DE2130070C3 - Verfahren zur Photopolymerisation von Acryl-, Methacrylverbindungen oder Styrol in Gegenwart von Azoverbindungen - Google Patents
Verfahren zur Photopolymerisation von Acryl-, Methacrylverbindungen oder Styrol in Gegenwart von AzoverbindungenInfo
- Publication number
- DE2130070C3 DE2130070C3 DE19712130070 DE2130070A DE2130070C3 DE 2130070 C3 DE2130070 C3 DE 2130070C3 DE 19712130070 DE19712130070 DE 19712130070 DE 2130070 A DE2130070 A DE 2130070A DE 2130070 C3 DE2130070 C3 DE 2130070C3
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- compounds
- azo
- light
- photopolymerization
- 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 title claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 7
- 125000005395 methacrylic acid group Chemical group 0.000 title claims description 7
- 239000003999 initiator Substances 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 description 35
- -1 aralkyl radical Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000178 monomer Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 6
- 230000000379 polymerizing effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- BQMDKTJDFSUWPK-UHFFFAOYSA-N 2-methyl-2-phenyldiazenylpropanenitrile Chemical compound N#CC(C)(C)N=NC1=CC=CC=C1 BQMDKTJDFSUWPK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 229940035429 isobutyl alcohol Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 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
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical group CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 description 1
- NMPRGPYJTCVHNO-UHFFFAOYSA-N 2-[(1-ethoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoic acid Chemical compound CCOC(=O)C(C)(C)N=NC(C)(C)C(O)=O NMPRGPYJTCVHNO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000012698 light-induced step-growth polymerization Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004018 waxing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712130070 DE2130070C3 (de) | 1971-06-18 | 1971-06-18 | Verfahren zur Photopolymerisation von Acryl-, Methacrylverbindungen oder Styrol in Gegenwart von Azoverbindungen |
| ES402149A ES402149A1 (es) | 1971-06-18 | 1972-04-27 | Procedimiento para la polimerizacion de compuestos etileni-camente insaturados bajo la accion de luz. |
| FR7215890A FR2141676B1 (OSRAM) | 1971-06-18 | 1972-05-04 | |
| IT6883272A IT959091B (it) | 1971-06-18 | 1972-06-08 | Procedimento per la polimerizzazio ne sotto l azione della luce |
| GB2812072A GB1366760A (en) | 1971-06-18 | 1972-06-15 | Polymerisation process |
| CA144,892A CA978894A (en) | 1971-06-18 | 1972-06-16 | Polymerisation process |
| JP6125272A JPS5644085B1 (OSRAM) | 1971-06-18 | 1972-06-19 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712130070 DE2130070C3 (de) | 1971-06-18 | 1971-06-18 | Verfahren zur Photopolymerisation von Acryl-, Methacrylverbindungen oder Styrol in Gegenwart von Azoverbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2130070A1 DE2130070A1 (de) | 1972-12-21 |
| DE2130070B2 DE2130070B2 (de) | 1980-11-06 |
| DE2130070C3 true DE2130070C3 (de) | 1981-08-20 |
Family
ID=5811013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712130070 Expired DE2130070C3 (de) | 1971-06-18 | 1971-06-18 | Verfahren zur Photopolymerisation von Acryl-, Methacrylverbindungen oder Styrol in Gegenwart von Azoverbindungen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5644085B1 (OSRAM) |
| CA (1) | CA978894A (OSRAM) |
| DE (1) | DE2130070C3 (OSRAM) |
| ES (1) | ES402149A1 (OSRAM) |
| FR (1) | FR2141676B1 (OSRAM) |
| GB (1) | GB1366760A (OSRAM) |
| IT (1) | IT959091B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2804259A1 (de) * | 1978-02-01 | 1979-08-02 | Bayer Ag | Verfahren zur herstellung staubfreier pflanzenschutzmittel-granulate sowie vorrichtung zur durchfuehrung des verfahrens |
| DE2831159A1 (de) | 1978-07-15 | 1980-01-24 | Roehm Gmbh | Verfahren zur photopolymerisation |
| JPS6343912A (ja) * | 1986-08-08 | 1988-02-25 | Arakawa Chem Ind Co Ltd | 吸水性樹脂の製造法 |
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 |
| DE1105170B (de) * | 1959-02-18 | 1961-04-20 | Basf Ag | Verfahren zur Herstellung von Polyvinylchlorid oder Vinylchlorid-mischpolymerisaten mit erhoehtem Erweichungspunkt |
| US3306888A (en) * | 1963-12-09 | 1967-02-28 | Monsanto Co | Azo compounds |
| GB1234581A (OSRAM) * | 1967-09-13 | 1971-06-03 |
-
1971
- 1971-06-18 DE DE19712130070 patent/DE2130070C3/de not_active Expired
-
1972
- 1972-04-27 ES ES402149A patent/ES402149A1/es not_active Expired
- 1972-05-04 FR FR7215890A patent/FR2141676B1/fr not_active Expired
- 1972-06-08 IT IT6883272A patent/IT959091B/it active
- 1972-06-15 GB GB2812072A patent/GB1366760A/en not_active Expired
- 1972-06-16 CA CA144,892A patent/CA978894A/en not_active Expired
- 1972-06-19 JP JP6125272A patent/JPS5644085B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2141676B1 (OSRAM) | 1974-09-27 |
| DE2130070A1 (de) | 1972-12-21 |
| IT959091B (it) | 1973-11-10 |
| GB1366760A (en) | 1974-09-11 |
| CA978894A (en) | 1975-12-02 |
| ES402149A1 (es) | 1975-03-01 |
| DE2130070B2 (de) | 1980-11-06 |
| FR2141676A1 (OSRAM) | 1973-01-26 |
| JPS5644085B1 (OSRAM) | 1981-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |