CH453320A - Procédé de préparation de polyols - Google Patents
Procédé de préparation de polyolsInfo
- Publication number
- CH453320A CH453320A CH1382160A CH1382160A CH453320A CH 453320 A CH453320 A CH 453320A CH 1382160 A CH1382160 A CH 1382160A CH 1382160 A CH1382160 A CH 1382160A CH 453320 A CH453320 A CH 453320A
- Authority
- CH
- Switzerland
- Prior art keywords
- theory
- chloro
- reaction
- formula
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229920005862 polyol Polymers 0.000 title description 6
- 150000003077 polyols Chemical class 0.000 title description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- -1 phosphorus compound Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229920005830 Polyurethane Foam Polymers 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- 239000011496 polyurethane foam Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 235000011007 phosphoric acid Nutrition 0.000 description 17
- 239000006260 foam Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000002924 oxiranes Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000012086 standard solution Substances 0.000 description 4
- MKNQNPYGAQGARI-UHFFFAOYSA-N 4-(bromomethyl)phenol Chemical compound OC1=CC=C(CBr)C=C1 MKNQNPYGAQGARI-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 2
- SKCLYNFYASNQIL-UHFFFAOYSA-N 2-(chloromethyl)-2-ethyl-3-propyloxirane Chemical compound CCCC1OC1(CC)CCl SKCLYNFYASNQIL-UHFFFAOYSA-N 0.000 description 2
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KAKVFSYQVNHFBS-UHFFFAOYSA-N (5-hydroxycyclopenten-1-yl)-phenylmethanone Chemical compound OC1CCC=C1C(=O)C1=CC=CC=C1 KAKVFSYQVNHFBS-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- 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
- LECYALNHBVILEC-UHFFFAOYSA-N 2,3-bis(1-chlorobutyl)oxirane Chemical compound CCCC(Cl)C1OC1C(Cl)CCC LECYALNHBVILEC-UHFFFAOYSA-N 0.000 description 1
- TTYOZMIKBYZEGL-UHFFFAOYSA-N 2,3-bis(1-chloroethyl)oxirane Chemical compound CC(Cl)C1OC1C(C)Cl TTYOZMIKBYZEGL-UHFFFAOYSA-N 0.000 description 1
- ORKJOULYBCJKFT-UHFFFAOYSA-N 2,3-bis(1-chloropropyl)oxirane Chemical compound ClC(CC)C1C(C(CC)Cl)O1 ORKJOULYBCJKFT-UHFFFAOYSA-N 0.000 description 1
- STDUFFCKPIBQPO-UHFFFAOYSA-N 2-(1-chlorobutyl)-3-ethyloxirane Chemical compound ClC(C1C(CC)O1)CCC STDUFFCKPIBQPO-UHFFFAOYSA-N 0.000 description 1
- DQIZADWHMYXHGN-UHFFFAOYSA-N 2-(1-chlorobutyl)-3-propyloxirane Chemical compound ClC(C1C(CCC)O1)CCC DQIZADWHMYXHGN-UHFFFAOYSA-N 0.000 description 1
- RVWYSKJXNJEXQE-UHFFFAOYSA-N 2-(1-chloroethyl)-3-(1-chlorohexyl)oxirane Chemical compound ClC(C)C1C(C(CCCCC)Cl)O1 RVWYSKJXNJEXQE-UHFFFAOYSA-N 0.000 description 1
- LVZPWXWJBDPQNI-UHFFFAOYSA-N 2-(1-chloroethyl)-3-(1-chloropropyl)oxirane Chemical compound ClC(C)C1C(C(CC)Cl)O1 LVZPWXWJBDPQNI-UHFFFAOYSA-N 0.000 description 1
- NHAUMRVLSFBRBE-UHFFFAOYSA-N 2-(1-chloroethyl)-3-ethyloxirane Chemical compound CCC1OC1C(C)Cl NHAUMRVLSFBRBE-UHFFFAOYSA-N 0.000 description 1
- ZPENLTGGQAFXHN-UHFFFAOYSA-N 2-(1-chloroethyl)-3-methyloxirane Chemical compound CC(Cl)C1OC1C ZPENLTGGQAFXHN-UHFFFAOYSA-N 0.000 description 1
- VPCIBEXVZVMHNG-UHFFFAOYSA-N 2-(1-chloroethyl)-3-pentyloxirane Chemical compound ClC(C)C1C(CCCCC)O1 VPCIBEXVZVMHNG-UHFFFAOYSA-N 0.000 description 1
- ZATZNIFQGGUBOE-UHFFFAOYSA-N 2-(1-chloroethyl)-3-propyloxirane Chemical compound ClC(C)C1C(CCC)O1 ZATZNIFQGGUBOE-UHFFFAOYSA-N 0.000 description 1
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 1
- JSAPJQPHCHLOPE-UHFFFAOYSA-N 2-(1-chloropentyl)-3-methyloxirane Chemical compound ClC(C1C(C)O1)CCCC JSAPJQPHCHLOPE-UHFFFAOYSA-N 0.000 description 1
- BTWDUBZHKKGYSO-UHFFFAOYSA-N 2-(1-chloropropyl)-3-methyloxirane Chemical compound ClC(C1C(C)O1)CC BTWDUBZHKKGYSO-UHFFFAOYSA-N 0.000 description 1
- UPBIKILYCMODQW-UHFFFAOYSA-N 2-(1-chloropropyl)-3-pentyloxirane Chemical compound ClC(CC)C1C(CCCCC)O1 UPBIKILYCMODQW-UHFFFAOYSA-N 0.000 description 1
- SRXBOKMHGNRUSG-UHFFFAOYSA-N 2-(1-chloropropyl)-3-propyloxirane Chemical compound CCCC1OC1C(Cl)CC SRXBOKMHGNRUSG-UHFFFAOYSA-N 0.000 description 1
- DBHRMCNGNQOCNI-UHFFFAOYSA-N 2-(1-chloropropyl)oxirane Chemical compound CCC(Cl)C1CO1 DBHRMCNGNQOCNI-UHFFFAOYSA-N 0.000 description 1
- DBCILFBCLWASPY-UHFFFAOYSA-N 2-(2-chloroethenyl)oxirane Chemical compound ClC=CC1CO1 DBCILFBCLWASPY-UHFFFAOYSA-N 0.000 description 1
- JVRWLRWOCHNBOA-UHFFFAOYSA-N 2-(chloromethyl)-3-(1-chloropentyl)oxirane Chemical compound ClCC1C(C(CCCC)Cl)O1 JVRWLRWOCHNBOA-UHFFFAOYSA-N 0.000 description 1
- XSVIGJOAWHFBOP-UHFFFAOYSA-N 2-(chloromethyl)-3-(1-chloropropyl)oxirane Chemical compound ClCC1C(C(CC)Cl)O1 XSVIGJOAWHFBOP-UHFFFAOYSA-N 0.000 description 1
- JOJOMYICHZJKLN-UHFFFAOYSA-N 2-(chloromethyl)-3-heptyloxirane Chemical compound CCCCCCCC1OC1CCl JOJOMYICHZJKLN-UHFFFAOYSA-N 0.000 description 1
- MMTOSBCMFDNOIY-UHFFFAOYSA-N 2-(chloromethyl)-3-methyloxirane Chemical compound CC1OC1CCl MMTOSBCMFDNOIY-UHFFFAOYSA-N 0.000 description 1
- OHAIVJAXSTXMFQ-UHFFFAOYSA-N 2-(chloromethyl)-3-pentyloxirane Chemical compound CCCCCC1OC1CCl OHAIVJAXSTXMFQ-UHFFFAOYSA-N 0.000 description 1
- UEMRRMNEJABNGQ-UHFFFAOYSA-N 2-(chloromethyl)-3-propyloxirane Chemical compound CCCC1OC1CCl UEMRRMNEJABNGQ-UHFFFAOYSA-N 0.000 description 1
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- COHPEBVGRVKJKY-UHFFFAOYSA-N 2-butyl-3-(1-chlorobutyl)oxirane Chemical compound ClC(CCC)C1C(CCCC)O1 COHPEBVGRVKJKY-UHFFFAOYSA-N 0.000 description 1
- UVFWLQQAZYMJFB-UHFFFAOYSA-N 2-butyl-3-(1-chloroethyl)oxirane Chemical compound ClC(C)C1C(CCCC)O1 UVFWLQQAZYMJFB-UHFFFAOYSA-N 0.000 description 1
- XXCXJRVAQQMPLN-UHFFFAOYSA-N 2-butyl-3-(1-chloropropyl)oxirane Chemical compound CCCCC1OC1C(Cl)CC XXCXJRVAQQMPLN-UHFFFAOYSA-N 0.000 description 1
- MMJGNKUFFPODNG-UHFFFAOYSA-N 2-butyl-3-(chloromethyl)oxirane Chemical compound CCCCC1OC1CCl MMJGNKUFFPODNG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- QKYMMOMTGZGNAF-UHFFFAOYSA-N ClC(C)C1C(C(CCC)Cl)O1 Chemical compound ClC(C)C1C(C(CCC)Cl)O1 QKYMMOMTGZGNAF-UHFFFAOYSA-N 0.000 description 1
- QXCXKXNWODTYFX-UHFFFAOYSA-N ClC(C)C1C(CCCCCC)O1 Chemical compound ClC(C)C1C(CCCCCC)O1 QXCXKXNWODTYFX-UHFFFAOYSA-N 0.000 description 1
- JQESLVHQYLWCGN-UHFFFAOYSA-N ClC(C1C(C)O1)CCC Chemical compound ClC(C1C(C)O1)CCC JQESLVHQYLWCGN-UHFFFAOYSA-N 0.000 description 1
- ZVVZRHYEMABVRZ-UHFFFAOYSA-N ClC(C1C(C)O1)CCCCC Chemical compound ClC(C1C(C)O1)CCCCC ZVVZRHYEMABVRZ-UHFFFAOYSA-N 0.000 description 1
- YEEGLNPAVJHECH-UHFFFAOYSA-N ClC(C1C(CC)O1)CCCC Chemical compound ClC(C1C(CC)O1)CCCC YEEGLNPAVJHECH-UHFFFAOYSA-N 0.000 description 1
- LDGGSRLPRAHLBH-UHFFFAOYSA-N ClC(C1C(CC)O1)CCCCC Chemical compound ClC(C1C(CC)O1)CCCCC LDGGSRLPRAHLBH-UHFFFAOYSA-N 0.000 description 1
- AHAQERCMXHPIRR-UHFFFAOYSA-N ClC(C1C(CCC)O1)CCCC Chemical compound ClC(C1C(CCC)O1)CCCC AHAQERCMXHPIRR-UHFFFAOYSA-N 0.000 description 1
- OQJZONJARLODSA-UHFFFAOYSA-N ClC(CC)C1C(C(CCCC)Cl)O1 Chemical compound ClC(CC)C1C(C(CCCC)Cl)O1 OQJZONJARLODSA-UHFFFAOYSA-N 0.000 description 1
- XWHGDIRBGUOWBW-UHFFFAOYSA-N ClCC1C(C(CCCCC)Cl)O1 Chemical compound ClCC1C(C(CCCCC)Cl)O1 XWHGDIRBGUOWBW-UHFFFAOYSA-N 0.000 description 1
- YNPJKAKKSXIVGL-UHFFFAOYSA-N ClCC1C(C(CCCCCC)Cl)O1 Chemical compound ClCC1C(C(CCCCCC)Cl)O1 YNPJKAKKSXIVGL-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DWCZIOOZPIDHAB-UHFFFAOYSA-L methyl green Chemical compound [Cl-].[Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)[N+](C)(C)C)=C1C=CC(=[N+](C)C)C=C1 DWCZIOOZPIDHAB-UHFFFAOYSA-L 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
- C08G18/5078—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to hydrogen
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
- C08G18/5081—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/5084—Phosphate 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/6795—Unsaturated polyethers
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Epoxy Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US86034459A | 1959-12-18 | 1959-12-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH453320A true CH453320A (fr) | 1968-06-14 |
Family
ID=25333006
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1382160A CH453320A (fr) | 1959-12-18 | 1960-12-09 | Procédé de préparation de polyols |
Country Status (4)
Country | Link |
---|---|
CH (1) | CH453320A (es) |
DE (1) | DE1139478B (es) |
GB (1) | GB922198A (es) |
NL (1) | NL259180A (es) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1254150B (de) * | 1964-07-31 | 1967-11-16 | Walter Bloechl | Verfahren zur Herstellung von Fluoralkylphosphonsaeureglyzidylestern |
GB1115043A (en) * | 1964-08-06 | 1968-05-22 | Albright & Wilson Mfg Ltd | Polyesters having improved flame retardancy and the preparation thereof |
FR2269862B1 (es) * | 1974-03-08 | 1976-10-29 | Philagro Sa | |
CN106397475B (zh) * | 2016-08-18 | 2018-06-26 | 中国林业科学研究院林产化学工业研究所 | 一种植物油基多元醇及其制备方法和应用 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2610978A (en) * | 1949-12-02 | 1952-09-16 | Union Carbide & Carbon Corp | Production of halogen containing organic compounds of phosphorus |
FR1032240A (fr) * | 1950-11-27 | 1953-06-30 | Bougie d'allumage avec dispositif antiparasite | |
DE1032240B (de) * | 1956-12-19 | 1958-06-19 | Hoechst Ag | Verfahren zur Herstellung von organischen Phosphorsaeureestern durch Umsetzen von Phosphoroxychlorid oder Derivaten desselben mit Alkylenoxyden |
-
0
- NL NL259180D patent/NL259180A/xx unknown
-
1960
- 1960-12-02 GB GB4151160A patent/GB922198A/en not_active Expired
- 1960-12-09 CH CH1382160A patent/CH453320A/fr unknown
- 1960-12-17 DE DEU7660A patent/DE1139478B/de active Pending
Also Published As
Publication number | Publication date |
---|---|
GB922198A (en) | 1963-03-27 |
NL259180A (es) | |
DE1139478B (de) | 1962-11-15 |
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