DE1745763B1 - Verfahren zur Herstellung von Polymethylmethacrylat - Google Patents
Verfahren zur Herstellung von PolymethylmethacrylatInfo
- Publication number
- DE1745763B1 DE1745763B1 DE1959T0017600 DET0017600A DE1745763B1 DE 1745763 B1 DE1745763 B1 DE 1745763B1 DE 1959T0017600 DE1959T0017600 DE 1959T0017600 DE T0017600 A DET0017600 A DE T0017600A DE 1745763 B1 DE1745763 B1 DE 1745763B1
- Authority
- DE
- Germany
- Prior art keywords
- mercaptan
- mercaptans
- primary
- polymethyl methacrylate
- production
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 title claims description 5
- 239000004926 polymethyl methacrylate Substances 0.000 title claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 16
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 15
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic thiol Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000373 fatty alcohol group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QGZWYBQTXJMHIW-UHFFFAOYSA-N octane-3-thiol Chemical compound CCCCCC(S)CC QGZWYBQTXJMHIW-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 210000004127 vitreous body Anatomy 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZVEZMVFBMOOHAT-UHFFFAOYSA-N nonane-1-thiol Chemical compound CCCCCCCCCS ZVEZMVFBMOOHAT-UHFFFAOYSA-N 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propyl mercaptan Natural products CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 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
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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- 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
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/14—Methyl esters, e.g. methyl (meth)acrylate
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)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1959T0017600 DE1745763B1 (de) | 1959-12-14 | 1959-12-14 | Verfahren zur Herstellung von Polymethylmethacrylat |
| CH1330160A CH433753A (de) | 1959-12-14 | 1960-11-28 | Verfahren zur Herstellung von glaskörperfreien Perlpolymerisaten |
| DK485660AA DK105003C (da) | 1959-12-14 | 1960-12-06 | Fremgangsmåde til fremstilling af optisk rene, glaslegemefri polymerisater af methylmethacrylat. |
| FR846661A FR1280753A (fr) | 1959-12-14 | 1960-12-12 | Perfectionnements aux procédés de préparation de polyméthacrylate de méthyle |
| BE598106A BE598106A (fr) | 1959-12-14 | 1960-12-13 | Procédé de préparation de polyméthacrylate de méthyle. |
| SE1206560A SE219082C1 (enrdf_load_stackoverflow) | 1959-12-14 | 1960-12-13 | |
| GB43111/60A GB907426A (en) | 1959-12-14 | 1960-12-14 | A process for the production of polymethyl methacrylates and co-polymers thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1959T0017600 DE1745763B1 (de) | 1959-12-14 | 1959-12-14 | Verfahren zur Herstellung von Polymethylmethacrylat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1745763B1 true DE1745763B1 (de) | 1970-03-19 |
Family
ID=7548645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1959T0017600 Pending DE1745763B1 (de) | 1959-12-14 | 1959-12-14 | Verfahren zur Herstellung von Polymethylmethacrylat |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE598106A (enrdf_load_stackoverflow) |
| CH (1) | CH433753A (enrdf_load_stackoverflow) |
| DE (1) | DE1745763B1 (enrdf_load_stackoverflow) |
| DK (1) | DK105003C (enrdf_load_stackoverflow) |
| FR (1) | FR1280753A (enrdf_load_stackoverflow) |
| GB (1) | GB907426A (enrdf_load_stackoverflow) |
| SE (1) | SE219082C1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0245647A1 (de) * | 1986-04-16 | 1987-11-19 | Röhm Gmbh | Polymethacrylat-Formmasse mit hoher Wärmeformbeständigkeit und hoher thermischer Stabilität |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3364182A (en) * | 1965-10-07 | 1968-01-16 | American Cyanamid Co | Polymerization of methyl methacrylate in the presence of a polythiol |
| US4246382A (en) * | 1977-11-11 | 1981-01-20 | Asahi Kasei Kogyo Kabushiki Kaisha | Solvent resistent acrylic resin and process for producing the same |
| US4369299A (en) | 1977-11-11 | 1983-01-18 | Asahi Kasei Kogyo Kabushiki Kaisha | Acrylic resin having excellent solvent resistance and moldability |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2450000A (en) * | 1943-03-20 | 1948-09-28 | Du Pont | Emulsion polymerization of methyl methacrylate |
-
1959
- 1959-12-14 DE DE1959T0017600 patent/DE1745763B1/de active Pending
-
1960
- 1960-11-28 CH CH1330160A patent/CH433753A/de unknown
- 1960-12-06 DK DK485660AA patent/DK105003C/da active
- 1960-12-12 FR FR846661A patent/FR1280753A/fr not_active Expired
- 1960-12-13 SE SE1206560A patent/SE219082C1/sl unknown
- 1960-12-13 BE BE598106A patent/BE598106A/fr unknown
- 1960-12-14 GB GB43111/60A patent/GB907426A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2450000A (en) * | 1943-03-20 | 1948-09-28 | Du Pont | Emulsion polymerization of methyl methacrylate |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0245647A1 (de) * | 1986-04-16 | 1987-11-19 | Röhm Gmbh | Polymethacrylat-Formmasse mit hoher Wärmeformbeständigkeit und hoher thermischer Stabilität |
Also Published As
| Publication number | Publication date |
|---|---|
| SE219082C1 (enrdf_load_stackoverflow) | 1968-02-20 |
| BE598106A (fr) | 1961-06-13 |
| FR1280753A (fr) | 1962-01-08 |
| DK105003C (da) | 1966-08-01 |
| CH433753A (de) | 1967-04-15 |
| GB907426A (en) | 1962-10-03 |
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