MXPA00000625A - Water-stabilized organosilane compounds and their use - Google Patents
Water-stabilized organosilane compounds and their useInfo
- Publication number
- MXPA00000625A MXPA00000625A MXPA/A/2000/000625A MXPA00000625A MXPA00000625A MX PA00000625 A MXPA00000625 A MX PA00000625A MX PA00000625 A MXPA00000625 A MX PA00000625A MX PA00000625 A MXPA00000625 A MX PA00000625A
- Authority
- MX
- Mexico
- Prior art keywords
- ch3ch2
- alkyl
- organosilane
- independently
- 3nhc
- Prior art date
Links
- -1 organosilane compounds Chemical class 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 claims abstract description 143
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 100
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 81
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 64
- 239000000758 substrate Substances 0.000 claims abstract description 63
- 238000002156 mixing Methods 0.000 claims abstract description 27
- 150000005677 organic carbonates Chemical class 0.000 claims abstract description 24
- 235000013305 food Nutrition 0.000 claims abstract description 22
- 238000000576 coating method Methods 0.000 claims abstract description 12
- 239000011248 coating agent Substances 0.000 claims abstract description 11
- 238000004043 dyeing Methods 0.000 claims abstract description 9
- 239000012530 fluid Substances 0.000 claims abstract description 6
- 239000004816 latex Substances 0.000 claims abstract description 5
- 229920000126 latex Polymers 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 94
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 65
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 230000000845 anti-microbial effect Effects 0.000 claims description 41
- 239000000243 solution Substances 0.000 claims description 38
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 30
- 229910000077 silane Inorganic materials 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 229920000151 polyglycol Polymers 0.000 claims description 21
- 239000010695 polyglycol Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 239000004599 antimicrobial Substances 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 18
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000000962 organic group Chemical group 0.000 claims description 16
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- WSFMFXQNYPNYGG-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC WSFMFXQNYPNYGG-UHFFFAOYSA-M 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 239000004567 concrete Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011152 fibreglass Substances 0.000 claims description 9
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 claims description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 150000007942 carboxylates Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000004579 marble Substances 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- 230000002787 reinforcement Effects 0.000 claims description 4
- 239000002356 single layer Substances 0.000 claims description 4
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000000227 bioadhesive Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical group CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 claims description 3
- 229950010007 dimantine Drugs 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 3
- 235000013824 polyphenols Nutrition 0.000 claims description 3
- 239000003755 preservative agent Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 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 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- QXDDDCNYAAJLBT-UHFFFAOYSA-N 3-chloropropyl(trimethyl)silane Chemical compound C[Si](C)(C)CCCCl QXDDDCNYAAJLBT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- VAGHXUBNGZSYFM-UHFFFAOYSA-N CC1=CC=C(CC[SiH2]C(Cl)Cl)C=C1 Chemical compound CC1=CC=C(CC[SiH2]C(Cl)Cl)C=C1 VAGHXUBNGZSYFM-UHFFFAOYSA-N 0.000 claims description 2
- LWDNJHRXSHCRNP-UHFFFAOYSA-N CCCC(C=C(CCl)C=C1)=C1[Si](Cl)(Cl)Cl Chemical compound CCCC(C=C(CCl)C=C1)=C1[Si](Cl)(Cl)Cl LWDNJHRXSHCRNP-UHFFFAOYSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 2
- 229910003910 SiCl4 Inorganic materials 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 2
- 229930016911 cinnamic acid Natural products 0.000 claims description 2
- 235000013985 cinnamic acid Nutrition 0.000 claims description 2
- 239000003479 dental cement Substances 0.000 claims description 2
- BUMGIEFFCMBQDG-UHFFFAOYSA-N dichlorosilicon Chemical compound Cl[Si]Cl BUMGIEFFCMBQDG-UHFFFAOYSA-N 0.000 claims description 2
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 claims description 2
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 claims description 2
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 claims description 2
- 229940089951 perfluorooctyl triethoxysilane Drugs 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims description 2
- 238000010186 staining Methods 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- HLWCOIUDOLYBGD-UHFFFAOYSA-N trichloro(decyl)silane Chemical compound CCCCCCCCCC[Si](Cl)(Cl)Cl HLWCOIUDOLYBGD-UHFFFAOYSA-N 0.000 claims description 2
- AVYKQOAMZCAHRG-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AVYKQOAMZCAHRG-UHFFFAOYSA-N 0.000 claims description 2
- 229910003204 NH2 Inorganic materials 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- LOOUJXUUGIUEBC-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propane-1-thiol Chemical compound COC(OC)[SiH2]CCCS LOOUJXUUGIUEBC-UHFFFAOYSA-N 0.000 claims 1
- 239000004721 Polyphenylene oxide Chemical group 0.000 claims 1
- 229910003822 SiHCl3 Inorganic materials 0.000 claims 1
- 230000006750 UV protection Effects 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- AXPYABZPAWSUMG-UHFFFAOYSA-M didecyl-methyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical group [Cl-].CCCCCCCCCC[N+](C)(CCC[Si](OC)(OC)OC)CCCCCCCCCC AXPYABZPAWSUMG-UHFFFAOYSA-M 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 claims 1
- MTNTUAHMWISEEF-UHFFFAOYSA-N ethenyl-methyl-bis(trimethylsilyloxy)silane Chemical compound C[Si](C)(C)O[Si](C)(C=C)O[Si](C)(C)C MTNTUAHMWISEEF-UHFFFAOYSA-N 0.000 claims 1
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 229920000570 polyether Chemical group 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- FCMZRNUHEXJWGB-UHFFFAOYSA-N trichloro(cyclopentyl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCCC1 FCMZRNUHEXJWGB-UHFFFAOYSA-N 0.000 claims 1
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical compound Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 18
- 239000000047 product Substances 0.000 description 94
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000010348 incorporation Methods 0.000 description 12
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- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
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- 229910052740 iodine Inorganic materials 0.000 description 8
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- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 5
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- 238000004140 cleaning Methods 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 230000002035 prolonged effect Effects 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
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- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
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- 231100000331 toxic Toxicity 0.000 description 3
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- 235000013311 vegetables Nutrition 0.000 description 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 description 2
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Abstract
The composition formed by mixing an organosilane with an organic carbonate. Water-stabilized organosilane compounds. A water stable composition made from the organic carbonate and organosilane composition and water. A method of treating a substrate by mixing or contacting the substrate with the product, compound, or composition of this invention for a period of time sufficient for treatment of the substrate. A treated substrate having adhered thereto the product, compound, or composition of this invention. A method of dyeing and treating a substrate. A method of antimicrobially treating a food article. A method of antimicrobially coating a fluid container. A method of antimicrobially coating a latex medical article.
Description
ORGANOSILANO COMPOUNDS STABLE TO WATER AND ITS USE
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
The invention relates to organosilane compounds, products and methods for their use. In particular, this invention provides water-stable organosilane compounds, products and compositions for treating various substrates; articles treated with the compounds, products and compositions; and methods of treatment using the compounds, products and compositions.
BACKGROUND
The organosilanes of the general formula RnSiX4-n where n is an integer from 0 to 3, but very generally from 0 to 2 (where when n is 3 the organosilanes can only be dimerized); R is a non-hydrolysable organic group, such as, but not limited to alkyl, aromatic, organofunctional or a combination thereof, and X is alkoxy, such as methoxy or ethoxy, I are subject to undergoing polycondensation making said organosilanes unstable in water during commercially important periods. In addition, X can be a halogen such as Cl, Br or I and is similarly released as HCl, HBr or Hl. For said organosilanes, the X portion reacts with various hydroxyl-containing molecules in aqueous media to liberate methanol, ethanol, HCl, HBr, Hl, H2O, acetic acid or an unsubstituted or substituted carboxylic acid and to form the hydroxylated compound but subject to condensation. For the organosilanes RnSiX4_n, where n is an integer from 0 to 2, the hydrolysis of the first two X groups with water produces a species containing -Si (OH) 2- units which can be self-condensed through the hydroxyl portions to linear and / or cyclic oligomers possessing the partial structure HO-S i- (0-Si) mm-0-Si-0-Si-0-Si-OH, where mm is an integer such that forms an oligomer. For those cases, RSIX3, the hydrolysis of the third group X generates a silanotriol (RSi (OH) 3) which produces insoluble organosilicon polymers through linear and / or cyclic self-condensation of the Si (OH) units. This water induced auto-condensation generally prevents the storage of most of the organosilanes RnSiX4_n, where n varies from 0 to 2, inclusive, in water. Except for some organosilanes that may be stable in highly diluted solutions at specific pH scales, the use of water solutions of most organosilanes requires the use of freshly prepared solutions. A commercially important example of an organosilane suffering from such undesirable self-condensation is the Dow Corning 5700 antimicrobial (Dow Corning Corporation, Midland, Ml). The literature describes the active ingredient of Dow Corning 5700 as 3- (trimethoxysilyl) propyl-dimethyloctadecylammonium chloride. However, in aqueous media it is believed that the correct active ingredient is most likely 3- (trihydroxysilyl) propyl-methylmethyldecylammonium chloride. However, the Dow Corning 5700 is an integrated water-activated antimicrobial system that is capable of binding to a wide variety of natural and synthetic substrates, including fibers and fabrics, to produce a durable surface or fabric coating. The 3- (trimethoxysilyl) propyl-dimethyloctacylammonium chloride is prepared by quatemization of dimethyloctadecylamine with 3-chloropropyltrimethoxysilane. The quaternary ammonium portion of the hydrocarbon chain of C- | s of the molecule possesses long-acting antimicrobial properties and provides initial association with the surface of the substrate through ionic bonds and / or electrostatic interaction. Preferably, the treated surface is permanently coated with an octadecylammonium ion bonded by covalent bond, providing a durable, long-acting antimicrobial coating that escapes from destroying microbes that come in contact with the surface. Unfortunately, as noted above, organosilanes in water, such as the activated mixture of 3- (trimethoxysilyl) propyl-dimethyloctadecylammonium chloride and water, are generally unstable and subject to self-condensation. For example, the mixture of 3- (trimethoxysilyl) propyl-dimethyloctadecylammonium chloride and water begins to lose effectiveness in as little as four to eight hours. Gel formation in this formulation and similar silane formulations in water begins to occur in even shorter times. The limitations of said organosilanes in aqueous media are further described in U.S. Patent No. 5,411, 585, the content of which is incorporated herein by reference. In addition, said products are notable for the difficulty of agitation during the addition of the silane to water. The use of quaternary ammonium silicon compounds as antimicrobial agents according to the prior art is well known and is taught in a wide variety of United States patents, for example, 3,560,385; 3,794,736; 3,814,739, the content of which is incorporated herein by reference. It is also taught that these compounds possess certain antimicrobial properties that make them valuable and very useful for a variety of surfaces, substrates, instruments and applications (see, for example, U.S. Patent Nos. 3,730,701, 3,794,736, 3,860,709, 4,282,366, 4,504,541. 4,615,937, 4,692,374, 4,408,996 and 4,414,268, the contents of which are incorporated herein by reference). Although these quaternary ammonium silicon compounds have been used to sterilize or disinfect many surfaces, their use is still limited due to their toxicity often as a result of the solvent system used to deliver the compound, the need for a solvent solution (e.g. , antimicrobial agent of Dow Corning 5700 contains approximately 49% methanol), short-term stability (stability of aqueous silane solutions vary from a few hours to several weeks only), and poor water solubility. For example, although 3- (trimethoxysilyl) propyl-dimethyloctadecylammonium chloride does not suffer from insolubility in water, it is difficult to dissolve in water and tends to form lumps before it dissolves slowly. It is unstable in water and because it is shipped in 50% methanol, it is toxic and flammable. Many other antimicrobial silanes, especially quaternary ammonium silicon compounds, also suffer from the problems associated with physical health hazards, for example, precautions must be taken to avoid contact with both skin and eyes, accidental spills to the surrounding area, flammability and the additional manufacturing steps necessary to incorporate said antimicrobial agents into other articles and surfaces, resulting in much higher manufacturing costs. Therefore, there is a need for water-stable organosilane compounds, prolonged shelf life, products and compositions by which upon application of the active portion of the organosilane is operable for the selected application. In addition, there is a need for water-stable organosilane compounds, products and compositions that are essentially non-toxic, non-flammable, uniformly dispersible and simple and economical to use. There is also a need for highly concentrated organosilane compositions which are essentially non-toxic or of low toxicity, non-flammable, uniformly dispersible and simple and economical to use and stable in water when further diluted with water. In the present application, the findings are described that compounds having at least one carbonate group that stabilizes aqueous organosilane solutions. The example of archetype of carbonates useful in accordance with the present invention is propylene carbonate.
BRIEF DESCRIPTION OF THE INVENTION
The present invention meets these needs by providing water-stable organosilane compounds, products (ie, compounds or compositions formed from a specific reaction) and compositions, methods for their use and articles prepared using the compounds, products and compositions. In particular, the present invention provides the product formed by mixing an organosilane of the formula RnSiX4_n wherein n is an integer from 0 to 3, preferably 0 to 2; each R is independently a non-hydrolysable organic group, and each X is independently a hydrolysable group (hereinafter "organosilane of interest"); with an organic carbonate, preferably propylene carbonate. Accordingly, in one embodiment, this invention provides a water stable composition comprising the product or composition of the invention and water. In a further embodiment, the present invention provides a composition for treating a substrate, comprising a vehicle and an effective amount of the product or compound of the invention.
In another embodiment, the present invention provides a method for treating a substrate, which comprises mixing the substrate with a sufficient amount of the product, compound or composition of the invention for a period sufficient to treat the substrate. In another embodiment, the present invention provides a composition for treating a substrate by incorporation into the substrate. In a further embodiment, the present invention provides a composition for treating a substrate by incorporation into a polymer base structure. In a further embodiment, the present invention provides a composition as a concentrated solution, easily diluted with water, which provides a water stable composition. In a further embodiment, the present invention provides a composition as a concentrated solution, which is the product of the synthesis of the compounds it comprises. In a further embodiment, the present invention provides a treated substrate having the product, compound or composition of the invention adhered thereto or dispersed therein. In addition, the present invention provides a method for dyeing and treating a substrate consisting of contacting the substrate with an aqueous composition comprising a water soluble dye suitable for dyeing a substrate and the product formed from the mixture of an organosilane. of interest with an organic carbonate.
A further embodiment of the present invention provides a method of antimicrobial treatment of a substrate selected from the group consisting of a concrete tube, a toothbrush, a food article, a fluid container, a latex medical article, gloves, shoes, a comb, a hairbrush, a denture, an orthodontic device, a spa or pool filter, an air filter, an HVAC air system, a cabin air system, a marble item , a statue, an exposed work of art, a PE, PP or polyester cover, a fiberglass article coated with silicone or TEFLONR, a Dryvitt finish, a stucco finish, combined cotton, a bio-film, a bio-adhesive, a single-layer roof, a para-roof and a fiberglass reinforcement product that consists of contacting the substrate with an effective amount of the product formed from the mixing of an antimicrobial organosilane or of interest with an organic carbonate. In addition, the present invention also provides a method of antimicrobial increase of a rubbing alcohol product, a flower preserver, or a waterproof solution, which consists of mixing an effective amount of the product formed from the product with the product. mixture of an antimicrobial organosilane of interest with organic carbonate. A further embodiment of this invention is a method for making an organosilane of interest from starting materials in an aqueous solution in the presence of an organic carbonate.
Further advantages of the invention will be set forth in part in the following description and in part will be obvious from the description, or may be learned by putting the invention into practice. The advantages of the invention will be understood and achieved by means of the elements and combinations particularly pointed out in the appended claims. It should be understood that both the foregoing general description and the following detailed description are illustrative and explanatory only and do not limit the invention, as claimed.
DETAILED DESCRIPTION OF THE INVENTION
The present invention can be more easily understood by reference to the following detailed description of the preferred embodiments of the invention. Before describing and detailing the compounds, products, compositions and methods of the present invention, it is to be understood that the terminology used herein is for purposes of describing the particular embodiments only and is not intended to be limiting. It should also be understood that the material included under the definition of certain terms, in some cases may fall under other terms as well. It should be noted that in using the specification and the appended claims, the singular forms "a, an and, the" include plural equivalents unless the context clearly dictates otherwise.
Throughout this application, where references are made to the publications, the descriptions of these publications are incorporated by reference in their entirety in this application. The term "alkyl" as used herein refers to a branched or unbranched saturated hydrocarbon group of 1 to 24 carbon atoms, such as methyl ("Me"), ethyl ("Et"), n-propyl,! sopropyl, n-butyl, isobutyl, t-butyl, octyl, decyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like. "Alkyl alcohol" as used herein refers to an alkyl having attached thereto one or more hydroxyl portions, such as, but not limited to -CH 2 CH 2 OH, CH 2 CH (OH) CH 3, CH 2 OH, CH 2 CH 2 CH 2 OH, CH 2 CH 2 CH (OH CH3, CH2CH2CH (OH) CH2? H or CH2CH (OH) CH (OH) CH3. The term "alkoxy" as used herein refers to an alkyl group attached through a single terminal ether bond, ie, an "alkoxy" group can be defined as -OR wherein R is alkyl as Defined before. "Glycol", as used herein, refers to glycol compounds, including but not limited to ethylene glycol, propylene glycol, butylene glycol, isobutylene glycol or hexylene glycol. "Polyglycol" as used herein refers to a compound or portion that adopts the polymeric form of glycol, such as, but not limited to, polyethylene glycol or polypropylene glycol. The polyglycol also includes, for example, block and copolymers of ethylene glycol and propylene glycol. The polyglycols useful in the present invention can have an average molecular weight of up to 10,000 g / mol. "Polyalkyl ethers" refers to alkyls or alkyl alcohols interconnected by multiple ether linkages or otherwise possessing such linkages. The polyalkyl ethers useful in the present invention may have an average molecular weight of up to about 10,000 g / mol. "Alkyl glycol" as used herein, refers to an alkyl connected to a glycol through an ether linkage. An example of an alkyl glycol includes, but is not limited to, butyl glycol. "Alkylpolyglycol" as used herein refers to alkyl connected to a polyglycol through an ether linkage. The alkyl polyglycol compounds useful in the present invention can have an average molecular weight of up to 10,000 g / mol. As used herein, "optional" or "optionally" means that the subsequently described event or circumstance may or may not occur, and that the description includes instances where said event or circumstance occurs and cases where it does not occur. For example, the phrase "optionally substituted lower alkyl" means that the lower alkyl group may or may not be substituted and that the description includes as many unsubstituted lower alkyls as lower alkyls where there is a substitution. By the term "effective amount" of a compound, product or composition as provided herein means a sufficient amount of the compound, product or composition to provide the desired result. As will be indicated below, the exact amount required will vary from one substrate to another, depending on the particular compound, product or composition used, its mode of administration and the like. In this way, it is not always practical to specify an exact "effective amount", especially since a scale of quantities and concentrations will generally be effective. However, an appropriate effective amount may be determined by one skilled in the art using only routine experimentation as a matter of optimization. The term "cyclic" is used to refer to all aliphatic or aromatic hydrocarbons having one or more closed rings, whether saturated or unsaturated. Preferably, the cyclic compounds possess rings of 5 to 7 atoms, preferably of 6 carbon atoms. These rings fall into three classes: alicyclic, aromatic ("arene") and heterocyclic. However, when used with respect to compounds or cyclic portions, the term "unsaturated" refers to a compound or portion of this type that possesses at least one double or triple bond or that otherwise constitutes a compound or portion aromatic In addition, the term "saturated" refers to compounds or portions that do not possess double or triple bonds within the ring, that is, where all available valence bonds of an atom, especially carbon, are attached to other atoms. The term "heterocyclic" refers to a cyclic compound or cyclic portion wherein one or more of the ring carbon atoms has been replaced by a heterogeneous atom, including but not limited to O, N or S. The term "aryl" and "aromatic" is used interchangeably herein and refers to a compound or portion whose molecules have a ring or a multiple ring (poly) structure characteristic of benzene, naphthalene, phenentrene, anthracene, etc. Examples of aryl or aromatics also include but are not limited to phenyl, benzyl, naphthyl, benzylidino, xylyl, styrene, styryl, phenethyl, phenylene, benzentriyl, etc. The term "heteroaryl" and "heteroaromatic" are used interchangeably and refer to an aryl wherein one or more of the carbon atoms of a ring have been substituted with a heterogeneous atom including but not limited to O, N or S. The term "cyclic alcohol" as used herein refers to a cyclic molecule substituted with one or more hydroxyl portions. Examples of these include but are not limited to phenol and cyclohexanol. As used herein, especially in reference to alkyl and alkoxy, the term "lower" refers to a portion having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms. As used herein, the term "suitable" is used to refer to a portion that is compatible with the compounds, products or compositions as provided herein for the stated purpose. Suitably, for the stated purpose it can be determined by one skilled in the art using only routine experimentation. As used herein, "substituted" is used to refer generally to a suitable carbon or heterogeneous atom having a hydrogen or other atom removed and replaced by an additional portion. In one embodiment, substitutions based on halogen, hydroxy and nitrogen of hydrocarbon hydrogens are contemplated within the scope of the present invention for the claimed structures. In addition, "substituted" is intended to refer to substitutions that do not change the basic and novel utility of the compounds, products or fundamental compositions of the present invention. "Unsubstituted" refers to a structure in which the reference atom does not have additional portions fixed thereto or substituted. As used herein, "branched" is used to refer generally to a portion having a carbon chain base structure, for example, alkyl or alkoxy, wherein the base structure may contain one or more subordinate carbon chain branches. For example, isobutyl, t-butyl, isopropyl, CH2CH2C (CH3) (H) CH2CH3,
CH2C (CH2CH3) (H) CH2CH3, CH2CH2C (CH3) CH3 and CH2CH2C (CH3), would be considered branched portions. Furthermore, it is intended that the "branched" variations of the portions described herein refer to variations that do not change the basic and novel utility of the fundamental compounds, products or compositions of the present invention. "Unbranched" refers to a structure where the carbon chain has no branch in it, that is, where the carbon chain extends in a straight line. As used herein, the term "acyl" refers to portions derived from organic acid of the formula RCO wherein R is an organic molecule. The free valence in C is used to join other groups or atoms. As used herein, the term "acyloxy" refers to portions derived from organic acid of the formula RCOX wherein R is an organic molecule and X, instead of being hydroxyl, represents oxygen bound to another group or atom. As used herein, the term "perfluoro" or "perfluoro analogue" refers to a hydrocarbon wherein the hydrogen atoms attached to the carbons have been replaced by atoms of F.
Preferably, but not necessarily, in perfluoro analogues, most if not all of the H atoms are replaced by F atoms. A "fluoro" analog is contemplated to mean a hydrocarbon wherein at least one hydrogen atom is attached to a carbon is replaced by an atom of F. As used herein, "substrate" refers to any article, product or surface that can be treated with the compounds of the invention, preferably as listed below under the heading "Uses", as described in the examples herein and specified in the appended claims appended thereto. Suitable substrates are generally characterized as having either a negatively charged surface of oxygen atoms or any surface capable of binding or adhering to the compounds, products or compositions of the present invention in an electrostatic, ionic or covalent manner. preferably, adhesion or binding occurs in the silicon atoms of the organosilane portion of the compounds, products or compositions of the present invention, but such bonding is not a requirement. "Substrate" also refers to materials that are treated by the incorporation of compounds and / or compositions of the present invention. The incorporation in this case includes the combination and mixing process and the incorporation upon becoming part of the material, ie, polymer and cement base structure. As used herein, the term "adheres" means the ionic, covalent, electrostatic or other chemical fixation of a compound, product or composition to a substrate. As used herein, the term "antimicrobial enhancer" refers to the use of the compounds, products or compositions of the present invention, preferably those wherein the organosilane has antimicrobial activity, together with other ingredients, surfactants, fillers, wetting agents , pigments, dyes, antimigrants, etc., to create a composition or solution capable of satisfying its original purpose, based on the other ingredients, and also to provide antimicrobial protection during the particular application. The term "increases" refers to the addition of antimicrobial activity to said compositions or solutions where such activity did not previously exist, or to the increase in antimicrobial activity where the starting compositions or solutions already possessed antimicrobial activity. As used herein, "hydrolyzable" refers to either the portion that is capable of undergoing hydrolysis or that is subject to hydrolysis (i.e., separation of the molecule or portion into two or more new molecules or portions) into a aqueous medium or other suitable medium. By contrast, "non-hydrolysable" refers to portions that are not subject to hydrolysis or are not capable of undergoing hydrolysis in an aqueous medium or other suitable medium. As used here, "cationic" is used to refer to any compound, ion, or portion that possesses a positive charge. In addition, "anionic" is used to refer to any compound, ion or portion that has a negative charge. In addition, "monovalent" and "divalent" are used to refer to portions that have valences of 1 and 2, respectively. As used herein, the term "salt" means to apply in its generally defined sense as "compound formed by replacing all or part of the hydrogen ions of an acid with one or more cations of a base". See, for example, American Heritage Dictionary, Definition of "salt" (1981). Therefore, suitable salts of the present invention can be formed by replacing a hydrogen ion of a portion with a cation, such as K +, Na +, Ca2 +, Mg2 +, etc. In addition, other suitable methods for generating salts are specified throughout this description and are within the scope of the present definition. For the purposes of the present invention, the specific identity of the cation used to form the salt is of less importance than the chemical structure of the anion from which the salt is formed. As used herein, "food article" refers to perishable or non-perishable foods such as meats, fruits or vegetables, and also refers to other foods such as grains and dairy products. In preferable embodiments, the food items referred to herein are those that are perishable or are susceptible to rot upon exposure to microbes or other pathogens.
In addition, "consumable product" means food items, fluids to drink, medicines to be ingested or any other product introduced internally introduced through any means to a human or animal. As used herein, the term "antimicrobial" is used in its general sense to refer to the property of the described compound, product, composition or article to prevent or reduce the growth, spread, formation or other vital function of organisms such as bacteria. , viruses, protozoa, molds or other organisms that are possible causes of putrefaction or infection. As used herein, the term "medical article" is used to refer to any suitable substrate that is or may be in contact with clinical patients (human or animal), medical or medical personnel, body fluids or any other source of contamination or infection generally associated with hospitals, clinics, doctors' offices, etc.
As used herein, the term "stabilizer" is used to refer to carbonates. It has been found that said compounds stabilize the organosilanes of the invention avoiding self-condensation or other inactivation of the resulting compounds or products and simplifying transport, dilution with water and stabilization in water. With these definitions in mind, the present invention provides the product formed by mixing an organosilane of the formula RnSiX4_n wherein n is an integer from 0 to 3, preferably 0 to 2; each R is independently a non-hydrolyzable organic group and each X is independently a hydrolyzable group; with an organic carbonate. Most preferably, in the above product, n is an integer from 0 to 2, preferably 1; each R is independently alkyl, preferably from 1 to 22 carbon atoms, branched or unbranched, substituted or unsubstituted, most preferably from 1 to 6 carbon atoms or from 10 to 20 carbon atoms, most preferably from 1 to 4 carbon atoms. carbon or from 14 to 18 carbon atoms; alkyl alcohol of similar carbon lengths, branching and substitution, or aromatic such as benzyl, phenyl, etc .; each X is independently hydroxyl, alkoxy, halogen (such as, but not limited to Cl, Br, I or F), acetyl, acetoxy, acyl, acyloxy, a hydroxylated solid or liquid polymer portion, polyglycolic or polyalkyl ether; and carbonate stabilizers according to the invention are described in the formula la and Ib:
wherein each R is independently, alkyl of 1 to 24 carbon atoms, ethylene glycol, propylene glycol, butyl glycol, pentyl glycol, hexyl glycol, alkyl glycol with 2 to 24 carbon atoms, aromatic molecule, heteroaromatic, saturated and unsaturated cyclic aliphatic, each with sizes of ring of 3 to 8 carbon atoms and furthermore in heterocycles N, O, S instead of carbon atoms in any number and combination, alkyl alcohol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol and block and copolymers of ethylene glycol , propylene glycol, butyl glycol, pentyl glycol, hexyl glycol, alkyl glycol with 2 to 24 carbon atoms, alkyltriol with 3 to 24 carbon atoms, alkyltetrol with 4 to 24 carbon atoms and alkylpentol with 5 to 24 carbon atoms and alkylhexol with 6 to 24 carbon atoms, aromatic alcohol, heteroaromatic alcohol, saturated and unsaturated aliphatic cyclic alcohol, each with ring sizes of 3 to 8 carbon atoms and furthermore in heterocycles N, O, S instead of carbon atoms in any number and combination, with 1 to 6 hydroxyl groups in the cyclic alcohol and substitution in the ring for (R3)? x being an integer from 0 to 3, wherein R3 is independently an alkyl substituted with (OH) v of 1 to 24 carbon atoms where y is an integer from 0 to 6. The molecular weight of the carbonate is up to about 10,000 grams / mol of average molecular weight. In a further embodiment of the invention, the invention provides the above described product, wherein the organosilane is of the formula II. lll, IV or V: (R1) 3S¡R2N + (R3) (R4) (R5) Y- (M) (R1) 3SiR2N (R3) (R4) (III)
(R-O3SÍR2R35 (IV) (R1) 3Si (R36) (R37) (V) wherein each R- | is independently halogen or R6Ü, wherein RQ is H, alkyl of 1 to about 24 carbon atoms, acetyl , acetoxy, acyl, acyloxy, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, the monoether alkyl of 1 to 24 carbon atoms of the following: propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and ethylene copolymers and propylene glycol, or the monoester of a carbonic acid of 1 to 24 carbon atoms and at least one of the following: propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, sorbitan esters and their ethers; phenolics substituted with an alkyl of about 1 to about 24 carbon atoms, such as octylphenol and nonylphenol and their ethers; R35 is Rß, H, halogen (such as Cl, Br, F or I),
NH2 (CH2) 2NHR2, NH2R2. C3H5O2R2, C4H5O2R2, C4H5? 2R2 > NaO (CH3O) P (0) R2 or CICH2C6H4R2; R 35 and R 37 are independently R 35, halogen, H, alkyl, preferably 1 to 4 carbon atoms, most preferably 1 to 2 carbon atoms, isobutyl, phenyl or n-octyl; R2 is RQ, benzyl, vinyl or alkyl; R3 and R4 are independently R35, alkyl alcohol, alkoxy, alkyl of 1 to 24 carbon atoms, preferably 1 to about 10 carbon atoms, most preferably alkyl of 1 to 4 carbon atoms, or most preferably 1 to 2 carbon atoms of carbon; R3 and R4 together can form a morpholine or a five to seven membered saturated or unsaturated, heterocyclic or cyclic ring of the formula VI: -R3- (R7) k -R4- (VI) wherein k is an integer from 0 to 2, preferably 0 to 1, most preferably 1, R7, wherein the ring is saturated, is CH2, O, S, NH, NH2 +, NCH2CH2NH2, NCH2CH2NH3 +, NCH2CH_2N (R8) (R9), NCH2CH2N + (R8) (R9) (R? O) > N (alkyl), N (aryl), N (benzyl), wherein each R3, Rg and Rio is independently benzyl, R37, polyglycol, preferably 1 to 4 carbon atoms, alkyl alcohol, preferably 1 to 4 carbon atoms. carbon, alkoxy, preferably of 1 to 4 carbon atoms, or alkyl, of 1 to 24 carbon atoms, preferably of 1 to about 10 carbon atoms, and the "alkyl" specified above is of 1 to 3 carbon atoms, the "aryl" is most preferably phenyl or benzyl, and R7, wherein the ring is unsaturated, is CH, N, N + H, N + (alkyl), N + (aryl), N + (benzyl), N-CH2-N , N + H-CH 2 -N, N + (alkyl) -CH 2 -N, or N + (benzyl) -CH _ + - N, wherein the alkyl, aryl or benzyl is as described above; wherein the ring is unsubstituted or substituted with alkyl of 1 to 24 carbon atoms, most preferably 1 to 10 carbon atoms, most preferably 1 to 3 carbon atoms, ester, aldehyde, carboxylate (preferably acetoxy, acetyl, acyl, acyloxy or perfluorocarboxylate) amide, thionamide, nitro, amine or halide, most preferably Cl, Br or I. Alternatively, the procyclic ring by formula VI represents R3 or R4, independently. The nitrogen in formula II or III which is part of the ring structure VI is replaced by CH or CH2 or saturated with hydrogen or alkyl substitution of 1 to about 24 carbons by removal of a positive charge. This ring is attached to the nitrogen in structure II or III, removing any hydrogen from the structure and placing a nitrogen bond of II or III to the atom that does not have hydrogen.
R5 is alkyl alcohol, preferably 1 to 6 carbon atoms, most preferably 1 to 4 carbon atoms, R35, CH2C6H5, polyglycol, such as polyethylene glycol or polypropylene glycol, alkyl of 1 to 24 carbon atoms, preferably 1 to 10. carbon atoms, most preferably from 1 to 6 carbon atoms, alkoxy, from 1 to 24 carbon atoms, most preferably from 1 to 10 carbon atoms, most preferably still from 1 to 6 carbon atoms, perfluoroalkyl, from 1 to 24 carbon atoms, most preferably from 1 to 10 carbon atoms, most preferably still from 1 to 6 carbon atoms, perfluoroalkylsulfonate, from 1 to 24 carbon atoms, most preferably from 1 to 10 carbon atoms, most preferably still from 1 to 6 carbon atoms, perfluoroalkylcarboxylate, or is a ring of five to seven members of formula V as described above; and Y "is an anionic portion suitable for forming salts of the compound of formula II, III, IV and V. This invention provides a water-stable composition, containing water and an organosilane of interest, mixed with carbonate. a composition for treating a substrate, comprising a vehicle and an effective amount of an organosilane of interest and a carbonate as described herein.The vehicle may be water, or in other embodiments, the vehicle is other than water. The present invention also provides a product resulting from the mixture of an organosilane of the formula II, III, IV or V: (R1) 3 SiR2N + (R3) (R4) (R5) Y "(II) (R1) 3 SiR2N (R3) ) (R4) (III)
(R1) 3SiR2R35 (IV) (R1) 3Si (R36) (R37) (V) as described above in substantial manner with reference to the numbers of formula II, III, IV and V, with ether stabilizers according to invention as described above. In addition, the present invention also provides a method for treating a substrate comprising contacting the substrate with a sufficient amount of the composition as described above for a period sufficient for the treatment of the substrate. Further, in an alternative embodiment the present invention provides a method for treating a substrate, comprising contacting the substrate with a sufficient amount of the compound as described above for a period sufficient for the treatment of the substrate. In addition, the present invention provides a treated substrate that has adhered thereto the product obtained by contacting the organosilane and the ether as described above. Alternatively, the present invention provides a treated substrate having adhered thereto a compound obtained by contacting the organosilane and the carbonate as described above. In another embodiment, the present invention provides a method for dyeing and treating a substrate, which consists in contacting the substrate with an aqueous (ie, substantially water-soluble) composition comprising a water soluble dye suitable for dyeing a substrate and the product formed by mixing an organosilane of interest with an organic carbonate. In still another embodiment, the present invention provides a method for antimicrobially treating a substrate selected from the group consisting of a concrete tube, food article, fluid container, glove, bath curtain, bathroom door, latex medical article, toothbrush, comb, hairbrush, denture or other orthodontic adhesive, a spa or pool filter, an air filter, an HVAC air system, a cabin air system, a marble item, a statue, an exposed work of art, a plastic cover made of PE, PP or polyester, a fiberglass article coated with silicone or TEFLONR, a Dryvitt finish, a stucco finish, combined cotton, a bio-film, a bio-adhesive, a single-layer roof, a para-roof and a fiberglass reinforcement product that consists in contacting the substrate with an effective amount of the product formed by mixing an antimicrobial organosilane iano of interest with an organic carbonate. A further embodiment of the present invention provides a method for antimicrobially increasing a rubbing alcohol product, a flower preserver, or a waterproof solution, which consists of mixing an effective amount of the product formed when mixing an organosilane with the product. antimicrobial of interest with an organic carbonate. The present invention provides compounds, products and compositions of organosilane stable to water and solubilized in water, methods for its use and articles prepared using the compounds, products and compositions. In particular, the present invention is useful for stabilizing a wide variety of organosilanes of the general formula Rn iX4_n, wherein n is an integer from 0 to 3, preferably 0 to 2; R is a non-hydrolysable organic group, such as but not limited to alkyl, aromatic, organofunctional or a combination thereof; and X is halogen, such as but not limited to Cl, Br or I, or X is hydroxyl, alkoxy such as methoxy or ethoxy, acetoxy or acyl or unsubstituted or substituted acyloxy. For said organosilanes, X is subject to reacting with several hydroxyl-containing molecules. In a further embodiment, the present invention employs a carbonate as a solvent. The silane and the carbonate mixture are stable. Carbonate-silane mixtures are often less flammable than methanol mixtures and are easier to dissolve in water than many silanes in methanol. Alternatively, where the stabilizers are not sufficiently soluble in water, additional stability is achieved by mixing the organosilane with the stabilizer in a non-aqueous solvent. Said alternative preparation, the remaining solvent (for example, methanol) is released through distillation, freeze drying, evaporation or other methods known in the art to remove volatile organic solvents. For ethers within this invention which by themselves are not very soluble in water, a stabilizing effect of organosilane in water can still be achieved by mixing the organosilane, for example, with a carbonate in water, followed by filtration. The solutions are stable for prolonged periods, from a few days to a few months. It will also be recognized that although aqueous silane silane solutions of up to 45% silane can be stabilized by carbonates described herein, silane concentrations can be in the range of 0.001 -10% silane wherein the stabilizing effects of the stabilizers described herein are less challenged by the higher silane compositions in sourcing solutions. Acidic pHs appear to be preferred, but are not required, for stability of the solutions of the present invention. The solutions of the present invention, in certain preferred embodiments, are useful for the application of various organosilane coupling agents to surfaces in industrial and domestic uses without the use of toxic and / or flammable organic solvents. One skilled in the art will recognize that the above preparation steps are merely a guide and said expert, even without experimentation, can prepare the composition by varying the parameters to contact or mix the organosilane and the polyol and the order of introduction of the reagents and starting materials without deviating from the basic and novel features of the present invention.
Silanes The present invention is useful for stabilizing organosilanes of the general formula RnSiX4_n, wherein n is an integer from 0 to 3, preferably 0 to 2; R is a non-hydrolysable organic group (alkyl, aromatic, organofunctional or a combination thereof); and X is hydroxyl, alkoxy, preferably methoxy or ethoxy, halogen, preferably Cl, Br or I, acetoxy, acyl or acyl or substituted acyloxy, or a hydrolysable polymer or a portion subject to hydrolysis and / or environmental damage. The organosilanes used in the practice of the present invention do not need to be water soluble and often are not. By varying the stabilizer and the method of preparation, the organosilanes selected for use in the present invention are solubilized in water by the stabilizer. Many organosilanes known in the art suitable for the stabilization processes of the present invention to produce water stabilized compounds, products and compositions. U.S. Patents 5,411, 585; 5,064,613; 5,145,592, and the publication entitled "A Guide to DC Silane Coupling Agent" (Dow Corning, 1990) describe many suitable organosilanes. The contents of these references are incorporated herein by reference for the teachings of suitable organosilanes. These organosilanes are suitable for the formation of the water stabilized organosilane compounds, products and compositions of the present invention. In addition, the description of the patent of É.U.A. No. 4,390,712 is incorporated herein by reference for the teaching of siloxane synthesis in an aqueous medium. For the present description, those skilled in the art will appreciate that the aqueous siloxane synthesis methods of the 4,390,712 patent are modified to take advantage of performing the siloxane synthesis in the presence of the carbonate stabilizer as defined herein, thereby forming a siloxane composition - Water stabilized while still taking advantage of the accelerated synthesis of siloxane formation in aqueous medium which is seen in the patent 4,390,712. Accordingly, a further embodiment of this invention is a method for making an organosilane of the formula RnSiX4_n wherein n is an integer from 0 to 3, preferably 0 to 2; each R is independently a non-hydrolysable organic group; and X is independently a hydrolysable group; of starting materials in an aqueous solution in the presence of an effective amount of carbonate sufficient to stabilize the organosilane that is formed from the reactants. In the present application, the finding is disclosed that the compounds having at least one carbonate group stabilize the aqueous organosilane solutions. The carbonate archetype example of the present invention is propylene carbonate with an organic carbonate. Preferred for use in the compounds, products and compositions and methods of the present invention include silanes silanes of the following formula: (R1) 3SiR2N + (R3) (R4) (R5) or Y- (R1) 3SiR2N + C5H5Y- where each R ^ is independently halogen [Cl, Br, I, F] or RQO, where R? is H, alkyl of 1 to about 6 carbon atoms, unsubstituted or substituted, preferably 1 to about 2 carbon atoms and most preferably 1 carbon atom, or acetyl or other acyl, including acyl and substituted acyloxy, or RQO is it can be derived from any hydroxylated polymer, hydroxylated liquid or hydroxylated solid independently of the solubility in water; or R? O can be derived from a polyglycol such as, but not limited to polyethylene glycols or polypropylene glycols, such as poly (propylene glycol) triol propoxylate (glycerol); R2 is unsubstituted or substituted benzyl or an unsubstituted or substituted alkyl of 1 to about 3 carbon atoms, preferably alkyl of 1 to
3 carbon atoms; R3 and R4 are independently lower alkoxy of 1 to
4 carbon atoms, preferably 2 carbon atoms, such as CH 2 CH 2 OH, CH 2 CH (OH) CH 3, alkyl of 1 to about 22 carbon atoms, preferably 1 to about 10 carbon atoms and most preferably 1 to 2 carbon atoms carbon or R3 and R4 together may form a morpholine or other unsaturated or saturated cyclic or heterocyclic ring of five to seven members of the formula: -R3- (R7) k -R4- where k is an integer from 0 to 2 and R7 where the ring is saturated, is
CH2, O, S, NH, NH2 +, NCH2CH2NH2, NCH2CH2NH3 +
NCH2CH2N (R8) (Rg), NCH2CH2N + (R8) (R9? R-? O), N (alkyl), N (aryl),
N (benzyl) and R7, wherein the ring is saturated, is N, N + H, N + (alkyl), N + (aryl), N + (benzyl), N-CH2-N, N + H-CH2-N, N + (alkyl) -CH2-N, N + (aryl) -CH2-N, or N + (benzyl) -CH2-N wherein Rs, Rg and R 0 are independently benzyl, polyglycol, lower alkyl alcohol of 1 to 4 carbon atoms carbon, lower alkoxy of 1 to 4 carbon atoms or alkyl of 1 to about 22 carbon atoms, preferably 1 to about 10 carbon atoms; R5 is CH2C6H5, CH2CH2OH, CH2CH (OH) CH3, a polyglycol such as polyethylene glycol: - (CH2CH2?) AH, polypropylene glycol: - (CH2CH (CH3) O) aH, or alkylated polyoxyethylene: (CH2CH2?) AB wherein B is alkyl of 1 to 22 carbon atoms, unsubstituted or substituted, and wherein each a is independently an integer from 1 to 12, most preferably from about 1 to about 5, or R5 is alkyl or perfluoroalkyl of from about 1 to about 22 carbon atoms, preferably from about 12 to about 20 carbon atoms and most preferably still from 14 to about 18 carbon atoms; and Y is halogen (such as Cl, Br, I), acetate, sulfate, tosylate or carboxylate, such as acetate, polycarboxylate salts, alcoholates, functionalized carboxylate, such as trifluoroacetate and perfluoroalkylcarboxylates, or other alkyl and arylsulfonate salts, including trifluoromethylsulfonate and anionic metal oxides, perfluoroalkylsulfonate salts, phosphate and phosphonate salts, borate and boronate salts, benzoates or any other suitable anionic portion and the ring provided by the formula V represents R3 or R4 independently, with the ring nitrogen Formula I or II replaced by CH or CH2. This ring is attached to the nitrogen in structure I or II, removing any of the hydrogen from the structure and placing a nitrogen bond of I or II to an atom that does not have nitrogen. Preferred organosilanes include, but are not limited to: 3- (trimethoxysilyl) propyldimethyloctadecylammonium chloride, 3- (trimethoxysilyl) propimetyldi (decyl) ammonium chloride, 3-chloropropyltrimethylsilane, octadecyltrimethoxysilane, perfluorooctyltriethoxysilane, (CH30) 3Si (CH2) 3N + ( CH3) 2C18H37Cr-, (CH30) 3Si (CH2) 3N + (CH3) 2C18H37Br, (CH30) 3Si (CH2) 3N + (C10H21) CH3C | -, (CH3O) 3Si (CH2) 3N + (C10H2l) CH3Br, (CH30) 3S (CH2) 3N + (CH3) 3Cl-, (CH3O) 3Si (CH2) 3N + (CH3) 2C8H17C | -, (CH3O) 3Si (CH2) 3N + (CH3) 2C10H21 CI ", (CH3?) 3Si (CH2 ) 3N + (CH3) 2C12H25Cl-, (CH3?) 3Si (CH2) 3N + (CH3) 2C14H29C | -, (CH3?) 3Si (CH2) 3N + (CH3) 2C16H33C | -, (CH30) 3Si (CH2) 3N + ( CH3) 2C2? H41 CI ", (CH30) 3Si (CH2) 3N + (C4H9) 3C | -, (CH30) 3Si (CH2) 3N + (C2H5) 3C | -, (CH3CH20) 3Si (CH2) 3N + (CH3) 2C18H27C | -, (CH30) 3Si (CH2) 3NHC (0) (CF2) 6CF3, (CH30) 3Si (CH2) 3NHC (0) (CF2) 8CF3, (CH30) 3Si (CH2) 3NHC (0) (CF2) ? oCF3, (CH30) 3YES (CH2) 3NHC (0) (CF2) 12CF3, (CH3O) 3Si (CH2) 3NHC (O) (CF2) i4CF3, (CH30) 3YES (CH2) 3NHC (0) (CF2) 16CF3 , (CH30) 3S (CH2) 3NHS02 (CF2) 7CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH 2) 3NHC (0) (CH2) 6CH3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 8CH3, (CH30) 3YES (CH2) 3N + (CH3) 2 (CH2) ) 3NHC (0) (CH2) 0CH3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 12CH3, (CH30) 3YES (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 14CH3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O) (CH2) l6CH3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0XCF2) 6CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 8CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0 ) (CF2) 10CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 12CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 14CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 16CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS? 2 (CF2 ) 7CF3j (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS? 2 (CF2) 9CF3, (CH30) 3YES (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 11 CF3, (CH30) ) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS? 2 (CF2) l3CF3l (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 15CF3, (CH30) 3YES (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 16CF3, aminoethylaminopropyltrimethoxysilane: NH2 (CH2) 2NH (CH2) 3Si (OCH3) 3,
3-aminopropyltrimethoxysilane: NH 2 (CH 2) 3 Si (OCH 3) 3, 3-aminopropyltriethoxysilane: NH 2 (CH 2) 3 Si (OCH 2 CH 3) 3, 3-chloropropyltrimethoxysilane: CI (CH 2) 3 Si (OCH 3) 3, 3-chloropropyltriethoxysilane: CI (CH2) 3Si (OCH2CH3) 3, 3-chloropropyltrichlorosilane: CI (CH2) 3SiCl3, 3-glycidoxypropyltrimethoxysilane: C3H5 2 (CH2) 3Si (OCH3) 3, 3-glycidoxypropyltriethoxysilane:? C3H5 2 (CH2 ) 3 Si (OCH2CH3) 3, 3-methacryloxypropyltrimethoxysilane: C4H5? 2 (CH2) 3Si (OCH3) 3, 3-methacryloxypropyltriethoxysilane: C4H5? 2 (CH2) 3Si (OCH2CH3) 3, Methyldichlorosilane: CH3SIHCl2, melamine modified by silane: Dow Corning Q1-6106, (trihydroxysilyl) propilmetilfosfonato sodium: NaO (CH3?) P (0) - (CH2) 3Si (OH) 3, trichlorosilane, SÍHCI3, n-2-vinilbenzilamino-ethyl-3-aminopropyltrimethoxysilane HCL: Dow Corning Z - 6032, vinyltriacetoxysilane: H2C = CHSi (OCOCH3) 3, vinyltrimethoxysilane: H2C = CHSi (OCOCH3) 3, vinyltriethoxysilane: H2C = CHSi (OCH2CH3) 3, vinyltrichlorosilane: H2C = CHSiCl3, dimethyldichlorosilane: (CH3) 2SiCl2, dimethyldimethoxysilane: (CH3 ) 2 Si (OCH3) 2, diphenyldichlorosilane: (C ^ Hs ^ SiC, ethyltrichlorosilane: (C2H5) SiCl 3, ethyltrimethoxysilane: (C2H5) Si (OCH3) 3, ethyltriethoxysilane: (C2H5) Si (OCH2CH3) 3, isobutiltrimeto xisilano, n-octyltriethoxysilane, methylphenyldichlorosilane: CH3 (C6H5) SiCl2, methyltrichlorosilane: CH3SÍCI3, methyltrimethoxysilane: CH3Si (OCH3) 3, phenyltrichlorosilane: C6H5SÍCI3, phenyltrimethoxysilane: C6H5Si (OCH3) 3, n-propyltrichlorosilane: C3H7SÍCI3, n-propyltrimethoxysilane: C3H7Si ( OCH3) 3, silicon tetrachloride: SiCl4, CICH2C6H4CH2CH2SiCl3n, CICH2C6H4CH2CH2Si (OCH3) 3, CICH2C6H4CH2CH2S¡ (OCH2CH3) 3, decyltrichlorosilane, dichloromethyl (4-methylphenethyl) silane, diethoxymethylsilane, [3- (diethylamino) propyl] tristathoxy Lano, 3- (dimetoximetilsilil) -1-propanethiol, dimetoximetilvinilsilano methacrylate, 3- [tris (trimetilililoxi) silyl] propyl trichloro [4- (chloromethyl) phenyl] silane, met¡lbis (trimethylsilyloxy) vinylsilane, methyltripropoxysilane, and triclorociclopentilsilano . In a particular embodiment of this invention, namely the use of organosilane as a UV protector, for example, in a tanning lotion, para-aminobenzoic acid, cinnamic acid, benzoic acid and benzophenone are active ingredients. These compounds and their alkyl derivatives attached to a silane are part of this invention. Some examples are:
(CH30) 3Si (CH2) 3NHC6H4COOH (CH3O) 3Si (CH2) 3NHC6H4COOCH3 (CH3O) 3Si (CH2) 3NHC6H4COOC2H5 (CH3O) 3Si (CH2) 3NHC6H4COOC3H7 (CH30) 3Si (CH2) 3NHC6H4COOC4H9 (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H5 ( CH3O) 3Si (CH2) 3NHC6H4COOCH2C6H4NH2 (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4N (CH3) 2 (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4N (CH2CH3) 2 (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH3) 3 Y- (CH3O) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH2CH3) 3 Y- (CH30) 3Si (CH2) 3NCH3C6H4COOH (CH30) 3Si (CH2) 3NCH3C6H4COOCH3 (CH3?) 3Si (CH2) 3NCH3C6H4COOC-2H5 (CH30) 3Si (CH2) 3NCH3C6H4COOC3H7 (CH30) Si (CH2) 3NCH3C6H4COOC4H9 (CH30) 3Si (CH2) 3NCH3C6H4COOCH2C6H5 (CH3O) 3Si (CH2) 3NCH3C6H4COOCH2C6H4NH2 (CH3?) 3S¡ (CH2) 3NCH3C6H4COOCH2C6H4N (CH3) 2 (CH30) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N (CH2CH3) 2 (CH3 ?) 3 Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH3) 3 Y- (CH30) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH2CH3) 3 Y ~
(CH30) 3Si (CH2) 3N + (CH3) 2C6H4COOH Y- (CH3O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH3 Y- (CH3?) 3Si (CH2) 3N + (CH3) 2C6H4COOC2H5 Y- (CH3?) 3Si ( CH2) 3N + (CH3) 2C6H4COOC3H7 Y- (CH30) 3Si (CH2) 3N + (CH3) 2C6H4COOC4H9 Y "(CH3?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H5 Y- (CH3?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4NH2 Y- (CH3?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH3) 2 Y- (CH3?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y- (CH30) 3Si (CH2 ) 3N + (CH3) 2C6H4C00CH2C6H4N + (CH3) 3 YY- (CH30) 3Si (CH2) 3N + (CH3) 2C6H4C00CH2C6H4N + (CH2CH3) 3 YY- (CH3?) 3Si (CH2) 3NC2H5C6H4COOH (CH3?) 3Si (CH2) 3NC2H5C6H4COOCH3 ( CH3?) 3Si (CH2) 3NC2H5C6H4COOC4H9 (CH3?) 3Si (CH2) 3NC2H5C6H4COOC3H7 (CH3?) 3Si (CH2) 3NC2H5C6H4COOC4H9 (CH30) 3S¡ (CH2) 3NC2H5C6H4COOCH2C6H5 (CH30) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4NH2 (CH3?) 3Si (CH2 ) 3NC2H5C6H4COOCH2C6H4N (CH3) 2 (CH30) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N (CH2CH3) 2 (CH3?) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH3) 3 Y- (CH3?) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH2CH3) 3 Y "(CH30) ) 3S (CH2) 3N + (C2H5) 2C6H4COOH Y "(CH3) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH3 Y- (CH3?) 3Si (CH2) 3N + (C2H5 ) 2C6H4COOC2H5 Y- (CH3O) 3Si (CH2) 3N + (C2H5) 2C6H4COOC3H7 Y- (CH3?) 3Si (CH2) 3N + (C2H5) 2C6H4COOC4H9 Y- (CH30) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H5 Y "(CH3? ) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N2 Y- (CH3?) 3Si (CH2) 3N + (C2H5) 2C6H COOCH2C6H4N (CH3) 2 Y- (CH3?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y - (CH30) 3S (CH2) 3N + (C2H5) 2C6H4C00CH2C6H4N + (CH3) 3 YY- (CH3O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N + (CH2CH3) 3 And "Y"
(CH3CH2?) 3Si (CH2) 3NHC6H4COOH (CH3CH2?) 3Si (CH2) 3NHC6H4COOCH3 (CH3CH2?) 3Si (CH2) 3NHC6H4COOC2H5 (CH3CH2O) 3S¡ (CH2) 3NHC6H4COOC3H7 (CH3CH20) 3 Si (CH2) 3NHC6H4COOC4H9 (CH3CH2?) 3Si ( CH2) 3NHC6H4COOCH2C6H5 (CH3CH20) 3 Si (CH2) 3NHC6H4COOCH2C6H4NH2 (CH3CH20) 3 Si (CH2) 3NHC6H4COOCH2C6H4N (CH3) 2 (CH3CH2?) 3Si (CH2) 3NHC6H4COOCH2C6H4N (CH2CH3) 2 (CH3CH2?) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH3) 3 Y - (CH3CH20) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH2CH3) 3 Y- (CH3CH20) 3Si (CH2) 3NCH3C6H4COOH (CH3CH2?) 3Si (CH2) 3NCH3C6H4COOCH3 (CH3CH2?) 3Si (CH2) 3NCH3C6H4COOC2H5 (CH3CH2?) 3Si (CH2) 3NCH3C6H4COOC3H7 (CH3CH2?) 3Si (CH2) 3NCH3C6H4COOC4H9 (CH3CH2O) 3Si (CH2) 3NCH3C6H4COOCH2C6H5 (CH3CH2?) 3Si (CH2) 3NCH3C6H4COOCH2C6H4NH2 (CH3CH20) 3 Si (CH2) 3NCH3C6H4COOCH2C6H4N (CH3) 2 (CH3CH2O) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N (CH2CH3) 2 (CH3CH2?) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH3) 3 Y- (CH3CH2?) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH2CH3) 3 Y- (CH3CH2?) 3Si (CH2) 3N + (CH3) 2C6H4COOH Y "(CH3CH2?) 3S (CH2) 3N + (CH3) 2C6H4COOCH3 Y- (CH3CH2?) 3Si (CH2) 3N + (CH3) 2C6H4COOC2H5 Y- (CH3CH2?) 3Si (CH2) 3N + (CH3) 2C6H 4COOC3H7 Y- (CH3CH20) 3Si (CH2) 3N + (CH3) 2C6H4COOC4H9 Y- (CH3CH2?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H5 Y- (CH3CH2O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4NH2 Y- (CH3CH2?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH3) 2 Y- (CH3CH2?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y- (CH3CH2?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N + (CH3 ) 3 Y? - (CH3CH2?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N + (CH2CH3) 3 Y -? - (CH3CH2O) 3Si (CH2) 3NC2H5C6H4COOH (CH3CH2?) 3Si (CH2) 3NC2H5C6H4COOCH3 (CH3CH2?) 3S (CH2) 3NC2H5C6H4COOC2H5 (CH3CH2?) 3S¡ (CH2) 3NC2H5C6H4COOC3H7 (CH3CH2?) 3S¡ (CH2) 3NC2H5C6H4COOC4H9 (CH3CH2O) 3S¡ (CH2) 3NC2H5C6H4COOCH2C6H5 (CH3CH2?) 3S¡ (CH2) 3NC2H5C6H4COOCH2C6H4NH2 (CH3CH2?) 3S¡ (CH2) 3NC2H5C6H4COOCH2C6H4N (CH3) 2 (CH3CH2?) 3S¡ (CH2) 3NC2H5C6H4COOCH2C6H4N (CH2CH3) 2 (CH3CH2?) 3S¡ (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH3) 3 Y- (CH3CH2?) 3S¡ (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH2CH3 ) 3 Y- (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOH Y- (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH3 Y- (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOC2H5 Y - (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOC3H7 Y- (CH3CH2?) 3S (CH2) 3N + (C2H5) 2C6H4COOC4H9 Y- (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H5 Y- (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4NH2 Y- (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N (CH3) 2 Y- (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y- (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N + (CH3) 3 Y- ? -, and (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N + (CH2CH3) 3 Y -? -.
Stabilizers The carbonate stabilizers according to the invention are described by the formulas la and Ib:
wherein each R is independently alkyl of 1 to 24 carbon atoms ethylene glycol, propylene glycol, butyl glycol, pentyl glycol, hexyl glycol, alkyl glycol with 2 to 24 carbon atoms, aromatic, heteroaromatic, saturated and unsaturated molecule, each with ring sizes of 3 to 8 carbon atoms and furthermore in heterocycles N, O, S instead of carbon atoms in any number and combination, alkyl alcohol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol and block and copolymers of ethylene glycol, propylene glycol, butyl glycol, pentyl glycol, hexyl glycol, alkyl glycol with 2 to 24 carbon atoms, alkyltriol with 3 to 24 carbon atoms, alkyltetrol with 4 to 24 carbon atoms and alkylpentol with 5 to 24 carbon atoms and alkylhexol with 6 to 24 carbon atoms , aromatic alcohol, heteroaromatic alcohol, saturated and unsaturated aliphatic cyclic alcohol, each with ring sizes of 3 to 8 carbons and also in heterocycles N, O, S instead of carbon atoms in any number and combination, with 1 to 6 hydroxyl groups in the cyclic alcohol and substitution in the ring for (R8)? x being an integer from 0 to 3, wherein R3 is independently an alkyl substituted with (OH) v of 1 to 24 carbon atoms where y is an integer from 0 to 6. The molecular weight of the carbonate is up to about 10,000 grams / mol of average molecular weight.
Uses The compounds, products and compositions of the present invention are useful for many purposes. Such purposes include any known use for the organosilanes of the preferred starting material of the general formula described above. In preferred embodiments, the water stabilized organosilane compounds, products and compositions described in the present invention are suitable for applications such as: 1) surface treatment, including fillers and pigments, 2) additives to coatings such as dyes, 3) as additives to organic monomers (such as acrylics) before the formation of the respective polymer, 4) addition to the pre-process polymer in final products, or 5) incorporation into polymer or substrate base structure, such as polyester or concrete. Therefore, in addition to the utility of quaternary organosilane ammonium compounds such as 3- (trimethoxysilyl) propyl-dimethyloctadecylammonium chloride as surface binding antimicrobial agents, many other uses of organofunctional silanes are contemplated, such as the use of the compounds, products and compositions of the invention in coating applications including the treatment of surfaces or particles (pigments or fillers), in sizes, in paints, inks, dyes and adhesives, and as reactive intermediates for silicone resin synthesis. The present invention can be used to prepare, among others, agricultural products, cleaning compositions, antimicrobial sponges, antimicrobial whitening agents, antimicrobial fillers for paints, plastics or concrete, and to treat concrete structures such as stable where the microbial infestation is a problem. In various embodiments, surfaces and substrates treatable with the compounds, products, and compositions of the invention include, but are not limited to, textiles, carpets, carpet backs, upholstery, clothing, sponges, plastics, metals, surgical apparel, masonry, silica, sand, alumina, aluminum, carbohydrate, titanium dioxide, calcium carbonate, wood, glass spheres, containers, mosaics, floors, curtains, marine products, tents, backpacks, roofs, walls, fences, fittings, insulation , wall boards, trash containers, outdoor equipment, water purification systems and soil. In addition, items that can be treated with compounds, products and compositions of the invention, include but are not limited to air filters and materials used for the manufacture thereof, aquarium filters, cushion pads, fiber fill for upholstery, fiberglass ducts, underwear and outer clothing, polyurethane and polyethylene foam, sandbags, tar products, candles, ropes, shoes, socks, towels, disposable cloths, socks, and intimate clothing; cosmetics, lotions, creams, ointments, disinfectant sanitizers, wood preservatives, plastics, adhesives, paints, pulp, paper, cooling water and additives for laundry and food contact surfaces or that are not for food in general. For the substrates described above, mixtures of applications, the treatment generally involves contacting or mixing the article to be treated with a water stabilized organosilane solution of the present invention, comprising the organosilane stabilizing derivative compound in a solution aqueous, for a period sufficient for the permanent linkage of the active organosilane ingredient (or portion thereof) to the article. In alternative embodiments, the organosilane-carbonate mixtures according to the invention can be used directly without dilution with water or alternatively, dilutions with solvents other than water according to the invention can be used. Generally, the treatment begins immediately upon contact, but preferably requires from about 15 seconds to about 48 hours. Many examples and principles are shown for the treatment and incorporation of surface with silane, for example, "Applying A Silane Coupling Agent", page 49, Gelest Catalog, by Gelest, Inc. Tullytown, PA, 1995. In addition, the general principles for application are as follows: to immerse a large object, it is preferable that 1-2 minutes of immersion are left in the solution and then the object is allowed to dry or dry. However, some objects will benefit with very short immersion, mixing and contact times, for example, the fabric may pass through an aqueous bath of the composition at a rate of 36.56 m / min or more. After submerging, the excess solution can be gently cleaned or rinsed. Alternatively, the solution can be sprayed onto the substrate. However, the composition of the invention can be placed in a high intensity solid mixer and can be formed into a powder which is then dried. The dry powder can then be used in a sprinkler, if desired. In addition, the solutions can be cleaned on the surface and applied using sponges or fabrics, etc. In addition, the solutions of the present invention can be added to pigments and fillers and can be stirred therewith several minutes (2-3). In addition, solutions can be added to an emulsion or other existing formulation before use. Also, the solutions can be used in addition to a spray cooler for extruded fibers, together with it or as the same. However, one skilled in the art will recognize that many other uses and modes of application are readily apparent from the stabilized organosilane compounds, products and compositions of the present invention and even without experimentation, methods and application and times of Effective treatment for a substrate, particular article or other application. In addition, the compositions can be used in pad application procedures as is known in textile mills. Moreover, after treating a surface or fabric with the compound, product or compositions of the present invention, the surface of the fabric may optionally be heated or for complete attachment of the compound, product or composition to the substrate or surface. The water-stable organosilane compounds, products and compositions of the present invention, therefore, are advantageous in treating a variety of substrates without the use of toxic organic solvents and provide safe long-term storage of organosilanol compound. activated that can be used without additional preparation. In addition, the stabilization scheme described herein does not interfere with the binding of the organosilane (or at least the center, operative portion thereof) to the substrate. In addition, the present invention provides a generally applicable scheme for solvating some water insoluble organosilanes. It will also be evident those applications where RnSiX4_n organosilanes are prepared, dissolve, store, apply and in some way are used in water. In addition, it will also be evident applications of RnSiX4_n organosilanes in other solvents or mixed in other media (solids, polymer blends, fillers, pigments, powders, dyes or emulsions) where exposure to water occurs but could be harmful due to undesirable self-condensation or inopportune of silanol. In addition, the stabilizing compounds and methods could be used in addition to various stabilization methods for organosilanes known in the art or together with them, such as the use of ionic or non-ionic surfactants and detergents. Moreover, the present compounds, products and compositions can be used in the incorporation of an organosilane antimicrobial agent in most textile products (fabrics and non-wovens) and yarns (synthetic and natural). The procedure provides items that are durable and the procedure itself is effective and does not require additional manufacturing steps or increased manufacturing costs.
In addition, as is known in the art, certain classes of organosilanes have properties that can repel water and other liquids. Accordingly, one embodiment of the present invention is directed to a method of treating a substrate to render it resistant to staining. The incorporation of compounds, products and compositions of the present invention during the dyeing process produces a textile with an integrated antimicrobial activity or other desired property with the characteristic of organosilane. The incorporation procedure 1) does not add any additional steps in the manufacturing process and does not require any modification of equipment; and 2) it is believed that it does not lose its antimicrobial characteristics and its effectiveness during the additional production of the textile products. By incorporating the water-stable compounds, products and compositions of the present invention during the dyeing process, not only would the organosilane antimicrobial agent remain unaffected by the dyeing agent, but the final textile products would also exhibit excellent dyeing properties. . The water-stable organosilane compounds, products and compositions of the present invention are useful for many applications where prior instability and insolubility prevent or at least prevent or restrict the use of some organosilane agents. For example: The treatment of food culture (eg, perishable products such as vegetables, fruits or grains) after removal (harvesting / harvesting) with the compounds, products and compositions of the present invention imparts antimicrobial protection to the outer surface of the food crop. It is believed that such protection occurs without spreading, migrating or leaching the antimicrobial agent from the bound antimicrobial coating of the food product, and providing prolonged, safe and non-toxic antimicrobial protection. The method involves treating fruits and vegetables in the rinse cycle, during or after normal cleaning / water spraying or during or after bleaching. In the processing plant, a complete cleaning of fruits and vegetables is preferred to initially remove microorganisms. As will be recognized by a person skilled in the art, machines are initially used to remove dirt, chemical compounds used in the crop, rot bacteria and other foreign materials. These machines also use high speed water sprays to clean the products. After cleaning, food or other culture materials are prepared for further processing by bleaching (ie, the food is immersed in water at a temperature of 87.7 to 98.8 ° C or exposed to steam). The microorganisms are controlled by the production plant until the fruit or vegetable is removed. But once it is removed, organisms such as yeasts, molds and bacteria begin to multiply, causing the food to release flavor and change color and texture. To keep food from rotting, many methods, such as refrigerators, have been used to reduce microorganisms and slow down spoilage. Unfortunately, such known methods will retain food for a few weeks at a time.
The compounds, products and compositions of the present invention can preserve these products for extended periods. For example, the compositions, products or compounds can be added to an existing water line that feeds the sprinklers for food, where said sprinklers are used. Otherwise, a simple immersion procedure may be used, where immersion requires a few seconds to impart antimicrobial protection. Low concentrations of 0.1 to 1% aqueous solution (0.1 to 1% by volume) of the compositions provide satisfactory results. In addition, it is believed that the currently described method can also control pathogens in poultry meat and other susceptible meat and fish. Treatment of milk / juice bottles, bottle pacifiers, pacifiers and toys with the compounds, products and compositions of the present invention in the factory or the leaching of milk from the surface in question, can provide prolonged and safe / non-toxic antimicrobial protection. The treatment of these items also eliminates odors caused by microbial contamination. An immersion method as described above can be used to treat these articles. To date, parents have used soaps, detergents and surface cleaners to solve the contamination problems of these items. However, these and other similar treatments, for the most part, have been inadequate and require repeated treatment. In addition, it has been found that these treatments are limited in terms of their ability to offer a broad spectrum control of microorganisms. Therefore, the present compounds, products and compositions can be used to treat these articles to prevent microbial growth and contamination by coating an effective amount of the products and compositions of the invention thereon. The articles used can be coated by leaving them in immersion for 1 to 2 minutes (for example, by immersing them), and subsequently the treated surface is allowed to dry at room temperature. The article is then rinsed of any excess antimicrobial agent. Complete cleaning and sterilization is a preferred step for removing microorganisms on the surface of the article before "coating" said articles. In addition, concentrations of 10% or less by weight of the compounds, products and compositions of the invention in water are used for durable protection. The treatment of surgical gloves with the compounds, products and compositions of the present invention before or during the surgical procedure can kill the microorganisms by contacting them. It is believed that the treated gloves do not diffuse or leach the antimicrobial agent from the surface of the glove and provide prolonged antimicrobial activity with safe and non-toxic antimicrobial protection. The surgical gloves are preferably treated by immersing them in the solution of Example 1, diluted at 1% w / v for at least 30 seconds. The method will allow doctors to use and, if necessary, reuse the same gloves (even without having to remove them) without fear of contamination. The treatment of polymers and other materials such as concrete by incorporation into the bulk material protects against deterioration, odor accumulation and potentially harmful contamination of the surface. The incorporation of a protection against the sun in polymers and / or application of protection against the sun to the surface prolongs the life of the product and reduces the damage to the products and to the skin. In addition, one skilled in the art will be able to implement other end uses based on the description of the compounds, products and compositions of the present invention. Not all uses require aqueous solutions and some require non-aqueous environments, both applications are part of the invention. In addition, the antimicrobial properties of the silane compounds according to the invention is only one of the many possible properties. The silane mixtures according to the invention often provide additional benefits. For example, the following uses, applications and substrates are contemplated: 1. Concrete, concrete water conduits, water and drainage pipes treated with the compounds, products and compositions of the present invention. Agents to kill microorganisms on contact and provide prolonged antimicrobial protection to prevent deterioration of the concrete and its coating. 2. Toothbrushes, combs, hair brushes, dentures and adherents for dentures. 3. Filters for spa and pool meet the strict requirements that can not be met by other antimicrobial agent and protection for air filtration such as air conditioning filters, HVAC applications and cabin air. 4. Marble tiles (building facades, tombs, floors) treated with the compounds, products and compositions of the present invention. 5. Alcohol to rub. 6. Statues and works of art exposed. 7. Plastic covers made of high density polyester fabric, HDP for discharge sites, water tanks and generally for soil protection. 8. Liquid additive (as a preservative for flower water for pot plants and cut flowers). 9. Fiberglass coated with silicone and Teflon with antimicrobial protection including wall cover with acrylic backing. 10. Dryvitt finish and stucco. 11. Raincoats treated with the compounds, products and compositions of the present invention. 12. A method of treating mixed cotton before or after the picking machines form cotton into rolls or packages.
13. Food packaging and containers. 14. Bio-films and adhesives (silicon wafers and wafers). 15. Single-layer roofs and roof tiles. 16. Fiberglass reinforcement product. Preferred embodiments of the above-described water stabilized antimicrobial compounds, products and compositions and methods for their production are set forth in the following examples. Other features of the invention will be apparent from the following examples, which are for illustrative purposes only and are not intended to limit the present invention. The silane in the following examples is Dow Corning 5772 or a silane of similar composition as Dow Corning 5772. Both are collectively known as silane concentrate. A solution or mixture is considered stable if an aqueous solution can be produced and remain without precipitating the silane for a longer time than would be expected for the unstabilized silane. If the silane itself is insoluble in water, the formation of an aqueous solution is a benefit that is within the scope of the invention.
EXAMPLE 1
Water dilutions of a mixture containing 20,049 g of silane concentrate and 20,788 g of ethylene carbonate have been stable at 25.9 wt% of the mixture in water. At 41.4% by weight, the mixture diluted in water appeared unstable. The following table gives a list of examples of mixtures and their stability. The amounts are in percent by weight of the total mixture. The concentrated solutions were prepared and then diluted with water according to them. A) 24,694 g of silane concentrate, 11,596 g of glycol ether DB, 13,593 g of propylene carbonate. B) 25,028 g of silane concentrate, 5,895 g of DB glycol ether, 19,379 g of propylene carbonate.
EXAMPLE 2
The following table gives a list of examples of mixtures and their stability. The amounts are in percent by weight of the total mixture. A 50% by weight solution of silane concent and 50% by weight of propylene carbonate was prepared and then diluted with water according to the table.
EXAMPLE 3
Into a flask was heated and 54.109 g of dimethyloctadecylamine and 53.871 g of 3-chloropropyltrimethoxysilane and 14.960 g of propylene carbonate were stirred. The temperature was maintained at 130 to 135 ° C, when the mixture began to darken, the temperature was reduced to 125 ° C. After 21 hours, the titration of the mixture revealed an amine content of 1.3% and an ammonium content of 72.0%. The product was a soft, light brown solid when it was at room temperature. The reaction product of the previous example was dissolved in water to prepare stable mixtures of silane and water.
EXAMPLE 4
Sample 2 of the example, after 35 days, previous was diluted with 4 parts of water and applied to white textile fabric. After drying, the cloth was washed by hand with tap water 20 times. The sample was allowed to dry again and then tested in accordance with test method 0923 of Dow Corning Corporate. In this method, the fabric sample is placed together with a nutrient solution inoculated into an Erlenmeyer flask. For this experiment, the procedure was slightly modified, the mixture was stirred for 24 hours instead of 1 hour and the organism used was Kaspergillus niger instead of Klensiella pneumoniae. The percent reduction is determined by counting the organisms at a zero time and at the end of the experiment. The percent reduction found in this example was 99.98%. It will be apparent to those skilled in the art that various modifications and variations may be made in the present invention without departing from the scope and spirit of the invention. Other embodiments of the invention will be apparent to those skilled in the art upon consideration of the specification and practice of the invention described herein. It is intended that the specification and examples be considered as illustrative only, the true scope and spirit of the invention being indicated by the claims. It should be understood that the examples and embodiments described herein are for illustrative purposes only and that various modifications and changes in light thereof will be suggested by those skilled in the art to be included within the spirit and field of vision of this application. and scope of the claims.
Claims (37)
1. - A composition comprising a mixture of: a) an organosilane of the formula RnSiX4_n wherein n is an integer from 0 to 3, each R is independently a non-hydrolysable organic group, and each X is independently a hydrolysable group; with b) an organic carbonate.
2. The composition according to claim 1, further characterized in that n is an integer from 0 to 2; each R of the organosilane formula is independently alkyl, alkyl or aromatic alcohol; each X is independently hydroxyl, alkoxy, halogen, acetyl, acetoxy, acyl, acyloxy, a hydroxy solid or liquid polymer portion, polyglycol or polyalkyl ether; and said organic carbonate is of the formula: wherein each R of the carbonate formula is independently, alkyl, alkyl glycol a cyclic molecule, a heterocyclic molecule; alkyl alcohol, polyglycol, alkyl glycol, cyclic alcohol, heterocyclic alcohol or polyalkyl ether; optionally, said cyclic alcohol or heterocyclic alcohol is substituted with an alkyl or alkyl alcohol.
3. The composition according to claim 1, further characterized in that the organosilane is of the formula II, III, IV or V (R1) 3SiR2N + (R3) (R4) (R5) Y- (II) (R1) 3SiR2N (R3) (R4) (III) (R1) 3SiR2R35 ("V) (RI) 3Si (R36) (R37) (V) wherein each R- | is independently halogen or RgO, wherein RQ is selected from the group consists of the following: H, alkyl, acetyl, acetoxy, acyl, acyloxy, glycol, polyglycol, alkyl glycol, alkyl polyglycol, a monoester formed by the bond of a carbonic acid of 1 to 24 carbon atoms with glycol or polyglycol, alkyl, phenolics substituted with an alkyl of from about 1 to 24 carbon atoms and their sorbitan ethers and esters and their ethers with polyalkyl ether: R35 is Rg, H, halogen, NH2 (CH2) 2NHR2, NH2R2, C3H5O2R2, C4H5O2R2. ) P (0) R2 or CICH2C6H4R2; R36 V R37 are independently R35, halogen, H, alkyl of 1 to about 4 carbon atoms, isobutyl, phenyl or n-octyl; R2 is Rg, benzyl, vin ilo or alkyl, R3 and R4 are independently R35, alkyl alcohol, alkoxy, alkyl or a cyclic molecule; or R3 and R4 together can form a morpholine or a cyclic or heterocyclic molecule;, R5 is alkyl alcohol, R35 is C ^ CgHs, polyglycol, alkyl, alkoxy, perfluoroalkyl, perfluoroalkylsulfonate or perfluoroalkylcarboxylate, and Y is a suitable anionic portion to form the salt of the compound of the formula II, III, IV or V.
4. The composition according to claim 3, further characterized in that R3 and R4 together can form a morpholine or a five to seven membered cyclic or heterocyclic ring, unsaturated or saturated of the formula VI: -R3- (R7) k -R4- (VI) wherein k is an integer from 0 to 2, wherein R7, wherein the ring is saturated, is CH2, O, S, NH , NH2 +, NCH2CH2NH2, NCH2CH2NH3 +, NCH2CH_2N (R8) (R9), NCH2CH2N + (R8) (R9) (R1o), N (alkyl), N (aryl), N (benzyl), wherein each R8, Rg and R10 is independently benzyl, R37, polyglycol, alkyl alcohol, alkoxy or alkyl; and R7, wherein the ring is unsaturated, is CH, N, N + H, N + (alkyl), N + (aryl), N + (benzyl), N-CH2-N, N + H-CH2-N, N + (alkyl) -CH2-N, N + (aryl) -CH2-N, or N + (benzyl) -CH2N, wherein the ring is unsubstituted or substituted with alkyl, ester, aldehyde, carboxylate, amide, thionamide, nitro, amine or halide; optionally, the ring of formula VI represents R3 or R4, independently, with the nitrogen of the ring of formula II or III replaced by CH or CH2; and R5 is as in claim 3 or a ring of five to seven members of formula V as described above.
5. The composition according to claim 3, further characterized in that R5 is a ring of five to seven members of the formula V as described in claim 4.
6. - A water stable composition comprising the composition of claim 1 and water.
7. The composition according to claim 1, further characterized in that the organosilane is 3- (trimethoxysilyl) propyl-dimethyloctadecylammonium chloride.
8. A composition for treating a substrate, comprising a vehicle and an effective amount of the composition of claim 1.
9. The composition according to claim 7, further characterized in that the vehicle is different from water.
10. The composition according to claim 1, further characterized in that the organosilane is 3- (trimethoxysilyl) propylmethyldi (decyl) ammonium chloride, 3- (trimethoxysilyl) propyl-dimethyloctadecylammonium chloride, 3-chloropropyltrimethylsilane, 3-chloropropyltrimethoxysilane, octadecyltrimethoxysilane or perfluorooctyltriethoxysilane.
11. The composition according to claim 1, further characterized in that the organosilane is (CH30) 3S (CH2) 3N + (CH3) 2C18H37C | -, (CH30) 3S (CH2) 3N + (CH3) 2C18H37Br, (CH30) 3S (CH2) 3N + (C1oH2l) CH3C | -, (CH30) 3Si (CH2) 3N + (C1oH2i) CH3Br, (CH30) 3S (CH2) 3N + (CH3) 3C | -, (CH30) 3Si (CH2) 3N + (CH3) 2C8H17C | -, (CH30) 3S (CH2) 3N + (CH3) 2C10H21 C | -, (CH30) 3S (CH2) 3N + (CH3) 2C12H25C | -I (CH30) 3S (CH2) 3N + (CH3) 2C14H29C | -) (CH30) 3Si (CH2) 3N + (CH3) 2C16H33C | -, (CH30 ) 3Si (CH2) 3N + (CH3) 2C2? H4l C | -, (CH30) 3Si (CH2) 3N + (C4H9) 3C | -, (CH3O) 3Si (CH2) 3N + (C2H5) 3C | -, (CH3CH2O) 3Si (CH2) 3N + (CH3) 2C18H27C | -, (CH30) 3Si (CH2) 3NHC (0) (CF2) 6CF3, (CH30) 3Si (CH2) 3NHC (0) (CF2) 8CF3, (CH30) 3YES (CH2) 3NHC (0) (CF2) 10CF3, (CH30) ) 3S (CH2) 3NHC (0) (CF2) 12CF3, (CH30) 3Si (CH2) 3NHC (0) (CF2) 14CF3, (CH30) 3YES (CH2) 3NHC (0) (CF2) 16CF3, (CH30) ) 3S¡ (CH2) 3NHS02 (CF2) 7CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 6CH3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 8CH3, ( CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) ioCH3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 12CH3, (CH3O ) 3 Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O) (CH2) l4CH3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O) (CH2) 16CH3, (CH30) 3 Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 6CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 8CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2)? OCF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) i2CF3, (CH30) 3YES (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 14CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) i6CF3, (CH3?) 3S (CH2) 3N + (CH3) 2 (CH2) 3NHS? 2 (CF2) 7CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS? 2 (CF2) 9CF3, (CH30) 3YES (CH2) ) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 11 CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS? 2 (CF2) i3CF3, (CH3?) 3Si (CH2) 3N + ( CH3) 2 (CH2) 3NHS2 (CF2) i5CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS? 2 (CF2) gCF3, (CH3?) 3Si (CH2) 3NHC6H4COOH, (CH30) 3S (CH2) 3NHCgH4COOCH3 (CH3?) 3Si (CH2) 3NHC H4COOC2H5? (CH30) 3Si (CH2) 3NHC H4COOC3H7 (CH3?) 3Si (CH2) 3NHC6H4COOC4H9j (CH3?) 3Si (CH2) 3NHCgH4COOCH2CgH5 (CH3?) 3Si (CH2) 3NHC H4COOCH2C? H4NH2) (CH3?) 3Si (CH2) 3NHCgH4COOCH2CgH4N (CH3) 2j (CH30) 3Si (CH2 3NHC6H4COOCH2CgH4N (CH2CH3) 2? (CH3?) 3S (CH2) 3NHC6H4COOCH2C H4N + (CH3) 3 Y ". (CH3?) 3S (CH2) 3NHC H4COOCH2CgH4N + (CH2CH3) 3 Y ". (CH3?) 3S (CH2) 3NCH3C6H4COOH, (CH3?) 3Si (CH2) 3NCH3C H4COOCH j (CH3?) 3Si (CH2) 3NCH3CgH4COOC2H5j (CH3?) 3Si (CH2) 3NCH3CgH4COOC3H7? (CH3?) 3Si (CH2) 3NCH3CgH4COOC4H9j (CH3?) 3Si (CH2) 3NCH3CgH4COOCH2CgH5? (CH3?) 3 Si (CH2) 3NCH3C6H4COOCH2C6H4NH2? (CH3?) 3 Si (CH2) 3NCH3C6H4COOCH2CgH4N (CH3) 2 > (CH30) 3S (CH2) 3NCH3CgH4COOCH2CgH4N (CH2CH3) 2j (CH3?) 3Si (CH2) 3NCH3CgH4COOCH2CgH4N + (CH3) 3 Y ~. (CH 3?) 3 Si (CH 2) 3 NCH 3 C 6 H 4 COOCH 2 C 6 H 4 N + (CH 2 CH 3) 3 Y ". (CH30) 3Si (CH2) 3N + (CH3) 2C6H4COOH Y "(CH30) 3Si (CH2) 3N + (CH3) 2CgH4COOCH3 Y- (CH3?) 3Si (CH2) 3N + (CH3) 2CgH4COOC2H5 Y- (CH3?) 3Si ( CH2) 3N + (CH3) 2CgH4COOC3H7 Y- (CH3?) 3Si (CH2) 3N + (CH3) 2CgH4COOC4H9 Y "(CH30) 3Si (CH2) 3N + (CH3) 2CgH4COOCH2C6H5 Y- (CH30) 3Si (CH2) 3N + (CH3) 2CgH4COOCH2CgH4NH2 Y- (CH30) 3Si (CH2) 3N + (CH3) 2CgH4COOCH2C6H4N (CH3) 2 Y- (CH3) 3Si (CH2) 3N + (CH3) 2CgH4COOCH2CgH4N (CH2CH3) 2 Y- (CH30) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N + (CH3) 3? -? - (CH30) 3Si (CH2) 3N + (CH3) 2CgH4COOCH2CgH4N + (CH2CH3) 3 YY- (CH30) 3Si (CH2) 3NC2H5C6H4COOH, (CH30) 3Si (CH2) 3NC2H5C H 4 COOCH 3 (CH 3 O) 3 Si (CH 2) 3NC 2 H 5 C 6 H 4 COOC 4 H 9, (CH 3?) 3 Si (CH 2) 3 NC 2 H 5 C 6 H 4 COOC 3 H 7? (CH30) 3S (CH2) 3NC2H5C6H4COOC4H9j (CH30) 3Si (CH2) 3NC2H5CgH4COOCH2CgH5j (CH3?) 3Si (CH2) 3NC2H5C H4COOCH2CgH4NH2; (CH30) 3S (CH2) 3NC2H5C H4COOCH2C H4N (CH3) 2? (CH3?) 3 Si (CH2) 3NC2H5C? H4COOCH2C H4N (CH2CH3) 2? (CH30) 3S (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH3) 3 Y-. (CH3O) 3S (CH2) 3NC2H5C H4COOCH2C6H4N + (CH2CH3) 3 Y ". (CH3?) 3S (CH2) 3N + (C2H5) 2C6H4COOH Y ". (CH3?) 3S (CH2) 3N + (C2H5) 2C6H4COOCH3 Y-. (CH30) 3 Si (CH2) 3N + (C2H5) 2C6H4COOC2H5 Y ". (CH30) 3 Si (CH2) 3N + (C2H5) 2CgH4COOC3H7 Y ". (CH3?) 3 Si (CH2) 3N + (C2H5) 2C H4COOC4H9 Y-. (CH3?) 3 Si (CH2) 3N + (C2H5) 2C6H4COOCH2CgH5 Y ". (CH30) 3S (CH2) 3N + (C2H5) 2C6H4COOCH2C H4N2 Y-. (CH30) 3S (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N (CH3) 2 Y ". (CH30) 3 Si (CH2) 3N + (C2H5) 2C6H4COOCH2CgH4N (CH2CH3) 2 Y ". (CH3?) 3S (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N + (CH3) 3? -? -. (CH3?) 3S (CH2) 3N + (C2H5) 2CgH4COOCH2C6H4N + (CH2CH3) 3 Y-Y-. (CH3CH20) 3Si (CH2) 3NHCgH4COOH, (CH3CH20) 3Si (CH2) 3NHC H4COOCH3j (CH3CH2?) 3Si (CH2) 3NHC6H4COOC2H5j (CH3CH2?) 3Si (CH2) 3NHC6H4COOC3H7; (CH3CH2?) 3Si (CH2) 3NHC6H4COOC4H9j (CH3CH2?) 3Si (CH2) 3NHC6H4COOCH2C6H5? (CH3CH2?) 3 Si (CH2) 3NHC6H4COOCH2C H4NH2) (CH3CH2?) 3 Si (CH2) 3NHC6H4COOCH2C H4N (CH3) 2; (CH3CH2?) 3 Si (CH2) 3NHC H4COOCH2CgH4N (CH2CH3) 2? (CH3CH2?) 3Si (CH2) 3NHC H4COOCH2C6H4N + (CH3) 3 Y- (CH3CH2?) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH2CH3) 3 Y- (CH3CH2?) 3Si (CH2) 3NCH3CgH4COOH, (CH3CH20) 3Si (CH2) 3NCH3C6H4COOCH3) (CH3CH20) 3Si (CH2) 3NCH3C6H4COOC2H5;(CH3CH2?) 3Si (CH2) 3NCH3C6H4COOC3H7j (CH3CH20) 3S¡ (CH2) 3NCH3CgH4COOC-4H9j (CH3CH2?) 3Si (CH2) 3NCH3C6H COOCH2C6H5) (CH3CH20) 3 Si (CH2) 3NCH3C6H4COOCH2C6H4NH2, (CH3CH2?) 3Si (CH2) 3NCH3CgH4COOCH2C6H4N ( CH3) 2j (CH3CH2?) 3 Si (CH2) 3NCH3CgH4COOCH2CgH4N (CH2CH3) 2 > (CH3CH2?) 3 Si (CH2) 3NCH3C H4COOCH2CgH4N + (CH3) 3 Y ". (CH3CH2?) 3 Si (CH2) 3NCH3C H4COOCH2CgH4N + (CH2CH3) 3 Y ". (CH3CH2?) 3 Si (CH2) 3N + (CH3) 2CgH4COOH Y ". (CH3CH2?) 3 Si (CH2) 3N + (CH3) 2CgH4COOCH3 Y". (CH3CH20) 3 Si (CH2) 3N + (CH3) 2CgH4COOC2H5 Y ". (CH3CH2?) 3 Si (CH2) 3N + (CH3) 2C6H4COOC3H7 Y ". (CH3CH2?) 3 Si (CH2) 3N + (CH3) 2C6H4COOC4H9 Y ". (CH3CH2O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H5 Y ". (CH3CH2?) 3Si (CH2) 3N + (CH3) 2CgH4COOCH2CgH4NH2 Y" » (CH 3 CH 2?) 3 Si (CH 2) 3 N + (CH 3) 2 C H 4 COOCH 2 C H 4 N (CH 3) 2 Y ". (CH3CH2?) 3 Si (CH2) 3N + (CH3) 2CgH4COOCH2C6H4N + (CH3) 3? -? -, (CH3CH20) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2CgH4N + (CH2CH3) 3 Y ~ Y-. (CH3CH2?) 3 Si (CH2) 3NC2H5C H4COOH, (CH3CH2?) 3 Si (CH2) 3NC2H5C6H4COOCH3? (CH3CH2?) 3Si (CH2) 3NC2H5C6H4COOC2H5? (CH3CH2?) 3Si (CH2) 3NC2H5CgH4COOC3H7j (CH3CH2?) 3Si (CH2) 3NC2H5CgH4COOC4H9) (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOCH2C6H5? (CH3CH20) 3Si (CH2) 3NC2H5C H4COOCH2C H4NH2? (CH3CH2?) 3 Si (CH2) 3NC2H5C H4COOCH2C6H4N (CH3) 2; (CH3CH2?) 3Si (CH2) 3NC2H5CgH4COOCH2C6H4N (CH2CH3) 2j (CH3CH2?) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH3) 3 Y ". (CH3CH2?) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH2CH3) 3 Y". (CH3CH2?) 3 Si (CH2) 3N + (C2H5) 2CgH4COOH Y-. (CH3CH2?) 3 Si (CH2) 3N + (C2H5) 2C6H4COOCH3 Y-. (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2CgH4COOC2H5? - > (CH3CH20) 3Si (CH2) 3N + (C2H5) 2CgH4COOC3H7 Y ". (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOC4H9 Y-. (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2CgH4COOCH2CgH5 Y-. (CH3CH2?) 3 Si (CH2) 3N + (C2H5) 2C H4COOCH2C H4NH2 Y ". (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2CgH4COOCH2C6H4N (CH3) 2 Y-. (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y ". (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N + (CH3) 3? -? -, or (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2CgH4N + (CH2CH3) 3 Y -? -.
12. The composition according to claim 1, further characterized in that the organosilane is NH 2 (CH 2) 2 NH (CH 2) 3 Si (OCH 3) 3, NH 2 (CH 2) 3 Si (OCH 3) 3, NH 2 (CH 2) 3 Si (OCH 2 CH 3) 3, CI (CH 2) 3 Si (OCH 3) 3, CI (CH 2) 3 Si (OCH 2 CH 3) 3, CI (CH 2) 3 SiCl 3, C 3 H 5 2 (CH 2) 3 Si (OCH 3) 3, C 3 H 5 ? 2 (CH2) 3Si (OCH2CH3) 3, C4H5? 2 (CH2) 3Si (OCH3) 3, C4H5? 2 (CH2) 3Si (OCH2CH3) 3, CH3SiHCI2, NaO (CH30) P (0) - (CH2) 3Si (OH) 3, SiHCl3, n-2-vinylbenzylamino-ethyl-3-aminopropyltrimethoxysilane HCL, H2C = CHSi (OCOCH3) 3, H2C = CHSi (OCOCH3) 3, H2C = CHSi (OCH2CH3) 3 H2C = CHSiCI3l (CH3) 2SiCl2, (CH3) 2Si (OCH3) 2, (C6H5) 2SiCl2, (C2H5) SiCl3, (C2H5) Si (OCH3) 3, (C2H5) Si (OCH2CH3) 3, isobutyltrimethoxysilane, n-octyltriethoxysilane, CH3 ( CgH5) SiCl2, CH3SÍCI3, CH3Si (OCH3) 3, CgH5SiCl3, CgH5Si (OCH3) 3, C3H7SiCI3l C3H7Si (OCH3) 3, SiCl4, CICH2CgH4CH2CH2SiCl3n, CICH2C H4CH2CH2Si (OCH3) 3, CICH2CgH4CH2CH2Si (OCH2CH3) 3, decyltrichlorosilane, dichloromethyl (4-methylphenethyl) silane, diethoxymethylsilane, [3- (diethylamino) propyl] trimethoxysilane, 3- (dimethoxymethylsilyl) -l-propanethiol, dimethoxymethylvinylsilane, 3- [tris (trimethyryl-oxy) methacrylate Silyl] propyl trichloro [4- (chloromethyl) phenyl] silane, methylbis (trimethylsilyloxy) vinyl silane, methyltripropoxysilane, and trichlorocyclopentylsilane.
13. A composition comprising the organosilane of claim 1 linked to a compound useful for UV protection, wherein said compound is para-aminobenzoic acid, aminobenzoic acid, salicylic acid, cinnamic acid, benzoic acid or benzophenone, or derivatives thereof. the same; optionally, said compound is in the form of anhydride or in the form of mixed anhydride; wherein said binding is a result of the removal of an atom or group of said compound and said organosilane, and forms a bond with the five valences produced from said removal.
14. - The composition according to claim 1, formed from the mixing of an organosilane of the formula II, III, IV or V (R1) 3SiR2N + (R3) (R4) (R5) Y- (II) (R1) 3SiR2N (R3) (R4) (III) (R?) 3SiR2R35 (HV) (R1) 3Si (R36) (R37) (V) wherein each Rj is independently halogen or RgO, wherein Rg is selected from the group consisting of the following: H, alkyl, acetyl, acetoxy, acyl, acyloxy, polyglycol; alkyl glycol; alkyl polyglycol; the monoester formed by the bond of a carbonic acid of 1 to 24 carbon atoms with glycol or polyglycol; phenolics substituted with an alkyl of 1 to 24 carbon atoms and their ethers and sorbitan esters and their ethers; and polyalkyl ether; R35 is Rg, H, halogen, NH2 (CH2) 2 HR2, NH2R2, C3H5O2R2, C4H5O2R2, NaO (CH3?) P (O) R2 or CICH2C H4R2; R3g and R37 are independently R35, halogen, H, alkyl of 1 to 8 carbon atoms, acrylic, vinyl, acetylenic, benzyl, styryl, propenyl, isobutyl, phenyl or n-octyl; R2 is benzyl, vinyl or alkyl; R3 and R4 are independently lower alkyl alcohol, lower alkoxy of 1 to 4 carbon atoms, or alkyl, or R3 and R4 together can form a morpholine or a cyclic or heterocyclic molecule; R5 is lower alkyl alcohol, CH2C H5, polyglycol, alkyl, alkoxy, perfluoroalkyl, perfluoroalkylsulfonate, perfluoroalkylcarboxylate, and Y is a suitable anionic portion to form the salt of the compound of formula II, III, IV or V with an organic carbonate.
15. The composition according to claim 14, further characterized in that R3 and R4 together can form a morpholine or a five to seven membered unsaturated or saturated cyclic or heterocyclic ring of the formula VI: -R3- (R7) k-R4 - (VI) where k is an integer from 0 to 2, where R7, where the ring is saturated, is CH2, O, S, NH, NH2 +, NCH2CH2NH2, NCH2CH2NH3 +, NCH2CH_2N (R8) (R9), NCH2CH2N + (R8) (R9) (R10), N (alkyl), N (aryl), N (benzyl), wherein each R8, Rg and RJ Q is independently benzyl, R37, polyether, lower alkyl alcohol of 1 to 4 atoms carbon, lower alkoxy of 1 to 4 carbon atoms, or alkyl of 1 to about 22 carbon atoms; and R7, wherein the ring is unsaturated, is CH, N, N + H, N + (alkyl), N + (aryl), N + (benzyl), N-CH2-N, N + H-CH2-N, N + ( alkyl) -CH2-N, N + (aryl) -CH2-N, or N + (benzyl) -CH2N; wherein the ring is unsubstituted or substituted with alkyl of 1 to 22 carbon atoms, ester, aldehyde, carboxylate, amide, thionamide, nitro, amine or halide; optionally, the ring of formula VI represents R3 or R4, independently, with the nitrogen of the ring of formula II or formula III replaced by CH or CH2; and R5 is as in claim 13 or a ring of five to seven members of formula VI as described above.
16. The composition according to claim 14, further characterized in that R5 is a ring of five to seven members of the formula V as described in claim 14.
17. - The composition according to claim 14, which is an aqueous composition.
18. A method of treating a substrate, comprising contacting the substrate with a sufficient amount of the composition of claim 1 for a period sufficient to treat the substrate.
19. A method of staining and treating a substrate, comprising contacting the substrate with an aqueous composition comprising an aqueous soluble dye suitable for dyeing a substrate and the composition formed upon mixing: a) an organosilane of the formula RnSiX4_n wherein n is an integer from 0 to 3, each R is independently a non-hydrolysable organic group, and each X is independently a hydrolysable group; with b) an organic carbonate.
20. A method for treating a food article antimicrobially, comprising contacting the food article with an effective amount of a product formed upon mixing: a) an antimicrobial organosilane of the formula RnSiX4_n wherein n is an integer of 0 to 3, each R is independently a non-hydrolysable organic group, and each X is independently a hydrolysable group; with b) an organic carbonate.
21. A method for antimicrobially coating a fluid container for containing a human or animal consumable product, comprising contacting the container with an effective amount of the product formed upon mixing: a) an antimicrobial organosilane of the formula RnSiX4_n wherein n is an integer from 0 to 3, each R is independently a non-hydrolysable organic group, and each X is independently a hydrolysable group; with b) organic carbonate.
22. A method for antimicrobially coating a medical latex article for use in a human or animal process, comprising contacting the article with an effective amount of the product formed upon mixing: a) an antimicrobial organosilane of the formula RnSiX4-n wherein n is an integer from 0 to 3, each R is independently a non-hydrolysable organic group, and each X is independently a hydrolysable group; with b) an organic carbonate.
23. The method according to claim 22, further characterized in that the article is a surgical glove.
24.- A method to antimicrobially treat a substrate selected from the group consisting of a concrete tube, food article, fluid container, glove, bathroom curtain, bathroom door, latex medical article, toothbrush, comb, hairbrush, denture or other orthodontic adhesive, a Spa or pool filter, an air filter, an HVAC air system, a cabin air system, a marble item, a statue, an exposed work of art, a plastic cover made of PE, PP or polyester, a fiberglass article coated with silicone or TEFLONR, a Dryvitt finish, a stucco finish, combined cotton, a bio-film, a bio- adhesive, a single-layer roof, a roofing and a fiberglass reinforcement product consisting of contacting the substrate with an effective amount of the product formed upon mixing: a) an antimicrobial organosilane of the formula Rn iX4_n wherein n is an integer from 0 to 3, each R is independently a non-hydrolysable organic group, and each X is independently a hydrolysable group; with b) an organic carbonate.
25. A method for antimicrobially increasing a rubbing alcohol product, a flower preservative, or a waterproof solution, which consists of mixing an effective amount of the product formed when mixing with the product: a) an antimicrobial organosilane of the formula RnSiX4_n wherein n is an integer from 0 to 3, each R is independently a non-hydrolysable organic group, and each X is independently a hydrolyzable group; with b) an organic carbonate.
26. A method for treating a substrate making it resistant to stains, comprising contacting the substrate with an effective amount of the composition formed upon mixing: a) an antimicrobial organosilane of the formula RnSiX4_n wherein n is an integer of 0 to 3, each R is independently a non-hydrolysable organic group, and each X is independently a hydrolysable group; with b) organic carbonate.
27. A method for making an organosilane of the formula RnSiX4_n, wherein n is an integer from 0 to 3, preferably 0 to 2; R is independently a non-hydrolysable organic group; and each X is independently a hydrolysable group; which consists in mixing the starting materials of the organosilane synthesis in an aqueous solution in the presence of an organic carbonate.
28. - A water-stable composition comprising from about 0.001% to about 26% organosilane and from about 0.001% to about 26% ethylene carbonate and from 99.9% to about 48% water.
29. A water-stable composition comprising from about 1.6% to about 56% organosilane and from about 44% to about 99% water, wherein said organosilane solution comprises about 49% silane concentrate , about 32% glycol ether DB and about 37% propylene carbonate.
30. A water-stable composition comprising from about 1% to about 55% organosilane and from about 45% to about 99% water, wherein said organosilane solution comprises about 50% silane concentrate , about 12% glycol ether DB and about 38% propylene carbonate.
31. A composition comprising from about 7% to about 55% of an organosilane solution and from about 45% to about 93% of water, wherein said organosilane solution comprises from about 0% to about 50% of silane concentrate and from about 0% to about 50% propylene carbonate.
32.- A composition comprising organosilane, carbonate 7 of propylene and water.
33.- A composition comprising organosilane, ethylene carbonate and water.
34.- A method for making an organosilane of the formula Rn iX4-n, wherein n is an integer from 0 to 3, preferably 0 to 2; R is independently a non-hydrolysable organic group; and each X is independently a hydrolysable group; which consists of mixing the starting materials of organosilane synthesis in the presence of an organic carbonate solvent.
35. The method according to claim 34, further characterized in that the organosilane starting materials comprise a silane component and an amine.
36. The method according to claim 35, further characterized in that the silane component is 3-chloropropyltrimethoxysilane and the amine is dimethyloctadecylamine.
37. The method according to claim 34, further characterized in that didecyl-N-3- (trimethoxysilyl) propane chloride is synthesized.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60/052,888 | 1997-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA00000625A true MXPA00000625A (en) | 2001-03-05 |
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