DE1595459B2 - Verfahren zur Herstellung von Copolymerisaten des Trioxans - Google Patents
Verfahren zur Herstellung von Copolymerisaten des TrioxansInfo
- Publication number
- DE1595459B2 DE1595459B2 DE19661595459 DE1595459A DE1595459B2 DE 1595459 B2 DE1595459 B2 DE 1595459B2 DE 19661595459 DE19661595459 DE 19661595459 DE 1595459 A DE1595459 A DE 1595459A DE 1595459 B2 DE1595459 B2 DE 1595459B2
- Authority
- DE
- Germany
- Prior art keywords
- trioxane
- copolymers
- weight
- polymerization
- melt index
- 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
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 8
- 229920001577 copolymer Polymers 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000004292 cyclic ethers Chemical class 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 229910015900 BF3 Inorganic materials 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000006085 branching agent Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- -1 boron fluoride coordination complex Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/22—Copolymerisation of aldehydes or ketones with epoxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51385565A | 1965-12-14 | 1965-12-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1595459A1 DE1595459A1 (de) | 1970-02-05 |
| DE1595459B2 true DE1595459B2 (de) | 1970-11-05 |
Family
ID=24044899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661595459 Pending DE1595459B2 (de) | 1965-12-14 | 1966-11-24 | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
Country Status (6)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3050137C1 (de) * | 1979-12-17 | 1985-11-14 | Asahi Kasei Kogyo K.K., Osaka | Verfahren zur Herstellung von Polyoxymethylenen |
| US4311825A (en) * | 1980-07-21 | 1982-01-19 | National Distillers & Chemical Corp. | Acetal polymer |
| JPS601216A (ja) * | 1983-06-17 | 1985-01-07 | Polyplastics Co | トリオキサンの共重合体製造法 |
| US4975518A (en) * | 1989-05-12 | 1990-12-04 | Hoechst Celanese Corporation | Novel polyacetal copolymers of trioxane and 1,2,6-hexanetriol formal derivatives |
| US10093772B2 (en) | 2014-04-07 | 2018-10-09 | Covestro Deutschland Ag | Process for the production of polyoxymethylene block copolymers |
| EP3497148B1 (de) | 2016-08-12 | 2020-06-03 | Covestro Deutschland AG | Verfahren zur herstellung von polymeren ringöffnungsprodukten |
| EP3533815A1 (de) | 2018-02-28 | 2019-09-04 | Covestro Deutschland AG | Polyurethanweichschaumstoffe auf basis von polyoxymethylen-polyoxyalkylen-blockcopolymeren |
| EP3643730A1 (de) | 2018-10-26 | 2020-04-29 | Covestro Deutschland AG | Verfahren zur herstellung von polyoxymethylen-polyoxyalkylen-blockcopolymeren |
| EP3653657A1 (de) | 2018-11-16 | 2020-05-20 | Covestro Deutschland AG | Verfahren zur herstellung von präpolymeren umfassend einen polyoxymethylen-block |
| EP3931230A1 (de) | 2019-02-28 | 2022-01-05 | Covestro Intellectual Property GmbH & Co. KG | Isocyanat-terminierte prepolymere für die herstellung von polyurethan-integral-schaumstoffen |
| EP3838938A1 (de) | 2019-12-18 | 2021-06-23 | Covestro Deutschland AG | Verfahren zur herstellung von polyoxymethylen-polyoxyalkylen-copolymeren |
| EP3922661A1 (de) | 2020-06-12 | 2021-12-15 | Covestro Deutschland AG | Verfahren zur herstellung von polyoxymethylen-polyoxyalkylen-copolymeren |
| EP3960783A1 (de) | 2020-09-01 | 2022-03-02 | Covestro Deutschland AG | Isocyanat-terminierte prepolymere auf basis von polyoxymethylen-polyoxyalkylen-blockcopolymeren, verfahren zur deren herstellung und deren verwendung |
| EP4015555A1 (de) | 2020-12-18 | 2022-06-22 | Covestro Deutschland AG | Verfahren zur herstellung eines monols oder polyols umfassend einen polyoxymethylen-block |
| WO2022258570A1 (de) | 2021-06-10 | 2022-12-15 | Covestro Deutschland Ag | Verfahren zur herstellung von polyoxymethylen-polyoxyalkylen-copolymeren |
| EP4201973A1 (de) | 2021-12-21 | 2023-06-28 | Covestro Deutschland AG | Präpolymer umfassend einen polyoxymethylen-block und dessen herstellungsverfahren |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2786081A (en) * | 1954-01-08 | 1957-03-19 | Quaker Chemical Products Corp | Acetal condensation products |
| DE1114325B (de) * | 1958-04-03 | 1961-09-28 | Bayer Ag | Verfahren zur Herstellung von hochmolekularen Polyadditionsprodukten |
| BE624174A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1961-10-30 | |||
| DE1161423B (de) * | 1962-05-23 | 1964-01-16 | Bayer Ag | Verfahren zur Herstellung von Pfropf-polymerisaten |
-
1965
- 1965-12-14 US US513855A patent/US3436375A/en not_active Expired - Lifetime
-
1966
- 1966-11-24 DE DE19661595459 patent/DE1595459B2/de active Pending
- 1966-11-30 GB GB53539/66A patent/GB1153160A/en not_active Expired
- 1966-12-14 FR FR87466A patent/FR1505069A/fr not_active Expired
- 1966-12-14 BE BE691185D patent/BE691185A/xx unknown
- 1966-12-14 NL NL6617558A patent/NL6617558A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1595459A1 (de) | 1970-02-05 |
| GB1153160A (en) | 1969-05-29 |
| US3436375A (en) | 1969-04-01 |
| FR1505069A (fr) | 1967-12-08 |
| BE691185A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-14 |
| NL6617558A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-15 |
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