US3839380A - Manganese-(ii)salts of phosphonic acid half-esters - Google Patents
Manganese-(ii)salts of phosphonic acid half-esters Download PDFInfo
- Publication number
- US3839380A US3839380A US00282636A US28263672A US3839380A US 3839380 A US3839380 A US 3839380A US 00282636 A US00282636 A US 00282636A US 28263672 A US28263672 A US 28263672A US 3839380 A US3839380 A US 3839380A
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- US
- United States
- Prior art keywords
- carbon atoms
- manganese
- salts
- anion
- formula
- Prior art date
- 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 - Lifetime
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- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical class [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 title description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title description 7
- 150000003839 salts Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 150000001450 anions Chemical class 0.000 abstract description 18
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 10
- -1 CYCLOHEXYL Chemical class 0.000 abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 7
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 239000011572 manganese Substances 0.000 description 16
- 239000004952 Polyamide Substances 0.000 description 13
- 229920002647 polyamide Polymers 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000012876 carrier material Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000002696 manganese Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 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 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- SPFXQZBXVCUHTR-UHFFFAOYSA-N P(O)(O)=O.OCC Chemical compound P(O)(O)=O.OCC SPFXQZBXVCUHTR-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical compound CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101000795350 Homo sapiens Tripartite motif-containing protein 59 Proteins 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000718541 Tetragastris balsamifera Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 102100029717 Tripartite motif-containing protein 59 Human genes 0.000 description 1
- YLVXPXINUWURSG-UHFFFAOYSA-N [hydroxy(phenyl)methyl]phosphonic acid Chemical compound OP(=O)(O)C(O)C1=CC=CC=C1 YLVXPXINUWURSG-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GJWAEWLHSDGBGG-UHFFFAOYSA-N hexylphosphonic acid Chemical compound CCCCCCP(O)(O)=O GJWAEWLHSDGBGG-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- 235000006748 manganese carbonate Nutrition 0.000 description 1
- 239000011656 manganese carbonate Substances 0.000 description 1
- IPJKJLXEVHOKSE-UHFFFAOYSA-L manganese dihydroxide Chemical compound [OH-].[OH-].[Mn+2] IPJKJLXEVHOKSE-UHFFFAOYSA-L 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
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- ZUUZGQPEQORUEV-UHFFFAOYSA-N tetrahydrate;hydrochloride Chemical compound O.O.O.O.Cl ZUUZGQPEQORUEV-UHFFFAOYSA-N 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
Definitions
- New manganese-(II) salts of phosphonic acid half-esters are used as stabilisers for polyamides.
- the new compounds are manufactured from the corresponding sodium salts of the phosphonic acid half-esters and a manganese- (II) salt.
- the subject of the invention are new manganese-(II) salts of phosphonic acid half-esters, their manufacture, their use for protecting polyamides and, as an industrial product, the organic material protected, with the aid of these salts, against the harmful influence of light.
- the salts concerned are the salts of the divalent manganese cation with anions of organic acids, for example acetate, oxalate, lactate and benzoate. They are added to the carrier material together with acids of phosphorus, either in the form of the corresponding sodium salts or as free acids or as their esters, such as sodium hexametaphosphate, phosphorous acid, phenyl phosphonic acid or esters thereof, before, during or after the polymerisation or polycondensation.
- R denotes alkyl with l to 18 carbon atoms, cyclohexyl, aryl with 6 to carbon atoms which is unsubstituted or substituted by 1 or 2 methyl groups or aralkyl with 7 to 11 carbon atoms
- A denotes the anion of an aliphatic carboxylic acid with 1 to 18 carbon atoms or of an aromatic carboxylic acid with 7 to 11 carbon atoms or the chloride, bromide or iodide anion
- x denotes 1 or 2
- y denotes 0 or 1 with x+y being 2
- R denotes alkyl with 1 to 18 carbon atoms
- the compounds according to the invention show a distinctly improved action as light stabilisers and'furthermore have the industrially desired advantage of a substantially lower ease of elution from the polyamide by aqueous media.
- the compounds according to the invention show a far better light protection action andsubstantially more favourable colour properties.
- R and R in the formula I denote, for example, methyl, ethyl, n-propyl, iso-propyl, butyl, pentyl, hexyl, octyl, iso-octyl, decyl, dodecyl, tetradecyl or octadecyl.
- R is preferably alkyl with 1 to 12 carbon atoms and particularly preferably alkyl with 2 to 12 and with 3 to 12 carbon atoms.
- R is preferably alkyl with 2-18 carbon atoms such as methyl, ethyl, propyl, butyl or octyl. Methyl, ethyl or butyl are particularly preferred.
- Aryl in the formula I denotes, for example, phenyl or naphthyl and aralkyl can denote benzyl, 2-phenylethyl or naphthylmethyl.
- the anion A in the formula I can be the anion of an aliphatic carboxylic acid with 1 to 18 carbon atoms, for example the anion of formic acid, acetic acid, propionic acid, butyric acid, 2-ethyl-hexanoic acid, lauric acid and stearic acid.
- the anion A can, however, also be the anion of an aromatic carboxylic acid with 7 to 11 carbon atoms, for example the anion of benzoic acid, of a toluic acid, of phenylacetic acid or of butylbenzoic acid.
- Anions of aliphatic carboxylic acids with 2 to 8 carbon atoms for example the acetate ion, or anions of aromatic carboxylic acids with 7 or 8 carbon atoms, for example the benzoate ion, are preferred as
- a Possible carrier materials for the-new compounds are polyamides and copolyamides which are obtained by polymerisation of diamines and dicarboxylic acids and/or of aminocarboxylic acids or the corresponding lactams.
- the substrates can be in the form of filaments, bristles, films, injection-moulded articles and the like.
- the compounds of the formula I are added to the carrier materials in an amount which corresponds to 1.0 to 500 p.p.m. of manganese, relative to the carrier material.
- Manganese additions of 10 to 200 ppm. relative to the carrier material are preferred, and those of 10 to 70 ppm. are particularly preferred.
- the new compounds can be incorporated into the polyamides before, during or after polyconden-sation, optionally conjointly with further additives.
- further additives are: pigments, mainly titanium dioxide in its two modifications rutile and anatase, in concentrations of 0.01-3.0%, but also coloured pigments such as sulphides, phthalocyanines, and perylene pigments; chain regulators, for example acetic acid and benzoic acid; phenolic antioxidants or amine antioxidants such as 1,3,5- trimethyl-2,4,6-tri-(3,5-di-tert.-butyl-4-hydroxy benzy1)- benzene, pentaerythritol-[3-(4-hydroxy-3,5-di-tert.
- butylphenyl)-propionic acidJ-tetraester 1,6 hex-amethylene- [3-(4-hydroxy-3,5-di-tert.-butylphenyl) propionic acid]- diamide, 4,4'-butylidene-bis'(3 methyl 6 tert.
- UV absorbers which are prefer-ably incorporated into the polymer after the p'olycondensation, for example 2-(2'-liydroxy-3',5'-ditertamyl-phenyl)-benzotriazole and 2-(2'-hydroxy 5'- methyl-phenyl)-benzotriazole; furtheradditives, such as antistatic agents and fiameproofing agents.
- the new compounds can also be added to the finished polyamide before or during shaping, for example by sprinkling (dry blending) onto dried granules or by applying a solution of the compounds according to the invention, and optionally further additives, to the polyamide and subsequently evaporating the solvent.
- the ter also partially precipitates I e d e manganese salt of the half es 21 313 has the meaning mdlcated un er th at the same time.
- removal of the sodium chloride w'th the It is, however, also possible to react 2 mols of a phos- 1s dlspainsed with and the Process 15 hon.c acid half ester of the formula Ha suspension.
- the filtrate or the resulting suspension is p 1 evaporated to dryness and the residue is extracted with 0 ORI the solvents mentioned in Column 3.
- the evaporated extract 1s subsequently sub ected to the further purifica- OH (Ha) tion described in Column 4 and is thereafter dried for 8 hours at a temperature of 60 C.
- Suitable solvents for these reactions are above all water, alcohols, especially methanol, ethanol and isopropanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, dioxane, tetrahydrofurane, acetonitrile and mixtures of these solvents.
- the reactions are advantageously carried out in an inert gas atmosphere, which can consist, for example, of nitrogen.
- Such mixtures obtained by the manufacturing processes described are also suitable for use as light stabilisers for polyamides.
- EXAMPLES 1 TO 3 (COMPARE TABLE I)
- EXAMPLES 4 TO 10 (COMPARE TABLE II) 0.1 mol of the phosphonic acid half-esters of Column 2, isolated as sodium salts, are dissolved in the type and amount of solvent indicated in Column 3 and a solution of 10.2 g. (0.0515 mol) of manganese-(H) chloride tetrahydrate in 50 ml. of the same solvent is added dropwise at 25 to 30 C. The precipitate thereby produced is filtered oif and eluted with the solvent mentioned until no further chloride ions are detectable in the filtrate. (Example 5 behaves differently in this working-up stage.
- the amount of Mn-II acetate corresponding to 50 p.p.m. of Mn was dissolved in water and this solution was uniformly dried onto highly delustred polyamide-6 granules (1.8% of TiO The dry sprinkle-coated mixture was then also spun by means of extruders to give den monofilaments which were stretched.
- np osp onate fromi Il]v ⁇ rampl1 ⁇ ah1 h -l 1..
- 90 80 70 60 3. 50 p.p.m.o n as up osp onate from Example 2 85 85 70 65 4. 50 p.p.m. of Mn as Mn phosphonate from Example 6 85 75 65 55 5. 50 p.p.m. of Mn as Mn phospho- 6 50nate iromflliilamplleisnilunfi..- 85 70 60 50 ..m.o nas np osp o- 11%; from Example 9 95 85 75 65 7. 50 p.p.m.
- A is selected from the group consisting of an anion of an aliphatic carboxylic acid with 1 to 18 carbon atoms, an anion of an aromatic carboxylic acid with 7 to 11 carbon atoms, and the chloride, bromide, and iodide anion;
- x 1 or 2
- y is 0 or 1, with x+y being 2, and
- R is alkyl with 1 to 18 carbon atoms.
- R is selected from the group consisting of alkyl with 1 to 18 carbon atoms, cyclohexyl, phenyl, benzyl and naphthylmethyl.
- R is selected from the group consisting of alkyl with 1 to 12 carbon atoms, phenyl and benzyl.
- R is selected from the group consisting of alkyl with 2 to 12 carbon atoms, phenyl and benzyl and R is alkyl with 2 to 18 carbon atoms.
- R is selected from the group consisting of alkyl with 3 to 12 carbon atoms and benzyl.
- a compound of claim 1 wherein A is selected from the group consisting of the anion of an aliphatic carboxylic acid with 2 to 8 carbon atoms, the anion of an aromatic carboxylic acid with 7 to 8 carbon atoms, the chloride, bromide and iodide anion and R is selected from the group consisting of methyl, ethyl, propyl, butyl and octyl.
- a compound of claim 1 wherein A is selected from the group consisting of the anion of acetic acid, the anion of stearic acid, the chloride anion, and the iodide anion, and R is selected from the group consisting of methyl, ethyl and butyl.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US440635A US3893973A (en) | 1971-09-30 | 1974-02-07 | Manganese-(II) salts of phosphonic acid half-esters, polyamide stabilizers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1421071A CH562282A5 (enrdf_load_stackoverflow) | 1971-09-30 | 1971-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3839380A true US3839380A (en) | 1974-10-01 |
Family
ID=4398858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00282636A Expired - Lifetime US3839380A (en) | 1971-09-30 | 1972-08-21 | Manganese-(ii)salts of phosphonic acid half-esters |
Country Status (12)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444930A (en) * | 1981-08-26 | 1984-04-24 | Ato Chimie | Fire-resistant synthetic resin composition containing a polycarbonate, a phosphorous fireproofing additive, and possibly other additives and/or fillers, and articles made from this composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6908892B2 (ja) * | 2016-02-01 | 2021-07-28 | 日産化学株式会社 | フェニルホスホン酸化合物の金属塩を含むポリアミド樹脂組成物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE621316A (enrdf_load_stackoverflow) * | ||||
| FR1464681A (fr) * | 1964-10-06 | 1967-01-06 | British Celanese | Polyamides stabilisés |
| IL29201A (en) * | 1967-01-16 | 1972-07-26 | Fmc Corp | Plant growth regulant compositions and method using phosphonic acid derivatives |
| CH508686A (de) * | 1970-10-20 | 1971-06-15 | Ciba Geigy Ag | Verwendung von Mangan(II)salzen von Dialkylhydroxybenzylphosphonsäure-Halbestern als Lichtschutzmittel für nichttextile Substrate aus Polyamiden |
-
0
- BE BE789440D patent/BE789440A/xx unknown
-
1971
- 1971-09-30 CH CH1421071A patent/CH562282A5/xx not_active IP Right Cessation
-
1972
- 1972-08-21 US US00282636A patent/US3839380A/en not_active Expired - Lifetime
- 1972-09-12 NL NL7212359A patent/NL7212359A/xx unknown
- 1972-09-26 CS CS653672A patent/CS158746B2/cs unknown
- 1972-09-26 DD DD165885A patent/DD104310A5/xx unknown
- 1972-09-27 DE DE19722247265 patent/DE2247265A1/de active Pending
- 1972-09-27 JP JP47096946A patent/JPS4843450A/ja active Pending
- 1972-09-29 FR FR7234614A patent/FR2154746B1/fr not_active Expired
- 1972-09-29 AT AT839072A patent/ATA839072A/de not_active Application Discontinuation
- 1972-09-29 GB GB4512672A patent/GB1369555A/en not_active Expired
- 1972-09-29 IT IT29903/72A patent/IT968469B/it active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444930A (en) * | 1981-08-26 | 1984-04-24 | Ato Chimie | Fire-resistant synthetic resin composition containing a polycarbonate, a phosphorous fireproofing additive, and possibly other additives and/or fillers, and articles made from this composition |
Also Published As
| Publication number | Publication date |
|---|---|
| IT968469B (it) | 1974-03-20 |
| DE2247265A1 (de) | 1973-04-05 |
| BE789440A (fr) | 1973-03-29 |
| ATA839072A (de) | 1975-05-15 |
| CS158746B2 (enrdf_load_stackoverflow) | 1974-11-25 |
| CH562282A5 (enrdf_load_stackoverflow) | 1975-05-30 |
| GB1369555A (en) | 1974-10-09 |
| JPS4843450A (enrdf_load_stackoverflow) | 1973-06-23 |
| FR2154746B1 (enrdf_load_stackoverflow) | 1974-10-04 |
| FR2154746A1 (enrdf_load_stackoverflow) | 1973-05-11 |
| NL7212359A (enrdf_load_stackoverflow) | 1973-04-03 |
| DD104310A5 (enrdf_load_stackoverflow) | 1974-03-05 |
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