JPS621401B2 - - Google Patents
Info
- Publication number
- JPS621401B2 JPS621401B2 JP54088380A JP8838079A JPS621401B2 JP S621401 B2 JPS621401 B2 JP S621401B2 JP 54088380 A JP54088380 A JP 54088380A JP 8838079 A JP8838079 A JP 8838079A JP S621401 B2 JPS621401 B2 JP S621401B2
- Authority
- JP
- Japan
- Prior art keywords
- azo
- compound
- bis
- group
- polymerization
- 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
- 238000000034 method Methods 0.000 claims description 15
- -1 azo compound Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 11
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 29
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
- 239000003999 initiator Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WDHFRWNUJIDVAZ-UHFFFAOYSA-N 2-(1-cyanobutyldiazenyl)pentanenitrile Chemical compound CCCC(C#N)N=NC(C#N)CCC WDHFRWNUJIDVAZ-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- LYPHBAMYMOOWAO-UHFFFAOYSA-N bis(1-methylcyclopentyl)diazene Chemical compound C1CCCC1(C)N=NC1(C)CCCC1 LYPHBAMYMOOWAO-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782831159 DE2831159A1 (de) | 1978-07-15 | 1978-07-15 | Verfahren zur photopolymerisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5516083A JPS5516083A (en) | 1980-02-04 |
| JPS621401B2 true JPS621401B2 (enExample) | 1987-01-13 |
Family
ID=6044464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8838079A Granted JPS5516083A (en) | 1978-07-15 | 1979-07-13 | Photopolymerization of ethylenic unsaturated compound which is able to radicaly polymerize under presence of azo compound |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4279719A (enExample) |
| EP (1) | EP0006972B1 (enExample) |
| JP (1) | JPS5516083A (enExample) |
| CA (1) | CA1120886A (enExample) |
| DE (2) | DE2831159A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5986603A (ja) * | 1982-11-11 | 1984-05-18 | Showa Denko Kk | 光重合性組成物 |
| JP3442782B2 (ja) * | 1993-06-02 | 2003-09-02 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | 新規複合構造体 |
| AU2002223526A1 (en) * | 2000-09-14 | 2002-03-26 | Ciba Specialty Chemicals Holding Inc. | Acylphosphine oxide photoinitiators in methacrylate casting resins |
| DE102007035735A1 (de) * | 2006-08-16 | 2008-02-21 | Ivoclar Vivadent Ag | Pastenförmige, polymerisierbare Dentalmassen und Verfahren zu deren Herstellung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB622374A (en) * | 1946-03-16 | 1949-05-02 | Du Pont | Improvements in and relating to the photo-polymerisation of compounds containing theethylene double bond |
| DE1720367A1 (de) * | 1966-03-08 | 1971-07-08 | Ceskoslovenska Akademie Ved | Verfahren zur Herstellung von Polymeren durch Photoinitiation und geeignete Initiatoren |
| DE2130070C3 (de) | 1971-06-18 | 1981-08-20 | Röhm GmbH, 6100 Darmstadt | Verfahren zur Photopolymerisation von Acryl-, Methacrylverbindungen oder Styrol in Gegenwart von Azoverbindungen |
| US4048423A (en) * | 1974-03-21 | 1977-09-13 | Pennwalt Corporation | Process for polymerizing unsaturated monomers and unsaturated polyester resins employing unsymmetrical tertiary-aliphatic azoalkanes |
-
1978
- 1978-07-15 DE DE19782831159 patent/DE2831159A1/de not_active Withdrawn
-
1979
- 1979-03-31 EP EP79101003A patent/EP0006972B1/de not_active Expired
- 1979-03-31 DE DE7979101003T patent/DE2962170D1/de not_active Expired
- 1979-06-12 US US06/047,769 patent/US4279719A/en not_active Expired - Lifetime
- 1979-07-13 JP JP8838079A patent/JPS5516083A/ja active Granted
- 1979-07-16 CA CA000331899A patent/CA1120886A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5516083A (en) | 1980-02-04 |
| EP0006972A1 (de) | 1980-01-23 |
| DE2831159A1 (de) | 1980-01-24 |
| DE2962170D1 (de) | 1982-03-25 |
| EP0006972B1 (de) | 1982-02-24 |
| US4279719A (en) | 1981-07-21 |
| CA1120886A (en) | 1982-03-30 |
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