CA1332428C - 1,4- a disubstituant-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes - Google Patents

1,4- a disubstituant-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes

Info

Publication number: CA1332428C
Authority: CA; Canada
Prior art keywords: tetrahydroxy; diphosphorinane; dioxide; flame; phosphine
Prior art date: 1988-03-28
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.): Expired - Fee Related

Application number

CA000616229A

Other languages

English (en)

Inventor

Allan James Robertson

James Bernard Gallivan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Cyanamid Canada Inc

Original Assignee

Cyanamid Canada Inc

Priority date (The priority date 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 date listed.)

1988-03-28

Filing date

1991-11-14

Publication date

1994-10-11

1988-03-28 Priority claimed from CA000562688A external-priority patent/CA1311496C/fr

1991-11-14 Application filed by Cyanamid Canada Inc filed Critical Cyanamid Canada Inc

1991-11-14 Priority to CA000616229A priority Critical patent/CA1332428C/fr

1994-10-11 Application granted granted Critical

1994-10-11 Publication of CA1332428C publication Critical patent/CA1332428C/fr

2008-03-28 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

-1 1,4-disubstituted-2,3,5,6-tetrahydroxy-1,4- diphosphorinanes Chemical class 0.000 title claims abstract description 30
150000001875 compounds Chemical class 0.000 claims abstract description 17
125000001424 substituent group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
125000005843 halogen group Chemical group 0.000 claims abstract 3
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 35
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 25
229940015043 glyoxal Drugs 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 14
239000000243 solution Substances 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 7
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
239000003063 flame retardant Substances 0.000 abstract description 12
239000000543 intermediate Substances 0.000 abstract description 2
150000003568 thioethers Chemical class 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
238000012360 testing method Methods 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
229920000642 polymer Polymers 0.000 description 15
238000002360 preparation method Methods 0.000 description 13
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
229920001155 polypropylene Polymers 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000004743 Polypropylene Substances 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
VXTFGYMINLXJPW-UHFFFAOYSA-N phosphinane Chemical class C1CCPCC1 VXTFGYMINLXJPW-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
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 5
239000004114 Ammonium polyphosphate Substances 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
235000019826 ammonium polyphosphate Nutrition 0.000 description 5
238000007906 compression Methods 0.000 description 5
230000006835 compression Effects 0.000 description 5
150000002019 disulfides Chemical class 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
239000011707 mineral Substances 0.000 description 5
229920002635 polyurethane Polymers 0.000 description 5
239000004814 polyurethane Substances 0.000 description 5
239000004408 titanium dioxide Substances 0.000 description 5
ZXEVTWRXGUXNFO-UHFFFAOYSA-N 1,4-bis(2-methylpropyl)-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound CC(C)CP1C(O)C(O)P(CC(C)C)C(O)C1O ZXEVTWRXGUXNFO-UHFFFAOYSA-N 0.000 description 4
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
229920001276 ammonium polyphosphate Polymers 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
238000005188 flotation Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
INYGPWGIFNQVLF-UHFFFAOYSA-N 1,2-dihydroxydiphosphinane-3,3-diol Chemical class OP1CCCC(O)(O)P1O INYGPWGIFNQVLF-UHFFFAOYSA-N 0.000 description 3
YOZVQHMOHWJWLP-UHFFFAOYSA-N 1,4-bis(2-phenylethyl)-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound OC1C(O)P(CCC=2C=CC=CC=2)C(O)C(O)P1CCC1=CC=CC=C1 YOZVQHMOHWJWLP-UHFFFAOYSA-N 0.000 description 3
UVWFERRWDXGAFK-UHFFFAOYSA-N 1,4-dicyclohexyl-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound OC1C(O)P(C2CCCCC2)C(O)C(O)P1C1CCCCC1 UVWFERRWDXGAFK-UHFFFAOYSA-N 0.000 description 3
QEBXELFIWPYSNM-UHFFFAOYSA-N 1,4-diphosphinane Chemical class C1CPCCP1 QEBXELFIWPYSNM-UHFFFAOYSA-N 0.000 description 3
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
235000006708 antioxidants Nutrition 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
229920000573 polyethylene Polymers 0.000 description 3
239000012265 solid product Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CBSVFWYGKQSEGR-UHFFFAOYSA-N 1,4-di(butan-2-yl)-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound CCC(C)P1C(O)C(O)P(C(C)CC)C(O)C1O CBSVFWYGKQSEGR-UHFFFAOYSA-N 0.000 description 2
FVFWWQNJORECTJ-UHFFFAOYSA-N 1,4-dioxo-1,4-dipropyl-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound CCCP1(=O)C(O)C(O)P(=O)(CCC)C(O)C1O FVFWWQNJORECTJ-UHFFFAOYSA-N 0.000 description 2
ARKBXPNQDZSABH-UHFFFAOYSA-N 1,4-diphosphinane-2,3,5,6-tetrol Chemical compound OC1PC(O)C(O)PC1O ARKBXPNQDZSABH-UHFFFAOYSA-N 0.000 description 2
JJXJWPDDBJXMNC-UHFFFAOYSA-N 1,4-dipropyl-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound CCCP1C(O)C(O)P(CCC)C(O)C1O JJXJWPDDBJXMNC-UHFFFAOYSA-N 0.000 description 2
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
229940095076 benzaldehyde Drugs 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000001143 conditioned effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000019256 formaldehyde Nutrition 0.000 description 2
238000009291 froth flotation Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000011133 lead Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NHHZTWSSUWVBQK-UHFFFAOYSA-N 1,4-bis(2,4,4-trimethylpentyl)-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound CC(C)(C)CC(C)CP1C(O)C(O)P(CC(C)CC(C)(C)C)C(O)C1O NHHZTWSSUWVBQK-UHFFFAOYSA-N 0.000 description 1
YLYUAJJICVNRHL-UHFFFAOYSA-N 1,4-bis(2-methylpropyl)-1,4-dioxo-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound CC(C)CP1(=O)C(O)C(O)P(=O)(CC(C)C)C(O)C1O YLYUAJJICVNRHL-UHFFFAOYSA-N 0.000 description 1
UPISIXQVVZXPCG-UHFFFAOYSA-N 1,4-bis(3-hydroxypropyl)-1,4-dioxo-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound OCCCP1(=O)C(O)C(O)P(=O)(CCCO)C(O)C1O UPISIXQVVZXPCG-UHFFFAOYSA-N 0.000 description 1
RUXIBVSZZNGSEO-UHFFFAOYSA-N 1,4-di(butan-2-yl)-1,4-bis(sulfanylidene)-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound CCC(C)P1(=S)C(O)C(O)P(=S)(C(C)CC)C(O)C1O RUXIBVSZZNGSEO-UHFFFAOYSA-N 0.000 description 1
SIYXAIONJXMVNJ-UHFFFAOYSA-N 1,4-dicyclohexyl-1,4-bis(sulfanylidene)-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound OC1C(O)P(=S)(C2CCCCC2)C(O)C(O)P1(=S)C1CCCCC1 SIYXAIONJXMVNJ-UHFFFAOYSA-N 0.000 description 1
SGJSCIJVIFSMTO-UHFFFAOYSA-N 1,4-dihexyl-1,4-bis(sulfanylidene)-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound CCCCCCP1(=S)C(O)C(O)P(=S)(CCCCCC)C(O)C1O SGJSCIJVIFSMTO-UHFFFAOYSA-N 0.000 description 1
GGHZJFQWQRHJJT-UHFFFAOYSA-N 1,4-dihexyl-1,4-dioxo-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound CCCCCCP1(=O)C(O)C(O)P(=O)(CCCCCC)C(O)C1O GGHZJFQWQRHJJT-UHFFFAOYSA-N 0.000 description 1
MBVVKHKTUSGLIY-UHFFFAOYSA-N 1,4-dihexyl-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound CCCCCCP1C(O)C(O)P(CCCCCC)C(O)C1O MBVVKHKTUSGLIY-UHFFFAOYSA-N 0.000 description 1
KZBHLGXZSDBPJT-UHFFFAOYSA-N 1,4-dinaphthalen-1-yl-1,4-bis(sulfanylidene)-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound C1=CC=C2C(P3(=S)C(O)C(P(C(O)C3O)(=S)C=3C4=CC=CC=C4C=CC=3)O)=CC=CC2=C1 KZBHLGXZSDBPJT-UHFFFAOYSA-N 0.000 description 1
CEXLSNMVQORSRJ-UHFFFAOYSA-N 1,4-dinaphthalen-1-yl-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound C1=CC=C2C(P3C(O)C(P(C(O)C3O)C=3C4=CC=CC=C4C=CC=3)O)=CC=CC2=C1 CEXLSNMVQORSRJ-UHFFFAOYSA-N 0.000 description 1
OOITZMSYLVTSSJ-UHFFFAOYSA-N 1,4-dioctyl-1,4-bis(sulfanylidene)-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound CCCCCCCCP1(=S)C(O)C(O)P(=S)(CCCCCCCC)C(O)C1O OOITZMSYLVTSSJ-UHFFFAOYSA-N 0.000 description 1
PNVVWDRWEJCRMO-UHFFFAOYSA-N 1,4-dioctyl-1,4-dioxo-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound CCCCCCCCP1(=O)C(O)C(O)P(=O)(CCCCCCCC)C(O)C1O PNVVWDRWEJCRMO-UHFFFAOYSA-N 0.000 description 1
DZZVPWYLLSFEEF-UHFFFAOYSA-N 1,4-dioctyl-1,4-diphosphinane-2,3,5,6-tetrol Chemical compound CCCCCCCCP1C(O)C(O)P(CCCCCCCC)C(O)C1O DZZVPWYLLSFEEF-UHFFFAOYSA-N 0.000 description 1
HQKGBPXMCIUEJS-UHFFFAOYSA-N 1,4-dioxo-1,4-bis(2,4,4-trimethylpentyl)-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound CC(C)(C)CC(C)CP1(=O)C(O)C(O)P(=O)(CC(C)CC(C)(C)C)C(O)C1O HQKGBPXMCIUEJS-UHFFFAOYSA-N 0.000 description 1
SOQIPMZIYUGYAW-UHFFFAOYSA-N 1,4-dioxo-1,4-diphenyl-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound OC1C(O)P(=O)(C=2C=CC=CC=2)C(O)C(O)P1(=O)C1=CC=CC=C1 SOQIPMZIYUGYAW-UHFFFAOYSA-N 0.000 description 1
GOBYFXXKERHDIH-UHFFFAOYSA-N 1,4-diphenyl-1,4-bis(sulfanylidene)-1$l^{5},4$l^{5}-diphosphinane-2,3,5,6-tetrol Chemical compound OC1C(O)P(=S)(C=2C=CC=CC=2)C(O)C(O)P1(=S)C1=CC=CC=C1 GOBYFXXKERHDIH-UHFFFAOYSA-N 0.000 description 1
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YETUHERDTLGVDC-UHFFFAOYSA-N 3-[4-(2-cyanoethyl)-2,3,5,6-tetrahydroxy-1,4-dioxo-1$l^{5},4$l^{5}-diphosphinan-1-yl]propanenitrile Chemical compound OC1C(O)P(=O)(CCC#N)C(O)C(O)P1(=O)CCC#N YETUHERDTLGVDC-UHFFFAOYSA-N 0.000 description 1
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125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
101100305864 Alteromonas mediterranea (strain DSM 17117 / CIP 110805 / LMG 28347 / Deep ecotype) rph2 gene Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
LCWBNZACUUZRCN-UHFFFAOYSA-N ClP1(C(C(P(C(C1O)O)C1=CC=C(C=C1)Cl)(O)C1=CC=CC=C1)O)C1=CC=C(C=C1)Cl Chemical compound ClP1(C(C(P(C(C1O)O)C1=CC=C(C=C1)Cl)(O)C1=CC=CC=C1)O)C1=CC=C(C=C1)Cl LCWBNZACUUZRCN-UHFFFAOYSA-N 0.000 description 1
229910017518 Cu Zn Inorganic materials 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
235000009781 Myrtillocactus geometrizans Nutrition 0.000 description 1
240000009125 Myrtillocactus geometrizans Species 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000018734 Sambucus australis Nutrition 0.000 description 1
244000180577 Sambucus australis Species 0.000 description 1
101100135363 Yarrowia lipolytica (strain CLIB 122 / E 150) RIM101 gene Proteins 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
239000004202 carbamide Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
ZBCKWHYWPLHBOK-UHFFFAOYSA-N cyclohexylphosphane Chemical compound PC1CCCCC1 ZBCKWHYWPLHBOK-UHFFFAOYSA-N 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000008396 flotation agent Substances 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
238000000227 grinding Methods 0.000 description 1
CHXARDKIHSVFDK-UHFFFAOYSA-N hexylphosphane Chemical compound CCCCCCP CHXARDKIHSVFDK-UHFFFAOYSA-N 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004890 malting Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical class O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
238000005065 mining Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
SWMBQMGPRYJSCI-UHFFFAOYSA-N octylphosphane Chemical compound CCCCCCCCP SWMBQMGPRYJSCI-UHFFFAOYSA-N 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
RDBMUARQWLPMNW-UHFFFAOYSA-N phosphanylmethanol Chemical class OCP RDBMUARQWLPMNW-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920006380 polyphenylene oxide Polymers 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D1/00—Flotation
- B03D1/001—Flotation agents
- B03D1/004—Organic compounds
- B03D1/014—Organic compounds containing 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)

CA000616229A 1988-03-28 1991-11-14 1,4- a disubstituant-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes Expired - Fee Related CA1332428C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000616229A CA1332428C (fr)	1988-03-28	1991-11-14	1,4- a disubstituant-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA000562688A CA1311496C (fr)	1988-03-28	1988-03-28	2,3,5,6-tetrahydroxyl-1,4-diphosphorinanes disubstituees en 1,4 et leurs oxydes ou sulfures
CA000616229A CA1332428C (fr)	1988-03-28	1991-11-14	1,4- a disubstituant-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000562688A Division CA1311496C (fr)	1988-03-28	1988-03-28	2,3,5,6-tetrahydroxyl-1,4-diphosphorinanes disubstituees en 1,4 et leurs oxydes ou sulfures

Publications (1)

Publication Number	Publication Date
CA1332428C true CA1332428C (fr)	1994-10-11

Family

ID=25671800

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616229A Expired - Fee Related CA1332428C (fr)	1988-03-28	1991-11-14	1,4- a disubstituant-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes

Country Status (1)

Country	Link
CA (1)	CA1332428C (fr)

1991
- 1991-11-14 CA CA000616229A patent/CA1332428C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2004-10-12	MKLA	Lapsed

Publication	Publication Date	Title
US4855507A (en)	1989-08-08	1,4-Disubstituted-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes and their oxides or sulfides
US4278587A (en)	1981-07-14	Vulcanizable rubber mixture based on halogen free rubber for vulcanizing these rubber mixtures and use of the rubber mixtures
CA1275530C (fr)	1990-10-23	Melanges a base de tris-organophosphite a stabilite hydrolytique amelioree
US3997505A (en)	1976-12-14	Flame retardant polymeric compositions containing pentaerythritol cyclic diphosphates or diphosphoramidates
CA2080288A1 (fr)	1993-04-12	Sels de composes triaziniques avec des oxacides de phosphore, et emploi de ces composes dans des compositions polymeriques qui s'eteignent d'elles memes
US4830739A (en)	1989-05-16	Process and composition for the froth flotation beneficiation of iron minerals from iron ores
PL203935B1 (pl)	2009-11-30	Zbieracz do rud siarczkowych
EP0530874B1 (fr)	1999-12-22	Nouveaux phosphonates de pentaerythryle et leur utilisation dans des compositions auto-ignifugeantes de polymères thermoplastiques
IT9021421A1 (it)	1992-03-11	Composizioni polimeriche autoestinguenti.
IT9020919A1 (it)	1992-01-11	Sali di composti triazinici con acidi ossigenati del fosforo e loro impiego in composizioni polimeriche autoestinguenti
US5037533A (en)	1991-08-06	Ore flotation process and use of phosphorus containing sulfo compounds
US5149878A (en)	1992-09-22	1,4-disubstituted-2,3,5,6-tetrahyddroxy-1,4-diphosphorinanes and their oxides or sulfides
CA2062767A1 (fr)	1991-12-16	Procede de flottation utilisant un ensemble de reactifs
US6531539B2 (en)	2003-03-11	Organosilicon compounds
CA1332428C (fr)	1994-10-11	1,4- a disubstituant-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes
US5077437A (en)	1991-12-31	1,4-disubstituted-2,3,5,6-tetrahydroxy-1,4-diphosphorinane and their oxides or sulfides
US3978167A (en)	1976-08-31	Pentaerythritol cyclic diphosphates and diphosphoramidates
US4968416A (en)	1990-11-06	1,4-disubstituted-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes and their oxides or sulfides and their use in froth flotation
EP0684250B1 (fr)	2000-09-27	Poly(pentaerythrityldiphosphonate) et son utilisation dans des compositions autoextinctrices
CA1262792A (fr)	1989-11-07	Compositions a base de penta-erythrol-spiro-bis- phosphite ayant une stabilite hydrolytique amelioree
DE10353063A1 (de)	2005-06-23	Verfahren zur Herstellung von Amino-Gruppen tragenden Siliciumverbindungen
EP0054742A2 (fr)	1982-06-30	Compositions de chlorure de polyvinyle contenant du trizinc dimolybdate monohydrate et un phosphate de zinc pour la suppression de la fumée
DE2601363C3 (de)	1979-03-01	Feuerhemmende Formmassen
EP0547714B1 (fr)	1996-11-06	Acides triazinylphosphoniques et leur utilisation dans des compositions polymériques auto-ignifugeante
US4530758A (en)	1985-07-23	Ore flotation method