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 PDFInfo
- 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
Links
- 150000003839 salts Chemical class 0.000 title claims description 18
- 239000011368 organic material Substances 0.000 title claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 3
- -1 MF6 anion Chemical class 0.000 claims description 15
- 229910052785 arsenic Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 239000011669 selenium Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical group 0.000 claims description 3
- 150000001241 acetals Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 238000007429 general method Methods 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 229910052714 tellurium Chemical group 0.000 claims description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
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)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (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)
- **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 isC2H4, 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 isor C2H4, and R4 is C(1-8) alkyl or C(6-13) aryl.
- 2. A salt as claimed in claim 1, 5 substantially as hereinbefore described
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1518141A (en) * | 1974-05-02 | 1978-07-19 | Gen Electric | Polymerizable compositions |
GB1516512A (en) * | 1974-05-02 | 1978-07-05 | Gen Electric | Chalcogenium salts |
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 |
-
1978
- 1978-05-18 GB GB2043378A patent/GB1596000A/en not_active Expired
- 1978-09-12 DE DE19782839586 patent/DE2839586A1/en active Pending
- 1978-09-13 FR FR7826296A patent/FR2403351A1/en active Granted
- 1978-09-13 BE BE190440A patent/BE870430A/en not_active IP Right Cessation
- 1978-09-13 JP JP11184578A patent/JPS5453181A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
DE2839586A1 (en) | 1979-03-22 |
FR2403351B1 (en) | 1982-07-09 |
JPS5453181A (en) | 1979-04-26 |
BE870430A (en) | 1979-03-13 |
FR2403351A1 (en) | 1979-04-13 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19950415 |