CA1075848A - Nouveaux composes contenant du phosphore - Google Patents

Nouveaux composes contenant du phosphore

Info

Publication number: CA1075848A
Authority: CA; Canada
Prior art keywords: group; phosphorus; ester; acid; reaction
Prior art date: 1975-10-14
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

Application number

CA323,655A

Other languages

English (en)

Inventor

Takao Kashihara

Seiji Endo

Tadashi Ikegami

Tatsuhiko Shizuki

Akitada Osako

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.)

Toyobo Co Ltd

Original Assignee

Toyobo Co Ltd

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.)

1975-10-14

Filing date

1979-03-16

Publication date

1980-04-15

1975-10-14 Priority claimed from JP12416475A external-priority patent/JPS5247891A/ja

1976-01-23 Priority claimed from JP51006924A external-priority patent/JPS582240B2/ja

1976-02-13 Priority claimed from JP1509076A external-priority patent/JPS5922717B2/ja

1976-02-13 Priority claimed from JP1508876A external-priority patent/JPS5298395A/ja

1976-10-14 Priority claimed from CA263,391A external-priority patent/CA1077499A/fr

1979-03-16 Application filed by Toyobo Co Ltd filed Critical Toyobo Co Ltd

1979-03-16 Priority to CA323,655A priority Critical patent/CA1075848A/fr

1980-04-15 Application granted granted Critical

1980-04-15 Publication of CA1075848A publication Critical patent/CA1075848A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 69
229910052698 phosphorus Inorganic materials 0.000 title claims description 84
239000011574 phosphorus Substances 0.000 title claims description 80
239000003063 flame retardant Substances 0.000 claims abstract description 46
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 80
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 64
229920000728 polyester Polymers 0.000 claims description 54
-1 alkylene glycols Chemical class 0.000 claims description 40
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 claims description 30
239000002253 acid Substances 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 15
150000002009 diols Chemical class 0.000 claims description 14
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 6
125000000524 functional group Chemical group 0.000 claims description 5
125000004437 phosphorous atom Chemical group 0.000 claims description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
125000001118 alkylidene group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 51
238000006116 polymerization reaction Methods 0.000 abstract description 7
229910052739 hydrogen Inorganic materials 0.000 abstract description 5
239000001257 hydrogen Substances 0.000 abstract 2
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
150000002431 hydrogen Chemical group 0.000 abstract 1
235000014786 phosphorus Nutrition 0.000 description 77
229920000642 polymer Polymers 0.000 description 34
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 30
238000002360 preparation method Methods 0.000 description 28
239000007788 liquid Substances 0.000 description 25
239000000243 solution Substances 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 21
238000000034 method Methods 0.000 description 20
239000000203 mixture Substances 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 18
238000005809 transesterification reaction Methods 0.000 description 18
HGAZJKGZTZTKCO-UHFFFAOYSA-N C12=CC=CC=C2OP(=O)=C2C1=CCCC2 Chemical compound C12=CC=CC=C2OP(=O)=C2C1=CCCC2 HGAZJKGZTZTKCO-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 16
238000010521 absorption reaction Methods 0.000 description 15
230000009102 absorption Effects 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 14
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
150000003018 phosphorus compounds Chemical class 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
235000019441 ethanol Nutrition 0.000 description 10
239000000835 fiber Substances 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
238000000921 elemental analysis Methods 0.000 description 9
239000000126 substance Substances 0.000 description 9
238000000862 absorption spectrum Methods 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 7
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 7
238000005886 esterification reaction Methods 0.000 description 7
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000004246 zinc acetate Substances 0.000 description 7
229960000314 zinc acetate Drugs 0.000 description 7
235000013904 zinc acetate Nutrition 0.000 description 7
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
GKMXREIWPASRMP-UHFFFAOYSA-J dipotassium;oxalate;oxygen(2-);titanium(4+) Chemical compound [O-2].[K+].[K+].[Ti+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O GKMXREIWPASRMP-UHFFFAOYSA-J 0.000 description 6
230000032050 esterification Effects 0.000 description 6
150000002430 hydrocarbons Chemical group 0.000 description 6
238000007127 saponification reaction Methods 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
150000001555 benzenes Chemical group 0.000 description 5
ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000008188 pellet Substances 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
238000006068 polycondensation reaction Methods 0.000 description 5
230000036647 reaction Effects 0.000 description 5
239000000460 chlorine Substances 0.000 description 4
150000001991 dicarboxylic acids Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
150000002605 large molecules Chemical class 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000007334 copolymerization reaction Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000003007 phosphonic acid derivatives Chemical class 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000009987 spinning Methods 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
125000000732 arylene group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
150000007942 carboxylates Chemical group 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
230000000332 continued effect Effects 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
239000007789 gas Substances 0.000 description 2
YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000001771 impaired effect Effects 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
239000010936 titanium Substances 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
PNXPXUDJXYVOFM-UHFFFAOYSA-N 2,3,5,6-tetrabromoterephthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(C(O)=O)C(Br)=C1Br PNXPXUDJXYVOFM-UHFFFAOYSA-N 0.000 description 1
XUKQTRYCLLDCIG-UHFFFAOYSA-N 2-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)butanedioic acid Chemical compound C1=CC=C2P(C(C(O)=O)CC(=O)O)(=O)OC3=CC=CC=C3C2=C1 XUKQTRYCLLDCIG-UHFFFAOYSA-N 0.000 description 1
BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
RVHUMFJSCJBNGS-UHFFFAOYSA-N 2-[2,6-dibromo-4-[2-[3,5-dibromo-4-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C(Br)=C(OCCO)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(OCCO)C(Br)=C1 RVHUMFJSCJBNGS-UHFFFAOYSA-N 0.000 description 1
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
QLIQIXIBZLTPGQ-UHFFFAOYSA-N 4-(2-hydroxyethoxy)benzoic acid Chemical compound OCCOC1=CC=C(C(O)=O)C=C1 QLIQIXIBZLTPGQ-UHFFFAOYSA-N 0.000 description 1
VAXBLYWAVAIJJJ-UHFFFAOYSA-N 4-[2-(4-carboxyphenoxy)ethoxy]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCCOC1=CC=C(C(O)=O)C=C1 VAXBLYWAVAIJJJ-UHFFFAOYSA-N 0.000 description 1
XKACUVXWRVMXOE-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)(C)C1=CC=C(C(O)=O)C=C1 XKACUVXWRVMXOE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
241000219498 Alnus glutinosa Species 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
WMRCEKCVYADHNG-UHFFFAOYSA-N CC(C)(C)c1ccc2-c3cc(cc(c3OP(=O)c2c1)C(C)(C)C)C(C)(C)C Chemical compound CC(C)(C)c1ccc2-c3cc(cc(c3OP(=O)c2c1)C(C)(C)C)C(C)(C)C WMRCEKCVYADHNG-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical class OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
241000193803 Therea Species 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
ITMIAZBRRZANGB-UHFFFAOYSA-N but-3-ene-1,2-diol Chemical compound OCC(O)C=C ITMIAZBRRZANGB-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
229940018557 citraconic acid Drugs 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000001514 detection method Methods 0.000 description 1
MRSOZKFBMQILFT-UHFFFAOYSA-L diazanium;oxalate;titanium(2+) Chemical compound [NH4+].[NH4+].[Ti+2].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O MRSOZKFBMQILFT-UHFFFAOYSA-L 0.000 description 1
VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 1
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
229960001826 dimethylphthalate Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229940119177 germanium dioxide Drugs 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 description 1
229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940071125 manganese acetate Drugs 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002074 melt spinning Methods 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000012856 packing Methods 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1

Landscapes

Polyesters Or Polycarbonates (AREA)

CA323,655A 1975-10-14 1979-03-16 Nouveaux composes contenant du phosphore Expired CA1075848A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA323,655A CA1075848A (fr)	1975-10-14	1979-03-16	Nouveaux composes contenant du phosphore

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP12416475A JPS5247891A (en)	1975-10-14	1975-10-14	Phosphorus-containing flame retarders
JP51006924A JPS582240B2 (ja)	1976-01-23	1976-01-23	新規含リン化合物
JP1509076A JPS5922717B2 (ja)	1976-02-13	1976-02-13	新規な有機リン化合物
JP1508876A JPS5298395A (en)	1976-02-13	1976-02-13	Phosphorus-containing incombustible agent
CA263,391A CA1077499A (fr)	1975-10-14	1976-10-14	Composes a teneur de phosphore
CA323,655A CA1075848A (fr)	1975-10-14	1979-03-16	Nouveaux composes contenant du phosphore

Publications (1)

Publication Number	Publication Date
CA1075848A true CA1075848A (fr)	1980-04-15

Family

ID=27543284

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA323,655A Expired CA1075848A (fr)	1975-10-14	1979-03-16	Nouveaux composes contenant du phosphore

Country Status (1)

Country	Link
CA (1)	CA1075848A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111995747A (zh) *	2020-09-15	2020-11-27	湖北省兴发磷化工研究院有限公司	一种聚酰胺用反应型阻燃剂的制备方法及其应用

1979
- 1979-03-16 CA CA323,655A patent/CA1075848A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111995747A (zh) *	2020-09-15	2020-11-27	湖北省兴发磷化工研究院有限公司	一种聚酰胺用反应型阻燃剂的制备方法及其应用
CN111995747B (zh) *	2020-09-15	2022-12-02	湖北省兴发磷化工研究院有限公司	一种聚酰胺用反应型阻燃剂的制备方法及其应用

Legal Events

Date	Code	Title	Description
1997-04-15	MKEX	Expiry

Publication	Publication Date	Title
CA1077499A (fr)	1980-05-13	Composes a teneur de phosphore
US4157436A (en)	1979-06-05	Phosphorus-containing polyesters
US3794617A (en)	1974-02-26	Copolyester fiber compositions having improved flame retardant properties
US5750635A (en)	1998-05-12	Thermally stable polyesters formed utilizing antimony compounds as catalysts
US4087408A (en)	1978-05-02	Bromine and phosphorus containing polyester
US5003029A (en)	1991-03-26	Flame resistant polyester from di aryl-di(hydroxyalkylene oxy)aryl phosphine oxide
EP0092868B1 (fr)	1986-01-22	Polyester linéaire ignifuge, procédé pour sa préparation et objets formés à partir dudit polyester
CA1075848A (fr)	1980-04-15	Nouveaux composes contenant du phosphore
US4940772A (en)	1990-07-10	Process for producing flame resistant polyester
US4101517A (en)	1978-07-18	Preparation of polyesters of 1,2-bis(hydroxyphenyl)ethanes and aromatic dicarboxylic acids
JP2003012781A (ja)	2003-01-15	ポリブチレンテレフタレート樹脂及び成形品
US3997511A (en)	1976-12-14	Unsaturated linear polyesters
KR100867196B1 (ko)	2008-11-06	난연 및 염기성 가염 폴리에스테르 섬유의 제조방법
US3887523A (en)	1975-06-03	Fiber-forming copolyester compositions from brominated ethoxylated hydroquinone
GB1569296A (en)	1980-06-11	Polymer compositions and their preparation
US4043981A (en)	1977-08-23	Copolyesters derived from ethoxylated 3,5-dibromo-4-hydroxybenzoic acid
US3997510A (en)	1976-12-14	Flame-resistant, thermoplastic polyesters
US3525715A (en)	1970-08-25	Cross-linked copolyesters and process of making them
JPH04364196A (ja)	1992-12-16	ホスフィン酸誘導体からなる反応性難燃剤およびこの誘導体の製法
JPH0248587B2 (fr)	1990-10-25
KR790001137B1 (ko)	1979-09-04	신규함인(含燐)화합물의 제조법
US5500285A (en)	1996-03-19	Reactive flame retardant additives containing phosphino oxide moieties
US4454302A (en)	1984-06-12	Polyester resin composition
US4034018A (en)	1977-07-05	Linear polyesters based on s-triazinedicarboxylic acids
KR830000059B1 (ko)	1983-02-05	내염성(耐炎性)폴리에스테르의 제조방법