DE1187374B - Verfahren zur Polymerisation von Vinylchlorid - Google Patents
Verfahren zur Polymerisation von VinylchloridInfo
- Publication number
- DE1187374B DE1187374B DED34512A DED0034512A DE1187374B DE 1187374 B DE1187374 B DE 1187374B DE D34512 A DED34512 A DE D34512A DE D0034512 A DED0034512 A DE D0034512A DE 1187374 B DE1187374 B DE 1187374B
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- vinyl chloride
- organoaluminum compounds
- oxidizing agents
- yield
- 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
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims description 24
- 238000006116 polymerization reaction Methods 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000007800 oxidant agent Substances 0.000 claims description 13
- 239000002685 polymerization catalyst Substances 0.000 claims description 9
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000007717 exclusion Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- -1 boric acid ester Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/02—Monomers containing chlorine
- C08F14/04—Monomers containing two carbon atoms
- C08F14/06—Vinyl chloride
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)
- Polymerization Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL265610D NL265610A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1960-10-14 | ||
NL126422D NL126422C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1960-10-14 | ||
DED34512A DE1187374B (de) | 1960-10-14 | 1960-10-14 | Verfahren zur Polymerisation von Vinylchlorid |
DE19601745700 DE1745700A1 (de) | 1960-10-14 | 1960-12-31 | Verfahren zur Polymerisation von Vinylchlorid |
CH576861A CH395543A (de) | 1960-10-14 | 1961-05-17 | Verfahren zur Polymerisation von Vinylchlorid |
FR864213A FR1291401A (fr) | 1960-10-14 | 1961-06-07 | Procédé de polymérisation du chlorure de vinyle |
GB22239/61A GB919198A (en) | 1960-10-14 | 1961-06-20 | Process for polymerising vinyl chloride |
CH790761A CH427289A (de) | 1960-10-14 | 1961-07-06 | Verfahren zur Polymerisation von Vinylchlorid |
CH889461A CH421524A (de) | 1960-10-14 | 1961-07-28 | Verfahren zur Copolymerisation von Vinylchlorid mit anderen olefinisch ungesättigten Verbindungen |
GB33899/61A GB953930A (en) | 1960-10-14 | 1961-09-21 | Process for polymerising vinyl chloride |
FR873831A FR80443E (fr) | 1960-10-14 | 1961-09-21 | Procédé de polymérisation du chlorure de vinyle |
US140208A US3167534A (en) | 1960-10-14 | 1961-09-25 | Process for the polymerization of vinylchloride with a catalyst mixture of trialkyl aluminum and boric acid-trialkyl ester |
US140207A US3169949A (en) | 1960-10-14 | 1961-09-25 | Process for the polymerization of vinyl chloride with a catalyst mixture of trialkyl aluminum and boric acid trialkyl ester and a cocatalyst |
OA51890A OA01655A (fr) | 1960-10-14 | 1964-12-31 | Procédé de polymérisation du chlorure de vinyle. |
OA51892A OA081E (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1960-10-14 | 1964-12-31 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED34512A DE1187374B (de) | 1960-10-14 | 1960-10-14 | Verfahren zur Polymerisation von Vinylchlorid |
DED0035086 | 1960-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1187374B true DE1187374B (de) | 1965-02-18 |
Family
ID=25971164
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DED34512A Pending DE1187374B (de) | 1960-10-14 | 1960-10-14 | Verfahren zur Polymerisation von Vinylchlorid |
DE19601745700 Pending DE1745700A1 (de) | 1960-10-14 | 1960-12-31 | Verfahren zur Polymerisation von Vinylchlorid |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19601745700 Pending DE1745700A1 (de) | 1960-10-14 | 1960-12-31 | Verfahren zur Polymerisation von Vinylchlorid |
Country Status (7)
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0552420A3 (en) * | 1992-01-24 | 1993-09-15 | H.B. Fuller Licensing & Financing, Inc. | Water dispersed polyurethane polymer for improved coatings and adhesives |
US5703158A (en) * | 1993-09-24 | 1997-12-30 | H.B. Fuller Licensing & Financing, Inc. | Aqueous anionic poly (urethane/urea) dispersions |
US5608000A (en) * | 1993-09-24 | 1997-03-04 | H. B. Fuller Licensing & Financing, Inc. | Aqueous polyurethane dispersion adhesive compositions with improved heat resistance |
US5610232A (en) * | 1993-09-24 | 1997-03-11 | H.B. Fuller Licensing & Financing, Inc. | Aqueous non-gelling, anionic polyurethane dispersions and process for their manufacture |
US5872182A (en) * | 1994-09-09 | 1999-02-16 | H. B. Fuller Licensing & Financing, Inc. | Water-based polyurethanes for footwear |
US9080074B2 (en) | 2010-03-19 | 2015-07-14 | Bayer Materialscience Llc | Low temperature curing polyuretdione compositions |
WO2019180131A1 (de) | 2018-03-23 | 2019-09-26 | Covestro Deutschland Ag | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
US11292864B2 (en) | 2018-03-23 | 2022-04-05 | Covestro Llc | Compositions using polyuretdione resins |
US10696775B2 (en) | 2018-03-23 | 2020-06-30 | Covestro Llc | Curing for polyallophanate compositions through undercoat acid neutralization |
US10731051B2 (en) | 2018-03-23 | 2020-08-04 | Covestro Llc | Basecoat acid neutralization through inorganic salts |
US11312881B2 (en) | 2018-03-23 | 2022-04-26 | Covestro Llc | One component polyurethane/allophanate formulations with reactive reducer |
US10633477B2 (en) | 2018-03-23 | 2020-04-28 | Covestro Llc | Extended pot-life for low temperature curing polyuretdione resins |
US11440988B2 (en) | 2018-03-23 | 2022-09-13 | Covestro Llc | Polyuretdione-containing resin blend compositions |
US20210040362A1 (en) | 2019-08-08 | 2021-02-11 | Covestro Llc | Flexible polyureas for flexible packaging adhesive without aromatic amine migration |
US20210039359A1 (en) | 2019-08-08 | 2021-02-11 | Covestro Llc | Flexibilized polyurethanes for flexible packaging adhesive without aromatic amine migration |
US11884770B2 (en) | 2019-11-25 | 2024-01-30 | The University Of Southern Mississippi | Low viscosity poly(alkynyl carbamate) prepolymers |
US11352460B2 (en) | 2019-11-25 | 2022-06-07 | Covestro Llc | Waterborne azido-alkyne click compositions |
US11292866B2 (en) | 2019-11-25 | 2022-04-05 | Covestro Llc | Low viscosity poly(alkynyl carbamate) polymers |
US11267927B2 (en) | 2019-11-25 | 2022-03-08 | Covestro Llc | Azido-alkyne click and oxysilane hybrid compositions |
US11174334B2 (en) | 2019-11-25 | 2021-11-16 | Covestro Llc | Allophanate carbamate azido-alkyne click compositions |
US11312817B2 (en) | 2019-11-25 | 2022-04-26 | Covestro Llc | Polyurethane polymers cured via azido-alkyne cycloaddition at ambient or mild curing conditions |
US11261344B2 (en) | 2019-11-25 | 2022-03-01 | Covestro Llc | Waterborne azido-alkyne click compositions |
US20210179903A1 (en) | 2019-12-11 | 2021-06-17 | Covestro Llc | Adhesive produced using aspartate-terminated prepolymers |
US20210238443A1 (en) | 2020-01-30 | 2021-08-05 | Covestro Llc | Low-nco polyisocyanate compositions |
US20220089901A1 (en) | 2020-09-24 | 2022-03-24 | Covestro Llc | Clear coating compositions having low solvent content |
US20220089902A1 (en) | 2020-09-24 | 2022-03-24 | Covestro Llc | Pigmented coating compositions having low solvent content |
US20220153910A1 (en) | 2020-11-18 | 2022-05-19 | Covestro Llc | Polyurethane and polyisocyanurate hybrid coatings |
US20220153911A1 (en) | 2020-11-18 | 2022-05-19 | Covestro Llc | Polyurethane and polyisocyanurate hybrid materials and method of preparing the same |
US11732083B2 (en) | 2020-11-19 | 2023-08-22 | Covestro Llc | Polyisocyanate resins |
US20220315758A1 (en) | 2021-04-01 | 2022-10-06 | Covestro Llc | Thermoplastic polymer blends |
US11820890B2 (en) | 2021-04-01 | 2023-11-21 | Stratasys Inc | Pulverulent thermoplastic polymer blends |
US20220356369A1 (en) | 2021-04-29 | 2022-11-10 | Covestro Llc | Low-voc pigmented coating compositions for high humidity environments |
EP4543954A1 (en) | 2022-06-23 | 2025-04-30 | Covestro LLC | Low viscosity aspartate terminated prepolymers for adhesive applications |
EP4321549A1 (en) | 2022-08-09 | 2024-02-14 | Covestro LLC | Low viscosity aspartate terminated prepolymers for adhesive applications |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1170602A (fr) * | 1956-04-04 | 1959-01-16 | Hoechst Ag | Procédé de préparation de polymères et de copolymères du chlorure de vinyle |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE566532A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
BE494989A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1949-04-08 |
-
0
- NL NL126422D patent/NL126422C/xx active
- NL NL265610D patent/NL265610A/xx unknown
-
1960
- 1960-10-14 DE DED34512A patent/DE1187374B/de active Pending
- 1960-12-31 DE DE19601745700 patent/DE1745700A1/de active Pending
-
1961
- 1961-05-17 CH CH576861A patent/CH395543A/de unknown
- 1961-06-07 FR FR864213A patent/FR1291401A/fr not_active Expired
- 1961-06-20 GB GB22239/61A patent/GB919198A/en not_active Expired
- 1961-07-06 CH CH790761A patent/CH427289A/de unknown
- 1961-09-21 GB GB33899/61A patent/GB953930A/en not_active Expired
- 1961-09-25 US US140207A patent/US3169949A/en not_active Expired - Lifetime
- 1961-09-25 US US140208A patent/US3167534A/en not_active Expired - Lifetime
-
1964
- 1964-12-31 OA OA51892A patent/OA081E/xx unknown
- 1964-12-31 OA OA51890A patent/OA01655A/xx unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1170602A (fr) * | 1956-04-04 | 1959-01-16 | Hoechst Ag | Procédé de préparation de polymères et de copolymères du chlorure de vinyle |
Also Published As
Publication number | Publication date |
---|---|
NL126422C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
US3169949A (en) | 1965-02-16 |
GB953930A (en) | 1964-04-02 |
OA081E (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-15 |
GB919198A (en) | 1963-02-20 |
FR1291401A (fr) | 1962-04-20 |
OA01655A (fr) | 1969-09-20 |
CH427289A (de) | 1966-12-31 |
US3167534A (en) | 1965-01-26 |
CH395543A (de) | 1965-07-15 |
NL265610A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
DE1745700A1 (de) | 1970-07-23 |
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