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GB1596000A - Heterocyclic onium salts their preparation and their use for photopolymerisable organic materials - Google Patents

Heterocyclic onium salts their preparation and their use for photopolymerisable organic materials Download PDF

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Publication number
GB1596000A
GB1596000A GB2043378A GB2043378A GB1596000A GB 1596000 A GB1596000 A GB 1596000A GB 2043378 A GB2043378 A GB 2043378A GB 2043378 A GB2043378 A GB 2043378A GB 1596000 A GB1596000 A GB 1596000A
Authority
GB
United Kingdom
Prior art keywords
radical
salts
present
alkyl
aryl
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.)
Expired
Application number
GB2043378A
Inventor
James Vincent 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.)
General Electric Co
Original Assignee
General Electric Co
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
Priority claimed from US05/833,146 external-priority patent/US4161478A/en
Application filed by General Electric Co filed Critical General Electric Co
Publication of GB1596000A publication Critical patent/GB1596000A/en
Expired legal-status Critical Current

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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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08—Saturated oxiranes
    • C08G65/10—Saturated oxiranes characterised by the catalysts used
    • C08G65/105—Onium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/12—Sulfonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/66—Arsenic compounds
    • C07F9/68—Arsenic compounds without As—C bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/90—Antimony compounds
    • C07F9/902—Compounds without antimony-carbon linkages
    • 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
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F236/14—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
    • C08F236/16—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen containing halogen
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymerisation Methods In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

(54) HETEROCYCLIC ONIUM SALTS, THEIR PREPARATION AND THEIR USE FOR PHOTOPOLYMERIZABLE ORGANIC MATERIALS (71) We, GENERAL ELECTRIC COMPANY, a corporation organised and existing under the laws of the State of New York, United States of America, of 1 River Road, Schenectady 12345, State of New York, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention relates to onium salts of Group VIa elements having an MF6 anion, where M Is an element selected from P, As and Sb.
The salts of the present invention can be used in combination with various photopolymerizable organic materials, such as cyclic ethers, cyclic esters, polyvinyl acetals, epoxy resins, etc., to produce UV curable compositions and heat curable compositions. The salts of the present invention are a modification of or improvement of the salts described and claimed in our Patent No. 1516512 and are included by the formula, [(R)a(R1)h(R2)cXi+[MF6i, (I) where R is a monovalent aromatic radical, R1 is a monovalent alkyl, cycloalkyl or substituted alkyl radical, R2 is a polyvalent organic aliphatic or aromatic radical forming a heterocyclic or fused ring structure, X is sulfur, selenium, or tellurium M is selected from P, As andSbl a is 0 or a whole number equal to 1, to 3 inclusive, b is 0, 1 or 2 inclusive, c is 0 or 1 and the sum of a+b+c satisfied the valence of X.
The present invention provides a salt having the formula,
where M is selected from P, As and Sb, X is sulfur or selenium, R3 is an alkyl radical, cycloalkyl radical, aryl radical or a derivative thereof, Z is
C2H4, and R4 is Cj18 alkyl or C(8.13) aryl.
Procedures which can be used to prepare the compounds of the present invention are shown in J. W. Knapczyk and W. E.
McEwen, J. Am, Chem, Soc., 91 (1969): A.
L. Maycock and G. A. Berchtols, J. Org.
Chem., 35 No. 8, 2532 (1970); H. M. Pitt, U.S. Patent 2,807,648, E. Goethals and P. De Radzetzky, Bul. Soc. Chim. Belg., 73 546 (1964); H. M. Leichester and F. W. Bergstrom, J.
Am. Chem. Soc., 51 3587 (1929). etc.
Patent Specification No. 1516512 also shows general methods of producing salts of the present invention.
WHAT WE CLAIM IS: 1. A salt having the formula,
where M is selected from P, As and Sb, X is sulfur or selenium, R3 is an alkyl radical,
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (2)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    (54) HETEROCYCLIC ONIUM SALTS, THEIR PREPARATION AND THEIR USE FOR PHOTOPOLYMERIZABLE ORGANIC MATERIALS (71) We, GENERAL ELECTRIC COMPANY, a corporation organised and existing under the laws of the State of New York, United States of America, of 1 River Road, Schenectady 12345, State of New York, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention relates to onium salts of Group VIa elements having an MF6 anion, where M Is an element selected from P, As and Sb.
    The salts of the present invention can be used in combination with various photopolymerizable organic materials, such as cyclic ethers, cyclic esters, polyvinyl acetals, epoxy resins, etc., to produce UV curable compositions and heat curable compositions. The salts of the present invention are a modification of or improvement of the salts described and claimed in our Patent No.
    1516512 and are included by the formula, [(R)a(R1)h(R2)cXi+[MF6i, (I) where R is a monovalent aromatic radical, R1 is a monovalent alkyl, cycloalkyl or substituted alkyl radical, R2 is a polyvalent organic aliphatic or aromatic radical forming a heterocyclic or fused ring structure, X is sulfur, selenium, or tellurium M is selected from P, As andSbl a is 0 or a whole number equal to 1, to 3 inclusive, b is 0, 1 or 2 inclusive, c is 0 or 1 and the sum of a+b+c satisfied the valence of X.
    The present invention provides a salt having the formula,
    where M is selected from P, As and Sb, X is sulfur or selenium, R3 is an alkyl radical, cycloalkyl radical, aryl radical or a derivative thereof, Z is
    C2H4, and R4 is Cj18 alkyl or C(8.13) aryl.
    Procedures which can be used to prepare the compounds of the present invention are shown in J. W. Knapczyk and W. E.
    McEwen, J. Am, Chem, Soc., 91 (1969): A.
    L. Maycock and G. A. Berchtols, J. Org.
    Chem., 35 No. 8, 2532 (1970); H. M. Pitt, U.S. Patent 2,807,648, E. Goethals and P. De Radzetzky, Bul. Soc. Chim. Belg., 73 546 (1964); H. M. Leichester and F. W. Bergstrom, J.
    Am. Chem. Soc., 51 3587 (1929). etc.
    Patent Specification No. 1516512 also shows general methods of producing salts of the present invention.
    WHAT WE CLAIM IS: 1. A salt having the formula,
    where M is selected from P, As and Sb, X is sulfur or selenium, R3 is an alkyl radical, cycloalkyl radical, aryl radical or a derivative thereof, Z is
    or C2H4, and R4 is C(1-8) alkyl or C(6-13) aryl.
  2. 2. A salt as claimed in claim 1, 5 substantially as hereinbefore described
GB2043378A 1977-09-14 1978-05-18 Heterocyclic onium salts their preparation and their use for photopolymerisable organic materials Expired GB1596000A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/833,146 US4161478A (en) 1974-05-02 1977-09-14 Photoinitiators

Publications (1)

Publication Number Publication Date
GB1596000A true GB1596000A (en) 1981-08-19

Family

ID=25263563

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2043378A Expired GB1596000A (en) 1977-09-14 1978-05-18 Heterocyclic onium salts their preparation and their use for photopolymerisable organic materials

Country Status (5)

Country Link
JP (1) JPS5453181A (en)
BE (1) BE870430A (en)
DE (1) DE2839586A1 (en)
FR (1) FR2403351A1 (en)
GB (1) GB1596000A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59147001A (en) * 1983-02-07 1984-08-23 ゼネラル・エレクトリツク・カンパニイ Photosettable composition
DE3537401A1 (en) * 1984-10-22 1986-04-24 General Electric Co., Schenectady, N.Y. Process for the preparation of triarylsulphonium salts
US5399596A (en) * 1988-03-03 1995-03-21 Sanshin Kagaku Kogyo Co., Ltd. Polyfluoride sulfonium compounds and polymerization initiator thereof
US5466845A (en) * 1992-06-12 1995-11-14 Wacker-Chemie Gmbh Sulfonium salts and process for their preparation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1518141A (en) * 1974-05-02 1978-07-19 Gen Electric Polymerizable compositions
GB1516511A (en) * 1974-05-02 1978-07-05 Gen Electric Curable epoxide compositions
IE42085B1 (en) * 1974-09-18 1980-06-04 Ici Ltd Photopolymerisable compositions
US4069054A (en) * 1975-09-02 1978-01-17 Minnesota Mining And Manufacturing Company Photopolymerizable composition containing a sensitized aromatic sulfonium compound and a cationacally polymerizable monomer
GB1604954A (en) * 1977-08-05 1981-12-16 Gen Electric Photocurable compositions and method for curing

Also Published As

Publication number Publication date
DE2839586A1 (en) 1979-03-22
JPS5453181A (en) 1979-04-26
FR2403351A1 (en) 1979-04-13
FR2403351B1 (en) 1982-07-09
BE870430A (en) 1979-03-13

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PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19950415