CA2111525A1 - Preservative compositions - Google Patents
Preservative compositionsInfo
- Publication number
- CA2111525A1 CA2111525A1 CA 2111525 CA2111525A CA2111525A1 CA 2111525 A1 CA2111525 A1 CA 2111525A1 CA 2111525 CA2111525 CA 2111525 CA 2111525 A CA2111525 A CA 2111525A CA 2111525 A1 CA2111525 A1 CA 2111525A1
- Authority
- CA
- Canada
- Prior art keywords
- preservative
- particles
- compositions
- particle size
- present
- 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.)
- Abandoned
Links
- 239000003755 preservative agent Substances 0.000 title claims abstract description 19
- 230000002335 preservative effect Effects 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 239000002245 particle Substances 0.000 claims abstract description 28
- 239000003607 modifier Substances 0.000 claims abstract description 12
- 239000006185 dispersion Substances 0.000 claims abstract description 3
- 239000003205 fragrance Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000004615 ingredient Substances 0.000 abstract description 3
- -1 polyoxyethylene Polymers 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- AMGNHZVUZWILSB-UHFFFAOYSA-N 1,2-bis(2-chloroethylsulfanyl)ethane Chemical compound ClCCSCCSCCCl AMGNHZVUZWILSB-UHFFFAOYSA-N 0.000 description 1
- IQXJCCZJOIKIAD-UHFFFAOYSA-N 1-(2-methoxyethoxy)hexadecane Chemical compound CCCCCCCCCCCCCCCCOCCOC IQXJCCZJOIKIAD-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100000210 Mus caroli Orm8 gene Proteins 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 229940078456 calcium stearate Drugs 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229950009789 cetomacrogol 1000 Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940107161 cholesterol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 239000008387 emulsifying waxe Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 239000008011 inorganic excipient Substances 0.000 description 1
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000002398 sedimentation field-flow fractionation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
ABSTRACT
The present invention is directed to a preservative composition comprising an aqueous dispersion of particles of at least one preservative wherein said particles have a surface modifier adsorbed on the surface thereof in an amount sufficient to achieve a particle size of less than about 400 nanometers (nm). The compositions of the present invention can contain other conventional ingredients.
The present invention is directed to a preservative composition comprising an aqueous dispersion of particles of at least one preservative wherein said particles have a surface modifier adsorbed on the surface thereof in an amount sufficient to achieve a particle size of less than about 400 nanometers (nm). The compositions of the present invention can contain other conventional ingredients.
Description
2 ~ 2 ~
PRESERVATIVE COMPOSITIONS
c Field of the Invention The present invention relatss to preservative containing compositions for uso in household and industrial products.
~; 5 ~ackaround o~ the In~en~ion A variety of preservative agent~ havs been ~ formulated into compositions that are marketed as ;; household products such as cleaners, floor polishes, 0 painta, stains, cosmetics, personal care products and industrial fluids such as metal working, secondary oil recovery, cooling tower, and pulp and paper procQssing composition~.
It is an object of the present invention to increase the dispersibility of these agents in aqueous media while minimizing or eliminating the need for organic solvent~.
Summarv of the Invention The present invention is directed to a preservative composition that comprises an aqueous dispersion of particles of at least one preservative wherein said particles have a surface modifier adsorbed on the surface thereof in an amount sufficient to achieve a particle size of less than about 400 nanometers (nm). The compositions of tha present `, invention can contain other conventional ingredients that are used in such compositions.
,~
; 30 Detailed ~escriDtio~ of the Invention The compositions of the invention comprise .~
; preservative containing nanoparticles. The preservative can be any of a variety of compounds such a~ glycerol, .
.
.
, ~ .~
. ;, .
~ "''' ' ",~; ~ ~
~,:
~: 2 ~
monolaurate, parabens, pyrthione~, and insoluble guaternary amine complexes.
The particles of this invention contain a ; discrete phas~ of a pre~ervative a described abovehaving a RurfacQ modifier adsorbed on the sur~ace thereo~. Use~ul surface modifiers are believed to include those which physically adhere to the sur~ace o~
the preservativ~ but do not chemically bond to the ~ preservative.
PRESERVATIVE COMPOSITIONS
c Field of the Invention The present invention relatss to preservative containing compositions for uso in household and industrial products.
~; 5 ~ackaround o~ the In~en~ion A variety of preservative agent~ havs been ~ formulated into compositions that are marketed as ;; household products such as cleaners, floor polishes, 0 painta, stains, cosmetics, personal care products and industrial fluids such as metal working, secondary oil recovery, cooling tower, and pulp and paper procQssing composition~.
It is an object of the present invention to increase the dispersibility of these agents in aqueous media while minimizing or eliminating the need for organic solvent~.
Summarv of the Invention The present invention is directed to a preservative composition that comprises an aqueous dispersion of particles of at least one preservative wherein said particles have a surface modifier adsorbed on the surface thereof in an amount sufficient to achieve a particle size of less than about 400 nanometers (nm). The compositions of tha present `, invention can contain other conventional ingredients that are used in such compositions.
,~
; 30 Detailed ~escriDtio~ of the Invention The compositions of the invention comprise .~
; preservative containing nanoparticles. The preservative can be any of a variety of compounds such a~ glycerol, .
.
.
, ~ .~
. ;, .
~ "''' ' ",~; ~ ~
~,:
~: 2 ~
monolaurate, parabens, pyrthione~, and insoluble guaternary amine complexes.
The particles of this invention contain a ; discrete phas~ of a pre~ervative a described abovehaving a RurfacQ modifier adsorbed on the sur~ace thereo~. Use~ul surface modifiers are believed to include those which physically adhere to the sur~ace o~
the preservativ~ but do not chemically bond to the ~ preservative.
3 lo Suitable surface modifiers can preferably be ~J selected from known organic and inorganic excipient~.
~i Such excipients lnclude various polymers, low molecular weight oligomers, natural products and sur~actants.
Preferred surface modifiers include nonionic and anionic surfactants. Representative examples o~ excipients include gelatin, casein, lecithin (phosphatides), gum acacia, cholesterol, tragacanth, stearic acid, benzalkonium chloride, calcium stearate, glyceryl ~ monostearate, cetostearl alcohol, cetomacrogol ;~ 20 emulsifying wax, sorbitan esters, polyoxyethylene alkyl ethers, e.g., macrogol ethers such as cetomacrogol 1000, polyoxyethylene castor oil derivatives, polyoxyethylene sorbitan fatty acid esters~ e.g., the commercially availabl~ Tweens, polyethylene glycols, polyoxyethylene stearates, colloidol silicon dioxide, phosphates, odium dodecylsulfate, carboxymethylcellulose calcium, carboxymethylcellulose sodium, methylcellulose hydroxyethylcellulose, hydroxypropylcellulose, `~ hydroxypropylmethycellulose phthalate, noncrystalline cellulo3e, magnesium aluminum silicate, triethanolamine, polyvinyl alcohol, and polyvinylpyrrolidone (PVP). Most o~ these excipients ara described in detail in the Handbook of Pharmaceutical Excipients, published jointly by the American Pharmaceutical Association and The ~ 35 Pharmaceutical Society o~ Great Britain, the i ,. !, " ' ~. . ' ~
'. " `
; 2 ~ 2 . ., ',3, Pharmaceutical Press, 1986, the disclosure o~ which is~, here~y incorporated by re~erence in it5 entirety. The surfacQ modi~iers are commercially available and/or can b~ prepared by techniques known in the art.
` 5 The surface modifier is adsorbed on the -1, surface o~ the preservative in an amount sufficient to maintain an effective averag~ particle ~ize of less than about 400 nm. The sur~ace modifier does not chemically react with the preservative or itsel~. Furthermore, the individually adsorbed molecules of the sur~ac~ modi~ier are essentially free of intermolecular crosslinkages.
As used herein, particle siz~ refers to a number averag~ particle size as measured by conventional particle size measuring techniques well known to those skilled in the art, such as sedimentation field flow fractionation, photon correlation spectroscopy, or disk centrifugation. By "an effectiv4 average particle size of les~ than about 400 nm" it is meant that at least 90%
of the particles have a weight average particle size of les~ than about 400 nm when measured by the above-noted techniques. In preferred embodiments of the invention, the effeçtive average particle size is less than about 250 nm. In some embodiments of the invention, an effective averag~ particle size of less than about 100 nm has been achieved. With reference to the effectiv~
average particl~ size, it is preferred that at least 95%
and, more preferably, at least 99% o~ the particle~ hav~
-~ a particle size less than the effective average, e.g., 400 nm. In particu~arly pre~erred embodiments, .~
essentially all of the particles have a size les than 400 nm. In some embodiments, essentially all of the particles have a size less than 250 n~.
The particles of this invention can be prepared by a method comprising the steps of dispersing .~i , .
~i 35 a preservative in a liquid dispersion medium and .
.
,, ,; .,: . ,, :.'.. : . . :
.. . .
. ,.; . . .
, ...
`, 2 ~
.,,i ~ .
`~; applyin~ mechanical mean~ in the prQsence o~ grinding ~`''!'' media to reduco th~ particle 8iZR 0~ the in~ction -i control agent to an effective avQrage particle size of ~, le88 than about 400 nm. The particle~ can be reduced in size in the presenc~ o~ ~ surfacQ modi~ier.
~lternatively, th~ particle~ can bQ contacted with a surface modifi~r ~fter attrition.
These mQthods are described in detail in U.S.
Patent No. 5,145,684.
The relative amount o~ preservativ~ and ~urface modi~ier can vary widely and thQ optimal amount o~ the surface modifier can depend, for exampl~, upon the particular preservative and sur~ac~ modi~ier ; selected, the critical micelle concentrat~on of the surface modifier if it ~orm8 micellQs, etc. The surfaca modifier prefer~bly i~ present in an amount of about 0.1-~0 mg per ~guare meter surface ~rea of the :~ halohydanto~n. The surfaco modifiQr can be present in an amount of 0.1-99.995%, preferably 20-60% by weight based on the total weight of the formulation.
m e nanoparticles of th~ present invention can be incorporated into conventional preserving and s~ microbiocidQ compositions, a3 ~or exampl~, thos~
disclosed in U.S. Patent Nos. 4,040,977; 4,379,137;
~i Such excipients lnclude various polymers, low molecular weight oligomers, natural products and sur~actants.
Preferred surface modifiers include nonionic and anionic surfactants. Representative examples o~ excipients include gelatin, casein, lecithin (phosphatides), gum acacia, cholesterol, tragacanth, stearic acid, benzalkonium chloride, calcium stearate, glyceryl ~ monostearate, cetostearl alcohol, cetomacrogol ;~ 20 emulsifying wax, sorbitan esters, polyoxyethylene alkyl ethers, e.g., macrogol ethers such as cetomacrogol 1000, polyoxyethylene castor oil derivatives, polyoxyethylene sorbitan fatty acid esters~ e.g., the commercially availabl~ Tweens, polyethylene glycols, polyoxyethylene stearates, colloidol silicon dioxide, phosphates, odium dodecylsulfate, carboxymethylcellulose calcium, carboxymethylcellulose sodium, methylcellulose hydroxyethylcellulose, hydroxypropylcellulose, `~ hydroxypropylmethycellulose phthalate, noncrystalline cellulo3e, magnesium aluminum silicate, triethanolamine, polyvinyl alcohol, and polyvinylpyrrolidone (PVP). Most o~ these excipients ara described in detail in the Handbook of Pharmaceutical Excipients, published jointly by the American Pharmaceutical Association and The ~ 35 Pharmaceutical Society o~ Great Britain, the i ,. !, " ' ~. . ' ~
'. " `
; 2 ~ 2 . ., ',3, Pharmaceutical Press, 1986, the disclosure o~ which is~, here~y incorporated by re~erence in it5 entirety. The surfacQ modi~iers are commercially available and/or can b~ prepared by techniques known in the art.
` 5 The surface modifier is adsorbed on the -1, surface o~ the preservative in an amount sufficient to maintain an effective averag~ particle ~ize of less than about 400 nm. The sur~ace modifier does not chemically react with the preservative or itsel~. Furthermore, the individually adsorbed molecules of the sur~ac~ modi~ier are essentially free of intermolecular crosslinkages.
As used herein, particle siz~ refers to a number averag~ particle size as measured by conventional particle size measuring techniques well known to those skilled in the art, such as sedimentation field flow fractionation, photon correlation spectroscopy, or disk centrifugation. By "an effectiv4 average particle size of les~ than about 400 nm" it is meant that at least 90%
of the particles have a weight average particle size of les~ than about 400 nm when measured by the above-noted techniques. In preferred embodiments of the invention, the effeçtive average particle size is less than about 250 nm. In some embodiments of the invention, an effective averag~ particle size of less than about 100 nm has been achieved. With reference to the effectiv~
average particl~ size, it is preferred that at least 95%
and, more preferably, at least 99% o~ the particle~ hav~
-~ a particle size less than the effective average, e.g., 400 nm. In particu~arly pre~erred embodiments, .~
essentially all of the particles have a size les than 400 nm. In some embodiments, essentially all of the particles have a size less than 250 n~.
The particles of this invention can be prepared by a method comprising the steps of dispersing .~i , .
~i 35 a preservative in a liquid dispersion medium and .
.
,, ,; .,: . ,, :.'.. : . . :
.. . .
. ,.; . . .
, ...
`, 2 ~
.,,i ~ .
`~; applyin~ mechanical mean~ in the prQsence o~ grinding ~`''!'' media to reduco th~ particle 8iZR 0~ the in~ction -i control agent to an effective avQrage particle size of ~, le88 than about 400 nm. The particle~ can be reduced in size in the presenc~ o~ ~ surfacQ modi~ier.
~lternatively, th~ particle~ can bQ contacted with a surface modifi~r ~fter attrition.
These mQthods are described in detail in U.S.
Patent No. 5,145,684.
The relative amount o~ preservativ~ and ~urface modi~ier can vary widely and thQ optimal amount o~ the surface modifier can depend, for exampl~, upon the particular preservative and sur~ac~ modi~ier ; selected, the critical micelle concentrat~on of the surface modifier if it ~orm8 micellQs, etc. The surfaca modifier prefer~bly i~ present in an amount of about 0.1-~0 mg per ~guare meter surface ~rea of the :~ halohydanto~n. The surfaco modifiQr can be present in an amount of 0.1-99.995%, preferably 20-60% by weight based on the total weight of the formulation.
m e nanoparticles of th~ present invention can be incorporated into conventional preserving and s~ microbiocidQ compositions, a3 ~or exampl~, thos~
disclosed in U.S. Patent Nos. 4,040,977; 4,379,137;
4,996,052 and S,023,267, th~ disclosure~ o~ which are incorporated herein. Additives such as perfumes, anticorrosivQ agent Q.g., benzotriazole, fungicides, biocide~ and other similar additives can b~ incorporated ~ in thesQ compositions.
-, 30 Representativ~ preservative~ lnclud~ a thiol~n 1 of the formul~:
,` ,~
~j'' x~o , . ' ;; ", :., . ~ .
: ,~, , : : :, ,,,~ .
:: ., . ~
. "i",.
-, 30 Representativ~ preservative~ lnclud~ a thiol~n 1 of the formul~:
,` ,~
~j'' x~o , . ' ;; ", :., . ~ .
: ,~, , : : :, ,,,~ .
:: ., . ~
. "i",.
- 5 ~ 2 ~
. ~ .
;-- wherein each o~ X and Y, which may b~ the ~ame or ~ di~ferent represents fluorin~, chlorine or bromine, an '3'',,~ alXylenebisthiocyanat~ and a 2-N-alky1-4-isothiazolin-3-`'-'~1 on~;
~ compound sQlected from the group con~isting o~ polymeric quaternary a~monium compound~ having the formula:
Rs-hO-CUI-A-cH~ ~ hO-Z-NO-CH~-A-CH~ R~.(2~+2)X~
~h~--Z--l'JO--CH2--A--CHI~ .2nX~
wherein Rl and R2, which can b~ tho same or differ~nt are alkyl having from 1 to 20 carbon atoms an~ having r"~ 20 from 0 to 1 hydroxyl substituent, benzyl, benzyl bearing on the benzene moiety one alkyl having from 2 to 20 ~ carbon a~oms; h~, R4 and R5, which can be th~ oam~ or- di~ferent, ar~ alkyl having ~rom 1 to 20 carbon atoms and having from 0 to 1 hydroxyl substituent, or R3 and - 25 R~ taken together with th~ nitrogen to which they are ~ attached ~orm a ~aturat~d het2rocyclic ring having from .ii 5 to 7 ring ato~s; Z and A, which can be the same or different, are divalent alkylen~ radicals o~ 2 to 10 carbon atom~ interrupted by from 0 to 1 oxygen atom and containing ~rom 0 to 2 ethylenic double bonds; n i3 a whols number ~rom 2 to 30; and X i~ ~ halogen; and ;:~
.. , ' ' ,';
~' ~ . . -.~ .... .
~ 6 -- ..
a 3-i~othiazolone having the ~ormul~:
R'~N--Y
;
wherein Y i8 ~lkyl having from 1 to 18 carbon atoms, . cyclohexyl, phenyl, halophenyl, benzyl or halobenzyl, and R', which can b~ the same or different, ar~
hydrogen, halogen, ~lXyl having from 1 to 6 carbon ~;~!; atom~, alkenyl o~ 2 to 6 carbon atoms or phenyl, or R
.~. and R' togeth~r with the carbon atom3 to which they are ,~.'r att~ched form a benzene ring, or a salt thereof with ~trong acid, or a 3-isothiazolone metal salt complex ~: 15 having the formula:
,:
~a [ s ' Yl (Ml~",) . 20 . wherein Y, R and R' are a~ de~ined above, M is a cation , o~ calcium or magnesium, B i~ a chloride anion or .~ nitrate anion, a i3 the whole number 1 or 2, and ~ i~
the nu~ber 2: wherein the ratio of component (a) to component ~b) is ~rom 1:200 to 200:1: and phosphate derivative~ o~ the following general `; formula:
,, ,~
~.~. U
3 0 X ' ~ OR
OH
`,i - wherein:
-.
' . "
~, -~: :
. ~ ~ - ..
. ,G. ,' ' ~ :
2 i q - 7 -,.......................................................................... .
~
R may be alkyl, aryl, aralkyl and alkaryl group~ including, but not limited to, straight chain, branched chain or cyclic alkyl groups having fro~ 1 to 24 carbon atoms, polyoxyethylene or polyoxypropylene having from 2 to 32 ethylene oxide or propylene oxide units respectively, alkyl phenoxy polyoxyethylene containing 2 to 32 ethyleno oxide unit~, alkyl phenoxy polyoxyethylen~ containing ethylene oxide units and 1 to 24 carbon atoms in the phenolic alkyl chain, and polyhydroxy compounds, including but not limited to, 3 ethylene glycol, ylycerol or sorbitol.
X is selectQd from the group consisting of Group IA metals, Group IIA metals, tr~nsition metals, hydrogen and an organic ion. The positively charged ion is not necessary for microbiocidal activity.
Th~ compositions of the present invention can be illustrated by the following representative example.
Example 1 Preservative Floor Polish Ingredient Wt. %
Water 47 Nanoparticle preservatives0.01 - 1 Premixed plasticizer (Tributoxyethyl Phosphate) 1.2 `~ Diethylene glycol monomethyl ether 5.0 1% FC-129 ~olution 0.5 Texanol 0.34 Methyl Pyrolidone 0.55 Acrylic Polymer 33 Rosin Ester 3.3 Polyethylene Emulsion 8.2 The foregoing specification, including tho specific embodiments and example i8 intended to be illustrative of the present invention and is not to be taken a~ limiting. Numerous other variation~ and modifications can be effected without departing from the true spirit and scope of the present invention.
,~
~. , .
.
,~ .
. .
.,:
~, . ~ . .
. ~ .
;-- wherein each o~ X and Y, which may b~ the ~ame or ~ di~ferent represents fluorin~, chlorine or bromine, an '3'',,~ alXylenebisthiocyanat~ and a 2-N-alky1-4-isothiazolin-3-`'-'~1 on~;
~ compound sQlected from the group con~isting o~ polymeric quaternary a~monium compound~ having the formula:
Rs-hO-CUI-A-cH~ ~ hO-Z-NO-CH~-A-CH~ R~.(2~+2)X~
~h~--Z--l'JO--CH2--A--CHI~ .2nX~
wherein Rl and R2, which can b~ tho same or differ~nt are alkyl having from 1 to 20 carbon atoms an~ having r"~ 20 from 0 to 1 hydroxyl substituent, benzyl, benzyl bearing on the benzene moiety one alkyl having from 2 to 20 ~ carbon a~oms; h~, R4 and R5, which can be th~ oam~ or- di~ferent, ar~ alkyl having ~rom 1 to 20 carbon atoms and having from 0 to 1 hydroxyl substituent, or R3 and - 25 R~ taken together with th~ nitrogen to which they are ~ attached ~orm a ~aturat~d het2rocyclic ring having from .ii 5 to 7 ring ato~s; Z and A, which can be the same or different, are divalent alkylen~ radicals o~ 2 to 10 carbon atom~ interrupted by from 0 to 1 oxygen atom and containing ~rom 0 to 2 ethylenic double bonds; n i3 a whols number ~rom 2 to 30; and X i~ ~ halogen; and ;:~
.. , ' ' ,';
~' ~ . . -.~ .... .
~ 6 -- ..
a 3-i~othiazolone having the ~ormul~:
R'~N--Y
;
wherein Y i8 ~lkyl having from 1 to 18 carbon atoms, . cyclohexyl, phenyl, halophenyl, benzyl or halobenzyl, and R', which can b~ the same or different, ar~
hydrogen, halogen, ~lXyl having from 1 to 6 carbon ~;~!; atom~, alkenyl o~ 2 to 6 carbon atoms or phenyl, or R
.~. and R' togeth~r with the carbon atom3 to which they are ,~.'r att~ched form a benzene ring, or a salt thereof with ~trong acid, or a 3-isothiazolone metal salt complex ~: 15 having the formula:
,:
~a [ s ' Yl (Ml~",) . 20 . wherein Y, R and R' are a~ de~ined above, M is a cation , o~ calcium or magnesium, B i~ a chloride anion or .~ nitrate anion, a i3 the whole number 1 or 2, and ~ i~
the nu~ber 2: wherein the ratio of component (a) to component ~b) is ~rom 1:200 to 200:1: and phosphate derivative~ o~ the following general `; formula:
,, ,~
~.~. U
3 0 X ' ~ OR
OH
`,i - wherein:
-.
' . "
~, -~: :
. ~ ~ - ..
. ,G. ,' ' ~ :
2 i q - 7 -,.......................................................................... .
~
R may be alkyl, aryl, aralkyl and alkaryl group~ including, but not limited to, straight chain, branched chain or cyclic alkyl groups having fro~ 1 to 24 carbon atoms, polyoxyethylene or polyoxypropylene having from 2 to 32 ethylene oxide or propylene oxide units respectively, alkyl phenoxy polyoxyethylene containing 2 to 32 ethyleno oxide unit~, alkyl phenoxy polyoxyethylen~ containing ethylene oxide units and 1 to 24 carbon atoms in the phenolic alkyl chain, and polyhydroxy compounds, including but not limited to, 3 ethylene glycol, ylycerol or sorbitol.
X is selectQd from the group consisting of Group IA metals, Group IIA metals, tr~nsition metals, hydrogen and an organic ion. The positively charged ion is not necessary for microbiocidal activity.
Th~ compositions of the present invention can be illustrated by the following representative example.
Example 1 Preservative Floor Polish Ingredient Wt. %
Water 47 Nanoparticle preservatives0.01 - 1 Premixed plasticizer (Tributoxyethyl Phosphate) 1.2 `~ Diethylene glycol monomethyl ether 5.0 1% FC-129 ~olution 0.5 Texanol 0.34 Methyl Pyrolidone 0.55 Acrylic Polymer 33 Rosin Ester 3.3 Polyethylene Emulsion 8.2 The foregoing specification, including tho specific embodiments and example i8 intended to be illustrative of the present invention and is not to be taken a~ limiting. Numerous other variation~ and modifications can be effected without departing from the true spirit and scope of the present invention.
,~
~. , .
.
,~ .
. .
.,:
~, . ~ . .
Claims
1. A preservative composition comprising an aqueous dispersion of particles of at least one preservative wherein said particles have a surface modifier adsorbed on the surface thereof in an amount sufficient to achieve a particle size of less than about 400 nanometers (nm), a surfactant, a dye and a fragrance.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US99143192A | 1992-12-16 | 1992-12-16 | |
US07/991,431 | 1992-12-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2111525A1 true CA2111525A1 (en) | 1994-06-17 |
Family
ID=25537210
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA 2111525 Abandoned CA2111525A1 (en) | 1992-12-16 | 1993-12-15 | Preservative compositions |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA2111525A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003100214A1 (en) * | 2002-05-24 | 2003-12-04 | 3M Innovative Properties Company | Use of surface-modified nanoparticles for oil recovery |
-
1993
- 1993-12-15 CA CA 2111525 patent/CA2111525A1/en not_active Abandoned
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003100214A1 (en) * | 2002-05-24 | 2003-12-04 | 3M Innovative Properties Company | Use of surface-modified nanoparticles for oil recovery |
US7033975B2 (en) | 2002-05-24 | 2006-04-25 | 3M Innovative Properties Company | Use of surface-modified nanoparticles for oil recovery |
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