤を用いても差し支えない。公知の光開始剤の一般的な化合物としては、ベンゾインなどのベンゾイン類;ベンゾインメチルエーテル、ベンゾインエチルエーテル、およびベンゾインイソプロピルエーテルなどのベンゾインエーテル類;ベンゾインアセテート;アセトフェノン、2,2−ジメトキシアセトフェノン、4−(フェニルチオ)アセトフェノン、および1,1−ジクロロアセトフェノンなどのアセトフェノン類;ベンジル;ベンジルジメチルケタール、およびベンジルジエチルケタールなどのベンジルケタール類;2−メチルアントラキノン、2−エチルアントラキノン、2−tert−ブチルアントラキノン、1−クロロアントラキノン、および2−アミルアントラキノンなどのアントラキノン類;トリフェニルホスフィン;例えば、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(Lucirin(登録商標)TPO)などのベンゾイルホスフィンオキシド類;ベンゾフェノン、および4,4’−ビス(N,N’−ジメチルアミノ)ベンゾフェノンなどのベンゾフェノン類;トリオキサン類およびキサントン類;アクリジン誘導体;フェナゼン誘導体;キノキサリン誘導体または1−フェニル−1,2−プロパンジオン−2−O−ベンゾイルオキシム;1−ヒドロキシシクロヘキシルフェニルケトン、フェニル(1−ヒドロキシイソプロピル)ケトンおよび4−イソプロピルフェニル(1−ヒドロキシイソプロピル)ケトンなどの1−ヒドロキシフェニルケトンまたは1−アミノフェニルケトン;または例えば、4’−メチルチオフェニル−1−ジ(トリクロロメチル)−3,5S−トリアジン、S−トリアジン−2−(スチルベン)−4,6−ビス−トリクロロメチル、およびパラメトキシスチリルトリアジンなどのトリアジン化合物が挙げられ、これらの全ては公知の化合物である。
ヒドロキシル官能性化合物は、少なくとも1つ、好ましくは、少なくとも2つのヒドロキシル官能価を持つどのような有機材料であってもよい。この材料は、残りの成分中に可溶性であるかまたは分散性である固体または液体であってよい。この材料は、硬化反応を阻害する、もしくは熱的または光分解的に不安定であるどのような基も実質的に含まないべきである。
少なくとも1つのオキセタン環および少なくとも1つのヒドロキシル官能価を有するどのような化合物(ここでは、ヒドロキシル官能性オキセタン化合物と称する)を本発明の放射線硬化性組成物の成分(F)として用いてもよい。これらのヒドロキシル官能性オキセタン化合物は1つまたは2つのオキセタン環を有することが好ましい。そのようなヒドロキシル官能性オキセタン化合物の例が、両方ともここに全てを引用する、米国特許第5674922号および同第5981616号の各明細書に開示されている。好ましいヒドロキシル官能性オキセタン化合物は3−エチル−3−ヒドロキシメチル−オキセタンである。
必要であれば、本発明によるステレオリソグラフィー用途の樹脂組成物は、本発明の効果に悪影響が及ぼされない限りは、適量で他の材料を含有してもよい。そのような材料の例としては、上述したカチオン重合性有機物質以外のラジカル重合性有機化合物、感熱性重合開始剤、顔料や染料等の着色剤などの様々な樹脂用添加剤、消泡剤、均展剤、増粘剤、難燃剤および酸化防止剤が挙げられる。
新規の組成物は、例えば、個々の成分を予混し、次いで、これらの予混物を混合することにより、または光のない状態で、所望であれば、わずかに高温で、撹拌容器などの一般的な装置を用いて、全ての成分を混合することにより、公知の様式で調製することができる。
(A) 1つまたは2つのエポキシ基を持つ脂環式エポキシド、
(B) 少なくとも一種類の三、四または五官能モノマーまたはオリゴマーの脂肪族、脂環式または芳香族(メタ)アクリレート、
(C) 少なくとも一種類のカチオン重合開始剤、
(D) 少なくとも一種類のフリーラジカル重合開始剤、
(E) 少なくとも一種類のエトキシル化またはプロポキシル化ヒドロキシル官能性ポリエーテル、および
(F) 少なくとも一種類のヒドロキシル官能性オキセタン化合物、
を有してなる。
(A) 3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート、
(B) ジペンタエリトリトール−モノヒドロキシペンタアクリレート、
(C) 少なくとも一種類のカチオン重合開始剤、
(D) 少なくとも一種類のフリーラジカル重合開始剤、
(E) グリセリンプロポキシル化ポリエーテルジオール、および
(F) 3−エチル−3−ヒドロキシメチル−オキセタン、
を有してなる。
上述した新規の組成物は、化学線の照射によって、例えば、電子ビーム、X線、紫外線または可視光により、好ましくは、280〜650nmの波長範囲の照射線により、重合させることができる。HeCd、アルゴンまたは窒素並びに金属蒸気およびNdYAGレーザのレーザビームが特に適している。本発明は、既存のまたはステレオリソグラフィープロセスに使用すべく開発中の様々なタイプのレーザ、例えば、固体レーザ、アルゴンイオンレーザ、ヘリウムカドミウムレーザ等の全てに拡張される。当業者は、選択された各々の光源について、適切な光開始剤を選択し、適当であれば、増感を行う必要があることを承知している。重合すべき組成物中への放射線の貫通深さおよび動作速度が、吸収係数および光開始剤の濃度に正比例していることが認識されている。ステレオリソグラフィーにおいて、最高数のフリーラジカルまたはカチオン粒子を発生させ、重合すべき組成物中への放射線の貫通深さを最高にできる光開始剤を使用することが好ましい。
各々の配合物の粘度は、ブルックフィールド型粘度計を用いて30℃で測定した。
Claims (2)
- ステレオリソグラフィーによる三次元物品の製造に有用な液体の放射線硬化性組成物であって、
(A) 3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート、
(B) ジペンタエリトリトールモノヒドロキシペンタアクリレート、
(C) トリアリールスルホニウムヘキサフルオロアンチモネート、
(D) 1−ヒドロキシシクロヘキシルフェニルケトン、
(E) 450の平均分子量を有するグリセリンプロポキシル化ポリエーテルトリオール、および
(F) 3−エチル−3−ヒドロキシメチル−オキセタン、
を有してなる組成物。 - ステレオリソグラフィーによる三次元物品の製造に有用な液体の放射線硬化性組成物であって、該放射線硬化性組成物の総重量に基づいて、
(A) 30から70重量%の3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート、
(B) 5から20重量%のジペンタエリトリトールモノヒドロキシペンタアクリレート、
(C) 0.02から5重量%のトリアリールスルホニウムヘキサフルオロアンチモネート、
(D) 0.01から4重量%の1−ヒドロキシシクロヘキシルフェニルケトン、
(E) 5から18重量%の、450の平均分子量を有するグリセリンプロポキシル化ポリエーテルトリオール、および
(F) 9から17重量%の3−エチル−3−ヒドロキシメチル−オキセタン、
を有してなる組成物。
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Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040077745A1 (en) * | 2002-10-18 | 2004-04-22 | Jigeng Xu | Curable compositions and rapid prototyping process using the same |
WO2004113396A1 (ja) * | 2003-06-25 | 2004-12-29 | Cmet Inc. | 安定性の向上した活性エネルギー線硬化性の光学的立体造形用樹脂組成物 |
EP1680713B1 (en) * | 2003-11-06 | 2015-09-23 | DSM IP Assets B.V. | Curable compositions and rapid prototyping process using the same |
JP4874116B2 (ja) * | 2003-11-06 | 2012-02-15 | ハンツマン・アドヴァンスト・マテリアルズ・(スイッツランド)・ゲーエムベーハー | 高い透明性と改良された機械的性質とを有する硬化物品を製造するための光硬化性組成物 |
US20050101684A1 (en) * | 2003-11-06 | 2005-05-12 | Xiaorong You | Curable compositions and rapid prototyping process using the same |
CN1886438A (zh) * | 2003-12-02 | 2006-12-27 | 帝斯曼知识产权资产管理有限公司 | 阻燃可辐射固化组合物 |
JP4620380B2 (ja) * | 2004-05-26 | 2011-01-26 | Jsr株式会社 | 光学的立体造形用放射線硬化性液状樹脂組成物及びそれを光硬化させて得られる光造形物 |
US20060172230A1 (en) | 2005-02-02 | 2006-08-03 | Dsm Ip Assets B.V. | Method and composition for reducing waste in photo-imaging applications |
JP4744200B2 (ja) * | 2005-06-20 | 2011-08-10 | シーメット株式会社 | 平滑化した造形端面を有する立体造形物 |
WO2007008828A2 (en) * | 2005-07-08 | 2007-01-18 | Sky+, Ltd. | Method for casting reactive metals and casting containers associated therewith |
WO2007037434A1 (ja) | 2005-09-29 | 2007-04-05 | Cmet Inc. | 光学的立体造形用樹脂組成物 |
JP5167496B2 (ja) * | 2006-05-01 | 2013-03-21 | ディーエスエム アイピー アセッツ ビー.ブイ. | 放射線硬化性樹脂組成物およびそれを使用した急速三次元的画像形成方法 |
US20080103226A1 (en) * | 2006-10-31 | 2008-05-01 | Dsm Ip Assets B.V. | Photo-curable resin composition |
KR20100014901A (ko) * | 2007-03-14 | 2010-02-11 | 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 | Abs-유사 물품을 제조하기 위한 광경화성 조성물 |
JP5205018B2 (ja) * | 2007-09-06 | 2013-06-05 | シーメット株式会社 | 光学的立体造形用樹脂組成物 |
BRPI0923627A2 (pt) | 2008-12-22 | 2016-01-19 | Nl Organisate Voor Toegepast Natuurwetenchappelijk Onderzoek Tno | método e sistema para produção em camadas de um objeto tangível |
US8678805B2 (en) | 2008-12-22 | 2014-03-25 | Dsm Ip Assets Bv | System and method for layerwise production of a tangible object |
US8777602B2 (en) | 2008-12-22 | 2014-07-15 | Nederlandse Organisatie Voor Tobgepast-Natuurwetenschappelijk Onderzoek TNO | Method and apparatus for layerwise production of a 3D object |
EP2406318B1 (en) | 2009-03-13 | 2021-04-21 | DSM IP Assets B.V. | Radiation curable resin composition and rapid three-dimensional imaging process using the same |
TWI427113B (zh) * | 2009-06-12 | 2014-02-21 | Digitaloptics Corp East | 可硬化樹脂及由其製造之物件 |
EP2502728B1 (en) | 2011-03-23 | 2017-01-04 | DSM IP Assets B.V. | Lightweight and high strength three-dimensional articles producible by additive fabrication processes |
CN104345562B (zh) | 2013-08-09 | 2020-04-24 | 帝斯曼知识产权资产管理有限公司 | 用于增材制造的低粘度液体辐射可固化的牙对准器模具树脂组合物 |
US9650526B2 (en) * | 2014-09-09 | 2017-05-16 | 3D Systems, Inc. | Method of printing a three-dimensional article |
KR102187131B1 (ko) | 2014-10-15 | 2020-12-04 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 수지 조성물 |
KR20160046095A (ko) | 2014-10-20 | 2016-04-28 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 수지 조성물 |
KR20160046094A (ko) | 2014-10-20 | 2016-04-28 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 및 열경화성 수지 조성물 |
TWI519560B (zh) | 2014-11-24 | 2016-02-01 | 財團法人工業技術研究院 | 含氧雜環丁烷基與環氧基之樹脂與樹脂組成物 |
KR20160071725A (ko) | 2014-12-12 | 2016-06-22 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 수지 조성물 |
KR20160071724A (ko) | 2014-12-12 | 2016-06-22 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 수지 조성물 |
KR20160073002A (ko) | 2014-12-16 | 2016-06-24 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 수지 조성물 |
KR20160111760A (ko) | 2015-03-17 | 2016-09-27 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 수지 조성물 |
KR20160112369A (ko) | 2015-03-19 | 2016-09-28 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 수지 조성물 |
KR102195639B1 (ko) | 2015-03-25 | 2020-12-28 | 동우 화인켐 주식회사 | 입체 조형용 광경화성 수지 조성물 |
WO2019157473A1 (en) * | 2018-02-09 | 2019-08-15 | Pressing Developments, L.L.C. | Stainable laminate products, compositions, and methods of manufacture |
ES2685280B2 (es) * | 2017-03-31 | 2019-06-21 | Centro Tecnologico De Nanomateriales Avanzados S L | Composición de resina curable por radiación y procedimiento para su obtención |
JP2019056044A (ja) * | 2017-09-20 | 2019-04-11 | 富士ゼロックス株式会社 | 造形物製造用インク組成物、造形物製造用インク組成物を製造する方法、造形物および造形物製造装置 |
TWI692502B (zh) | 2017-12-29 | 2020-05-01 | 法商阿科瑪法國公司 | 可固化組成物 |
WO2021247419A1 (en) * | 2020-06-02 | 2021-12-09 | Blue Cube Ip Llc | Photo-curable resin composition for use in stereolithography |
IT202000014725A1 (it) * | 2020-06-19 | 2021-12-19 | Mat3D S R L | Composizione di resine foto-polimerizzabili, metodo di fabbricazione di un manufatto impiegante la stessa e manufatto cosi’ ottenuto |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3708296A (en) * | 1968-08-20 | 1973-01-02 | American Can Co | Photopolymerization of epoxy monomers |
US4694029A (en) * | 1985-04-09 | 1987-09-15 | Cook Paint And Varnish Company | Hybrid photocure system |
US4772541A (en) * | 1985-11-20 | 1988-09-20 | The Mead Corporation | Photohardenable compositions containing a dye borate complex and photosensitive materials employing the same |
US4772530A (en) * | 1986-05-06 | 1988-09-20 | The Mead Corporation | Photosensitive materials containing ionic dye compounds as initiators |
US4804575A (en) * | 1987-01-14 | 1989-02-14 | Kollmorgen Corporation | Multilayer printed wiring boards |
US4751102A (en) * | 1987-07-27 | 1988-06-14 | The Mead Corporation | Radiation-curable ink and coating compositions containing ionic dye compounds as initiators |
US5434196A (en) * | 1988-02-19 | 1995-07-18 | Asahi Denka Kogyo K.K. | Resin composition for optical molding |
US5002856A (en) * | 1989-08-02 | 1991-03-26 | E. I. Du Pont De Nemours And Company | Thermally stable carbazole diazonium salts as sources of photo-initiated strong acid |
ES2150977T3 (es) * | 1993-08-09 | 2000-12-16 | Vantico Ag | Nuevos (met)acrilatos conteniendo grupos uretano. |
US5418112A (en) * | 1993-11-10 | 1995-05-23 | W. R. Grace & Co.-Conn. | Photosensitive compositions useful in three-dimensional part-building and having improved photospeed |
JP3161583B2 (ja) * | 1995-07-21 | 2001-04-25 | 東亞合成株式会社 | 活性エネルギー線硬化型組成物 |
KR100491736B1 (ko) * | 1996-07-29 | 2005-09-09 | 반티코 아게 | 입체리토그래피용방사선-경화성액체조성물 |
JP3786480B2 (ja) * | 1996-10-14 | 2006-06-14 | Jsr株式会社 | 光硬化性樹脂組成物 |
JP3765896B2 (ja) * | 1996-12-13 | 2006-04-12 | Jsr株式会社 | 光学的立体造形用光硬化性樹脂組成物 |
US5897961A (en) * | 1997-05-07 | 1999-04-27 | Xerox Corporation | Coated photographic papers |
JP4204113B2 (ja) * | 1997-12-04 | 2009-01-07 | 株式会社Adeka | 新規な芳香族スルホニウム化合物、これからなる光酸発生剤およびこれを含む光重合性組成物、光造形用樹脂組成物ならびに光学的立体造形法 |
JP3913350B2 (ja) * | 1998-01-13 | 2007-05-09 | ナブテスコ株式会社 | 光学的造形用樹脂組成物 |
US6287745B1 (en) * | 1998-02-18 | 2001-09-11 | Dsm N.V. | Photocurable liquid resin composition comprising an epoxy-branched alicyclic compound |
US6136497A (en) * | 1998-03-30 | 2000-10-24 | Vantico, Inc. | Liquid, radiation-curable composition, especially for producing flexible cured articles by stereolithography |
US6100007A (en) * | 1998-04-06 | 2000-08-08 | Ciba Specialty Chemicals Corp. | Liquid radiation-curable composition especially for producing cured articles by stereolithography having high heat deflection temperatures |
US6287748B1 (en) * | 1998-07-10 | 2001-09-11 | Dsm N.V. | Solid imaging compositions for preparing polyethylene-like articles |
US6379866B2 (en) * | 2000-03-31 | 2002-04-30 | Dsm Desotech Inc | Solid imaging compositions for preparing polypropylene-like articles |
US6232361B1 (en) * | 1998-12-11 | 2001-05-15 | Sun Chemical Corporation | Radiation curable water based cationic inks and coatings |
JP4350832B2 (ja) * | 1999-04-19 | 2009-10-21 | Jsr株式会社 | 立体造形用光硬化性樹脂組成物およびこれを硬化してなる造形物 |
US20030149124A1 (en) * | 2001-11-27 | 2003-08-07 | Thommes Glen A. | Radiation curable resin composition for making colored three dimensional objects |
CN101706639A (zh) * | 2002-05-03 | 2010-05-12 | Dsmip财产有限公司 | 可辐射固化树脂组合物及利用该组合物的快速成型方法 |
US20040077745A1 (en) * | 2002-10-18 | 2004-04-22 | Jigeng Xu | Curable compositions and rapid prototyping process using the same |
KR101171253B1 (ko) * | 2003-12-24 | 2012-08-06 | 신이치로 이소베 | 생체분자의 검출방법 및 이에 사용하는 표지색소와표지키트 |
-
2003
- 2003-01-13 US US10/342,408 patent/US20040137368A1/en not_active Abandoned
-
2004
- 2004-01-08 EP EP20040250064 patent/EP1437624A1/en not_active Withdrawn
- 2004-01-13 JP JP2004005735A patent/JP4865190B2/ja not_active Expired - Lifetime
-
2009
- 2009-06-08 US US12/480,146 patent/US20090239175A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
US20040137368A1 (en) | 2004-07-15 |
JP2004217934A (ja) | 2004-08-05 |
US20090239175A1 (en) | 2009-09-24 |
EP1437624A1 (en) | 2004-07-14 |
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