NO133451B - - Google Patents
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- Publication number
- NO133451B NO133451B NO228672A NO228672A NO133451B NO 133451 B NO133451 B NO 133451B NO 228672 A NO228672 A NO 228672A NO 228672 A NO228672 A NO 228672A NO 133451 B NO133451 B NO 133451B
- Authority
- NO
- Norway
- Prior art keywords
- trioxane
- weight
- ppm
- copolymer
- tin
- Prior art date
Links
- 229920001577 copolymer Polymers 0.000 claims description 51
- 238000006116 polymerization reaction Methods 0.000 claims description 30
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 28
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 26
- 150000004292 cyclic ethers Chemical class 0.000 claims description 23
- 229910052718 tin Inorganic materials 0.000 claims description 21
- 238000007334 copolymerization reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000002841 Lewis acid Substances 0.000 claims description 16
- 150000007517 lewis acids Chemical class 0.000 claims description 16
- 239000002685 polymerization catalyst Substances 0.000 claims description 15
- 229910015900 BF3 Inorganic materials 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- -1 tin carboxylate Chemical class 0.000 claims description 6
- 239000011968 lewis acid catalyst Substances 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims 4
- 125000005474 octanoate group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 59
- 239000003054 catalyst Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000007858 starting material Substances 0.000 description 16
- 239000000155 melt Substances 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 12
- 239000003426 co-catalyst Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 229920001897 terpolymer Polymers 0.000 description 6
- 235000019256 formaldehyde Nutrition 0.000 description 4
- 229960004279 formaldehyde Drugs 0.000 description 4
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 4
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical class C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000004260 weight control Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000382928 Oxya Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene 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
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000000325 methylidene group Chemical class [H]C([H])=* 0.000 description 1
- TXSUIVPRHHQNTM-UHFFFAOYSA-N n'-(3-methylanilino)-n-phenyliminobenzenecarboximidamide Chemical compound CC1=CC=CC(NN=C(N=NC=2C=CC=CC=2)C=2C=CC=CC=2)=C1 TXSUIVPRHHQNTM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000011282 treatment Methods 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
- 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
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 |
|---|---|---|---|
| US15766871A | 1971-06-28 | 1971-06-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133451B true NO133451B (OSRAM) | 1976-01-26 |
| NO133451C NO133451C (OSRAM) | 1976-05-05 |
Family
ID=22564738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO228672A NO133451C (OSRAM) | 1971-06-28 | 1972-06-27 |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5545564B1 (OSRAM) |
| BE (1) | BE785424A (OSRAM) |
| CA (1) | CA984089A (OSRAM) |
| DE (1) | DE2228418A1 (OSRAM) |
| FR (1) | FR2143759B1 (OSRAM) |
| GB (1) | GB1387863A (OSRAM) |
| IT (1) | IT956870B (OSRAM) |
| NL (1) | NL7208903A (OSRAM) |
| NO (1) | NO133451C (OSRAM) |
| SE (1) | SE388424B (OSRAM) |
-
1972
- 1972-06-10 DE DE19722228418 patent/DE2228418A1/de active Pending
- 1972-06-15 GB GB2797672A patent/GB1387863A/en not_active Expired
- 1972-06-26 BE BE785424A patent/BE785424A/xx unknown
- 1972-06-26 FR FR7223022A patent/FR2143759B1/fr not_active Expired
- 1972-06-26 JP JP6335272A patent/JPS5545564B1/ja active Pending
- 1972-06-27 IT IT2627772A patent/IT956870B/it active
- 1972-06-27 SE SE844672A patent/SE388424B/xx unknown
- 1972-06-27 NO NO228672A patent/NO133451C/no unknown
- 1972-06-27 CA CA145,843A patent/CA984089A/en not_active Expired
- 1972-06-28 NL NL7208903A patent/NL7208903A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1387863A (en) | 1975-03-19 |
| BE785424A (fr) | 1972-12-27 |
| NL7208903A (OSRAM) | 1973-01-02 |
| FR2143759A1 (OSRAM) | 1973-02-09 |
| SE388424B (sv) | 1976-10-04 |
| IT956870B (it) | 1973-10-10 |
| JPS5545564B1 (OSRAM) | 1980-11-18 |
| FR2143759B1 (OSRAM) | 1976-08-06 |
| NO133451C (OSRAM) | 1976-05-05 |
| CA984089A (en) | 1976-02-17 |
| DE2228418A1 (de) | 1973-01-18 |
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