EP0547157A1 - Coemulsionnement d'homopolymeres de polyethylene oxyde et de fluides de silicone amino-fonctionnelle - Google Patents
Coemulsionnement d'homopolymeres de polyethylene oxyde et de fluides de silicone amino-fonctionnelleInfo
- Publication number
- EP0547157A1 EP0547157A1 EP91917878A EP91917878A EP0547157A1 EP 0547157 A1 EP0547157 A1 EP 0547157A1 EP 91917878 A EP91917878 A EP 91917878A EP 91917878 A EP91917878 A EP 91917878A EP 0547157 A1 EP0547157 A1 EP 0547157A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- reactor
- temperature
- ethoxylated
- constituents
- polyethylene
- 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.)
- Withdrawn
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 17
- 229920005638 polyethylene monopolymer Polymers 0.000 title claims description 3
- 239000012530 fluid Substances 0.000 title abstract description 15
- 239000000470 constituent Substances 0.000 claims abstract description 98
- -1 polyethylene Polymers 0.000 claims abstract description 72
- 239000004698 Polyethylene Substances 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 53
- 229920000573 polyethylene Polymers 0.000 claims abstract description 53
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003333 secondary alcohols Chemical class 0.000 claims abstract description 12
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 11
- 229920000847 nonoxynol Polymers 0.000 claims abstract description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 6
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 3
- 239000000194 fatty acid Substances 0.000 claims abstract description 3
- 229930195729 fatty acid Natural products 0.000 claims abstract description 3
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 89
- 239000000463 material Substances 0.000 claims description 49
- 238000010438 heat treatment Methods 0.000 claims description 36
- 239000004753 textile Substances 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000013019 agitation Methods 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000000835 fiber Substances 0.000 claims description 10
- 239000010426 asphalt Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 239000000155 melt Substances 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 5
- 229920001684 low density polyethylene Polymers 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229920001903 high density polyethylene Polymers 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 239000004702 low-density polyethylene Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 229920001897 terpolymer Polymers 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004700 high-density polyethylene Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 230000000063 preceeding effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 150000003839 salts Chemical class 0.000 abstract description 5
- 239000000839 emulsion Substances 0.000 description 47
- 239000002245 particle Substances 0.000 description 47
- 239000004744 fabric Substances 0.000 description 23
- 239000000123 paper Substances 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000654 additive Substances 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000004530 micro-emulsion Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 230000000977 initiatory effect Effects 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 5
- 229920013822 aminosilicone Polymers 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002296 dynamic light scattering Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
- 229940001584 sodium metabisulfite Drugs 0.000 description 4
- 235000010262 sodium metabisulphite Nutrition 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000004838 Heat curing adhesive Substances 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 238000009958 sewing Methods 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical class CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000000181 anti-adherent effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 230000033001 locomotion Effects 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000004447 silicone coating Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000003655 tactile properties Effects 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- NDLNTMNRNCENRZ-UHFFFAOYSA-N 2-[2-hydroxyethyl(octadecyl)amino]ethanol Chemical compound CCCCCCCCCCCCCCCCCCN(CCO)CCO NDLNTMNRNCENRZ-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- OBFQBDOLCADBTP-UHFFFAOYSA-N aminosilicon Chemical compound [Si]N OBFQBDOLCADBTP-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000010219 correlation analysis Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000012905 visible particle Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
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- 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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/495—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as oligomers or polymers
- C04B41/4961—Polyorganosiloxanes, i.e. polymers with a Si-O-Si-O-chain; "silicones"
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L23/30—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by oxidation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/06—Waxes
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- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
- D06M11/13—Ammonium halides or halides of elements of Groups 1 or 11 of the Periodic Table
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- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table
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- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
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- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/152—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/165—Ethers
- D06M13/17—Polyoxyalkyleneglycol ethers
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- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
- D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
-
- 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
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
- Y10T428/252—Glass or ceramic [i.e., fired or glazed clay, cement, etc.] [porcelain, quartz, etc.]
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2962—Silane, silicone or siloxane in coating
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
- Y10T428/2969—Polyamide, polyimide or polyester
-
- 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
- Y10T442/2311—Coating or impregnation is a lubricant or a surface friction reducing agent other than specified as improving the "hand" of the fabric or increasing the softness thereof
- Y10T442/2328—Organosilicon containing
Definitions
- the invention relates to coemulsions of amino functional silicone fluids and oxidized polyethylene and processes for making the same.
- Emulsions of various organic compounds are well known in many arts for their widespread utility.
- compositions including creams, lotions, cosmetic compositions, and the like.
- Other examples include uses as lubricating agents for sheet-like materials, including papers and fabrics, softening agents for textiles, fiber lubricants, paper release agents, metal working, coatings and as oil-recovery fluids from subterranean formations.
- polyethylene are in the area of textiles, for such purposes as lubricants which aid during textile
- Fibers Having Improved Slip Properties which is directed to a polymeric organosilicon compound
- Polyethylenes in Textiles describes a family of emulsifiable polyethylenes and methods for making emulsion which include these products, as well as beneficial features which are imparted unto textiles through the use of these materials and compositions.
- this data sheet does not teach or suggest the invention to be presented herein.
- coemulsion wherein the coemulsion is a stable aqueous coemulsion of oxidized polyethylene or polyethylene copolymers with amino functional silicone fluids which includes at least one constituent selected from the group consisting of; ethoxylated aliphatic amines, ethoxylated octylephenols, ethoxylated nonylphenols, ethoxylated primary alcohols, ethoxylated secondary alcohols or other nonionic emulsifiers.
- amino functional silicone fluids which includes at least one constituent selected from the group consisting of; ethoxylated aliphatic amines, ethoxylated octylephenols, ethoxylated nonylphenols, ethoxylated primary alcohols, ethoxylated secondary alcohols or other nonionic emulsifiers.
- coemulsions may also comprise further constituents, including but not limited to fatty acids, ammonium hydroxide, salts and water.
- a method of producing a coated article comprising a coemulsion of oxidized polyethylene with amino functional silicone fluids, as described above wherein such method comprises process steps of: heating said constituents in the presence of water with agitation in a sealed and pressurized reaction vessel through the melt point of the oxidized polyethylene constituent, further raising the
- Suitable polyethylenes may be characterized as oxidized low density and high density homopolymers of ethylene, copolymers containing acrylates and ethylene, terpolymers containing acrylates, esters and ethylene. These polyethylenes have preferably been oxidized to an acid number as determined by a standardized titration of KOH of about 5 and 55, more preferably between about 10 and 50, and most preferably between about 10 and 45. These polyethylenes typically have a density as
- polyethylenes exhibit a Brookfield viscosity at a temperature of 140 deg.C of between about 185 and 6000 centipoises (hereinafter interchangeably referred to as "cps"), more preferably in the range of about 190 and 6000 cps, and most preferably in the range of between about 190 and 5500 cps.
- cps centipoises
- Such oxidized polyethylenes are currently commercially available from the Allied- Signal Corp. under the designations of A-C ® 629 and 392.
- the former is described as having a density of 0.93 an acid number of 16 and a Brookfield viscosity of 200 cps, while the latter is described as having a density of 0.99, an acid number of 30 and a Brookfield viscosity of 4500 when measured at a temperature of 4500 deg C.
- oxidized polyethylenes as well as others which are useful in the practice of the instant invention may be obtained by oxidizing polyethylenes with air or oxygen by conventional procedures.
- amino functional silicone fluids which may be used in accordance with the invention are those which may be broadly described as amino organic radicals
- modified polysiloxanes alternatively known to the art as “polydiorganosiloxanes”.
- polydiorganosiloxanes Preferable
- suitable group of materials include Dow Corning ® CSF and Dow Corning ® SSF which are sold as textile
- polydiorganosiloxane which comprise aminoalkyl groups affixed to a predominantly polydimethyIsiloxane
- the amine neutral equivalent is described to be approximately 2000, the specific gravity at 25 deg.C (77 deg.F) of 0.96, and to have a viscosity at 25 deg.C (77 deg.F) of 1300 centistokes (hereinafter interchangeably referred to as "cst").
- a further commercially available material includes UCARSIL ®
- compositions are described to be low viscosity amino functional silicones which have a viscosity of about 250 cst at a temperature of 25 deg.C (77 deg.F), a specific gravity of 0.97 at 25 deg.C (77 deg.F).
- 77 deg.F 25 deg.C
- specific gravity 0.97 at 25 deg.C
- polydiorganosiloxane material includes those which are marketed by PPG-Mazer under the designations MASIL ® 123 and MASIL ® 124.
- the microemulsion includes at least one constituent selected from the group
- ethoxylated octylphenols ethoxylated nonylphenols, ethoxylated primary alcohols, ethoxylated secondary alcohols.
- the at least one constituent selected from this group which is added to the polyethylene and the amino functional silicone fluid in accordance to the teaching of this present invention may be
- additive system includes only one or more of constituents selected from: ethoxylated aliphatic amines, ethoxylated
- additive system as used throughout this specification and the claims are to be understood to be limited to the group of four constituents described.
- ethoxylated aliphatic amines which are suitable to the practice of the invention are those which may be described as saturated and unsaturated fatty amines reacted with ethylene oxide. These materials which are useful in the practice of the present invention may be generally termed as the condensation products of ethylene oxide with a
- hydrophobic material such as a long chain aliphatic alcohol, ester, acid, ether or alkyl phenol. These materials which find use in conjunction with the invention are characterized by containing as the hydrophilic portion of the molecule a plurality of oxyethylene moieties. Suitable materials of this type may also be referred to as ethoxylated tallow amines, a designation commonly used in the art.
- ethoxylated aliphatic amines examples include “Ethomeen T-12” and “Ethomeen 18/12” which is available from Akzo Chemie America and which is described as an ethoxylated tallowamine, more particularly described as bis-(2-hydroxyethyl) tallowamine.
- a further example includes "Varonic T-202" which may be described as a constituent having similar characteristics to those described in conjunction with Ethomeen T-12 above, and are believed to be functionally identical. Varonic T- 202 is at present commercially available from the
- ethoxylated amines include ethoxylated octylphenols and nonylphenols which may be described as being the reaction products of an octylphenol or a nonylphenol with ethylene oxide.
- ethoxylated octylphenols and nonylphenols which find use with the instant invention include those which are sold under the designation "Igepal CO-430" which is sold as a surfactant and available from GAF Corporation and which is described as an ethylene oxide, more particularly as nonylphenoxypoly(ethyleneoxy)ethanol having a molecular weight of 484, and a boiling point in excess of 93.30 deg.C.
- ethoxylated alcohols include ethoxylated primary alcohols and ethoxylated secondary alcohols suitable in the practice of the present invention include those which may be described as the reaction product of a primary alcohol or a secondary alcohol and ethylene oxide. Examples of such commercially
- ethoxylated alcohols include; "Tergitol 15-S- 3" available from Union Carbide Corp. of Danbury,
- Ethal TDA-3 which is described as an ethoxylated tridecyl alcohol formed as the reaction product between stoichiometric quantities of 3 moles of ethylene oxide with one mole of tridecyl alcohol
- the polyethylene and amino functional silicone fluid further includes the additive system which consists of at least one
- octylphenols ethoxylated nonylphenols, ethoxylated primary alcohols, ethoxylated secondary alcohols.
- the selected constituent forms 100 percent of the additive system's composition.
- the additive system comprise at least two components where one component is an ethoxylated aliphatic amine, and the other component or components are selected from the remaining members of the group, namely the ethoxylated nonylphenols, ethoxylated primary alcohols, and
- the composition of the additive system consists of the following constituents in the following proportions: ethoxylated aliphatic amines 40 - 100 % mol.,
- the relative molar percentages of the constituents making up the additive system are present in the following ratios: ethoxylated aliphatic amines 60 - 100 % mol.,
- ethoxylated nonylphenol 0 - 40 % mol., ethoxylated primary alcohols, 0 - 40 % mol., ethoxylated secondary alcohols, 0 - 40 % mol.
- quantities of between about 30 to 90 percent by weight of the total composition, more preferably between about 45 to 90 percent by weight, most preferably between about 60 to 80 percent by weight of water are included in the total composition.
- formulating microemulsion compositions include acetic acid in either glacial or dilute forms, which may be added in order to modify the relative acidity of the composition by adjusting the respective pH value thereof.
- the pH should be maintained to adjust the relative affinity to the ethoxylated amine so that material exhibits a greater affinity to the olefins in the overall composition rather than an affinity to any water contained in the overall
- Hydrochloric acid in either concentrated, i.e. approximately 37% concentrations, or dilute
- hydrochloric acid functions to provide a means to adjust the relative pH of the overall compositions as is described above.
- Ammonium hydroxide is a further useful reagent which may be included in the composition and
- concentrated ammonium hydroxide of an approximate 30% concentration may be used. It has been observed that the presence of ammonia, in even minor amounts in microemulsion compositions according to the present invention imparts a beneficial effect upon the composition which is evidenced by reductions in the opacity of the microemulsions formed containing ammonia relative to the opacity of the microemulsions formed without containing ammonia. This is evident from the improved appearance and measured light transmission measurements which are factors known to the art to be indicative of the relative particle size in an
- Sodium salts including but not limited to sodium chloride, sodium hydroxide, and sodium metabisulfite may be incorporated as a constituent, as the salt provides the desirable effect of reducing the
- the sodium salts may be in any form, such as a finely divided powder, or in a pelletized form, or alternately, the sodium salt may be dissolved in a reagent or other constituent, for example in the water comprising a composition which is subsequently combined with the other constituents.
- the salts may also be in various percentages, and may further include small amounts, i.e., 20 % or less of inert materials which exhibit no detrimental effect upon the practice of the invention.
- the process for forming the microemulsions of the present invention include the following process steps: heating the constituents used to form the microemulsion under conditions of constant
- the first heating rate is greater than the second heating rate, i.e., a faster transmission of heat per unit of time occurs during the first heating rate than during the second.
- suitable reactors include those constructed of metals, glass, glass-lined metal reactors.
- the reaction vessel is a batch type reaction vessel which may be sealed, and which is of sufficient
- reaction may be carried out in any manner, either in a batch type mode, or in a continuous mode or other mode of operation; any reaction mode which is successful in providing the conditions for the productions of the emulsions taught herein may be utilized.
- reaction is carried out in a batch type mode.
- Agitation means are meant to include any means, or alternately any method by which the constituents in the reactor may be well mixed, and by way of example, such means include rotary paddles, propellers, stirring rods, vanes and the like, as well as other methods which may comprise shaking, spinning or otherwise effecting movement of constituents within the reactor.
- polyethylene, amino functional silicone fluid, and the additive system as defined above, as well as other desired constituents are loaded into a reaction vessel which is sealed, and which includes agitation means.
- the selected constituents are heated, with agitation, at a first heating rate through the melting point of the oxidized polyethylene component for a first time interval, and then during a second time interval further heated at a second heating rate to raise the temperature to a maximum temperature or maximum
- the relative acidity of the composition i.e., the "pH" should be evaluated in order assure that the microemulsion is of suitable optical clarity.
- the pH may be adjusted by modifying the amounts of the constituents used, especially by
- the pH of the microemulsion should be maintained in a range of between about 4 to 6, more preferably in the range of between about 4.5 and 5.5, and most preferably in the range of between about 4.75 and 5.25.
- the coemulsification products of this procedure form stable coemulsions of the oxidized polyethylene and amino functional silicone fluid, which include particles in the size range of between about 0.0001 and 100 microns.
- the products of this procedure have particle sizes in the range of between about 0.001 and 5 microns, and most preferably comprise particles having particle sizes in the range of about 0.001 and 1 micron.
- the small particle sizes of the present invention are generally classed as
- microemulsion As is well known in the art, the smaller particle sizes of the emulsion enhance the distribution of the silicon in the
- emulsions and improve the distribution of the silicon within or upon the surface of any material, such as textile, paper or other sheet type material and thereby impart such desirable properties as lubrication, textural modification or other property with a material, such as textile, paper or other sheet type material and thereby impart such desirable properties as lubrication, textural modification or other property with a material, such as textile, paper or other sheet type material and thereby impart such desirable properties as lubrication, textural modification or other property with a
- Photoelectric Colorimeter Model No. 800-3, which was equipped using a number 66 filter which is rated to have a spectral range of between 640 and 700
- Klett Values The values provided by the Klett- Summerson Photoelectric Colorimeter are termed "Klett Values" from which a corresponding optical density and a percent light transmittance can be determined.
- a further optical evaluation of the inventive coemulsions and a blend of two emulsions, i.e., a polyethylene emulsion and an amino silicone containing emulsion was performed on a Leitz Ortholux optical microscope. The magnification was varied as described below, and a xenon lamp lighting source was used in either of two lighting modes, phase contrast or what is commonly referred to in the art as a "transmitted dark- field" in order to improve the contrast of the
- Figures 1-8 illustrate a cationic emulsion formed as a result of a blend of two emulsions produced by producing a mixture under pressure at a temperature in the range of 110 - 115 deg.C of a low density oxidized polyethylene and 2 moles of an ethoxylated tallowamine surfactant in a reactor with stirring, using Masil ® EM 115, a
- Figures 4-6 illustrate a coemulsion formed in accordance with the teaching of the instant invention, whose composition is described below as Example K1.
- Figures 7-8 illustrate an inventive
- Example C14 coemulsion whose composition is designated below as Example C14.
- Fig. 1 which was produced using dark-field illumination illustrates particles which are generally non-uniform in geometrical configuration, particularly the
- Fig.2 illuminated using phase contrast lighting the same sample is viewed under a higher magnification, and two distinct particles are particularly apparent; the particle denoted as 4 is seen to have an irregular shape a particles illustrated in conjunction with
- Fig.1 and the particle denoted 5 is seen to have a spherical or circular shape.
- Fig.3 illuminated by phase contrast lighting shows the same sample as the two prior magnifications at a higher magnification, and the particle denoted as 6 reveals a generally spherical particle, which is approximately 10 microns in diameter.
- the hazy interior suggests that the particle 6 has no internal structure, and it is hypothesized that the particle 6 is a suspended oil particle.
- Figure 6 illuminated under phase contrast lighting further shows visible particles having the internal structure noted above.
- Figures 7 and 8 both illuminated under dark-field lighting modes illustrate two further coemulsions according to the compositions of samples C14 as listed on Table C1 noted below. It should be noted that Figures 7 and 8 further illustrate successful coemulsions which reveal particles having internal structures apparently identical in nature to the particles illustrated on Fig. 4-6.
- M i is representative of the mass of a particle
- d i is representative of the diameter of a particle
- n i is the number of particles having a unit mass.
- the diameters in units of microns ( ⁇ m) are listed in Table PD below.
- inventive coemulsions has been observed to be less than for blended emulsions. This figure suggests that the average diameter of the coemulsion particles are generally smaller than that for blended emulsions, and while not wishing to be bound to this theory, might further be suggestive that they would provide an improvement in lubricative characteristics.
- coemulsions described above may be contacted to a variety of articles so to provide one or more of the following characteristic features: improved
- thermoplastic resins lubricity, improved anti-adhesive properties, improved tactile properties particularly for fibers, threads and textile applications, improved mold release agents for dies and molds for forming articles from thermoplastic resins.
- coemulsions described above by any effective method which method includes conventional methods, which methods include but are not limited to: immersion of the article, immersion of at least part of the article, spraying, coating, brushing-on, or otherwide contacting the coemulsions with the article.
- Fiberfill materials including but not limited to textiles, fibers, ropes, tows, webs, threads, so-called “fiberfill” materials, as well as others are imparted with improved lubricity, improvements in the tactile quality of the article as is commonly referred to in the textile art as "hand”, as well as improved softness of the article.
- Paper and other flexible sheet type articles including but not limited to paper sheets, sheets and films formed from of thermoplastic compositions such as polyesters, may be provided with an anti-adhesive coating and with improved slip characteristics.
- Paper and flexible sheet type articles coated with the coemulsion of the present invention provide a useful carrier or release coating for a wide range of
- One class of adhesives with which the coemulsions of the present inventions find use are with pressure sensitive adhesives and other adhesives which are desirably applied to the surface of one material, upon to which a release paper, release strip or release sheet is applied so to protect the pressure sensitive adhesive until ready for use.
- the release paper, release strip or release sheet is removed, leaving a major portion of the pressure sensitive adhesive in contact with the material upon which it was applied.
- Examples of such articles include tapes, sheets, decals, labels, envelopes, as well as other paper and sheet type articles as well as other articles not enumerated here upon which the pressure sensitive adhesive may be applied.
- the coemulsions of the present invetion find particular use as a coating for the release sheet, release film, release strip or release paper described and feature poor adhesion to the pressure sensitive adhesive, which is desirable property.
- adhesive properties include asphalt containing
- compositions and articles comprising asphalt.
- articles include roofing shingles, and other roofing materials, and packaging containers for asphalt containing compositions.
- the coemulsion compositions taught in the instant invention provide structures featuring good release properties for use in
- roofing shingles such as those presently in common use in North America for buildings, residential buildings and other structures may be generally described as a substantially sheet type article having a length dimension greater than a width dimension, and two opposite faces, an "upper face” upon which is conventionally placed a series or alternately a strip of a heat curing adhesive, and on the "lower face” (the reverse side of the roofing shingle) there is desirably placed a release material which is non-adhesive, or exhibits only limited adhesive characteristics when contacted with the heat curing adhesive.
- the roofing shingles provides a very satisfactory release coating which may be directly applied to the lower surface of a roofing shingle and form a layer of the coemulsion thereon.
- the coemulsions of the present invention may be used to produce a release tape or material of a fiber, paper or thermoplastic material such as a polyester tape which is coated with the coemulsion and afterwards applied to the lower face of the roofing shingle in accordance with conventional methods known to the art.
- such a release tape or material for use with a roofing shingle is a paper tape or a sheet, or a polyester tape or sheet; most preferably such a release tape or material is a polyester tape or sheet such as poly(ethylene terepthalate).
- Packaging containers for asphalt commonly paper containers which are used to contain a mass of asphalt may be coated on the surfaces of the container which are to contact the asphalt with the coemulsions of the present invention.
- the coemulsions of the present invention provide improved release properties as compated to an uncoated packaging container.
- coemulsions taught in the present invention may be substitued in applications wherein it is presently known to the art to use a silicone coating and to replace the silicone coating being used.
- the resultant reaction products of each of the compositions i.e., the emulsions, were evaluated for their Klett values in accordance with the directions of the manufacturer of the Klett-Summerson Photoelectric Colorimeter from which the optical density and percent light transmittance was derived.
- the relative acidity, or pH values was determined by the use of Corning pH meter equipped with a glass electrode.
- the reactor was again sealed, and the operation of the stirrer re-initiated.
- the heating system was initiated and the reactor and its contents were heated at a rate of approximately 2-5 deg.C/min until the constituents in the reactor reached a temperature of 110 deg.C.
- the heating system was disengaged and the reactor allowed to cool in a water bath as described before until it reached a temperature of 30-35 deg.C.
- Example C1 The reactor vessel as described above used for the production of Example C1 was charged with all of the constituents and sealed. Agitation was initiated and maintained to assure the adequate mixing of the
- Example C1 After reaching the temperature of 110 deg.C, heat was supplied to the reaction vessel so to maintain a constant temperature of 110 deg.C for a period of ten minutes.
- the heat source was deactivated, and the reactor vessel was allowed to cool to a temperature of 30-35 deg.C.
- the agitator motion was arrested, and the vessel opened.
- Example C3 In accordance with the methods described above and those used for Example C1, the emulsion was evaluated and the results are described in Table C1.
- Example C3 In accordance with the methods described above and those used for Example C1, the emulsion was evaluated and the results are described in Table C1.
- the reactor vessel was charged with Varonic T-202, Igepal CO-430, acetic acid, sodium chloride, and water in the proportions outlined in Table C1.
- the reactor vessel was sealed and the agitator was energized to assure thorough mixing, and the reaction vessel was heated to 25 deggC, and at a constant temperature of 25 deg.C, the contents stirred for a period of 15 minutes. Afterwards, the reactor vessel was opened, and
- the quantities of A-C ® 629 and the Dow Corning ® CSF were added to the reaction mixture, the reactor then sealed and repressurized and the agitator restarted.
- the reactor was then reheated to 110 deg.C from an initial starting temperature of approximately 90 deg.C at a rate of temperature rise of 1 deg.C per minute of time.
- 110 deg.C the reactor was retained at this constant temperature for a time interval of 1 minute, after which the heat source was removed, and the reactor allowed to cool.
- the agitator was halted, and the reactor was opened. The resulting reactant mixture was observed to produce a slightly milky film when tested upon a glass laboratory slide.
- the heat was limited to maintain the reactor contents within a temperature range of 110 - 112 deg.C for a period of ten minutes (10 min), after which the heat was removed, and the contents cooled to a temperature of approximately 30-35 deg.C.
- the agitator was then halted, and the reactor was opened, at which point was added 0.2 grams of sodium hydroxide in the form of pellets of 90%
- reaction vessel introduced to the reaction vessel, and the vessel was subsequently sealed and the agitator initiated.
- the temperature of the vessel was raised from 22 deg.C to 75 deg.C at a first rate of 2-5 deg.C per minute, and then from 75 deg.C at a second rate of 1 deg.C per minute, to a temperature within the range of 104 - 108 deg.C. Thereafter, the temperature of the reactor contents was maintained in the range of 104 - 108 deg.C .for a period of ten minutes (10 min.), after which time heating of the reactor was terminated and the reactor allowed to cool to 30-35 deg.C.
- the emulsion was evaluated and result are listed on Table C1.
- the temperature of the vessel was raised from approximately 20 deg.C to a temperature range of 78 - 80 deg.C at a first rate of 2-4 deg.C per minute, and then maintained from 75 deg.C within the temperature range of 78 - 80 deg.C for a period of approximately 45 minutes.
- the temperature of the reaction mixture was further elevated at a second rate of 1 deg.C per minute, to a temperature within the range of 104 - 108 deg.C.
- the temperature of the reactor contents was maintained in the range of 104 - 108 deg.C for a period of ten minutes (10 min.), after which time heating of the reactor was terminated and the reactor allowed to cool to 30-35 deg.C.
- the emulsion was evaluated and result are listed on Table C1, with higher Klett values being observed.
- Example C12 The procedure used in Example C12 was replicated, with the substitution of one constituent, the A-C ® 629 with an acid value of 15.9. The resultant emulsion was tested with the results indicated on Table C1. An increase in the Klett value was observed.
- Example C14 The procedure used in Example C12 was replicated, with the substitution of one constituent, the A-C ® 629 with an acid value of 15.9. The resultant emulsion was tested with the results indicated on Table C1. An increase in the Klett value was observed.
- the rate of heating was reduced, and the temperature of the reactor was allowed to rise for a further time interval of approximately thirty-three minutes (33 min.) which was a second average rate of temperature rise of 1 deg.C per minute.
- the heat was reduced and controlled so to maintain the reactor contents within a temperature range of 104 - 109 deg.C for a period of ten minutes (10 min) , after which the heat was removed, and the contents cooled rapidly by immersion into a water bath at a temperature of 20-25 deg.C to a temperature of approximately 30-35 deg.C.
- the resultant emulsion was tested with the results indicated on Table C1.
- Example C14 The procedure used in Example C14 was replicated, using the constituents outlined in Table C1. The resultant emulsion was tested with the results
- a further coemulsification of a high density oxidized polyethylene in combination with an aminosilicone oil was produced.
- the constituents denoted on Table C1 were placed into the reactor which was sealed, stirred and heated in accordance with the following process steps. The constituents were stirred for 45 minutes at a temperature of 27-28 deg.C and then heated in accordance with the following profile: At the initiation of heating, the temperature was 27 deg.C; at 35 minutes, 112 deg.C; at 69 minutes, 130 deg.C; at 76 minutes, 141 deg.C; at 80 minutes, 145 deg.C; at 86 minutes, 144 deg.C, at which point the heat was removed and the reactor cooled in a water bath. The resultant coemulsion was evaluated and the results are listed on Table C1.
- the temperature was 29 deg.C; at 27 minutes, 100 deg.C; at 45 minutes, 120 deg.C; at 54 minutes, 130 deg.C; at 64 minutes, 141 deg.C; at 74 minutes, 144 deg.C, at which point the heat was removed and the reactor cooled in a room temperature water bath.
- the resultant coemulsion was evaluated and found to be good, and the results are listed on Table C1.
- Example C20 The coemulsification process of Example C19 was repeated with the same constituents used in forming Example C19, with the variation that additional ammonia was introduced to the initial constituent mixture in order to evaluate the effects on the acidity of the polyethylene and its effects on the coemulsification process and the coemulsion. The resultant coemulsion was evaluated, and the results denoted on Table C1.
- a coemulsion was prepared in a two-step process where an intial "pre-coemulsion" material was produced, followed by subsequent formation of the coemulsion using the pre-coemulsion material.
- This material formed the pre-coemulsion material.
- compositions designated P1-P8 as outlined in Table PS-1 were produced in accordance with the general methods used for the production of examples C1-C15.
- compositions were formulated as control samples for the purpose of comparison. These included: sample P5 which was a amino silicon control; sample P6 which comprised low density polyethylene; sample P7 which comprised high density polyethylene; and sample P8 which was a paper control blank having no lubricant coating.
- the paper substrate was Westvaco Sterling II Litho Gloss, a web offset paper having an 80# weight rating.
- Compositions Pi - P8 were all coated onto the paper using a wire wound #6 draw down rod, which gave a 0.54 mil wet film thickness. All of the compositions were applied at a 30 % non-volatile level to ensure consistent and equal film deposition.
- coated/coated and “coated/uncoated”. What is meant by “coated/coated” is two contacting faces of the paper substrate used in any particular evaluation were coated with a particular composition so that a measure of the dynamic coefficient of friction of the two coated faces could be evaluated.
- coated/uncoated is that one of two contacting faces of the paper substrate used in an evaluation was coated with a composition so to provide a measure of the dynamic coefficient of friction of one coated face against a non-coated or "neat” face of paper could be determined. The coefficient of friction was determined by the use of a "Coefficient of Friction Tester" Model No. 32-25 produced by Testing Machines, Inc.
- This device includes an inclining board with a weighted sled and measures the angle, at which the individual coated substrates allowed the weighted sled to move. The tangent value of this angle is used as the COF for any test. Test results for each of the compositions P1 - P8 were determined for both "coated/coated" and
- compositions whether such coemulsions utilized low density or high density polyethylenes in their
- compositions were tested in conjunction with fiber and fabric (textile) samples in order to evaluate the effects of the use of the compositions.
- Fabric samples were evaluated by treating samples of a 65/35 polyester/cotton filter cloth where each of the fabric samples was a panel of dimensions 14.5 inches by 18 inches.
- the fabric samples were prepared by separately treating each within a fluid bath which contained one of the compositions labeled as T1 - T16 whose
- compositions are described on Table TS-1 below.
- sample T1 was a control sample consisting of water with no further additives
- samples T2-T5 were samples comprising coemulsions according to the invention and amino silicone
- samples T6-T8 were additional comparative samples of various emulsions
- sample T9 was a
- samples T10-T13 were samples comprising coemulsions according to the invention and amino silicone, and further included the durable press resin, samples T14-T16 were further examples with various emulsions.
- the emulsions were prepared in a manner similar to the methods used for the production of examples which are outlined on Table C1 noted above.
- the individual samples were contacted to the fabric by methods known to the art, so that the fabric had a 56% wet pick-up of the fluid and each of the individual samples were evaluated for the following physical characteristics: tensile strength according to the AATCC test protocol, "hand” using a four point scale, wherein a value of 1 is indicative of superior "hand” characteristics, and a value of 4 is indicative of poor "hand” characteristics, "Hunter whiteness”, wrinkle recovery according to the AATCC test protocol, the Stoll flex in both the warp and fill directions of the fabric samples, and the tear strength in both the warp and fill directions of the fabric samples.
- Table TS-2 The results of the testing of the fabric samples utilizing the compositions described on Table TS-1 is outlined on Table TS-2 below.
- compositions utilizing the coemulsions all show tensile strength properties, Hunter Whiteness values, and wrinkle recovery values which are comparable to the samples of a single constituent emulsion, namely T6-T8, T14-T16.
- T6-T8 T6-T8
- wrinkle recovery values which are comparable to the samples of a single constituent emulsion, namely T6-T8, T14-T16.
- compositions denoted as T1-T16 were also evaluated in conjunction with a fabric panels of
- the fabric panels were prepared in accordance with the fabric panels listed on Table TS-l.
- the lubricated fabric panels were tested using 16/1 needles on a Singer model 282 sewing machine operating at a rate of 5000 stitches per minute running through 4 folds of fabric through 4 passes. The observed
- coemulsions according to the instant invention provide compositions useful as processing aid for for improving fabric, thread and paper processing characteristics, particularly in improving the "hand", of textiles treated with the coemulsions taught herein, which provide such improved characteristics with relatively small amounts of amino functional silicone softeners in conjunction with other constituents.
- Such an advance allows for a more cost efficient use of such silicone containing constituents with no compromise in
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Structural Engineering (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Colloid Chemistry (AREA)
- Paints Or Removers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
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Abstract
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US57848690A | 1990-09-07 | 1990-09-07 | |
US578486 | 1990-09-07 | ||
US698230 | 1991-05-10 | ||
US07/698,230 US5238731A (en) | 1991-05-10 | 1991-05-10 | Coemulsification of oxidized polyethylene homopolymers and amino functional silicone fluids |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0547157A1 true EP0547157A1 (fr) | 1993-06-23 |
Family
ID=27077510
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91917878A Withdrawn EP0547157A1 (fr) | 1990-09-07 | 1991-09-05 | Coemulsionnement d'homopolymeres de polyethylene oxyde et de fluides de silicone amino-fonctionnelle |
Country Status (6)
Country | Link |
---|---|
US (1) | USRE35229E (fr) |
EP (1) | EP0547157A1 (fr) |
JP (1) | JPH06501281A (fr) |
KR (1) | KR930702578A (fr) |
CN (1) | CN1058274C (fr) |
WO (1) | WO1992004409A1 (fr) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH685392A5 (de) * | 1992-09-26 | 1995-06-30 | Sandoz Ag | Wässrige Wachs- und Silicon-Dispersionen und Verfahren zu deren Herstellung. |
DE4329244A1 (de) * | 1993-08-31 | 1995-03-02 | Sandoz Ag | Wässrige Wachs- und Silicon-Dispersionen, deren Herstellung und Verwendung |
DE4433597C2 (de) * | 1993-09-28 | 1996-10-02 | Clariant Finance Bvi Ltd | Verfahren zur Erhöhung der Naßgleitfähigkeit von Textilmaterial und Naßgleitmittel dafür |
US5478880A (en) * | 1994-02-01 | 1995-12-26 | Moore Business Forms, Inc. | Printable release |
AU714153B2 (en) * | 1994-02-01 | 1999-12-23 | Moore North America, Inc. | Printable release compositions for adhesive articles |
DE4403478A1 (de) * | 1994-02-04 | 1995-08-10 | Basf Ag | Verfahren zur Erzeugung von Drucken nach dem Offset-Heatset-Verfahren |
ES2109144B1 (es) * | 1994-10-28 | 1998-08-16 | Productes Del Latex S A | Composicion para el recubrimiento de articulos de goma o latex. |
US6143812A (en) * | 1998-08-25 | 2000-11-07 | Wacker Silicones Corporation | Asphalt release agents and use thereof |
CA2327034C (fr) | 1999-12-01 | 2007-07-17 | Canon Kabushiki Kaisha | Methode pour refaire la surface d'un element, element a la surface refaite, methode de production d'elements a la surface refaite, liquide de traitement de surface pour obtenir une surface refaite et methode de production du liquide de traitement de surfaces |
CA2327067A1 (fr) | 1999-12-06 | 2001-06-06 | Canon Kabushiki Kaisha | Corps de fibres a surface reformee, reservoir utilisant un absorbeur a fibres, et methode de fabrication d'absorbeur a fibres pour l'ejection de liquide |
DE10015174A1 (de) * | 2000-03-27 | 2001-10-04 | Basf Ag | Stabile wäßrige Polymeremulsionen, ihre Herstellung und Verwendung |
US6649692B2 (en) | 2001-02-20 | 2003-11-18 | Crompton Corporation | Organopolysiloxane composition, emulsion-forming concentrates and aqueous emulsions formed therefrom and use of the emulsions in the treatment of textiles |
US6576087B1 (en) * | 2001-11-15 | 2003-06-10 | Kimberly-Clark Worldwide, Inc. | Soft absorbent tissue containing polysiloxanes |
US6582558B1 (en) | 2001-11-15 | 2003-06-24 | Kimberly-Clark Worldwide, Inc. | Soft absorbent tissue containing hydrophilic polysiloxanes |
US20040023818A1 (en) * | 2002-08-05 | 2004-02-05 | Nguyen Philip D. | Method and product for enhancing the clean-up of hydrocarbon-producing well |
US7140153B1 (en) * | 2002-08-26 | 2006-11-28 | Davinci Roofscapes, Llc | Synthetic roofing shingles |
WO2004113436A1 (fr) * | 2003-06-24 | 2004-12-29 | Polymers Australia Pty. Limited | Agents dispersants acryliques en nanocomposites |
US11174200B2 (en) | 2017-09-13 | 2021-11-16 | Honeywell International Inc. | Stable asphalt emulsions, methods of forming the same, and composite structures formed from the same |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3904805A (en) * | 1973-01-22 | 1975-09-09 | Union Carbide Corp | Sizing organic fibers |
JPS61115988A (ja) * | 1984-11-12 | 1986-06-03 | Mitsubishi Chem Ind Ltd | 撥水剤組成物 |
DK10386A (da) * | 1985-01-10 | 1986-07-11 | United Merchants & Mfg | Vandbaseret klaebemiddelforbindelse af den art, der kan anvendes igen og igen |
US4767646A (en) * | 1985-10-24 | 1988-08-30 | Allied Corporation | Wet abrasion resistant yarn and cordage |
DE3542725A1 (de) * | 1985-12-03 | 1987-06-04 | Hoffmann Staerkefabriken Ag | Waeschenachbehandlungsmittel |
US4935464A (en) * | 1987-04-30 | 1990-06-19 | Toray Silicone Company Limited | Organopolysiloxane microemulsion, process for its production and application thereof |
GB8815162D0 (en) * | 1988-06-25 | 1988-08-03 | Avery International Corp | Improvements relating to release liners |
DE4007136A1 (de) * | 1989-08-05 | 1991-09-12 | Pfersee Chem Fab | Zusammensetzung in form einer waessrigen dispersion und verfahren zur behandlung von fasermaterialien |
-
1991
- 1991-08-31 CN CN91108645A patent/CN1058274C/zh not_active Expired - Fee Related
- 1991-09-05 KR KR1019930700679A patent/KR930702578A/ko not_active Application Discontinuation
- 1991-09-05 JP JP3516687A patent/JPH06501281A/ja active Pending
- 1991-09-05 WO PCT/US1991/006342 patent/WO1992004409A1/fr not_active Application Discontinuation
- 1991-09-05 EP EP91917878A patent/EP0547157A1/fr not_active Withdrawn
-
1995
- 1995-03-22 US US08/408,502 patent/USRE35229E/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO9204409A1 * |
Also Published As
Publication number | Publication date |
---|---|
JPH06501281A (ja) | 1994-02-10 |
CN1059539A (zh) | 1992-03-18 |
CN1058274C (zh) | 2000-11-08 |
USRE35229E (en) | 1996-05-07 |
KR930702578A (ko) | 1993-09-09 |
WO1992004409A1 (fr) | 1992-03-19 |
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