EP0544842A1 - Mittels elektronenstrahlen härtbare epoxydharzzusammensetzungen - Google Patents

Mittels elektronenstrahlen härtbare epoxydharzzusammensetzungen

Info

Publication number
EP0544842A1
EP0544842A1 EP92902738A EP92902738A EP0544842A1 EP 0544842 A1 EP0544842 A1 EP 0544842A1 EP 92902738 A EP92902738 A EP 92902738A EP 92902738 A EP92902738 A EP 92902738A EP 0544842 A1 EP0544842 A1 EP 0544842A1
Authority
EP
European Patent Office
Prior art keywords
metal halide
silicone
epoxy
monomers
onium salt
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP92902738A
Other languages
English (en)
French (fr)
Other versions
EP0544842A4 (en
Inventor
James V. Crivello
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of EP0544842A1 publication Critical patent/EP0544842A1/de
Publication of EP0544842A4 publication Critical patent/EP0544842A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • 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
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
    • C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
    • 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
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • Electrocurtin Electron Beam apparatus supplied by Energy Sciences, Corp. Wilmington, MA was used operating at a voltage of 165 KeV. Samples were placed on a poly(ethylene terephthalate) web operated at a fixed rate. The dosage received by the sample was varied by adjustment of the electrode amperage.
  • Silicone-epoxy monomers are more reactive than simple epoxy monomers such as I in photoinitiated cationic
  • multifunctional epoxy monomers undergo facile e-beam induced cationic polymerization in the presence of oxygen. What is even more surprising and unexpected is that the dose requirements in the presence of oxygen are not substantially higher than under nitrogen. Approximately 0.5 Mrad is the limiting dose necessary for the cure of a 3 mil film of monomer II in the presence of 0.5 mole % of
  • diaryliodosonium triarylsulfoxonium, diarylbromonium, diarylchloronium and phenacyldialkylsulfonium
  • benzyldialkylsulfonium and hydroxyphenyldialkylsulfonium salts those bearing the SbF 6 - anions are preferred.
  • electrons from a heated linear cathode are accelerated under high electric potential onto the surface of the substrate.
  • Other, similarly designed accelerators employ hot cathodes with accelerating and focusing magnets to deliver a highly penetrating beam of electrons.
  • Van de Graff accelerator which generates high energy electrons by classical electrostatic methods can be used.
  • ⁇ -irradiation from a 60 Co source can be used for curing.
  • fast electrons are generated by interaction of the ⁇ -irradiation with the monomer.
  • Still another technique involves focusing a high energy electron beam onto a heavy metal conversion target which converts the electrons to highly penetrating x-rays which can be used to achieve the desired cure.
  • the e-beam curing compositions may also include a wide assortment of fibrous and particulate fillers, adhesion promoting agents, pigments, dyes and flating or leveling agents.
  • novel e-beam curable epoxy monomers and oligomers can be applied to a wide diversity of applications. Among those which may be mentioned are decorative, protective and insulating coatings for wood, glass, metals and plastics, printing inks and adhesives. One recent application which is being considered is the use of e-beam curable inks for the rapid non-polluting printing of currency and stamps.
  • Silicone epoxy monomers in addition to being rapidly curing are non-toxic .
  • Other monomers whose structures are also described in this disclosure should also be similarly non- toxic.
  • Tg's temperature properties
  • solvent resistance and mechanical properties As well as excellent solvent resistance and mechanical properties.
  • e-beam curing avoids the high temperatures and long times used in conventional composites fabrication and has the potential of greatly improving the mechanical properties of the final composite. This is achieved as a result of curing at room temperature which reduces the mechanical strain in the composites which results from a mismatch of the
  • R is an alkylene, arylene, siloxane group or mixture of these.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
EP19920902738 1991-01-04 1991-11-22 Electron beam curable epoxy compositions Withdrawn EP0544842A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US63810591A 1991-01-04 1991-01-04
US638105 2000-08-11

Publications (2)

Publication Number Publication Date
EP0544842A1 true EP0544842A1 (de) 1993-06-09
EP0544842A4 EP0544842A4 (en) 1993-07-21

Family

ID=24558664

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19920902738 Withdrawn EP0544842A4 (en) 1991-01-04 1991-11-22 Electron beam curable epoxy compositions

Country Status (2)

Country Link
EP (1) EP0544842A4 (de)
WO (1) WO1992012183A1 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10001228B4 (de) * 2000-01-13 2007-01-04 3M Espe Ag Polymerisierbare Zubereitungen auf der Basis von siliziumhaltigen Epoxiden
US6832036B2 (en) 2002-10-11 2004-12-14 Polyset Company, Inc. Siloxane optical waveguides
JP2008501825A (ja) * 2004-06-01 2008-01-24 ダウ コーニング コーポレーション ナノ及びマイクロリソグラフィー用の材料組成物
JP6904245B2 (ja) * 2017-12-27 2021-07-14 信越化学工業株式会社 感光性樹脂組成物、パターン形成方法、及び光半導体素子の製造方法
US11235522B2 (en) 2018-10-04 2022-02-01 Continuous Composites Inc. System for additively manufacturing composite structures

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4101513A (en) * 1977-02-02 1978-07-18 Minnesota Mining And Manufacturing Company Catalyst for condensation of hydrolyzable silanes and storage stable compositions thereof
US4310469A (en) * 1978-12-29 1982-01-12 General Electric Company Diaryliodonium salts
DE3629701A1 (de) * 1985-09-04 1987-03-05 Ciba Geigy Ag Strahlenhaertung von kationisch polymerisierbaren verbindungen
EP0389927A2 (de) * 1989-03-30 1990-10-03 General Electric Company Epoxysiloxan-Härtungspromotor und Beschleuniger für kationische Härtungssysteme
EP0404029A1 (de) * 1989-06-22 1990-12-27 General Electric Company Nahezu geruchlose, UV-härtbare Polyorganosiloxan-Trennmittel-Überzugsmischungen und Verfahren zum Beschichten

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4529490A (en) * 1983-05-23 1985-07-16 General Electric Company Photopolymerizable organic compositions and diaryliodonium ketone salts used therein
CA1305823C (en) * 1986-08-29 1992-07-28 Union Carbide Corporation Photocurable blends of cyclic ethers and cycloaliphatic epoxides
US4990546A (en) * 1990-03-23 1991-02-05 General Electric Company UV-curable silphenylene-containing epoxy functional silicones

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4101513A (en) * 1977-02-02 1978-07-18 Minnesota Mining And Manufacturing Company Catalyst for condensation of hydrolyzable silanes and storage stable compositions thereof
US4310469A (en) * 1978-12-29 1982-01-12 General Electric Company Diaryliodonium salts
DE3629701A1 (de) * 1985-09-04 1987-03-05 Ciba Geigy Ag Strahlenhaertung von kationisch polymerisierbaren verbindungen
EP0389927A2 (de) * 1989-03-30 1990-10-03 General Electric Company Epoxysiloxan-Härtungspromotor und Beschleuniger für kationische Härtungssysteme
EP0404029A1 (de) * 1989-06-22 1990-12-27 General Electric Company Nahezu geruchlose, UV-härtbare Polyorganosiloxan-Trennmittel-Überzugsmischungen und Verfahren zum Beschichten

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JOURAL OF POLYMER SCIENCE PART A: POLYMER CHEMISTRY EDITION vol. 28, no. 3, 1990, NEW YORK pages 479 - 503 , XP141356 J.V. CRIVELLO 'THE SYNTHESIS, CHARACTERIZATION, AND PHOTOINITIATED CATIONIC POLYMERIZATION OF SILICON-CONTAINING EPOXY RESINS' *
See also references of WO9212183A1 *

Also Published As

Publication number Publication date
EP0544842A4 (en) 1993-07-21
WO1992012183A1 (en) 1992-07-23

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