US3677810A - Silicone-acrylate soil release treatment for organic textiles - Google Patents
Silicone-acrylate soil release treatment for organic textiles Download PDFInfo
- Publication number
- US3677810A US3677810A US85702A US3677810DA US3677810A US 3677810 A US3677810 A US 3677810A US 85702 A US85702 A US 85702A US 3677810D A US3677810D A US 3677810DA US 3677810 A US3677810 A US 3677810A
- Authority
- US
- United States
- Prior art keywords
- fabric
- weight
- acid
- soil release
- water
- 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
- 239000004753 textile Substances 0.000 title abstract description 13
- 239000002689 soil Substances 0.000 title description 26
- 238000011282 treatment Methods 0.000 title description 5
- -1 POLYMETHYLSILOXANE Polymers 0.000 abstract description 48
- 239000000203 mixture Substances 0.000 abstract description 42
- 229920005989 resin Polymers 0.000 abstract description 28
- 239000011347 resin Substances 0.000 abstract description 28
- 229920003180 amino resin Polymers 0.000 abstract description 19
- 229920002845 Poly(methacrylic acid) Polymers 0.000 abstract description 18
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract description 18
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 9
- 238000004900 laundering Methods 0.000 abstract description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 abstract description 2
- AVKLPTSKTBCMGS-UHFFFAOYSA-N but-2-ene-1,2,3,4-tetrol urea Chemical compound NC(=O)N.C(O)C(=C(O)CO)O AVKLPTSKTBCMGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004744 fabric Substances 0.000 description 67
- 239000000839 emulsion Substances 0.000 description 36
- 239000007787 solid Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 229920001296 polysiloxane Polymers 0.000 description 20
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 229920000742 Cotton Polymers 0.000 description 13
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 9
- 239000012975 dibutyltin dilaurate Substances 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 8
- 239000010705 motor oil Substances 0.000 description 8
- 241000219146 Gossypium Species 0.000 description 7
- 229920004890 Triton X-100 Polymers 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 239000013504 Triton X-100 Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 235000012045 salad Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical compound O=C1NNC(=O)NN1 XMKLTEGSALONPH-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
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 240000007620 Silaum silaus Species 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- YYURIKSQJAECLD-UHFFFAOYSA-N carbamic acid;formaldehyde Chemical compound O=C.NC(O)=O YYURIKSQJAECLD-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- PPBYBJMAAYETEG-UHFFFAOYSA-N ethene;formaldehyde;urea Chemical compound C=C.O=C.NC(N)=O PPBYBJMAAYETEG-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- KNMWLFKLSYMSBR-UHFFFAOYSA-N iron;octanoic acid Chemical compound [Fe].CCCCCCCC(O)=O KNMWLFKLSYMSBR-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LIXVMPBOGDCSRM-UHFFFAOYSA-N nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1 LIXVMPBOGDCSRM-UHFFFAOYSA-N 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 210000002268 wool Anatomy 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
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
- D06M15/673—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain containing phosphorus and nitrogen in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
-
- 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
-
- 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
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- 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
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
-
- 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
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- C—CHEMISTRY; METALLURGY
- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic 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
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
Definitions
- soil release refers to the phenomenon. This is to be distinguished from dry soiling or dry soil release which is particularly apropos to carpeting and drapes. In the latter, one is primarily concerned with soil build-up while the fabric is in use.
- Applicants have found, however, quite unexpectedly that a combination of the organosiloxanes defined hereinafter and polymeric carboxylic acids as defined hereinafter, produce soil release properties equivalent to or superior to those of the polymeric carboxylic acids alone. It has also been found that the combination of silicones and the polymeric carboxylic acids give far superior hand, particularly in connection with crease resistance resins than do the polymer carboxylic acids alone. The presence of the silicone also greatly enhances the mechanical strength of the fabric which is often badly deteriorated by the use of aminoplast crease resistant resins. For example, the combination of the silicone and polymeric acid when applied in conjunction with the aminoplast resin improves the tear of the fabric by 40% or more and the flex abrasion by from 400 to 500% over the same fabric treated with the aminoplast resin alone.
- This invention relates to a mixture of (A) an aminoplast textile resin and in amount sufiicient to increase soil release of an organic fabric to which the mixture is applied, (B) a combination of (1) from 10 to 99% by weight of a polymethylsiloxane containing at least one methyl group per silicon, the remaining substituents on the silicon being substantially all hydrogen or aliphatic hydrocarbon radicals of 1 to 2 carbon atoms and (2) from 1% to by weight of a polymeric, unsaturated, water-soluble carboxylic acid, the proportions of (l) and (2) being based on the combined weights of the two.
- This invention also relates to the method of improving soil release of an organic fabric which comprises applying thereto the mixture of (1) and 2) of the preceding paragraph and thereafter drying the coating on the fabric.
- drying includes curing the coating and merely removing the water or solvent under conditions where no curing occurs.
- silicones which are operative herein are dimethylpolysiloxanes, methyl hydrogen polysiloxanes, methylvinylsiloxane and methylethylsiloxane or copolymers of these.
- the siloxaue is a dimethylsiloxane, a methyl hydrogen siloxane or a dimethylsiloxane containing copolymerized therewith a minor amount i.e., 20 mol percent or less of methylvinylsiloxane or methylethylsiloxane.
- the siloxanes can be endblocked with hydroxyl groups or functional groups such as alkoxy, acetoxy, etc., or they can be endblocked with R SiO units in which R is any hydrocarbon or halohydrocarbon radical.
- the viscosity of the siloxane is not critical and it can range, for example, from 100 cs. to non-flowing gums.
- the polysiloxane can be cured on the fabric or not depending upon the ultimate use of the fabric. If the siloxane is to be cured one can use any of the conventional crosslinkers and catalysts commonly used to cure polysiloxanes. For example, one can cure hydroxyl endblocked polysiloxanes with crosslinkers such as SiH containing siloxanes, alkoxysilanes or alkoxy silicates, acyloxysilanes, ketoxime silanes (i.e.
- RSi(ON CR' where R and R are hydrocarbon radicals) and amineoxy silaues using catalysts such as metal salts of carboxylic acids such as dibutyl-tin-diacetate or ferric octoate or alkyl titanates such as tetrabutyl titanate or amines.
- catalysts such as metal salts of carboxylic acids such as dibutyl-tin-diacetate or ferric octoate or alkyl titanates such as tetrabutyl titanate or amines.
- the cure of the siloxane is not to be confused with the cure of the aminoplast resin although the two can be cured simultaneously, if desired.
- the siloxane and polymeric acid are applied to the fabric without a curing catalyst for the siloxane and the coating is heated to remove any solvent or water.
- the polymeric carboxylic acids used herein are polymers of unsaturated water-soluble carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, vinylacetic acid or fumaric acid.
- the polymeric carboxylic acid can be a homopolymer or it can be copolymer of two or more types of such acids.
- vinylacetic or fumaric acid it is preferable to prepare a copolymer with either acrylic, methacrylic or itaconic acids.
- the polymeric carboxylic acid of this invention can also contain small amounts of other vinylic polymers such as acrylic esters, styrene, vinylchloride, or the like.
- the silicone and the polymeric carboxylic acid can be a copolymer or a mixture.
- the polysiloxane can be prepared and then copolymerized with the unsaturated acid by means of standard emulsion polymerization techniques or by means of standard solvent polymerization techniques. In such techniques the preferred catalyst is potassium persulfate.
- the siloxane contain alkenyl groups if it is desired to prepare copolymers.
- the present invention operates perfectly well with mere blends of the polymeric carboxylic acid and the siloxane. In these circumstances the polysiloxane is prepared separately from the polymeric carboxylic acid, each being polymerized by conventional techniques.
- the two polymers are then blended in any convenient fashion. It has been found that this can be done satisfactorily by mixing the two polymers and then passing the mixture through a colloid mill.
- the siloxane will be in the form of a emuls1on.
- the soil release treatment of this invention can be used in conjunction with aminoplast textile resins.
- aminoplast textile resins These materials are well known articles of commerce. Examples of such resins are urea formaldehyde resins, melamine formaldehyde resins, ethylene urea formaldehyde resins, carbamate formaldehyde resins, amide formaldehyde resins, diurea formaldehyde resins and triazone formaldehyde resins.
- the aminoplast resin can be cured on the textile by any of the conventional catalysts generally employed in commerce. These can be of the Lewis acid type, of the basic type or any other type desired. For a complete list of such catalysts columns 6 and 7 of the aforesaid patent are hereby incorporated by reference.
- the aminoplast resin can be cured by other means such as by radiation.
- the combination of this invention is applied to the fabric by any conventional means such as by padding, dipping or spraying.
- concentration of the treating bath is not critical and can range from 0.1 to 5% or more of the combined weight of the siloxane and polymeric carboxylic acid.
- the aminoplast resin can be applied to the normal concentration used with the particular type fabric empolyed. When aminoplast resins are used the bath can con- .4 tain conventional amounts of such resins such as from 2 to 30% or more shown in US. Pat. 3,377,249.
- the amount of the combination of 1) and (2) on the dry fabric is not critical, nor is the relative amounts of the combination (1) and (2) and the aminoplast resin so long as the aforesaid combination is present in amount suflicient to impart soil release.
- the wet pick up based on the dry weight of the fabric will run from 50 to of the weight of (1) and (2).
- (l), (2) and the aminoplast resin can be applied to the fabric in combination or each ingredient can be applied alone and in any order. Preferably the materials are applied simultaneously.
- the soil release properties of this invention are obtained with any organic fabric such as cellulosic fabrics such as cotton, rayon, cellulose acetate or viscose; polyamide fibers such as nylon; polyacrylic fabrics such as polyacrylonitrile and polyester fibers such as those arrived from ethylene glycol and terephthalic acid; protein fibers such as wool and polyvinylic fibers such as those from copolymers of vinyl chloride and vinylidene chloride or polypropylene. It should be understood that blends of any of these types of fibers can be employed, if desired.
- Triton X-l00 is nonyl benzene poly-alkyleneoxide.
- Permafresh-183 is dihydroxy dimethylol ethylene urea.
- Emulphogen BC-720 is tridecyloxypoly(ethylenoxy) ethanol.
- Abex 188 is an anionic surfactant.
- EXAMPLE 1 An emulsion was prepared by polymerizing methacrylic acid with potassium persulfate in an emulsion of a copolymer of 98.5 mol percent dimethylsiloxane and 1.5 mol percent methylvinylsilox-ane in proportions such that the emulsion contain a weight ratio of 50% polysiloxane and 50% polyacrylic acid.
- the resulting emulsion had a solids content of 13.7%. 26.7 g. of this emulsion was mixed with 44.7 g. of water, .3 g. of Triton X-100, 25 g. of a 45% solids water solution of Permafresh183 and 3.5 g. of a 50% water solution of magnesium chloride.
- the resulting combination was applied to nylon fabric and cured at 250 F. for 15 minutes. After one wash in accordance with the aforesaid standard test the rating from a Sears chassis grease stain was 5, and from burnt motor oil stand was 5. This indicates excellent removal of the stain in one wash.
- EXAMPLE 2 60 g. of methyl hydrogen polysiloxane was mixed with 136 g. of water and emulsified with 4 g. of Emulphogen 130-720. This gave a 30% solids emulsion. 25 g. of this 1 Except In Example 3.
- emulsion was mixed with 98.8 g. of polymethacrylic acid water solution containing 7.5 g. of acid.
- EXAMPLE 3 An emulsion of a copolymer of 98.5 dimethylsiloxane and 1.5 mol percent of methylvinylsiloxane having a concentration of 32% by weight siloxane was prepared. 56.6 g. of this emulsion was mixed with 312 g. of a 7.8% polymethacrylic acid solution. The mixture was put through a colloid mill at a setting of 20 mils followed by 3 passes at a 5 mil setting.
- This mixture was applied to a white cloth composed of 5050 polyester-cotton blend and cured at 250 F. for 15 minutes.
- the fabric was washed and stained in accordance with the aforementioned standard test. However, the stain removal was measured using a photovolt photoelectric cell measuring device which recorded the intensity of light reflected from the sample.
- the cloth treated with the above mixture was checked against the same untreated unstained cloth, the same untreated stained cloth and the same cloth which was treated with the Permafresh-183 resin only and stained. Each sample was checked after one wash and after 23 washes.
- 30.5 g. of the above emulsion was mixed with 45.7 g. of water, .3 g. of Triton X-100, 20 g. of a 45% water solution of Permafresh-183 and 3.5 g. of zinc nitrate solution.
- the bath contained 4% of the combination of silicone and polymethacrylic acid.
- the bath was applied to 5050 blend of polyester and cotton and cured 5 minutes at 250 F. and then 15 minutes at 250 F.
- the fabric was stained with burnt motor oil and upon washing had much better stain removal than an identical fabric treated with a commercial acrylate soil release agent.
- EXAMPLE 5 A 31% solids emulsion was made of a 5500 cs. copolymer of 80 mol percent dimethylsiloxane and 20 mol percent methylvinylsiloxane. 79 g. of this emulsion was mixed with 4 g. of Abex 18S and 300 g. of water and heated to 70 C. under nitrogen. 10.5 g. of a 2% potassium persulfate solution was then added, followed by 25 g. of acrylic acid over a 30 minute period. 10.5 additional grams of 2% potassium persulfate were then added and the mixture heated for 30 minutes at 70 C. and then 30' minutes at C.
- EXAMPLE 6 This example shows use without aminoplast resin.
- An emulsion was made of a copolymer of 98.5 mol percent dirnethylsiloxane and 1.5 mol percent methylvinylsiloxane using dodecyl benzene sulfonic acid. The solids content was 32.2% by weight. 23.9 g. of this emulsion was blended with 100 g. of 7.7% solution of a polymethacrylic acid.
- the test with burnt motor oil showed a soil release of 2 after one wash.
- the untreated fabric had a rating of 1 after one wash.
- EXAMPLE 7 This example shows use of 80% dimethylpolysiloxane and 20% by weight methacrylic acid.
- a 5050 blend of polyester-cotton fabric was immersed in the composition and put through squeeze rolls at 40 p.s.i. pressure. The fabric was treated 15 minutes at 25 0 F. The soil rating for burnt motor oil was 2 after one wash while the fabric with the Permafresh-183 alone was 1.
- EXAMPLE 8 This example shows curing the siloxane. 3 g. of a 35% solids emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane was mixed with 0.3 g. of methyltrimethoxy silane, 0.3 g. of a 20% solids emulsion of dibutyl-tin-dilaurate, 26.3 g. of a 7.3% solids solution of polymethacrylic acid, and 69.2 g. of water.
- This mixture was applied to a 50 50 polyester-cotton fabric and cured 20 minutes at 250 F.
- the fabric was tested and was found after one Wash to have a stain rating of 2 against burnt motor oil and 3 against salad oil.
- the untreated fabric gave a rating of 1 for each stain.
- EXAMPLE 9 This example also shows curing the siloxane. It further shows that at lower concentrations the polymeric acid improves cleanability with good hand characteristics being obtainable.
- compositions (A-H) were prepared and applied to a. white 50-50 polyester-cotton fabric.
- the fabric samples were dipped into the compositions, nipped between rollers with 40 p.s.i. of pressure, dried, and then oven cured for 15 minutes at 250 F. The fabric samples were then tested for soil release.
- the compositions employed are set forth below. Compositions A-C and a fabric sample without any composition were included for purposes of comparison.
- Composition A consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyl-tin-dilaurate, 0.1 g. of acetic acid and 95.6 g. of water.
- Composition B consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 1.3 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 94.4 g. of water.
- Composition C consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, l g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 6.5 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 89.2 g. of water.
- Composition D consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 13 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 82.7 g. of water.
- Composition E consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, l g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 26 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 69.7% water.
- Composition F consisted essentially of 3 g. of a 35 solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 39 g. of a 7.7 solids aqueous solution of polymethacrylic acid, and 56.7% water.
- Composition 6 consisted essentially of 3 g. of a 35 solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 65 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 31.7 g. of water.
- Composition H consisted essentially of 3 g. of a 35 solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrirnethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 94.8 g. of a 7.7 solids aqueous solution of polymethacrylic acid, and 0.9 g. of water.
- the method of improving soil release of an organic fabric which comprises applying thereto a soil release effective amount of a combination of (1) from 10 to 99% by weight of a polymethylsiloxane containing at least one methyl group per silicon, the remaining substituents on the silicon being substantially all hydrogen or aliphatic hydrocarbon radicals of 1 to 2 carbon atoms and (2) from 1 to by Weight of a polymeric, unsaturated, Water-soluble carboxylic acid, the proportions of (1) and (2) being based on the combined Weights of (l) and (2) and thereafter drying the coating on the fabric.
Landscapes
- 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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6946770A | 1970-09-03 | 1970-09-03 | |
US8570270A | 1970-10-30 | 1970-10-30 | |
US23100272A | 1972-03-01 | 1972-03-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3677810A true US3677810A (en) | 1972-07-18 |
Family
ID=27371546
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US85702A Expired - Lifetime US3677810A (en) | 1970-09-03 | 1970-10-30 | Silicone-acrylate soil release treatment for organic textiles |
US00231002A Expired - Lifetime US3714287A (en) | 1970-09-03 | 1972-03-01 | Silicone-acrylate soil release treatment for organic textiles |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00231002A Expired - Lifetime US3714287A (en) | 1970-09-03 | 1972-03-01 | Silicone-acrylate soil release treatment for organic textiles |
Country Status (7)
Country | Link |
---|---|
US (2) | US3677810A (enrdf_load_stackoverflow) |
AT (1) | AT353740B (enrdf_load_stackoverflow) |
BE (1) | BE772087A (enrdf_load_stackoverflow) |
CA (1) | CA953857A (enrdf_load_stackoverflow) |
CH (3) | CH559278A5 (enrdf_load_stackoverflow) |
DE (1) | DE2144337C3 (enrdf_load_stackoverflow) |
GB (1) | GB1367666A (enrdf_load_stackoverflow) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3770489A (en) * | 1971-09-16 | 1973-11-06 | United Merchants & Mfg | Creaseproofing cellulose-based fabrics |
US3787231A (en) * | 1970-10-15 | 1974-01-22 | Rhone Poulenc Sa | Dentures having a dialkylpolysiloxane coating |
US3871909A (en) * | 1972-06-22 | 1975-03-18 | Warnaco Inc | Hosiery finishing process for treating fabrics containing spandex yarn |
US3947366A (en) * | 1973-07-27 | 1976-03-30 | Andrianov Kuzma A | Size for textile yarns and method of sizing thereof |
US4001154A (en) * | 1973-09-04 | 1977-01-04 | The Dow Chemical Company | Primer adhesive composition |
US4291135A (en) * | 1978-06-23 | 1981-09-22 | Bayer Aktiengesellschaft | Binders for coating compositions |
US4421796A (en) * | 1981-10-03 | 1983-12-20 | Dow Corning Limited | Treating textile fibres |
US4477514A (en) * | 1983-11-14 | 1984-10-16 | Dow Corning Corporation | Method for treating cellulosic textile fabrics with aqueous emulsions of carboxyfunctional silicone fluids |
WO2002002862A3 (en) * | 2000-06-30 | 2002-05-23 | 3M Innovative Properties Co | Treatment of fibrous substrates with silsesquioxanes and stainblockers |
US20040234868A1 (en) * | 2003-05-20 | 2004-11-25 | Cheng-Ming Lin | Novel modification of mask blank to avoid charging effect |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3844825A (en) * | 1972-11-30 | 1974-10-29 | American Cyanamid Co | Method of producing an acrylic fiber having an improved touch like animal hair |
DE2608894A1 (de) | 1976-03-04 | 1977-09-08 | Pfersee Chem Fab | Verfahren zur herstellung von modifizierten polymerisaten und deren verwendung |
US4320172A (en) * | 1979-07-09 | 1982-03-16 | Shin-Etsu Chemical Co., Ltd. | Organopolysiloxane resin compositions for release papers |
US4425372A (en) | 1981-10-09 | 1984-01-10 | Burlington Industries, Inc. | Process for making absorbent bioactive wettable medical fabric |
US4448810A (en) * | 1982-10-15 | 1984-05-15 | Dow Corning Limited | Treating textile fibres with quaternary salt polydiorganosiloxane |
JPS63146976A (ja) * | 1986-12-11 | 1988-06-18 | Daikin Ind Ltd | 撥水撥油剤組成物 |
DE69806056T2 (de) | 1997-12-18 | 2003-01-23 | Tremco Inc., Beachwood | Polysiloxan mit dispergiertem copolymeren und dieses enthaltende dichtungsmassen |
US6616980B2 (en) | 2001-04-24 | 2003-09-09 | Crompton Corporation | Emulsion polymerized acrylated silicone copolymer for wrinkle reduction |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3236685A (en) * | 1962-06-20 | 1966-02-22 | Eastman Kodak Co | Process for treating textile fibers and other shaped products with coatings |
-
1970
- 1970-10-30 US US85702A patent/US3677810A/en not_active Expired - Lifetime
-
1971
- 1971-06-01 CA CA114,483A patent/CA953857A/en not_active Expired
- 1971-08-19 GB GB3895571A patent/GB1367666A/en not_active Expired
- 1971-09-01 CH CH593674A patent/CH559278A5/xx not_active IP Right Cessation
- 1971-09-01 CH CH1284371D patent/CH1284371A4/xx unknown
- 1971-09-01 CH CH1284371A patent/CH568437B5/xx not_active IP Right Cessation
- 1971-09-02 BE BE772087A patent/BE772087A/xx not_active IP Right Cessation
- 1971-09-03 DE DE2144337A patent/DE2144337C3/de not_active Expired
- 1971-09-03 AT AT771371A patent/AT353740B/de not_active IP Right Cessation
-
1972
- 1972-03-01 US US00231002A patent/US3714287A/en not_active Expired - Lifetime
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3787231A (en) * | 1970-10-15 | 1974-01-22 | Rhone Poulenc Sa | Dentures having a dialkylpolysiloxane coating |
US3770489A (en) * | 1971-09-16 | 1973-11-06 | United Merchants & Mfg | Creaseproofing cellulose-based fabrics |
US3871909A (en) * | 1972-06-22 | 1975-03-18 | Warnaco Inc | Hosiery finishing process for treating fabrics containing spandex yarn |
US3947366A (en) * | 1973-07-27 | 1976-03-30 | Andrianov Kuzma A | Size for textile yarns and method of sizing thereof |
US4001154A (en) * | 1973-09-04 | 1977-01-04 | The Dow Chemical Company | Primer adhesive composition |
US4291135A (en) * | 1978-06-23 | 1981-09-22 | Bayer Aktiengesellschaft | Binders for coating compositions |
US4421796A (en) * | 1981-10-03 | 1983-12-20 | Dow Corning Limited | Treating textile fibres |
US4477514A (en) * | 1983-11-14 | 1984-10-16 | Dow Corning Corporation | Method for treating cellulosic textile fabrics with aqueous emulsions of carboxyfunctional silicone fluids |
WO2002002862A3 (en) * | 2000-06-30 | 2002-05-23 | 3M Innovative Properties Co | Treatment of fibrous substrates with silsesquioxanes and stainblockers |
US20040234868A1 (en) * | 2003-05-20 | 2004-11-25 | Cheng-Ming Lin | Novel modification of mask blank to avoid charging effect |
Also Published As
Publication number | Publication date |
---|---|
BE772087A (fr) | 1972-03-02 |
CH559278A5 (enrdf_load_stackoverflow) | 1975-02-28 |
DE2144337A1 (de) | 1972-03-09 |
GB1367666A (en) | 1974-09-18 |
DE2144337B2 (de) | 1974-06-27 |
DE2144337C3 (de) | 1975-02-20 |
AT353740B (de) | 1979-11-26 |
CH1284371A4 (enrdf_load_stackoverflow) | 1975-05-30 |
US3714287A (en) | 1973-01-30 |
ATA771371A (de) | 1979-05-15 |
CA953857A (en) | 1974-09-03 |
CH568437B5 (enrdf_load_stackoverflow) | 1975-10-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3677810A (en) | Silicone-acrylate soil release treatment for organic textiles | |
US4098701A (en) | Process for treating fibres | |
US2807601A (en) | Compositions for treating organic fabrics and a method of applying them | |
CA1188462A (en) | Fiber-treating compositions comprising two organo- functional polysiloxanes | |
US4311626A (en) | Silicone compositions for the treatment of fibers | |
CA1167585A (en) | Organo-functional polysiloxane compositions for fiber- treating | |
EP0186492B1 (en) | Method for treating materials with organopolysiloxane compounds | |
JPS6129623B2 (enrdf_load_stackoverflow) | ||
US5300239A (en) | Water-repellent and oil-repellent treatment | |
CA2066897C (en) | Fiber treatment agent | |
JPS5926707B2 (ja) | 繊維質物用処理剤 | |
US2927870A (en) | Zirconium acetate-zinc acetate catalyzed organohydrogenosiloxane emulsions and the treatment of fabrics therewith | |
US2612482A (en) | Water-repellent compositions | |
CA2049810A1 (en) | Water-repellent and oil-repellent treatment agent | |
US6756077B2 (en) | Water repellent textile finishes and method of making | |
US4152273A (en) | Soil releasable hydrophilic surface finish for textile fabrics | |
JP5356684B2 (ja) | 疎油性および/または疎水性を繊維材料に付与するシリコーン/フッ素化有機化合物の混合組成物 | |
US3445276A (en) | Textile materials coated with hydrolytically stable siloxane-oxyalkylene block copolymers containing sih | |
US2728692A (en) | Method of preventing shrinkage of wool | |
US3592686A (en) | Process for making durable press and soil release textile and resultant article | |
US3179534A (en) | Coated oleophobic fabrics | |
GB2075040A (en) | Organopolysiloxane Compositions | |
US3032442A (en) | Process of finishing textiles with silicone-colloidal melamine resin mixtures, composition and resultant article | |
US3379564A (en) | Method of coating a synthetic polymeric material by cross-linking a polysiloxane containing 2-cyanoethyl and 2-carboxyethyl groups | |
KR840001404B1 (ko) | 섬유처리용 실리콘 조성물 |