US3567499A - Textile materials and the process for finishing the same - Google Patents
Textile materials and the process for finishing the same Download PDFInfo
- Publication number
- US3567499A US3567499A US672718A US3567499DA US3567499A US 3567499 A US3567499 A US 3567499A US 672718 A US672718 A US 672718A US 3567499D A US3567499D A US 3567499DA US 3567499 A US3567499 A US 3567499A
- Authority
- US
- United States
- Prior art keywords
- parts
- active hydrogen
- groups
- textile
- aqueous
- 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
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- 239000004753 textile Substances 0.000 title abstract description 41
- 239000000463 material Substances 0.000 title abstract description 33
- 238000000034 method Methods 0.000 title description 25
- 229920001296 polysiloxane Polymers 0.000 abstract description 29
- 229920001577 copolymer Polymers 0.000 abstract description 19
- -1 ISOCYANATO Chemical class 0.000 abstract description 18
- 229920000642 polymer Polymers 0.000 abstract description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 10
- 239000001257 hydrogen Substances 0.000 abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 abstract description 9
- 239000005056 polyisocyanate Substances 0.000 abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 abstract description 8
- 150000002894 organic compounds Chemical class 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 abstract description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 abstract 1
- YXZBWJWYWHRIMU-UBPCSPHJSA-I calcium trisodium 2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate ytterbium-169 Chemical compound [Na+].[Na+].[Na+].[Ca+2].[169Yb].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O YXZBWJWYWHRIMU-UBPCSPHJSA-I 0.000 abstract 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 description 24
- 239000007795 chemical reaction product Substances 0.000 description 23
- 239000004744 fabric Substances 0.000 description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 5
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 5
- 239000004246 zinc acetate Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 229920002239 polyacrylonitrile Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- PGRNEGLBSNLPNP-UHFFFAOYSA-N 1,6-dichloro-3-methylhex-1-ene Chemical compound ClC=CC(C)CCCCl PGRNEGLBSNLPNP-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
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
- D06M15/37—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
- D06M15/653—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain modified by isocyanate compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
-
- 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
- Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
-
- 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
- Y10T442/2352—Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric
Definitions
- the organo polysiloxane is reactive with the isocyanato prepolymer on the textile substrate in order to give the textile material a full pleasantly soft, supple hand and reduce susceptibility to soiling.
- a further object of his invention is to provide textiles having an improved finish, an improved hand, a more supple feel and which have reduced susceptibility to soiling.
- Another object of this invention is to provide an improved method of treating textile materials.
- Still another object of this invention is to provide a method of finishing textiles and the finished textiles which may be based on cotton, cellulose, wool, silk, polyamides, polyurethane, polyesters, polycarbonate, polyacrylonitrile, polypropylene and the like.
- This aqueous bath is used to treat the textile material which may then be dried and subjected to an after treatment with water in order to accelerate the curing of the polyurethane material in conjunction with the organic polysiloxane on the textile substrate.
- the crux of this invention is the use of and reaction of the hydroxy organo polysiloxane with the isocyanato prepolymer in the aqueous bath on the textile substrate since this gives the textile materials an improved hand, better resistance to soiling, and a softer more supple feel than was heretofore known with textiles treated with organo polysiloxane isocyanato prepolymers.
- the invention therefore could be briefly summarized as follows: the process involves treating textile materials with aqueous baths which contain:
- reaction products containing isocyanate groups which reaction products are prepared from organic compounds of molecular weight about 500 to 10,000 containing at least two active hydrogen atoms and organic polyisocyanates, and
- Examples of organic compounds containing at least two active hydrogen containing groups and having a molecular weight of 500 to 10,000 and which are suitable for preparing the reaction products containing isocyanate groups which, to be used according to the invention, are as follows: Polyalkylene glycols such as polyethlene, polypropylene, polybutylene or polyhexylene glycols or copolymers or graft polymers of the alkylene oxides on which these polyglycols are based and polythioetherglycols which are obtainable by condensation of thiodiglycol with itself or with polyalcohols that are free from sulphur.
- Polyalkylene glycols such as polyethlene, polypropylene, polybutylene or polyhexylene glycols or copolymers or graft polymers of the alkylene oxides on which these polyglycols are based and polythioetherglycols which are obtainable by condensation of thiodiglycol with itself or with polyalcohols that are
- Polyesters which are obtained by the condensation of dicarboxylic acids with polyalcohols or by condensation of hydroxycarboxylic acids are also suitable as well as polyester amides such as are described, for example, in US. patent specification No. 2,424,883, and polyacetals such as are described, for example, in US. patent specification No. 3,021,289.
- compounds containing at least two active hydrogen atoms those having two or more free hydroxyl groups are preferably used, but those having free carboxyl, mercapto or amino groups are also suitable.
- the molecular weights of these compounds may be up to 10,000 although the preferred range lies between 750 and 5,000.
- low molecular weight compounds such as diols, for example, 1,4-butanediol, ethylene glycol, diethylene glycol and the like which have a modifying effect on the properties of the end products may also be used.
- Any suitable organic polyisocyanate may be used for the preparation of the reaction products and are preferably aliphatic or cycloaliphatic diisocyanates. Examples of these include tetramethylene diisocyanate, hexamethylene diisocyanate, 1,4-cyclohexane diisocyanate, 4,4-dicyclohexylmethane diisocyanate, 2,4- and 2,6-hexahydrotoluylene diisocyanate and the like.
- Aromatic diisocyanates such as p-phenylene diisocyanate and 2,4- or 2,6- toluylene diisocyanate as well as triisocyanates, such as the reaction product of the formula obtainable by reaction of 3 mols of hexamethylene diisocyanate and 1 mol of water are also suitable.
- the preparation of the reaction products containing isocyanate groups may be performed by reacting the compounds which carry at least two active hydrogen atoms with a stoichiometric excess of polyisocyanate at elevated temperatures.
- the reaction products Which contain isocyanate groups can also be utilized in the form of the known bisulphite addition products.
- the organopolysiloxanes having two active hydrogen atoms that are to be used according to the invention include in particular compounds of the general formula B11810 T in which n is greater than 1 and not more than 3 and in which each substituent R is one of the radicals R, X-Y or Y-XY, where R represents an aliphatic, cycloaliphatic or aromatic hydrocarbon radical which may, if desired, be substituted by an inert substituent, X represents an aliphatic or araliphatic bivalent or trivalent radical which may contain an ether, thioether, ester or amino group, and Y represents a hydroxyl, sulphydryl, carboxyl or carbonamide group or a secondary amino group, with the proviso that at least two siloxane units are of the formulae:
- organopolysiloxanes described above can be used as starting materials for the reaction products containing isocyanate groups which are to be used according to the invention.
- vinyl and divinyl monomers on which the polymers or copolymers to be used according to the invention may be based are as follows: ethylene, propylene, vinyl chloride, vinyl acetate, vinyl ethyl ether, styrene or divinylbenzene, butadiene, isoprene or chloroprene and a,,B-unsaturated carboxylic acids such as acrylic acid and methacrylic acid as well as their nitriles, esters and amides.
- Polymers which contain groups capable of reacting with isocyanates are generally to be preferred; these include, for example, polymers or copolymers prepared from acrylic acid, methacrylic acid, their hydroxyalkyl esters or amides, as well as the copolymers which can be obtained when N-methylolacrylamide, N-methylolrnethacrylamide or their derivatives prepared by reacting them with alcohols containing at least one further functional group are copolymerized with other olefinically unsaturated compounds, e.g. by the process according to US. patent specification No. 3,243,399.
- the proportion of organopolysiloxanes containing at least two active hydrogen atoms may be 1 to 20 equivalents percent, based on the reaction products containing isocyanate groups, provided that each isocyanate group is capable of reacting with one of the active hydrogen atoms of the organopolysiloxanes.
- the ratio usually lies between 3 and 7 equivalents percent.
- the ratio by weight between the reaction products which contain isocyanate groups and the polymers or cpolymers which may be used is preferably between 0.25 :1 and 4: 1.
- the amount of reaction products containing isocyanate groups, organopolysiloxanes and, where present polymers or copolymers contained in the aqueous bath may also vary within wide limits, for example somewhere between 20 and 300 grams/liter. The most suitable concentration in the bath and the appropriate proportions of the individual components to each other can easily be determined from case to case by preliminary tests.
- the impregnating baths can be prepared by emulsifying the reaction products which carry isocyanate groups and the organopolysiloxanes which have at least two active hydrogen atoms and which have been adjusted, if necessary, to a low viscosity by the addition of inert solvents that are immiscible with water, such as benzene, toluene, ethyl acetate, petrol or chlorinated hydrocarbons, by means of a high speed stirrer in water in which suitable emulsifiers such as alkylphenolpolyglycol ethers, commercial parafiin sulphonates, alkyl benzene sulphonates or the alkali salts of acid sulphur acid esters of higher aliphatic alcohols are dissolved in quantities of 0.5 to 10% by weight.
- inert solvents such as benzene, toluene, ethyl acetate, petrol or chlorinated hydrocarbons
- two emulsions each of which contains one of the components, may first be prepared separately and then combined, if desired with the addition of the polymers or copolymers in the form of their aqueous dispersions.
- both components may be stirred successively into the same aqueous emulsifier solution by means of a high speed stirrer, and the polymer or copolymer emulsion may then be added to this emulsion.
- a third method of preparation is possible with the use of polymers or copolymers.
- a stable emulsion is first prepared from the organopolysiloxane and the polymer or copolymer emulsions, and this is then mixed with the emulsion of isocyanate groupcontaining reaction products, which last mentioned emulsion is prepared shortly before use. If desired the baths may then be diluted with water.
- the treatment of the textile materials with the aqueous baths to be used according to the invention may be performed by steeping the textile materials in the baths and then squeezing them out or centrifuging them to reduce the weight increase to about 40 to 150%, preferably 70 to 100%, and then drying.
- the aqueous bath may be sprayed on to the textile material which is then dried.
- it is advisible to store the materials for a few days at room temperature after the treatment.
- the process of storing the finished textile materials for several days, a process which is to be recommended especially in cases where less highly reactive, aliphatic isocyanates are used, can be shortened or even avoided by accelerating the reaction between the isocyanate groups and the compounds which contain active hydrogen atoms.
- 0.1 to 10 grams/liter of water-soluble salts of metals of sub-Group I, II or VIII of the Periodic System of elements with lower aliphatic carboxylic acids are added to the aqueous bath.
- the textile materials are impregnated and dried and this operation may be followed by a 3 to 30 minutes after-treatment in water at 10 to 100 C. which water may contain surface-active substances, 1 to 5 grams of hydrogen peroxide (30%) or 0.1 to 1 g. of catalysts which accelerate the isocyanate reaction with compounds containing active hydrogen atoms being added per liter of water at temperatures below 60 C.
- the after-treatment may also be performed by treating the impregnated and dried textile materials with steam at to C. for /2 to 10 minutes.
- Zinc salts of lower carboxylic acids are particularly suitable salts to add to the bath.
- Suitable catalysts for the after treatment are, for example, tin compounds such as dibutyl tin dilaurate or dimaleate, aqueous solutions of stannous chloride stabilized with glycollic acid, tertiary amines such as triethylamine, dimethylcyclohexylamine, triethylenediamine and N-ethylmorpholine or the acetyl acetonates of nickel, cobalt or iron.
- the process according to the invention makes it possible to obtain excellent finishes on textile materials of natural or synthetic origin, for example textile materials of cotton, regenerated cellulose, wool or silk as well as of polyamide, polyurethane, polyester, polycarbonate, polyacrylonitrile or polypropylene fibers, especially from the point of view of their crease resistance, abrasion resistance and dimensional stability.
- the treated textile materials are distinguished by a full, pleasant, soft and supple handle and an increased dirt repellency.
- the treated textiles are useful to make clothing such as trousers, coats and the like.
- EXAMPLE 1 A blended fabric of about 55% polyacrylonitrile fibers and about 45% wool was treated with an aqueous bath which contained, per liter, about 20 parts of an emulsion of a reaction product containing isocyanate groups, about 15 parts of the mixture of an emulsion of an organopolysiloxane with the aqueous dispersion of a coploymer and about 0.3 part of zinc acetate.
- the blended fabric of polyacrylonitrile fibers and wool was squeezed out to a bath uptake of about 90%, dried for about 10 minutes at 110 C. and then treated for up to about 1 minute with steam at 102 C.
- the fabric, treated according to the invention has a soft, smooth handle and the following advantages compared to an untreated fabric:
- the emulsion of the reaction product containing isocyanate groups was prepared as follows:
- the mixture of the emulsion of an organopolysiloxane with the dispersion of a copolymer was prepared as follows:
- Dry creasing angle Wet creasing angle formula 5 Warp Weft Warp HOCH Si(CH ⁇ O-Si(CH & I Untreated fabric 102 105 65 70 OeSHCHQFCHZOH aarzarrara was emulsified with about 596 parts or water which con- 0 0 0 tained about 4 parts of the sodium salt of an alkyl Fabric treated with 100 g.
- the cotton 1 f T? f f 1 fabric treated according to the invention has a smooth, and i i part 0 Zmc acetate abnc 0 Po soft handle and a high wet creasing angle in addition to acrylommle fibers was Squeeze? out to a bath p? good abrasion resistance. The effects are largely resistant about dned t about 130 and then ticated wlth to Washing steam at about 102 C. for up to about 2 minutes.
- the fabric treated according to the invention has a pleasant, smooth handle and improved response to creasing.
- the fabric was Excess diisocyanate was then removed at about 160 squeezed out to a bath uptake of about 100%, dried at C. in a thin layer evaporator at about 0.1 mm. Hg: A 50% about 100 C. and then heated afterwards at C. for emulsion was then prepared from about 500 parts of the 5 minutes.
- the rayon fabric treated according to the inresulting reaction product which contained about 5.7%
- vention has a full, smooth Wool-like handle, good abrasion 75 by weight of free isocyanate groups, with the use of about 9 100 parts of ethyl acetate and about 400 parts of water with the addition of a commercial surface-active parafiin sulphonate.
- the yarns were treated with the aqueous bath by immersion contrifuged to reduce the bath uptake to about 60% and dried at about 130 C.
- the yarns treated according to the invention have a pleasant, soft handle and do not tend to felt or shrink when washed.
- the process for finishing a textile material to impart an improved hand and a reduced susceptibility to soiling which comprises treating a textile material with an aqueous bath which consists of essentially of 1) an isocyanato prepolymer prepared by a process which comprises reacting an organic polyisocyanate with an organic compound having a molecular weight of about 500 to about 10,000 and containing at least two active hydrogen containing groups as determined by the Zerewitinoif method (2) and 1 to 20 equivalent percent, based on said prepolymer of an organopolysiloxane having a molecular weight of up to about 25,000 and containing at least two active hydrogen containing groups as determined by the Zerewitinoff method; and reacting said prepolymer (1) and said polysiloxane (2) in situ on said textile material.
- said aqueous bath additionally contains 0.1 to g. per liter of water-soluble lower carboxylic acid salts of metals of Groups I, II or VIII, of the Periodic System of elements, and wherein after treating with said aqueous bath; said textile material is dried and then treated for 3 to 30 minutes in water at 10100 C. or for /2-10 minutes with steam at 100- 110 C., said water optionally including 1-5 g. of hydrogen peroxide or 0.1-l g. of catalysts which accelerate the reaction of isocyanate groups with compounds containing active hydrogen atoms.
- a textile material treated according to the process of claim 1 wherein said aqueous composition also contains 0.1-10 g. per liter of a water-soluble lower carboxylic acid salt of a metal of Groups I, II, or VIII of the Periodic System of elements.
- organopolysiloxane has the general formula RuSiO in which n is greater than 1 and not more than 3 and in which each substituent R is one of the radicals R, -XY, or
- R, Y and X have the meaning indicated above and m is the integer 1 or 2, and the substituents R in the remaining siloxane units being exclusively the radicals R.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0050369 | 1966-10-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3567499A true US3567499A (en) | 1971-03-02 |
Family
ID=7103748
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US672718A Expired - Lifetime US3567499A (en) | 1966-10-06 | 1967-10-04 | Textile materials and the process for finishing the same |
Country Status (8)
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3668228A (en) * | 1968-06-13 | 1972-06-06 | Ciba Ltd | Solutions of curing catalysts for polysiloxanes |
US3852230A (en) * | 1970-10-14 | 1974-12-03 | Vyzk Ustav Kozedelny | Impregnating compositions for fibrous sheet materials from polyurethane and olefin copolymer |
US4052495A (en) * | 1975-05-19 | 1977-10-04 | Dow Corning Corporation | Method of obtaining release of polyurethane polymers and compositions therefor |
US4057595A (en) * | 1975-05-19 | 1977-11-08 | Dow Corning Corporation | Method of modifying the physical properties of urethane elastomers |
US4137360A (en) * | 1973-09-07 | 1979-01-30 | Bayer Aktiengesellschaft | Microporous sheets and a process for making them |
US4468492A (en) * | 1983-07-15 | 1984-08-28 | Ppg Industries, Inc. | Polymeric organo functional silanes as reactive modifying materials |
US4528343A (en) * | 1981-06-22 | 1985-07-09 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Antithrombogenic elastomer, molded products of the same, and a process for manufacturing the same |
WO1985005322A1 (en) * | 1984-05-21 | 1985-12-05 | Thoratec Laboratories Corporation | Moisture vapor permeable materials |
WO1985005373A1 (en) * | 1984-05-21 | 1985-12-05 | Thoratec Laboratories Corporation | Moisture vapor permeable materials containing segmented block multipolymer |
US4579964A (en) * | 1983-03-31 | 1986-04-01 | Union Carbide Corporation | Alkoxysilyl functional silicones |
US5120813A (en) * | 1980-02-29 | 1992-06-09 | Th. Goldschmidt Ag | Moisture vapor permeable materials |
US5258443A (en) * | 1990-10-30 | 1993-11-02 | Imperial Chemical Industries, Plc | Curable aqueous composition comprising a high molecular weight silane functional polymer and a relatively low molecular weight silane functional polymer |
US5886082A (en) * | 1995-04-05 | 1999-03-23 | Kansai Paint Co., Ltd. | Aqueous coating composition |
US5910535A (en) * | 1996-05-03 | 1999-06-08 | Decora, Incorporated | Water based coating composition having sacrificial layer for stain removal |
US6084020A (en) * | 1994-08-16 | 2000-07-04 | Decora, Incorporated | Non-stick polymer-coated articles of manufacture, and process and coatings for the production thereof |
US20100267861A1 (en) * | 2007-12-07 | 2010-10-21 | Benecke-Kaliko Ag. | Polymer mixture |
WO2013017033A1 (en) | 2011-07-29 | 2013-02-07 | Dow Corning (China) Holding Co., Ltd. | Coating composition, method for coating surface of material using the same, and surface treated materials having the same |
-
1966
- 1966-10-06 DE DE19661619032 patent/DE1619032A1/de active Pending
-
1967
- 1967-09-28 GB GB44232/67A patent/GB1179310A/en not_active Expired
- 1967-10-04 US US672718A patent/US3567499A/en not_active Expired - Lifetime
- 1967-10-05 SE SE13659/67A patent/SE327387B/xx unknown
- 1967-10-05 FR FR123470A patent/FR1545897A/fr not_active Expired
- 1967-10-05 NL NL6713562A patent/NL6713562A/xx unknown
- 1967-10-06 BE BE704806D patent/BE704806A/xx unknown
- 1967-10-06 CH CH1398867A patent/CH476889A/de not_active IP Right Cessation
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3668228A (en) * | 1968-06-13 | 1972-06-06 | Ciba Ltd | Solutions of curing catalysts for polysiloxanes |
US3852230A (en) * | 1970-10-14 | 1974-12-03 | Vyzk Ustav Kozedelny | Impregnating compositions for fibrous sheet materials from polyurethane and olefin copolymer |
US3900621A (en) * | 1970-10-14 | 1975-08-19 | Vyzk Ustav Kozedelny | Impregnating compositions for fibrous sheet materials |
US4137360A (en) * | 1973-09-07 | 1979-01-30 | Bayer Aktiengesellschaft | Microporous sheets and a process for making them |
US4052495A (en) * | 1975-05-19 | 1977-10-04 | Dow Corning Corporation | Method of obtaining release of polyurethane polymers and compositions therefor |
US4057595A (en) * | 1975-05-19 | 1977-11-08 | Dow Corning Corporation | Method of modifying the physical properties of urethane elastomers |
US5120813A (en) * | 1980-02-29 | 1992-06-09 | Th. Goldschmidt Ag | Moisture vapor permeable materials |
US4686137A (en) * | 1980-02-29 | 1987-08-11 | Thoratec Laboratories Corp. | Moisture vapor permeable materials |
US4623347A (en) * | 1981-06-22 | 1986-11-18 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Antithrombogenic elastomer products |
US4528343A (en) * | 1981-06-22 | 1985-07-09 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Antithrombogenic elastomer, molded products of the same, and a process for manufacturing the same |
US4579964A (en) * | 1983-03-31 | 1986-04-01 | Union Carbide Corporation | Alkoxysilyl functional silicones |
US4468492A (en) * | 1983-07-15 | 1984-08-28 | Ppg Industries, Inc. | Polymeric organo functional silanes as reactive modifying materials |
WO1985005373A1 (en) * | 1984-05-21 | 1985-12-05 | Thoratec Laboratories Corporation | Moisture vapor permeable materials containing segmented block multipolymer |
WO1985005322A1 (en) * | 1984-05-21 | 1985-12-05 | Thoratec Laboratories Corporation | Moisture vapor permeable materials |
US5258443A (en) * | 1990-10-30 | 1993-11-02 | Imperial Chemical Industries, Plc | Curable aqueous composition comprising a high molecular weight silane functional polymer and a relatively low molecular weight silane functional polymer |
US6084020A (en) * | 1994-08-16 | 2000-07-04 | Decora, Incorporated | Non-stick polymer-coated articles of manufacture, and process and coatings for the production thereof |
US6120849A (en) * | 1994-08-16 | 2000-09-19 | Decora, Incorporated | Process for producing coated articles of manufacture |
US6153304A (en) * | 1994-08-16 | 2000-11-28 | Decora Incorporated | Hydrophobic coating system for application to an inorganic, organic or metallic substrate |
US5886082A (en) * | 1995-04-05 | 1999-03-23 | Kansai Paint Co., Ltd. | Aqueous coating composition |
US5910535A (en) * | 1996-05-03 | 1999-06-08 | Decora, Incorporated | Water based coating composition having sacrificial layer for stain removal |
US20100267861A1 (en) * | 2007-12-07 | 2010-10-21 | Benecke-Kaliko Ag. | Polymer mixture |
US8314179B2 (en) * | 2007-12-07 | 2012-11-20 | Benecke-Kaliko Ag | Polymer mixture |
WO2013017033A1 (en) | 2011-07-29 | 2013-02-07 | Dow Corning (China) Holding Co., Ltd. | Coating composition, method for coating surface of material using the same, and surface treated materials having the same |
EP2736961A4 (en) * | 2011-07-29 | 2015-01-14 | Dow Corning China Holding Co Ltd | COATING COMPOSITION, METHOD FOR SURFACE COATING OF MATERIALS THEREFOR AND SURFACE-COATED MATERIALS THEREWITH |
Also Published As
Publication number | Publication date |
---|---|
CH476889A (de) | 1969-09-30 |
FR1545897A (fr) | 1968-11-15 |
NL6713562A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-04-08 |
DE1619032A1 (de) | 1969-10-30 |
SE327387B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-08-24 |
BE704806A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-02-15 |
CH1398867A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-04-30 |
GB1179310A (en) | 1970-01-28 |
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