MXPA98003600A - Organosilan compounds stabilized in water and methods to use - Google Patents
Organosilan compounds stabilized in water and methods to useInfo
- Publication number
- MXPA98003600A MXPA98003600A MXPA/A/1998/003600A MX9803600A MXPA98003600A MX PA98003600 A MXPA98003600 A MX PA98003600A MX 9803600 A MX9803600 A MX 9803600A MX PA98003600 A MXPA98003600 A MX PA98003600A
- Authority
- MX
- Mexico
- Prior art keywords
- ch3o
- carbon atoms
- alkyl
- independently
- organosilane
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 88
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 159
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 96
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 63
- 239000000758 substrate Substances 0.000 claims abstract description 62
- 229920005862 polyol Polymers 0.000 claims abstract description 59
- 150000003077 polyols Chemical class 0.000 claims abstract description 59
- 125000004429 atoms Chemical group 0.000 claims abstract description 47
- -1 organosilane compounds Chemical class 0.000 claims abstract description 40
- 238000002156 mixing Methods 0.000 claims abstract description 36
- 125000000962 organic group Chemical group 0.000 claims abstract description 32
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims abstract description 32
- 235000013305 food Nutrition 0.000 claims abstract description 27
- 239000011248 coating agent Substances 0.000 claims abstract description 16
- 238000000576 coating method Methods 0.000 claims abstract description 16
- 238000004043 dyeing Methods 0.000 claims abstract description 11
- 239000012530 fluid Substances 0.000 claims abstract description 5
- 229920000126 Latex Polymers 0.000 claims abstract description 4
- 239000004816 latex Substances 0.000 claims abstract description 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 239000000243 solution Substances 0.000 claims description 46
- 150000001720 carbohydrates Chemical class 0.000 claims description 40
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 38
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- 239000000543 intermediate Substances 0.000 claims description 31
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 10
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- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 claims description 6
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 claims description 6
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 6
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- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000006210 lotion Substances 0.000 claims description 6
- 239000000594 mannitol Substances 0.000 claims description 6
- 235000010355 mannitol Nutrition 0.000 claims description 6
- 239000002777 nucleoside Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 229920001817 Agar Polymers 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 5
- 239000005715 Fructose Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 235000010323 ascorbic acid Nutrition 0.000 claims description 5
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
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- CIWBSHSKHKDKBQ-DUZGATOHSA-N (+)-Ascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims description 3
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 claims description 3
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- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims description 3
- YZNQITSGDRCUKE-UHFFFAOYSA-N 1-chloropropane Chemical group [CH2]CCCl YZNQITSGDRCUKE-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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Abstract
The present invention relates to: composition formed by mixing an organosilane, optionally having a non-hydrolysable organic group, but having one or more hydrolysable groups, with a polyol containing at least two hydroxy groups, wherein at least two of the groups hydroxy are separated by no more than two intermediate atoms, organosilane compounds stabilized in water, a stable composition in water, formed from the polyol and the organosilane or the compound and water, a method for treating a substrate by mixing or contacting the substrate with the product, the compound or the composition of this invention, for a period of time sufficient for the treatment of the substrate, a locked substrate, having adhered thereto the product, the compound or the composition of this invention: a method for dyeing and treat a substrate, a method for antimicrobially treating a food article, a method for antimicrobially coating a rec fluid, a method for antimicrobially coating a medical latex article, a method for forming a siloxane in the presence of a stabilized
Description
• *: •
ORQUANOSILAN COMPOUNDS STABILIZED EM AQUA AND METHODS FOR
USING THEM
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
The invention relates to organosilane compounds to 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 compounds, products and compositions and methods of treatment using the compounds, products and compositions.
BACKGROUND
The organosilanes of the general formula R "S X. ^ _" 'Where n is an integer from 0 to 3 »but more generally O to 2 (where» when n is 3 »the organosilanes can only be dimerized)» R It is a non-hydrolysable organic group. such as »but without limitation to them» alkyl, aromatic »uncunal organ or a combination of them» and X is alkoxy »such as methoxy or ethoxy» are susceptible to self-condensation »which makes these organs unstable lanos in water» during commercially relevant periods of time. Additionally »X can be a halogen» such as Cl. Br or I »and is similarly reacted 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, H, H, O, acetic acid or an unsubstituted or substituted carboxylic acid, and form the hydroxylated compound, but prone to condensation. For the organosilanes ^ SiX ^. ^ "Where n is an integer from 0 to 2» the hydrolysis of the first two groups X with
• 5 10 water produces a species that carries units -Si (OH) 3- »which can self-condense through the hydroxyl portions to linear and / or cyclic oligomers that have the partial structure H0-Si- (0-Si) ) mm-0-Si-0-Si-0-Si-OH. where mm is an integer such that an oligomer is formed. For those
cases »RSiXa» the hydrolysis of the third group X generates a s lanotriol (RSi (OH) 3), which produces insoluble organosilicon chemicals »by means of the linear and / or cyclic autocondensation f of the Si units (OH ). This "water-induced" self-condensation generally hinders the storage of most
of the organosilanes RrlSiX -, _ "» where n varies from O to 2 »inclusive» in water. Except for some organosilanes that can be stable in very dilute solutions "at specific pH scales" the use of aqueous solutions of most organosilanes requires the use of freshly prepared solutions.
A relevant commercial example of an organosilane suffering from such undesirable self-condensation is the Dow Corning 5700 antimicrobial (Dow Corning Corporation).
Midland »MI» E. U. A.). The literature describes the active ingredient of Dow Corning 5700 as 3-s (trimethoxy-1-l) propyl-dimethoctadec-lamonium chloride. However, in
In the case of aqueous media, it is believed that the correct active ingredient will most likely be 3- (trihydroxy-1-yl) -propyl-di-eti-loctadeci-onium chloride. However, chloride 3-
(trimetoxisi li 1) propil-dimeti loctadeci onio is an integrated antimicrobial system »activated with water, which is capable of
IO join a variety of natural and synthetic substrates, including fibers and fabrics, to produce a surface coating or durable fabric. The 3- (trimethoxis 1 i 1) propyl-dimeti loctadeci lamonium chloride is prepared by quaternizing dimethyl loctadec with 3-
chloropropylmethoxide? Is tin. The quaternary ammonium portion with hydrocarbon chain of IB carbon atoms »of the molecule» possesses
- long-acting antimicrobial properties, and provides initial association with the surface of the substrate by means of
ionic ligatures and / or electrostatic interaction. Preferably the treated surface is permanently coated with a covalently bound octadecylammonium ion, which provides a durable, long-acting antimicrobial coating that is capable of destroying microbes
that are in contact with the surface. Unfortunately, as noted above, "lanos in water" organs such as the activated mixture of 3- (trimethoxysilyl) propyl dimethyl chloride and water, are generally unstable and prone to self-condensation. For example, the mixture of 3- (trimethoxy-1-l) propyl-dimethoctadecyammonium chloride and water begins to lose effect as rapidly as in four to eight hours. The formation of gel in these formulations and other similar silane in water »begins to occur in even shorter times. The limitations of these organosilanes in
Aqueous media are further described in U.S. Patent No. 5,411,585, the contents of which are incorporated herein by this reference. In addition »such products are notable for their difficulty in stirring them during the addition of the silane to water. However, according to the
In accordance with the present invention, clear aqueous gels are considered as useful compositions. The use of silicon compounds with quaternary ammonium »as anti-microbial agents» according to the prior art »is well known and is taught in a large
variety of US patents »for example: 3,560,385» 3 »794,736» 3 »8914» 739 »whose contents are hereby incorporated by reference. It would also be shown 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» US patents 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» 26B »whose contents are incorporated in this by this reference). Although these compounds of silicon and quaternary ammonium have been used to sterilize or disinfect many surfaces, their use is still limited due to their toxicity, which is often the result of the solvent system used to supply the compound, to the need for solution in solvent (for example, Dow Corning antimicrobial agents contain 50J of methane!) »short-term stability (the stability of aqueous silane solutions varies from several hours to several weeks) and poor solubility in water . For example, while 3- (tri-ethoxysilyl) propyl-dimethyloctadecylammonium chloride does not suffer from insol bility in water »it is unstable in water and» more »
because it embarks on 5054 methane !, it is excessively toxic. Many other antimicrobial organosilanes, especially the quaternary ammonium silicon compounds, also present problems associated with physical and health hazards; for example, precautions should be taken to
avoid contact with the skin and eyes, accidental splashes to the surrounding area, flammability and additional manufacturing steps necessary to incorporate these antimicrobial agents into other articles and surfaces "or that result in much manufacturing costs. Taller. Accordingly, there is a need for "long-lived storage stable organosilane products and compositions of water-stable organosilane compositions, whereby, when applied, the active portion of the organosilane is operative for the selected application. In addition »there is a need for compounds» organosilane products and compositions
stable in water »that are essentially non-toxic, non-flammable, uniformly dispersible and simple and economical in their use.
In the provisional application No. 60/016985 a method for producing solutions and compositions of
organosilane stable in water. According to this invention, stablishment is achieved by reacting the organosilane with a polyol containing at least three hydroxy groups, wherein any two hydroxy groups are separated by at least three intermediate atoms. The archetypal example of said
Polyol, described in that application, is pentaerythritol. In the present application, the discovery is disclosed that the compounds having at least. Two hydroxy groups stabilize the aqueous solutions of organs, even though there are less than three atoms that separate
At least two of the hydroxyl groups that are present in the polyol. AND! An archetypal example of the polyols of the present invention is glucose "wherein there are several hydroxy groups" several of which are separated by no more than two intermediate atoms. Consequently »this invention provides a
A much broader range of hydroxy-containing compounds is useful for the stabilization of the organosilane compounds.
BRIEF DESCRIPTION OF THE INVENTION
The present invention satisfies those needs by providing compounds, products (ie, compounds or compositions formed from which a specific reaction is effected) and water-stable organosilane compositions; methods for their use and articles prepared by using
Jt said compounds, products and compositions. The compounds »products and compositions of the present invention are non-toxic, non-flammable, simple and inexpensive. In particular, the present invention provides the product formed from mixing an organosilane of the
formula R "SiX -, _" "where n is an integer from 0 to 3", preferably 0 to 2; each R »i dependently» is a non-hydrolysable organic group »and each X» independently »is a hydrolysable group; with a polyol containing at least two hydroxy groups, wherein any two hydroxy groups of
or less two hydroxy groups present are separated by less than three intermediate atoms. Accordingly, alcohols having at least two hydroxyls; carbohydrates »including monosaccharides» disaccharides »ol gosacár two» polysaccharides; Modified carbohydrates »
including graft and block copolymers; partially alkylated, partially acylated or partially acetylated carbohydrates; carbohydrate oxidation products (eg, glucuronic acid, mucic acid), reduced carbohydrates and substituted carbohydrates (eg, "nuclei das" nucleotides, nucleic acids) are all polyols that are useful in accordance with the present invention. Accordingly, in one embodiment, this invention provides a stable composition in water comprising the product or composition of the invention and water. In another embodiment, the present invention provides a composition for treating a substrate, comprising a carrier and an effective amount of the product or compound of the invention. In yet another embodiment, the present invention provides a method for treating a substrate which comprises mixing the substrate with a sufficient amount of the product, the compound or composition of the invention, for a period of time sufficient for the treatment of the substrate. In an additional embodiment, the present invention provides a treated substrate having the product adhered to it, e! compound or the composition of the invention. Additionally, the present invention provides a method for dyeing and treating a substrate, comprising contacting the substrate with an aqueous composition comprising a soluble aqueous dye suitable for dyeing a substrate, and the product formed by mixing an organosilane with the formula R ^ SiX ^ ,, ,, where n is an integer from 0 to 3 », preferably 0 to 2; each R »independently» is a non-drolizable organic group; and each X, independently, is a hydrolysable group, with a polio! which contains at least two hydroxides which are separated by less than three intermediate atoms, for a period of time sufficient to dye and treat the substrate. In a further embodiment, the present invention provides a method for antimicrobially treating a food article comprising contacting or mixing the food article with an effective amount of the product formed by mixing an antimicrobial organosilane of the formula R "SiX. ^ _ "» Where n is an integer from 0 to 3 »preferably 0 to 2; each R »is independently a non-hydrolysable organic group» and each X »independently» is a hydrolysable group; with a polyol containing at least two hydroxyls that are separated by at least three intermediate atoms "for a period of time sufficient to treat the food article antimicrobially. In yet another embodiment, the present invention provides a method for antimicrobially coating a container for fluid used to contain a human or animal consumable product which comprises contacting the container with an effective amount of the product formed by mixing an antimicrobial organosilane of the formula R "SiX ^ _" "where n is an integer from 0 to 3", preferably 0 to 2; each R »independently» is a non-hydrolysable organic group; and each X. independently "is a hydrolysable group; with a polyol containing at least two hydroxyls that are separated by less than three intermediate atoms; for a period of time sufficient to antimicrobially coat the container. In yet another embodiment, the present invention provides a method for antimicrobially coating a medical latex article for use in a human or animal medical procedure, which comprises contacting the article with an effective amount of the product formed by mixing an antimicrobial organosilane. the formula R ^ SiX ^ ,, ,, where n is an integer of O to 3 »preferably 0 to 2» each R »independently» is a non-hydrolysable organic group; and each X "independently" is a hydrolysable group; with a polyol containing at least two hydroxyls that are separated by less than three intermediate atoms "for a sufficient period of time to anti-microbially coat the article. Yet another embodiment of the present invention provides a method for antimicrobially treating a substrate selected from the group consisting of a concrete tube, a toothbrush, a comb, a hairbrush, a denture, an orthodontic retainer, a filter. of water tank or pool »an air filter» an HVAC air system »an air system for a cabin» an article of marble »a statue» an artistic piece exposed »an HDP plastic cover» an article of fiber glass coated with silicone or with TEFLON * "'» a Dryvitt finish »a stucco finish» a cotton mix »a bio-film» a bio-adhesive »a single-water roof» rolled roof tiles and a product fiberglass reinforcement, comprising contacting the substrate with an effective amount of the product formed by mixing an antimicrobial organism of the formula R ,,, S? X ^ _ "" where n is an integer of O to 3. preferably 0 to 2"each R" i is independently a non-hydrolysable organic group "and each X" independently is a hydrolysable group; with a polio! containing at least two hydroxyls that are separated by less than three intermediate atoms "for a period of time sufficient to treat the article antimicrobially. Additionally, the present invention also provides a method for antimicrobially improving an alcohol product for rubbing a flower preservative or a permeabilizing solution and comprising mixing with the product an effective amount of the product formed by mixing an antimicrobial organolenoate. the formula R ^ SiX. * .. ,, "where n is an integer from 0 to 3», preferably 0 to 2; each R »independently» is a non-hydrolysable organic group; and each X »independently» is a hydro group! can be "with a polyol containing at least two hydroxyls that are separated by less than three intermediate atoms" for a period of time sufficient to improve the article antimicrobially. Another additional embodiment of this invention is a method for forming an organosilane of the formula "SiX ^ _" "wherein n is an integer from 0 to 3", preferably 0 to 2; each R »independently» is a non-hydrolysable organic group and each X »independently» is a hydrolysable group in an aqueous solution »in the presence of a polio! which contains at least two hydroxyls that are separated by less than three intermediate atoms, in an effective amount of the polyol »sufficient to stabilize the organosilane as it is formed from the reactants. Other advantages of the invention will be pointed out partially in the description that follows and in part will be obvious from the description "or can be learned by the routine practice of the invention" as described herein.
The advantages of the invention will be obtained and achieved by means of the elements and combinations indicated in detail in the rei indications that come at the end. It should be understood that both the foregoing general description and the detailed description that follows are exemplary and explanatory only, and are not restrictive for the present invention, as claimed.
DETAILED DESCRIPTION OF THE INVENTION
The present invention will be more readily understood by reference to the following detailed description of the preferred embodiments of the invention. Before the present compounds, products, compositions and methods are described and illustrated, it should be understood that the terminology used herein is for the purpose of describing particular modalities only, and that it is not intended to be limiting. It should be noted that "when used in the descriptive memory and in the claims that come at the end, the singular forms" a "," an "and" the "," the ", include the plural referents, unless the context clearly dictates otherwise. Throughout this descriptive specification, when references are made to publications, the descriptions of these publications are incorporated in their entirety "as a reference in this application, in order to describe more fully the state of the art to which it refers. refers to the present invention. The term "alkyl", when used herein, refers to a saturated hydrocarbon group »branched or unbranched» of 24 carbon atoms »such as methyl (" Me "), ethyl (" Et ")» n -propyl »isopropyl» n-butyl »isobutyl» terbutyl »octyl» decyl »tetradecyl» hexadecyl »eicosyl» tetracosyl and the like. Preferred alkyl groups herein contain from 1 to 12 carbon atoms. The term "lower alkyl" is intended for an alkyl group of 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. The term "cycloalkyl" is intended for a cyclic group of 3 to 8%, preferably 5 or 6 carbon atoms. "Lower alkyl alcohol" refers to lower alkyl having attached thereto one or more hydroxy moieties such as but not limited to: CH2, C5 Qr. > CHßCH (0H) CH 3, CH 4 OH, CH a CH 2 CH 4 OH, CH a CH 2 CH (OH) CH a,
CHaCHaCH (OH) CHaOH, or CHaCH (OH) CH (OH) CH3. The term "alco? I", when used herein refers to an alkyl group attached by means of a single terminal ether bond; that is, an "alkoxy" group can be defined as -OR. where R is the alkyl as defined above
above. A "lower alkoxy" group refers to an alkoxy group containing from 1 to 6. even better "from 1 to 4 carbon atoms. "Polyether" refers to a compound or a portion having multiple ether linkages such as but not limited to: polyethylene glycols or polypropylene glycols. "Ethers
Polyalkylene "refers to alkyls interconnected by" or otherwise possesses multiple ether linkages As used herein "optional" or "optionally" means that the event or circumstance described below may occur or not, and that
The description includes the cases in which said event or said circumstance occurs "and the cases in which they do 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 both the unsubstituted lower alkyl and the lower alkyl in which there is substitution. By the term "effective amount" of a compound "product or composition" as provided herein "is meant a sufficient amount of the compound" of! product or composition to give the desired result. As will be pointed out below, "the exact amount needed will vary from one substrate to another, depending on the particular compound" of the product or composition used; in its administration mode and the like. Thus »it is not always possible to specify an" exact amount ". However, an appropriate effective amount can be determined by one of ordinary skill in the art "informed by the present description" using only routine experimentation. AND! term "aril". when used herein, it refers to a compound or a portion whose molecules have a ring or multiple ring structure, characteristic of benzene, naphthalene, e! phenanthrene »anthracene» etc.; that is to say »the ring of six carbon atoms of benzene or the condensed rings of six carbon atoms of the other aromatic derivatives» including but not limited to: phenyl. benzyl »naphthyl» benzyldene »xyl» styrene. styryl. phenethyl »phenylene» benzenetriol. etc. When used herein, the term "aromatic" refers to the group of unsaturated cyclic hydrocarbons, typified by e! benzene »which have a ring of 6 carbon atoms, which contain three double bonds or multiple connected benzene rings. In addition, ain five-membered cyclic compounds, such as furan (heterocyclic), are analogous to the aromatic compounds. Aromatics include cyclic compounds that are based on a benzene functionality "as specified for" aryl "above. Furthermore, the term "cyclic" is used to refer to all aliphatic or aromatic hydrocarbons "having one or more closed rings" either unsaturated or saturated. Preferably, the cyclic compounds have rings of 5 to 7 carbon atoms, preferably of 6 carbon atoms. These rings can be of three kinds: alicyclic, aromatic ("arene") and heterocyclic. In addition, when used with respect to the compounds or cyclic portions, the term "unsaturated" refers to that compound or portion which possesses at least one double or triple glyph, or which otherwise constitutes a compound or a portion thereof. aromatics Adhere onally »the term" not saturated "refers to the compounds or portions that do not have double or triple bonds, that is to say, where all the valence bonds of an atom, especially carbon, are linked to other atoms. The term "heteroary lo" refers to an aryl in which one or more carbon atoms of a ring have been substituted with a heteroatom, including, but not limited to, 0, N, or S. Similarly, the term "heterocyclic" refers to a cyclic compound or a cyclic portion, wherein one or more of the ring carbon atoms has been substituted with a heteroatom "including, but not limited to, 0, N, or S. As used herein , especially with reference to alkyl and alkoxy, the term "lower" refers to a portion having from 1 to 6 carbon atoms, preferably from 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 that are provided herein for the stated purpose. The appropriate for the stated purpose can be determined by who is an ordinary expert in the field using only routine experimentation. As used herein "substituted" is used to refer "in general" to a carbon atom or a suitable heteroatom having a hydrogen atom or other atom mined and replaced by a different portion. In one embodiment, substitutions of the hydrocarbon hydrogens based on halogen, hydroxy and nitrogen, are contemplated as being within the scope of the present invention for the structures claimed. Add on. it is intended that "substituent" refers to substitutions that do not change the basic and novel utility of the compounds »the products or the underlying compositions of the present invention. "Unsubstituted" refers to a structure in which the reference atom has no additional portion attached to it! nor in replacement of him. As used herein, "branched" is used for reference. in general, to a portion having a carbon chain structure or skeleton, for example, alkyl or alkoxy, wherein the backbone may contain one or more subordinate carbon chain branches. For example, isobutyl, tert-butyl, isopropyl, CH-CH2CH (CH3) (H) CHa.CH3, < H) CHsCHa »CHaíCHJBC (CH3 CHa and would be considered branched portions) In addition» it is intended that the "branched" variations of the portions described here refer to variations that do not change the basic and novel utility of the compounds »the products or the underlying compositions of the present invention. "Non-branched" refers to a structure in which the carbon chain has no branching in it ie in which the carbon chain extends in a direct line. it is used here, the term "acyl" refers to portions derived from organic acid "of the formula RCOX" wherein R is an organic molecule and X, instead of being hydroxy "is replaced by another substituent" preferably a suitable anion.
As used herein, the term "perfluoro" or "perfluoro-analog" refers to a hydrocarbon in which the hydrogen atoms attached to the carbons have been replaced by F. Preferably, but not necessarily, in the perfluoro-analogs »most» if not all »of the H > they are replaced by atoms of F. A "uoro" -analog is contemplated to indicate a hydrocarbon in e! which at least one hydrogen atom bonded to a carbon is replaced by an atom of F. As used herein "" substrate "refers to any article» product or other surface that may be created with the compounds of the invention Preferably as recited hereinafter "under the Uses heading" as described in the examples herein and as specified in the relevant claims which come to the end of this. Suitable substrates are generally characterized as preferably having a negatively charged surface of "oxygen atoms" or any surface capable of adhering or electrostaticly or covalently binding to the compounds or products of the present invention. Preferably the adhesion or binding occurs in the silicon atoms of the organosilane portion of the compounds, the products or the compositions of the present invention; but such a union is not a requirement. Accordingly, when used herein, the term "adhere" is meant to refer to the ionic, covalent, electrostatic or other chemical bonding of a compound, a product or a composition, to a substrate. As used herein, the term "improving antimicrobially" refers to the use of the compounds, products or compositions of the present invention, preferably those in which the organosilane has antimicrobial activity, together with other ingredients, surfactants. You load »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 anti-microbial protection during the particular application. The term "enhance" refers to the addition of the antimicrobial activity to said compositions or solutions "wherein said activity did not previously exist, or to the increase in antimicrobial activity where the compositions or starting solutions inherently possessed antimicrobial activity. As used herein, "hydrolyzable" refers to whether a portion is capable of or "prone to" hydrolysis (ie, the division of the molecule or portion into two or more new molecules or portions) into aqueous media or other media. Suitable "reverse" "non-hydrolysable" refers to portions that are not prone to or capable of hydrolysis in aqueous media or other suitable media.
As used herein, "cationic" is used to refer to any compound or ion having a positive charge. Furthermore, "anionic" is used to refer to any compound or ion that has a negative charge. Additionally, "monovalent" and "d-valent" are used to refer to portions that have valences of one and two, respectively. Additionally, as used herein, the term "salt" is intended to be applied in its generally defined sense as a "compound formed by the replacement of all or part of the hydrogen ions of an acid by one or more cations. from a base. " See, for example, American Heritage Dictionary, definition of "salt" (1981). Accordingly, salts suitable for the present invention can be formed by replacing a hydrogen ion of a portion with a cation, such as K + »Na +, Ca2 +, Mg2 +, etc. Additionally, other suitable methods for generating salts are specified throughout this specification, and are within the scope of the present definition. It is believed that, 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 and vegetables "and also refers to other foods" such as grains and dairy products. In the preferred embodiments, the food items referred to herein are those that are perishable or prone to damage when exposed to microbes or other pathogens. Additionally, a "consumable" product is intended to refer to food items, fluids to drink, ingestion medicines or any other product introduced internally by any means, in a human or animal. As used herein, the term "antimicrobial" is used in its general sense to refer to the propensity of the described compound, product, composition or article to prevent or reduce the development »spreading» formation or other subsistence organisms such as bacteria »viruses» protozoa »molds or other organisms that could cause damage 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 medical patients (human or animal), medical care products, 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 the class of polyols containing at least two hydroxyls which are separated by at least three intermediate atoms. It has been found that these compounds stabilize the organosilines of the invention by preventing self-condensation or other inactivation of the resulting compounds and products. As used herein, the terms "polyol" and "stabilizer" are used interchangeably to describe a molecule having at least two hydroxys separated by no more than two atoms. Finally, the terms "halogen" are used to refer to the fluorine "F" »chlorine" Cl ", bromine" Br ", iodine" I "and astatin" At ". Preferably, halogen or halide refers to F, Cl or Br. The term "halide" is intended to include those halogens. Taking these definitions into account, the present invention provides the product formed by the mixture of an organosilane of the formula R "SiX ^ _" "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, independently, is a drillable group; with a polyol containing at least two hydroxyls that are separated by less than three intermediate atoms (i.e., irrespective of the number of hydroxy groups present in the compound, there are at least two that are separated by less than three intermediate atoms). It is more preferred, in the above product, that n is an integer from 0 to 2, preferably i; that each R. independently "is alkyl" preferably of 1 to 22 carbon atoms "branched or unbranched" substituted or unsubstituted; better yet »from 1 to 6 carbon atoms or from 10 to 20 carbon atoms; especially from 1 to 4 carbon atoms or from 14 to 18 carbon atoms »alkyl alcohol with similar chain lengths, branching and substitution; or aromatic »such as benzyl» phenyl. etc.; each X »independently» is hydroxy »alkoxy, halogen (such as, but not limited to: Cl, Br, I or F); acetyl. acetoxy »acyl» a solid or liquid polymeric »hydroxylated portion; polyether or polyalkylether; and the polyol is an alcohol having at least two hydroxyl »one carbohydrate» which includes a monosaccharide. a disaccharide »an olosaccharide» a polysaccharide; a modified carbohydrate that includes graft or block copolymers; a partially alkylated carbohydrate »acylated or acetylated; a product of carbohydrate oxidation (for example: glucuronic acid, mucic acid); reduced carbohydrates »substituted carbohydrate or substituted carbohydrate polymers (for example: nucleosides, nucleotides, nucleic acids). In one embodiment »the polyol is a single monosaccharide» such as: glucose »fucose» fructose. In another modality »polio! it is an oligoeric sugar (for example »a dimer» such as sucrose, a trimer »a tetramer» etc.). In another modality, polyphenol is annitol, ascorbic acid, glyoxal, or a single substance. When using ascorbic acid or a similar compound as a polyol, it is often convenient to include an antioxidant in the composition to prevent the oxidation of ascorbic acid. In another embodiment, the polyol is an oxidized sugar, such as glucuronic acid. In another modality »the pol o! is a polymeric carbohydrate »such as cellulose» partially hydrolyzed cellulose, partially hydrolyzed cellulose acetate, starch, soluble starch »a suitable graft copolymer-acrylic acid. As a source of some of these polyols, the cost-effective carbohydrate and even complex carbohydrate compositions include corn syrup, honey and similar compositions. In order to control the development of bacteria, these compositions may optionally include a preservative, such as benzoic acid, which is acceptable for human applications, and which provides an antibacterial function. This is particularly important when the organosilane to be stabilized does not itself have anti-microbial activity. and it is much less important when the organosilane itself is antibacterial. In another embodiment of the present invention, the invention provides the product described above, wherein the organosilane has the formula II, III, IV or V:
(Ra.) SiRssN * (R3) (R ^) (Rβ) Y- (II) (R 3SiRseN (R 3) (R ^) (III) (Ra.) 3 SiRi? R3ß (IV) (Ra.) SESi (R3ß) (R3 ^) (V) wherein each independently is halogen or Rβ0"wherein R? Is H, alkyl of 1 to about 22 carbon atoms, acetyl, acetoxy, acyl, propylene glycol, etilengl col? polyethylene glycol »polypropylene» block and copolymers of ethylene and propylene glycol »the monoether alkyl of 1 to 22 carbon atoms of propylene glycol, and polyethylene glycol, polyethylene glycol, block and copolymers of ethylene and propylene glycol or the monoester of a carbonic acid of 22 carbon atoms and propylene glycol, et alol col, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, octylphenol, nonylphenol, and sorbitan ethers, R3ß is H, halogen (such as Cl, Br »F or I), NHa (CHa) aNHRa, NHaRa» C3Hβ0aRa, C ^ Hβ0aRa, NaO (CH30) P (0) Ra »O, independently, are halogen» H »alkyl from 1 to about 8 carbon atoms. carbon »preferably from 1 to 4 carbon atoms» better still »from 1 to 2 carbon atoms» isobutyl »phenyl or n-octyl; R-. is benzyl »vinyl or alkyl of about 3 carbon atoms; R..sy R ^ "independently" are lower alkyl alcohol of 1 to 4 carbon atoms, lower alkyl of 1 to 4 carbon atoms, alkyl of about 22 carbon atoms, preferably 1 to about 10 carbon atoms. carbon atoms »better still» alkyl of 1 to 4 carbon atoms »or even better» of 1 to 2 carbon atoms »or Ra and R ^,. together »can form a morphine or a cyclic or" unsaturated or saturated "heterocyclic ring of five to seven members of the formula Vi:
(R) K-R ^ - (VI) wherein K is an integer from 0 to 2 »preferably O to l» very preferable »i; R ^. when the anchor is saturated »is CHa. 0, S, NH, NHa - * -, NCHaCHaNHa, CHaCH3sNH3? -, NCHaCHaN (Rβ) (R "), NCHaCHaN * (Rβ) (Rβ) (R3.0), N (alkyl), N (aryl) , N (benci lo); wherein each of Rm, ,, and RO 'independently, is benzyl, polyether, lower alkyl alcohol of 1 to 4 carbon atoms »lower alkoxy of 1 to 4 carbon atoms, or alkyl of about 22 carbon atoms; preferably 1 to about 10 carbon atoms; and the "alkyl" specified above is 1 to 22 carbon atoms, better still, 1 to 10 carbon atoms and, most preferred, 1 to 3 carbon atoms; it is more preferred that the "ar lo" be phenyl benzyl; and R7, when the ring is unsaturated, is: CH, N »N + H, N + (alkyl?» N + l) »N + (benzyl?)» N-CHaH \ l »N ~ H- CHa-N »N- (alkyl0) -CHa-N, N ~ (arylO> -CHa-N. N * - (benzyl) -CHa-N. Wherein the alkyl, the aryl or the benzyl are as described above, wherein the ring is unsubstituted or substituted with alkyl of 1 to 22 carbon atoms, better yet »of 1 to 10 carbon atoms» and most preferred »of 1 to 3 carbon atoms; »Aldehyde» carboxylate (preferably acetox, acetyl »acyl or per luorocarboxylate)» amide »thione ida» nitro »amine or halide» very preferred Cl. Br or I. R "is lower alkyl alcohol, preferably from 1 to 6 atoms of carbon, better yet »of 1 to 4 carbon atoms» CHaCßHB »polyether, such as a polyethylene glycol or a polypropylene glycol» alkyl of 1 to 22 carbon atoms, better still, of 1 to 10 carbon atoms, very preferable from 1 to 6 carbon atoms »alkoxy, from 1 to 22 ca rbono, better yet, from 1 to 10 carbon atoms, very preferably from 1 to 6 carbon atoms; perfluoroalnyl of 1 to 22 carbon atoms, better still, of 1 to 10 carbon atoms9 and most preferred, of 1 to 6 carbon atoms; perfluoroalkyl Isulfonate, from 1 to 22 carbon atoms, better still, from 1 to 10 carbon atoms, and most preferred, from 1 to 6 carbon atoms; or perfluoroalkyl Icarboxylate, or is a ring of five to seven members, of formula VI, as described above; and Y- is an anionic portion suitable for forming the salt of the compound of the formula II, III, IV or V. The invention provides a stable composition in water »comprising water and the organo or» mixed with the polio !. further, the present invention also provides a composition for treating a substrate, comprising a carrier and an effective amount of an organosilane and a polyol, as described herein. In an alternative embodiment, the present invention provides a composition for treating a substrate comprising a carrier and an effective amount of the compound as described above. In other modalities »the carrier is different from water. In yet another modality, the organoleno is: 3- (trimethoxysilyl) propi chloride Idimeti 1-octadecylammonium »3-trimethoxysi-1-yl) propylmethyl-di (decyl) ammonium chloride» 3-chloropropyltrimethoxysilane »octadecyltrimethoxysilane or perfluorooctyl trietoxisi tin, and the polyol is an alcohol having at least two hydroxyl »carbohydrates, including monosaccharides, disaccharides, olosaccharides, pol saccharides, modified carbohydrates, including graft and block copolymers, partially alkylated carbohydrates, etc. sides or acet sides »the carbohydrate oxidation products (eg» glucuronic acid »uic acid)» reduced carbohydrates and substituted carbohydrates (eg »nucleosides, nucleotides» nucleic acids). In another modality more »the organosilane is:
Furthermore, in another additional embodiment, the organosilane is NHae (CHsa) aNH (CHa> 3Si (OCH3) 3, NHa (CHa) aS1 (0CH3) 3, NHa. (CHae) 3-Si (0CHaCH3) 3, Cl ( CHa5) 3 Si (OCH 3) 3, Cl (CHa) 3 Si (0CHaCH 3) 3 Cl (CHa) 3 SiC13 »C 3 H 3 O (CHa) 3 Si (0CH 3) 3» C 3 H 3 O (CHa) 3 Si (0CHaCH 3) 3 »C-» Hβ, 0a (CHa!) 3S (0CH3 3, 0 ^ 0 ^ (CH ^^ Si (OCHaCH3) 3, CH3SiHCla, NaO (CH30) P (0) (CHa) 3Si (OH) 3, SiHCl3, n-2 hydrochloride vinyl-benz 1 amino-eti 1-3-ami nopropi 1 tr metoxisi 1 ano, HaC = CHSi (0C0CH3) 3, HaC = CHS (0CHa) 3, HaC = CHSi (0CHaCH3) 3, HaC = CHSiCl3. (CH3) aSiCa, (CH3) aS 0CH3) a. (CßHß) aSiCla. (CaHß) SiCl3, (CaHß S? (0CH3 > 3, (CaHs) S (0CHaCH3 3 »isobut ltrimethoxy lano» n-octi 1 tri ethoxy if the o »CH3 (C" Hß) SiCla »CH3SiCl3» CH3Si (0CH3) 3. CßHsS Cl3, CßHBS (0CH3) 3 »C3H-, S Cl3» C3H ^ Si 0CH) 3 »SiCl ^» ClCHaC < BH ^ CHaCHaS Cl3r ,, ClC a¡CHC sl¡C ¡Si- (0CH3) 3, ClCHaCßH ^ CHaCHaSi (0CHaCH3) 3, deci 1 trichlorosi lano, dichloromet l (4- eti lfenetil) si láño, diettox etilfen is lano , C3- (diethylamine) propi 1-trimethoxysilane, 3- (d-methoxymethyl-1) -1-propanotol, di-ethoxyet 1 vin Isi lano, 3-Ctris methacrylate (trimethylsilyloxy) -s? li 13propyl, trichloroC4-
(chloromethyl) phen l 3-silane, meti lb s tr meti Is 1 lo i vin l-silano, raet lpropox si láño, or triclorociclopenti Isi lño. In addition, the present invention also provides a product from mixing an organosilane of formula II, III, IV or V: (Ra.) SiRaN * (R3) (R ^) (Rβ) and- (II) (Ra. ) SiRaN (R3XR- »(III) (RA) 3SiRaR3ßl (IV) (Ra.) ASi (3 &s) (R3-7> &Vt; V > as described substantially further back, with reference to numbers of formula II »III, IV and V, with alcohols having at least two hydroxyls, carbohydrates, including monosaccharides, disaccharides, olosaccharides, polysaccharides, modified carbohydrates, including graft and block copolymers, partially alkylated, acylated or acetylated carbohydrates sides »products of carbohydrate oxidation (eg, glucuronic acid, mucic acid), reduced carbohydrates and substituted carbohydrates (eg» nucleosides »nucleotides, nucleic acids) In addition, the present invention also provides a method for treating a substrate, which comprises contacting the substrate with a quantity Sufficient composition of the composition described above, for a sufficient period of time for the treatment of! substrate Furthermore, 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. The present invention also provides a treated substrate having adhered to it the product produced by contacting the organosilane and the polyol, as described above. Alternatively, the present invention provides a treated substrate having adhered thereto a compound produced by contacting the organosilane and the polio as described above. In yet another embodiment, the present invention provides a method for dyeing and treating a substrate comprising contacting the substrate with an aqueous (ie, substantially water-soluble) composition comprising a soluble aqueous dye suitable for dyeing a substrate. and the product formed by mixing an organosilane of the formula R "SiX, _", wherein n is an integer from 0 to 3 », preferably 0 to 2; each R »independently» is a non-hydrolysable organic group; and each X »independently, is a hydrolysable group; with a polyol containing at least two hydroxy groups, wherein at least two of said groups are separated by less than three intermediate atoms "for a period of time sufficient to dye and treat the substrate. In yet another preferred embodiment, the present invention provides a method for treating a food article "anti-croissant" comprising contacting the article with an effective amount of the product formed from mixing an organosilane of the formula R ^ Si ^, " where n is an integer from 0 to 3 »preferably 0 to 2; each R »independently» is a non-hydrolysable organic group; and each X "independently" is a hydrolysable group; with a polyol containing at least two hydroxy groups "wherein at least two of said groups are separated by less than three intermediate atoms" for a period of time sufficient to treat the food article antimicrobially. In yet another embodiment, the present invention provides a method for antimicrobially coating a container for fluid, used to contain a product consumable by humans or animals, which comprises contacting the container with a liquid. container with an effective amount of the product formed by mixing an organosilane of the formula R ^ SiX ^. ^ "where n is an integer from 0 to 3", preferably 0 to 2; each R "depends entirely, is a non-hydrolysable organic group; and each X, independently, is a hydrolysable group; with a polyol containing at least two hydroxy groups "wherein at least two of said groups are separated by less than three intermediate atoms, for a period of time sufficient to antimicrobially coat the container. Additionally, in still another embodiment, the present invention provides a method for antimicrobially coating a medical latex article, for use in a human or animal medical procedure, comprising contacting the article with an effective amount of the product formed from mixing an organosilane. of the formula RnSiX. * _ "» where n is an integer from 0 to 3, preferably 0 to 2; each R, independently, is a non-hydrolysable organic group; and each X »independently, is a hydrolysable group; with a polyol containing at least two hydro? i groups, wherein at least two of said groups are separated by less than three intermediate atoms, for a period of time sufficient to antimicrobially coat the article. In another embodiment of this method, the article is a surgical glove. In a further embodiment, the present invention provides a method for antimicrobially treating a substrate selected from the group consisting of a concrete tube, a toothbrush, a comb, a hairbrush, a denture, an orthodontic retainer, a water tank or pool filter »an air filter» an HVAC air system »a cabin air system» an article of marble »a statue» an exposed piece of art »an HDP plastic cover» a fiber article made of glass coated with slone or with TEFLON *** »» a Dryvitt finish »a stucco finish» a cotton mix »a bio-film» a bio-adhesive »a single-water roof» pebbles for roofing and a fiberglass reinforcing product; which comprises contacting the substrate with an effective amount of the product formed by mixing an antimicrobial organosilane of the formula RoSiX., "where n is an integer from 0 to 3" preferably 0 to 2"each R" dependently "is a non-hydrolysable organic group; and each X "independently" is a hydrolysable group; with a polyol containing at least two hydroxy groups »where a! less two of said groups are separated by less than three intermediate atoms, for a period of time sufficient to treat antimicrobial among the article. Also, in another modality more. The present invention provides a method for antimicrobially improving a rubbing alcohol product, a flower preservative or an imperceptibility solution, comprising mixing with the product an effective amount of the product formed from mixing an organosilane of the formula R ^ SX ^ . ,,, where n is an integer from 0 to 3. preferably 0 to 2 »each R, independently, is a non-hydrolysable organic group; and each X "independently" is a hydrolysable group; with a polio! containing at least two hydroxy groups "wherein at least two of said groups are separated by less than three intermediate atoms, for a period of time sufficient to antimicrobially improve the product. The present invention provides compounds »stabilized and / or water-soluble organosilane compositions and products» methods for their use and articles prepared using the compounds »products and compositions. In particular, the present invention is useful for stabilizing a large variety of organosilanes of the general formula wherein Si is an integer from 0 to 3, preferably 0 to 2.; each R »independently» is a non-hydrolysable organic group; and each X "independently" is a hydrolysable group "such as" but not limited thereto: organofunctional "aromatic" alkyl or a combination thereof; and X is halogen, such as but not limited to: Cl »Br or i; or X is hydroxy »alkoxy» such as methoxy or eto ?? »acetoxy or unsubstituted or substituted acyl. For these organosilanes, X is prone to react with various hydroxyl-containing molecules. In yet another embodiment, the present invention employs about O.OO.sub.li to 20% by weight of an organosilane containing hydrolyzable groups and about 0.01 to 20.0 equivalents by weight, preferably about 0.1 to 5 equivalents by weight, of a stabilizer. of polyol of the invention. This preparation is preferable for water soluble stabilizers, such as glucose, sucrose, glucuronic acid, nucleosides, nucleotides, polynucleotides. Alternatively, when the stabilizers are not sufficiently soluble in water, additional stability is achieved by mixing the organosilane with the stabilizer in a non-aqueous solvent. In said alternative preparation the remaining solvent (eg methane!) Is released by distillation, freeze drying, evaporation or other methods known in the art to remove volatile organic solvents. For the polyols within this invention, which in themselves are not very soluble in water, an organosilane stabilizing effect can still be achieved by mixing the organosilane, for example, with a carbohydrate in water, followed by filtration. In such a manner »the filtrate can be stabilized while still exhibiting a desirable property» such as the antimicrobial activity. When organosilane is not an antimicrobial agent, spectral evidence of the presence of the compound to demonstrate the presence of the compound is useful. These methods provide clear »stable» solutions of the organosol »which are capable of coating surfaces with organosilane» by treating the surface with the solution. The solutions are stable for prolonged periods, from several days to several months. It will also be recognized that. although it is possible to stabilize aqueous siloxane master solutions up to 20% siloxane, by means of the polyols described herein, the working concentrations of! siloxane tend to be on the 0.001-5% siloxane scale »where the effects of the stabilization of the stabilizers described here are less challenged by the higher siloxane concentrations» required for the master solutions. 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. Whoever is an ordinary expert in the field will recognize that the previous preparation steps are mere lines and said person, without undue experimentation, would be able to prepare the composition by varying the parameters for the contact or mixing of the organosilane and the polyol, and in order of introducing the reagents and starting materials without deviating from the basic and novel features of the present invention.
LOS SILANOS
The present invention is useful for stabilizing organosilanes of the general formula R ^ SiX ^^. ^, "Where n is an integer of O to 3", preferably O to 2; R is a non-hydrolysable organic group (aromatic alkyl, organofunctional or a combination thereof); and X is hydroxy, alcoho, preferably methoxy or ethoxy. halogen, preferably Cl »Br or I; acetoxy, acyl or substituted acyl, or a hydrolysable polymer or other portion, prone to hydrolysis and / or environmentally safe. The organosilanes used in the practice of the present invention do not need to be water soluble, and often they 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. Numerous organosilanes known in the art are suitable for the present "stabilization processes" to produce compounds, products and compositions stabilized in water. U.S. Pat. Nos. 4, 511, 585, 5, 064, 613, 5,145,592, and the publication entitled "A Qu de a DC si lañe Coupling Agent" (Dow Corning, 1990) describe many suitable organosilanes. The contents of these references are hereby incorporated in their entirety herein by reference to the teachings of suitable organosilanes. These organosilanes are suitable for the formation of the compounds, "water-stable organosilane products and compositions of the present invention." Additionally, the description of US Pat. No. 4,390,712 is incorporated by reference to its teachings. of the synthesis of siloxane in an aqueous medium According to the present disclosure, those skilled in the art will appreciate that the methods of aqueous synthesis of loxane of the 4,390,712 patent are advantageously modified upon effecting the synthesis of loxane in the presence of the polyol stabilizer as defined herein thereby forming a stabilized anole-water silo composition, while still exploiting the accelerated kinetics of siloxane formation in aqueous media, noted in the '4,390 patent. 712. Accordingly »another embodiment of this invention consists of a method for forming an organosilane of the formula R" SiX - ^ _ ", where n is an integer from 0 to 3», preferably 0 to 2; each R. independently "is a non-hydrolysable organic group; and each X. independently "is a hydrolysable group» from starting materials »in an aqueous solution» in the presence of a polyol containing at least two hydroxyls that are separated by less than three intermediate atoms »in an effective amount of polyol »sufficient to stabilize the organosilane as it is formed from the reactants. Preferred silanes, for use in the compounds, products and compositions and in the methods of the present invention "include the silanes of the following formula:
(Ra.) 3SiRaN * (R3) (R -.) (Rß) Y- Ó (RA) 3SiRaN ~ CßHßY-where each Rx, depending »is halogen CC1» Br »I» FU or R? 0 »on where Rβ is H "alkyl of about 6 carbon atoms" unsubstituted or substituted "preferably from 1 to about 2 carbon atoms and. better yet »1 carbon atom; or acetyl or other acyl "including substituted acyl; or Rβ0 can be derived from any hydroxylated polymer »hydrogenated liquid, hydroxylated solid» irrespective of the solubility in water; or R <0> may be derived from any polyether, such as, but not limited to: polyethylene glycols or polypropylene glycols, such as polypropylene glycol triol (glycerol propoxate); R. "is unsubstituted or substituted benzyl" or an unsubstituted or substituted alkyl "of about 3 carbon atoms, preferably alkyl of 1 to 22 carbon atoms; R. ,, and R ^. independently "are lower alkoxy of 1 to 4 carbon atoms" preferably of 2 carbon atoms "such as CHaCHaOH» CHaCH (OH) CH3 »alkyl of 1 to about 22 carbon atoms» preferably from 1 to about 10 carbon atoms »and better yet» of 1 to 2 carbon atoms; or Ra and R ^. together »can form a morpholine or other" unsaturated or saturated "cyclic or heterocyclic ring of five to seven members, of the formula: -R3- (R ^ KR ^ - (VI) where k is an integer from 0 to 2; When the ring is saturated, it is CHa, 0, S, NH, NHa "* -, NCHaCHaNHa, NCHaCHaNHa *, NCHaCHaN (Ra) (R), NCHaCHaN- (Rm) (R) (R o), NO (alkyl), N (aryl), N (en), and 7, when the ring is unsaturated, is: CH, N, N + H, N + (alkyl), N + (ary!), N + (ency lo ), N-CHa-N, N * H-CHa-N, N * (alkyl) -CHa-N, N * (ari 1 o) -CHa-N. «V * - < benci lo) -CHa- N, where Ra, Rβ, and Ra.0 »independently, is benzyl, polyether, lower alkyl alcohol of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, or alkyl of 1 to about 22 atoms carbon, preferably 1 to about 10 carbon atoms, Rs is CH-jC ^ Hβ »CHaCHaH» CHaCH (0H) CH3, a polyether, such as polyethylene glycol: - (CHaCHa0) ßH, polypropylene glycol: - ( CHaCH (CH3) 0) 3H, or alkylated poly oxyethylene: - (CHaCHa0) ßB "wherein B is alkyl of 1 to 22 carbon atoms" unsubstituted or substituted "and wherein each" a ", independently" is an integer from 1 to 12, better yet, around i to 5; or Rβ is alkyl or perfluoroalkyl of 1 to about 22 carbon atoms, preferably about 12 to 20 carbon atoms, and still better still about 14 to 18 carbon atoms; and Y is halogen (such as Cl »Br» I »acetate» sulfate »tosylate or carboxylate» such as the acetate, polycarboxylate, functionalized carboxylate salts, such as trifluoroacetate and perloalkylcarboxylates, or other alkyl salts. and isulfonate, including the trifluoromethylsulfonate and per-chloroalkyl sulfonate salts, the phosphate and phosphonate salts, the borate and boronate salts, or any other suitable anionic moiety Preferred organosilanes include, but are not limited to: 3- (trime. toxylyl) propyldimethyloctadecylammonium chloride 3- (trimethoxysilyl) propylmethyldi. {decile) ammonium chloride, 3-clo rop ropi 1 rimethoxysilane, octadecyl rime oxysilicon, perfluarosctilium oxysilumone,
(CH3O) 3Si (CH2) 3N + (CH3) 2C18H37Cr, (CH3O) 3Si (CH2) 3N + (CH3) 2 ClgH37Br, (CH3O) 3Si (CH2) 3N + (C10H21) 2CH3Cl-, (CH3O) 3Si (CH2) 3N + (C10H21 ) 2CH3Br-, (CH3O) 3Si (CH2) 3N + (CH3) 3Cl-, (CH3O) 3Si (CH2) 3N + (CH3) 2CgH17Cl-, (CH3O) 3Si (CH2) 3N + (CH3) 2C10H21Cl-, (CH3O) 3Si (CH2) 3N + (CH3) 2C12H25Cl-, (CH3O) 3Si (CH2) 3N + (CH3) 2CHH29Cl-,
(CH3O) 3Si (CH2) 3N + (CH3) 2C16H33Cl-, (CH3O) 3Si (CH2) 3N + (CH3) 2C20H41Cr, (CH30) 3Si (CH2) 3N + (C4H9) 3Cl-, (CH3O) 3Si (CH2) 3N + ( C2H5) 3Cl-, (CH3CH20) 3Si (CH2) 3N + (CH3) 2C18H27Cl-, (CH30) 3Si (CH2) 3NHC (0) (CF2) 6CF3, (CH3O) 3Si (CH2) 3NHC (0) (CF2) sCF3 , (CH3O) 3Si (CH2) 3NHC (O) (CF2) 10CF3, (CH3O) 3Si (CH2) 3NHC (O) (CF2) I2CF3, (CH3O) 3Si (CH2) 3NHC (0) (CF2) 14CF3, ( CH3O) 3Si (CH2) 3NHC (O) (CF2) 16CF3, (CH30) 3Si (CH2) 3NHS02 (CF2) 7CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 6CH3,
(CH3?) 3 Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 8CH3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O) (CH2) 10CH3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 12CH3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 14CH3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) I6CH3,
(CH3?) 3 Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 6CF3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O) (CF2) 8CF3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 1oCF3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) I2CF3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 14CF3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 16CF3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 7CF3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 9CF3,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) uCF3,
(CHAOaS C? JaN + ÍCHaWCH ^ aNHSOjCCFJuCFj,
(CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 15CF3, (CH30) 3S CHa) 3N * (Ca) a (CHa) 3NHS0a (CFa) ßCF3. am noetilam nopropi! tri ethoxy lano: NHa (CH2) al \ iH (CHa) 3Si-
(0CH3) 3, 3-aminopropyl-1-trimethoxysilane: (OCH3) 3 »3-aminopropyltriethoxysine: NH (CHa) 3Si (OCHaCH3) a» 3-chloropropyl-1-rimethoxysilane: C! (CHa) 3Si (OCH3) 3. 3-Chloropropy Itriethoxysilane: Cl (CHa) 3S (OCHaCH3) 3 »3-chloropropyl 1 trie! orosi laño: Cl (CHa) 3Si! 3 »3-glycoidoxipropi 1 trimetoxisi o: C a? s¡, (CHs¡ '.}. S? (OCH3) 3» 3-gl icidoxipropi Itrietoxisiño: C3HßOa (CHa ) 3S (0CHaCH3) 3. 3-methacryloxypropyl tr methoxylamino: C ^ HßOa (CHa) 3 Si (0CH3) 3 »
3-methacryloxypi 1 triethoxysi 1 ano: C ^ HßOa (CHa) 3Si (0CHaCH3) 3 »methyldichlorosilane: CH3SiHCla» melamine modified with silane: Dow Corning Ql-6106, (trihydroisyl) propi Imet Ifos sodium onate : NaO (CH30) P (0)
(CHa) aSi (0H) 3, trie! Orosi laño, SiHCl3, n-2-vini hydrochloride Ibenci lamino-ethyl-3-aminopropi Itrimetoxisi o: Dow Corning Z-6032, vinyltriacetoxysilane: HaC = CHSi (0C0CH3 ) a, vini 1 trimetoxisi o: HaC = CHS (0CH3) 3 »nor 1trietoxisi 1ano: HaC = € HSi (0ChaCH3) 3» vinyltriclorosi laño: HaC = CHSiCl3, dimeti 1dic1orosi 1ano: (CH3) aSiC1a »dimethyldimethoxysilane: (CH3 ) aSi (OCH3) a »difen 1 dic1 orosi 1ano: (C-Hß) -SiCl" »e 1 tr c1orosi 1 ano: (CaHß) S Cl3» ethyl trimethoxysi lano: (CaHß) Si (0CH3) 3. Eti I ethoxy silane: (CaHB) Si (OCHaCH3) 3 »isobuty 1 r methoxysyno» n-octytrietoxisi or »methyltrichlorosilane: CH3SÍCI3» metí 1tri ethoxisi o o: CHaS (0CH3) 3, phenyltrichlorosi lano: CBHBSiCl3 » fen ltr ethox the o: CßHBS (OCH3) 3 »n-propyl trichlorosi lano: C3H ^ SiCla» n-propyltrimeto? isi laño: C3H ^ Si (0CH3) a. Silicon tetrachloride: SiCl ,, C! CHaC - CHaCHaSiCl3 ,, Cl CHaCßH ^ CHaCHaS i (OCHa) 3, Cl CHaCß * CHaCHaS i (OCHaCH3) 3, decyl trie! orosi tin »dichloromet l (4-methyl-phenethyl) si tin »dietoxy eti Ifeni Isi laño» C3- (diethylamino) propyl il-trimethoxysi lano »3- (dimethoxymethyl isyl) -l-propanothiol» dimethoxymethi 1 viny! if o. 3-L * tris- (trimethyl isyl i loxi) sil il üpropi locrylocite- (Chloromethyl) fen l 3s lino »met Ib s (Trimeti Isil i loxi) vin Isi lano» meti Itr propoxisi la o » and trichlorocyclopenti Isi la o.
In a particular embodiment of this invention, that is to say, the use of organosilane as a UV protector, for example, in a sun tan lotion, the para-a-benzoic acid is. an active component In accordance with this embodiment of the invention, the organosilane is selected from:
(CH3O) 3Si (CH2) 3NHC6H4COOH (CH30) 3Si (CH2) 3NHC6H4COOCH3 (CH30) 3Si (CH2) 3NHC6H4COOC2H5
(CH30) 3Si (CH2) 3NHC6H4COOC3H7 (CH30) 3Si (CH2) 3NHC6H4COOC4H9 (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H5 (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4NH2 (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4N (CH3) 2 (CH30) 3Si (CH2) ) 3NHC6H4COOCH2C6H4N (CH2CH3) 2 (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH3) 3 Y "(CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH2CH3) 3 Y- (CH30) 3Si (CH2) 3NCH3C6H4COOH (CH30) 3Si (CH2) 3NCH3C6H4COOCH3 (CH3?) 3Si (CH2) 3NCH3C6H4COOC2H5 (CH30) 3Si (CH2) 3NCH3C6H4COOC3H7 (CH30) 3Si (CH2) 3NCH3C6H4COOC4H9 (CH30) 3Si (CH2) 3NCH3C6H4COOCH2C6H5 (CH30) 3Si (CH2) 3NCH3C6H4COOCH2C6H4NH2 (CH30) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N ( CH3) 2 (CH30) 3 Si (CH2) 3NCH3C6H4COOCH2C6H4N (CH2CH3) 2
(CH3?) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH3) 3 Y- (CH3?) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH2CH3) 3 Y- (CH3?) 3Si (CH2) 3N + (CH3) 2C6H4COOH Y "(CH30) 3SI ( CH2) 3N + (CH3) 2C6H4COOCH3 Y- (CH30) 3SI (CH2) 3N + (CH3) 2C6H4COOC2HJ Y- (CH30) 3SI (CH2) 3N + (CH3) 2C6H4COOC3H7Y- (CH30) 3SI (CH2) 3N + (CH3) 2C6H4COOC4H9 Y- (CH30) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6Hs Y- (CH30) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4NH2? - (CH30) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH3) 2 Y- (CH30) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y- (CH3?) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N + (CH3) 3 Y? -
(CH3CH20) 3Si (CH2) 3NHC6H4COOCH2C6H4NH2 (CH3CH20) 3Si (CH2) 3NHC6H4COOCH2C6H4N (CH3) 2 (CH3CH20) 3Si (CH2) 3NHC6H4COOCH2C6H4N (CH2CH3) 2 (CH3CH20) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH3) 3 Y '(CH3CH20) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH2CH3) 3 Y "
(CH3CH2?) 3Si (CH2) 3NCH3C6H4COOH (CH3CH2O) 3Si (CH2) 3NCH3C6H4COOCH3 (CH3CH2O) 3Si (CH2) 3NCH3C6H4COOC2H5 (CH3CH2O) 3Si (CH2) 3NCH3C6H4COOC3H7 (CH3CH2O) 3Si (CH2) 3NCH3C6H4COOC4H9 (CH3CH20) 3 Si (CH2) 3NCH3C6H4COOCH2C6H5 ( CH3CH20) 3Si (CH2) 3NCH3C6H4COOCH2C6H4NH2 (CH3CH20) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N (CH3) 2 (CH3CH20) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N (CH2CH3) 2 (CH3CH2O) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH3) 3 Y- (CH3CH2O) 3Si ( CH2) 3NCH3C6H4COOCH2C6H4N + (CH2CH3) 3 Y "
(CH3CH20) 3Si (CH2) 3N + (CH3) 2C6H4COOH Y- (CH3CH20) 3Si (CH2) 3N + (CH3) 2C6H4COOCH3 Y "(CH3CH20) 3Si (CH2) 3N + (CH3) 2C6H4COOC2H5 Y" (CH3CH2O) 3Si (CH2) 3N + (CH3) 2C6H4COOC3H7 Y- (CH3CH20) 3Si (CH2) 3N + (CH3) 2C6H4COOC4H9 Y- (CH3CH2O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6Hs Y "(CH3CH2O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4NH2 Y- (CH3CH2O ) 3 Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH3) 2 Y- (CH3CH2O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y- (CH3CH2O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N + (CH3) 3 Y? - (CH3CH2O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N + (CH2CH3) 3 Y? - (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOH (CH3CH2O) 3Si (CH2) 3NC2H5C6H4COOCH3
THE STABILIZERS
As described herein, the preferred binders of the present invention contain at least two hydroxy groups, wherein at least two of said at least two hydroxy groups are separated by less than three intermediate atoms, i.e. (HO-AB-HO), where A and B are any of one or two atoms). Said stabilizers can establish the aqueous solutions of the organosilanes described above and are generally useful for the stabilization of all solutions when n is an integer from 0 to 2, and when water solubility or minimization is desired. or the prevention of water-induced self-condensation / and associated polymerization). In particular, the preferred stabilizers are monosaccharides, including, but not limited to: glucose; disaccharides, including, but not limited to, sucrose; polysaccharides, polynucleotides and alcohols; wherein at least two adjacent hydroxyls, separated by less than three intermediate atoms, are present in the stabilizer.
THE USES
The compounds, products and compositions of the present invention are useful for a multitude of purposes. These purposes include any known use for the organosilanes »preferred starting material» of the general formula described above. In the preferred embodiments, the water-stabilized organosilane compounds, products and compositions are suitable for applications such as: 1) the treatment of surfaces, including fillers and pigments; 2) Ad ives for coatings, such as dyes; or 3) as additives for organic monomers (such as acrylics) before the formation of the respective polymer. Therefore, in addition to the usefulness of the organosilane-quaternary ammonium compounds such as 3- (trimethoxysi-1-yl) propyl-dimethylammonium chloride as anti-microbial agents that bind to a surface, other numerous uses of organofunctional silanes »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 inks adhesives »and as reactive intermediates for the synthesis of silicone resin. The present invention can be used to prepare, inter alia, agricultural products, cleaning compositions, antimicrobial sponges, anti-microbial bleaching agents, antimicrobial fillers for paints, plastics or concrete, and for treating concrete structures, such as livestock rests, in where microbial infestation is a problem. In various embodiments, the surfaces and substrates which are treatable with the compounds, products and compositions of the solution of the invention include but are not limited to: textiles, carpets, shades, upholstery, fabrics, sponges, plastics, metals, surgical bandages, masonry materials, silica »sand» alumina, aluminum hydrochloride, titanium dioxide, calcium carbonate »wood, glass beads, containers, tiles, floors. curtains, marine products, tents, backpacks, roofing materials, wall linings, fences, moldings, insulation, wall boards, garbage receptacles, outdoor devices, water and land purification systems. In addition, articles treatable with the compounds, products and compositions of the invention include, but are not limited to: air filters and materials used for their manufacture; filters for aquarium, cushions cushions, fiber filling for upholstery, fiberglass duct panels, underwear and weatherproof clothing, polyurethane foam and polyethylene foam »sandbags, tarpaulins» sea sails »ropes» shoes »hosiery »Towels» disposable swabs »socks and underwear» cosmetics »lotions, creams» ointments, disinfectant hygienists, preservatives for wood, plastics, adhesives »paints» pulp »paper» cooling water and adi i os for laundry and surfaces that do not they are in contact or that they are in contact, with food, in general. For the substrates, mixtures and applications described above, the treatment generally involves contacting or mixing the article to be treated with a water-stabilized organosilane solution of the present invention, which comprises the compound derived from lano-stabilizing organs 1 in an aqueous solution, for a sufficient time for the active organosilane ingredient (or a portion thereof) to remain attached to the article. In general, the treatment starts almost immediately when it comes in contact; but preferably it requires around 15 seconds to about 48 hours; better yet »around 1 minute to 24 hours; even better »around 5 minutes to 1 hour; and very preferable »around 3? minutes The additional general guidelines for the application are as follows: For immersion of a large object, it is preferred to allow 1 to 2 minutes of immersion in the solution and then allow the object to dry. However, some objects will benefit from very short mixing or contact times, for example, the fabric can pass through an aqueous bath of the composition at a speed of up to 36.5 m per minute or more. After immersion »the excess solution can be gently cleaned or rinsed. Alternatively, the solution can be sprayed on the substrate. further, the composition of the invention can be placed in a high intensity solid mixer, and a powder can be formed, which is then dried. The dry powder can then be used in a spray, if desired. Additionally, solutions can be applied by rubbing on the substrate and applied using sponges or fabrics, etc. In addition, the solutions of the present invention can be added to pigments and fillers and stirred with them for several (2-3) minutes. Additional »solutions can be added to an emulsion or another existing formulation» before use. Solutions can also be added in addition to »with or as a spray coolant for extruded fibers. However, one of ordinary skill in the art will recognize that numerous other uses and modes of application for compounds, products and stable organo compositions of the present invention are readily apparent.; and without undue experimentation, they will be able to determine effective methods of application and effective treatment times for any substrate »particular article or other application. In addition, the compositions can be used in the foulard processes that are known in the text systems. Further, after treating a surface or fabric with the compound, the product or the compositions of the present invention, the surface or the fabric may optionally be heated to further complete the joining of the compound, the product or the composition, to the surface of the substrate. The water-stable organosilane compounds, products and compositions of the present invention, therefore, are advantageous in the treatment of a variety of substrates without the use of toxic organic solvents, and allow safe, long-term storage. of the activated organosilane compound that can be used without further preparation. In addition, the stabilizers described herein do not interfere with the attachment of the organosilane to the substrate. Additionally, the present invention provides a generally cable-friendly scheme for solvating some water-insoluble organosilanes. Also apparent will be those applications in which the organosilanes are prepared, dissolved, stored, applied and, in some way, used in water. Additionally, applications of the organosilanes R "SiX ^ _" in other solvents or mixed in other media (solids, mixtures of polymers, fillers, pigments, powders, ttes or emulsions) where water exposure occurs, will also be evident. »But it could be harmful due to the undesirable or out-of-time self-condensation of silanol. Furthermore, stabilization compounds and methods could be used in addition to or in combination with various stabilization methods known in the art for organo-lanes such as the use of surfactants and ionic or non-ionic detergents. Additionally, it is believed that the compounds, the products and the compositions of the present invention lead to improved wetting and / or coating, because the complex of stabilizer / organs? The partially hydrolysed ring is dense in hydroxyl groups, thus providing more hydrogen bonding for the surface OH groups. Also, the compounds, products and compositions herein can be used in the incorporation of an organosilane antimicrobial agent in most textile products (fabrics and nonwovens) and in 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 increase the manufacturing cost. The incorporation of the compounds, products and compositions of the present invention during the dyeing process results in a textile material with an incorporated antimicrobial agent, which has the characteristics, binding and antimicrobial protection of the organolenoid. The incorporation procedure: 1) does not add any additional steps in the manufacturing process nor does it require any modification of the equipment; and 2) it is believed that it does not lose its anti-microbial characteristics or its effectiveness during the subsequent production of textile products. By incorporating the compounds, products and water-stable compositions of the present invention, during the dyeing process "not only would the organosilane antimicrobial agent remain unaffected by the dyeing agent, but also the textile products of the final product they would also exhibit excellent dyeing properties. The water-stable organosilane compounds, products and compositions of the present invention are useful for numerous applications, as to prevent pre-existing instability and insolubility, or at least for the use prevented or restricted from some organ agents lano. For example: Treat food crops (for example) perishable, talas such as vegetables, fruits or grains) after removing (collecting / harvesting) them with the compounds »the products and the compositions of the present invention, imparts anti-icrsbian protection to the outer surface of the food crop. It is believed that such protection occurs without the antimicrobial agent diffusing, migrating or being leached from the antimicrobial coating attached to the food article, and providing prolonged, second and non-toxic antimicrobial protection. The method involves treating fruits and vegetables in the rinse cycle, during or after normal washing / spraying with water or during or after bleaching. The perfect cleaning of fruits and vegetables in the processing plant is preferred to eliminate micro-organisms. As will be recognized by one who is an ordinary expert in the field »machines are used initially to remove dirt» chemicals used in growth »bacteria that spoil them or other foreign materials. These machines also use water spray at high speed to clean the products. After cleaning »raw food or other culture materials are prepared for further processing, such as bleaching (ie, the food is cooked in water at 87 ° C-98 ° C) or exposed to steam ). Microorganisms are controlled by the production plant until the fruit or vegetable is removed. But once organisms such as yeasts, molds and bacteria are removed, they begin to multiply, causing the food to lose flavor and change color and texture. To protect the food against its damage, "numerous methods" have been used, such as refrigerators to slow microorganisms and delay spoilage. Unfortunately, the known methods will keep raw food for a few weeks at most. The compounds, products and compositions of the present invention can retain these products for extended periods. For example, compositions, products or compounds can be added to an existing water line, which feeds the sprinklers for the springs, when such sprinklers are used. Otherwise, a simple immersion procedure may be used, where immersion requires only a few seconds to impart antimicrobial protection. The low concentrations of aqueous solution of 0.1 to 154 (0.1 to 1% by volume) of the compositions give satisfactory results. Additionally, it is believed that the method described herein can also control pathogens in bird carcasses and in other susceptible meat and fish products. Treatment of milk bottles for baby / ugo for baby; mammals, pacifiers and toys with the compounds, products and compositions of the present invention in the factory or leaching the agent from the bonding surface, may provide prolonged and safe / non-toxic antimicrobial protection. Treating such items also eliminates odors caused by microbial contamination. An immersion method such as that described above can be used to treat those articles. So far, parents have used soaps, detergents and surface cleaners to alleviate the contamination problems of those items. However, these and similar treatments, for the most part, have been inadequate and make it necessary to repeat the treatment. Additionally, it has been found that such treatments are limited in their ability to offer control of microorganisms in a broad spectrum. Accordingly, the compounds, products and compositions herein can be used to treat such articles to prevent the development of microbes and contamination by coating them with an effective amount of the products and compounds of the invention. The articles used can be coated allowing a 1 to 2 minute immersion (for example, by immersing them) and the treated surface is allowed to dry at room temperature. The article is then rinsed of any excess antimicrobial agent. Perfect cleaning and sterilization are preferred steps to remove microorganisms from the surface of the article before "coating" said articles. Additionally, concentrations of 1054 or more by volume of the compounds, products and compositions of the invention are preferably used for durable protection. Treating surgical gloves with the compounds »the products and compositions of the present invention» before or during the surgical procedure »can kill the microorganisms by contact. It is believed that the treated gloves provide prolonged antimicrobial activity with safe and non-toxic antimicrobial protection. The surgical gloves are preferably "preferably" dipped in the solution of example I »d to 154 weight / volume» for at least 30 seconds. This method will allow doctors to use and »if necessary» reuse the same gloves (even without removing them) without undue fear of contamination. Furthermore, whoever is an ordinary expert in the field will be able to implement numerous other end uses based on the description of the compounds, products and compositions of the present invention. For example, the following uses are contemplated: applications and substrates: 1. Concrete »concrete water pipes» storm and sewage pipes »treated with the compounds, products and compositions of the present invention. Agents kill microorganisms by contact and provide prolonged antimicrobial protection to prevent deterioration of concrete and its coatings; 2. Dental brushes, combs »hairbrushes, dentures and catches. 3. Filters for tubs and swimming pools »that meet strict requirements that no other antimicrobial agent can meet» and protection for air filtration »as in air conditioning filters» HVAC and cabin air applications. 4. Marble plates (facades of buildings »tombs» floors) treated with the compounds »the products and compositions of the present invention. 5. Alcohol to rub. 6. Statues and works of art exposed. 7. HDP, plastic covers for high density polyester fabric »for waste dumps» water tanks and »in general» for the protection of the earth. 8. Liquid additive (as conservator of the flower water for potted plants and cut flowers). 9. Fiberglass coated with silicone and with Teflon »with antimicrobial protection» that includes the acrylic back wall covering.
. Dryvitt and stucco finish. 11. Embodiment treated with the compounds, products and compositions of the present invention; 12. A method for treating mixed cotton before or after the picking machines form the cotton into rolls or bales. 13. Packing and containers for food. 14. Bio-films and adhesives (ribbons and wafers of 1 icon). 15. Single-layer roofs and timber for ceilings. 16. Fiberglass reinforcement product. 17. Antimicrobial treatment of a transplant. 18. Anti-microbial treatment of an organ or cartilage transplant. 19. Antimicrobial treatment of an artificial transplant, such as bone replacement. 20. Antimicrobial treatment of a non artificial artificial skin transplant or a mixture of both. 21. Treatment of a transplant to reduce rejection by the organism that receives it. 22. Treatment of a skin transplant. 23. Treatment of a transplant to reduce undesirable deposits, especially for artificial transplants. 24. Treatment to accelerate the union of natural bone to non-organ transplants. 25. Conservation of liquids for consumption, without pasteurization or nutrient reduction. 26. Treatment of the skin »without incorporating any insoluble material in water, to stabilize the siloxane. 27. Supply of drugs in time, based on the hydrolysis of the siloxane linked to areas of activity. 28. Throat pills, which give relief and kill germs. 29. Treatment of contact lenses to prevent or reduce the formation of deposits. 30. Treatment of contact lenses for p eve i microbial development. 31. Incorporation into commercial polymers, to make them antimicrobially active and / or prevent damage by microbial development on the surface. Examples of commercial polymers are: polyester, nylon polyamide), polyvinyl chloride, polyethylene, polypropylene, polystyrene, polyurethane, polyvinyl alcohol, polymorph. 32. Incorporation in lenses and contact to obtain the results previously in rows 28 and 29, in the long term and without additional superficial treatment. 33. Incorporation in polyester to provide containers for foods that have antimicrobial properties, without separate surface treatment.
GG
34. Incorporation in polypropylene or polyethylene to give food containers with antimicrobial properties, without separate surface treatment. 35. Incorporation of siloxane in CD-Rom to reduce the effect of microbes that develop on the surface. 36. Treatment of paper (newspapers, books, documents) to prevent aging, for example, yellowing and weakening of the material. 37. Effective cleaning and prevention of odor in cages for animals »for example» of birds »white mice» pigs »guinea pigs» horses »cattle» rats and mice. 38. Disinfection in spacecraft "at low vapor pressure and without irritation for astronauts by the cleaner" but with eTevada residual activity. 39. Applications in clean rooms »that is, clean rooms used in the microprocessor industries» reduction of the harmful effects of microbes and uses as a binding agent for dust and a static load inhibitor. 40. Application of a non-conductive layer on circuit boards, to prevent damage by dust and other atmospheric pollutants. 41. Application of a durable, non-irritating UV protector for polymers, leather, leather and wood. 42. The UV protector can be formulated, for example, with a sun-tanning lotion or, for example, with lubricants to protect the polymers, such as on instrument panels and automobile tires. 43. Protection of photographic products against microbes, for example: lenses, photographs, films and solutions used in film development. 44. Protection of technical products, such as lenses, photographs, film and solutions used in film development, against static and dirt. 45. Protection of photographic products against smudges and scratches, for example, on lenses, photographs, film and solutions used in film development. 46. Protective coating for microcapsules. 47. Use of self-assembled layers in the design and manufacture of microcapsules. 48. Use of self-assembled layers in the "wiring" of the microcapsules. 49. Use of self-assembled layers in the manufacture of mollic ares processors. 50. Additive for drying sheets »to make the fabrics antimicrobially active. 51. Assist in the closure and healing of wounds »and prevention of infection in wounds. 52. Treatment of nail fungus »for example» by addition to the nail painting.
H.H
Those skilled in the art will appreciate »in view of what has been described here» that the compositions of this invention are useful »irrespective of the mechanism of operation, which may or may not include the hydrolysis of siloxane to silanol, and the possible reaction of silanol with the polyol or, alternatively, the simple stabilization of the siloxane by interaction with the polyol, for example, by hydrogen bonding. It will also be understood that when a composition containing an organosilane is mentioned, it is intended that the organosilane mixtures are comprised therein. In the particularly preferred embodiments, the composition according to this invention is used to treat skin or other tissues (bone, soft tissues) for use in a transplant "in order to reduce contamination by microbes. Likewise, the composition is useful in any toothpaste formulation known in the art to increase the anti-cavity properties of said composition, by means of the antimicrobial treatment of the dies. In other preferred embodiments, the composition is used to protect paper products, to produce durable metal finishes such as any automotive wax formulation known in the art, to prevent scratching of the paint and as a protector against dirt build-up. . The preferred embodiments of the compounds »the products» the water-based antimicrobial compositions »described above» and the methods »are given in the following examples. Other aspects of the invention will be apparent from the following examples "which are for illustrative purposes only" and which are not intended to serve as a limitation to the present invention.
AXIS 1
In one embodiment, the present invention provides a water-stable glucose composition and a silky quaternary ammonium salt. When the mixture is applied, the glucose is most likely partially released and the product hydrolyzed. However, said release is not necessary for the operability of the present invention. Its occurrence or non-occurrence does not depart from the general efficacy of the compounds, products and compositions of the present invention. Rather, the notion that glucose is released (or any other of the stabilizers herein) is offered as a possible explanation for the surprising utility and effectiveness of the claimed invention. It is not clear that the stabilizer must be released when the organosilane is attached to a substrate. The dimethyl-amyloxy-trimethoxysilyl-propionate chloride stabilized with glucose is stable in water up to 10 5% w / w of the siloxane. One of ordinary skill in the art will recognize that the stability of other organosilanes can vary and depends on the specific stabilizer used. In any case, the siloxane and glucose are mixed, optionally at a final concentration of siloxane higher than the working concentration, and then diluted to the desired active concentration in water.
EXAMPLE 2
Compositions in which the stabilization of the siloxane is achieved by mixing with sucrose, have a stability similar to that described in example 1, for its stabilization with glucose.
EXAMPLE 3
A series of polyols were tested for their ability to stabilize Dow Corning 5772"which is a mixture of 3- (rimethoxysi 1 i 1) propyl chloride. Idimeti loctadec 1-ammonium and 3-chloroprop r? Meto? Isi tin, in aqueous solutions, and the degree of stabilization was monitored for various periods of time. In general, the highest concentrations of siloxane become turbid at night, in the absence of a stabilizer. Accordingly, when the aqueous siloxanes remain stable overnight, in the presence of the stabilizer, the polyol is considered to have at least minimal utility, in accordance with this invention. However, experts in the field will recognize that, for practical and commercial applications, the longer the period during which the composition is stable, the better. As a consequence a group of solutions with known concentration of the stabilizer is prepared in deionized water. A known amount of the solution was mixed in a blister and in some cases, additional deionized water and the siloxane. The ampoule was sealed with paraffin to prevent evaporation and stored at room temperature. The percentage of antimicrobially active silo was calculated by multiplying the weight of Dow Corning 5772 added »by 0.72 and dividing by the sum of all the materials added (polio!» Dow Corning 5772 »deionized water). It was found that for concentrations of at least 1054 siloxane "or lower concentrations" about 1-2054 of the polyol was effective to stabilize the aqueous solution.
E ^ EMPLQ 4
A solution to 554 siloane »with 0.9454 to 1954 sucrose» remained clear for at least seven weeks. Another sample »about 554 siloxane» remained clear for at least eight months.
EXAMPLE 5
A solution to 554 of the serum with 0.9454 to 1954 of mannitol permanac or clear for seven weeks. At a high concentration of mannitol, it is not completely soluble but is still active as a siloxane stabilizer.
EXAMPLE 6
A sol ution at 554 of oxalone with 0.9454 to 1954 of glycol remained for at least eight weeks.
EXAMPLE 7
A 1054 solution of siloxane »with 0.8554 to 1754 L-ascorbic acid» remained clear for at least five weeks »after two days» solutions with up to 1854 of whether loxane remained clear with just 0.7954 L-ascorbic acid.
EXAMPLE 8
A 954 solution of siloane with 4,154 to 1854 of aqueous glyoxa solution remained clear for at least three weeks.
EXAMPLE 9
In terms of polymeric polyols, a solution to 554 siloxane, 0.09754 agar was found to be stable for at least a week. As will be appreciated, for the agar, it is necessary to heat the agar master solution to obtain a solution of the agar. which is then cooled before, or in the course of mixing with the siloxane. The resulting solution is a viscous liquid or a solid when it is cooled.
EXAMPLE 10
In terms of an oxidized sugar, it was found that a solution to 9,754 siloxane »0.954 D-glucurono-6» 3-lactone. It was stable for at least four weeks.
EXAMPLE 11
A siloxane solution with tannic acid was not stabilized to any significant degree. This result may indicate that the impurities, for example, the oxidation products present in the tannic acid, have inhibited their action as a stabilizer. Alternatively, the limited stabilization provided by the tannic acid may indicate that at least two adjacent hydroxyls (separated by less than three atoms) of the stabilizer are preferably non-aromatic.
EXAMPLE 12
In accordance with this invention, numerous compositions comprising mixtures of siloxanes and polyols can be contemplated for a wide variety of applications. Because the stabilizers of this invention include non-toxic biocodable substances, such as simple sugars and more complex carbohydrates, compositions such as shampoos, hand and face creams, and compositions that will be in contact with food, are acceptable applications. There are many compositions known in the art for this type of application, to which those skilled in the art could apply the present disclosure and, therefore, no great detail is given here about the various components of those compositions. Thus »shampoo, hand lotion, toothpaste and any other composition for contact with biological material, known in the art, may also include the composition according to this invention. However, said biological contact compositions are by no means the only useful compositions. Other compositions known in the art, such as automobile wax, furniture polish, shoe shine products, leather treating compositions or glassware compositions are improved by including the composition according to this invention. From the foregoing examples, those skilled in the art will recognize that the stabilizers described herein can be used at any minimum concentration at which they are found to have a stabilizing effect, and can be used up to any maximum concentration at which they remain soluble. Even when some amount of solid stabilizer is present, it is not expected to have any harmful effect (see the previous experiment, in which a high concentration of mannitol was used), although it is anticipated that »in terms of siloxane stabilization, a point is reached in which the benefit is decreased, in which the increased stabilizer concentrations do not give the corresponding increases in the siloxane stabilization. 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 spirit or scope of the invention. Other embodiments of the invention will be applicable to those skilled in the art, when considering the specification and practice of the invention described herein. It is intended that the specification and examples be considered only as exemplary, indicating the true scope and true spirit of the invention by means of the following claims.
Claims (32)
1. - A composition characterized in that it comprises a mixture of: (a) an organoleno of the formula R ^ Si ^. ^ "Where" n "is an integer from 0 to 3; and R, independently, is a non-hydrolysable organic group; and each X. independently "is a hydrolysable group" with (b) a polyol containing at least two hydroxy groups "wherein at least two of the at least two hydroxy groups are separated by less than three intermediate atoms.
2. The composition according to claim 1 »further characterized in that" n "is an integer from 0 to 2" each R "independently" is alkyl "alkyl or aromatic alcohol; every X »depends entirely» is hydroxy. alkoxy »halogen» acetyl »acetoxy» acyl; a hydroxylated polymeric portion, solid or liquid »polyether or polyalkylether, and the polyol is glucose, sucrose, fructose» mannitol. ascorbic acid; and optionally including an antioxidant »adenosine, glucuronic acid» lucurone »dextran. aqueous gland, fucose »cellulose» partially hydrolyzed cellulose »soluble starch» starch-acrylic acid graft copolymer »a nucleoside, a nucleotide, an oligonucleotide or a polynucleotide.
3. The composition according to claim 2, further characterized in that the polyol is a carbohydrate.
4. The composition according to claim 3, further characterized in that the carbohydrate is selected from the group consisting of monosaccharides, disaccharides, oligosaccharides, polysaccharides, modified carbohydrates, graft and block copolymers of carbohydrate, partially alkylated carbohydrates, etc. or aceti sides; carbohydrate oxidation products »reduced carbohydrates and substituted carbohydrates.
5. The composition according to claim 3 »further characterized in that the substituted carbohydrate is selected from the group consisting of nucleotides and nucleic acids.
6. The composition according to claim 3, further characterized in that the carbohydrate is a "natural or unnatural" ketose or aldose or the enantiomeric form D or L.
7. The composition according to claim 6. further characterized in that the aldose or the ketose is glucose »fucose» fructose »a polymer» an oxidation product »a reduction product or a substituted derivative thereof» soluble in water.
8. The composition according to claim 1 »further characterized in that the organosilane has the formula II, III, IV or V: (RA) SiRaN * (R3) (") (Rβ) Y ~ (II); (Ra.) 3SiRaN (R3) (^) (III); (Ra.) 3SiRaRaB (IV) (R) aSi (R3ß) (R3 ^) (V), where each R »independently, is halogen or Rß0, where Rβ is H» alk of 1 to about 22 atoms carbon, acetyl, acetoxy, acyl, propylene glycol »ethylene glycol, polyethylene glycol» polypropylene brine; block and copolymer of ethylene- and propylene glycol, the alkyl monoether of 1 to 22 carbon atoms of propylene glycol »ethylene glycol» polyethylene glycol »polypropylene glycol; block and copolymers of ethylene and propylene glycol or the monoester of a carbonic acid of 1 to 22 carbon atoms and propylene glycol et al, polyethylene glycol, polypropylene glycol; block and copolymers of ethylene and prop lengl col; octylphenol; nonylphenol, and sorbitan ethers; R3ß is H. halogen (such as Cl, Br, F or I) »NHa (CHa) aNHRa, NHaRa, C3Hβ0aRa, C ^ HBOaRa, Na0 (CHa0) P (0) Ra, O CICHaCßH ^ Ra; Raß and Ra--, "independently, are halogen, H" alkyl of 1 to about 22 carbon atoms »acrylic» vinyl »acetylenic» benzyl »styryl» propynyl »isobutyl» phenyl or n-octyl; Rw is benzyl »vinyl or alkyl of about 22 carbon atoms; R3 and R ^, "independently" are lower alkyl alcohol, lower alkoxy of 1 to 4 carbon atoms, alkyl of 1 to about 22 carbon atoms; or R3 and R ^ ». together »can form a morphol or a cyclic or heterocyclic ring» unsaturated or saturated »of five to seven members of the formula Vi: -R3- (R ^) K- ^ - (VI); where k is an integer from 0 to 2; R ^ "when the ring is saturated, it is CHa» 0, S, NH, NHa-, NCHjtCHjMHa, NCHaCHaNHa *, NCHaCHa (R) (R "), NCHaCHaN- (Rß) (Rß) (RÍO), N ( alkyl), N (aryl), N (benzyl); where each of Ra, R
9, RAO »independently, is benzyl, polyether, lower alkyl alcohol of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, or alkyl of 1 to about 22 atoms of carbon; and R., when the ring is unsaturated, is: CH, N, N + H, N + (alkyl), N + (aryl). N + (benzyl), N-CH, »- N, N-H-CHa-N, N * (alkyl) -CHa-N, N * (aryl) -CHa-N; N * (benzyl) -CHa-N, wherein the ring is unsubstituted or substituted by alkyl of 1 to 22 carbon atoms, ester, aldehyde, carboxylate, amide, thionamide, nitro-amine or halide; R <3> is lower alkyl alcohol, preferably 1 to 6 carbon atoms, and better still, 1 to 4 carbon atoms, CHaCßHB, polyester, such as a polyethylene glycol or a polypropylene glycol, alkyl of 1 to 22 carbon atoms. carbon »or is a ring of five to seven members» of formula VI »as described above; and Y- is an anionic portion suitable for forming the salt of the compound of the formula II »III» IV or V. 9.- A stable composition in water »characterized in that it comprises the composition of claim 1 and water.
10. The composition according to claim 1 »further characterized in that the organosilane is 3- (trimethoxysilyl) propyl dimethyl loctadecyl-ammonium chloride and the polyol is glucose» sucrose »fructose» mannitol »ascorbic acid and optionally includes antioxidant »adenosine. glucuronic acid »glucuron» dextrose. cellulose »partially hydrolyzed cellulose» soluble starch »a starch-acrylic acid graft copolymer. a nucleoside »a nucleotide» an oligonucleotide or a polyucleotide.
11. A composition for treating a substrate "characterized in that it comprises a carrier and an effective amount of the composition of claim 1.
12. The composition according to claim 11» further characterized in that the carrier is different from water.
13. The composition according to claim 1, further characterized in that the organosilane is 3- (trimethoxysilyl) propyldimethyloctadecylammonium chloride »3- (trimethoxysilyl) propi 1di eti 1 chloride (deci 1> ammonium» 3-chloropropyl) -trimei Isi laño »3-chloroprop 1 trimethoxysilane» octadecyl-trimethoxyß lano or per luoroocti Itrietoxisi láño »and the polyol is an aldose» a ketose »a polymer» an oxidation product »a reduction product, a substitute or replacement product Polymer thereof 14. The composition according to claim 1, further characterized in that the organosilane is: (CH30) 3 Si (CHa) 3 * (CH3) 2CallHa7C1- »(CH30) 3 Si (CHa) aN * (CHa) a! Ca.ßH37Br-, (CH3O) 3Si (CHa) 3N * (Ca.oHa.a.) aCH3C1 ~, (CHaO) 3Si (CH,) ßN * (C? aH, ±), CH "Br-, (CH30) 3Si (CH2) 3N + (CH3) 3Cl-, (CH30) 3Si (CH2) 3N + (CH3) 2CgH17Cl-, (CH3O) 3Si (CH2) 3N + (CH3) 2C10H2ICl-, (CH30) 3Si (CH2) 3N + (CH3) 2C12H25Cl ", (CH 3 O) 3 Si (CH 2) 3 N + (CH 3) 2 C
l 4 H 29 Cr, (CH 3 O) 3 Si (CH 2) 3 N + (CH 3) 2 C 16 H 33 Cl-, (CH3O) 3Si (CH2) 3N + (CH3) 2C20H41Cl-, (CH3?) 3Si (CH2) 3N + (C4H9) 3Cl-, (CH 3?) 3 Si (CH 2) 3 N + (C 2 H 5) 3 Cl-) (CH 3 CH 2 O) 3 Si (CH 2) 3 N + (CH 3) 2 C 18 H 27 Cl-, (CH3O) 3Si (CH2) 3NHC (0) (CF2) 6CF3, (CH30) 3Si (CH2) 3NHC (O) (CF2) gCF3, (CH3O 3Si (CH2) 3NHC (O) (CF2) 10CF3, (CH30) 3Si (CH2) 3NHC (0) (CF2) 12CF3, (CH3?) Si (CH2) 3NHC (0) (CF2) l4CF3, (CH30) 3Si (CH2) 3NHC (0) (CF2) 16CF3, (CH3O) 3Si (CH2) 3NHSO2 (CF2) 7CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 6CH3, (CH3O) 3Si (CH2) 3N +, (CH3) 2 (CH2) 3NHC (0) (CH2) 8CH3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O) (CH2) 10CH3, (CH3?) 3Si (CH2) 3N + (CH3) 2 ( CH2) 3NHC (0) (CH2) 12CH3, CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O) (CH2) 14CH3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CH2) 16CH3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) (CH2) 3NHC (0) (CF2) 6CF3) (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) ) 3NHC (0) (CF2) 8CF3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O) (CF2) 10CF3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 12CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (0) (CF2) 14CF3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHC (O ) (CF2) 16CF3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS2 (CF2) 7CF3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHSO2 (CF2) 9CF3, (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 11CF3, (CH3?) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 13CF3) (CH3O) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHSO2 (CF2) 15CF3, (CH30) 3Si (CH2) 3N + (CH3) 2 (CH2) 3NHS02 (CF2) 16CF3, (CH3O) 3Si (CH2) 3NHC6H4COOH, (CH3O) 3Si (CH2) ) 3NHC6H COOCH3, (CH3O) 3Si (CH2) 3NHCbH4C00C2H5, (CH3O) 3Si (CH2) 3NHC6 H4COOC3H7, (CH3O) 3Si (CH2) 3NHC6H4COOC4H9, (CH3O) 3Si (CH2) 3NHC6H4COOCH2C6H5, (CH3O) 3Si (CH2) 3NHC6H4COOCH2C6H4NH2, (CH3O) 3Si (CH2) 3NHC6H4COOCH2C6H4N (CH3) 2, (CH3O ') 3Si (CH2) 3NHC6H4COOCH2C6H4N (CH2CH3) 2) (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH3) 3 Y ", (CH30) 3Si (CH2) 3NHC6H4COOCH2C6H4N + (CH2CH3) 3 Y ", (CH30) 3Si (CH2) 3NCH3C6H4COOH, (CH3O) 3Si (CH2) 3NCH3C6H4COOCH3, (CH3O) 3Si (CH2) 3NCH3C6H4COOC2H5, (CH3O) 3Si (CH2) 3NCH3C6H4COOC3H7, (CH3O) 3Si (CH2) 3NCH3C6H4COOC4H9, (CH3O) 3Si ( CH2) 3NCH3C6H4COOCH2C6H5, (CH3O) 3Si (CH2) 3NCH3C6H4COOCH2C6H4NH2, (CH3O) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N (CH3) 2) (CH30) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N (CH2CH3) 2, (CH3O) 3Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH3) 3 Y-, (CH3?) 3 Si (CH2) 3NCH3C6H4COOCH2C6H4N + (CH2CH3) 3 Y-, (CH3O) 3Si (CH2) 3N + (CH3) 2C6H4COOH Y-, (CH3O) 3SI (CH2) 3N + (CH3) 2C6H4COOCH3 Y-, (CH3O) 3SI (CH2) 3N + (CH3) 2C6H4COOC2H5 Y-) (CH3O) 3SI ( CH2) 3N + (CH3) 2C6H4COOC3H7 Y-, (CH3O) 3SI (CH2) 3N + (CH3) 2C6H4COOC4H9 Y-, (CH3O) 3SI (CH2) 3N + (CH3) 2C6H4COOCH2C6H5 Y-, (CH3O) 3Si (CH2) 3N + (CH3 ) 2C6H4COOCH2C6H4NH2 Y-, (CH3O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH3) 2 Y-, (CH30) 3 Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y-, (CH30) 3 Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N + (CH3) 3 Y? -, (CH3O) 3Si (CH2) 3N + (CH3) 2C6H4COOCH2C6H4N + (CH2CH3) 3 Y? -, (CH30) 3Si (CH2) 3NC2H5QH4COOH, (CH3O) 3Si (CH2) 3NC2H5 H4COOCH3, (CH3O) 3Si (CH2) 3NC2H5C6H4COOC4H9, (CH3O) 3Si (CH2) 3NC2H5C6H4COOC3H7, (CH3C3Si (CH2) 3NC2H5C6H4COOC4H9, (CH30) 3Si ( CH2) 3NC2H5C6H4COOCH2C6H5> (CH30) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4NH2, (CH30) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N (CH3) 2) (CH3O) 3Si (CH2) 3NC2H3C6H4COOCH2C6H4N (CH2CH3) 2 > (CH3O) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH3) 3 Y-, (CH3O) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH2CH3) 3 Y-, (CH3O) 3Si (CH2) 3N + (C2H5) 2C6H4COOH Y-, (CH3O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH3? -, (CH3?) 3Si (CH2) 3N + (C2H5) 2C6H4COOC2H5 Y-, (CH3?) 3 Si (CH2) 3N + (C2Hs) 2C6H4COOC3H7 Y- > (CH3?) 3Si (CH2) 3N + (C2H5) 2C6H4COOC4H9 Y-, (CH3?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H5 Y-, (CH3O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N2 Y-, (CH3O) 3 Si (CH2) 3N + (C2Hi) 2C6H4COOCH2C6H4N (CH3) 2 Y-, (CH3O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y-, (CH3O) 3Si (CH2) 3N + (C2H3) 2C6H4COOCH2C6H4N + (CH3) 3 Y? (CH3O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N + (CH2CH3) 3 And Y ", (CH3CH2O) 3Si (CH2) 3NHC6H4COOH, (CH3CH2O) 3Si (CH2) 3NHC6H4COOCH3, (CH3CH20) 3Si (CH2) 3NHC6H4COOC2H5, (CH3CH2O) 3Si (CH2) 3NHC6H4COOC3H7, (CH3CH2O) 3Si (CH2) 3NHC6H4COOC4H9, (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOCH3, (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOC2H5) (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOC3H7, (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOC4H9, (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOCH2C6H5(CH3CH20) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4NH2, (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N (CH3) 2, (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N (CH2CH3) 2) (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH3) 3 Y- , (CH3CH20) 3Si (CH2) 3NC2H5C6H4COOCH2C6H4N + (CH2CH3) 3 Y ", (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOH Y-, (CH3CH2?) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH3 Y", (CH3CH20 ) 3Si (CH2) 3N + (C2H5) 2C6H4COOC2H5 Y-, (CH3CH20) 3Si (CH2) 3N + (C2H5) 2C6H4COOC3H7 Y-, CH3CH2O) 3Si (CH2) 3N + (C2H5) 2C6H4COOC4H9 Y-, (CH3CH20) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H5 Y-, (CH3CH2O) 3Si (CH2) 3N + (C2H5) 2C (HH4COOCH2C6H4NH2 Y-) (CH3CH2O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N (CH3) 2 Y-, (CH3CH2O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N (CH2CH3) 2 Y-, (CH3CH2O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N + (CH3) 3 Y? \ O (CH3CH2O) 3Si (CH2) 3N + (C2H5) 2C6H4COOCH2C6H4N + (CH2CH3) 3 Y? -.
15. - 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, Cl (CH 2) 3 Si (OCH 3) 3, Cl (CH 2) 3 Si ( OCH2CH3) 3, Cl (CH2) 3SiCl3, C3H502 (CH2) 3Si (OCH3) 3, C3H502 (CH2) 3Si (OCH2CH3) 3, C4H5O2 (CH2) 3Si (OCH3) 3, C4H502 (CH2) 3Si (OCH2CH3) 3, CH3SiHCl2, NaO (CH30) P (0) (CHa) 3Si (OH) 3 'SiHClg, n-2-v hydrochloride or 1benzyl lami o -ethyl-3-aminopropyltrimethoxysilane, HaC = CHSi (OCOCH3) a, HaC = CHSi (OCHa) 3, HaC = CHSi (OCHaCH3) 3, HaC = CHSiCla, (CH3 aSiCla, CH3 aSi (0CHß a, (CßHB) aSiCla, (CaHß) SiCl3, (CaHß> Si (OCH3) 3, (CaHB ) S (0CHaCH3) a, isobutyl 1 tri ethoxy, n-octytrietoxisi o, CH3 (CßHB) SiCla, CH3SiCl3, CH3Si (0CH3) 3, C ^ HßS Cla »CßHBSi (OCHa - ,, CaH ^ S Cla »C ^ H ^ H OCH ^) ^, SiCl ^, ClCHaCßH-» CHaCHaSiCl3", ClCHaCßH ^ CHaCHaSi- (OCH3) 3, ClCHaCßH ^ CHaCHaSi (0CHa. H3) 3, deci 1 trie! Orosiño, dichloroethyl ( 4- et Ifenet 1) yes tin, dietoximeti Ifeni Is tin, C3- (d ethylam) propyl 3-tr meto? Isi tin, 3- (dimetho-imethyl-sil) l) -l-propane ol, dimethoxyet 1 vin Is tin, ethacrylate of 3-Ctris (tr meti Isi 1 ilo? i) -if 1 Ipropyl, trichloroC4- (chlorometi 1) fe 13 -if o, meth lbis (tr and lsilyloxy) vnl- si the o »met Ipropo? is the or »or triclorociclopent Is tin.
16. A compound characterized in that it has the formula (R) "Si (X) ^ _ _ > , (R ^ aL) > ,, where n is an integer from 0 to 3; and is an integer from 1 to 4; each R, independently, is a non-hydrolysable organic group; each X, independently, is a hydrolysable group; and each ^ A is a polyol containing at least two hydro? i groups; wherein any two of the at least two hydro groups ?? they are separated by no more than two intermediate atoms; and where the R ^ ,. it is attached to the Si by removing the hydrogen from at least one of the two hydroxy groups, so that at least one of the oxygens of the at least two hydroxy groups is attached to Si.
17. - The composition according to claim 1, further characterized in that it is formed by the mixing of an organosilane of the formula II, III, IV or v: (Ra>) SiRaN * (Ra) (R-4) (RB) Y - (II); (R) 3SiRaN (Ra) (R ^) (III); (Ra.> SiRaR3B (IV); (Rx) aSi (R ß) (Ra7) (V); wherein each R ?, independently, is halogen or Rß0, where Rβ is H »alkyl of 1 to about 22 carbon atoms »acetyl» acetoxy »acyl, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, ethylene- and propylene glycol block and copol» the alkyl monoether of the 22 carbon atoms of propylene glycol, ethylene glycol, pol ethylene glycol »polypropylene glycol; block and copolymers of ethylene and propylene glycol or the onoester of a carbonic acid of 1 to 22 carbon atoms and propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, octylphenol, nonylphenol, and sorbitan ethers R3ß is H, halogen (such as Cl, Br, F or I) »NHa (CHa) 3NHRa, NHaRa, C3HßOaRa, C ^ HßOaRa, Na0 (CH30) P (0) Ra , O CICHaCßH Ra; Raß and 37, independently, are halogen »H» alkyl of 1 to about 22 carbon atoms, acrylic, v nile acetylenic »benzyl, styryl, propynyl, isobutyl, or n-fen what October it.; Rw is benzyl »vinylo or alkyl of about 22 carbon atoms; Ra and R ^. ndependently. they are lower alkyl alcohol. lower alkoxy of 1 to 4 carbon atoms, alkyl of 1 to about 22 carbon atoms; or Ra and R ^.; together, they can form an ace orfoli ao a cyclic or heterocyclic ring »unsaturated or saturated» of five to seven members of the formula Vi: - 3- (R ^, l < -R ^ - (VI); where K is an integer from 0 to 2; R ^, »when the ring is saturated» is CHa »O» S »NH» NHa- < -, NCHaCHaNHa »NCHaCHaNHa-, NCHaCHa (Rß) (R). NCHaCHaN * (Ra) (R) (R10 N (alkyl), N (aryl), N-benzyl); where each of Ra »Rß» and R4e > »Independently» is benzyl »polyether» lower alkyl alcohol with 1 to 4 carbon atoms »lower alkoxy of 1 to 4 carbon atoms, or alkyl of 1 to about 22 carbon atoms; and R7 > when the ring is unsaturated, it is: CH »N» N + H, N + (alkyl). N + (aryl) »N + (benci lo), N-CH ^ -N. N? -CHa-N »N * - (alkyl) -CHa-N» N * (ari lo -CHa-N »N * (benzylo) -CHa-N, wherein the ring is unsubstituted or substituted by alkyl of the 22 carbon atoms »ester» aldehyde »carboxylate» amide »thionamide» nitro »amine or halide» R ,,, is lower alkyl alcohol CHaCßHB »polyether, alkyl, alkoxy, per-alkyl-alkyl» perfluoroalkylcarboxylate »wherein the Alkyl »alkoxy» perloalkyl »perfluoroalkyl 1-sulfonate or perfluoroalkyl Icarbonate have from 1 to about 22 carbon atoms» or is an anvil or from five to seven members »of formula VI, as described above; and Y- is an anionic portion suitable for forming the salt of the compound of formula II »III» IV or V; with a polyol having at least two hydroxy groups, wherein any two of the at least two hydroxy groups are separated by more than two ternary atoms.
18. - The composition according to claim 17 »further characterized in that it is an aqueous composition.
19. A method for treating a substrate "characterized in that it comprises contacting the substrate 5 with a sufficient amount of the composition of claim 1 for a period of time sufficient for the treatment of the substrate.
20. A method for dyeing and treating a substrate, characterized in that it comprises contacting the substrate 10 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 R ^ SiX, * ». ,,» where "n" is an integer from 0 to 3 »and R» i dependently »is a non-hydrogenable organic group; and each X »15 independently, is a hydrolysable group; with (b) a polyol containing at least two hydroxy groups "where "Any two of the at least two hydroxy groups are separated by no more than two intermediate atoms; for a sufficient period of time to dye and treat the substrate.
21. A method for treating a food article antimicrobially, characterized in that it comprises contacting the food article with an effective amount of the product formed upon mixing: (a) an organosilane of the formula R "SiX? "n" is an integer from O to 3; and R »25 independently, is a non-hydrolysable organic group; and each X, independently "is a hydrolysable group; with (b) a polyol containing at least two hydroxy groups "wherein any two of the at least two hydroxy groups are separated by no more than two intermediate atoms" for a period of time sufficient to treat the food article antimicrobially.
22. A method for antimicrobially coating a fluid container, used to contain a human or animal consumable product, characterized in that it comprises contacting the container with an effective amount of the product formed upon mixing: (a) an organosilane of the formula R ^ S? X. ».., -,» where "n" is an integer from 0 to 3"and R" independently, is a non-hydrolysable organic group; and each X »i is dependently a hydrolysable group; with (b) a polio! containing at least two hydroxy groups "wherein any two of the at least two hydro? i groups are separated by no more than two intermediate atoms; for a period of time sufficient to antimicrobially coat the container.
23. A method for antimicrobially coating a latex medical article, for use in a human or animal medical procedure, characterized in that it comprises contacting the article with an effective amount of the product formed upon mixing: (a) an organo lano of the formula R "SiX, ^ _" »where" n "is an integer from 0 to 3; and R "independently" is a non-hydrolysable organic group; and each X »independently, is a hydrolysable group; with (b) a polio! which contains at least two hydroxy groups. wherein any two of the at least two hydroxy groups are separated by not more than two intermediate atoms; for a sufficient period of time to antimicrobially coat the article.
24. The method according to claim 22 »further characterized in that the article is a surgical glove. 25.- A method to antimicrobially treat a substrate selected from the group consisting of a concrete tube »a toothbrush» a comb »a hairbrush» a denture »an orthodontic retainer» a filter for a tub or a pool » an air filter »an HVAC air system. a cabin air system * a marble item »a statue» an exposed work of art »an HDP plastic cover» a fiberglass article coated with silicone or TEFLON * "», a Dryv? tt finish »a finish stucco »mixed cotton» a b? o-film, a bio-adhesive, a single layer roofing material »a roofing wood» a paper product »teeth» skin »bone» cartilage »a metallic finish» an automobile finish and a fiberglass reinforcing product »characterized in that it comprises contacting the substrate with an effective amount of the product formed upon mixing: (a) an organosilane of the formula R ^ SiX ^,,, where "n" is an integer from 0 to 3"and R" independently "is a non-hydrolysable organic group" and each X "independently" is a hydrolysable group "with (b) a polio! which contains at least two hydroxy groups "wherein any two of the at least two droxy groups are separated by no more than two intermediate atoms; for a period of time sufficient to treat the substrate antimicrobially. 26.- A method to improve antimicrobially a "Alcohol product for rubbing» a flower conservator »or a waterproofing solution» characterized in that it comprises 10 mixing with the product an effective amount of the product formed upon mixing: (a) an organosilane of the formula R ^ SiX ^ ,,, where "n" is an integer from 0 to 3; and R, independently, is a non-hydrolysable organic group; and each X, preferably "is a hydrolysable group; with (b) a 15 polyol containing at least two hydro? I groups, wherein any two of the at least two hydro? I groups are separated by not more than two intermediate atoms; during a * enough period of time to improve the product anti-microbially. 20 27.- A stable composition, characterized in that it comprises between about O.OOl and 2054 of a siloane and between about 0.01 and 2054 of a polyol containing at least two hydroxy groups; wherein any two of the at least two hydroxy groups are separated by not more than two atoms 25 intermediates. 28. The composition according to claim 27 »further characterized in that it comprises 0.1 to 1054 siloxane and a polyol selected from the group consisting of 0.154 to 554 of a monosaccharide, a disaccharide, L-ascorbic acid, aqueous oxalic oxalic acid. , D-glucurono-6,3-lactone; or 0.00154 up to its agar gel limit. 29. The composition according to claim 27, further characterized in that the polyol is glucose »sucrose» fructose or mannitol. 30.- The composition according to claim 27 »further characterized in that the source of the polyol is corn syrup» maple syrup or honey. 31.- A shampoo, a hand lotion, a sun tan lotion, a toothpaste, a car wax, a furniture polish, a shoe polish, a skin treatment composition or a glass treatment composition »Characterized in that they comprise the composition of claim 27. 32.- A method for forming an organosilane of the formula R" SiX ^ _ "" wherein n is an integer from 0 to 3", preferably from 0 to 2; each R »independently» is a non-hydrolysable organic group »and each X, independently, is a hydrolysable group; characterized in that it comprises mixing the starting materials for the synthesis of organosilane "in an aqueous solution" in the presence of a polyol containing at least two hydroxyls that are separated by less than three carbon atoms interspersed; wherein the polyol is present in an effective amount, sufficient to stabilize the organosilane as it is formed from the starting materials.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08852474 | 1997-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA98003600A true MXPA98003600A (en) | 1999-06-01 |
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