JPWO2016042846A1 - ポリビニルアミン架橋重合体粒子の製造方法 - Google Patents
ポリビニルアミン架橋重合体粒子の製造方法 Download PDFInfo
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- JPWO2016042846A1 JPWO2016042846A1 JP2016548583A JP2016548583A JPWO2016042846A1 JP WO2016042846 A1 JPWO2016042846 A1 JP WO2016042846A1 JP 2016548583 A JP2016548583 A JP 2016548583A JP 2016548583 A JP2016548583 A JP 2016548583A JP WO2016042846 A1 JPWO2016042846 A1 JP WO2016042846A1
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- Prior art keywords
- polymerization
- water
- polymer particles
- polyvinylamine
- mass
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- Granted
Links
- 239000002245 particle Substances 0.000 title claims abstract description 34
- 229920006037 cross link polymer Polymers 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract description 30
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims abstract description 28
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- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 13
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- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 238000010557 suspension polymerization reaction Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 18
- 230000007062 hydrolysis Effects 0.000 abstract description 11
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- 229910052921 ammonium sulfate Inorganic materials 0.000 description 10
- 235000011130 ammonium sulphate Nutrition 0.000 description 10
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- 238000003756 stirring Methods 0.000 description 10
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
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- 239000000203 mixture Substances 0.000 description 8
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- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 3
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
- RTANHMOFHGSZQO-UHFFFAOYSA-N 4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)C#N RTANHMOFHGSZQO-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- WYFGBFHRZGNGAU-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;hydrochloride Chemical compound Cl.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 WYFGBFHRZGNGAU-UHFFFAOYSA-N 0.000 description 1
- LSGUXGJUXCTZPW-UHFFFAOYSA-N bis[2-(5-methyl-4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;hydrochloride Chemical compound Cl.N1C(C)CN=C1C(C)(C)N=NC(C)(C)C1=NCC(C)N1 LSGUXGJUXCTZPW-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
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- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 230000001788 irregular Effects 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- ZJDNTSGQAOAXNR-UHFFFAOYSA-N n-ethenyl-2-methylpropanamide Chemical compound CC(C)C(=O)NC=C ZJDNTSGQAOAXNR-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 1
- DSENQNLOVPYEKP-UHFFFAOYSA-N n-ethenyl-n-methylpropanamide Chemical compound CCC(=O)N(C)C=C DSENQNLOVPYEKP-UHFFFAOYSA-N 0.000 description 1
- HAZULKRCTMKQAS-UHFFFAOYSA-N n-ethenylbutanamide Chemical compound CCCC(=O)NC=C HAZULKRCTMKQAS-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
- B01J20/267—Cross-linked polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/18—Suspension polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
(重合反応)300mLの4つ口フラスコに脱塩水50.0g、硫酸アンモニウム30.0g、ポリアクリロイルオキシエチルトリメチルアンモニウム塩化物水溶液(ポリマー濃度20質量%、重量平均分子量80万)0.97gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド29.95g、55質量%ジビニルベンゼン0.15g、アゾ系重合開始剤2、2’−アゾビス(2、4−ジメチルバレロニトリル)(V−65、和光純薬工業(株)製)0.08gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら200rpmで撹拌した。30分後昇温し、65℃で1時間、続いて70℃で2時間重合した。重合後濾過、水洗し、濾過し、含水状態の重合体球状粒子344gを得た。固形分率は6.0%であった。
(重合反応)300mLの4つ口フラスコに脱塩水50.2g、硫酸アンモニウム32.2g、ポリアクリロイルオキシエチルトリメチルアンモニウム塩化物水溶液(ポリマー濃度20質量%、重量平均分子量80万)1.00gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド19.62g、55質量%ジビニルベンゼン0.44g、アゾ系重合開始剤2、2’−アゾビス(2、4−ジメチルバレロニトリル)(V−65、和光純薬工業(株)製)0.08gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら200rpmで撹拌した。30分後昇温し、60℃で2時間、続いて70℃で2時間重合した。重合後濾過、水洗し、濾過し、含水状態の重合体球状粒子113.2gを得た。固形分率は12.4%であった。
(重合反応)300mLの4つ口フラスコに脱塩水50.0g、硫酸アンモニウム35.2g、ポリアクリロイルオキシエチルトリメチルアンモニウム塩化物水溶液(ポリマー濃度20質量%、重量平均分子量80万)1.05gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド19.0g、55質量%ジビニルベンゼン1.0g、アゾ系重合開始剤2、2’−アゾビス(2、4−ジメチルバレロニトリル)(V−65、和光純薬工業(株)製)0.08gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら250rpmで撹拌した。30分後昇温し、65℃で1時間、続いて70℃で3時間重合した。重合後濾過、水洗し、濾過し、含水状態の重合体球状粒子79.4gを得た。固形分率は14.5%であった。
(重合反応)300mLの4つ口フラスコに脱塩水50.1g、硫酸アンモニウム32.0g、ポリアクリロイルオキシエチルトリメチルアンモニウム塩化物水溶液(ポリマー濃度20質量%、重量平均分子量80万)0.97gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド19.8g、55質量%ジビニルベンゼン0.23g、アゾ系重合開始剤2、2’−アゾビス(2、4−ジメチルバレロニトリル)(V−65、和光純薬工業(株)製)0.08gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら250rpmで撹拌した。30分後昇温し、60℃で2時間、続いて70℃で3時間重合した。重合後濾過、水洗し、濾過し、含水状態の重合体球状粒子168.2gを得た。固形分率は8.2%であった。
(重合反応)300mLの4つ口フラスコに脱塩水50.1g、硫酸アンモニウム32.0g、ポリアクリロイルオキシエチルトリメチルアンモニウム塩化物水溶液(ポリマー濃度20質量%、重量平均分子量80万)1.04gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド30.0g、55質量%ジビニルベンゼン0.15g、アゾ系重合開始剤2、2’−アゾビス(4−メトキシ−2、4−ジメチルバレロニトリル)(V−70、和光純薬工業(株)製)0.09gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら250rpmで撹拌した。30分後昇温し、40℃で1.5時間、続いて60℃で1.5時間重合した。重合後濾過、水洗し、濾過し、含水状態の重合体球状粒子364.1gを得た。固形分率は6.5%であった。
(重合反応)300mLの4つ口フラスコに脱塩水49.3g、硫酸アンモニウム32.0g、ポリアクリロイルオキシエチルトリメチルアンモニウム塩化物水溶液(ポリマー濃度20質量%、重量平均分子量80万)1.19gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド18.01g、ジビニルベンゼン(和光純薬工業(株)製)1.02g、アクリロニトリル1.06g、アゾ系重合開始剤2、2’−アゾビス(4−メトキシ−2、4−ジメチルバレロニトリル)(V−70、和光純薬工業(株)製)0.06gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら300rpmで撹拌した。30分後昇温し、45℃で2時間、続いて60℃で1時間重合した。重合後濾過、水洗し、濾過し、含水状態の重合体球状粒子51.1gを得た。固形分率は31.7%であった。
(重合反応)300mLの4つ口フラスコに脱塩水98.39g、硫酸アンモニウム64.04g、ポリアクリロイルオキシエチルトリメチルアンモニウム塩化物水溶液(ポリマー濃度20質量%、重量平均分子量80万)2.21gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド28.85g、ジビニルベンゼン(和光純薬工業(株)製)3.22g、アクリロニトリル8.03g、アゾ系重合開始剤2、2’−アゾビス(4−メトキシ−2、4−ジメチルバレロニトリル)(V−70、和光純薬工業(株)製)0.12gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら300rpmで撹拌した。30分後昇温し、45℃で2時間、続いて60℃で1時間重合した。重合後濾過、水洗し、濾過し、含水状態の重合体球状粒子72.8gを得た。固形分率は45.8%であった。
(重合反応)300mLの4つ口フラスコに脱塩水50.0g、ポリアクリロイルオキシエチルトリメチルアンモニウム塩化物水溶液(ポリマー濃度20質量%、重量平均分子量80万)0.97gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド29.95g、55質量%ジビニルベンゼン0.15g、アゾ系重合開始剤2、2’−アゾビス(2、4−ジメチルバレロニトリル)(V−65、和光純薬工業(株)製)0.08gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら200rpmで撹拌した。30分後昇温し、65℃で1時間、続いて70℃で2時間重合した。重合後濾過、水洗し、濾過したが、得られた重合体は不定形状であり、球状粒子は得られなかった。
(重合反応)300mLの4つ口フラスコに脱塩水50.0g、硫酸アンモニウム30.0gを投入し、撹拌し、溶解させ、重合浴とした。N−ビニルホルムアミド29.95g、55質量%ジビニルベンゼン0.15g、アゾ系重合開始剤2、2’−アゾビス(2、4−ジメチルバレロニトリル)(V−65、和光純薬工業(株)製)0.08gを混合し、モノマー溶液とした。モノマー溶液と重合浴を混合、窒素でフラスコ内を置換しながら200rpmで撹拌した。30分後昇温し、65℃で1時間、続いて70℃で2時間重合した。重合後濾過、水洗し、濾過したが、得られた重合体は不定形状であり、球状粒子は得られなかった。
Claims (3)
- N−ビニルカルボン酸アミドとポリビニル化合物を含有する塩水中で分散剤存在下、懸濁重合して得た架橋重合体粒子を加水分解して製造することを特徴とするポリビニルアミン架橋重合体粒子の製造方法。
- 前記塩水中にN−ビニルカルボン酸アミドとポリビニル化合物、更にアクリロニトリルを含有することを特徴とする請求項1に記載の製造方法。
- 前記ポリビニル化合物がジビニルベンゼンであることを特徴とする請求項1あるいは2に記載の製造方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6151007A (ja) * | 1984-08-20 | 1986-03-13 | Mitsubishi Chem Ind Ltd | ポリビニルアミン架橋物の製造方法 |
JPH05125117A (ja) * | 1991-11-05 | 1993-05-21 | Mitsubishi Kasei Corp | 水溶性ポリマーの製造法 |
JPH0971660A (ja) * | 1995-07-06 | 1997-03-18 | Kurita Water Ind Ltd | ビニルアミン系ポリマーの水系分散液の製造方法 |
JP2001129395A (ja) * | 1999-11-10 | 2001-05-15 | Showa Denko Kk | 吸着剤、吸着成型体及びそれらを用いた化合物分離用具 |
JP2006000759A (ja) * | 2004-06-17 | 2006-01-05 | Tomoe Engineering Co Ltd | 回転式圧縮濾過機用汚泥脱水剤およびそれを用いた汚泥脱水方法 |
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US3689439A (en) * | 1968-06-12 | 1972-09-05 | Gaf Corp | Process for preparing a crosslinked porous polyvinyl pyrrolidone granule |
US5630907A (en) * | 1992-12-07 | 1997-05-20 | Basf Aktiengesellschaft | Use of hydrolyzed copolymers of N-vinylcarboxamides and monoethylenically unsaturated carboxylic acids in papermaking |
JPH06190235A (ja) | 1992-12-25 | 1994-07-12 | Mitsubishi Kasei Corp | ガス吸着剤及びこれを用いるガス処理方法 |
DE4421179A1 (de) * | 1994-06-17 | 1995-12-21 | Basf Ag | Farbstoffübertragungsinhibitoren für Wasch- und Reinigungsmittel |
US6426383B1 (en) * | 1997-05-28 | 2002-07-30 | Nalco Chemical Company | Preparation of water soluble polymer dispersions from vinylamide monomers |
DE69917168T2 (de) * | 1998-10-02 | 2005-01-13 | Showa Denko K.K. | Poröse Copolymerpartikel, Verfahren zu deren Herstellung und deren Verwendung |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6151007A (ja) * | 1984-08-20 | 1986-03-13 | Mitsubishi Chem Ind Ltd | ポリビニルアミン架橋物の製造方法 |
JPH05125117A (ja) * | 1991-11-05 | 1993-05-21 | Mitsubishi Kasei Corp | 水溶性ポリマーの製造法 |
JPH0971660A (ja) * | 1995-07-06 | 1997-03-18 | Kurita Water Ind Ltd | ビニルアミン系ポリマーの水系分散液の製造方法 |
JP2001129395A (ja) * | 1999-11-10 | 2001-05-15 | Showa Denko Kk | 吸着剤、吸着成型体及びそれらを用いた化合物分離用具 |
JP2006000759A (ja) * | 2004-06-17 | 2006-01-05 | Tomoe Engineering Co Ltd | 回転式圧縮濾過機用汚泥脱水剤およびそれを用いた汚泥脱水方法 |
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