US3075228A - Anti-fogging article - Google Patents

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US3075228A
US3075228A US716848A US71684858A US3075228A US 3075228 A US3075228 A US 3075228A US 716848 A US716848 A US 716848A US 71684858 A US71684858 A US 71684858A US 3075228 A US3075228 A US 3075228A
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fibrous material
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    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/32—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with synthetic or natural resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces

Definitions

  • the present invention relates to a new article of manufacture adaptable for cleaning and treating smooth glasslike surfaces, a process of making the article and a method of treating glass, plastic or polished surfaces therewith.
  • fibrous material be impregnated with certain sulfated aliphatic hydrocarbons for the purpose of providing an article which may be used for polishing and inhibiting fog formation on glass and the like.
  • Polyhydroxy alcohols that have been partially esterified with higher fatty acids have also been suggested for somewhat similar purposes.
  • These materials exhibit certain disadvantages which have limited their usefulness. Thus, these agents are held too tenaciously in the fibrous materials, so that there is difficulty in transferring them to the glass surface. It has now been found that these disadvantages may be overcome through the use of a composition comprising at least one salt of sulfated alkyl aryloxypolyalkoxy alcohol. It has further been found that the feel of the impregnated fibrous material is considerably improved through the use of said composition.
  • fibrous material is impregnated with a composition containing at least one compound of formula wherein n is an integer preferably from 8 to 100; R is an alkyl radical, and preferably higher alkyl radical; R is a divalent saturated alkylene radical having at least 2 carbon atoms preferably lower alkylene; Me is a metal or metalloid cation, and preferably alkali metal.
  • R may be an alkyl radical having from 1 to 30 carbon atoms and preferably from 8 to 32 carbon atoms.
  • R may be methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, Z-ethylhexyl, octyl, nonyl, decyl, hendecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, eicosyl and dotriacontyl.
  • R may be a divalent saturated alkylene radical having preferably from 2 to 3 carbon atoms and including ethylene and propylene, or mixtures of both in the polyglycol chain.
  • Me in Formula 1 above may be an alkali metal, such as sodium, potassium or lithium.
  • R is octyl, or nonyl
  • R' is ethylene, i.e., CH CH
  • Me is sodium.
  • the groups bonded to the benzene ring in Formula 1 are in the para position to each other.
  • the combination of a' substantial percentage of a compound of Formula 1, which is solid at room temperature, and a flexible Web-like fabric such as paper, felt and textile produces an article highly useful for cleaning and defogging glass surfaces.
  • the compounds are solid in the ordinary temperature range between 15 and 45 C., and are Water soluble.
  • the solubility is suificient so that a trace of moisture, such as is usually present as an adsorbed film on glass or plastic surfaces, is suflicient to dissolve a minute amount of said compounds from the cloth and leave it as an invisible film on the glass surface.
  • the compounds of Formula 1 do not easily form insoluble precipitates or residues with impurities generally present in water such as calcium, iron, etc. Nor is the trace of material left on the glass or transparent plastic which may be only one or two microns thick, opaque or interfere with the passage of light.
  • the proportion of Compound 1 described above which may be incorporated into a fabric to make it useful for the purposes of the present invention, may range from a low of about 3% of the original weight of the fabric up to or even more. I have found that proportions less than 3% based on the original weight of the textile are not effective because the textile retains such material by adsorption and does not release it to the glass or other surface early enough to be properly effective.
  • any salt of a sulfated alkyl aryloxypolyalkoxy alcohol, as defined herein, or any mixture of such compounds may be advantageously employed.
  • nonionic wetting agents that may be mentioned are the mono methyl, ethyl, propyl or decyl ethers of high molecular weight polyglycols.
  • monoesters of polyglycols may be added. These include, for example, polyethylene or polypropylene glycol-mono laurate, -mono oleate, -mono stearate, -mono ricinoleate, etc.
  • Surface Active Agents by Schwartz & Perry, pages 202-214.
  • the cationic surface active agents are definitely useless for antifogging, since they actually promote fogging on glass or plastic.
  • a useful composition in combination with the compounds of Formula 1 includes a small quantity of a sodium alkyl sulfate, such as sodium lauryl sulfate.
  • other anionic materials in small quantities may be used in conjunction with compounds of Formula 1. These include the alkali salts of naphthenyl sulfate, e.g., the sodium sulfonate of polypropylnaphthalene (sold under the trade names of Akanol B, Nekol A, etc.). These are examples of the aralkylsulfates that may be used in conjunction with the compounds of Formula 1.
  • the sodium salt of kerylbenzene sulfonate (sold under the trade names of Nae: conal NRSF, etc.), may similarly be used.
  • the sodium salt of the sulfated octyl iil I phenoxypolyethoxy ethanol of the examples below is prepared by the sulfation and neutralization with sodium hydroxide of octyl phenoxypolyethoxyethanol prepared by the reaction of 9 moles of ethyleneoxide with 1 mole of p-octylphenol.
  • the monomethyl ether of polyglycol mentioned in the examples is prepared by the reaction of 1 mole of a methylhalide with 1 mole of monosodium polyethylene glycolate of molecular weight 400.
  • the sodium salt of the sulfated nonyl phenoxypolyethoxyethanol employed in the following examples is prepared in the same way as the octyl compound except that moles of ethylene oxide are reacted with 1 mole of p-nonylphenol, the product then being sulfated and neutralized. Unless otherwise specified, the percentages given are by weight.
  • Example 1 A 28% solution of the sodium salt of sulfated octyl phenoxypolyethoxyethanol in a mixture of water and ethyl alcohol in the ratio of 80 parts by volume of H 0 to 20 parts by volume of ethyl alcohol is prepared and the cotton cloth impregnated and calendered, so that on drying 20% solids are'left in the cloth. The cloth is found to be an excellent antifogging cloth.
  • Example 2 A solution is formed in a water-isopropyl alcohol mixture containing 85 parts by volume of R 0 to parts of isopropyl alcohol of 25% of the sulfated sodium salt of octyl phenoxypolyethoxyethanol and 3% of a monomethyl ether of polyglycol having a melting point of 45 C.
  • the cotton cloth is impregnated and then put through a calender and dried so that solids remain in the cloth.
  • Example 3 The procedure of Example 1 is followed, excepting that the impregnating solution contains by weight of the sodium salt of sulfated octyl phenoxypolyethoxyethanol and 3% by weight of the lauric acid ester of a polyethylene glycol having an average molecular weight of 4000.
  • Example 5 The procedure of Example 1 is followed excepting that the impregnating solution contains 25% by weight of the sodium salt of sulfated nonyl phenoxypolyethoxyethanol and 3% by weight of naphthenic acid ester of a polyethylene glycol having an average molecular weight of 4000.
  • Example 6 The procedure of Example 1 is followed, excepting that the impregnating solution contains 25% by weight of the sodium salt of sulfated octyl phenoxypolyethoxy ethanol and 3% by weight of the dodecyl monoetlier of a polyethylene glycol having an average molecular weight of 4000.
  • Example 7 The procedure of Example 1 is followed, excepting that the impregnating solution contains 25% by weight of the sodium salt of sulfated octyl phenoxypolyethoxyethanol and 3% by weight of the nonylphenyl monoether of a polyethylene glycol having an average molecular weight of 4000.
  • Example 8 The procedure of Example 1 is followed, excepting that the impregnating solution contains 14% by weight of the sodium salt of sulfated octyl phenoxypolyethoxyethanol and 14% by weight of the sodium salt of sulfated nonyl phenoxypolyethoxyethanol.
  • a method of making a paper impregnated with antifogging material comprises suspending the wood pulp or other cellulose fibres constituting the basic ingredient of the paper, in a solution of the antifogging material having a concentration sufiicient to incorporate the desired proportion of antifogging material in the paper, when the paper is formed and dried.
  • An article of manufacture according to claim 10 having incorporated therein as a secondary wetting agent a monomethyl ether of a polyglycol having a melting point of about 45 C.
  • An article of manufacture according to claim 10 having incorporated therein as a secondary wetting agent a sodium lauryl sulfate and the monomethylether of polyglycol having a melting point of 45 C.
  • An article of manufacture according to claim 10 having incorporated therein as a secondary wetting agent the lauric acid ester of a polyethylene glycol having an average molecular weight of 4000.
  • An article of manufacture according to claim 10 having incorporated therein as a secondary wetting agent the nonylphenyl monoether of a polyethylene glycol having an average molecular weight of 4000.
  • a process according to claim 7 wherein said salt is an alkali metal salt of a sulfated alkyl aryloxypolyalkoxy alcohol.
  • weight of said alkali metal salt based on the weight of said fibrous material is incorporated in the latter.

Description

3,975,228 Patented Jan. 29, 1963 ice 3,075,228 ANT'i-FOGGING ARTICLE Nathaniel M. Elias, 56 Washington Mews, New York, N.Y. No Drawing. Filed Feb. 24, 1958, Ser. No. 716,848 9 Claims. (Cl. 15-506) The present invention relates to a new article of manufacture adaptable for cleaning and treating smooth glasslike surfaces, a process of making the article and a method of treating glass, plastic or polished surfaces therewith.
This is a continuation-in-part of application Serial No. 354,432, now abandoned.
It has been suggested in the prior art that fibrous material be impregnated with certain sulfated aliphatic hydrocarbons for the purpose of providing an article which may be used for polishing and inhibiting fog formation on glass and the like. Polyhydroxy alcohols that have been partially esterified with higher fatty acids have also been suggested for somewhat similar purposes. These materials, however, exhibit certain disadvantages which have limited their usefulness. Thus, these agents are held too tenaciously in the fibrous materials, so that there is difficulty in transferring them to the glass surface. It has now been found that these disadvantages may be overcome through the use of a composition comprising at least one salt of sulfated alkyl aryloxypolyalkoxy alcohol. It has further been found that the feel of the impregnated fibrous material is considerably improved through the use of said composition.
a In accordance with the present invention fibrous material is impregnated with a composition containing at least one compound of formula wherein n is an integer preferably from 8 to 100; R is an alkyl radical, and preferably higher alkyl radical; R is a divalent saturated alkylene radical having at least 2 carbon atoms preferably lower alkylene; Me is a metal or metalloid cation, and preferably alkali metal. R may be an alkyl radical having from 1 to 30 carbon atoms and preferably from 8 to 32 carbon atoms. Thus, R may be methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, Z-ethylhexyl, octyl, nonyl, decyl, hendecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, eicosyl and dotriacontyl. R may be a divalent saturated alkylene radical having preferably from 2 to 3 carbon atoms and including ethylene and propylene, or mixtures of both in the polyglycol chain. Me in Formula 1 above may be an alkali metal, such as sodium, potassium or lithium. The best results are obtained with compounds wherein R is octyl, or nonyl; R' is ethylene, i.e., CH CH and Me is sodium. In the preferred form of this invention the groups bonded to the benzene ring in Formula 1 are in the para position to each other.
It has been found, in accordance with certain features, of the present invention, that the combination of a' substantial percentage of a compound of Formula 1, which is solid at room temperature, and a flexible Web-like fabric such as paper, felt and textile, produces an article highly useful for cleaning and defogging glass surfaces. The compounds are solid in the ordinary temperature range between 15 and 45 C., and are Water soluble. The solubility is suificient so that a trace of moisture, such as is usually present as an adsorbed film on glass or plastic surfaces, is suflicient to dissolve a minute amount of said compounds from the cloth and leave it as an invisible film on the glass surface.
The compounds of Formula 1 do not easily form insoluble precipitates or residues with impurities generally present in watersuch as calcium, iron, etc. Nor is the trace of material left on the glass or transparent plastic which may be only one or two microns thick, opaque or interfere with the passage of light.
It has been found, in accordance with the present invention, that unexpectedly, large amounts of the compounds of Formula 1, based on the weight of the fabric, can be incorporated into such fabric and will adhere and remain part of the resulting article. Moreover, the fabric will remain flexible, will be changed very little in appearance, and will be usable over a long period of time. Furthermore, it has been found that said compounds are readily transferred to the glass surface.
The proportion of Compound 1 described above which may be incorporated into a fabric to make it useful for the purposes of the present invention, may range from a low of about 3% of the original weight of the fabric up to or even more. I have found that proportions less than 3% based on the original weight of the textile are not effective because the textile retains such material by adsorption and does not release it to the glass or other surface early enough to be properly effective.
In accordance with the present invention, any salt of a sulfated alkyl aryloxypolyalkoxy alcohol, as defined herein, or any mixture of such compounds, may be advantageously employed. Thus, for example, the sodium salts of sulfated =octylphenoxy-polyethoxy ethanol or sulfated nonylphenoxypolyethoxy ethanol, either individually or in admixture, are excellent fogproofing agents.
It has also been found that in some cases, in addition to the compounds of Formula 1 above, it is desirable to add a small proportion of a nonionic wetting agent. Among the nonionic wetting agents that may be mentioned are the mono methyl, ethyl, propyl or decyl ethers of high molecular weight polyglycols. Similarly monoesters of polyglycols may be added. These include, for example, polyethylene or polypropylene glycol-mono laurate, -mono oleate, -mono stearate, -mono ricinoleate, etc. For additional nonionic wetting agents that are useful in the present invention, see Surface Active Agents" by Schwartz & Perry, pages 202-214. In contrast to this, the cationic surface active agents are definitely useless for antifogging, since they actually promote fogging on glass or plastic.
It has also been found that in combination with the compounds of Formula 1 a useful composition includes a small quantity of a sodium alkyl sulfate, such as sodium lauryl sulfate. In a similar manner, other anionic materials in small quantities may be used in conjunction with compounds of Formula 1. These include the alkali salts of naphthenyl sulfate, e.g., the sodium sulfonate of polypropylnaphthalene (sold under the trade names of Akanol B, Nekol A, etc.). These are examples of the aralkylsulfates that may be used in conjunction with the compounds of Formula 1. The sodium salt of kerylbenzene sulfonate (sold under the trade names of Nae: conal NRSF, etc.), may similarly be used.
When the principal antifiogging agent is used in con- The sodium salt of the sulfated octyl iil I phenoxypolyethoxy ethanol of the examples below is prepared by the sulfation and neutralization with sodium hydroxide of octyl phenoxypolyethoxyethanol prepared by the reaction of 9 moles of ethyleneoxide with 1 mole of p-octylphenol. The monomethyl ether of polyglycol mentioned in the examples is prepared by the reaction of 1 mole of a methylhalide with 1 mole of monosodium polyethylene glycolate of molecular weight 400. The sodium salt of the sulfated nonyl phenoxypolyethoxyethanol employed in the following examples is prepared in the same way as the octyl compound except that moles of ethylene oxide are reacted with 1 mole of p-nonylphenol, the product then being sulfated and neutralized. Unless otherwise specified, the percentages given are by weight.
. Example 1 A 28% solution of the sodium salt of sulfated octyl phenoxypolyethoxyethanol in a mixture of water and ethyl alcohol in the ratio of 80 parts by volume of H 0 to 20 parts by volume of ethyl alcohol is prepared and the cotton cloth impregnated and calendered, so that on drying 20% solids are'left in the cloth. The cloth is found to be an excellent antifogging cloth.
Example 2 A solution is formed in a water-isopropyl alcohol mixture containing 85 parts by volume of R 0 to parts of isopropyl alcohol of 25% of the sulfated sodium salt of octyl phenoxypolyethoxyethanol and 3% of a monomethyl ether of polyglycol having a melting point of 45 C. The cotton cloth is impregnated and then put through a calender and dried so that solids remain in the cloth.
Example 3 Example 4 The procedure of Example 1 is followed, excepting that the impregnating solution contains by weight of the sodium salt of sulfated octyl phenoxypolyethoxyethanol and 3% by weight of the lauric acid ester of a polyethylene glycol having an average molecular weight of 4000.
Example 5 The procedure of Example 1 is followed excepting that the impregnating solution contains 25% by weight of the sodium salt of sulfated nonyl phenoxypolyethoxyethanol and 3% by weight of naphthenic acid ester of a polyethylene glycol having an average molecular weight of 4000.
Example 6 The procedure of Example 1 is followed, excepting that the impregnating solution contains 25% by weight of the sodium salt of sulfated octyl phenoxypolyethoxy ethanol and 3% by weight of the dodecyl monoetlier of a polyethylene glycol having an average molecular weight of 4000.
' Example 7 The procedure of Example 1 is followed, excepting that the impregnating solution contains 25% by weight of the sodium salt of sulfated octyl phenoxypolyethoxyethanol and 3% by weight of the nonylphenyl monoether of a polyethylene glycol having an average molecular weight of 4000.
4 Example 8 The procedure of Example 1 is followed, excepting that the impregnating solution contains 14% by weight of the sodium salt of sulfated octyl phenoxypolyethoxyethanol and 14% by weight of the sodium salt of sulfated nonyl phenoxypolyethoxyethanol.
By using a more concentrated solution and by allowing more of the solution of the antifiogging agent to remain in the fabric before drying the soaked fabric, higher percentages of the antifogging agent may be incorporated.
A method of making a paper impregnated with antifogging material comprises suspending the wood pulp or other cellulose fibres constituting the basic ingredient of the paper, in a solution of the antifogging material having a concentration sufiicient to incorporate the desired proportion of antifogging material in the paper, when the paper is formed and dried.
While the invention has been described with particular reference to specific embodiments, it is to be understood that it is not to be limited thereto, but is to be construed broadly and restricted solely by the scope of the appended claims.
What is claimed is:
.1. As an article of manufacture useful in preventing the fogging of glass and the like, comprising a fibrous material having incorporated therein at least 3% by weight based on th original weight of said fibrous material of an alkali metal salt of sulfated alkyl aryloxypolyalkoxy alcohol.
2. The article according to claim '1 wherein said article contains in addition to said alkali metal salt a small quantity of a nonionic wetting agent.
3. The article according to claim 1 wherein said article comprises a mixture of alkali metal salts of sulfated alkyl aryloxypolyalkoxy alcohols.
4. The article according to claim 1 wherein said article contains in addition to said alkali metal salt a small quantity of an alkali metal alkylsulfate anionic wetting agent.
5.-A process for impregnating fibrous material in the preparation of an article useful in antifogging of glass and the like, which comprises contacting said fibrous material with a solution containing at least 3% by weight based on the original weight of said fibrous material of an alkali metal salt of a sulfatcd alkyl aryloxypolyalkoxy alcohol, calendering and drying said fibrous material wherein at least 20% of solids remain in said material and whereby said salt becomes incorporated in said fibrous material.
6. A process according to claim 5 wherein said solution is an aqueous solution.
7. A process according to claim 6 wherein said solution is an aqueous alcoholic solution.
8. A process according to claim 7 wherein the impregnated fibrous material is put through a calender and then dried.
9. An article of manufacture according to claim 1 wherein from 3% to by weight of said alkali metal salt, based on the weight of said fibrous material, is incorporated in the latter.
10. An article of manufacture according to claim 9 wherein said salt is the sodium salt of sulfated octyl phenoxypolyethoxyethanol.
11. An article of manufacture according to claim 10 having incorporated therein as a secondary wetting agent a monomethyl ether of a polyglycol having a melting point of about 45 C.
12. An article of manufacture according to claim 10 having incorporated therein as a secondary wetting agent a sodium lauryl sulfate and the monomethylether of polyglycol having a melting point of 45 C.
13. An article of manufacture according to claim 10 having incorporated therein as a secondary wetting agent the lauric acid ester of a polyethylene glycol having an average molecular weight of 4000.
an average molecular weight of 4000.
15. An article of manufacture according to claim 10 having incorporated therein as a secondary wetting agent the nonylphenyl monoether of a polyethylene glycol having an average molecular weight of 4000.
16. An article of manufacture according to claim 9 wherein said salt is a sodium salt of sulfated nonyl an average molecular weight of 4000 ting agent.
17. A process according to claim 7 wherein said salt is an alkali metal salt of a sulfated alkyl aryloxypolyalkoxy alcohol.
of manufacture according to claim 9 weight of said alkali metal salt based on the weight of said fibrous material is incorporated in the latter.
References Cited in the file of this patent UNITED STATES PATENTS 1,868,862 Washburn July 26, 1932 10 2,288,714 Jones July 7, 1942 2,353,978 Weber July 18, 1944 2,372,171 Bennett Mar. 27, 1945 2,489,026 Gilbert Nov. 22, 1949 2,561,000 Carson July 17, 1951 OTHER REFERENCES Borghetty: Synthetic Detergents in Textile Process ing, Am. Dyestufi Reporter, vol. 37, pp. '112, 113 and 1 .2, Feb 3194

Claims (1)

1. AS AN ARTICLE OF MANUFACTURE USEFUL IN PREVENTING THE FORGING OF GLASS AND THE LIKE, COMPRISING A FIBROUS MATERIAL HAVING INCORPORATED THEREIN AT LEAST 3% BY WEIGHT BASED ON THE ORIGINAL WEIGHT OF SAID FIBROUS MATERIAL OF AN ALKALI METAL SALT OF SULFATED ALKYL ARYLOXYPOLYALKOXY ALCOHOL.
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Cited By (32)

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US3406418A (en) * 1967-09-27 1968-10-22 Harry J. Hurley Jr. Lens-cleaning paper
US3413825A (en) * 1963-12-30 1968-12-03 Celanese Corp Metering warp knit fabrics
US3637408A (en) * 1969-05-26 1972-01-25 Formica Corp Decorative laminates carrying removable protective coating
US3819522A (en) * 1972-09-25 1974-06-25 Colgate Palmolive Co Anti-fogging window cleaner surfactant mixture
US3897356A (en) * 1973-02-28 1975-07-29 Scott Paper Co Windshield wipers containing nonionic surfactant
US3954642A (en) * 1972-12-02 1976-05-04 Henkel & Cie Gmbh Impregnated textile fibrous structures for cleaning purposes
US3956155A (en) * 1972-12-02 1976-05-11 Henkel & Cie G.M.B.H. Textile fibrous cleaning structures
US4666621A (en) * 1986-04-02 1987-05-19 Sterling Drug Inc. Pre-moistened, streak-free, lint-free hard surface wiping article
US5585186A (en) * 1994-12-12 1996-12-17 Minnesota Mining And Manufacturing Company Coating composition having anti-reflective, and anti-fogging properties
US5846650A (en) * 1996-05-10 1998-12-08 Minnesota Mining And Manufacturing Company Anti-reflective, abrasion resistant, anti-fogging coated articles and methods
US5873931A (en) * 1992-10-06 1999-02-23 Minnesota Mining And Manufacturing Company Coating composition having anti-reflective and anti-fogging properties
US6040053A (en) * 1996-07-19 2000-03-21 Minnesota Mining And Manufacturing Company Coating composition having anti-reflective and anti-fogging properties
US6057961A (en) * 1996-02-29 2000-05-02 3M Innovative Properties Company Optical film with increased gain at non-normal angles of incidence
US6111697A (en) * 1998-01-13 2000-08-29 3M Innovative Properties Company Optical device with a dichroic polarizer and a multilayer optical film
US6256146B1 (en) 1998-07-31 2001-07-03 3M Innovative Properties Post-forming continuous/disperse phase optical bodies
US20010011779A1 (en) * 1998-01-13 2001-08-09 3M Innovative Properties Company Method for making textured multilayer optical films
US6310671B1 (en) 1995-04-07 2001-10-30 Honeywell, Inc. Polarization sensitive scattering element
US6352761B1 (en) 1998-01-13 2002-03-05 3M Innovative Properties Company Modified copolyesters and improved multilayer reflective films
US6419483B1 (en) 2000-03-01 2002-07-16 3M Innovative Properties Company Method and apparatus for curling light-curable dental materials
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US6569515B2 (en) 1998-01-13 2003-05-27 3M Innovative Properties Company Multilayered polymer films with recyclable or recycled layers
US6760157B1 (en) 1996-02-29 2004-07-06 3M Innovative Properties Company Brightness enhancement film
US6797366B2 (en) 1998-01-13 2004-09-28 3M Innovative Properties Company Color shifting film articles
US20050133035A1 (en) * 2003-12-18 2005-06-23 Kimberly-Clark Worldwide, Inc. Facemasks containing an anti-fog / anti-glare composition
US20050163924A1 (en) * 2002-09-17 2005-07-28 3M Innovative Properties Company Porous surfactant mediated metal oxide films
US20080128927A1 (en) * 2002-10-24 2008-06-05 3M Innovative Properties Company Methods of making high gain optical devices having a continuous and dispersive phase
EP2147771A2 (en) 1998-01-13 2010-01-27 Minnesota Mining And Manufacturing Company Process for making multilayer optical films
US20100035039A1 (en) * 2008-08-07 2010-02-11 3M Innovative Properties Company Acicular silica coating for enhanced hydrophilicity/transmittivity
US7852560B2 (en) 1993-12-21 2010-12-14 3M Innovative Properties Company Display incorporating reflective polarizer
US20110033694A1 (en) * 2008-05-16 2011-02-10 Naiyong Jing Silica Coating For Enhanced Hydrophilicity/Transmittivity
US9034489B2 (en) 2009-07-03 2015-05-19 3M Innovative Properties Company Hydrophilic coatings, articles, coating compositions and methods
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US2353978A (en) * 1938-06-25 1944-07-18 Harold C Weber Polishing and fogging inhibiting product
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Cited By (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3413825A (en) * 1963-12-30 1968-12-03 Celanese Corp Metering warp knit fabrics
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