DE1303485B - - Google Patents
Info
- Publication number
- DE1303485B DE1303485B DEF38429A DEF0038429A DE1303485B DE 1303485 B DE1303485 B DE 1303485B DE F38429 A DEF38429 A DE F38429A DE F0038429 A DEF0038429 A DE F0038429A DE 1303485 B DE1303485 B DE 1303485B
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- trioxane
- weight
- polymerization
- ethers
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 21
- 229920000642 polymer Polymers 0.000 claims 20
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims 16
- 239000003054 catalyst Substances 0.000 claims 13
- 238000000034 method Methods 0.000 claims 10
- -1 polyoxymethylenes Polymers 0.000 claims 10
- 229920001577 copolymer Polymers 0.000 claims 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 8
- 239000000155 melt Substances 0.000 claims 8
- 238000006116 polymerization reaction Methods 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 6
- 230000007062 hydrolysis Effects 0.000 claims 6
- 238000006460 hydrolysis reaction Methods 0.000 claims 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 5
- 150000004292 cyclic ethers Chemical class 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 229920006324 polyoxymethylene Polymers 0.000 claims 5
- 230000006641 stabilisation Effects 0.000 claims 5
- 238000011105 stabilization Methods 0.000 claims 5
- 229920001897 terpolymer Polymers 0.000 claims 5
- 239000000178 monomer Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 229910015900 BF3 Inorganic materials 0.000 claims 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 230000032050 esterification Effects 0.000 claims 3
- 238000005886 esterification reaction Methods 0.000 claims 3
- 150000002334 glycols Chemical class 0.000 claims 3
- 239000004033 plastic Substances 0.000 claims 3
- 229920003023 plastic Polymers 0.000 claims 3
- 239000003381 stabilizer Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 230000004580 weight loss Effects 0.000 claims 3
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 claims 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 2
- 238000010538 cationic polymerization reaction Methods 0.000 claims 2
- 239000012954 diazonium Substances 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 2
- 238000001125 extrusion Methods 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 229910001220 stainless steel Inorganic materials 0.000 claims 2
- 239000010935 stainless steel Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
- AUAGGMPIKOZAJZ-UHFFFAOYSA-N 1,3,6-trioxocane Chemical compound C1COCOCCO1 AUAGGMPIKOZAJZ-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims 1
- JROOCDXTPKCUIO-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)CCOCC1CO1 JROOCDXTPKCUIO-UHFFFAOYSA-N 0.000 claims 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- 229930185605 Bisphenol Natural products 0.000 claims 1
- 241001295925 Gegenes Species 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 229930040373 Paraformaldehyde Natural products 0.000 claims 1
- 229930182556 Polyacetal Natural products 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 229930188620 butyrolactone Natural products 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 210000003298 dental enamel Anatomy 0.000 claims 1
- 238000006266 etherification reaction Methods 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 239000012760 heat stabilizer Substances 0.000 claims 1
- 150000002373 hemiacetals Chemical group 0.000 claims 1
- 229920006158 high molecular weight polymer Polymers 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000001746 injection moulding Methods 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 229920002521 macromolecule Polymers 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 230000008961 swelling Effects 0.000 claims 1
- 230000008646 thermal stress Effects 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 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
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/22—Copolymerisation of aldehydes or ketones with epoxy compounds
-
- 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
- C08G2/24—Copolymerisation of aldehydes or ketones with acetals
-
- 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
- C08G4/00—Condensation polymers of aldehydes or ketones with polyalcohols; Addition polymers of heterocyclic oxygen compounds containing in the ring at least once the grouping —O—C—O—
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1962F0038429 DE1303485C2 (de) | 1962-11-30 | 1962-11-30 | Verfahren zur herstellung von copolymerisaten des trioxans |
| NL300975D NL300975A (en, 2012) | 1962-11-30 | 1963-11-26 | |
| NL63300975A NL138950B (nl) | 1962-11-30 | 1963-11-26 | Werkwijze voor het bereiden van een trioxancopolymeer. |
| CH1452163A CH449268A (de) | 1962-11-30 | 1963-11-27 | Verfahren zur Herstellung von Mischpolyacetalen |
| AT952963A AT246995B (de) | 1962-11-30 | 1963-11-28 | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| FR955637A FR1376169A (fr) | 1962-11-30 | 1963-11-30 | Procédé de préparation de copolymères à base de trioxanne |
| BE640678A BE640678A (en, 2012) | 1962-11-30 | 1963-12-02 | |
| GB47546/63A GB984519A (en) | 1962-11-30 | 1963-12-02 | Copolymers and process for making them |
| US508395A US3385827A (en) | 1962-11-30 | 1965-11-17 | Trioxane terpolymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1962F0038429 DE1303485C2 (de) | 1962-11-30 | 1962-11-30 | Verfahren zur herstellung von copolymerisaten des trioxans |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1303485B true DE1303485B (en, 2012) | 1972-02-03 |
| DE1303485C2 DE1303485C2 (de) | 1979-07-19 |
Family
ID=7097335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1962F0038429 Expired DE1303485C2 (de) | 1962-11-30 | 1962-11-30 | Verfahren zur herstellung von copolymerisaten des trioxans |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3385827A (en, 2012) |
| AT (1) | AT246995B (en, 2012) |
| BE (1) | BE640678A (en, 2012) |
| CH (1) | CH449268A (en, 2012) |
| DE (1) | DE1303485C2 (en, 2012) |
| GB (1) | GB984519A (en, 2012) |
| NL (2) | NL138950B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1301096B (de) * | 1965-03-05 | 1969-08-14 | Hoechst Ag | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| US3523102A (en) * | 1966-12-14 | 1970-08-04 | Hoechst Ag | Polyoxymethylenes having lateral amino groups and process for preparing them |
| US3513223A (en) * | 1967-11-13 | 1970-05-19 | Celanese Corp | Phenol-formaldehyde resins in needle form |
| CH315369D (en, 2012) * | 1968-03-05 | 1900-01-01 | ||
| US3666714A (en) * | 1968-11-15 | 1972-05-30 | Karl Heinz Hafner | Polyacetals stabilized with secondary alkali metal phosphates |
| US4816107A (en) * | 1987-09-14 | 1989-03-28 | Hoechst Celanese Corp. | Acetal polymer bonded articles and method of making same |
| US4788258A (en) * | 1987-09-14 | 1988-11-29 | Hoechst Celanese Corporation | Low Tg non-crystalline acetal copolymers |
| US4898925A (en) * | 1988-09-12 | 1990-02-06 | Hoechst Celanese Corporation | Elastomeric acetal polymers |
| US4954400A (en) * | 1988-10-11 | 1990-09-04 | Hoechst Celanese Corp. | Articles utilizing acetal copolymer bonding resins |
| KR0146285B1 (ko) * | 1989-08-09 | 1998-08-17 | 마에다 가쓰노스께 | 폴리옥시메틸렌 다원공중합체 및 그의 성형품 |
| US4937312A (en) * | 1989-12-11 | 1990-06-26 | Hoechst Celanese Corp. | Process for producing elastomeric acetal polymers |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3027352A (en) * | 1958-02-28 | 1962-03-27 | Celanese Corp | Copolymers |
| BE576728A (en, 2012) * | 1958-03-17 | |||
| US3033803A (en) * | 1958-10-03 | 1962-05-08 | Devoe & Raynolds Co | Production of glycidyl ethers |
| FR1271297A (fr) * | 1959-08-29 | 1961-09-08 | Degussa | Procédé pour préparer des polyoxyméthylènes thermiquement et chimiquement stables |
| US3293219A (en) * | 1963-07-10 | 1966-12-20 | Tenneco Chem | Polyacetal terpolymers containing randomly recurring groups derived from a methylene-bis- |
| US3275604A (en) * | 1963-07-19 | 1966-09-27 | Celanese Corp | Moldable oxymethylene copolymers and method of preparing same |
| US3278460A (en) * | 1964-01-31 | 1966-10-11 | Union Carbide Corp | Curable aliphatic polyglycidyl ether polyamine compositions |
-
1962
- 1962-11-30 DE DE1962F0038429 patent/DE1303485C2/de not_active Expired
-
1963
- 1963-11-26 NL NL63300975A patent/NL138950B/xx not_active IP Right Cessation
- 1963-11-26 NL NL300975D patent/NL300975A/xx unknown
- 1963-11-27 CH CH1452163A patent/CH449268A/de unknown
- 1963-11-28 AT AT952963A patent/AT246995B/de active
- 1963-12-02 GB GB47546/63A patent/GB984519A/en not_active Expired
- 1963-12-02 BE BE640678A patent/BE640678A/xx unknown
-
1965
- 1965-11-17 US US508395A patent/US3385827A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CH449268A (de) | 1967-12-31 |
| BE640678A (en, 2012) | 1964-06-02 |
| AT246995B (de) | 1966-05-10 |
| DE1303485C2 (de) | 1979-07-19 |
| US3385827A (en) | 1968-05-28 |
| NL300975A (en, 2012) | |
| GB984519A (en) | 1965-02-24 |
| NL138950B (nl) | 1973-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C2 | Grant after previous publication (2nd publication) |