US3345318A - Vinyl acetate-ethylene-n-methylol acrylamide interpolymer latex and woven fabrics coated thereby - Google Patents
Vinyl acetate-ethylene-n-methylol acrylamide interpolymer latex and woven fabrics coated thereby Download PDFInfo
- Publication number
- US3345318A US3345318A US444375A US44437565A US3345318A US 3345318 A US3345318 A US 3345318A US 444375 A US444375 A US 444375A US 44437565 A US44437565 A US 44437565A US 3345318 A US3345318 A US 3345318A
- Authority
- US
- United States
- Prior art keywords
- ethylene
- vinyl acetate
- latex
- methylol acrylamide
- interpolymer
- 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
Links
- 239000004816 latex Substances 0.000 title claims description 43
- 239000002759 woven fabric Substances 0.000 title claims description 25
- 229920002554 vinyl polymer Polymers 0.000 title claims description 13
- 229920000126 latex Polymers 0.000 title description 50
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 37
- 239000005977 Ethylene Substances 0.000 claims description 37
- 238000006116 polymerization reaction Methods 0.000 claims description 29
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 28
- 239000011248 coating agent Substances 0.000 claims description 24
- 238000000576 coating method Methods 0.000 claims description 24
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 12
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims 1
- -1 peroxide compounds Chemical class 0.000 description 41
- 239000004744 fabric Substances 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 19
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 16
- 239000003995 emulsifying agent Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 239000002245 particle Substances 0.000 description 15
- 239000003381 stabilizer Substances 0.000 description 13
- 239000000084 colloidal system Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000012190 activator Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- 229920001983 poloxamer Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- HDERJYVLTPVNRI-UHFFFAOYSA-N ethene;ethenyl acetate Chemical compound C=C.CC(=O)OC=C HDERJYVLTPVNRI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229920002114 octoxynol-9 Polymers 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001993 poloxamer 188 Polymers 0.000 description 2
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- FSWLUYQMFPBXSH-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-1,1-diol Chemical compound CC(C)CC(C)C#CC(C)CC(C)C(O)O FSWLUYQMFPBXSH-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920006197 POE laurate Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229940117913 acrylamide Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- QGKLCGVVGGFZBS-UHFFFAOYSA-N formaldehyde;zinc Chemical compound [Zn].O=C QGKLCGVVGGFZBS-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229940116335 lauramide Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003784 tall oil Chemical class 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CAAIULQYGCAMCD-UHFFFAOYSA-L zinc;hydroxymethanesulfinate Chemical compound [Zn+2].OCS([O-])=O.OCS([O-])=O CAAIULQYGCAMCD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/04—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06N3/042—Acrylic polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloylmorpholine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/587—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives characterised by the bonding agents used
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/64—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives the bonding agent being applied in wet state, e.g. chemical agents in dispersions or solutions
-
- 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
- Y10T442/2221—Coating or impregnation is specified as water proof
- Y10T442/2246—Nitrogen containing
-
- 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
- Y10T442/2549—Coating or impregnation is chemically inert or of stated nonreactance
- Y10T442/2566—Organic solvent resistant [e.g., dry cleaning fluid, etc.]
Definitions
- This invention relates to the treatment of woven fabrics and is more particularly concerned with the application to woven fabrics of a water-resistant and solvent-resistant coating finish to improve the body and drape of the fabrics.
- the coating, e.g. back coating, and finishing of woven fabrics are well-known operations and various compositions for such use have been proposed and are used in practice.
- Attempts to meet these requirements has ioften involved the provision of relatively complex and expensive compositions which necessarily increase the cost of the finished product.
- woven fabrics whether formed from natural fibers such as cotton, wool, linen and the like, or from synthetic fibers such as cellulose acetate, nylon, Dacron, and the like, or of mixtures of natural and/ or synthetic fibers, are given a desirable body and drape by applying to them a polymeric latex having characteristics which will be described below and drying the latex to remove its liquid component and to leave upon the woven fabrics a deposit of a water-resistant and solvent-resistant polymeric coating.
- the latex used in accordance with the invention contains as the polymeric component an interpolymer of vinyl acetate and ethylene copolymerized with N-methylol acrylamide which is effective to polymerize and to crosslink with the initial vinyl acetate and ethylene containing interpolymer under the action of heat.
- the abovedescribed composition is applied to the woven fabric web in the form of an aqueous latex containing the interpolymer of vinyl acetate, ethylene and copolymerized N- methylol acrylamide in the dispersed phase.
- the vinyl acetate-ethylene-N-methylol acrylamide interpolymer is characterized by an ethylene content of to 40%, preferably 16 to 40%, a particle size of 0.1 to 2 preferably 0.1 to 0.25 and an intrinsic viscosity of 1 to 2.5 dl./g.
- the amount of N-methylol acrylamide is 0.5 to 10% on the vinyl acetate.
- composition is readily prepared by the interpolymerization of vinyl acetate, ethylene and N-methylol acrylamide in an aqueous dispersion system.
- the N-methylol acrylamide readily copolymerizes with the vinyl acetate and the ethylene to form an interpolymer or'terpolymer but, as mentioned, is adapted to undergo further reaction after this initial polymerization upon the application of ing agent, at a pH of 2 to 6, the catalyst being added incrementally.
- the process is a batch process which involves first a homogenization period in which the vinyl acetate suspended in water is thoroughly agitated in the presence of ethylene under the working pressure to effect solution of the ethylene in the vinyl acetate up to the substantial limit of its solubility under the conditions existing in the reaction zone, while the vinyl acetate is gradually heated to polymerization temperature.
- the homogenization period is followed by a polymerization period during which the catalyst, which consists of a main catalyst or initiator, and may include an activator, is added incrementally, and the N-methylol acrylamide is similarly added incrementally, the pressure in the system being maintained substantially constant by application of a constant ethylene pressure.
- Suitable free-radical forming catalysts can be used in carrying out the polymerization of the monomers, such as peroxide compounds. Combination type catalysts employing both reducing agents and oxidizing agents can also be used. The use of this type of combined catalyst is generally referred to in the art as redox polymerization or redox system.
- the reducing agent is also often referred to as an activator and the oxidizing agen as an initiator. Suitable reducing agents or activators include bisulfites, sulfoxylates, or other compounds having reducing properties such as ferrous salts, and tertiary aromatic amines, e.g. N,N-dimethyl aniline.
- the oxidizing agents or initiators include hydrogen peroxide, organic peroxides such as benzoyl peroxide, t-butyl hydroperoxide and the like, persulfates, such as ammonium or potassium persulfate, perborates, and the like.
- Specific combination type catalysts or redox systems which can be used include hydrogen peroxide and zinc formaldehyde sulfoxylate; hydrogen peroxide, ammonium persulfate, or potassium persulfate, with sodium metabisulfite, sodium bisulfite, ferrous sulfate, dimethyl aniline, zinc formaldehyde :sulfoxylate or sodium formaldehyde sulfoxylate,
- Other types of catalysts that are well-known in the art can also be used to polymerize the monomers, such as the peroxide compounds, with or without the addition of reducing agents or other activating materials.
- Redox catalyst systems are described, for example, in Fundamental Principles of Polymerization by G. F. DAlelio (John Wiley and Sons, Inc., New York, 1952) pp. 333 et seq.
- Other types of catalysts that are well known in the art can also be used to polymerize the monomers according to this invention, with or without the addition of reducing agents or other activating materials.
- the catalyst is employed in the amount of 0.1 to 2%, preferably 0.25 to 0.75%, based on the weight of vinyl acetate introduced into the system.
- the activator is ordinarily added in aqueous solution and the amount of activator is generally 0.25 to 1 times the amount of catalyst.
- emulsifying agents which are suitably used are non-ionic.
- Suitable non-ionicemulsifying 1 agents include polyoxyethylene condensates.
- Polyoxyethylene condensates may be represented by the general formula:
- R is the residue of a fatty alcohol containing 10-18 carbon atoms, an alkyl phenol, a fatty acid containing 10-18 carbon atoms, an amide, an amine, or a mercaptan, and where n is an integer of 1 or above.
- polyoxyethylene condensates which can be used include polyoxyethylene aliphatic ethers such as polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene hydroabietyl ether and the like; polyoxyethylene alkaryl ethers such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether and the like; polyoxyethylene esters of higher fatty acids such as polyoxyethylene laurate, polyoxyethylene oleate and the like as well as condensates of ethylene oxide with resin acids and tall oil acids; polyoxyethylene amide and amine condensates such as N-polyoxyethylene lauramide, and N-lauryl-N-polyoxyethylene amine and the like; and polyoxyethylene thio-ethers such as polyoxyethylene ndodecyl thio-ether.
- polyoxyethylene aliphatic ethers such as polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene hydro
- the non-ionic emulsifying agents which can be used according to this invention also include a series of surface active agents known as Pluronics.
- the Pluronics have the general formula:
- a, b, and c are integers of 1 or above. As b increases, the compounds become less water soluble or more oil soluble and thus more hydrophobic when a and remain substantially constant.
- acetylenic glycols sold commercially under the name Surfynois.
- This class of compounds can be represented by the formula in which R and R are alkyl radicals containing from 3 to carbon atoms, R and R are selected from the group consisting of methyl and ethyl, x and y have a sum in the range of 3 to 60, inclusive.
- non-ionic emulsifying agents which can be used are as follows:
- a polyoxyethylene nonylphenyl ether having a cloud point of between 126 and 133 F. is marked under the trade name Igepal CO-630 and a polyoxyethylene nonylphenyl ether having a cloud point above 212 F. is marketed under the trade name Igepal CO-887.
- a similar polyoxyethylene nonylphenyl ether having a cloud point of about 86 F. is marketed under the trade name Igepal CO610.
- a polyoxyethylene octylphenyl ether having a cloud point of between 80 F. and 160 F. is marketed under the trade name Triton X-100.”
- a polyoxyethylene oleyl ether having a cloud point of between 80 F. and 160 F. is marketed under the trade named Atlas G-39l5 and a polyoxyethylene lauryl ether having a cloud point above 190 F. is marketed under the trade name Brij 35.
- a polyoxypropylene having a cloud point of about 140 F. is marketed under the trade name Pluronic L-64, and a polyoxypropylene having a cloud point of about 212 F. is marketed under the trade name Pluronic F-68.
- Pulr-onic L-64 is a polyoxyethylene-polyoxypropylene glycol conforming to the above general formula for Pluronics in which the polyoxypropylene chain has a molecular weight of 1500 to 1800 and the polyoxyethylene content is from 40 to 50 percent of the total weight of the molecule.
- Pluronic F-68 is a polyoxyethylene-polyoxypr-opylene glycol con-forming to the above general formula for 'Pluronics in which the polyoxypropylene chain has a molecular weight of 1500 to 1800 and the polyoxyethylene content is from 80 to 90 percent of the total weight of the molecule.
- the polyoxypropylene Pluronics are obtained by condensing ethylene oxide on the polyoxypropylene base and the hydrophobichydrophilic nature of the resulting compound is controlled by varying the molecular weight of either the hydrophobic base or the hydrophilic portion of the molecule.
- Surfynols are Surfynol 465 which is an ethylene oxide adduct of 2,4,7,9-tetramethyl decynediol containing an average of 10 moles of ethylene oxide per mole, and Surfynol 485 which corresponds to Surfynol 465 but contains an average of 30 moles of ethylene oxide per mole.
- Surfynol 465 has a cloud point of about F. and Surfynol 485 has a cloud point above 212 F.
- cloud points recited are based on 1% aqueous solutions.
- a single emulsifying agent can be used, or the emulsifying agents can be used in combination.
- a relatively hydrophobic agent is one having a cloud point in 1% aqueous solution below F.
- a relatively hydrophilic agent is one having a cloud point in 1% aqueous solution of 190 F. or above.
- the concentration range of the total amount of emulsifying agents useful is from 0.5 to 5% based on the aqueous phase of the latex regardless of the solids content.
- Latex stabilizers are also advantageously used.
- the stabilizers employed are, in part, governed by the use to which the copolymer latex is to be put, and/ or the particle size of the copolymer.
- the vinyl acetate ethylene copolymer latices prepared by the method described can have various average particle size ranges.
- an ethylenically-unsaturated acid having up to 6 carbon atoms is advantageously used as the stabilizer.
- Typical acids of this character are acrylic acid, methacrylic acid, itaconic acid, maleic acid, vinyl sulfonic acid and the like. These unsaturated acids impart increased stability to the latices. They tend to copolymerize with the monomers in the system.
- the amount of unsaturated acid used is suitably 0.1 to 3% based on vinyl acetate, preferably 0.2 to 1%.
- a protective colloid can be used in the polymerization mixture as the stabilizing agent, although an unsaturated acid can be used if desired.
- Various amounts of colloids can be incorporated into the latices as desired, but it is preferred to maintain the colloid concentration at the lowest level possible. The amount of colloid used will also depend upon the particular colloid employed. Colloids of higher molecular Weight tend to produce a latex of a higher viscosity than like amounts of a lower molecular weight colloid. Other properties of the colloids aside from their molecular weight also affect the viscosity of the latices and also the properties of the films formed therefrom. It is advantageous to maintain the colloid content of the latices between about 0.05 and 2% by weight based on the total latex, and that hydroxyethyl cellulose is a particularly advantageous colloid when used in the latices.
- colloids can also be used, including polyvinyl alcohol, partially-acetylated polyvinyl alcohol, e.g. up to 50% acetylated, casein, hydroxyethyl starch, carboxymethyl cellulose, gum arabic, and the like, as known in the art of synthetic polymer latex technology.
- an alkaline buffering agent of any convenient type. Any alkaline material which is compatible with the stabilizing agent can be used as the buffer.
- the amount of buffer is that sufiicient to adjust the pH of the system within the desired range. Am monium and sodium bicarbonate are preferred buffer because of their compatibility with the system and their low cost.
- the amount of buffer is generally about 0.1 to 0.5% by weight, based on the monomers. Other buffers such as disodium phosphate, sodium acetate, and the like, can, however, also be used.
- reaction temperatures for polymerizing vinyl acetate than have heretofore been feasible economically can also be used.
- the use of lower reaction temperatures has been found to result in higher molecular weight vinyl acetate copolymers.
- the reaction temperature can be controlled by the rate of catalyst addition and by the rate of the heat dissipation therefrom. Generally we have found that it is advantageous to maintain a mean temperature of about 50 C. during the polymerization of the monomers and to avoid temperatures much in excess of 80 C. While temperatures as low as 0 can be used, economically the lower temperature limit is about30 C.
- reaction time will also vary depending upon other variables such as the temperature, the catalyst, and the desired extent of the polymerization. It is generally desirable to continue the reaction until less than 0.5% of the vinyl acetate and N-methylol acrylamide remains unreacted. Under these circumstances, a reaction time of about 6 hours has been found to be generally sufficient for complete polymerization, but reaction times ranging from 3 to 10 hours have been used, and other reaction times can be employed, if desired.
- a substantial amount of the vinyl acetate is initially charged to the polymerization vessel and saturated with ethylene in the manner discussed above. Most advantageously, at least about 75% of the total vinyl acetate to be polymerized is initially charged, preferably at least about 85%, and the remainder of the vinyl acetate is incrementally added during the course of the polymerization.
- the charging of all of the vinyl acetate initially is also contemplated, with no additional incremental supply.
- the quantity of ethylene entering into the copolymer is influenced by the pressure, the agitation, and the viscosity of the polymerization medium.
- pressures in excess of 100 atms. are not required.
- a pressure of at least about 10 atms. is most suitably employed.
- a high degree of agitation should be employed, and high viscosities should be avoided, a low viscosity being preferred.
- a viscosity of 30 to 150 centipoises is con sidered a low viscosity
- a viscosity of 151 to 800 centipoises is considered a medium viscosity
- a viscosity of 801 to 3000 centipoises is considered a high viscosity.
- the process of forming the vinyl acetate-ethylene-N- methylol acrylamide interpolymer latices generally com prises the preparation of an aqueous solution containing at least some of the emulsifying agent and stabilizer, and the pH bufiering system.
- This aqueous solution and the initial charge of vinyl acetate are added to the polymerization vessel and ethylene pressure is applied to the desired value.
- the mixture is thoroughly agitated to dissolve ethylene in the vinyl acetate and in the water phase, agitation being continued until substantial equilibrium is achieved. This generally requires about minutes. However, less time may be required depending upon the vessel, the efficiency of agitation, the
- the charge is brought to polymerization temperature during this agitation period. Agitaton can be effected by shaking, by means of an agitator, or other known mechanism.
- the polymerization is then initiated by introducing initial amounts of the catalyst, and of the activator when used. After polymerization has started, the catalyst and the activator are incrementally added as required to continue polymerization, and the N-methylol acrylamide and the remaining vinyl acetate, if any, is similary added.
- reaction is generally continued until the residual vinyl acetate and N-methylol acrylamide content is below 0.5%.
- the completed reaction product is then allowed to cool to about room temperature, while sealed from the atmosphere.
- the pH is then suitably adjusted to a value in the range of 4.5 to 7, preferably 6 to 6.5 to insure maximum stability.
- the particle size of the latex can be regulated by the quantity of non-ionic emulsifying agent or agents employed and by the use or nonuse of a colloidal stabilizing agent.
- a colloidal stabilizing agent to obtain smaller particle sizes, greater amounts of emulsifying agent are used and colloidal stabilizing agents are not employed.
- the total amount of non-ionic emulsifying agent should be at least about 2%, based on the aqueous phase of the latex, and no colloidal stabilizing agent should be used, or if a colloidal stabilizing agent is used, only very small amounts should be employed.
- the ethylene content can be determined by means of the saponification number.
- Intrinsic viscosity is suitably determined by conventional techniques, i.g. in accordance with the procedure described on pages 309-314 of Principles of Polymer Chemistry by Paul J. Flory (Cornell University Press- 1963); using an Ubbelohde (suspended level) viscometer at 30 C.
- the vinyl acetate-ethylene-N-methylol acrylamide interpolymer latex described above is readily applied to a woven fabric to provide a back-coating or similar coating which will give body, 'or fullness, or drape, or like desirable characteristics, to the fabric, e.g. an upholstery fabric, by conventional coating means employed in the woven fabric art.
- a trough contains the latex to be applied and is fitted with a rotatable roll, which is partially immersed in the latex.
- the fabric to be coated is passedacross the 7 upper portion of the roll which is above the level of the latex in the trough but carries a film or coating of the latex which is transferred to the woven fabric in conventional manner.
- Conventional spray apparatus may also be employed, or the latex may be applied in any other convenient manner.
- the latex is suitably at a temperature of the order of 120 to 140 F. while it is in the licker-on trough and is being applied to the fabric.
- the rate of application can be readily controlled in known manner and the quantity applied to the fabric will depend upon individual conditions and the individual fabric being treated. Ordinarily, for service as a back-coating, the latex is applied at such a rate that the solids content of the coating is of the order of -6% based on the weight of the fabric.
- the solids content of the latex itself can also vary, but it is generally advantageous to have a solids content of the order of 50%. If the latex, as produced, has a higher solids content, or if an even lower solids content is desired, the appropriate solids content can readily be attained by appropriate dilution of the latex with water.
- the fabric is subjected to a drying stage and a curing stage.
- the drying stage is ordinarily carried out at a temperature of the order of 240 to 250 F. for a period of time of the order of 2 minutes, and the curing stage is conveniently carried out at a temperature in the neighborhood of 300 to 300 F. for a period of time of the order of 3 minutes.
- other time-temperature relationship can be employed, as is well known in the art, shorter times at higher temperatures or longer times at lower temperatures being used.
- the curing step can be carried out at 280 F. for about min. or more.
- economic considerations make the use of excessively long times undesirable, and the upper temperature limit is governed by the nature of the fabric.
- the drying and curing can be effected in a single exposure or step, e.g. at 300 F. for 5-l0 min.
- the N-methylol acrylamide completes its polymerization and cross-links in the resin.
- the latex has mixed with it, before it is applied to the fabric, a suitable catalyst for the N-methylol acrylamide.
- acid catalysts such as mineral acids, e.g. HCl, or organic acids, e.g. oxalic acid, or acid salts such as ammonium chloride, are suitably used, as known in the art.
- the amount of catalyst is generally about 0.5 to 2% of the total resin.
- Woven fabrics coated with the resinous latex described above exhibit the desirable characteristics indicated, and retain these characteristics, since the polymeric coating deposited from the latex will withstand numerous contacts with water or dry cleaning solvents, e.g. chlorinated hydrocarbons.
- Example 1 The following was charged to a 25 gal. stainless steel pressure reactor equipped with temperature controls and After purging with nitrogen and ethylene, 104 g. potassium persulfate was added to the mixture. The agitator was set at 300 rpm. and the kettle pressurized with ethyl cue to 40 atm. After reaching equilibrium and after heating to 50 C. the agitation was reduced to 195 r.p.m. and polymerization was started by adding 20 cc. of a 0.5% solution of Formopon. During the polymerization 2,400 g. of a 60% aqueous solution of N-inethylol acrylamide was added incrementally, in addition to 136 g. of potassium sulfate which was also added incrementally as needed. The polymerization was complete after 4 /2 hrs. The latex was cooled and neutralized with ammonia to a pH of 5. The latex had the following properties:
- the above-described latex was diluted to 10% solids, 2.5% of ammonium chloride (based on the weight of solids) was added, and the latex was applied to an x 80 print cloth fabric. The latex was applied at the rate of about 18% (solids) based on the weight of the fabric. The fabric was then dried and cured on a pin frame at 300 F. for about 6 min.
- the cured fabric was then subjected to a 1-hr. accelerated washing test at a temperature of 160 F., employing an AATCC Launder-Ometer, in accordance with Standard Test Method 61-1962 as set forth on pages B-76 and B-77 of the 1962 Technical Manual of the American Association of Textile Chemists and Colorists, with the sample being tumbled in a stainless steel cylinder containing stainless steel balls and the wash solution.
- the coating was found to be completely intact after the Washing operation.
- Example 2 The above-described procedure with respect to the preparation of a treated fabric were repeated, except that the coating used was a vinyl acetate homopolymer latex initially having a solids content of 48.7 and a pH of 66.5. At the end of the washing test, the fabric retained only a portion of the coating and had failed the test.
- T is the temperature at which the torsional modulus is 135,000 lbs./in. and T the temperature at which the torsional modulus is 10,000 lbs/in. determined according to ASTM-Dl043-61T.
- a coated woven fabric having on at least one face thereof a coating comprising an interpolymer of vinyl acetate-ethylene-N-methylol acrylamide, the ethylene in said interpolymer being, before polymerization, unsubstituted monomeric ethylene and said interpolymer containing 5 to 40% by weight ethylene and the amount of N-methylol acryamide being 0.5 to 10% by weight of the vinyl acetate.
- a coated woven fabric wherein the woven fabric is coated by applying to at least one face thereof a coating resin in a volatile liquid and then heating to remove the liquid
- the improvement which comprises applying in an aqueous medium a coating resin dispersed in said medium consisting essentially of an interpolymer of vinyl acetate-ethylene-N-methylol acrylamide, the ethylene in said interpolymer being, before polymerization, unsubstituted monomeric ethylene and said interpolymer containing 5 to 40% by weight ethylene and the amount of N-methylol acrylamide being 0.5 to 10% by weight of the vinyl acetate.
- a coated woven fabric having on at least one face thereof a coating deposited from a vinyl acetate-ethylene- N-methylol acnyla-rnide interpolymer latex comprising an aqueous medium having colloidally suspended therein a vinyl acetate-ethylene-N-methylol acrylamide interpolymer, the ethylene in said interpolymer being, before polymerization, unsubstituted monomeric ethylene and said interpolymer containing to 40% by weight ethylene and the amount of N-methylol acrylamide being 0.5 to by weight of the vinyl acetate.
- a latex composition effective for application to a woven fabric to form a resin coating thereon comprising an aqueous medium having colloidally suspended therein a vinyl acetate-ethylene-N-methylol acrylamide interpolymer, the ethylene in said interpolymer being, before 10 polymerization,'unsubstituted monomeric ethylene and, said interpolymer containing 5 to 40% by weight ethylene and the amount of N-methylol acrylamide being 0.5 to 10% by weight of the vinyl acetate.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US444375A US3345318A (en) | 1965-03-31 | 1965-03-31 | Vinyl acetate-ethylene-n-methylol acrylamide interpolymer latex and woven fabrics coated thereby |
DE19661619206 DE1619206B2 (de) | 1965-03-31 | 1966-03-30 | Beschichtungslatex fuer gewebte stoffe und dessen verwendung |
FR55689A FR1472857A (fr) | 1965-03-31 | 1966-03-30 | Composition pour étoffes non tissées ou articles analogues et produits obtenus |
GB14360/66A GB1116909A (en) | 1965-03-31 | 1966-03-31 | A polymer latex for coating fabrics |
JP41019724A JPS507192B1 (enrdf_load_stackoverflow) | 1965-03-31 | 1966-03-31 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US444375A US3345318A (en) | 1965-03-31 | 1965-03-31 | Vinyl acetate-ethylene-n-methylol acrylamide interpolymer latex and woven fabrics coated thereby |
Publications (1)
Publication Number | Publication Date |
---|---|
US3345318A true US3345318A (en) | 1967-10-03 |
Family
ID=23764628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US444375A Expired - Lifetime US3345318A (en) | 1965-03-31 | 1965-03-31 | Vinyl acetate-ethylene-n-methylol acrylamide interpolymer latex and woven fabrics coated thereby |
Country Status (4)
Country | Link |
---|---|
US (1) | US3345318A (enrdf_load_stackoverflow) |
JP (1) | JPS507192B1 (enrdf_load_stackoverflow) |
DE (1) | DE1619206B2 (enrdf_load_stackoverflow) |
GB (1) | GB1116909A (enrdf_load_stackoverflow) |
Cited By (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3380851A (en) * | 1965-03-31 | 1968-04-30 | Air Reduction | Nonwoven fabric with vinyl acetateethylene-n-methylol acrylamide interpolymer as binder |
US3459698A (en) * | 1966-01-10 | 1969-08-05 | Gulf Oil Corp | Ethylene - n - methylol acrylamideacrylic ester terpolymers as bonding agents for nonwoven fabrics |
DE2135459A1 (enrdf_load_stackoverflow) * | 1970-07-16 | 1972-01-20 | ||
US3644241A (en) * | 1970-03-11 | 1972-02-22 | Colgate Palmolive Co | Antisoiling aerosol starch prepared from ethoxylated starch and a fluoroacrylate or fluoroalpha substituted acrylate polymer |
US3658570A (en) * | 1969-12-09 | 1972-04-25 | Larry L Crooks | Imparting a satin like finish to one side of a fabric |
US3714099A (en) * | 1970-09-03 | 1973-01-30 | Union Oil Co | Self-crosslinking vinyl acetate-ethylene latexes |
US3714100A (en) * | 1970-09-03 | 1973-01-30 | Union Oil Co | Crosslinkable vinyl acetate latices |
US3714105A (en) * | 1969-11-05 | 1973-01-30 | Borden Inc | Adhesive latexes of vinyl acetate/ethylene/n-methylolacrylamide terpolymers |
DE2202189A1 (de) * | 1972-01-18 | 1973-07-26 | Hoechst Ag | Verfahren zur herstellung von emulgatorfreien polymerisatdispersionen |
US3852233A (en) * | 1971-05-11 | 1974-12-03 | Chase S Tanner Co | Thermosetting vinyl ester-ethylene emulsion copolymers |
US3912674A (en) * | 1973-04-30 | 1975-10-14 | Du Pont | Ethylene copolymer dispersions as water repellent coatings |
DE2512589A1 (de) * | 1975-03-21 | 1976-09-30 | Wacker Chemie Gmbh | Thermisch selbstvernetzende copolymere |
US4001158A (en) * | 1974-01-16 | 1977-01-04 | Chas. S. Tanner Co. | Crushed foam-backed fabrics and emulsions for producing the same |
US4001160A (en) * | 1973-09-26 | 1977-01-04 | Chas. S. Tanner Co. | Aqueous emulsion adhesives based on C2 -C8 ethers of N-methylol amides copolymerized with vinyl esters in the presence of hydroxy functional protective colloids |
DE2551556A1 (de) * | 1975-11-17 | 1977-05-26 | Wacker Chemie Gmbh | Thermisch selbstvernetzende copolymere |
US4075387A (en) * | 1976-06-30 | 1978-02-21 | Celanese Corporation | Non-woven fabric binders |
US4416727A (en) * | 1982-01-11 | 1983-11-22 | Air Products And Chemicals, Inc. | Process for recovering fiber from wet-strength resin coated paper |
US4692366A (en) * | 1986-09-08 | 1987-09-08 | National Starch And Chemical Corporation | Flocking adhesives based on eva-maleate copolymers |
US4698384A (en) * | 1986-02-19 | 1987-10-06 | Air Products And Chemicals, Inc. | Nonwoven binder emulsions of vinyl acetate/ethylene copolymers having improved solvent resistance |
US4737386A (en) * | 1986-09-08 | 1988-04-12 | National Starch And Chemical Corporation | Textile coating composition and textiles coated therewith |
US4740394A (en) * | 1986-09-08 | 1988-04-26 | National Starch And Chemical Corporation | Textile coatings based on eva-maleate copolymers |
US4745025A (en) * | 1986-02-19 | 1988-05-17 | Air Products And Chemicals, Inc. | Nonwoven products bonded with binder emulsions of vinyl acetate/ethylene copolymers having improved solvent resistance |
US4847143A (en) * | 1985-06-04 | 1989-07-11 | Sumitomo Chemical Company, Limited | Binder composition and nonwoven fabrics and impregnated papers using the same |
US4866119A (en) * | 1986-09-08 | 1989-09-12 | National Starch And Chemical Corporation | Textile coatings based on eva-maleate copolymers |
US4892917A (en) * | 1987-02-02 | 1990-01-09 | National Starch And Chemical Corporation | Adhesive compositions for use on vinyl substrates |
US4908268A (en) * | 1988-03-17 | 1990-03-13 | National Starch And Chemical Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
US4911960A (en) * | 1988-01-19 | 1990-03-27 | National Starch And Chemical Corporation | Laminating adhesive for film/paper microwavable products |
US4939220A (en) * | 1988-03-17 | 1990-07-03 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
US4961993A (en) * | 1988-03-17 | 1990-10-09 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
US4963422A (en) * | 1987-10-28 | 1990-10-16 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate alkyl acrylate compositions for flocking adhesives |
EP0795591A3 (en) * | 1996-03-11 | 1997-09-24 | Air Products And Chemicals, Inc. | Vinyl acetate emulsions for high scrub paints |
US20040118534A1 (en) * | 2002-12-19 | 2004-06-24 | Anderson Ralph Lee | Low formaldehyde creping composition and product and process incorporating same |
US20070088120A1 (en) * | 2005-10-19 | 2007-04-19 | Helmut Zecha | Vinyl ester based polymer latex composition and process of making the same |
DE102012202843A1 (de) | 2012-02-24 | 2013-08-29 | Wacker Chemie Ag | Verfahren zur Herstellung von Vinylester-Ethylen-Acrylsäureamid-Mischpolymerisaten |
CN112482046A (zh) * | 2020-11-18 | 2021-03-12 | 浙江理工大学上虞工业技术研究院有限公司 | 一种无甲醛具有耐久光泽的棉织物加工方法 |
CN113956386A (zh) * | 2021-10-18 | 2022-01-21 | 杭州传化精细化工有限公司 | 一种环保增重硬挺树脂及其制备方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA987415A (en) * | 1971-05-11 | 1976-04-13 | Martin K. Lindemann | Thermosetting vinyl ester emulsion copolymers |
JPS51125590U (enrdf_load_stackoverflow) * | 1975-04-02 | 1976-10-12 | ||
US4219454A (en) * | 1978-09-05 | 1980-08-26 | Air Products And Chemicals, Inc. | Vinyl acetate copolymer emulsions for paint |
DE3205904A1 (de) * | 1982-02-19 | 1983-09-01 | Chemische Fabrik Pfersee Gmbh, 8900 Augsburg | Verfahren zur emsulsionscopolymerisation, die nach dem verfahren hergestellten emulsionscopolymerisate und deren verwendung |
CN115449253A (zh) * | 2022-08-31 | 2022-12-09 | 亚士创能科技(石家庄)有限公司 | 亚甲基丁二酸溶液的应用、多彩涂料的增稠方法、多彩涂料及其应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2703794A (en) * | 1951-09-04 | 1955-03-08 | Du Pont | Ethylene/vinyl acetate polymerization process |
US3090704A (en) * | 1961-02-14 | 1963-05-21 | Du Pont | Antistatic and antisoiling agent and process for treating synthetic linear textile therewith |
US3118852A (en) * | 1955-02-24 | 1964-01-21 | Pittsburgh Plate Glass Co | Compositions comprising a carboxylic acid amide interpolymer and a hydroxyl-containing polymer |
US3137589A (en) * | 1958-11-05 | 1964-06-16 | Basf Ag | Production of bonded fiber fleeces |
US3301809A (en) * | 1965-04-23 | 1967-01-31 | Nat Starch Chem Corp | Nu-methylol acrylamide-vinyl acetate copolymer emulsions containing polyvinyl alcohol |
-
1965
- 1965-03-31 US US444375A patent/US3345318A/en not_active Expired - Lifetime
-
1966
- 1966-03-30 DE DE19661619206 patent/DE1619206B2/de not_active Ceased
- 1966-03-31 GB GB14360/66A patent/GB1116909A/en not_active Expired
- 1966-03-31 JP JP41019724A patent/JPS507192B1/ja active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2703794A (en) * | 1951-09-04 | 1955-03-08 | Du Pont | Ethylene/vinyl acetate polymerization process |
US3118852A (en) * | 1955-02-24 | 1964-01-21 | Pittsburgh Plate Glass Co | Compositions comprising a carboxylic acid amide interpolymer and a hydroxyl-containing polymer |
US3137589A (en) * | 1958-11-05 | 1964-06-16 | Basf Ag | Production of bonded fiber fleeces |
US3090704A (en) * | 1961-02-14 | 1963-05-21 | Du Pont | Antistatic and antisoiling agent and process for treating synthetic linear textile therewith |
US3301809A (en) * | 1965-04-23 | 1967-01-31 | Nat Starch Chem Corp | Nu-methylol acrylamide-vinyl acetate copolymer emulsions containing polyvinyl alcohol |
Cited By (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3380851A (en) * | 1965-03-31 | 1968-04-30 | Air Reduction | Nonwoven fabric with vinyl acetateethylene-n-methylol acrylamide interpolymer as binder |
US3459698A (en) * | 1966-01-10 | 1969-08-05 | Gulf Oil Corp | Ethylene - n - methylol acrylamideacrylic ester terpolymers as bonding agents for nonwoven fabrics |
US3714105A (en) * | 1969-11-05 | 1973-01-30 | Borden Inc | Adhesive latexes of vinyl acetate/ethylene/n-methylolacrylamide terpolymers |
US3658570A (en) * | 1969-12-09 | 1972-04-25 | Larry L Crooks | Imparting a satin like finish to one side of a fabric |
US3644241A (en) * | 1970-03-11 | 1972-02-22 | Colgate Palmolive Co | Antisoiling aerosol starch prepared from ethoxylated starch and a fluoroacrylate or fluoroalpha substituted acrylate polymer |
DE2135459A1 (enrdf_load_stackoverflow) * | 1970-07-16 | 1972-01-20 | ||
US3714099A (en) * | 1970-09-03 | 1973-01-30 | Union Oil Co | Self-crosslinking vinyl acetate-ethylene latexes |
US3714100A (en) * | 1970-09-03 | 1973-01-30 | Union Oil Co | Crosslinkable vinyl acetate latices |
US3852233A (en) * | 1971-05-11 | 1974-12-03 | Chase S Tanner Co | Thermosetting vinyl ester-ethylene emulsion copolymers |
JPS4879854A (enrdf_load_stackoverflow) * | 1972-01-18 | 1973-10-26 | ||
DE2202189A1 (de) * | 1972-01-18 | 1973-07-26 | Hoechst Ag | Verfahren zur herstellung von emulgatorfreien polymerisatdispersionen |
US3912674A (en) * | 1973-04-30 | 1975-10-14 | Du Pont | Ethylene copolymer dispersions as water repellent coatings |
US4001160A (en) * | 1973-09-26 | 1977-01-04 | Chas. S. Tanner Co. | Aqueous emulsion adhesives based on C2 -C8 ethers of N-methylol amides copolymerized with vinyl esters in the presence of hydroxy functional protective colloids |
US4001158A (en) * | 1974-01-16 | 1977-01-04 | Chas. S. Tanner Co. | Crushed foam-backed fabrics and emulsions for producing the same |
DE2512589A1 (de) * | 1975-03-21 | 1976-09-30 | Wacker Chemie Gmbh | Thermisch selbstvernetzende copolymere |
DE2551556A1 (de) * | 1975-11-17 | 1977-05-26 | Wacker Chemie Gmbh | Thermisch selbstvernetzende copolymere |
US4075387A (en) * | 1976-06-30 | 1978-02-21 | Celanese Corporation | Non-woven fabric binders |
US4416727A (en) * | 1982-01-11 | 1983-11-22 | Air Products And Chemicals, Inc. | Process for recovering fiber from wet-strength resin coated paper |
US4847143A (en) * | 1985-06-04 | 1989-07-11 | Sumitomo Chemical Company, Limited | Binder composition and nonwoven fabrics and impregnated papers using the same |
US4745025A (en) * | 1986-02-19 | 1988-05-17 | Air Products And Chemicals, Inc. | Nonwoven products bonded with binder emulsions of vinyl acetate/ethylene copolymers having improved solvent resistance |
US4698384A (en) * | 1986-02-19 | 1987-10-06 | Air Products And Chemicals, Inc. | Nonwoven binder emulsions of vinyl acetate/ethylene copolymers having improved solvent resistance |
US4737386A (en) * | 1986-09-08 | 1988-04-12 | National Starch And Chemical Corporation | Textile coating composition and textiles coated therewith |
US4692366A (en) * | 1986-09-08 | 1987-09-08 | National Starch And Chemical Corporation | Flocking adhesives based on eva-maleate copolymers |
US4866119A (en) * | 1986-09-08 | 1989-09-12 | National Starch And Chemical Corporation | Textile coatings based on eva-maleate copolymers |
US4740394A (en) * | 1986-09-08 | 1988-04-26 | National Starch And Chemical Corporation | Textile coatings based on eva-maleate copolymers |
US4892917A (en) * | 1987-02-02 | 1990-01-09 | National Starch And Chemical Corporation | Adhesive compositions for use on vinyl substrates |
US4963422A (en) * | 1987-10-28 | 1990-10-16 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate alkyl acrylate compositions for flocking adhesives |
US4911960A (en) * | 1988-01-19 | 1990-03-27 | National Starch And Chemical Corporation | Laminating adhesive for film/paper microwavable products |
US4908268A (en) * | 1988-03-17 | 1990-03-13 | National Starch And Chemical Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
US4961993A (en) * | 1988-03-17 | 1990-10-09 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
US4939220A (en) * | 1988-03-17 | 1990-07-03 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
EP0795591A3 (en) * | 1996-03-11 | 1997-09-24 | Air Products And Chemicals, Inc. | Vinyl acetate emulsions for high scrub paints |
US20040118534A1 (en) * | 2002-12-19 | 2004-06-24 | Anderson Ralph Lee | Low formaldehyde creping composition and product and process incorporating same |
US20070088120A1 (en) * | 2005-10-19 | 2007-04-19 | Helmut Zecha | Vinyl ester based polymer latex composition and process of making the same |
EP1777241A1 (en) | 2005-10-19 | 2007-04-25 | Air Products Polymers, L.P. | Vinyl ester based polymer latex composition and process of making the same |
US7649067B2 (en) | 2005-10-19 | 2010-01-19 | Wacker Polymers, L.P. | Process of making a vinyl ester based polymer latex composition |
DE102012202843A1 (de) | 2012-02-24 | 2013-08-29 | Wacker Chemie Ag | Verfahren zur Herstellung von Vinylester-Ethylen-Acrylsäureamid-Mischpolymerisaten |
WO2013124417A1 (de) | 2012-02-24 | 2013-08-29 | Wacker Chemie Ag | Verfahren zur herstellung von vinylester-ethylen-acrylsäureamid-mischpolymerisaten |
CN112482046A (zh) * | 2020-11-18 | 2021-03-12 | 浙江理工大学上虞工业技术研究院有限公司 | 一种无甲醛具有耐久光泽的棉织物加工方法 |
CN112482046B (zh) * | 2020-11-18 | 2022-06-03 | 浙江理工大学上虞工业技术研究院有限公司 | 一种无甲醛具有耐久光泽的棉织物加工方法 |
CN113956386A (zh) * | 2021-10-18 | 2022-01-21 | 杭州传化精细化工有限公司 | 一种环保增重硬挺树脂及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JPS507192B1 (enrdf_load_stackoverflow) | 1975-03-22 |
DE1619206A1 (de) | 1970-10-08 |
DE1619206B2 (de) | 1976-03-11 |
GB1116909A (en) | 1968-06-12 |
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