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WO1991017223A1 - Compositions filmogenes de vernis-emulsion contenant des siloxanes copolymeres - Google Patents

Compositions filmogenes de vernis-emulsion contenant des siloxanes copolymeres Download PDF

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Publication number
WO1991017223A1
WO1991017223A1 PCT/US1990/002542 US9002542W WO9117223A1 WO 1991017223 A1 WO1991017223 A1 WO 1991017223A1 US 9002542 W US9002542 W US 9002542W WO 9117223 A1 WO9117223 A1 WO 9117223A1
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WO
WIPO (PCT)
Prior art keywords
poly
siloxane
dimethyl
mole percent
emulsion polish
Prior art date
Application number
PCT/US1990/002542
Other languages
English (en)
Inventor
Steve M. Hurley
Eric J. Miller
Husam A. A. Rasoul
Original Assignee
S.C. Johnson & Son, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by S.C. Johnson & Son, Inc. filed Critical S.C. Johnson & Son, Inc.
Priority to CA002081009A priority Critical patent/CA2081009C/fr
Priority to EP19900907957 priority patent/EP0527124A4/en
Priority to AU56307/90A priority patent/AU644791B2/en
Priority to PCT/US1990/002542 priority patent/WO1991017223A1/fr
Priority to JP90507265A priority patent/JPH05508171A/ja
Priority claimed from CA002081009A external-priority patent/CA2081009C/fr
Publication of WO1991017223A1 publication Critical patent/WO1991017223A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09G—POLISHING COMPOSITIONS; SKI WAXES
    • C09G1/00—Polishing compositions
    • C09G1/06—Other polishing compositions
    • C09G1/14—Other polishing compositions based on non-waxy substances
    • C09G1/16—Other polishing compositions based on non-waxy substances on natural or synthetic resins

Definitions

  • the present invention is generally directed to film- forming emulsion polish compositions for furniture and similar household items.
  • the emulsion can either be a water-in-oil emulsion or an oil-in-water emulsion.
  • the emulsion polish compositions of the present invention which are specifically formulated to provide rapid smear recovery, contain certain specified copolymeric siloxanes, briefly described below.
  • copolymeric siloxanes of the present invention are briefly described as poly(dimethyl)-co- poly(methylalkyl) siloxane copolymers and poly(dimethyl)-co- poly(methyl, oxygen-containing) siloxane copolymers.
  • the present invention is thus more particularly directed to polish compositions, for furniture and similar household goods, wherein such compositions contain either poly(dimethyl)-co-poly(methylalkyl) siloxane polymer, pol (dimethyl)-co-poly(methyl, oxygen-containing) siloxane polymer, or combinations thereof.
  • Emulsion polish compositions containing these copolymeric siloxanes have been observed to possess rapid smear-recovery properties while exhibiting desirable depth- of-gloss properties as well as certain other desirable film properties.
  • the polish compositions of the present invention Upon application onto a particular substrate surface, the polish compositions of the present invention have been observed to form a rather thin (approximately 1000 to 4000 Angstroms) generally uniform film on the substrate surface. Due to the liquid nature of the resultant films of the surface-applied emulsion polish compositions of the present invention, such films typically exhibit, to a degree, visible physical evidence of surface disturbances, otherwise referred to as surface "smears", when the surface-applied film is subjected to a rubbing action.
  • surface recovery denotes not only the rate-of-recovery but also the ability of a thus "smeared" surface-applied polish film to return to its original surface appearance.
  • Polish compositions possessing superior smear recovery properties have long been desired.
  • Conventional polishes, however, and in particular the surface-applied films they produce lack this quality.
  • commercial polishes that use conventional silicone-containing or conventional silicone-based fluids, as well as certain conventional waxes, and certain low molecular weight organic oils as glossing agents seemingly initially tend to provide certain desirable surface-appearance values but, in fact, ultimately suffer from certain inherent disadvantages.
  • Such conventional polishes in particular, readily tend to show certain surface disturbances such as fingerprints and otherwise readily tend to smear.
  • compositions of Brandl et al. contain water, wax, a mixture of organopolysiloxanes, a solvent, and a water-in-oil emulsifier. Such compositions, furthermore, are said to be substantially devoid of any tendency to smear or streak and are further said to be easily applied with a minimum of physical effort. Brandl et al. teach, however, that the use of silicones of diverse types, i.e.
  • organopolysiloxanes while beneficial from the standpoint of luster, gloss and durability, nevertheless fail to provide appreciable mitigation of the smear problem as they view it.
  • the emulsion polish compositions disclosed by Brandl et al. are thus said to possess a "particularly high resistance to smearing.”
  • Schnurrbusch et al. disclose certain wax-containing surface-polish compositions which are said to be resistant to "finger-marking".
  • compositions are disclosed as containing an organopolysiloxane (such as dimethylsiloxane) , a wax, and a specified so-called "organosiloxane” containing an alkyl, an alkenyl, or a monocyclic aryl radical.
  • organopolysiloxane such as dimethylsiloxane
  • wax such as wax
  • organosiloxane containing an alkyl, an alkenyl, or a monocyclic aryl radical.
  • the present invention in contradistinction to the prior art briefly discussed hereinabove, approaches the so-called "smear problem" in a manner which is markedly different from the approach set forth either in U.S. Pat. No. 3,847,622 to Brandl et al. or in U.S. Pat. No. 3,856,533 to Schnurrbusch et al.
  • the present invention in particular, enhances the smear-recovery properties of the emulsion polish compositions disclosed herein. Indeed, the unexpected and significant increase in smear recovery, which is attributable to the polysiloxane copolymers of our present invention, is shown in the comparative-example data presented hereinbelow. In particular, the smear-recovery properties of the novel emulsion polish compositions disclosed herein were not recognized by any of the prior-art polish formulators whose work we reviewed.
  • Such conventional emulsion polish compositions contain a hydrocarbon-soluble organopolysiloxane having from 1 to 3 aryl, alkyl, or arylkyl radicals per silicon atom.
  • Such emulsion polish compositions further include a hydrocarbon solvent, a specified aluminum stearate compound, and water.
  • the alkyl radicals which Currie et al. disclose are methyl, ethyl, propyl and octadecyl.
  • the polish compositions disclosed by Currie et al. furthermore, are said to be smear-free.
  • polish compositions of our present invention do indeed smear; but, upon being smeared, recover more rapidly than conventional compositions containing conventional polydimethylsiloxane polymers of comparable viscosity and/or weight-average molecular weight relative to the above-mentioned polymeric siloxanes disclosed herein.
  • the concept of rapid smear recovery is not disclosed or even suggested by Currie et al.
  • the preferred organopolysiloxane disclosed in the Currie 'SOS patent namely dimethylpolysiloxane fluid, is shown hereinbelow as being inferior to the siloxane-containing compositions of the present invention with regard to smear- recovery properties.
  • U.S. Pat. No. 2,523,281 to Currie is directed to automobile polishes containing an organopolysiloxane having from 1 to 3 aryl, alkyl or alkaryl radicals per silicon atom.
  • Such automobile polishes also include a hydrocarbon solvent, finely-divided silica of a specified particle size, an emulsifying agent, and water.
  • the disclosed alkyl radicals include methyl, ethyl, propyl, and octadecyl.
  • U.S. Pat. No. 3,306,869 to Lahr et al. discloses floor polishes which are said to possess desirable so-called "leveling" properties as well as acceptable “scuff- resistance” properties.
  • Such floor polishes comprise a wax, a modified rosin, an emulsifying agent, and a polysiloxane- oxyalkylene block copolymer having a molecular weight below about 25,000 and a polysiloxane content in the range of from about 30 to about 60 percent by weight.
  • U.S. Pat. No. 3,341,338 to Pater also discloses a polish formulation comprising a polysiloxane-oxyalkylene block copolymer and a wax.
  • One object of our invention is to provide polish compositions for furniture and other similar household items, wherein such polish compositions exhibit rapid smear- recovery qualities.
  • the emulsion composition in particular, comprises water, at least one hydrocarbon solvent, at least one surfactant, and at least one copolymeric siloxane, herein referred to as a poly(dimethyl)- co-poly(methylalkyl) siloxane copolymer having the general formula
  • A is an alkyl radical having 10 to 20 carbon atoms
  • the above-presented copolymeric siloxane has a weight-average molecular weight of about 2,500 to about 4,000 and a viscosity of about 20 to about 200 centipoise, and wherein the "w" value is about 70 to about 91 mole percent and the "x” value is about 9 to about 30 mole percent of the above-presented copolymeric siloxane.
  • Yet another aspect of our present invention is directed to yet another surface-treating emulsion composition for furniture and similar household items.
  • Such an emulsion composition in contradistinction to what was briefly disclosed above, comprises water, at least one hydrocarbon solvent, at least one surfactant, and at least one other copolymeric siloxane, herein referred to as a poly(dimethyl)- co-pol (methyl, oxygen-containing) siloxane copolymer having the general formula
  • B is (CH2)i(L) (CH2CH2 ⁇ ) n R, wherein i is an integer from 3 to 10 inclusive, wherein L is -0- or -C00-, wherein n is either zero or an integer from 1 to 3 inclusive, wherein R is -H, -CH 3 , or -C 2 H5, wherein the copolymeric siloxane has a weight-average molecular weight of about 1,000 to about 4,000 and a viscosity of about 10 to about 250 centipoise, and wherein the "y" value is about 62 to about 92 mole percent and the "z” value is about 8 to about 38 mole percent of the second above-presented copolymeric siloxane.
  • the second above-presented copolymeric siloxane is thus characterized as a poly(dimethyl)-co-poly(methyl, oxygen- containing) siloxane copolymer because the latter portion thereof contains at least one methyl group and at least one oxygen group.
  • one embodiment of the polish composition of our invention comprises water, at least one hydrocarbon solvent, at least one surfactant, and at least one copolymeric siloxane.
  • copolymeric siloxanes of our present invention are selected from the group consisting of pol (dimethyl)-co- poly(methylalkyl) siloxane copolymer, poly(dimethyl)-co- poly(methyl, oxygen-containing) siloxane copolymer, and combinations thereof.
  • the poly(dimethyl)-co-poly(methylalkyl) siloxane copolymer of our invention has the general formula
  • A is an alkyl radical having 10 to 20 carbon atoms, wherein the copolymeric siloxane has a weight-average molecular weight of about 2,500 to about 4,000 and a viscosity of about 20 to about 200 centipoise, and wherein the "w" value is about 70 to about 91 mole percent and the "x” value is about 9 to about 30 mole percent of the copolymeric siloxane.
  • a more preferred poly(dimethyl)-co-poly(methylalkyl) siloxane copolymer has a "w” value (the mole percent of silicon atoms having dimethyl groups attached) of about 85 to about 95 mole percent of the copolymeric siloxane and an "x” value (the mole percent of silicon atoms having at least one c 10 ⁇ c 20 alkyl group attached) of about 5 to about 15 mole percent of the copolymeric siloxane.
  • a still more preferred poly(dimethyl)-co- poly(methylalkyl) siloxane copolymer has a weight-average molecular weight of about 2,500 to about 3,500, a viscosity of about 25 to about 250 centipoise, a "w" value of about 90 mole percent, and an "x" value of about 10 mole percent.
  • the alkyl radicals (depicted as "A" in the above- presented formula) of these preferred poly(dimethyl)-co- poly(methylalkyl) siloxane copolymers include only even- numbered alkyl radicals; and such siloxane copolymers thus only have either 10, 12, 14, 16, 18, or 20 carbon atoms.
  • the poly(dimethyl)-co-poly(methyl, oxygen-containing) siloxane copolymer of this invention has the general formula CH 3 CH 3 B CH 3
  • a more preferred poly(dimethyl)-co-poly(methyl, oxygen- containing) siloxane copolymer has a viscosity of about 20 to about 110 centipoise, a "y” value (the mole percent of silicon atoms having dimethyl groups attached) of about 85 to 95 mole percent of the copolymeric siloxane, and a "z” value (the mole percent of silicon atoms having a methyl and an oxygen-containing group attached) of about 5 to 15 mole percent of the copolymeric siloxane.
  • a still more preferred poly(dimethyl)-co-poly(methyl, oxygen-containing) siloxane copolymer has a weight-average molecular weight of about 3,000 to about 3,500, and a viscosity of about 20 to about 100 centipoise.
  • Such preferred copolymeric siloxanes moreover, have an "R" value of either -CH 3 or -C 2 H 5 .
  • Specific examples of still other, particularly preferred poly(dimethyl)-co-poly(methyl, oxygen-containing) siloxane copolymers are described in the below-discussed examples.
  • the copolymeric siloxanes of the present invention are employed in amounts ranging from about 0.5 to about 50 weight percent, based upon the total weight of a specified composition (exclusive of any propellant) , with concentrations of about 1 to about 10 weight percent being preferred, and with concentrations of about 1 to about 5 weight percent being even more preferred.
  • copolymeric siloxane utilized in such a specified composition, is not critical. Indeed, those skilled in the art can well appreciate that specific copolymeric siloxane amounts will generally be dictated in accordance with the relative proportions of certain other ingredients which are included in a particular composition.
  • the emulsion polish compositions of the present invention can be either oil-in-water (i.e. so-called “water out”) emulsions or water-in-oil (i.e. so-called “oil out”) emulsions.
  • water out oil-in-water
  • water-in-oil water-in-oil
  • surfactant or emulsifier
  • combination of surfactants or emulsifiers
  • emulsion is generally recognized as connoting a stable mixture of two or more mutually immiscible liquids held in suspension by small percentages of substances called emulsifiers (or surfactants) . All emulsions, moreover, are characterized as comprising a continuous phase and a discontinuous phase which is dispersed throughout the continuous phase.
  • the hydrocarbon solvents and surfactants described below are typically those conventionally used in furniture polish compositions.
  • any solvents that are utilized in preparing the emulsion polish compositions of this invention should be sufficiently volatile so as to bring about rapid drying after the composition has been applied to a substrate surface, and yet, not so volatile as to prematurely dry up before desired spreading of the composition onto the substrate surface (for purposes of providing a desired film) has taken place.
  • those solvents deemed particularly useful, in accordance with the principles of our present invention have so-called "kauri-butanol" values of from about 20 to about 50, and have boiling-point ranges of from about 60° to about 210°C, and preferably from about 95° to about 150°C.
  • isoparaffinic hydrocarbon solvents such as those commercially available from the Exxon Corporation under the "Isopar” brand as well as the isoparaffinic-type hydrocarbon solvents commercially available from the Phillips Petroleum Corporation under the “Soltrols” brand, are moreover presently preferred because they are substantially odor-free.
  • Suitable hydrocarbon solvents include hexane, heptane and the so-called “Stoddard" solvents.
  • hydrocarbon solvent can be present in amounts of from about 0.15 to about 90 weight percent, based on the total weight of the emulsion polish composition (excluding any propellant, if present) .
  • the hydrocarbon solvent will be present in an amount of from about 1.0 to about 25 percent, with about 5 to about 20 weight percent being even more preferred.
  • emulsions comprise a continuous phase and a discontinuous phase. While the amount of surfactant (or emulsifier) present in the emulsion polish compositions of our present invention is not critical, it is to be understood that such emulsion polish compositions must include an amount of surfactant (or emulsifier) , or an amount of combinations of surfactants (or emulsifiers) , for effectively dispersing the discontinuous phase throughout the continuous phase.
  • non-ionic surfactants as well as certain combinations of conventional non-ionic surfactants, are utilized because they provide desirable emulsion- stability properties.
  • Conventional non-ionic surfactants (or emulsifiers) suitable for purposes of the present invention, include, but are not limited to, the so-called "sorbitan” esters of oleic and lauric acids; those polyethoxylated sorbitan esters having up to 20 ethoxy units; the monoglycerides and diglycerides of the fat-forming fatty acids; and combinations thereof.
  • non-ionic surfactants include certain "Span” brand and “Tween” brand emulsifiers, both presently available from ICI Americas, Inc.; and the "Monamid” brand emulsifiers, presently available from Mona Industries, Inc.
  • Particular examples of such emulsifiers include sorbitan monooleate, sold by ICI Americas, Inc., under the "SPAN 80" brand; sorbitan monolaurate, sold by ICI Americas, Inc., under the "SPAN 20” brand; and sorbitan monopaImitate, sold by ICI Americas, Inc., under the "SPAN 40” brand.
  • Mixtures of the various above-mentioned surfactants (or emulsifiers) can also be utilized, if desired, in accordance with the principles of our present invention.
  • quaternary ammonium compounds such as the quaternary ammonium halides, the quaternary ammonium sulfates, those so-called "fatty" amines which are ethoxylated and have about 2 to about 10 moles of ethylene oxide, and the chloride salts or acetate salts of amines, as well as those amines which are ethoxylated and have 2 or more moles of ethylene oxide.
  • Mixtures of the above surfactants (or emulsifiers) can also be utilized by those skilled in the art, in accordance with the principles of our invention, if desired.
  • anionic surfactants or emulsifiers suitable for purposes of our present invention, include certain sulfates (such as sodium lauryl sulfate and the sodium alkyl ether sulfates) , those sulfosuccinates containing polyethylene glycol moieties attached thereto, and the alkyl aryl sulfonates. Mixtures of the above surfactants (or emulsifiers) can also be utilized, in accordance with the principles of our present invention, if desired.
  • the surfactants (or emulsifiers) , mentioned above, while not critical, can thus be present in the compositions of our present invention in amounts ranging from about 0.1 to about 10 weight percent, based on the total weight of our emulsion polish composition (exclusive of any propellant, if present) , with from about 0.2 to about 1.2 weight percent being preferred.
  • the emulsion polish compositions of this invention also contain water as the principal constituent of the emulsion.
  • the presence of water in the emulsion polish composition of our invention has been observed to assist in the "leveling" of the resultant film of the emulsion polish composition, upon application of such a film to a substrate surface.
  • the presence of water moreover, tends to remove any water- soluble soil particles that may be present on the thus- treated substrate surface.
  • water will therefore make up the balance of the emulsion polish composition, taking into account the active ingredients noted above; and such balance amount of water is accordingly present in an amount ranging from about 2 to about 99 weight percent, based upon the total weight of the composition (exclusive of any propellant, if present) , with concentrations of about 66 to about 93 weight percent being preferred.
  • the most preferred emulsion polish compositions of this invention are totally wax-free. However, it may be desirable, in certain situations, to utilize a relatively minor amount of wax in specific formulations. Thus, from about 0.1 to about 0.5 weight-percent wax, based upon total weight of the emulsion polish composition, may be employed in the furniture polish compositions of the present invention.
  • Conventional waxes, suitable for purposes of our invention accordingly include, but are not limited to, certain synthetic waxes such as the microcrystalline waxes and the petroleum waxes as well as certain natural waxes such as the candellila and the carnauba waxes.
  • perfumes and preservatives may be added to the emulsion polish compositions of our present invention.
  • Perfumes are typically added, for example, to impart a desired fragrance.
  • Conventional perfumes, suitable for purposes of the present invention are well known to those skilled in the art and accordingly need not be described in detail here.
  • the amount of perfume which is included is typically present in an amount that is effective for imparting a desired fragrance intensity.
  • Such an amount of perfume can range, for example, from about 0.05 to about 1 weight percent, based upon the total weight of the emulsion polish composition (exclusive of any propellant, if present) .
  • Preservatives typically formaldehyde
  • Preservatives are generally utilized to retard or otherwise thwart undesired bacterial activity within packages containing certain formulations of the emulsion polish compositions of the present invention.
  • the presence of such preservatives is for prolonging the shelf life of the thus-formulated emulsion polish composition product.
  • a variety of well-known conventional quaternary compounds can moreover be utilized for such a purpose.
  • the emulsion polish compositions of the present invention can be applied directly onto a substrate surface, utilizing e.g. a wide variety of well-known conventional pressurized systems containing an appropriate amount of a liquid or gaseous propellant.
  • the emulsion polish compositions can be applied directly onto a substrate surface, utilizing well-known spray means such as conventional pump sprayers. Additionally, the emulsion polish compositions can be applied to furniture surfaces, utilizing a polishing cloth, or other suitable means.
  • the emulsion polish compositions of our present invention can be provided in aerosol form, depending upon the particular copolymeric siloxane compound or compound mixture which is utilized in the emulsion polish composition.
  • the emulsion polish composition (containing such an appropriate copolymeric siloxane compound or compound mixture) is introduced into a conventional aerosol container which is then capped with an aerosol valve.
  • an effective amount of a suitable, conventional propellant is introduced into the aerosol container, in a known manner, for achieving a desired pressure in the container.
  • propellant pressure should therefore be sufficient for enabling substantially complete expulsion of the aerosol container-contained ingredients, in the form of a spray in the desired manner, through the aerosol valve.
  • any of a wide variety of suitable conventional propellants which may be used include such well- known liquified hydrocarbons propellant gases as isobutane, n-butane and propane, and such well-known halogenated hydrocarbons as difluoroethane and the "Freon" brand of propellants, sold by E. I. Du Pont de Nemours & Co. Mixtures of halogenated hydrocarbons and other hydrocarbons may also be used in accordance with the principles of the present invention, if desired.
  • the aerosol emulsion polish compositions of this invention typically contain between about 5 and about 30 weight percent of propellant, based upon the total weight of the aerosol-containing emulsion polish composition of the present invention. The weight percentage or concentration of propellant is not critical and thus can vary widely depending on the desired end use.
  • the precise method of manufacturing the polish compositions of this invention is not critical.
  • the order and/or manner of addition of the various emulsion polish composition ingredients, mentioned above, may accordingly generally be varied and typically will not affect the quality of a particular emulsion polish composition which is thus being formulated or produced.
  • Conventional techniques for forming water-in-oil and oil-in-water emulsion polishes are typically used to produce the various embodiments of the emulsion polish compositions of the present invention.
  • the so-called "wax-free” emulsion polish composition embodiments of the present invention are prepared utilizing a known, so-called “cold-blend” process.
  • One conventional cold-blend processing method comprises charging the oil-phase ingredients (namely, the hydrocarbon solvent, the polysiloxane, the surfactant, and fragrance, if present) into a vessel of suitable dimension, preferably equipped with agitation means, and thereafter mixing the oil-phase ingredients until a homogeneous blend is achieved. Water and any other aqueous-phase ingredients (e.g. preservative) are next slowly added to the vessel, while maintaining a moderate degree or amount of agitation, to thereby produce the emulsion polish composition.
  • the oil-phase ingredients namely, the hydrocarbon solvent, the polysiloxane, the surfactant, and fragrance, if present
  • Water and any other aqueous-phase ingredients e.g. preservative
  • the resulting composition can then e.g. be homogenized by passing such emulsion polish composition through a 3/64 inch diameter orifice, utilizing a 60 to 80 psig pressure drop across the orifice.
  • Wax if a component of the emulsion polish composition of the present invention, is added with the initial oil-phase ingredients; and the resultant mixture is then heated to a temperature sufficient to melt the wax and achieve a homogeneous mixture. After the addition of water and any other ingredients, the wax-containing composition is either cooled or allowed to cool to room temperature (i.e. 25°C) and is preferably thereafter homogenized. Still other aspects, advantages and features of the present invention will become apparent upon reviewing the following examples, which are illustrative and not intended to limit the scope of the present invention except as defined in the appended claims.
  • Typical emulsion polish compositions of the present invention include:
  • the other surfactant utilized was TWEEN 80 brand surfactant.
  • copolymeric siloxanes that can be utilized in the formulation presented in Table 1 include poly(dimethyl)-co- poly(methylalkyl) siloxanes having a weight-average molecular weight of about 2,500 to about 4,000, a viscosity of about 20 to about 200 centipoise, and an "x" value (the mole percentage of silicon atoms having at least one C*LO ⁇ C 20 alkyl group attached thereto) of about 9 to about 30 mole percent.
  • the poly(dimethyl)-co-poly(methyl, oxygen-containing) siloxane utilized was a poly (91 mole-percent) dimethyl- co-poly (9 mole-percent) methyl thoxyethyoxyethylundecanoatyl siloxane, having a weight-average molecular weight of 3224.
  • One surfactant utilized, the sorbitan monooleate, was SPAN 80 brand surfactant.
  • the other surfactant utilized, the polyoxyethylene 20 sorbitan monooleate was TWEEN 80 brand surfactant.
  • the isoparaffinic hydrocarbon utilized was Isopar C brand isoparaffinic hydrocarbon, having a flash point of 40°F.
  • the copolymeric siloxanes that can be utilized in the formulation presented in Table 2 include poly(dimethyl)-co- poly(methyl, oxygen-containing) siloxane copolymers having weight-average molecular weights of about 1,000 to about 4,000, viscosities of about 10 to about 250 centipoise, and a "z" value (the mole percentage of silicon atoms having at least one methyl and oxygen-containing group attached thereto) of about 8 to 38 mole percent.
  • Comparative-Testing Examples To demonstrate the superior smear-recovery properties of emulsion polish compositions obtained from utilizing the copolymeric siloxanes of the present invention, certain comparative smear-recovery tests were performed. The results of these comparative smear-recovery tests clearly show the relative decrease in smear recovery time provided by the copolymeric siloxanes of the present invention, as compared to conventional siloxanes.
  • the comparative smear-recovery tests were conducted utilizing a Murakami brand Goniophotometer, specially outfitted with a solenoid-driven, spring-loaded swing arm. Parallel strands of either 220 micron or 320-325 micron diameter commercially-available monofilament fibers were utilized as the smear-causing medium. Fifteen-degree incident-specular reflectance of each substrate-applied film was monitored as a function of time-after-smearing. The films were cast on conventional 2.25 inch square nitrocellulose lacquer-coated glass slides. The backs of the glass slides were coated with black lacquer to prevent reflection from the back face of these glass slides. Percent smear recovery was measured as the percent specular reflectance, as compared to the specular reflectance before the film was smeared. Procedure for Determining Smear Recovery
  • a Murakami brand, model GP-1R, commercially-available Goniophotometer, specifically outfitted with a solenoid- driven swing arm was utilized. Attached to the swing arm was a 3/4 inch-wide smear medium.
  • the smear medium consisted of a plurality of contacting, parallel strands of either 220 or 300-to-325 micron-diameter commercially-available monofilament line. Each such strand comprised an elongated, generally linear portion and a unitary, generally "C"-shaped portion at one end of the linear strand.
  • Each such monofilament line strand was generally disposed, relative to a test substrate coupon, such that the generally linear strand portion was generally perpendicular to the test substrate while the curved portion of the monofilament strand rested on the surface of the test substrate.
  • each such strand of the plurality was disposed such that the curved portion of each such filament came into contact with the substrate, thereby to assure substantially complete contact of the plural strands over the test substrate area being smeared.
  • Each test substrate consisted of a 2.25 inch by 2.25 inch square of 1/8 inch-thick pieces of clear glass having a refractive index of about 1.50 to 1.52. It is important, for this procedure, that the lacquer and the glass have refractive index values that are about the same.
  • Each such clear piece of glass moreover, was coated with 1.25 grams of high-gloss nitrocellulose-containing furniture lacquer. Such lacquer included about 21.3 wt.-% non-volatile material.
  • the glass-applied lacquer was cured slowly under a watch glass on a level surface, thereby to assure a smooth uniform finish on the piece of glass.
  • the back of each such glass test slide was thus coated with a black lacquer to eliminate reflection from that surface.
  • the lacquer-applied side of each such piece of glass had a refractive index of between 1.50 and
  • each test slide was inserted into the specimen holder of the Goniophotometer; and the 15 degree incident specular reflectance of the test surface was then measured directly.
  • the solenoid-driven arm was activated to smear the test film. Such smearing resulted in a decrease in specular reflection of the test film.
  • the specular reflectance of the film was monitored as a function of time to determine the amount of time that it took for the thus- disturbed film to recover to 95% of its original reflection.
  • Table 3 presents the time for 95% recovery of specular reflection for specific poly(dimethyl)-co- poly(methylalkyl) siloxane copolymers of the subject invention as well as for certain prior-art polydimethyl siloxanes which are being compared to the copolymeric siloxanes of the present invention.
  • Smear recovery is the amount of time, expressed in seconds, that is needed to recover to 95% of the original reflectance value.
  • the specular reflectance determination procedure, utilizing a 320 micron diameter smear pattern, is more particularly set forth in the above-noted procedure, j.
  • the prior-art polysiloxanes identified in Table 3 are similar to those polysiloxanes disclosed in Examples 1 and 4 of U.S. Pat. No. 2,523,281 to Currie and in Examples 5 through 7 of U.S. Pat. No. 2,698,805 to Currie et al. In such prior-art polysiloxanes, the "x" and "A" values listed in Table 3 are nonexistent.
  • Siloxane No. 1 is polydimethyl-co-polymethyldecyl siloxane copolymer.
  • Siloxane No. 2 is polydimethyl-co- polymethyldodecyl siloxane copolymer.
  • Siloxane No. 3 is polydimethyl-co-polymethyl tetradecyl siloxane copolymer.
  • Siloxane No. 4 is polydimethyl-co-polymethylhexadecyl siloxane copolymer.
  • Siloxane No. 5 is polydimethyl-co- polymethyloctadecyl siloxane copolymer.
  • Siloxane No. 7 is polydimethyl-co-polymethyltetradecyl siloxane copolymer.
  • Siloxanes "A" and "B", both prior-art compounds, are polydimethyl siloxane polymers. The results, as shown in Table 3 above demonstrate that, at comparable molecular weights, the smear-recovery properties of the poly(dimethyl)-co-poly(methylalkyl) siloxane copolymers of this invention are superior to the prior-art polydimethyl siloxanes.
  • compositions of the present invention recover to 95% of their initial specular reflectance in 5 seconds or less, as compared to the prior-art dimethyl siloxane-containing compositions which require 20 to 30 seconds.
  • the poly(dimethyl)-co-poly(methylalkyl) siloxane copolymers listed in Table 3 were prepared from commercially- available polydimethyl-co-polymethylhydrosiloxane precursors and commercially-available alpha-olefins, utilizing a well- known hydrosilylation reaction. More specifically, synthesis of the siloxane copolymers was performed by the well-known hydrosilylation reaction of polydimethyl-co-polymethylhydrosiloxane (available either from Petrarch System, Inc.
  • alpha-olefins of varying lengths (available from Aldrich) .
  • a round-bottomed flask equipped with magnetic stirring bar, condenser and calcium-chloride tube was charged with a 50 wt.-% solution of the reactants (up to 10% molar excess alpha-olefin) in dry toluene.
  • a solution of hydrogen hexachloroplatinate (IV) in digly e/isopropanol was then added to the reaction mixture (150 ppm Pt) .
  • the reaction mixture was then stirred at 60°C for three hours. At the end of this reaction period, the resultant mixture was refluxed with activated charcoal for 1 hour, and filtered hot.
  • the reactants that were utilized to prepare the siloxanes presented in Table 3 are as follows.
  • the hydrosiloxane precursor was poly(90%)dimethyl-co-poly(10%)methylhydrosiloxane, and the alpha-olefin was 1-decene.
  • the hydrosiloxane precursor was poly(90%)dimethyl-co- poly(10%)methylhydrosiloxane, and the alpha-olefin was 1- dodecene.
  • the hydrosiloxane precursor was poly(90%)dimethyl-co- poly(10%)methylhydrosiloxane, and the alpha-olefin was 1- tetradecene.
  • the hydrosiloxane precursor was poly(90%)dimethyl-co- poly(10%)methylhydrosiloxane, and the alpha-olefin was 1- hexadecene.
  • the hydrosiloxane precursor was poly(90%)dimethyl-co- poly(10%)methylhydrosiloxane, and the alpha-olefin was 1- octadecene.
  • the hydrosiloxane precursor was poly(90%)dimethyl-co- poly(10%)methylhydrosiloxane, and the alpha-olefin was 1- eicosene.
  • the hydrosiloxane precursor was poly(70%)dimethyl-co- poly(30%)methylhydrosiloxane, and the alpha-olefin was 1- tetradecene.
  • Table 4 presents the amount of time that is necessary to achieve a 95% recovery of specular reflection, for those emulsion polish compositions made from specified poly(dimethyl)-co-poly(methyl, oxygen-containing) siloxane copolymers of the present invention, in comparison to specular reflection recovery times of certain emulsion polish compositions made from specific prior-art polydimethyl siloxanes.
  • Smear recovery is the amount of time, expressed in seconds, that is needed to recover to 95% of the original reflectance value.
  • the specular reflectance determination procedure, utilizing a 220 micron diameter smear pattern, is more particularly set forth in the above-noted procedure. 1.
  • the prior-art polysiloxane identified in Table 4 is similar to those polysiloxanes disclosed in Examples 1 and 4 of U.S. Pat. No.
  • Siloxane No. 8 is polydimethyl-co- polymethylethylundecanoatyl siloxane copolymer.
  • Siloxane No. 9 is polydimethyl-co-polymethylmethoxyethylundecanoatyl siloxane copolymer.
  • Siloxane No. 10 is polydimethyl-co- polymethyl ethoxyethoxyethylundecanoatyl siloxane copolymer.
  • Siloxane No. 11 is polydimethyl-co- polymethylethoxyethoxyethoxyethylundecanoatyl siloxane copolymer.
  • Siloxane No. 12 is polydimethyl-co- polymethylethylundecanoatyl siloxane copolymer.
  • Siloxane No. 13 is polydimethyl-co-polymethylmethoxyethylundecanoatyl siloxane copolyme ' r.
  • Siloxane No. 14 is polydimethyl-co- polymethylethoxyethoxyethylundecanoatyl siloxane copolymer.
  • Siloxane No. 15 is polydimethyl-co- polymethylethoxyethoxyethoxyethylundecanoatyl siloxane copolymer.
  • Siloxane "C" a prior-art compound, is polydimethyl siloxane polymer.
  • Siloxane No. 8 was produced from poly(92%)dimethyl-co- poly(8%)methylhydrosiloxane and the oxygen-containing compound referred to as ethyl undecenoate, where one well- known procedure for producing this type of oxygen-containing compound is set forth in Vogel's Textbook of Practical Organic Chemistry, 4th ed, , published 1981, at page 512.
  • Siloxane No. 9 was produced from poly(92%)dimethyl-co- poly(8%)methylhydrosiloxane and the oxygen-containing compound referred to as methoxyethylundecenoate, where one well-known procedure for producing this type of oxygen- containing compound is set forth in the above-cited Vogel text.
  • Siloxane No. 12 was produced from poly(90%)dimethyl-co-poly(10%)methylhydrosiloxane and ethylundecenoate.
  • Siloxane No. 13 was produced from poly(90%)dimethyl-co-poly(10%)methylhydrosiloxane and methoxyethylundecenoate.
  • Siloxane No. 14 was produced from poly(90%)dimethyl-co-poly(10%)methylhydrosiloxane and ethoxyethoxyethylundecenoate.
  • Siloxane No. 15 was produced from poly(90%)dimethyl-co-poly(10%)methylhydrosiloxane and ethoxyethoxyethoxyeth lundecenoate.
  • Table 5 presents the amount of time that is necessary to achieve a 95% recovery of specular reflection, for those emulsion polish compositions made from other specified pol (dimethyl)-co-poly(methyl, oxygen-containing) siloxane copolymers of the present invention, in comparison to specular reflection recovery times of certain emulsion polish compositions made from specific prior-art polydimethyl siloxanes.
  • the pol (dimethyl)-co-poly(methyl, oxygen-containing) siloxanes listed in Table 5 as Siloxane Nos. 16 and 17, each had the -O- moiety as its "L” value and the -CH 3 radical as its "R” value.
  • Smear recovery is the amount of time, expressed in seconds, that is needed to recover to 95% of the original reflectance value.
  • the specular reflectance determination procedure utilizing a 320 micron diameter smear pattern, is more particularly set forth in the above-noted procedure.
  • n The prior-art polysiloxanes identified in Table 5 are similar to those polysiloxanes disclosed in Examples 1 and 4 of U.S. Pat. No. 2,523,281 to Currie and in Examples 5 through 7 of U.S. Pat. No. 2,698,805 to Currie et al. In such prior-art polysiloxanes, and in those prior-art compounds presented in Table 5 as Siloxanes "D” and "E", the "R", “L”, “z”, "n” and “i” values are nonexistent.
  • Siloxane No. 16 polydimethyl-co- polymethylmethoxyethoxypropylsiloxane, was produced from poly(88%)dimethyl-co-poly(12%)methylhydrosiloxane and the oxygen-containing compound referred to as methoxyethoxyallyl, where one well-known procedure for producing this oxygen- containing compound is set forth in U.S. Pat. No. 4,260,725 to Keogh and Kinzler. Siloxane No.
  • the weight-average molecular weight determinations of these copolymeric siloxanes were calculated, based on supplier literature and determined mole percentages of Si-H.
  • the viscosities of these copolymeric siloxanes were determined at 25°C, utilizing a Brookfield, model HBT-200, cone-and-plate viscometer, a Brookfield model LVT viscometer, or a Bohlin Rheometer. Most viscosities were determined at 20 rpm, when utilizing the Brookfield model HBT-200 viscometer.
  • copolymeric siloxanes were applied onto substrate surfaces by spincoating 5 wt.-% solutions of copolymeric siloxane in 2,2,4-trimethylpentane solvent, onto conventional 2.25 inch by 2.25 inch square nitrocellulose lacquer-coated test slides.
  • the spin-coating procedure utilized was to flood the surface with solution, and then to spin the slide at 500-2500 rpm while the solution dried. Conditions were varied to attain a desired thickness for comparison purposes (2000-4000 Angstroms) . Thickness was determined gravimetrically.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Compositions de vernis-émulsion comportant un siloxane copolymère sélectionné parmi le groupe constitué d'un polymère de siloxane poly(diméthyle)-co-poly(méthylalkyle), d'un polymère de siloxane poly(diméthyle)-co-poly(méthyle, oxygéné), et de leurs combinaisons. Le copolymère de siloxane poly(diméthyle)-co-poly(méthylalkyle) répond à la formule (I), dans laquelle A est un radical alkyle possédant de 10 à 20 atomes de carbone, w est compris entre 70 et 91 % en mol, et x est compris entre 9 et 30 % en mol. Le copolymère de siloxane poly(diméthyle)-co-poly(méthyle, oxygéné) répond à la formule (II), dans laquelle B est (CH2)i(L)(CH2CH2O)nR, i est un nombre entier compris entre 3 et 10, L est -O- ou -COO-, n est zéro ou un nombre entier compris entre 1 et 3, R est -H, -CH3, ou -C2H5, y est compris entre 62 et 92 % en mole, et z est compris entre 8 et 38 % en mole.
PCT/US1990/002542 1990-05-03 1990-05-03 Compositions filmogenes de vernis-emulsion contenant des siloxanes copolymeres WO1991017223A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA002081009A CA2081009C (fr) 1990-05-03 1990-05-03 Compositions de polissage en emulsion qui forme une pellicule, et contenant des siloxanes polymeriques
EP19900907957 EP0527124A4 (en) 1990-05-03 1990-05-03 Film-forming emulsion polish compositions containing copolymeric siloxanes
AU56307/90A AU644791B2 (en) 1990-05-03 1990-05-03 Film-forming emulsion polish compositions containing copolymeric siloxanes
PCT/US1990/002542 WO1991017223A1 (fr) 1990-05-03 1990-05-03 Compositions filmogenes de vernis-emulsion contenant des siloxanes copolymeres
JP90507265A JPH05508171A (ja) 1990-05-03 1990-05-03 コーポリマーシロキサンを含有する膜形成エマルジョンつや出し組成物

Applications Claiming Priority (2)

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CA002081009A CA2081009C (fr) 1990-05-03 1990-05-03 Compositions de polissage en emulsion qui forme une pellicule, et contenant des siloxanes polymeriques
PCT/US1990/002542 WO1991017223A1 (fr) 1990-05-03 1990-05-03 Compositions filmogenes de vernis-emulsion contenant des siloxanes copolymeres

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
EP0536280A1 (fr) * 1990-06-25 1993-04-14 S.C. JOHNSON & SON, INC. Formulations et concentres d'encaustique pour les meubles

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US5174813A (en) * 1991-11-07 1992-12-29 Dow Corning Corporation Polish containing derivatized amine functional organosilicon compounds

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US2770631A (en) * 1954-05-20 1956-11-13 Dow Corning Hydroxyester substituted siloxanes
US2953047A (en) * 1959-01-08 1960-09-20 Fraser Kenneth G Spinning tool
CA746973A (en) * 1966-11-22 S. Pater Anton Aqueous emulsion of organopolysiloxane mixtures
US3929492A (en) * 1971-11-26 1975-12-30 Johnson & Son Inc S C Surface treating compositions

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US3960574A (en) * 1974-05-13 1976-06-01 Dow Corning Corporation Detergent resistant auto polish

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Publication number Priority date Publication date Assignee Title
CA746973A (en) * 1966-11-22 S. Pater Anton Aqueous emulsion of organopolysiloxane mixtures
US2770631A (en) * 1954-05-20 1956-11-13 Dow Corning Hydroxyester substituted siloxanes
US2953047A (en) * 1959-01-08 1960-09-20 Fraser Kenneth G Spinning tool
US3929492A (en) * 1971-11-26 1975-12-30 Johnson & Son Inc S C Surface treating compositions

Non-Patent Citations (1)

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Title
See also references of EP0527124A4 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0536280A1 (fr) * 1990-06-25 1993-04-14 S.C. JOHNSON & SON, INC. Formulations et concentres d'encaustique pour les meubles
EP0536280A4 (en) * 1990-06-25 1993-05-26 S.C. Johnson & Son, Inc. Furniture polish concentrate and formulations

Also Published As

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EP0527124A1 (fr) 1993-02-17
EP0527124A4 (en) 1993-06-23
AU5630790A (en) 1991-11-27
AU644791B2 (en) 1993-12-23

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