DE2719458A1 - Herstellung von copolymeren aus maleinsaeureanhydrid und vinyltrialkoxysilanen - Google Patents
Herstellung von copolymeren aus maleinsaeureanhydrid und vinyltrialkoxysilanenInfo
- Publication number
- DE2719458A1 DE2719458A1 DE19772719458 DE2719458A DE2719458A1 DE 2719458 A1 DE2719458 A1 DE 2719458A1 DE 19772719458 DE19772719458 DE 19772719458 DE 2719458 A DE2719458 A DE 2719458A DE 2719458 A1 DE2719458 A1 DE 2719458A1
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- copolymers
- maleic anhydride
- yerfahren
- excess
- 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.)
- Ceased
Links
- 229920001577 copolymer Polymers 0.000 title claims description 32
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000003999 initiator Substances 0.000 claims description 13
- 238000007334 copolymerization reaction Methods 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 238000010626 work up procedure Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- MXBCYQUALCBQIJ-RYVPXURESA-N (8s,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C1CC[C@@H]2[C@H]3C(=C)C[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 MXBCYQUALCBQIJ-RYVPXURESA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 12
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- NNBRCHPBPDRPIT-UHFFFAOYSA-N ethenyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C=C NNBRCHPBPDRPIT-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 238000012648 alternating copolymerization Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- -1 dibenzoyl peroxide Methylbenzoylperoxid Chemical compound 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FFFLABUGDFDEBD-UHFFFAOYSA-N pent-4-enoxysilane Chemical compound [SiH3]OCCCC=C FFFLABUGDFDEBD-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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 (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772719458 DE2719458A1 (de) | 1977-04-30 | 1977-04-30 | Herstellung von copolymeren aus maleinsaeureanhydrid und vinyltrialkoxysilanen |
| SE7804856A SE7804856L (sv) | 1977-04-30 | 1978-04-27 | Forfarande vid framstellning av sampolymerisat av maleinsyraanhydrid och vinyltrialkoxisilaner |
| FR7812850A FR2388838A1 (fr) | 1977-04-30 | 1978-04-28 | Procede pour l'obtention de copolymeres d'anhydride maleique et de vinyltrialcoxysilanes |
| BE187233A BE866525A (fr) | 1977-04-30 | 1978-04-28 | Procede de preparation de copolymeres d'anhydride d'acide maleique et de vinyltrialcoxysilanes |
| CA302,287A CA1104295A (en) | 1977-04-30 | 1978-04-28 | Production of copolymers of maleic acid anhydride and vinyl thialkoxy silanes |
| NL7804661A NL7804661A (nl) | 1977-04-30 | 1978-04-28 | Werkwijze voor het bereiden van copolymeren uit maleinezuuranhydride en vinyltrialkoxysilanen. |
| JP5224378A JPS53136092A (en) | 1977-04-30 | 1978-04-28 | Process for producing copolymer consisting of maleic acid and vinyl trialkoxysilane |
| GB17102/78A GB1586650A (en) | 1977-04-30 | 1978-04-28 | L trialkoxy silanes |
| IT49140/78A IT1104101B (it) | 1977-04-30 | 1978-04-28 | Procedimento per la produzione di copolimeri di anidride maleica e vinil-trialcossisilani |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772719458 DE2719458A1 (de) | 1977-04-30 | 1977-04-30 | Herstellung von copolymeren aus maleinsaeureanhydrid und vinyltrialkoxysilanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2719458A1 true DE2719458A1 (de) | 1978-11-02 |
Family
ID=6007784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772719458 Ceased DE2719458A1 (de) | 1977-04-30 | 1977-04-30 | Herstellung von copolymeren aus maleinsaeureanhydrid und vinyltrialkoxysilanen |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS53136092A (it) |
| BE (1) | BE866525A (it) |
| CA (1) | CA1104295A (it) |
| DE (1) | DE2719458A1 (it) |
| FR (1) | FR2388838A1 (it) |
| GB (1) | GB1586650A (it) |
| IT (1) | IT1104101B (it) |
| NL (1) | NL7804661A (it) |
| SE (1) | SE7804856L (it) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2560316Y2 (ja) * | 1992-12-25 | 1998-01-21 | 株式会社河合楽器製作所 | 音響反射板装置 |
| JPH0733150U (ja) * | 1993-12-07 | 1995-06-20 | 晃 近藤 | いす用のまくら |
| US5518770A (en) * | 1995-02-23 | 1996-05-21 | Betz Laboratories, Inc. | Methods and compositions for pretreatment of metals |
| WO1996035731A1 (en) * | 1995-05-08 | 1996-11-14 | Nalco Chemical Company | Dadmac/vinyl trialkoxysilane copolymers and their use in wastewater treatment |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1572851A (it) * | 1967-07-12 | 1969-06-27 |
-
1977
- 1977-04-30 DE DE19772719458 patent/DE2719458A1/de not_active Ceased
-
1978
- 1978-04-27 SE SE7804856A patent/SE7804856L/xx unknown
- 1978-04-28 BE BE187233A patent/BE866525A/xx unknown
- 1978-04-28 IT IT49140/78A patent/IT1104101B/it active
- 1978-04-28 NL NL7804661A patent/NL7804661A/xx not_active Application Discontinuation
- 1978-04-28 JP JP5224378A patent/JPS53136092A/ja active Granted
- 1978-04-28 CA CA302,287A patent/CA1104295A/en not_active Expired
- 1978-04-28 FR FR7812850A patent/FR2388838A1/fr active Granted
- 1978-04-28 GB GB17102/78A patent/GB1586650A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1572851A (it) * | 1967-07-12 | 1969-06-27 |
Non-Patent Citations (1)
| Title |
|---|
| Ind. Eng. Chem. 45, 1953, S.367-374 * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7849140A0 (it) | 1978-04-28 |
| BE866525A (fr) | 1978-08-14 |
| IT1104101B (it) | 1985-10-14 |
| FR2388838B1 (it) | 1985-05-10 |
| JPS53136092A (en) | 1978-11-28 |
| FR2388838A1 (fr) | 1978-11-24 |
| JPS6147849B2 (it) | 1986-10-21 |
| GB1586650A (en) | 1981-03-25 |
| CA1104295A (en) | 1981-06-30 |
| SE7804856L (sv) | 1978-10-31 |
| NL7804661A (nl) | 1978-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |