KR950005820A - 우레탄기를 함유하는 (메트)아클릴레이트 - Google Patents

우레탄기를 함유하는 (메트)아클릴레이트 Download PDF

Info

Publication number
KR950005820A
KR950005820A KR1019940019698A KR19940019698A KR950005820A KR 950005820 A KR950005820 A KR 950005820A KR 1019940019698 A KR1019940019698 A KR 1019940019698A KR 19940019698 A KR19940019698 A KR 19940019698A KR 950005820 A KR950005820 A KR 950005820A
Authority
KR
South Korea
Prior art keywords
meth
acrylate
group
weight
urethane group
Prior art date
Application number
KR1019940019698A
Other languages
English (en)
Other versions
KR100355949B1 (ko
Inventor
쉬타인만 베티나
볼프 장-피에르
슐테스 아드리안
훈지커 막스
Original Assignee
에른스트 알테르
시바-가이기 아게
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 에른스트 알테르, 시바-가이기 아게 filed Critical 에른스트 알테르
Publication of KR950005820A publication Critical patent/KR950005820A/ko
Application granted granted Critical
Publication of KR100355949B1 publication Critical patent/KR100355949B1/ko

Links

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
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/34—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/36—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/38—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1065—Esters of polycondensation macromers of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/675—Low-molecular-weight compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1494—Polycondensates modified by chemical after-treatment followed by a further chemical treatment thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Paints Or Removers (AREA)
  • Epoxy Compounds (AREA)
  • Epoxy Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Pyrrole Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

우레탄기 및 동일한 한 분자내에 기타 종합성기도 포함하는 신규(메트)아크릴레이트는 자유 라디칼 및/또는 양이온적으로 중합될 수 있으며 피복물, 접착제, 포토레지스트, 땜납 마스크 제조용으로 또는 스테레오리소그래피에서 사용될 수 있다. 이로부터 제조된 성형물은 응집성의 균일한 망상구조를 가지며 고도의 강도 특성, 특히 기계적 특성을 갖는다.

Description

우레탄기를 함유하는 (메트)아클릴레이트
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. 우레탄기를 함유하는 하기식(Ⅰ)의 (메트)아크릴레이트:
    상기식에서,R1은 양이온적으로 중합가능한 기 또는 자유 라디칼-중합가능한 기이나, 아크릴레이트 및 알릴기는 제외되며, R2는 지방족, 지환족 또는 방향족 라디칼이고, R3는 수소 또는 CH3이며, R3는 디글리시딜 라디칼 제거 후의 지방족, 지환족 또는 방향족 디글리시딜 화합물의 라디칼이거나, 또는 지환족 디에폭시드의 라디칼이고, R5는 지환족 브릿지이다.
  2. 제 1항에 있어서, R1이 양이온적으로 중합가능한 하기식(A)의 기 또는 자유 라디칼-중합가능한 하기식의 기(B)인 우레탄기 함유 일반식(Ⅰ)의 (메트) 아크릴레이트 : -(CH2)x-O-CH=CH2,
    상기식에서, x는 2내지 20의 정수이고 y는 1내지 20의 정수이다.
  3. 제 2항에 있어서, R1이 양이온적으로 중합가능한 기인 우레탄기 함유(메트)아크릴레이트.
  4. 제 1항에 있어서, R2및 R4가, 각각 독립적으로, 1이상의 에테르, 에스테르, 우레탄, 아미드 또는 아릴렌기가 중간에 결합될 수 있는 C4-C20지방족 브릿지, 및 또한 지환족 또는 방향족 브릿지인 우레탄기 함유 일반식(Ⅰ)(메트)아크릴레이트.
  5. 제 4항에 있어서, R2가 C4-C20지방족 또는 방향족 브릿지이거나 지방족기가 중간에 결합되어 있는 복수개의 방향족 기인 우레탄기 함유 일반식(Ⅰ)(메트)아크릴레이트.
  6. 제 4항에 있어서, R4가 1이상의 에테르 또는 에스테르기가 중간에 결합된 C4-C20지방족 브릿지이거나 또는 방향족 브릿지인 우레탄기 함유 (메트)아크릴레이트.
  7. 제 2항에 있어서, X 및 Y가 1 내지 6의 정수인 우레탄기 함유 (메트)아크릴레이트.
  8. 하기식(Ⅲ)의 디이소시아네트와 하기식(Ⅱ)의 에폭시아크릴레이트를 유기 용매에서 촉매 및 억제제의 존재하에 등몰량으로 반응시키고 그 결과 제조된 하기식(Ⅳ)의 화합물과 라디칼 R1을 도입시키는 화합물을 반응시킴으로써 우레탄기를 함유하는 일반식(Ⅰ)의 (메트)아크릴레이트를 제조하는 방법.
    상기식에서, R1,R2및 R4는 제 1항에 정의한 바와 같다.
  9. 제 8항에 있어서, 결과적으로 제조된 우레탄기 함유(메트)아크릴레이트를 산화시키는 방법.
  10. 하기 성분을 성분 a)내지 h)의 총량의 100중량%가 되도록 포함하는 조성물: a)우레탄기를 함유하는 일반식(Ⅰ)의 단량체의 중합성(메트)아크릴레이트 5 내지 99중량%, 및 b)자유 라디칼 광개시제 1 내지 10중량%, c)종래 부가제 0 내지 20중량%, d)1이상의 단일, 이중 도는 다관능성(메트)아크릴레이트, 또는 그의 혼합물 0 내지 80중량%, e)1이상의 이중 또는 다관능성 에폭시드, 또는 그의 혼합물 0 내지 80%, f)OH-말단 폴리에테르 또는 폴리에스테르, 또는 그의 혼합물 0 내지 50중량%, g)양이온성 광개시제 0 내지 5중량%, 및 h)1이상의 단일, 이중 또는 다관능성 비닐 에테르 0 내지 80중량%.
  11. 피복 조성물, 접착제, 포토레지스트, 땜납 마스크 제조 또는 스테레오리소그래피에 있어서의 제10항에 따른 조성물의 용도.
  12. 후자를 화학선으로 조사시키는, 제10항에 따른 조성물의 중합방법.
  13. UV 및/또는 VIS 광원으로 신규 조성물의 층 표면 전체에 걸쳐 또는 소정 패턴에 조사하여 조사 영역에서 원하는 층 두께로 층을 고형화하고, 이 조성물의 새로운 층을 고형화된 층 위에 형성시킨 다음 표면 전체에 걸쳐 또는 소정 패턴에 조사하고, 피복 및 조사를 반복함으로써 3차원 제품이 복수개의 상호 접착성인 고형 층을 포함하는, 리소그래피 공정에 의해 제10항에 따른 조성물로부터 3차원 제품을 제조하는 방법.
  14. 제13항에 있어서, 사용되는 광원이 레이저 빔, 특히 바람직하기로는 컴퓨터로 조정되는 레이저 빔인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940019698A 1993-08-09 1994-08-08 우레탄기를함유하는(메트)아크릴레이트 KR100355949B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH237093 1993-08-09
CH93-5/2370 1993-08-09

Publications (2)

Publication Number Publication Date
KR950005820A true KR950005820A (ko) 1995-03-20
KR100355949B1 KR100355949B1 (ko) 2002-12-26

Family

ID=4232183

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019940019698A KR100355949B1 (ko) 1993-08-09 1994-08-08 우레탄기를함유하는(메트)아크릴레이트

Country Status (9)

Country Link
US (2) US5495029A (ko)
EP (1) EP0638547B1 (ko)
JP (1) JPH0776565A (ko)
KR (1) KR100355949B1 (ko)
AT (1) ATE195510T1 (ko)
AU (1) AU669635B2 (ko)
CA (1) CA2129569A1 (ko)
DE (1) DE59409479D1 (ko)
ES (1) ES2150977T3 (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100557599B1 (ko) * 1999-08-31 2006-03-10 주식회사 하이닉스반도체 광조사에 의해 라디칼을 발생하는 그룹을 포함하는 포토레지스트단량체, 그의 공중합체 및 이를 이용한 포토레지스트 조성물

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59409385D1 (de) * 1993-09-16 2000-07-06 Ciba Sc Holding Ag Vinyletherverbindungen mit zusätzlichen von Vinylethergruppen verschiedenen funktionellen Gruppen und deren Verwendung zur Formulierung härtbarer Zusammensetzungen
US5639413A (en) * 1995-03-30 1997-06-17 Crivello; James Vincent Methods and compositions related to stereolithography
RU2074673C1 (ru) * 1995-06-01 1997-03-10 Межотраслевой научно-технический комплекс "Микрохирургия глаза" Эластичный искусственный хрусталик и способ его изготовления
US5837422A (en) * 1995-07-25 1998-11-17 Mitsubishi Chemical Corporation Photopolymerizable composition and photosensitive lithographic printing plate employing it
DE19632022A1 (de) * 1995-08-11 1997-03-06 Takeda Chemical Industries Ltd Vinylesterharzzusammensetzung und daraus hergestelltes gehärtetes Produkt
EP0763779A3 (en) * 1995-09-18 1997-07-30 Mitsubishi Chem Corp Unsaturated urethane derivatives, photopolymerizable compositions containing them and photosensitive lithographic printing plate
DE69725380T2 (de) * 1996-05-16 2004-08-26 Teijin Seiki Co. Ltd. Lichthärtbare Zusammensetzung, Verfahren zur Herstellung eines lichtgehärteten geformten Gegenstands, Form und Verfahren zum Vakuumdruckgiessen und Urethanacrylat
US7332537B2 (en) * 1996-09-04 2008-02-19 Z Corporation Three dimensional printing material system and method
JP3724893B2 (ja) * 1996-09-25 2005-12-07 ナブテスコ株式会社 光学的立体造形用樹脂組成物
JP3786480B2 (ja) * 1996-10-14 2006-06-14 Ｊｓｒ株式会社 光硬化性樹脂組成物
US6166148A (en) * 1996-12-18 2000-12-26 Basf Corporation Durability enhancing agents, method therefore and cured coating compositions containing the same
US6147163A (en) * 1996-12-18 2000-11-14 Basf Corporation Acrylic oligomeric and polymeric durability enhancing agents, method therefore and cured coating compositions containing the same
DE19818312A1 (de) * 1998-04-23 1999-10-28 Bayer Ag Wäßriges Beschichtungssytem aus UV-härtenden Isocyanatgruppen aufweisenden Urethan(meth)acrylatisocyanaten
MY121423A (en) * 1998-06-26 2006-01-28 Ciba Sc Holding Ag Photopolymerizable thermosetting resin compositions
US6201036B1 (en) * 1998-07-21 2001-03-13 Mezhoiraslevoi Nauchno-Tekhnichesky Komplex “Mikrokhirurgia Glaza” Light-curable polymer material, method for making an elastic intraocular lens, and an elastic intraocular lens
CA2388046A1 (en) * 1999-11-05 2001-05-17 Z Corporation Material systems and methods of three-dimensional printing
US7300619B2 (en) * 2000-03-13 2007-11-27 Objet Geometries Ltd. Compositions and methods for use in three dimensional model printing
US20030207959A1 (en) * 2000-03-13 2003-11-06 Eduardo Napadensky Compositions and methods for use in three dimensional model printing
US8481241B2 (en) 2000-03-13 2013-07-09 Stratasys Ltd. Compositions and methods for use in three dimensional model printing
US20010050031A1 (en) * 2000-04-14 2001-12-13 Z Corporation Compositions for three-dimensional printing of solid objects
ATE291048T1 (de) 2000-05-18 2005-04-15 Nat Starch Chem Invest Vinylether und karbamat oder harnstofffunktionalität enthaltende haftklebemittel für halbleiterplatten
JP4641685B2 (ja) * 2001-09-14 2011-03-02 株式会社日本触媒 画像形成用感光性樹脂組成物
US6441121B1 (en) * 2001-09-28 2002-08-27 National Starch And Chemical Investment Holding Corporation Epoxy compounds containing styrenic or cinnamyl functionality
US6716992B2 (en) * 2002-07-22 2004-04-06 National Starch And Chemical Investment Holding Corporation Cycloaliphatic epoxy compounds containing styrenic, cinnamyl, or maleimide functionality
US6833231B2 (en) * 2002-07-31 2004-12-21 3D Systems, Inc. Toughened stereolithographic resin compositions
US7087109B2 (en) * 2002-09-25 2006-08-08 Z Corporation Three dimensional printing material system and method
US20040137368A1 (en) * 2003-01-13 2004-07-15 3D Systems, Inc. Stereolithographic resins containing selected oxetane compounds
WO2004113042A2 (en) * 2003-05-21 2004-12-29 Z Corporation Thermoplastic powder material system for appearance models from 3d printing systems
US20050059757A1 (en) * 2003-08-29 2005-03-17 Z Corporation Absorbent fillers for three-dimensional printing
DE102006006334A1 (de) * 2006-02-11 2007-08-16 Basf Coatings Ag Oligomere Urethanacrylate, Verfahren zu ihrer Herstellung und ihre Verwendung
WO2007114895A2 (en) * 2006-04-06 2007-10-11 Z Corporation Production of three-dimensional objects by use of electromagnetic radiation
EP2089215B1 (en) * 2006-12-08 2015-02-18 3D Systems Incorporated Three dimensional printing material system
WO2008086033A1 (en) * 2007-01-10 2008-07-17 Z Corporation Three-dimensional printing material system with improved color, article performance, and ease of use
US20080193740A1 (en) * 2007-01-31 2008-08-14 Nesbitt Jeffrey E Composite building material and method for making composite building material
US7968626B2 (en) 2007-02-22 2011-06-28 Z Corporation Three dimensional printing material system and method using plasticizer-assisted sintering
US8568649B1 (en) * 2007-03-20 2013-10-29 Bowling Green State University Three-dimensional printer, ceramic article and method of manufacture
US8475946B1 (en) 2007-03-20 2013-07-02 Bowling Green State University Ceramic article and method of manufacture
ES2558859T3 (es) 2011-12-15 2016-02-09 Siemens Aktiengesellschaft Procedimiento para fabricar un escudo contra el efecto corona, sistema de escudo contra el efecto corona de curado rápido y máquina eléctrica
EP2645540A1 (de) * 2012-03-28 2013-10-02 Siemens Aktiengesellschaft Glimmschutzwerkstoff für eine elektrische Maschine
CN104030947B (zh) * 2014-06-12 2016-01-13 青岛科技大学 一种磺酸盐型反应性高分子乳化剂及其制备方法和应用
US9724850B2 (en) * 2014-10-01 2017-08-08 Iconlab, Usa, Inc. Method of manufacturing an artificial elastic implant for restorative an reconstructive surgery
US10449692B2 (en) 2014-12-08 2019-10-22 Tethon Corporation Three-dimensional (3D) printing
US10639417B2 (en) 2017-10-25 2020-05-05 Carefusion 303, Inc. Lever for auto insertion and secure placement of IV tubing for use in intravenous pump systems
EP3758916A4 (en) * 2018-03-02 2021-10-27 Formlabs, Inc. LATENT CURING RESINS AND RELATED PROCESSES

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE38322B1 (en) * 1972-05-29 1978-02-15 Loctite Ltd Improvements in or relating to peroxide-initiated optical adhesives
US4100141A (en) * 1976-07-02 1978-07-11 Loctite (Ireland) Limited Stabilized adhesive and curing compositions
JPS56169065A (en) * 1980-05-31 1981-12-25 Matsushita Electric Works Ltd Manufacture of flame-resisting resin board
JPS57183706A (en) * 1981-05-05 1982-11-12 Kuraray Co Ltd Dental restorative material
DE3245563A1 (de) * 1982-12-09 1984-06-14 Henkel KGaA, 4000 Düsseldorf Verfahren zur herstellung von (meth)acrylsaeureestergruppierungen aufweisenden verbindungen, neue (meth)acrylsaeureester sowie anaerob haertende klebe- und dichtmassen
US4813875A (en) * 1984-07-31 1989-03-21 Dentsply Research & Development Corp. Chain extended urethane diacrylate and dental impression formation
US4575330A (en) * 1984-08-08 1986-03-11 Uvp, Inc. Apparatus for production of three-dimensional objects by stereolithography
DE3703130A1 (de) * 1986-07-25 1988-01-28 Bayer Ag Urethangruppen enthaltende (meth)-acrylsaeurederivate
JPS6391307A (ja) * 1986-10-03 1988-04-22 Mitsubishi Rayon Co Ltd プラスチツク歯科用表面被覆組成物
EP0360869B1 (en) * 1988-02-19 1998-01-07 Asahi Denka Kogyo Kabushiki Kaisha Resin composition for optical modeling
JPH02226249A (ja) * 1989-02-28 1990-09-07 Fuji Photo Film Co Ltd 湿し水不要感光性平版印刷版
DE4108634A1 (de) * 1991-03-16 1992-09-17 Bayer Ag Dentalwerkstoffe

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100557599B1 (ko) * 1999-08-31 2006-03-10 주식회사 하이닉스반도체 광조사에 의해 라디칼을 발생하는 그룹을 포함하는 포토레지스트단량체, 그의 공중합체 및 이를 이용한 포토레지스트 조성물

Also Published As

Publication number Publication date
EP0638547B1 (de) 2000-08-16
JPH0776565A (ja) 1995-03-20
AU6896894A (en) 1995-02-16
KR100355949B1 (ko) 2002-12-26
US5495029A (en) 1996-02-27
AU669635B2 (en) 1996-06-13
DE59409479D1 (de) 2000-09-21
ATE195510T1 (de) 2000-09-15
EP0638547A1 (de) 1995-02-15
CA2129569A1 (en) 1995-02-10
US5658712A (en) 1997-08-19
ES2150977T3 (es) 2000-12-16

Similar Documents

Publication Publication Date Title
KR950005820A (ko) 우레탄기를 함유하는 (메트)아클릴레이트
KR100294774B1 (ko) (시클로)지방족에폭시화합물
US4522693A (en) Photopolymerizable composition with acylphosphine sulfide photoinitiator and method
KR100355313B1 (ko) 부가적인관능기를갖는비닐에테르화합물
CA2126833C (en) Coating process using radiation curable compositions
US4912185A (en) Cross-linkable casting compositions
KR870007977A (ko) 저 굴절률의 플루오르-함유 수지 조성물
KR100263033B1 (ko) 디아크릴레이트와 디메타크릴레이트
DE3706355A1 (de) Additionsprodukte aus acrylaten und aminen sowie deren verwendung in strahlungshaertbaren massen
EP0614122B1 (de) Tetraacrylate enthaltende polymerisierbare Gemische
KR910008491A (ko) 감광성 혼합물 및 그의 용도
KR0147812B1 (ko) 감광성 액체 수지 조성물 및 그로부터 3차원 물체를 제조하는 방법
US4906675A (en) Active energy ray-curable composition
US4475998A (en) Modified epoxy (meth) acrylate resin and hardenable resin composition containing the same
EP0434099A2 (en) A process for obtaining textured coatings from photo-curable urea-containing compositions
EP0001466A1 (en) U.V.-curable coating composition
KR890013108A (ko) 자외선-경화성 피막 조성물 및 변성된 표면 특성의 경화 피막을 갖는 성형 플라스틱 제품의 제조방법
CA2032977A1 (en) Photo-curable urethane-containing compositions
KR100310329B1 (ko) 스테레오리소그래피에사용되는액체방사선-경화성배합물
JPH01259025A (ja) 電子線硬化性樹脂組成物
JPS6213416A (ja) 紫外線硬化樹脂組成物

Legal Events

Date Code Title Description
N231 Notification of change of applicant
A201 Request for examination
N231 Notification of change of applicant
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
LAPS Lapse due to unpaid annual fee