KR100433205B1 - 3-Isothiazolone solution - Google Patents
3-Isothiazolone solution Download PDFInfo
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- KR100433205B1 KR100433205B1 KR10-2003-0005971A KR20030005971A KR100433205B1 KR 100433205 B1 KR100433205 B1 KR 100433205B1 KR 20030005971 A KR20030005971 A KR 20030005971A KR 100433205 B1 KR100433205 B1 KR 100433205B1
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- South Korea
- Prior art keywords
- isothiazolone
- solution composition
- methyl
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- glycol
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- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 27
- -1 NaHCO 3 Substances 0.000 claims abstract description 17
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical compound O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 239000007844 bleaching agent Substances 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 claims description 4
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- CVZDIUZSWUDGOP-UHFFFAOYSA-N 4,5-dichloro-2-methyl-1,2-thiazol-3-one Chemical compound CN1SC(Cl)=C(Cl)C1=O CVZDIUZSWUDGOP-UHFFFAOYSA-N 0.000 claims description 2
- PTMXFIUOGSODQW-UHFFFAOYSA-N 5-chloro-2-octyl-1,2-thiazol-3-one Chemical compound CCCCCCCCN1SC(Cl)=CC1=O PTMXFIUOGSODQW-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims description 2
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- NHKHUHXMKHSOJT-UHFFFAOYSA-N 2-methyl-1,2-thiazolidin-4-one Chemical compound CN1CC(=O)CS1 NHKHUHXMKHSOJT-UHFFFAOYSA-N 0.000 claims 1
- PNMDWIWITQAMOH-UHFFFAOYSA-N 4-benzyl-1,2-thiazol-3-one Chemical compound O=C1NSC=C1CC1=CC=CC=C1 PNMDWIWITQAMOH-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 9
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 7
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 abstract description 6
- 229910019093 NaOCl Inorganic materials 0.000 abstract description 6
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 6
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 abstract description 6
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract description 6
- 241001550224 Apha Species 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000004042 decolorization Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical group [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- IHDKBHLTKNUCCW-UHFFFAOYSA-N 1,3-thiazole 1-oxide Chemical compound O=S1C=CN=C1 IHDKBHLTKNUCCW-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- 229920001100 Polydextrose Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000001259 polydextrose Substances 0.000 description 1
- 229940035035 polydextrose Drugs 0.000 description 1
- 235000013856 polydextrose Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- YJPVTCSBVRMESK-UHFFFAOYSA-L strontium bromide Chemical compound [Br-].[Br-].[Sr+2] YJPVTCSBVRMESK-UHFFFAOYSA-L 0.000 description 1
- 229910001625 strontium bromide Inorganic materials 0.000 description 1
- 229940074155 strontium bromide Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B3/00—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form
- B32B3/26—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form characterised by a particular shape of the outline of the cross-section of a continuous layer; characterised by a layer with cavities or internal voids ; characterised by an apertured layer
- B32B3/28—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form characterised by a particular shape of the outline of the cross-section of a continuous layer; characterised by a layer with cavities or internal voids ; characterised by an apertured layer characterised by a layer comprising a deformed thin sheet, i.e. the layer having its entire thickness deformed out of the plane, e.g. corrugated, crumpled
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/01—Layered products comprising a layer of metal all layers being exclusively metallic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/18—Layered products comprising a layer of metal comprising iron or steel
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2255/00—Coating on the layer surface
- B32B2255/06—Coating on the layer surface on metal layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2255/00—Coating on the layer surface
- B32B2255/26—Polymeric coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2419/00—Buildings or parts thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2607/00—Walls, panels
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
본 발명은 3-이소티아졸론 용액 조성물에 관한 것으로서, 더욱 상세하게는 다음 화학식 1로 표시되는 이소티아졸론이 용해되어 있는 용액에 금속 브롬산염, NaOCl, 트리클로로이소시아누레이트, NaHCO3, Na2CO3및 H3PO4중에서 선택된 화합물이 일정량 함유되어 있어 이소티아졸론 화합물의 살균력 및 안정성에 전혀 영향을 미치지 아니하면서 용액 조성물의 색도 개선효과를 가지게 되는 이소티아졸론 용액 조성물에 관한 것이다.The present invention relates to a 3-isothiazolone solution composition, and more particularly, metal bromate, NaOCl, trichloroisocyanurate, NaHCO 3 , Na 2 CO in a solution in which isothiazolone represented by the following formula (1) is dissolved: The present invention relates to an isothiazolone solution composition containing a certain amount of a compound selected from 3 and H 3 PO 4 to have a color improving effect of the solution composition without affecting the bactericidal power and stability of the isothiazolone compound.
상기 화학식 1에서, R1, R2및 R3는 각각 발명의 상세한 설명란에서 정의한 바와 같다.In Formula 1, R 1 , R 2 and R 3 are each as defined in the detailed description of the invention.
Description
본 발명은 3-이소티아졸론 용액 조성물에 관한 것으로서, 더욱 상세하게는 다음 화학식 1로 표시되는 이소티아졸론이 용해되어 있는 용액에 금속 브롬산염, NaOCl, 트리클로로이소시아누레이트, NaHCO3, Na2CO3및 H3PO4중에서 선택된 화합물이 일정량 함유되어 있어 이소티아졸론 화합물의 살균력 및 안정성에 전혀 영향을 미치지 아니하면서 용액 조성물의 색도 개선효과를 가지게 되는 이소티아졸론 용액 조성물에 관한 것이다.The present invention relates to a 3-isothiazolone solution composition, and more particularly, metal bromate, NaOCl, trichloroisocyanurate, NaHCO 3 , Na 2 CO in a solution in which isothiazolone represented by the following formula (1) is dissolved: The present invention relates to an isothiazolone solution composition containing a certain amount of a compound selected from 3 and H 3 PO 4 to have a color improving effect of the solution composition without affecting the bactericidal power and stability of the isothiazolone compound.
화학식 1Formula 1
상기 화학식 1에서, R1및 R2는 서로 같거나 다른 것으로서 수소원자, 할로겐원자 또는 C1∼C4의 알킬기이거나, 또는 R1과 R2가 서로 결합하여 고리화된 아릴기를 형성하고; R3는 수소원자, C1∼C18의 알킬기, C2∼C18의 알케닐기, C2∼C18의 알키닐기, 3∼8원자 고리가 결합되어 있는 C3∼C12의 시클로알킬기, C10∼C24의 아랄킬기, 또는 C10∼C18의 아릴기이다.In Formula 1, R 1 and R 2 are the same as or different from each other and are a hydrogen atom, a halogen atom or an alkyl group of C 1 to C 4 , or R 1 and R 2 are bonded to each other to form a cyclized aryl group; R 3 is a hydrogen atom, a C 1 -C 18 alkyl group, a C 2 -C 18 alkenyl group, a C 2 -C 18 alkynyl group, a C 3 -C 12 cycloalkyl group having a 3-8 membered ring bonded thereto, an aryl group of C 10 ~C 24 aralkyl, or C 10 ~C 18 a.
3-이소티아졸론 화합물은 살균제를 비롯해 도료, 화장품, 섬유 또는 플라스틱 등의 항균 및 항미생물제로서 산업전반에 걸쳐 확대되어 사용되고 있다.3-isothiazolone compounds are widely used throughout the industry as antibacterial and antimicrobial agents, such as paints, cosmetics, textiles or plastics, as well as fungicides.
일반적으로 화합물에 있어서 색을 나타내는 주된 요인은 제조공정중 부산물로 생성되는 소량의 유기화합물(불순물)에 의한 것으로, 이들 부산물에 의해 생성된 색(color)을 제거하는 방법으로는 카본블랙(Carbon Black)을 투입하여 제품내 흑색을 띠게 하거나 TiO2를 첨가하여 백색을 띠게하는 마스킹제(Masking Agent)에 의한 방법 및 이온교환수지 및 활성탄을 이용하여 물리적방법에 의해 색을 나타내는 성분을 제거하는 방법이 이용되고 있다.In general, the main factor in the color of the compound is due to a small amount of organic compounds (impurities) generated as by-products in the manufacturing process, and carbon black (Carbon Black) is a method for removing the color generated by these by-products. By using a masking agent to make the product black by adding) or by adding TiO 2 to make it white, and to remove the component that shows color by physical method using ion exchange resin and activated carbon. It is used.
한편, 현재까지 알려져 있는 일반적인 탈색방법으로는 다음과 같은 방법이 있다: 미국특허 제4,731,165호에는 술폰산 이온교환수지를 이용한 트리에틸렌 테트라아민의 탈색방법이 기술되어 있고; 미국특허 제4,609,436호에는 염소화탄화수소와 폴리에틸렌 폴리아민을 결합시킨 탈색물을 형성한 후에 증류 공정을 거쳐 탈색된 폴리에틸렌 폴리아민을 얻는 방법이 기술되어 있으며; 대한민국 특허공고 제96-0065호에는 한외 여과막을 이용하여 간장을 탈색시키는 방법이 기술되어 있으며; 대한민국 특허공고 제95-0136호에는 폐 휴지 물질로부터 얻어진 펄프를 높은 pH에서 산소 기체와 접촉시켜 색소를 제거하는 방법이 기술되어 있으며; 대한민국특허공고 제95-0092호에는 이온교환수지 및 알루미나 수지를 이용하여 반코마이신을 탈색하는 방법이 기술되어 있으며; 대한민국 특허공고 제93-1318호에는 활성탄과 이온교환수지를 이용하여 폴리덱스트로스를 탈색 및 정제하는 방법이 기술되어 있다.On the other hand, as a general decolorization method known to date there is the following method: US Patent No. 4,731,165 describes a decolorization method of triethylene tetraamine using a sulfonic acid ion exchange resin; US Patent No. 4,609,436 describes a method for obtaining a decolorized polyethylene polyamine through a distillation process after forming a decolorized product combining chlorinated hydrocarbons and a polyethylene polyamine; Korean Patent Publication No. 96-0065 discloses a method of decolorizing soy sauce using an ultrafiltration membrane; Korean Patent Publication No. 95-0136 describes a method for removing a pigment by contacting pulp obtained from waste resting material with oxygen gas at high pH; Korean Patent Publication No. 95-0092 discloses a method for decolorizing vancomycin using ion exchange resins and alumina resins; Korean Patent Publication No. 93-1318 describes a method for decolorizing and purifying polydextrose using activated carbon and an ion exchange resin.
이상에서 설명된 종래 탈색방법중 이온교환수지 또는 활성탄 칼럼을 이용하는 기술은 장치 설치 및 유지비용이 많이 소요되는 바, 상대적으로 제품 가격이 저렴한 살균제의 탈색방법으로 적용하기에는 경제성이 없다.Among the conventional decolorization methods described above, a technique using an ion exchange resin or an activated carbon column requires a lot of equipment installation and maintenance costs, and thus it is not economical to apply the decolorizing method of a disinfectant having a relatively low product price.
따라서, 3-이소티아졸론 화합물의 살균력 및 저장안정성에 전혀 영향을 주지 않으면서도 산업적으로 적용 가치가 있는 새로운 색 제거방법이 요구된다.Therefore, there is a need for a new method of color removal that is of industrial value without affecting the bactericidal power and storage stability of the 3-isothiazolone compound.
본 발명은 3-이소티아졸론 화합물 특유의 불쾌한 색(Color)을 제거함에 있어 경제성이 결여된 물리적인 탈색방법을 배제시키고, 탈색제로서 이미 공지되어 있는 여러 화합물 중에서도 특히 3-이소티아졸론 화합물 고유의 화학적 특성에 최 적합한 탈색제를 선별하여 함유시킴으로써 완성하였다.The present invention eliminates the physical decolorization method that lacks economic efficiency in removing the unpleasant color peculiar to the 3-isothiazolone compound, and is particularly inherent to the 3-isothiazolone compound among various compounds already known as decolorizing agents. Completion was achieved by selecting and containing the bleach most suitable for chemical properties.
따라서, 본 발명은 살균력 및 저장안정성이 유지되면서도 화합물 특유의 색(Color)이 제거된 살균활성 3-이소티아졸론 용액 조성물을 제공하는데 그 목적이 있다.Accordingly, an object of the present invention is to provide a bactericidal active 3-isothiazolone solution composition in which color specific to a compound is removed while maintaining bactericidal power and storage stability.
본 발명은 다음 화학식 1로 표시되는 3-이소티아졸론 용액 조성물에 있어서, 상기 용액 조성물중에는 금속 브롬산염, NaOCl, 트리클로로이소시아누레이트, NaHCO3, Na2CO3및 H3PO4중에서 선택된 화합물이 0.1 ppm ∼ 20% 농도로 함유되어 있는 것을 그 특징으로 한다.In the 3-isothiazolone solution composition represented by the following formula (1), the compound selected from metal bromate, NaOCl, trichloroisocyanurate, NaHCO 3 , Na 2 CO 3 and H 3 PO 4 is It is characterized by containing at 0.1 ppm-20% concentration.
화학식 1Formula 1
상기 화학식 1에서 : R1, R2및 R3는 각각 상기에서 정의한 바와 같다.In Chemical Formula 1, R 1 , R 2, and R 3 are each as defined above.
이와 같은 본 발명을 더욱 상세히 설명하면 다음과 같다.Referring to the present invention in more detail as follows.
본 발명은 3-이소티아졸론 용액 조성물 중에 특별히 선정된 탈색제가 일정 농도로 함유되어 있어 화합물 특유의 불쾌한 색(Color)을 제거하고, 또한 3-이소티아졸론 본연의 살균활성을 유지시키면서 저장안정성에도 전혀 문제가 없는 신규의 3-이소티아졸론 용액 조성물에 관한 것이다.In the present invention, the specific iso-selective bleaching agent is contained in the 3-isothiazolone solution composition to remove unpleasant color peculiar to the compound, and the storage stability while maintaining the sterilizing activity of 3-isothiazolone in nature. A novel 3-isothiazolone solution composition with no problem at all.
본 발명에 따른 용액 조성물 중에는 탈색제로서 금속 브롬산염, NaOCl, 트리클로로이소시아누레이트, NaHCO3, Na2CO3및 H3PO4중에서 선택된 1종 또는 2종 이상의 화합물이 함유된다. 상기 금속 브롬산염은 브롬산 나트륨, 브롬산 칼륨, 브롬산 칼슘, 브롬산 마그네슘, 브롬산 리튬, 브롬산 스트론튬, 브롬산 코발트, 브롬산 아연 중에서 선택하여 사용하는 것이 바람직하고, 특히 바람직하게는 브롬산 나트륨, 브롬산 칼륨, 브롬산 마그네슘 중에서 선택하여 사용하는 것이다.The solution composition according to the present invention contains one or two or more compounds selected from metal bromate, NaOCl, trichloroisocyanurate, NaHCO 3 , Na 2 CO 3 and H 3 PO 4 as decolorizing agents. The metal bromate is selected from sodium bromide, potassium bromide, calcium bromide, magnesium bromide, lithium bromide, strontium bromide, cobalt bromide and zinc bromide, and particularly preferably bromic acid. It is selected from sodium, potassium bromide and magnesium bromide.
본 발명자들의 연구 결과에 따르면, 공지의 여러 탈색제 중에서도 특히 상기한 탈색제 화합물은 상기 화학식 1로 표시되는 3-이소티아졸론 화합물과의 화학적 친화성이 우수하여 장기간 함께 함유시켜 저장하여도 색 안정성이 우수함을 확인하였다. 상기한 탈색제의 사용량은 그 종류에 따라 다소 차이는 있으나 전체 용액 조성물중에 0.1 ppm ∼ 20% 농도로 함유시키도록 하는 것이 바람직한 바, 0.1 ppm 농도 미만으로 함유되면 요구되는 색 제거효과를 얻을 수 없고, 20% 농도를 초과하여 과량 함유시키는 것은 경제적으로 바람직하지 못하다. 특히 바람직하기로는 금속 브롬산염의 경우는 0.01% ∼ 2%, 특히 더 바람직하기로는 0.01% ∼ 1%를 함유시키는 것이고, NaOCl의 경우는 0.01% ∼ 1%를 함유시키는 것이고, 트리클로로이소시아누레이트의 경우는 0.1% ∼ 10%를 함유시키는 것이고, NaHCO3와 Na2CO3의 경우는 0.5% ∼ 10%를 함유시키는 것이고, H3PO4의 경우는 1 ppm ∼ 3%를 함유시키는 것이다.According to the results of the present inventors, among the various known bleaching agents, in particular, the above-described bleaching compound is excellent in chemical affinity with the 3-isothiazolone compound represented by the formula (1) and excellent in color stability even when stored together for a long time. It was confirmed. The amount of the bleaching agent used varies slightly depending on the kind thereof, but it is preferable to include 0.1 ppm to 20% in the total solution composition. If the concentration is less than 0.1 ppm, the required color removal effect cannot be obtained. It is economically undesirable to contain excess in excess of 20% concentration. Particularly preferably, metal bromate is 0.01% to 2%, particularly preferably 0.01% to 1%, and NaOCl is 0.01% to 1%, and trichloroisocyanurate In this case, 0.1% to 10% is contained, in the case of NaHCO 3 and Na 2 CO 3 , 0.5% to 10% is contained, and in the case of H 3 PO 4 , 1 ppm to 3% is included.
한편, 살균제로서 사용되고 있는 상기 화학식 1로 표시되는 3-이소티아졸론 화합물 중에서도 5-클로로-2-메틸-4-이소티아졸린-3-온, 2-메틸-4-이소티아졸린-3-온, 4,5-디클로로-2-메틸-4-이소티아졸린-3-온, 5-클로로-2-n-옥틸-3-이소티아졸론, 4,5-디클로로-2-n-옥틸-3-이소티아졸론, 벤즈이소티아졸론 중에서 선택하여 함유시킬 본 발명의 목적 달성에 보다 바람직하다. 특히 바람직하기로는 5-클로로-2-메틸-4-이소티아졸론-3-온과 2-메틸-4-이소티아졸론-3-온이 1 : 20 ∼ 20:1 중량비로 혼합되어 있는 혼합물을 사용하는 것이다.Meanwhile, 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one also among the 3-isothiazolone compounds represented by the above formula (1) used as fungicides. , 4,5-dichloro-2-methyl-4-isothiazolin-3-one, 5-chloro-2-n-octyl-3-isothiazolone, 4,5-dichloro-2-n-octyl-3 -It is more preferable for achieving the objective of this invention to select and contain from isothiazolone and benzisothiazolone. Particularly preferred is a mixture of 5-chloro-2-methyl-4-isothiazolone-3-one and 2-methyl-4-isothiazolone-3-one in a 1:20 to 20: 1 weight ratio. Is to use.
또한, 본 발명에 따른 용액 조성물에는 상기한 3-이소티아졸론 화합물과 탈색제, 그리고 물을 함유하고 있고, 그 밖에도 이소티아졸론의 안정제로서 일반적으로 알려져 있는 에틸렌 글리콜, 프로필렌 글리콜, 디프로필렌 글리콜, 폴리프로필렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 1,5-펜탄디올, 2,4-펜탄디올, 및 벤질알콜을 공지의 함량 범위 내에서 함유시킬 수도 있다.In addition, the solution composition according to the present invention contains the aforementioned 3-isothiazolone compound, a bleaching agent, and water, and other ethylene glycol, propylene glycol, dipropylene glycol, polypropylene, which are generally known as stabilizers of isothiazolone. Propylene glycol, diethylene glycol, triethylene glycol, 1,5-pentanediol, 2,4-pentanediol, and benzyl alcohol may be contained within a known content range.
이상에서 설명한 바와 같은 본 발명은 다음의 실시예 및 비교예에 의거하여 더욱 상세히 설명하면 다음과 같은 바, 본 발명이 이에 한정되는 것은 아니다.The present invention as described above will be described in more detail based on the following examples and comparative examples as follows, but the present invention is not limited thereto.
실시예 1Example 1
5-클로로-2-메틸-4-이소티아졸린-3-온과 2-메틸-4-이소티아졸린-3-온이 약 3 : 1 중량비로 혼합되어 용해되어 있는 14 중량%의 3-이소티아졸론 용액 각각에 브롬산 나트륨을 0 중량%, 0.2 중량%, 0.4 중량%, 0.6 중량%, 0.8 중량%, 1.0 중량%가 되도록 각각 투입하여 완전히 용해될 때까지 교반하였다.14 wt% of 3-iso iso- 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one are dissolved in a mixture of about 3: 1 by weight. Sodium bromide was added to each of the thiazolone solutions so as to be 0 wt%, 0.2 wt%, 0.4 wt%, 0.6 wt%, 0.8 wt%, and 1.0 wt%, and stirred until complete dissolution.
제조된 용액의 탈색 효과를 알아보기 위하여, 실온에서 48시간 방치하고 증류수로 10배 희석시킨 후 APHA 측정장치(Aqua Tester, ORBECO ANALYTICAL SYSTEMS, INC., USA)를 이용하여 APHA 색가[Annual book of ASTM standards, Section 6 참조]를 측정하였다.In order to determine the decolorizing effect of the prepared solution, it was left at room temperature for 48 hours, diluted 10 times with distilled water, and then APHA color value [Anual book of ASTM using an APHA measuring device (Aqua Tester, ORBECO ANALYTICAL SYSTEMS, INC., USA)] standards, see Section 6].
또한, 제조된 용액의 저장안정성을 알아보기 위하여 65 ℃ 항온조에 방치하면서 열 안정성을 측정하였으며, 열 안정성 측정에 의한 분해정도는 고성능 액체크로마토그래피(HPLC, High Performance Liquid Chromatography)로 측정하였다.In addition, the thermal stability was measured while standing in a 65 ℃ thermostat in order to determine the storage stability of the prepared solution, the decomposition degree by the thermal stability measurement was measured by High Performance Liquid Chromatography (HPLC).
실시예 2Example 2
5-클로로-2-메틸-4-이소티아졸린-3-온과 2-메틸-4-이소티아졸린-3-온이 약 3 : 1 중량비로 혼합되어 용해되어 있는 14 중량%의 3-이소티아졸론 용액 각각에 4% NaOCl 0.05 중량%, 트리클로로이소시아누레이트 0.5 중량%, NaHCO31.0 중량%, Na2CO31.0 중량% 및 H3PO40.05 중량%가 되도록 각각 투입하여 완전히 용해될 때까지 교반하였다.14 wt% of 3-iso iso- 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one are dissolved in a mixture of about 3: 1 by weight. To each of the thiazolone solutions, 0.05% by weight of 4% NaOCl, 0.5% by weight of trichloroisocyanurate, 1.0% by weight of NaHCO 3, 1.0% by weight of Na 2 CO 3 and 0.05% by weight of H 3 PO 4 were dissolved completely. Stir until.
제조된 용액의 탈색 효과를 알아보기 위하여, 실온에서 48시간 방치하고 증류수로 10배 희석시킨 후 APHA 측정장치(Aqua Tester, ORBECO ANALYTICAL SYSTEMS, INC., USA)를 이용하여 APHA 색가를 측정하였다.In order to determine the decolorizing effect of the prepared solution, the mixture was left at room temperature for 48 hours, diluted 10 times with distilled water, and then APHA color value was measured using an APHA measuring device (Aqua Tester, ORBECO ANALYTICAL SYSTEMS, INC., USA).
또한, 제조된 용액의 저장안정성을 알아보기 위하여 65 ℃ 항온조에 방치하면서 열 안정성을 측정하였으며, 열 안정성 측정에 의한 분해정도는 고성능 액체크로마토그래피(HPLC, High Performance Liquid Chromatography)로 측정하였다.In addition, the thermal stability was measured while standing in a 65 ℃ thermostat in order to determine the storage stability of the prepared solution, the decomposition degree by the thermal stability measurement was measured by High Performance Liquid Chromatography (HPLC).
실시예 3Example 3
5-클로로-2-메틸-4-이소티아졸론-3-온과 2-메틸-4-이소티아졸론-3-온이 약 12 : 1 중량비로 혼합되어 용해되어 있는 14 중량%의 3-이소티아졸론 용액 각각에 브롬산 나트륨 0 중량%, 0.08 중량% 및 0.1 중량%가 되도록 각각 투입하여 완전히 용해될 때까지 교반하였다.14% by weight of 3-iso iso- 5-chloro-2-methyl-4-isothiazolone-3-one and 2-methyl-4-isothiazolone-3-one are mixed and dissolved in about 12: 1 weight ratio. To each of the thiazolone solutions, 0 wt%, 0.08 wt%, and 0.1 wt% of sodium bromide were added thereto, followed by stirring until complete dissolution.
제조된 용액의 탈색 효과를 알아보기 위하여, 실온에서 48시간 방치하고 증류수로 10배 희석시킨 후 APHA 측정장치(Aqua Tester, ORBECO ANALYTICAL SYSTEMS, INC., USA)를 이용하여 APHA 색가를 측정하였다.In order to determine the decolorizing effect of the prepared solution, the mixture was left at room temperature for 48 hours, diluted 10 times with distilled water, and then APHA color value was measured using an APHA measuring device (Aqua Tester, ORBECO ANALYTICAL SYSTEMS, INC., USA).
또한, 제조된 용액의 저장안정성을 알아보기 위하여 65 ℃ 항온조에 방치하면서 열 안정성을 측정하였으며, 열 안정성 측정에 의한 분해정도는 고성능 액체크로마토그래피(HPLC, High Performance Liquid Chromatography)로 측정하였다.In addition, the thermal stability was measured while standing in a 65 ℃ thermostat in order to determine the storage stability of the prepared solution, the decomposition degree by the thermal stability measurement was measured by High Performance Liquid Chromatography (HPLC).
이상의 실시예에서 살펴본 바와 같이, 상기 화학식 1로 표시되는 3-이소티아졸론 화합물이 용해되어 있는 용액에 본 발명이 특별히 선정한 탈색제를 일정량 함유시키게 되면 안정성에 영향을 주지 않고 탈색 효과가 우수한 3-이소티아졸론 용액 조성물을 얻을 수 있다.As described in the above examples, when a certain amount of the decolorizing agent specifically selected by the present invention is contained in the solution in which the 3-isothiazolone compound represented by Chemical Formula 1 is dissolved, 3-isochrome having excellent decolorizing effect without affecting stability Thiazolone solution compositions can be obtained.
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