DE2505110A1 - Verfahren zur herstellung von festen thermoplastischen terpolymerisaten des trioxans - Google Patents
Verfahren zur herstellung von festen thermoplastischen terpolymerisaten des trioxansInfo
- Publication number
- DE2505110A1 DE2505110A1 DE19752505110 DE2505110A DE2505110A1 DE 2505110 A1 DE2505110 A1 DE 2505110A1 DE 19752505110 DE19752505110 DE 19752505110 DE 2505110 A DE2505110 A DE 2505110A DE 2505110 A1 DE2505110 A1 DE 2505110A1
- Authority
- DE
- Germany
- Prior art keywords
- trioxane
- percent
- parts
- weight
- polymerization
- 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.)
- Withdrawn
Links
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000007787 solid Substances 0.000 title claims description 10
- 229920001169 thermoplastic Polymers 0.000 title claims description 8
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 14
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 229920001897 terpolymer Polymers 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- -1 aralkyl radical Chemical group 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- QLCJOAMJPCOIDI-UHFFFAOYSA-N 1-(butoxymethoxy)butane Chemical compound CCCCOCOCCCC QLCJOAMJPCOIDI-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- AFSIIZRPQXBCFM-UHFFFAOYSA-N tert-butyl perchlorate Chemical compound CC(C)(C)OCl(=O)(=O)=O AFSIIZRPQXBCFM-UHFFFAOYSA-N 0.000 description 4
- CZLMRJZAHXYRIX-UHFFFAOYSA-N 1,3-dioxepane Chemical compound C1CCOCOC1 CZLMRJZAHXYRIX-UHFFFAOYSA-N 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229940105990 diglycerin Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- BGCSUUSPRCDKBQ-UHFFFAOYSA-N 2,4,8,10-tetraoxaspiro[5.5]undecane Chemical compound C1OCOCC21COCOC2 BGCSUUSPRCDKBQ-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 238000000071 blow moulding Methods 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- 229910001948 sodium oxide Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ULAGGPJVDRGWTI-UHFFFAOYSA-N 1,3,5-trioxepane Chemical compound C1COCOCO1 ULAGGPJVDRGWTI-UHFFFAOYSA-N 0.000 description 1
- AUAGGMPIKOZAJZ-UHFFFAOYSA-N 1,3,6-trioxocane Chemical compound C1COCOCCO1 AUAGGMPIKOZAJZ-UHFFFAOYSA-N 0.000 description 1
- CJSITSBWCLTCAP-UHFFFAOYSA-N 1,3-dioxocane Chemical compound C1CCOCOCC1 CJSITSBWCLTCAP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HOMDJHGZAAKUQV-UHFFFAOYSA-N 1-(propoxymethoxy)propane Chemical compound CCCOCOCCC HOMDJHGZAAKUQV-UHFFFAOYSA-N 0.000 description 1
- KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical group CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 description 1
- WVRSKDLYHADNMN-UHFFFAOYSA-N 2-(1,3-dioxolan-2-ylmethoxymethyl)-1,3-dioxolane Chemical compound O1CCOC1COCC1OCCO1 WVRSKDLYHADNMN-UHFFFAOYSA-N 0.000 description 1
- WDEVXRIFJZNMKM-UHFFFAOYSA-N 2-(propan-2-yloxymethoxy)propane Chemical compound CC(C)OCOC(C)C WDEVXRIFJZNMKM-UHFFFAOYSA-N 0.000 description 1
- GBTVFZDADUZIIQ-UHFFFAOYSA-N 4-(1,3-dioxolan-4-ylmethoxymethyl)-1,3-dioxolane Chemical compound C1OCOC1COCC1COCO1 GBTVFZDADUZIIQ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- JCTHGPXQXLMSDK-UHFFFAOYSA-N bis(Benzyloxy)methane Chemical compound C=1C=CC=CC=1COCOCC1=CC=CC=C1 JCTHGPXQXLMSDK-UHFFFAOYSA-N 0.000 description 1
- 230000006583 body weight regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920005605 branched copolymer Polymers 0.000 description 1
- RXOFZQSGVJHUDI-UHFFFAOYSA-N butyl perchlorate Chemical compound CCCCOCl(=O)(=O)=O RXOFZQSGVJHUDI-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000003420 transacetalization reaction Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 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
- C08G2/10—Polymerisation of cyclic oligomers of formaldehyde
-
- 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
- C08G2/38—Block or graft polymers prepared by polymerisation of aldehydes or ketones on to macromolecular 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)
- Polyethers (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752505110 DE2505110A1 (de) | 1975-02-07 | 1975-02-07 | Verfahren zur herstellung von festen thermoplastischen terpolymerisaten des trioxans |
| NL7514089A NL7514089A (nl) | 1975-02-07 | 1975-12-03 | Werkwijze voor het bereiden van vaste, thermoplas- tische terpolymeren van trioxan. |
| FR7537585A FR2300100A1 (fr) | 1975-02-07 | 1975-12-09 | Procede de preparation de terpolymeres solides thermoplastiques du trioxanne |
| GB50401/75A GB1517790A (en) | 1975-02-07 | 1975-12-09 | Process for the production of solid thermoplastic terpolymers of trioxane |
| US05/655,358 US4108838A (en) | 1975-02-07 | 1976-02-05 | Process for the production of solid thermoplastic terpolymerizate of trioxane |
| IT47969/76A IT1060481B (it) | 1975-02-07 | 1976-02-05 | Procedimento per la produzione di terpolimeri di triossano termoplastici solidi |
| BE6045353A BE838359A (fr) | 1975-02-07 | 1976-02-06 | Procede pour la preparation de terpolymeres, thermoplastiques solides du trioxanne et produits obtenus |
| JP1216176A JPS5337272B2 (enExample) | 1975-02-07 | 1976-02-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752505110 DE2505110A1 (de) | 1975-02-07 | 1975-02-07 | Verfahren zur herstellung von festen thermoplastischen terpolymerisaten des trioxans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2505110A1 true DE2505110A1 (de) | 1976-08-19 |
Family
ID=5938311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752505110 Withdrawn DE2505110A1 (de) | 1975-02-07 | 1975-02-07 | Verfahren zur herstellung von festen thermoplastischen terpolymerisaten des trioxans |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4108838A (enExample) |
| JP (1) | JPS5337272B2 (enExample) |
| BE (1) | BE838359A (enExample) |
| DE (1) | DE2505110A1 (enExample) |
| FR (1) | FR2300100A1 (enExample) |
| GB (1) | GB1517790A (enExample) |
| IT (1) | IT1060481B (enExample) |
| NL (1) | NL7514089A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201500443A (zh) * | 2013-04-18 | 2015-01-01 | Basf Se | 聚甲醛共聚物及熱塑性ｐｏｍ組成物 |
| CN106661310B (zh) * | 2014-05-21 | 2019-08-13 | 巴斯夫欧洲公司 | 改进模制品的挠曲韧性的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE624203A (enExample) * | 1961-10-27 | |||
| US3293219A (en) * | 1963-07-10 | 1966-12-20 | Tenneco Chem | Polyacetal terpolymers containing randomly recurring groups derived from a methylene-bis- |
| DE1570588A1 (de) * | 1965-07-10 | 1970-04-09 | Hoechst Ag | Verfahren zur Herstellung von Polyacetalen |
| DE1595596A1 (de) * | 1966-03-04 | 1970-04-30 | Hoechst Ag | Verfahren zur Herstellung von Mischpolymerisaten |
-
1975
- 1975-02-07 DE DE19752505110 patent/DE2505110A1/de not_active Withdrawn
- 1975-12-03 NL NL7514089A patent/NL7514089A/xx not_active Application Discontinuation
- 1975-12-09 GB GB50401/75A patent/GB1517790A/en not_active Expired
- 1975-12-09 FR FR7537585A patent/FR2300100A1/fr active Granted
-
1976
- 1976-02-05 US US05/655,358 patent/US4108838A/en not_active Expired - Lifetime
- 1976-02-05 IT IT47969/76A patent/IT1060481B/it active
- 1976-02-06 JP JP1216176A patent/JPS5337272B2/ja not_active Expired
- 1976-02-06 BE BE6045353A patent/BE838359A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4108838A (en) | 1978-08-22 |
| GB1517790A (en) | 1978-07-12 |
| IT1060481B (it) | 1982-08-20 |
| BE838359A (fr) | 1976-08-06 |
| JPS5337272B2 (enExample) | 1978-10-07 |
| JPS51103996A (enExample) | 1976-09-14 |
| NL7514089A (nl) | 1976-08-10 |
| FR2300100A1 (fr) | 1976-09-03 |
| FR2300100B1 (enExample) | 1980-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8141 | Disposal/no request for examination |