US3830768A - Ethylene copolymer dispersions containing a halogenated alkyl phosphate - Google Patents

Ethylene copolymer dispersions containing a halogenated alkyl phosphate Download PDF

Info

Publication number
US3830768A
US3830768A US1180970A US3830768A US 3830768 A US3830768 A US 3830768A US 1180970 A US1180970 A US 1180970A US 3830768 A US3830768 A US 3830768A
Authority
US
United States
Prior art keywords
percent
weight
dispersion
ethylene
copolymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
Other languages
English (en)
Inventor
B Martinez
G Pruckmayr
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US1180970 priority Critical patent/US3830768A/en
Priority to FR7105075A priority patent/FR2078621A5/fr
Priority to DE19712107373 priority patent/DE2107373A1/de
Priority to GB2190671A priority patent/GB1335919A/en
Priority to US20891971 priority patent/US3814623A/en
Application granted granted Critical
Publication of US3830768A publication Critical patent/US3830768A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/04—Homopolymers or copolymers of ethene
    • C09D123/08—Copolymers of ethene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/24—Flameproof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/92—Fire or heat protection feature
    • Y10S428/921—Fire or flameproofing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2213—Coating or impregnation is specified as weather proof, water vapor resistant, or moisture resistant
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2631—Coating or impregnation provides heat or fire protection
    • Y10T442/2672—Phosphorus containing
    • Y10T442/2697—Phosphorus and halogen containing compound

Definitions

  • This invention relates to stable aqueous dispersions of ethylene copolymers and polyester fabrics coated therewith. More particularly, this invention relates to stable aqueous dispersions of ethylene copolymers, finely divided particulate matter llers and halogenated alkyl phosphate, useful as rainproof and fire-retardant coatings for polyester fabrics.
  • a stable aqueous dispersion comprising as essential ingredients: (1) about 20 to 95 percent by weight of an ethylene copolymer comprising at least 30 percent by weight ethylene and up to 70 percent by weight of at least one polar monomer, (2) 0 to about 25 percent by weight of a finely divided particulate matter filler and (3) about 5 to 80 percent by weight of a halogenated alkyl phosphate.
  • an article of manufacture which comprises a polyester fabric coated with the dispersed phase of the above dispersion. Such a coating renders the polyester fabric rainproof and flame-retardant while retaining breathability.
  • the component ranges of dispersions of the present invention are shown in the drawing and are prepared by adding a dispersion of the halogenated alkyl phosphate to a dispersion of the ethylene copolymer.
  • the latter dispersion can be prepared by a post-dispersion process such as described in U.S. Pat. 3,296,172 issued to D. L. Funck and V. C. Wolff, Jr. on Ian. 3, 1967, U.S. Pat. 3,347,811 issued to T. C. -Bissot on Oct. 17, 1967, and U.S. Patent application Ser. No. 801,741 filed by -T C. Bissot on Feb. 24, 1969.
  • An optional, but highly preferred ingredient is a ⁇ finely divided particulate matter filler which can be blended as a dispersion with the ethylene copolymer dispersion and halogenated alkyl phosphate dispersion.
  • conventional surfactants are not needed, but may be desirable; however, when separate dispersions are prepared and then blended, a conventional surfactant having an HLB number greater than 18 is preferred to aid in stabilizing the dispersion.
  • Such surfactants are known to those skilled in the art.
  • the resulting dispersions have a high solids content, on the order of 40 to 70 percent by lweight, but are generally diluted down to 15 to 40 percent solids when applied as a coating on fabric. They are storage stable at room temperature and can be coalesced into films by removal of the aqueous medium either at room: temperature or at elevated temperatures up to C., as required for maximum strength of the particular film.
  • the ethylene copolymers useful in the present invention have an ethylene content of at least 30 percent by Weight, preferably 60 percent by weight, and up to 70 percent by Weight of at least one polar monomer.
  • monomers having polar characteristics are: vinyl esters of carboxylic acids such as vinyl formate, vinyl acetate, vinyl propionate and vinyl butyrate; unsaturated carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid and maleic acid; acrylates and methacrylates such as methyl methacrylate, ethyl acrylate and isobutyl acrylate; halogenated vinyl compounds such as vinyl chloride and vinylidene chloride, vinyl alcohol (hydrolyzed vinyl acetate); acrylamide, dimethyl-aminoethyl methacrylate, -hydroxyethyl acrylate, and other adhesion-promoting monomers ha'ving carboxyl, amido, amino or hydroxyl groups.
  • One particularly preferred copolymer is a copolymer of ethylene and Vinyl acetate having at least 60 percent by Weight ethylene, 17 to 40 percent by weight vinyl acetate and 0 to 5 percent by weight of an alpha, beta-ethylenically unsaturated carboxylic acid, such as acrylic acid or methacrylic acid.
  • Such copolymers are generally prepared by high-pressure free-radical catalysis processes, .but they can also be prepared by low-pressure coordination catalysis processes.
  • Exemplary patents illustrating copolymer preparation are U.S. Pat. 2,703,794 issued to Milton J. Roedel on Mar. 8, 1955 and U.S. Pat. 3,215,657 issued to Aleksander Beresniewicz on Nov. 2, 1965.
  • the molecular weight can be varied over a wide range; however, copolymers having molecular weights corresponding to melt indexes of 1 to 150, particularly under l5, are especially suited for use in this invention. Copolymer melt index is determined as described in ASTM-D-l238-65T.
  • Another particularly preferred copolymer is a copolymer of ethylene and an alpha, beta-ethylenically unsaturated carboxylic acid having atleast 60 percent by weight, preferably 80 percent, ethylene and 0.3 to 40 percent by weight of the acid, preferably 0.3 to 20 percent, about 10 to 100 percent of the acid groups neutralized with alkali metal ions such as Na+ or K+.
  • Typical acids are acrylic acid, methacrylic acid, fumaric acid, maleic acid, itaconic acid and aconitic acid. Acid derivatives of the aforesaid, such as esters, amides, anhydrides and the like also can be employed as monomers.
  • halogenated alkyl phosphates useful in the present invention have 2 to 18 carbon atoms in the alkyl group with the halogen no more than 5 carbon atoms away from the phosphorus atom.
  • Preferred materials are the chloro and bromo alkyl phosphates wherein the alkyl group contains from 2 to 5 carbon atoms.
  • a particularly preferred compound due to its commercial availability in dispersion form is tris-(2,3-dibromopropyl) phosphate.
  • finely divided particulate matter llers are particularly preferred in the dispersions of the present invention, to aid in fabric breathability, and the polyester coatings formed therefrom, they are not essential.
  • the following fillers can -be employed and it is preferred that a majority of the particles be under about 2 microns so as to be stable in the dispersion.
  • Typical llers are various types of clays such as the more or less impure hydrated aluminum silicates or clays upgraded by beneficiaation procedures. Also, other mineral silicates can be used as fillers.
  • fillers are metal oxides such as titanium oxide, zinc oxide, bismuth oxide and antimony trioxide; metal carbonates such as calcium carbonate; metal phosphates such as zinc phosphate; and metal borates such as zinc borate and magnesium borate.
  • the llers can be used by themselves or mixed together with other fillers or inorganic or organic pigments for tinting purposes.
  • the pigments can also be used by themselves as fillers.
  • Typical pigments beside the above titanium dioxide and calcium carbonate are phthalocyanine green or blue, calcium yellow, chrome yellow, zinc yellow, molybdate red, ferric oxide, indanthrone blues and diazo pigments.
  • the dispersions of the present invention are especially suited for rendering polyester fabrics rainproof and flameretardant.
  • Polyester fabrics used can be manufactured from polyethylene terephthalate fibers as well as from fibers of poly 1,4-cyclohexalene dimethylene terephthalate and of polycondensation products with copolyesters structured from members of the group comprising adipic acid, terephthalic acid, hexahydroterephthalic acid, 2,'6-naphthalene dicarboxylic acid and dibenzoicacid.
  • the dispersion is coated on the fabric according to the usual procedures so as to give a coating add-on, based on the weight of fabric, of about to 75 percent, preferably about 20 to 50 percent.
  • the amount of halogenated alkyl phosphate used in the dispersion and the dispersion used depends t o a great extent upon the basis weight of the fabric, i.e.,.1f the fabric is less than 5 ounces per square yard, the d1spersion preferably contains about 5 to 25 percent of halogenated alkyl phosphate, about 1 to 10 percent filler and about 65 to 90 percent ethylene copolymer whereas for a fabric having a basis weight greater than 5 ounces per square yard, the dispersion preferably contains about 20 to 60 percent halogenated alkyl phosphate, about 1 to 10 percent filler and about 40 to 60 percent ethylene copolymer.
  • the re-retardance test is conducted on impregnated and dried samples according to a modified ASTM D--626- 55T.
  • the test consists of clamping fabric samples 3.75 inches wide by 12.5 inches high vertically in a shielded chamber, 3A; inch above a Micro Bunsen Burner, and igniting the samples by applying a luminous llame of 1.5 inches in length for 12 seconds at the center of the lower edge of the test sample. After removing the burner, the after-flame and challengths of the test samples are recorded. Samples having no after-llame are characterized as non-burning while samples having an after-flame of less than 2 seconds are characterized as self-extinguishing. The char-length shall not exceed 4.5 inches.
  • the rainproof test is conducted by flowing water at a rate of 270 inches/hour (1.5 gallons/min.) from a height of 60 inches onto a fabric sample 8 inches by 7.5 inches for 30 minutes and measuring the amount of water passing through the fabric. Fabric that passes less than ml./30 min. is characterized as having satisfactory rainproofness.
  • TAPPI water vapor permeability test T448 M49 is used to test fabric breathability. A small dish, containing water, is tightly covered with the fabric sample; and the loss of weight of this combination, kept at 73 F. and 50 percent R.H. for 24 hours, it recorded. The grams of water vapor lost per 24 hours per square meter of fabric surface is the water vapor permeability of the fabric sample.
  • the water repellency of a coated fabric sample is conducted in accordance with ASTM D-583-63.
  • the test consists of spraying 250 ml. of water through the standardized spray nozzle onto a fabric sample (7" x 7), fastened at an angle of 45, 6 inches below the nozzle.
  • the spray rating is determined by comparing the test specimen with the photographic standards on a Spray Test Rating Chart in the standard.
  • EXAMPLE 1 This example will illustrate the use of a system with a high content of llame retardant.
  • An aqueous dispersion blend was prepared by thoroughly mixing 65 g. of tris-(2,3-dibromopropyl) phosphate, emulsiiied with the aid of sodium lauryl sulfate anionic surfactant (Dupono1) to a 65% aqueous emulsion, 50 g. of an ethylene/vinyl acetate copolymer dispersion (50% solids) in which the copolymer contains 28% vinyl acetate, and 10 g. of Calcotone organic yellow pigment as liller sold by Union Carbide Corp. This blend was diluted with 240 ml. water to a total of 400 g. dispersion containing 25% solids.
  • the dispersion was stable and was used to impregnate 100% polyethylene terephthalate fabric (4.8 02s./ sq. yd.) to an add-on of 30 weight percent.
  • the coating was coalesced at C. for a least 60 seconds. This fabric is non-burning as determined by the tire retardance test ASTM-D-626-55T.
  • Hydratex clay is a fine particle size (77 to 80% ner than 2 microns), white, insoluble, nonhydroscopic kaolin containing 44 to 46% Silica and 37 to 40% alumina with other oxides in trace amounts.
  • the clay dispersion has a pH of 4.5 to 5
  • Ultrawhite 90 has 92% 0f the particles finer than 2 microns and its dispersion has a pH of 6.3 to 7.
  • EXAMPLE 2 This example will illustrate the use of a system with a high content of ethylene/ vinyl acetate copolymer.
  • An aqueous dispersion blend was prepared by mixing 80 g. of the ethylene/vinyl acetate copolymer dispersion of Example 1, g. tris-(2,3-dibromopropyl) phosphate as a 65% aqueous dispersion, and 5 g. of Clay HT as ller.
  • Clay HT is the same as Hydratex except 80% of the particles are finer than 2 microns and a resulting clay dispersion has a pH of 4 to 4.4.
  • This blend formed a stable dispersion having a pH greater than 7. It was used to impregnate the polyester fabric of Example 1 to an addon of 30% by weight. The coating was coalesced at 150 C. for at least 60 seconds. This fabric is self-extinguishing, having an after-flame of less than 2 seconds, as determined by the ASTM test D-626-55T.
  • EXAMPLE 3 Using the same technique as described in Example 1, a dispersion blend was prepared by mixing 45 g. of the ethylene/vinyl acetate copolymer in the form of a 50% aqueous dispersion, 40 g. of tris-(2,3 dibromopropyl) phosphate as a 60% aqueous emulsion, and 15 g. of phthalocyanine blue Monastral pigment as
  • EXAMPLE 4 This is an example of a dispersion which will impart illustrative of the invention, while Formulation C does not contain a fire retardant.
  • Formulation A Following the procedure of Example 1, 100 g. of the ethylene/vinyl acetate copolymer dispersion, 4 g. of Calcotone Yellow pigment aqueous dispersion (30% solids) and 10 g. of an aqueous dispersion of tris-(2,3-dibromopropyl) phosphate (45.5% solids) were mixed to form a stable aqueous dispersion in which the solids comprised 89.7% copolymer, 2.1% pigment and 8.2% tris-(2,3-dibromopropyl) phosphate.
  • Formulation B This formulation is the same as Formulation A except a Monastral blue pigment dispersion was used as ller and the tris-(2,3-dibromopropyl) phosphate dispersion contained 60% solids. The resulting stable dispersion solids contained 87.4% copolymer, 2.1% pigment and 10.5% tris-(2,3-dibromopropy1) phosphate.
  • a sample of polyethylene terephthalate fabric 8" by 10" and having a gray weight of 4.9 ozs./sq. yd. was coated to an add-on of 33%. The sample was dried at 160 C. for 180 seconds. The coating and test results are shown in Table I.
  • Formulation C This formulation is the same as Formulation A except the fire retardant has been omitted.
  • the solids of the resulting stable dispersion contained 97.7% copolymer and 2.3% pigment.
  • a sample of polyethylene terephthalate fabric 8" by 10 and having a gray weight of 4.8 ozs./sq. yd. was coated to an add-on of 15%. As in Formulations A and B, the sample was dried at 160 C. for 180 seconds.
  • An intimate dispersion was prepared by blending 56 g. of partially neutralized ethylene/methacrylic acid copolymer (89% ethylene, 11% methacrylic acid, 70% neutralized with NaOH) and wax dispersion (15% ethylene ionomer, 85% paran wax), 34 g. of tris-(2,3-dibromopropyl) phosphate as a 60% aqueous dispersion, and 10 g. of Monastral blue pigment.
  • This blend was diluted with water to the total solids content of 10% solids, and was used to impregnate the polyester fabric of Example 1 to an add-on of 25%. After a thorough curing cycle of at least 2 minutes at 165 C., the fabric was found to be flame-resistant as determined by the vertical test described in ASTM D-262-T and Water repellent as determined by the spray test described in ASTM D-583-63.
  • a stable aqueous dispersion comprising as essential ingredients: (l) about 20 to 95 percent by weight of an ethylene copolymer comprising at least 30 percent by weight ethylene and up to 70 percent by weight of at least one polar monomer selected from the group consisting of vinyl esters of carboxylic acids, unsaturated carboxylic acids, acrylates, methacrylates, halogenated vinyl compounds, and adhesion-promoting monomers having carboxyl, amido, amino or hydroxyl groups, (2) 0 to 25 percent by weight of a nely divided particulate matter ller selected from the group consisting of clay, metal oxides, metal earbonates, metal phosphates, metal borates, metal silicates, inorganic pigments, organic pigments or mixtures thereof, and (3) about 5 to 80 percent by weight of a halogenated alkyl phosphate having 2 to 18 carbon atoms in the alkyl group with the halogen no more than 5 carbon atoms away from the phosphorus atom.
  • ethylene c0- polymer is selected from the group consisting of 1) at least 60 percent by weight ethylene, about 17 to 40 percent by weight vinyl acetate and to about 5 percent by weight of an alpha, beta-ethylenically unsaturated carboxylic acid, and (2) at least 60 percent by weight ethylene and about 0.3 to 40 percent by weight of an alpha, beta-ethylenically unsaturated carboxylic acid, about to 100 percent of the acid groups neutralized with alkali metal lons.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US1180970 1970-02-16 1970-02-16 Ethylene copolymer dispersions containing a halogenated alkyl phosphate Expired - Lifetime US3830768A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US1180970 US3830768A (en) 1970-02-16 1970-02-16 Ethylene copolymer dispersions containing a halogenated alkyl phosphate
FR7105075A FR2078621A5 (OSRAM) 1970-02-16 1971-02-15
DE19712107373 DE2107373A1 (de) 1970-02-16 1971-02-16 Wässrige Athylencopolymensatdispersion und Verwendung derselben zum Beschichten von Polyestertextilstoffen
GB2190671A GB1335919A (en) 1970-02-16 1971-04-19 Aqueous dispersion of ethylene copolymers for coating or impregnating polyester fabrics
US20891971 US3814623A (en) 1970-02-16 1971-12-16 Polyester fabrics coated with ethylene copolymer dispersions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1180970 US3830768A (en) 1970-02-16 1970-02-16 Ethylene copolymer dispersions containing a halogenated alkyl phosphate
US20891971 US3814623A (en) 1970-02-16 1971-12-16 Polyester fabrics coated with ethylene copolymer dispersions

Publications (1)

Publication Number Publication Date
US3830768A true US3830768A (en) 1974-08-20

Family

ID=26682816

Family Applications (2)

Application Number Title Priority Date Filing Date
US1180970 Expired - Lifetime US3830768A (en) 1970-02-16 1970-02-16 Ethylene copolymer dispersions containing a halogenated alkyl phosphate
US20891971 Expired - Lifetime US3814623A (en) 1970-02-16 1971-12-16 Polyester fabrics coated with ethylene copolymer dispersions

Family Applications After (1)

Application Number Title Priority Date Filing Date
US20891971 Expired - Lifetime US3814623A (en) 1970-02-16 1971-12-16 Polyester fabrics coated with ethylene copolymer dispersions

Country Status (4)

Country Link
US (2) US3830768A (OSRAM)
DE (1) DE2107373A1 (OSRAM)
FR (1) FR2078621A5 (OSRAM)
GB (1) GB1335919A (OSRAM)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4331780A (en) * 1980-03-20 1982-05-25 Phillips Petroleum Company Flame retardant transparent resinous copolymer
WO1992009739A1 (en) * 1990-11-29 1992-06-11 Rheem Australia Limited Coated fabric for weather protection
US20050209358A1 (en) * 2004-03-05 2005-09-22 Miller Joseph E High energy curable coatings comprising thermoplastic polymers

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4368233A (en) * 1976-03-29 1983-01-11 Standard Oil Company (Indiana) Coated woven and non-woven polyolefin articles
DE4015120A1 (de) * 1990-05-11 1991-11-14 Hammersteiner Kunststoffe Gmbh Textile werkstoffbahn zur herstellung von lkw-planen o. dgl.
US5591806A (en) * 1991-05-20 1997-01-07 Dominion Chemical Company High solids ethylene acrylic acid aqueous dispersions and methods of producing same
US6762239B1 (en) * 2000-11-21 2004-07-13 National Starch And Chemical Investment Holding Corporation Highly functionalized ethylene-vinyl acetate emulsion copolymers
CN111549526A (zh) * 2020-03-27 2020-08-18 浙江万舟控股集团有限公司 一种有机-无机杂化阻燃聚乳酸织物及其制备方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4331780A (en) * 1980-03-20 1982-05-25 Phillips Petroleum Company Flame retardant transparent resinous copolymer
WO1992009739A1 (en) * 1990-11-29 1992-06-11 Rheem Australia Limited Coated fabric for weather protection
US20050209358A1 (en) * 2004-03-05 2005-09-22 Miller Joseph E High energy curable coatings comprising thermoplastic polymers
US7527864B2 (en) 2004-03-05 2009-05-05 The Sherwin-Williams Company High energy curable coatings comprising thermoplastic polymers

Also Published As

Publication number Publication date
US3814623A (en) 1974-06-04
DE2107373A1 (de) 1971-08-26
GB1335919A (en) 1973-10-31
FR2078621A5 (OSRAM) 1971-11-05

Similar Documents

Publication Publication Date Title
US3891591A (en) Coating compositions
US3955032A (en) Flame retardants for natural and synthetic materials
US3943085A (en) Suspension copolymer composition
US3830768A (en) Ethylene copolymer dispersions containing a halogenated alkyl phosphate
US2727012A (en) Latex coating compositions containing zinc phosphate-modified zinc oxide
US3691127A (en) Fire retardant vinyl chloride copolymer latices
US3654193A (en) Opaque microporous film and process for preparing the same
US3897389A (en) Flame retardant compositions
US4012546A (en) Flame-retardant carpet
JPS62553A (ja) 改善された耐燃性を有する重合体組成物
US4177181A (en) Flame-retardant adhesive compositions
EP0548199B1 (en) Flame retardant brominated styrene-based coatings
US3258441A (en) Soil and slip resistant coating compositions
US3883455A (en) Non-bleeding vinylidene chloride copolymer coatings
US2984635A (en) Composition comprising alumina particles coated with polymer of ethylenically unsaturated monomer
US3819770A (en) Fire retardant thermoplastic polymer compositions
US3789047A (en) Ethylene copolymer dispersions for flame retardation and fibrous articles coated therewith
US3661807A (en) Soluble fluorescent materials and optical brighteners in solvent precipitation film compositions
US3475199A (en) Fire-retardant coating
US3745135A (en) Polymerized ethylenically unsaturated fatty acids as emulsifiers for aqueous dispersions
US3935149A (en) Fire retardant aqueous emulsion copolymer additives
US3992482A (en) Fire retardant thermoplastic polymer compositions
US3842048A (en) Fire retardant crosslinked copolymers
US3962170A (en) Flame resistant vinylidene chloride copolymer latices and articles made therefrom
US4640862A (en) Coated, heat shrinkable expanded polystyrene