KR870003232A - Liquid-permeable diaphragm for electrolytic cell, preparation method thereof and preparation method of chlorine and alkali metal hydroxide in electrolytic cell - Google Patents

Liquid-permeable diaphragm for electrolytic cell, preparation method thereof and preparation method of chlorine and alkali metal hydroxide in electrolytic cell Download PDF

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KR870003232A
KR870003232A KR1019860007385A KR860007385A KR870003232A KR 870003232 A KR870003232 A KR 870003232A KR 1019860007385 A KR1019860007385 A KR 1019860007385A KR 860007385 A KR860007385 A KR 860007385A KR 870003232 A KR870003232 A KR 870003232A
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diaphragm
group
alkali metal
organic
polymeric material
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KR900003098B1 (en
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웨인 뒤보아 도늘드
브루스 다아링턴 윌리암
로스 딜모어 커어널
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헬렌 에이 패브릭
피이피이지이 인더스트리이즈 인코포레이팃드
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    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B1/00—Electrolytic production of inorganic compounds or non-metals
    • C25B1/01—Products
    • C25B1/14—Alkali metal compounds
    • C25B1/16—Hydroxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C08J5/22—Films, membranes or diaphragms
    • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
    • C08J5/2275—Heterogeneous membranes
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B1/00—Electrolytic production of inorganic compounds or non-metals
    • C25B1/01—Products
    • C25B1/34—Simultaneous production of alkali metal hydroxides and chlorine, oxyacids or salts of chlorine, e.g. by chlor-alkali electrolysis
    • C25B1/46—Simultaneous production of alkali metal hydroxides and chlorine, oxyacids or salts of chlorine, e.g. by chlor-alkali electrolysis in diaphragm cells
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B13/00—Diaphragms; Spacing elements
    • C25B13/04—Diaphragms; Spacing elements characterised by the material
    • C25B13/08—Diaphragms; Spacing elements characterised by the material based on organic materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00—Characterised by the use of homopolymers or 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 halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or 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 halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or 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 halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2327/18—Homopolymers or copolymers of tetrafluoroethylene

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Electrochemistry (AREA)
  • Metallurgy (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

내용 없음No content

Description

전해조용 액체 투과성 격막, 이의 제조방법 및 전해조내의 염소 및 수산화알칼리금속의 제조방법Liquid permeable diaphragm for electrolytic cell, preparation method thereof and preparation method of chlorine and alkali metal hydroxide in electrolytic cell

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (42)

-COOR, -COOM, -COX, -CN, -CONR´R˝, -SO3M, -SO2NH2, -PO(OR)2, -PO(OM)2, -PO(0X)2, -OPO(OR)2, -OPO(OM)2, 및 -OPO(0X)2(여기서 R은 아릴 또는 C1-C10알킬기이고; M은 H, 알카리금속 또는 암모늄기이고; R´및 R˝는 각각 독립적으로 H 또는 C1-C10알킬기이고, X는 CI 또는 F이다)로 구성된 군으로부터 선택된 작용기를 포함하는 중합체 섬유로 구성된 유기물질로 필수적으로 구성된 전해조용 액체 투과성 격막.-COOR, -COOM, -COX, -CN, -CONR´R˝, -SO 3 M, -SO 2 NH 2 , -PO (OR) 2 , -PO (OM) 2 , -PO (0X) 2 , -OPO (OR) 2 , -OPO (OM) 2 , and -OPO (0X) 2 , where R is an aryl or C 1 -C 10 alkyl group; M is H, an alkali metal or an ammonium group; R ′ and R˝ Are each independently H or a C 1 -C 10 alkyl group, and X is CI or F). A liquid permeable diaphragm for an electrolyzer consisting essentially of an organic material composed of a polymer fiber comprising a functional group selected from the group consisting of. 제1항에 있어서, 유기 중합체 섬유가 과불소화된 격막.The diaphragm of claim 1, wherein the organic polymer fibers are perfluorinated. 제2항에 있어서, 희석제 중합체 물질을 포함하는 격막.The diaphragm of claim 2 comprising a diluent polymer material. 제3항에 있어서, 희석제 물질이 섬유성인 격막.4. The diaphragm of claim 3, wherein the diluent material is fibrous. 제4항에 있어서, 희석제 물질이 피브릴화된 폴리 테트라 플루오로에틸렌인 격막.The diaphragm of claim 4, wherein the diluent material is fibrillated poly tetra fluoroethylene. 제1항에 있어서, 작용기가 -COOR, -COOM, -COX, -CN, 및 -CONR´R˝(여기서 R은 아릴 또는 C1-C10알킬기이고; M은 H, 알킬리금속 또는 암모늄기이고; R´ 및 R˝은 각각 독립적으로 H 또는 C1-C10알칼기이고; X는 CI 또는 F이다)로 구성된 군으로부터 선택된 격막.The compound according to claim 1, wherein the functional groups are -COOR, -COOM, -COX, -CN, and -CONR'R 'wherein R is an aryl or C 1 -C 10 alkyl group; M is H, an alkylli metal or an ammonium group R ′ and R ′ are each independently H or a C 1 -C 10 alkyl group; X is CI or F). -COOM, -SO3M, -PO(OM)2, -OPO(OM)2,(여기서 M은 H, 알카리금속 또는 암모늄기이다)로 구성된 군으로부터 선택된 작용기를 포함하는 중합체 섬유로 구성된 유기물질로 필수적으로 구성된 전해조용 액체 투과성양이온 교환 격막.-COOM, -SO 3 M, -PO (OM) 2 , -OPO (OM) 2 , where M is H, an alkali metal or an ammonium group A liquid permeable cation exchange diaphragm consisting essentially of an electrolytic cell. 제7항에 있어서, 유기 중합체 섬유가 과불소화된 격막.8. The diaphragm of claim 7, wherein the organic polymer fibers are perfluorinated. 제8항에 있어서, 희석제 중합체 물질을 포함하는 격막.The diaphragm of claim 8, comprising a diluent polymer material. 제9항에 있어서, 희석제 물질이 섬유성인 격막.The diaphragm of claim 9, wherein the diluent material is fibrous. 제10항에 있어서, 희석제 물질이 피브틸화된 폴리베트라플루오로에틸렌인 격막.11. The diaphragm of claim 10, wherein the diluent material is fibylated polybetrafluoroethylene. 제7항에 있어서, 작용기가 -COOM(여기서 M은 H, 알카리금속 또는 암모늄기이다)인 격막.8. The diaphragm of claim 7, wherein the functional group is -COOM, wherein M is H, an alkali metal or an ammonium group. 격막의 섬유가 -COOR, -COOM, -COX, -CN, -CONR´R˝, -SO3M, -SO2NH2, -PO(OR)2, -PO(OM)2, -PO(0X)2, -OPO(OR)2, -OPO(OM)2, 및 -OPO(0X)2(여기서 R은 아릴 또는 C1-C10알킬기이고; M은 H, 알카리금속 또는 암모늄기이고; R' 및 R"는 각각 독립적으로 H 또는 C1-C10알킬기이고; X는 Cl 또는 F이다)로 구성된 군으로부터 선택된 작용기를 포함하는 유기 중합체 물질로 필수적으로 구성되는 전해조용 비-석면, 액체투과성, 섬유성 격막.The fibers of the diaphragm are -COOR, -COOM, -COX, -CN, -CONR´R˝, -SO 3 M, -SO 2 NH 2 , -PO (OR) 2 , -PO (OM) 2 , -PO ( 0X) 2 , -OPO (OR) 2 , -OPO (OM) 2 , and -OPO (0X) 2 , wherein R is an aryl or C 1 -C 10 alkyl group; M is H, an alkali metal or an ammonium group; R 'And R' are each independently H or a C 1 -C 10 alkyl group; X is Cl or F), a non-asbestos, liquid-permeable, electrolytic cell consisting essentially of an organic polymeric material comprising a functional group selected from the group consisting of , Fibrous diaphragm. 제13항에 있어서, 작용기가 -COOR, -COX, -CN 및 -CONR´R˝(여기서 R은 아릴 또는 C1-C10알칼기이고; M은 H, 알카리금속 또는 암모늄기이고; R´및 R˝은 각각 독립적으로 H 또는 C1-C10알킬기이고; X는 CI 또는 F이다)로 구성된 군으로부터 선택된 격막.The process according to claim 13, wherein the functional groups are -COOR, -COX, -CN and -CONR'R 'wherein R is an aryl or a C 1 -C 10 alkali group; M is H, an alkali metal or an ammonium group; R 'is each independently H or a C 1 -C 10 alkyl group; X is CI or F). 제13항에 있어서, 유기 중합체 물질이 과불소화된 격막.The diaphragm of claim 13, wherein the organic polymeric material is perfluorinated. 제15항에 있어서, 과불소화된 희석제 중합체 물질을 포함하는 격막.The diaphragm of claim 15 comprising a perfluorinated diluent polymer material. 격막의 섬유가 -COOM, -SO3M, -PO(OM)2, 및 -OPO(OM)2,(여기서 M은 H, 알카리금속 또는 암모늄기이다)로 구성된 군으로부터 선택된 작용기를 포함하는 유기 중합체 물질로 필수적으로 구성된 전해조용 비-석면, 액체 투과성, 섬유성 양이온 교환 격막.The organic polymer comprising a functional group selected from the group consisting of fibers of the diaphragm is -COOM, -SO 3 M, -PO (OM) 2 , and -OPO (OM) 2 , where M is H, an alkali metal or an ammonium group. A non-asbestos, liquid permeable, fibrous cation exchange diaphragm consisting essentially of a material. 제17항에 있어서, 작용기가 -COOM(여기서 M은 H, 알카리금속 또는 암모늄기이다)인 격막.18. The diaphragm of claim 17, wherein the functional group is -COOM, wherein M is H, an alkali metal or an ammonium group. 제17항에 있어서, 유기 중합체 물질이 과소불화된 격막.18. The diaphragm of claim 17, wherein the organic polymeric material is underfluorinated. 제19항에 있어서, 과불소화된 희석제 중합체 물질을 포함하는 격막.20. The diaphragm of claim 19 comprising a perfluorinated diluent polymer material. (a) -COOR, -COOM, -COX, -CN -CONR´R˝, -SO3M 및 -SO2NH2(여기서 R은 아릴 또는 C1-C10알킬기이고; M은 H, 알카리금속 또는 암모늄기이고; R´ 및 R˝은 각각 독립적으로 H 또는 C1-C10알킬기이고; X는 CI 또는 F이다)로 구성된 군으로부터 선택된 작용기를 포함하는 열가소성유기중합체 물질 및 액체 매체를 포함하는 슬러리를 제공하고;(a) —COOR, —COOM, —COX, —CN—CONR′R ′, —SO 3 M and —SO 2 NH 2 , where R is an aryl or C 1 -C 10 alkyl group; M is H, an alkali metal Or an ammonium group; R 'and R' are each independently H or a C 1 -C 10 alkyl group; X is CI or F) a slurry comprising a thermoplastic organic material and a liquid medium comprising a functional group selected from the group consisting of To provide; (b) 전해조의 작은 구멍이 있는 음극상에 슬러리화된 중합체 물질의 층을 부착시키고;(b) depositing a layer of slurryed polymeric material on the pinned cathode of the electrolyzer; (c) 중합체로 피복된 음극을 처리하여 상기 중합체 물질과 결합시키는 것으로 구성된 전해조의 석면이 없는 액체 투과성 격막의 제조방법.(c) A method for producing an asbestos free liquid permeable diaphragm in an electrolytic cell, comprising treating the polymer coated cathode with the polymer material. 제21항에 있어서, 유기중합체 물질이 과불소화된 방법.The method of claim 21 wherein the organopolymer material is perfluorinated. 제22항에 있어서, 열가소성 유기 중합체 물질이 실질적으로 섬유성인 방법.The method of claim 22, wherein the thermoplastic organic polymeric material is substantially fibrous. 제22항에 있어서, 슬러리가 작은 구조적 보강량의 희석제 중합체 물질을 포함하는 방법.The method of claim 22, wherein the slurry comprises a small amount of structural reinforcement diluent polymer material. 제24항에 있어서, 희석제 물질이 피브릴화된 폴리테트 라플루오로에틸렌인 방법.The method of claim 24, wherein the diluent material is fibrillated polytetrafluoroethylene. 제25항에 있어서 액체 매체가 소량의 중점제 및 소량의 비이온 계면활성제를 포함하는 물로 구성된 방법.The method of claim 25, wherein the liquid medium consists of water comprising a small amount of a midpoint and a small amount of nonionic surfactant. 제22항에 있어서, 액체 매체가 전해조작업 환경에서 유기중합체 물질이 팽윤할 때와 실질적으로 유사한 정도까지 중합체 물질을 팽윤시키고 유기 중합체 물질을 연화시킬 수 있는 유기액체로 구성되는 방법.23. The method of claim 22, wherein the liquid medium consists of an organic liquid capable of swelling the polymeric material and softening the organic polymeric material to a degree substantially similar to when the organic polymeric material swells in an electrolytic cell operating environment. 제27항에 있어서, 유기 액체가 N-메틸피롤리돈, 프로필렌 카보네이트, 디메틸 포름아미드, 디메틸설폭사이드, 이소프로판올 및 에탄올로 구성된 군으로부터 선택된 방법.The method of claim 27, wherein the organic liquid is selected from the group consisting of N-methylpyrrolidone, propylene carbonate, dimethyl formamide, dimethylsulfoxide, isopropanol and ethanol. 제25항에 있어서, 작은 구멍이 있는 음극을 부착에 앞서 제거할 수 있는, 일시적 매트로 씌우고, 이후에 유기 중합체 물질층을 일시적 매트상에 진공-증착시키고 다음에 유기중합체 물질을 결합시키는 처리를 한 후 일시적 매트를 제거하는 방법.27. The process of claim 25, wherein the treatment is carried out by covering the cathode with the small pore with a temporary mat, which can be removed prior to attachment, followed by vacuum-depositing the layer of organic polymer material onto the temporary mat and then combining the organic polymer material. How to remove the mat temporarily after doing so. 제21항에 있어서, 유기 중합체 물질로 피복된 음극의 처리가 유기 중합체물질을 결합시키기에 충분한 시간 및 온도에서 유기중합체 물질로 피복된 음극을 가열하는 것으로 구성된 방법.The method of claim 21 wherein the treatment of the negative electrode coated with the organic polymeric material consists of heating the negative electrode coated with the organic polymeric material at a time and at a temperature sufficient to bond the organic polymeric material. 제25항에 있어서, 처리가 유기 중합체 물질 및 피브릴화된 폴리테트라플루오로에틸렌으로 피복된 음극을 음극상에 격막을 보존하기 위해서, 작용기를 갖는 유기 중합체 물질 및 피브릴화된 폴리테트라플루오로에틸렌의 소결 또는 분해온도 이하의 온도에서 가열하는 것으로 구성된 방법.27. The organic polymeric material and fibrillated polytetrafluoro having functional groups according to claim 25, wherein the treatment is to preserve the diaphragm on the negative electrode coated with the organic polymeric material and the fibrillated polytetrafluoroethylene. A process consisting of heating at a temperature below the sintering or decomposition temperature of ethylene. 제21항에 있어서, 슬러리가 미공형성 물질을 포함하는 방법.The method of claim 21, wherein the slurry comprises a microporous material. 제25항에 있어서, 슬러리가 미공형성 물질을 포함하는 방법.The method of claim 25, wherein the slurry comprises a microporous material. 제25항에 있어서, 슬러리가 미공형성 물질을 포함하고 열가소성 유기 중합체 물질이 그러한 물질의 용액으로 존재하는 방법.The method of claim 25, wherein the slurry comprises a microporous material and the thermoplastic organic polymeric material is in solution of such material. (a) 액체슬러리 매체, 섬유성 희생물질 및 양이온 교환기 또는 양이온 교환기로 전환될 수 있는 작용기를 갖는 중합성 수지물질을 포함하는 슬러리를 제공하고;(a) providing a slurry comprising a liquid slurry medium, a fibrous sacrificial material and a polymeric resin material having a functional group that can be converted to a cation exchanger or a cation exchanger; (b) 슬러리를 전해조의 작은 구멍이 있는 음극에 통과시켜서 섬유성 희생물질, 수지물질 및 잔유 슬러리 매체의 층을 그 위에 부착시키고;(b) passing the slurry through the small pore cathode of the electrolytic cell to attach a layer of fibrous sacrificial material, resin material and residual slurry medium thereon; (c) 잔유 슬러리 매체를 제거하여 섬유성 희생물질 및 수지물질을 음극상에 보존하는 것으로 구성된 전해조용액체 투과성 양이온 교환 격막의 제조방법.(c) A method for producing an electrolytic cell liquid permeable cation exchange diaphragm consisting of removing residual oil slurry medium to preserve fibrous sacrificial material and resin material on the negative electrode. 제35항에 있어서, 슬러리가 비수성 액체 매체를 포함하는 비수성인 방법.36. The method of claim 35, wherein the slurry is non-aqueous comprising a non-aqueous liquid medium. 제36항에 있어서, 섬유성 희생물질이 셀룰로오스, 레이온, 초산 폴리비닐, 폴리비닐 알코올, 폴리에스테르 및 폴리아미드로 구성된 군으로부터 선택된 방법.37. The method of claim 36, wherein the fibrous sacrificial material is selected from the group consisting of cellulose, rayon, polyvinyl acetate, polyvinyl alcohol, polyester, and polyamide. 제37항에 있어서, 중합체 수지물질이 과불소화되고, 양이온 교환기 또는 양이온 교환기로 전환될 수 있는 작용기가 불화설포닐, 불화카르보닐, 설폰산 에스테르, 카르복실산 에스테르, 설폰아미드, 설폰산, 카르복실산, 포스폰산, 포스핀산 및 설포네이트, 카르복실레이트, 포스포네이트 또는 포스피네이트 작용기들의 알카리금속 또는 암모늄염으로 구성된 군으로부터 선택되는 방법.38. The functional group according to claim 37, wherein the polymer resin material is perfluorinated and the functional group which can be converted into a cation exchange group or a cation exchange group is sulfonyl fluoride, carbonyl fluoride, sulfonic acid ester, carboxylic acid ester, sulfonamide, sulfonic acid, carboxyl. Acid, phosphonic acid, phosphinic acid and sulfonate, carboxylate, phosphonate or phosphinate functional groups. (a) 수성의 염화알카리금속 염수를 전해조의 양극액 구간에 도입하고;(a) introducing an aqueous alkali metal chloride brine into the anolyte section of the electrolyser; (b) 상기 염수를 -COOM, -SO3M, -PO(OM)2, 및 -OPO(0M)2(M은 알카리금속이다)로 구성된 군으로부터 선택된 작용기를 포함하는 섬유로 구성된 유기중합체 물질로 필수적으로 구성되고, 그 안에 양극을 갖는 양극액 구간과 그 안에 음극을 갖는 음극액 구간을 나누는, 전해액 투과성의 석면이 없는 양이온 교환 격막을 통하여 전해조의 음극액 구간으로 침투시키고;(b) the brine is composed of an organic polymeric material consisting of fibers comprising a functional group selected from the group consisting of -COOM, -SO 3 M, -PO (OM) 2 , and -OPO (0M) 2 , where M is an alkali metal. Penetrates into the catholyte section of the electrolyzer through an electrolyte permeable asbestos free cation exchange diaphragm, consisting essentially of a catholyte section having an anode therein and a catholyte section having a cathode therein; (c) 전류를 양극에서 음극으로 통과시키고;(c) passing a current from the anode to the cathode; (d) 양극액 구간으로부터 염소를 회수하고 음극액 구간으로부터 수산화 알칼리금속을 회수하는 것으로 구성된 전해조내의 염소 및 수산화 알카리금속의 제조방법.(d) A process for producing chlorine and alkali metal hydroxides in an electrolytic cell consisting of recovering chlorine from the anolyte section and recovering alkali metal hydroxide from the catholyte section. 제39항에 있어서, 양이온 교환 격막이 작은 구조적 보강량의 비소결되고 피브릴화된 폴리플루오로카본을 포함하는 방법.40. The method of claim 39 wherein the cation exchange diaphragm comprises a small amount of structural reinforcement of unsintered and fibrillated polyfluorocarbons. 제40항에 있어서, 폴리플루오로카본이 폴리테트라 플로오로에틸렌인 방법.41. The method of claim 40, wherein the polyfluorocarbon is polytetrafluoroethylene. 제39항에 있어서, 염수 주입물이 50ppb이하의 알카리 토금속 이온 및 500ppb이하의 요오드를 포함하는 방법.40. The method of claim 39, wherein the saline injection comprises up to 50 ppb alkaline earth metal ions and up to 500 ppb iodine. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019860007385A 1985-09-05 1986-09-04 Methods for producing synthetic diaphragm KR900003098B1 (en)

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US77297885A 1985-09-05 1985-09-05
US772978 1985-09-05
US772,978 1985-09-05
US81319685A 1985-12-24 1985-12-24
US869,554 1986-06-02
US06/869,554 US4666573A (en) 1985-09-05 1986-06-02 Synthetic diaphragm and process of use thereof
US813,196 1991-12-23
US813196 1991-12-23
US869554 1992-04-15

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