IL94480A - Polymerization of cyclic sites capable of polymerization of cationic oxonium ion while opening a ring - Google Patents
Polymerization of cyclic sites capable of polymerization of cationic oxonium ion while opening a ringInfo
- Publication number
- IL94480A IL94480A IL9448090A IL9448090A IL94480A IL 94480 A IL94480 A IL 94480A IL 9448090 A IL9448090 A IL 9448090A IL 9448090 A IL9448090 A IL 9448090A IL 94480 A IL94480 A IL 94480A
- Authority
- IL
- Israel
- Prior art keywords
- monomer
- polymerisation
- catalyst
- hydroxy
- process according
- Prior art date
Links
- -1 cationic oxonium ion Chemical group 0.000 title claims description 41
- 150000004292 cyclic ethers Chemical class 0.000 title claims description 21
- 238000007151 ring opening polymerisation reaction Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 claims abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 30
- 239000011541 reaction mixture Substances 0.000 claims abstract description 19
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 239000000178 monomer Substances 0.000 claims description 74
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 239000002243 precursor Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- 150000002924 oxiranes Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 12
- 150000002921 oxetanes Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 229920005604 random copolymer Polymers 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 6
- 230000000977 initiatory effect Effects 0.000 claims description 5
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 4
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 3
- 125000005335 azido alkyl group Chemical group 0.000 claims description 3
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000005703 substituted oxyalkylene group Chemical group 0.000 claims description 2
- 230000000063 preceeding effect Effects 0.000 claims 6
- SMRVJNGSLACCEY-UHFFFAOYSA-N 2,2-bis(azidomethyl)oxetane Chemical compound [N-]=[N+]=NCC1(CN=[N+]=[N-])CCO1 SMRVJNGSLACCEY-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- 125000002091 cationic group Chemical group 0.000 abstract description 13
- 150000002009 diols Chemical class 0.000 abstract description 12
- 239000012535 impurity Substances 0.000 abstract description 12
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 abstract description 10
- 125000004122 cyclic group Chemical group 0.000 abstract description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 8
- 239000003999 initiator Substances 0.000 abstract description 7
- 229920001971 elastomer Polymers 0.000 abstract description 4
- 239000000806 elastomer Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000012442 inert solvent Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 abstract description 2
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000011109 contamination Methods 0.000 description 10
- 241000894007 species Species 0.000 description 10
- 229910002651 NO3 Inorganic materials 0.000 description 9
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- ADZAAKGRMMGJKM-UHFFFAOYSA-N oxiran-2-ylmethyl nitrate Chemical compound [O-][N+](=O)OCC1CO1 ADZAAKGRMMGJKM-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 101100514056 Rhodobacter capsulatus modD gene Proteins 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052787 antimony Chemical group 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Chemical group 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
- IXYHLWZRPFVFON-UHFFFAOYSA-N (3-methyloxetan-3-yl)methyl nitrate Chemical compound [O-][N+](=O)OCC1(C)COC1 IXYHLWZRPFVFON-UHFFFAOYSA-N 0.000 description 1
- DNBCBAXDWNDRNO-FOSCPWQOSA-N (3aS,6aR)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxamide Chemical compound COC1=NSC(NC(=O)N2C[C@H]3CC(C[C@H]3C2)N(C)C=2C=3C=CNC=3N=CN=2)=N1 DNBCBAXDWNDRNO-FOSCPWQOSA-N 0.000 description 1
- CJTAOJBBFSUSNB-UHFFFAOYSA-N 2-(1,1,2,2-tetrachloroethyl)oxirane Chemical compound ClC(Cl)C(Cl)(Cl)C1CO1 CJTAOJBBFSUSNB-UHFFFAOYSA-N 0.000 description 1
- DIYZRTRTCGAIKG-UHFFFAOYSA-N 2-(dichloromethyl)oxirane Chemical compound ClC(Cl)C1CO1 DIYZRTRTCGAIKG-UHFFFAOYSA-N 0.000 description 1
- GRTWZACANJOGHU-UHFFFAOYSA-N 2-butyloxirene Chemical compound CCCCC1=CO1 GRTWZACANJOGHU-UHFFFAOYSA-N 0.000 description 1
- BCJPEZMFAKOJPM-UHFFFAOYSA-N 2-ethyl-3-methyloxirane Chemical compound CCC1OC1C BCJPEZMFAKOJPM-UHFFFAOYSA-N 0.000 description 1
- KKBZXIJAEUJECM-UHFFFAOYSA-N 3-(2,2-dinitropropoxymethyl)-3-methyloxetane Chemical compound [O-][N+](=O)C([N+]([O-])=O)(C)COCC1(C)COC1 KKBZXIJAEUJECM-UHFFFAOYSA-N 0.000 description 1
- NBUAJOLSZMKRIT-UHFFFAOYSA-N 5-methyloctan-3-ol Chemical compound CCCC(C)CC(O)CC NBUAJOLSZMKRIT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229920006125 amorphous polymer Polymers 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- MDVPRIBCAFEROC-UHFFFAOYSA-N oct-1-en-1-ol Chemical compound CCCCCCC=CO MDVPRIBCAFEROC-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FWICBZQTZDXXOL-UHFFFAOYSA-N oxecane Chemical compound C1CCCCOCCCC1 FWICBZQTZDXXOL-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/105—Onium 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2654—Aluminium or boron; Compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyesters Or Polycarbonates (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898912456A GB8912456D0 (en) | 1989-05-31 | 1989-05-31 | Polymerisation of cyclic ether monomers capable of undergoing cationic oxonium ion ring-opening polymerisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL94480A true IL94480A (en) | 1994-12-29 |
Family
ID=10657619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9448090A IL94480A (en) | 1989-05-31 | 1990-05-23 | Polymerization of cyclic sites capable of polymerization of cationic oxonium ion while opening a ring |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5313000A (OSRAM) |
| EP (1) | EP0474696B1 (OSRAM) |
| JP (1) | JPH04505934A (OSRAM) |
| AT (1) | ATE145413T1 (OSRAM) |
| AU (1) | AU635034B2 (OSRAM) |
| BR (1) | BR9007410A (OSRAM) |
| DE (1) | DE69029196T2 (OSRAM) |
| DK (1) | DK0474696T3 (OSRAM) |
| ES (2) | ES2022799A6 (OSRAM) |
| GB (2) | GB8912456D0 (OSRAM) |
| IL (1) | IL94480A (OSRAM) |
| IN (1) | IN177062B (OSRAM) |
| NO (1) | NO302662B1 (OSRAM) |
| WO (1) | WO1990015092A1 (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9014647D0 (en) * | 1990-07-02 | 1993-06-02 | Secr Defence | Extrudable gun propellant composition |
| US5120827A (en) * | 1990-08-02 | 1992-06-09 | Thiokol Corporation | Process for producing improved poly(glycidyl nitrate) |
| ES2051227B1 (es) * | 1992-07-31 | 1994-12-16 | Espanola Explosivos | Procedimiento para la obtencion de un polimero poliglicidil p-toluensulfonato hidroxiterminado y su aplicacion en la sintesis de polimeros energeticos explosivos y fotosensibles. |
| FR2697256B1 (fr) * | 1992-10-23 | 1994-12-09 | Centre Nat Rech Scient | Polyéthers perfluoroalkylés hydroxylés, procédé de préparation et application à la synthèse de matériaux polyuréthanes. |
| US5426174A (en) * | 1992-12-08 | 1995-06-20 | Arco Chemical Technology, L.P. | Hydroxy-functionalized polyoxyalkylene ether compositions derived from mixtures of C4 epoxides |
| US5380777A (en) * | 1993-01-08 | 1995-01-10 | Thiokol Corporation | Polyglycidyl nitrate plasticizers |
| US5466759A (en) * | 1994-01-18 | 1995-11-14 | Eastman Chemical Company | Polyether glycols and alcohols derived from 3,4-epoxy-1-butene |
| EP1181937A3 (en) * | 1994-08-09 | 2004-02-04 | Cytrx Corporation | Novel vaccine adjuvant and vaccine |
| KR100364476B1 (ko) * | 1994-08-19 | 2003-01-24 | 데지마 테크 비.브이. | 액정폴리에테르 |
| US5587553A (en) * | 1994-11-07 | 1996-12-24 | Thiokol Corporation | High performance pressable explosive compositions |
| IL125013A0 (en) * | 1995-12-22 | 1999-01-26 | Akzo Nobel Nv | Liquid crystalline displays with a retardation layer |
| US6815522B1 (en) | 1998-11-12 | 2004-11-09 | Alliant Techsystems Inc. | Synthesis of energetic thermoplastic elastomers containing oligomeric urethane linkages |
| US7101955B1 (en) | 1998-11-12 | 2006-09-05 | Alliant Techsystems Inc. | Synthesis of energetic thermoplastic elastomers containing both polyoxirane and polyoxetane blocks |
| DE69911647T2 (de) * | 1998-11-12 | 2004-04-29 | Alliant Techsystems Inc., Edina | Herstellung von energetischen thermoplastischen elastomeren die sowohl polyoxiran- als polyoxetanblöcke enthalten |
| US6997997B1 (en) | 1998-11-12 | 2006-02-14 | Alliant Techsystems Inc. | Method for the synthesis of energetic thermoplastic elastomers in non-halogenated solvents |
| SE514207C2 (sv) | 1999-03-23 | 2001-01-22 | Perstorp Ab | Hyperförgrenad dendritisk polyeter och förfarande för framställning därav |
| WO2001029111A1 (en) | 1999-10-19 | 2001-04-26 | Alliant Techsystems Inc. | Polymerization of poly(glycidyl nitrate) from high purity glycidyl nitrate synthesized from glycerol |
| US7320848B2 (en) * | 2004-03-31 | 2008-01-22 | Samsung Electronics Co., Ltd. | Poly(azine)-based charge transport materials |
| US7534540B2 (en) | 2004-03-31 | 2009-05-19 | Samsung Electronics Co., Ltd. | Azine-based charge transport materials having two reactive rings |
| US8692030B1 (en) * | 2006-04-20 | 2014-04-08 | Pittsburg State University | Biobased-petrochemical hybrid polyols |
| JP5655281B2 (ja) * | 2008-06-10 | 2015-01-21 | 東ソー株式会社 | 塩素化ポリエーテル及びそれよりなるポリウレタン |
| US8030440B1 (en) * | 2010-05-21 | 2011-10-04 | Fluorochem, Inc. | Synthesis of poly-(3-nitratooxetane) |
| US9822088B2 (en) | 2011-03-30 | 2017-11-21 | The United States Of America As Represented By The Administrator Of Nasa | Anisotropic copoly(imide oxetane) coatings and articles of manufacture, copoly(imide oxetane)s containing pendant fluorocarbon moieties, oligomers and processes therefor |
| US9278374B2 (en) | 2012-06-08 | 2016-03-08 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Modified surface having low adhesion properties to mitigate insect residue adhesion |
| CN115975176A (zh) * | 2023-01-17 | 2023-04-18 | 广东粤港澳大湾区黄埔材料研究院 | 含异噁唑啉环的热塑性弹性体及其制备方法、应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3305565A (en) * | 1964-07-08 | 1967-02-21 | Shell Oil Co | Polyepihalohydrin preparation using fluoboric acid catalyst |
| US4110268A (en) * | 1976-09-27 | 1978-08-29 | Witco Chemical Corporation | Polyether polyols and polyurethane foams made therefrom |
| US4113785A (en) * | 1976-10-29 | 1978-09-12 | Basf Wyandotte Corporation | Polyether polyols and method of preparing same |
| US4393199A (en) * | 1981-05-12 | 1983-07-12 | S R I International | Cationic polymerization |
| US4806613A (en) * | 1988-03-29 | 1989-02-21 | Morton Thiokol, Inc. | Method of producing thermoplastic elastomers having alternate crystalline structure for use as binders in high-energy compositions |
-
1989
- 1989-05-31 GB GB898912456A patent/GB8912456D0/en active Pending
-
1990
- 1990-05-23 IL IL9448090A patent/IL94480A/en not_active IP Right Cessation
- 1990-05-25 IN IN508DE1990 patent/IN177062B/en unknown
- 1990-05-30 ES ES9001499A patent/ES2022799A6/es not_active Expired - Lifetime
- 1990-05-30 DK DK90908292.7T patent/DK0474696T3/da active
- 1990-05-30 US US07/820,692 patent/US5313000A/en not_active Expired - Lifetime
- 1990-05-30 AT AT90908292T patent/ATE145413T1/de not_active IP Right Cessation
- 1990-05-30 JP JP2508027A patent/JPH04505934A/ja active Pending
- 1990-05-30 WO PCT/GB1990/000837 patent/WO1990015092A1/en not_active Ceased
- 1990-05-30 EP EP90908292A patent/EP0474696B1/en not_active Expired - Lifetime
- 1990-05-30 DE DE69029196T patent/DE69029196T2/de not_active Expired - Fee Related
- 1990-05-30 AU AU57281/90A patent/AU635034B2/en not_active Ceased
- 1990-05-30 ES ES90908292T patent/ES2095253T3/es not_active Expired - Lifetime
- 1990-05-30 BR BR909007410A patent/BR9007410A/pt not_active IP Right Cessation
-
1991
- 1991-11-19 GB GB9124683A patent/GB2249314B/en not_active Expired - Fee Related
- 1991-11-21 NO NO914557A patent/NO302662B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2022799A6 (es) | 1991-12-01 |
| NO914557D0 (no) | 1991-11-21 |
| JPH04505934A (ja) | 1992-10-15 |
| NO914557L (no) | 1991-11-21 |
| DE69029196D1 (de) | 1997-01-02 |
| GB2249314B (en) | 1994-02-09 |
| BR9007410A (pt) | 1992-07-21 |
| AU635034B2 (en) | 1993-03-11 |
| AU5728190A (en) | 1991-01-07 |
| IN177062B (OSRAM) | 1996-10-26 |
| WO1990015092A1 (en) | 1990-12-13 |
| GB2249314A (en) | 1992-05-06 |
| DE69029196T2 (de) | 1997-05-15 |
| EP0474696A1 (en) | 1992-03-18 |
| DK0474696T3 (da) | 1996-12-09 |
| GB8912456D0 (en) | 1989-07-19 |
| EP0474696B1 (en) | 1996-11-20 |
| GB9124683D0 (en) | 1992-01-15 |
| US5313000A (en) | 1994-05-17 |
| ES2095253T3 (es) | 1997-02-16 |
| ATE145413T1 (de) | 1996-12-15 |
| NO302662B1 (no) | 1998-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| HP | Change in proprietorship | ||
| MM9K | Patent not in force due to non-payment of renewal fees |