DE2222709C3 - Unter Luftabschluß polymerisierende Masse - Google Patents
Unter Luftabschluß polymerisierende MasseInfo
- Publication number
- DE2222709C3 DE2222709C3 DE2222709A DE2222709A DE2222709C3 DE 2222709 C3 DE2222709 C3 DE 2222709C3 DE 2222709 A DE2222709 A DE 2222709A DE 2222709 A DE2222709 A DE 2222709A DE 2222709 C3 DE2222709 C3 DE 2222709C3
- Authority
- DE
- Germany
- Prior art keywords
- monomer
- added
- mass
- mixture
- viscosity
- 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
- 239000000203 mixture Substances 0.000 title description 52
- 239000000178 monomer Substances 0.000 claims description 59
- 239000003999 initiator Substances 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims 1
- 150000002830 nitrogen compounds Chemical class 0.000 claims 1
- 150000004831 organic oxygen compounds Chemical class 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- -1 alkyl radical Chemical class 0.000 description 31
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 22
- 239000011230 binding agent Substances 0.000 description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 14
- ZBUUHLDYMKTVLT-UHFFFAOYSA-N 3-amino-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound NN1C(=O)CSC1=S ZBUUHLDYMKTVLT-UHFFFAOYSA-N 0.000 description 13
- 239000000654 additive Substances 0.000 description 13
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229940079877 pyrogallol Drugs 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 229920002689 polyvinyl acetate Polymers 0.000 description 5
- 239000011118 polyvinyl acetate Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- QZYRMODBFHTNHF-UHFFFAOYSA-N ditert-butyl benzene-1,2-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OOC(C)(C)C QZYRMODBFHTNHF-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16J—PISTONS; CYLINDERS; SEALINGS
- F16J15/00—Sealings
- F16J15/02—Sealings between relatively-stationary surfaces
- F16J15/14—Sealings between relatively-stationary surfaces by means of granular or plastic material, or fluid
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Manufacture Of Motors, Generators (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14206371A | 1971-05-10 | 1971-05-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2222709A1 DE2222709A1 (de) | 1972-11-23 |
| DE2222709B2 DE2222709B2 (de) | 1980-07-31 |
| DE2222709C3 true DE2222709C3 (de) | 1981-07-30 |
Family
ID=22498419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2222709A Expired DE2222709C3 (de) | 1971-05-10 | 1972-05-09 | Unter Luftabschluß polymerisierende Masse |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3720656A (enExample) |
| JP (1) | JPS523428B1 (enExample) |
| BR (1) | BR7202927D0 (enExample) |
| CA (1) | CA984081A (enExample) |
| DE (1) | DE2222709C3 (enExample) |
| FR (1) | FR2137539B1 (enExample) |
| GB (1) | GB1366033A (enExample) |
| IT (1) | IT952822B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868409A (en) * | 1969-09-24 | 1975-02-25 | Broadview Chem Corp | Acrylic acid esters |
| US4013710A (en) * | 1972-09-28 | 1977-03-22 | The B. F. Goodrich Company | Liquid vinylidene-terminated polymers |
| US3996308A (en) * | 1974-02-19 | 1976-12-07 | Avery Products Corporation | Anaerobic pressure sensitive adhesive composition |
| US4005055A (en) * | 1975-05-22 | 1977-01-25 | Skeist Laboratories, Incorporated | Anaerobic aminimide curing compositions |
| US4041061A (en) * | 1975-11-18 | 1977-08-09 | Johnson & Johnson | Modified cyanoacrylate monomers and methods of preparation |
| US4357440A (en) * | 1979-09-10 | 1982-11-02 | Union Carbide Corporation | Wet-adhesion aid |
| US4310631A (en) * | 1979-10-12 | 1982-01-12 | Ionics Inc. | Synthesis of water soluble cross-linkers and their use in the manufacture of anionic polymers |
| US4275227A (en) * | 1979-10-12 | 1981-06-23 | Ionics Inc. | Synthesis of water soluble cross-linkers and their use in the manufacture of anionic polymers |
| US4374720A (en) * | 1980-12-13 | 1983-02-22 | Ionics, Incorporated | Synthesis of water soluble cross-linkers and their use in the manufacture of anionic polymers |
| KR910001027B1 (ko) * | 1985-05-17 | 1991-02-19 | 와렌 그레고리 레자르 | 시아노아크릴레이트 중합 억제 조성물 |
| JP2642554B2 (ja) * | 1991-12-27 | 1997-08-20 | 電気化学工業株式会社 | 接着剤組成物 |
| IE20000440A1 (en) * | 2000-05-31 | 2003-04-02 | Loctite R & D Ltd | Semi-Solid one- or two-part compositions |
-
1971
- 1971-05-10 US US00142063A patent/US3720656A/en not_active Expired - Lifetime
-
1972
- 1972-04-04 CA CA138,840A patent/CA984081A/en not_active Expired
- 1972-04-12 GB GB1685072A patent/GB1366033A/en not_active Expired
- 1972-04-29 IT IT49955/72A patent/IT952822B/it active
- 1972-05-02 JP JP47044190A patent/JPS523428B1/ja active Pending
- 1972-05-04 FR FR7215878A patent/FR2137539B1/fr not_active Expired
- 1972-05-09 DE DE2222709A patent/DE2222709C3/de not_active Expired
- 1972-05-10 BR BR2927/72A patent/BR7202927D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT952822B (it) | 1973-07-30 |
| FR2137539A1 (enExample) | 1972-12-29 |
| BR7202927D0 (pt) | 1973-05-24 |
| DE2222709A1 (de) | 1972-11-23 |
| GB1366033A (en) | 1974-09-04 |
| DE2222709B2 (de) | 1980-07-31 |
| US3720656A (en) | 1973-03-13 |
| JPS523428B1 (enExample) | 1977-01-27 |
| FR2137539B1 (enExample) | 1978-03-03 |
| CA984081A (en) | 1976-02-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: DERZEIT KEIN VERTRETER BESTELLT |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SAF-T-LOK CHEM. CORP., DOWNERS GROVE, ILL., US |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: SPLANEMANN, R., DIPL.-ING. REITZNER, B., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |