JP4204792B2 - ラジカル重合性化合物の金属塩の製造方法 - Google Patents
ラジカル重合性化合物の金属塩の製造方法 Download PDFInfo
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- JP4204792B2 JP4204792B2 JP2002040904A JP2002040904A JP4204792B2 JP 4204792 B2 JP4204792 B2 JP 4204792B2 JP 2002040904 A JP2002040904 A JP 2002040904A JP 2002040904 A JP2002040904 A JP 2002040904A JP 4204792 B2 JP4204792 B2 JP 4204792B2
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- Prior art keywords
- water
- metal salt
- group
- polymerizable compound
- general 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 - Fee Related
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 58
- 150000003839 salts Chemical class 0.000 title claims abstract description 34
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 22
- 239000002184 metal Substances 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000007864 aqueous solution Substances 0.000 claims abstract description 27
- -1 alkali-metal salt Chemical class 0.000 claims abstract description 25
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 13
- 150000003751 zinc Chemical class 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 12
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000002211 L-ascorbic acid Substances 0.000 claims description 10
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 10
- 229960005070 ascorbic acid Drugs 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 230000018044 dehydration Effects 0.000 claims description 10
- 238000006297 dehydration reaction Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 claims description 5
- MNDTVJMRXYKBPV-UHFFFAOYSA-N 4-amino-2,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(N)=CC(C(C)(C)C)=C1O MNDTVJMRXYKBPV-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 235000010352 sodium erythorbate Nutrition 0.000 claims description 4
- 239000004320 sodium erythorbate Substances 0.000 claims description 4
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 4
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims description 3
- 235000010350 erythorbic acid Nutrition 0.000 claims description 3
- 239000004318 erythorbic acid Substances 0.000 claims description 3
- 229940026239 isoascorbic acid Drugs 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 235000019187 sodium-L-ascorbate Nutrition 0.000 claims description 2
- 239000011755 sodium-L-ascorbate Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- LCQXXVFFJHBYME-UHFFFAOYSA-N 2-butyl-4-hydroxybenzoic acid Chemical compound CCCCC1=CC(O)=CC=C1C(O)=O LCQXXVFFJHBYME-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 15
- 238000004821 distillation Methods 0.000 abstract 1
- LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 7
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 6
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 6
- 229930003268 Vitamin C Natural products 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 235000019154 vitamin C Nutrition 0.000 description 6
- 239000011718 vitamin C Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 2
- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- DWLAVVBOGOXHNH-UHFFFAOYSA-L magnesium;prop-2-enoate Chemical compound [Mg+2].[O-]C(=O)C=C.[O-]C(=O)C=C DWLAVVBOGOXHNH-UHFFFAOYSA-L 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 229940047670 sodium acrylate Drugs 0.000 description 2
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- BMFMTNROJASFBW-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfinyl)acetic acid Chemical compound OC(=O)CS(=O)CC1=CC=CO1 BMFMTNROJASFBW-UHFFFAOYSA-N 0.000 description 1
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 description 1
- ZUIMNFHCXYKWGT-UHFFFAOYSA-N 4-amino-2,6-ditert-butylphenol;hydrochloride Chemical compound Cl.CC(C)(C)C1=CC(N)=CC(C(C)(C)C)=C1O ZUIMNFHCXYKWGT-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- FPCWKNLZGKFYTL-RWUXNGIBSA-L calcium;(e)-3-phenylprop-2-enoate Chemical compound [Ca+2].[O-]C(=O)\C=C\C1=CC=CC=C1.[O-]C(=O)\C=C\C1=CC=CC=C1 FPCWKNLZGKFYTL-RWUXNGIBSA-L 0.000 description 1
- OAKHANKSRIPFCE-UHFFFAOYSA-L calcium;2-methylprop-2-enoate Chemical compound [Ca+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O OAKHANKSRIPFCE-UHFFFAOYSA-L 0.000 description 1
- TXTCTCUXLQYGLA-UHFFFAOYSA-L calcium;prop-2-enoate Chemical compound [Ca+2].[O-]C(=O)C=C.[O-]C(=O)C=C TXTCTCUXLQYGLA-UHFFFAOYSA-L 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GRMAAWAXJPMSLR-UHFFFAOYSA-N hydroxy(phenyl)azanium;chloride Chemical compound Cl.ONC1=CC=CC=C1 GRMAAWAXJPMSLR-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DZBOAIYHPIPCBP-UHFFFAOYSA-L magnesium;2-methylprop-2-enoate Chemical compound [Mg+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O DZBOAIYHPIPCBP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- OBRRLBBTAKVBRN-UHFFFAOYSA-M potassium;2-ethenylbenzenesulfonate Chemical compound [K+].[O-]S(=O)(=O)C1=CC=CC=C1C=C OBRRLBBTAKVBRN-UHFFFAOYSA-M 0.000 description 1
- HWDDJFFLFNQAFQ-UHFFFAOYSA-M potassium;4-ethenylbenzenesulfonate Chemical compound [K+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 HWDDJFFLFNQAFQ-UHFFFAOYSA-M 0.000 description 1
- RMHHXELLJFQJRG-UHFFFAOYSA-M potassium;4-ethenylbenzoate Chemical compound [K+].[O-]C(=O)C1=CC=C(C=C)C=C1 RMHHXELLJFQJRG-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- DXIHILNWDOYYCH-UHDJGPCESA-M sodium;(e)-3-phenylprop-2-enoate Chemical compound [Na+].[O-]C(=O)\C=C\C1=CC=CC=C1 DXIHILNWDOYYCH-UHDJGPCESA-M 0.000 description 1
- XESUCHPMWXMNRV-UHFFFAOYSA-M sodium;2-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1C=C XESUCHPMWXMNRV-UHFFFAOYSA-M 0.000 description 1
- ZPAICLPTNKAJHB-UHFFFAOYSA-M sodium;4-ethenylbenzoate Chemical compound [Na+].[O-]C(=O)C1=CC=C(C=C)C=C1 ZPAICLPTNKAJHB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002040904A JP4204792B2 (ja) | 2002-02-19 | 2002-02-19 | ラジカル重合性化合物の金属塩の製造方法 |
| EP03703349A EP1477470B1 (en) | 2002-02-19 | 2003-02-19 | Process for the production of metal salts of radical-polymerizable compounds |
| US10/501,118 US7183427B2 (en) | 2002-02-19 | 2003-02-19 | Process for the production of metal salts of radical-polymerizable compounds |
| PCT/JP2003/001820 WO2003070681A1 (en) | 2002-02-19 | 2003-02-19 | Process for the production of metal salts of radical-polymerizable compounds |
| AT03703349T ATE444274T1 (de) | 2002-02-19 | 2003-02-19 | Verfahren zur herstellung von metallsalzen von mit freien radikalen polymerisierbaren verbindungen |
| DE60329467T DE60329467D1 (de) | 2002-02-19 | 2003-02-19 | Freien radikalen polymerisierbaren verbindungen |
| AU2003207095A AU2003207095A1 (en) | 2002-02-19 | 2003-02-19 | Process for the production of metal salts of radical-polymerizable compounds |
| KR1020047012921A KR100920319B1 (ko) | 2002-02-19 | 2003-02-19 | 라디칼 중합성 화합물의 금속염의 제조방법 |
| CNB038040964A CN1293032C (zh) | 2002-02-19 | 2003-02-19 | 可自由基聚合化合物的金属盐的生产方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002040904A JP4204792B2 (ja) | 2002-02-19 | 2002-02-19 | ラジカル重合性化合物の金属塩の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003238478A JP2003238478A (ja) | 2003-08-27 |
| JP2003238478A5 JP2003238478A5 (enExample) | 2005-08-25 |
| JP4204792B2 true JP4204792B2 (ja) | 2009-01-07 |
Family
ID=27750452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002040904A Expired - Fee Related JP4204792B2 (ja) | 2002-02-19 | 2002-02-19 | ラジカル重合性化合物の金属塩の製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7183427B2 (enExample) |
| EP (1) | EP1477470B1 (enExample) |
| JP (1) | JP4204792B2 (enExample) |
| KR (1) | KR100920319B1 (enExample) |
| CN (1) | CN1293032C (enExample) |
| AT (1) | ATE444274T1 (enExample) |
| AU (1) | AU2003207095A1 (enExample) |
| DE (1) | DE60329467D1 (enExample) |
| WO (1) | WO2003070681A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4004612A1 (de) * | 1990-02-15 | 1991-08-22 | Basf Ag | Neue bichromophore methin- und azamethinfarbstoffe und ein verfahren zu ihrer uebertragung |
| JP4284136B2 (ja) * | 2003-09-10 | 2009-06-24 | 日立アプライアンス株式会社 | 冷蔵庫 |
| JP5011707B2 (ja) * | 2004-11-08 | 2012-08-29 | 三菱瓦斯化学株式会社 | メタクリル酸グリシジルの製造方法 |
| JP5191681B2 (ja) * | 2007-04-04 | 2013-05-08 | 株式会社日本触媒 | メタクリル酸アルカリ金属塩の粉体およびその製造方法、ならびにメタクリル酸アルカリ金属塩粉体の移送方法 |
| US8912298B2 (en) * | 2008-03-31 | 2014-12-16 | Nippon Shokubai Co., Ltd. | Method for producing particulate water absorbing agent containing water absorbent resin as main component |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS39220B1 (enExample) * | 1960-03-31 | 1964-01-16 | ||
| JPS3919148B1 (enExample) * | 1962-01-15 | 1964-09-07 | ||
| JPS4731924U (enExample) * | 1971-04-26 | 1972-12-11 | ||
| JPS4911820A (enExample) | 1972-05-15 | 1974-02-01 | ||
| GB1397233A (en) * | 1974-01-25 | 1975-06-11 | Ucb Sa | Process for recovering dry sodium vinyl-sulphonate from aqueous solutions |
| JPS5814416B2 (ja) * | 1975-05-26 | 1983-03-18 | 株式会社日本触媒 | アクリル酸またはメタクリル酸の亜鉛塩の製法 |
| JPS5837291B2 (ja) * | 1975-05-26 | 1983-08-15 | 株式会社日本触媒 | アクリルサン マタハ メタクリルサンノカルシウムエンノセイホウ |
| JPS61180739A (ja) * | 1985-02-05 | 1986-08-13 | Nippon Jiyouriyuu Kogyo Kk | 高純度アクリル酸アルカリ金属塩の製造方法 |
| JPH0623129B2 (ja) * | 1986-02-28 | 1994-03-30 | 三井東圧化学株式会社 | 桂皮酸類の製法 |
| US4946977A (en) | 1987-09-25 | 1990-08-07 | Huels Troisdorf Ag | Method for the preparation of organosilanes containing methacryloxy or acryloxy groups |
| JPH07138224A (ja) * | 1993-11-17 | 1995-05-30 | Tosoh Corp | ビニルスルホン酸ソーダ水溶液の製造方法 |
-
2002
- 2002-02-19 JP JP2002040904A patent/JP4204792B2/ja not_active Expired - Fee Related
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2003
- 2003-02-19 EP EP03703349A patent/EP1477470B1/en not_active Expired - Lifetime
- 2003-02-19 KR KR1020047012921A patent/KR100920319B1/ko not_active Expired - Fee Related
- 2003-02-19 US US10/501,118 patent/US7183427B2/en not_active Expired - Fee Related
- 2003-02-19 CN CNB038040964A patent/CN1293032C/zh not_active Expired - Fee Related
- 2003-02-19 DE DE60329467T patent/DE60329467D1/de not_active Expired - Lifetime
- 2003-02-19 WO PCT/JP2003/001820 patent/WO2003070681A1/ja not_active Ceased
- 2003-02-19 AU AU2003207095A patent/AU2003207095A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1477470A4 (en) | 2006-05-17 |
| EP1477470A1 (en) | 2004-11-17 |
| CN1293032C (zh) | 2007-01-03 |
| AU2003207095A1 (en) | 2003-09-09 |
| DE60329467D1 (de) | 2009-11-12 |
| JP2003238478A (ja) | 2003-08-27 |
| US20050119498A1 (en) | 2005-06-02 |
| KR100920319B1 (ko) | 2009-10-07 |
| WO2003070681A1 (en) | 2003-08-28 |
| KR20040086410A (ko) | 2004-10-08 |
| US7183427B2 (en) | 2007-02-27 |
| ATE444274T1 (de) | 2009-10-15 |
| CN1633406A (zh) | 2005-06-29 |
| EP1477470B1 (en) | 2009-09-30 |
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