DE1795395B2 - Verfahren zur Herstellung von Polymerisaten und Mischpolymerisaten von (Meth-)Acrylsäureester oder von Acrylnitril - Google Patents
Verfahren zur Herstellung von Polymerisaten und Mischpolymerisaten von (Meth-)Acrylsäureester oder von AcrylnitrilInfo
- Publication number
- DE1795395B2 DE1795395B2 DE19681795395 DE1795395A DE1795395B2 DE 1795395 B2 DE1795395 B2 DE 1795395B2 DE 19681795395 DE19681795395 DE 19681795395 DE 1795395 A DE1795395 A DE 1795395A DE 1795395 B2 DE1795395 B2 DE 1795395B2
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- effect
- terpinolene
- weight
- monomers
- 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.)
- Granted
Links
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 10
- 229920000642 polymer Polymers 0.000 title claims description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 6
- 229920001577 copolymer Polymers 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 claims description 48
- 230000000694 effects Effects 0.000 claims description 35
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000004702 methyl esters Chemical class 0.000 claims description 9
- 230000009471 action Effects 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- 238000013016 damping Methods 0.000 claims description 6
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- -1 vinylidene compound Chemical class 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 4
- 239000011976 maleic acid Substances 0.000 claims 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 4
- 230000000379 polymerizing effect Effects 0.000 claims 3
- 229920002554 vinyl polymer Polymers 0.000 claims 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 2
- 229920001567 vinyl ester resin Polymers 0.000 claims 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims 1
- 241000723346 Cinnamomum camphora Species 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 239000001293 FEMA 3089 Substances 0.000 claims 1
- 244000062730 Melissa officinalis Species 0.000 claims 1
- 235000010654 Melissa officinalis Nutrition 0.000 claims 1
- 241000563929 Oreophasis derbianus Species 0.000 claims 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 229960000846 camphor Drugs 0.000 claims 1
- 229930008380 camphor Natural products 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000009792 diffusion process Methods 0.000 claims 1
- 230000002349 favourable effect Effects 0.000 claims 1
- 210000003608 fece Anatomy 0.000 claims 1
- 230000017525 heat dissipation Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims 1
- 239000002685 polymerization catalyst Substances 0.000 claims 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 10
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 6
- 239000004808 2-ethylhexylester Substances 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- YULMNMJFAZWLLN-UHFFFAOYSA-N methylenecyclohexane Chemical compound C=C1CCCCC1 YULMNMJFAZWLLN-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 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
-
- 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
- C08F20/42—Nitriles
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)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681795395 DE1795395B2 (de) | 1968-09-26 | 1968-09-26 | Verfahren zur Herstellung von Polymerisaten und Mischpolymerisaten von (Meth-)Acrylsäureester oder von Acrylnitril |
| FR6932760A FR2018948A1 (fr) | 1968-09-26 | 1969-09-25 | |
| GB4757369A GB1261427A (en) | 1968-09-26 | 1969-09-26 | Process for controlling the polymerisation of certain acrylic monomers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681795395 DE1795395B2 (de) | 1968-09-26 | 1968-09-26 | Verfahren zur Herstellung von Polymerisaten und Mischpolymerisaten von (Meth-)Acrylsäureester oder von Acrylnitril |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1795395A1 DE1795395A1 (de) | 1972-01-05 |
| DE1795395B2 true DE1795395B2 (de) | 1974-02-14 |
| DE1795395C3 DE1795395C3 (fr) | 1974-09-19 |
Family
ID=5708167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681795395 Granted DE1795395B2 (de) | 1968-09-26 | 1968-09-26 | Verfahren zur Herstellung von Polymerisaten und Mischpolymerisaten von (Meth-)Acrylsäureester oder von Acrylnitril |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1795395B2 (fr) |
| FR (1) | FR2018948A1 (fr) |
| GB (1) | GB1261427A (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4246386A (en) | 1978-05-08 | 1981-01-20 | Rohm And Haas Company | Ion exchange resins |
| US4375519A (en) | 1978-05-08 | 1983-03-01 | Rohm And Haas Company | Ion exchange resins |
| US4431785A (en) * | 1978-05-08 | 1984-02-14 | Rohm And Haas Company | Ion exchange resins |
| EP0376662B1 (fr) * | 1988-12-28 | 1994-08-10 | Nippon Oil And Fats Company, Limited | Matière première pour la prégélification, méthode de préparation de prégel, méthode de préparation de matière moulée et matière moulée |
| US5244926A (en) * | 1992-06-16 | 1993-09-14 | The Dow Chemical Company | Preparation of ion exchange and adsorbent copolymers |
| WO1997025381A1 (fr) | 1996-01-12 | 1997-07-17 | Mitsubishi Rayon Co., Ltd. | Resine acrylique a groupes epoxy pour revetements en poudre et son procede de fabrication |
| DE102010003881A1 (de) * | 2010-04-12 | 2011-10-13 | Voco Gmbh | Dentale Abdeckmasse |
| DE102010003884A1 (de) * | 2010-04-12 | 2011-10-13 | Voco Gmbh | Dualhärtende, mehrkomponentige dentale Zusammensetzung |
| DE102010003883A1 (de) * | 2010-04-12 | 2011-10-13 | Voco Gmbh | Lichthärtbares Kompositmaterial |
-
1968
- 1968-09-26 DE DE19681795395 patent/DE1795395B2/de active Granted
-
1969
- 1969-09-25 FR FR6932760A patent/FR2018948A1/fr active Pending
- 1969-09-26 GB GB4757369A patent/GB1261427A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1795395A1 (de) | 1972-01-05 |
| GB1261427A (en) | 1972-01-26 |
| FR2018948A1 (fr) | 1970-06-26 |
| DE1795395C3 (fr) | 1974-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |