US20200040520A1 - Fibers to which silicone has been fixed, and production method thereof - Google Patents
Fibers to which silicone has been fixed, and production method thereof Download PDFInfo
- Publication number
- US20200040520A1 US20200040520A1 US16/499,083 US201816499083A US2020040520A1 US 20200040520 A1 US20200040520 A1 US 20200040520A1 US 201816499083 A US201816499083 A US 201816499083A US 2020040520 A1 US2020040520 A1 US 2020040520A1
- Authority
- US
- United States
- Prior art keywords
- fibers
- silicone
- modified organopolysiloxane
- acrylic
- amino
- 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.)
- Abandoned
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 202
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 188
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 56
- 238000010894 electron beam technology Methods 0.000 claims abstract description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000011248 coating agent Substances 0.000 claims abstract description 8
- 238000000576 coating method Methods 0.000 claims abstract description 8
- 230000001678 irradiating effect Effects 0.000 claims abstract description 5
- -1 silk Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000000839 emulsion Substances 0.000 claims description 24
- 125000003277 amino group Chemical group 0.000 claims description 21
- 229920000742 Cotton Polymers 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000002612 dispersion medium Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 244000025254 Cannabis sativa Species 0.000 claims description 4
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 4
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 210000000077 angora Anatomy 0.000 claims description 4
- 235000009120 camo Nutrition 0.000 claims description 4
- 235000005607 chanvre indien Nutrition 0.000 claims description 4
- 238000007865 diluting Methods 0.000 claims description 4
- 239000011487 hemp Substances 0.000 claims description 4
- 210000000050 mohair Anatomy 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 3
- 239000004745 nonwoven fabric Substances 0.000 claims description 3
- 239000002759 woven fabric Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 238000005406 washing Methods 0.000 abstract description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 21
- 239000007764 o/w emulsion Substances 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000001133 acceleration Effects 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000008119 colloidal silica Substances 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 229920002972 Acrylic fiber Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical class CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000004876 x-ray fluorescence Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 229920002334 Spandex Polymers 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical class CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- 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
-
- 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
- D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
-
- 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
- D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
- D06M14/22—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
- D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
- D06M14/24—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of animal origin, e.g. wool or silk
-
- 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
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
- D06M15/3568—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing silicon
Definitions
- the present invention relates to fibers to which silicone is fixed and a method for producing the fibers. Specifically, the present invention relates to fibers to which silicone is fixed by electron beam irradiation and a method for producing the fibers.
- organopolysiloxanes such as a dimethylpolysiloxane, an epoxy group containing organopolysiloxane, and an amino group containing organopolysiloxane have been used as a fiber treatment agent for imparting softness, smoothness, etc. to various fibers and fiber products.
- the amino group containing organopolysiloxane provides good softness and is used in a larger amount than any other organopolysiloxane.
- the fiber treatment agent is generally in the form of an emulsion containing water as a dispersion medium. In the most common method for the treatment of fibers, the fibers are coated or impregnated with the emulsion, and then dried by heating.
- the fibers treated with silicone have an excellent texture immediately after the treatment.
- the effective component (silicone) of the treatment agent is washed away from the fibers after washing several times, and thus the texture will be reduced.
- the reason for this may be that the above silicone treatment agent is unable to react with the fibers, and the silicone is not fixed to the fiber surface, but is present on the fiber surface due to a weak adsorption effect of the amino group on the fibers.
- Patent Document 1 proposes a silicone emulsion composition that includes an anionically stabilized hydroxylated diorganopolysiloxane, colloidal silica, and an organotin compound or an organic amine compound and has a pH of 9 to 11.5.
- Patent Document 2 discloses a silicone latex composition that includes a siloxane block copolymer having dimethylsiloxane units and monophenylsiloxane units, water, a cationic surfactant, a filler, and an aminosilane.
- Patent Document 3 proposes a silicone emulsion composition that includes a hydroxyl group containing organopolysiloxane, a Si—H group containing organopolysiloxane, colloidal silica, an amide group and carboxyl group containing silane, an epoxy group containing silane, and a curing catalyst.
- Patent Document 4 proposes a silicone emulsion composition that includes an alkenyl group containing organopolysiloxane, a Si—H group containing organopolysiloxane, colloidal silica, a reaction product of an aminosilane and an acid anhydride, an epoxysilane, and an addition reaction catalyst.
- Patent Document 5 proposes a silicone emulsion composition that includes a hydrogen siloxane in which the molecular terminal is blocked with a hydroxyl group, an emulsifier, water, and a curing catalyst.
- Patent Documents 6 to 8 propose a silicone emulsion composition that includes a colloidal silica-silicone core-shell body, a curing catalyst, an emulsifier, and water.
- Patent Document 9 proposes a silicone emulsion composition that includes a hydroxyl group containing organopolysiloxane, colloidal silica, an amide group and carboxyl group containing silane, an epoxy group containing silane, a curing catalyst, and a photocatalytic oxide.
- Patent Document 10 proposes a silicone emulsion composition that includes a hydroxyl group containing organopolysiloxane, colloidal silica, an amide group and carboxyl group containing silane, and an epoxy group containing silane.
- Patent Document 9 JP 2002-363494 A
- Patent Document 10 JP 2008-231276 A
- organotin compounds are typically used as a curing catalyst.
- organotin compounds is being restricted or regulated in applications, fields, and countries because of its toxicity. Therefore, the replacement of dibutyltin compounds by octyltin compounds, and further the replacement of octyltin compounds by inorganic tin compounds or other metal compounds have been proposed, but no effective catalyst system has been found yet. Thus, it is still required that the effect of the silicone treatment agent can be maintained even after washing without using, e.g., toxic metal catalysts.
- the present invention provides silicone-fixed fibers that include fibers to which silicone is fixed and have a good texture even after washing, and a method for producing the silicone-fixed fibers.
- the present invention relates to silicone-fixed fibers including fibers and silicone fixed to the fibers.
- the silicone includes an acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule.
- a rate of decrease in the amount of Si after the silicone-fixed fibers are washed 10 times is less than 50%.
- the present invention relates to a method for producing silicone-fixed fibers including fibers and silicone fixed to the fibers.
- the method includes the following: coating or impregnating the fibers with a fiber treatment agent containing silicone; and irradiating the fibers coated or impregnated with the fiber treatment agent with an electron beam so that the silicone is fixed to the fibers.
- the silicone includes an acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule.
- the present invention can provide silicone-fixed fibers that include fibers to which silicone is firmly fixed and that have a good texture even after washing.
- the production method of the present invention can provide silicone-fixed fibers that include fibers to which silicone is firmly fixed by electron beam irradiation and that have a good texture even after washing.
- the present inventors conducted many studies to fix silicone to fibers so as to give them a good texture even after washing. Consequently, the present inventors found that when fibers were coated or impregnated with a fiber treatment agent containing an acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule, and then the treated fibers were irradiated with an electron beam, silicone was firmly fixed to the fibers and the fibers could have a soft texture of silicone even after washing. Based on these findings, the present inventors have reached the present invention.
- the term “silicone” means a compound in which the main skeleton is composed of a siloxane bond of silicon and oxygen, and an organic group is attached to the silicon. Since the acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule is used as the silicone, radicals are generated by electron beam irradiation and a crosslinking reaction of the silicones proceeds.
- the acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule is not particularly limited and may be, e.g., an acrylic-modified organopolysiloxane that has two or more acrylic groups per molecule and contains a unit represented by the following general formula (1) in the molecule.
- R 1 represents the same or different substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms
- R 2 represents a hydrogen atom
- m is an integer of 1 to 8
- a and b are positive numbers and satisfy a+b ⁇ 3.
- the substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms is not particularly limited.
- Examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms include the following: alkyl groups such as methyl, ethyl, propyl, and butyl groups; alkenyl groups such as vinyl and allyl groups; aryl groups such as phenyl and tolyl groups; and substituted forms of these groups in which some or all hydrogen atoms bonded to carbon atoms are substituted by halogen atoms or cyano groups, including, e.g., chloromethyl group, trifluoropropyl group, and cyanoethyl group.
- R 1 is more preferably a methyl group.
- the viscosity of the acrylic-modified organopolysiloxane (A) is preferably 50 to 5000 mPa ⁇ s at 25° C. If the viscosity is less than 50 mPa ⁇ s, the acrylic-modified organopolysiloxane (A) is not likely to adhere to the fibers. If the viscosity is more than 5000 mPa ⁇ s, the composition will have a higher viscosity, and thus the treatment of the fibers tends to be difficult.
- the viscosity of the acrylic-modified organopolysiloxane (A) is more preferably 100 to 1000 mPa ⁇ s at 25° C.
- the acrylic-modified organopolysiloxane (A) may be either a single acrylic-modified organopolysiloxane or a mixture of a plurality of acrylic-modified organopolysiloxanes which differ in the degree of polymerization and the amount of functional groups.
- the silicone further includes an amino-modified organopolysiloxane (B) having one or more amino groups per molecule, as represented by the following general formula (2).
- B amino-modified organopolysiloxane
- a plurality of R 3 s represent the same or different substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, a hydroxyl group, an alkoxy group, or an amino group.
- a plurality of R 4 s represent the same or different substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms or an amino group. At least one of R 3 s and R 4 s is an amino group.
- n is a positive number. Examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms may be the same as those described above.
- the amino group represented by R 3 or R 4 is not particularly limited and may be, e.g., an amino group represented by the following general formula (3).
- R 5 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 8 carbon atoms
- R 6 , R 7 , and R 8 each represent a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms, or —CH 2 CH(OH)CH 2 OH
- c is an integer of 0 to 4.
- the divalent hydrocarbon group having 1 to 8 carbon atoms include the following: alkylene groups such as ethylene, trimethylene, tetramethylene, hexamethylene, and isobutylene groups; methylene-phenylene group; and methylene-phenylene-methylene group. Among them, the trimethylene group is preferred.
- Examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms include the following: alkyl groups such as methyl, ethyl, propyl, and butyl groups; alkenyl groups such as vinyl and allyl groups; and substituted forms of these groups in which some of hydrogen atoms bonded to carbon atoms are substituted by halogen atoms.
- the methyl group is particularly preferred in terms of water repellency, smoothness and softness.
- the viscosity of the amino-modified organopolysiloxane (B) is preferably 50 to 5000 mPa ⁇ s at 25° C. If the viscosity is less than 50 mPa ⁇ s, the amino-modified organopolysiloxane (B) is not likely to adhere to the fibers. If the viscosity is more than 5000 mPa ⁇ s, the composition will have a higher viscosity, and thus the treatment of the fibers tends to be difficult.
- the viscosity of the amino-modified organopolysiloxane (B) is more preferably 100 to 1000 mPa ⁇ s at 25° C.
- the blending amount of the acrylic-modified organopolysiloxane (A) is preferably, but not limited to, 10 to 95% by mass, and more preferably 30 to 90% by mass and the blending amount of the amino-modified organopolysiloxane (B) is preferably, but not limited to, 5 to 90% by mass, and more preferably 10 to 70% by mass.
- a rate of decrease in the amount of Si after the fibers to which silicone is fixed (i.e., the silicone-fixed fibers) are washed 10 times is less than 50%, preferably 35% or less, more preferably 15% or less, and further preferably 10% or less. With this configuration, the silicone-fixed fibers can have a good texture even after washing.
- the fibers are coated or impregnated with a fiber treatment agent containing the acrylic-modified organopolysiloxane (A) or a fiber treatment agent containing the acrylic-modified organopolysiloxane (A) and the amino-modified organopolysiloxane (B), and then the treated fibers are irradiated with an electron beam, so that silicone can be fixed to the fibers.
- the amount of Si in the fibers may be measured in the following manner.
- the fibers are not particularly limited and may be either natural fibers or synthetic fibers.
- the natural fibers are not particularly limited and may be, e.g., cotton, silk, hemp, wool, angora, or mohair.
- the synthetic fibers are not particularly limited and may be, e.g., polyester fibers, nylon fibers, acrylic fibers, or spandex. From the viewpoint of improving the fixing properties of the silicone to the fibers, the fibers preferably include one or more natural fibers selected from the group consisting of cotton, silk, hemp, wool, angora, and mohair.
- the form of the fibers is not particularly limited.
- the fibers may be in any form such as staple, filament, tow, yarn, woven fabric, knitted fabric, wadding, nonwoven fabric, paper, sheet, or film.
- the silicone-fixed fibers may be produced, e.g., by coating or impregnating the fibers with a fiber treatment agent containing silicone, and irradiating the fibers coated or impregnated with the fiber treatment agent with an electron beam so that the silicone is fixed to the fibers.
- the silicone includes the acrylic-modified organopolysiloxane (A) or a mixture of the acrylic-modified organopolysiloxane (A) and the amino-modified organopolysiloxane (B).
- the silicone i.e., the acrylic-modified organopolysiloxane (A) or the mixture of the acrylic-modified organopolysiloxane (A) and the amino-modified organopolysiloxane (B) (also referred to simply as a “silicone component” in the following) may be directly used as the fiber treatment agent.
- the silicone (silicone component) may be diluted with an organic solvent to form a solution, and this solution may be used as a fiber treatment agent.
- organic solvent Any organic solvent that can dissolve the silicone may be used.
- the organic solvent include the following; aromatic hydrocarbon solvents such as toluene and xylene; aliphatic hydrocarbon solvents such as hexane, octane, and isoparaffin; ether solvents such as diisopropyl ether and 1,4-dioxane; and a mixed solvent thereof.
- the aromatic hydrocarbon solvents such as toluene and xylene and the aliphatic hydrocarbon solvents such as hexane, octane, and isoparaffin are particularly preferred.
- the dilute concentration of the silicone component is not particularly limited.
- the concentration of the acrylic-modified organopolysiloxane (A) or the total concentration of the acrylic-modified organopolysiloxane (A) and the amino-modified organopolysiloxane (B) may be 1 to 60% by mass, and more preferably 1 to 20% by mass.
- the silicone component may be dispersed in water as a dispersion medium to form an emulsion, and this emulsion may be used as a fiber treatment agent for electron beam fixing.
- the emulsification may use, e.g., a nonionic surfactant, an anionic surfactant, a cationic surfactant, or an amphoteric surfactant.
- the nonionic surfactant is not particularly limited and may be, e.g., polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, sorbitan alkylate, or polyoxyethylene sorbitan alkylate.
- the anionic surfactant is not particularly limited and may be, e.g., alkylbenzene sulfonate or alkyl phosphate.
- the cationic surfactant is not particularly limited and may be, e.g., quaternary ammonium salts or alkylamine salts.
- the amphoteric surfactant is not particularly limited and may be, e.g., alkyl betaine or alkyl imidazoline. These surfactants may be used individually or in combinations of two or more. There is no particular limitation to the surfactants. However, from the viewpoint of ease of emulsification of the silicone, the HLB (hydrophilic-lipophilic balance) of the surfactants is preferably 11 to 18, and more preferably 13 to 16.
- the amount of the surfactant used is preferably 5 to 50 parts by mass, and more preferably 10 to 30 parts by mass with respect to 100 parts by mass of the silicone component, i.e., the acrylic-modified organopolysiloxane (A) or the mixture of the acrylic-modified organopolysiloxane (A) and the amino-modified organopolysiloxane (B). Any suitable amount of water may be used for emulsification.
- water may be used in an amount such that the concentration of the acrylic-modified organopolysiloxane (A) or the total concentration of the acrylic-modified organopolysiloxane (A) and the amino-modified organopolysiloxane (B) is generally 1 to 60% by mass, and preferably 1 to 20% by mass.
- the emulsification may be performed by mixing the acrylic-modified organopolysiloxane (A) or the acrylic-modified organopolysiloxane (A) and the amino-modified organopolysiloxane (B) with the surfactant, and emulsifying the mixture with an emulsifier such as a homomixer, a homogenizer, a colloid mill, or a line mixer.
- an emulsifier such as a homomixer, a homogenizer, a colloid mill, or a line mixer.
- these components when both the acrylic-modified organopolysiloxane (A) and the amino-modified organopolysiloxane (B) are used as the silicone component, these components may be mixed in advance to form a solution or an emulsion. Alternatively, these components may be separately formed in advance into solutions or emulsions, and then the respective solutions or emulsions may be mixed together.
- other agents for fibers such as an anticrease agent, a flame retardant, an antistatic agent, and a heat resistant agent may be added to the fiber treatment agent as long as the properties of the fiber treatment agent are not impaired.
- the fibers are coated or impregnated with the fiber treatment agent containing the silicone.
- the fibers that serve as a base material are not particularly limited and may be the same as those described above.
- any known method such as roll coating, gravure coating, wire doctor coating, air knife coating, or dipping may be used to coat or impregnate the fibers with the fiber treatment agent.
- the coating or impregnation amount is preferably 0.01 to 20.0 g/m 2 , and more preferably 0.01 to 5 g/m 2 . When the coating or impregnation amount is within the above range, the adhesion of the silicone to the fibers can be improved.
- the fibers coated or impregnated with the fiber treatment agent may be dried to vaporize the organic solvent or the water (the dispersion medium of the emulsion).
- the drying may be performed, e.g., by blowing hot air on the fibers or using a heating furnace.
- the drying temperature and the drying time may be determined as desired so as not to affect the fibers.
- the drying temperature may be 100 to 150° C. and the drying time may be 10 sec to 5 min.
- the electron beam irradiation apparatus is not particularly limited and may be, e.g., a curtain system, a scanning system, or a double scanning system.
- the acceleration voltage of the electron beam by the electron beam irradiation is not particularly limited and may be, e.g., 100 to 1000 kV. If the acceleration voltage is less than 100 kV, there may be a lack of energy transmission. If the acceleration voltage is more than 1000 kV, economic efficiency may be reduced.
- the irradiation amount of the electron beam is not particularly limited and may be, e.g., 5 to 100 kGy.
- the fibers may be degraded.
- the fiber treatment agent is a solution obtained by diluting the silicone with an organic solvent
- the fibers may be immersed (washed) in the organic solvent that has been used for dilution of the silicone, after the electron beam irradiation, thereby removing unreacted silicone.
- the fiber treatment agent is an emulsion obtained by dispersing the silicone in water
- the fibers may be washed with water after the electron beam irradiation, thereby removing unreacted silicone.
- the present invention is not limited to the following examples.
- the term “part” indicates “part by mass” and the physical property values indicate measured values by the following test methods.
- the samples were washed 10 times or 50 times in accordance with the JIS L 0217 103 method (detergent: JAFET) and dried. Then, using the X-ray fluorescence analyzer ZSX100e manufactured by Rigaku Corporation, the mass of all elements (W10t or W50t) and the mass of Si atoms (W10s or W50s) contained in the individual samples after 10 times washing or 50 times washing were measured by the EZ-scan method, and the amount of Si after 10 times washing and the amount of Si after 50 times washing were calculated by the following formulas.
- W0s % indicates the initial amount of Si and W10s % indicates the amount of Si after 10 times washing.
- the samples were washed 10 times or 50 times in accordance with the JIS L 0217 103 (detergent: JAFET). Subsequently, three panelists touched the samples by hand to check the softness of the samples after washing and evaluated them based on the following criteria.
- an acrylic-modified organopolysiloxane (A1) represented by the following average molecular formula (4) was diluted with toluene to prepare a fiber treatment agent (a) in which the concentration of the acrylic-modified organopolysiloxane (A1) was 10% by mass.
- a broadcloth made of 100% by mass of cotton manufactured by KURABO was immersed in the fiber treatment agent (a), squeezed by a mangle roller at a squeeze rate of 100%, and dried at 110° C. for 90 seconds.
- the broadcloth was irradiated with an electron beam of 40 kGy at an acceleration voltage of 200 kV in a nitrogen atmosphere using an area beam type electron beam irradiation apparatus EC250/15/180L (manufactured by IWASAKI ELECTRIC CO., LTD.).
- the fibers i.e., the broadcloth made of 100% by mass of cotton
- the fibers were immersed in toluene for 1 minute and then squeezed by a mangle roller at a squeeze rate of 60%. Further, the fibers were again immersed in fresh toluene for 1 minute, squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- silicone-fixed fibers were produced.
- An acrylic-modified organopolysiloxane (A2) represented by the following average molecular formula (5) was diluted with toluene to prepare a fiber treatment agent (b) in which the concentration of the acrylic-modified organopolysiloxane (A2) was 10% by mass.
- a broadcloth made of 100% by mass of cotton manufactured by KURABO was immersed in the fiber treatment agent (b), squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- the broadcloth was irradiated with an electron beam of 40 kGy at an acceleration voltage of 200 kV in a nitrogen atmosphere using an area beam type electron beam irradiation apparatus EC250/30/90L (manufactured by IWASAKI ELECTRIC CO., LTD.).
- the fibers i.e., the broadcloth made of 100% by mass of cotton
- the fibers were immersed in toluene for 1 minute and then squeezed by a mangle roller at a squeeze rate of 60%. Further, the fibers were again immersed in fresh toluene for 1 minute, squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- silicone-fixed fibers were produced.
- a broadcloth made of 100% by mass of cotton (manufactured by KURABO) was immersed in the fiber treatment agent (c), squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds. Then, the broadcloth was irradiated with an electron beam of 40 kGy at an acceleration voltage of 200 kV in a nitrogen atmosphere using an area beam type electron beam irradiation apparatus EC250/30/90L (manufactured by IWASAKI ELECTRIC CO., LTD.).
- the fibers i.e., the broadcloth made of 100% by mass of cotton
- the fibers thus treated with the electron beam were washed with water, squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- silicone-fixed fibers were produced.
- phase-inverted water ion-exchanged water
- oil-in-water emulsion (II) in which the concentration of the amino-modified organopolysiloxane (B1) was 50% by mass was obtained.
- the oil-in-water emulsion (II) was mixed with the oil-in-water emulsion (I) prepared in the same manner as Example 3 at a ratio of the oil-in-water emulsion (I) to the oil-in-water emulsion (II) of 50 parts by mass/50 parts by mass to form an oil-in-water emulsion (III).
- the oil-in-water emulsion (III) was diluted with ion-exchanged water to prepare a fiber treatment agent (d) in which the concentration of the organopolysiloxane (i.e., the total concentration of the acrylic-modified organopolysiloxane (A2) and the amino-modified organopolysiloxane (B1)) was 10% by mass.
- a broadcloth made of 100% by mass of cotton manufactured by KURABO was immersed in the fiber treatment agent (d), squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- the broadcloth was irradiated with an electron beam of 40 kGy at an acceleration voltage of 200 kV in a nitrogen atmosphere using an area beam type electron beam irradiation apparatus EC250/30/90L (manufactured by IWASAKI ELECTRIC CO., LTD.).
- the fibers i.e., the broadcloth made of 100% by mass of cotton
- the fibers thus treated with the electron beam were washed with water, squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- silicone-fixed fibers were produced.
- a dimethylpolysiloxane having no organic group other than a methyl group and having a viscosity of 1000 mm 2 /s was diluted with toluene to prepare a fiber treatment agent (Z) in which the concentration of the dimethylpolysiloxane was 10% by mass.
- a broadcloth made of 100% cotton manufactured by KURABO was immersed in the fiber treatment agent (Z), squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- the broadcloth was irradiated with an electron beam of 40 kGy at an acceleration voltage of 200 kV in a nitrogen atmosphere using an area beam type electron beam irradiation apparatus EC250/30/90L (manufactured by IWASAKI ELECTRIC CO., LTD.).
- the fibers i.e., the broadcloth made of 100% cotton
- the fibers were immersed in a toluene solution for 1 minute and then squeezed by a mangle roller at a squeeze rate of 60%. Further, the fibers were again immersed in a fresh toluene solution for 1 minute, squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- a fiber treatment agent (c) was prepared in the same manner as Example 3.
- a broadcloth made of 100% cotton manufactured by KURABO was immersed in the fiber treatment agent (c), squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- the fibers i.e., the broadcloth made of 100% cotton
- the fibers were washed with water, squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- An oil-in-water emulsion (II) in which the concentration of an amino-modified organopolysiloxane (B1) was 50% by mass was prepared in the same manner as Example 4.
- the oil-in-water emulsion (II) was diluted with ion-exchanged water to prepare a fiber treatment agent (Y) in which the concentration of the amino-modified organopolysiloxane (B1) was 10% by mass.
- a broadcloth made of 100% cotton manufactured by KURABO
- the fibers i.e., the broadcloth made of 100% cotton
- the fiber treatment agent (Y) were washed with water, squeezed by a mangle roller at a squeeze rate of 60%, and dried at 110° C. for 90 seconds.
- the initial amount of Si (the amount of Si before washing), the amount of Si after 10 times washing, the amount of Si after 50 times washing, the initial texture, and the texture after washing of the respective fibers (i.e., the broadcloths made of 100% cotton) obtained in Examples 1 to 4 and Comparative Examples 1 to 3 were measured in the above manner.
- Table 1 shows the results.
- the fibers had been impregnated with the fiber treatment agent, in which the acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule was dissolved in the organic solvent, and then irradiated with the electron beam. Consequently, these fibers had good softness, and the acrylic-modified organopolysiloxane (A) was fixed to the fibers even after washing. Specifically, a considerable amount of the acrylic-modified organopolysiloxane was fixed to the fibers after they were washed 10 times. In particular, in Example 2, a certain amount of the acrylic-modified organopolysiloxane was fixed to the fibers even after they were washed 50 times.
- the fixing properties of the acrylic-modified organopolysiloxane (A) to the fibers were higher in Example 2 than in Example 1, since the acrylic-modified organopolysiloxane (A) used in Example 2 had a large number of acrylic groups as compared to the acrylic-modified organopolysiloxane (A) used in Example 1.
- Example 3 the fibers had been treated with the fiber treatment agent, in which the acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule was emulsified. Consequently, the fibers also had good softness. Comparing Example 3 and Example 4 shows that when the acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule was used in combination with the amino-modified organopolysiloxane (B) having one or more amino groups per molecule, the initial amount of silicone fixed to the fibers was increased, the softness of the fibers was very good, and the organopolysiloxane was sufficiently fixed to the fibers even after they were washed 10 times.
- Comparative Example 1 the fibers had been treated with the dimethylpolysiloxane having no acrylic group. Consequently, the initial amount of dimethylpolysiloxane adhering to the fibers was small, and almost no dimethylpolysiloxane was left after the fibers were washed 10 times or 50 times.
- Comparative Example 2 the fibers had been treated with the fiber treatment agent in which the acrylic-modified organopolysiloxane (A) having two or more acrylic groups per molecule was emulsified, but had not been subjected to electron beam irradiation.
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JP2017-072061 | 2017-03-31 | ||
JP2017-117114 | 2017-06-14 | ||
JP2017117114A JP7008432B2 (ja) | 2017-03-31 | 2017-06-14 | シリコーンが固着された繊維及びその製造方法 |
PCT/JP2018/010486 WO2018180601A1 (ja) | 2017-03-31 | 2018-03-16 | シリコーンが固着された繊維及びその製造方法 |
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US (1) | US20200040520A1 (zh) |
EP (1) | EP3604666A4 (zh) |
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US11214920B2 (en) | 2017-03-31 | 2022-01-04 | Shin-Etsu Chemical Co., Ltd. | Fiber treatment agent for electron beam fixing |
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JP6909671B2 (ja) * | 2017-03-31 | 2021-07-28 | 信越化学工業株式会社 | 電子線固着用繊維処理剤 |
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US4654041A (en) * | 1985-04-26 | 1987-03-31 | Hansa Textilchemie Gmbh | Process for the removal of silicones from fibers, yarns or two-dimensional textile materials |
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JPS52132171A (en) * | 1976-04-30 | 1977-11-05 | Johnson & Johnson | Newly bonded unwoven fabric and its manufacture |
CA1123530A (en) * | 1979-06-21 | 1982-05-11 | John C. Saam | Silicone emulsion which provides an elastomeric product and methods for preparation |
DE3201205A1 (de) * | 1982-01-16 | 1983-07-28 | Bayer Ag, 5090 Leverkusen | Pfropfmodifizierte siloxandispersionen zur ausruestung von textilen materialien |
US4698406A (en) * | 1986-11-04 | 1987-10-06 | Dow Corning Corporation | Curable organopolysiloxane composition |
JPH01168971A (ja) * | 1987-12-23 | 1989-07-04 | Nisshin Kagaku Kogyo Kk | 繊維用弾性加工剤及び風合改良剤 |
JPH02657A (ja) * | 1988-11-28 | 1990-01-05 | Dow Corning Corp | シリコーンエマルジョンの製造方法 |
JP2960304B2 (ja) * | 1993-06-30 | 1999-10-06 | 信越化学工業株式会社 | 繊維用撥水処理剤 |
JP3181791B2 (ja) * | 1994-09-16 | 2001-07-03 | 信越化学工業株式会社 | シリコーン水性エマルジョン組成物 |
JP3410618B2 (ja) * | 1995-11-29 | 2003-05-26 | 信越化学工業株式会社 | シリコーン水性エマルジョン組成物 |
US5827921A (en) * | 1995-11-29 | 1998-10-27 | Shin-Etsu Chemical Co., Ltd. | Silicone-based aqueous emulsion composition |
JP3121758B2 (ja) * | 1996-02-01 | 2001-01-09 | ジーイー東芝シリコーン株式会社 | エアバッグ用皮膜形成エマルジョン型シリコーン組成物及びエアバッグ |
EP1690885A1 (de) * | 2005-02-09 | 2006-08-16 | Ciba Spezialitätenchemie Pfersee GmbH | Acrylatofunktionelle Polysiloxane |
JP5160073B2 (ja) | 2005-11-30 | 2013-03-13 | ライオン株式会社 | 撥水剤組成物および撥水剤物品 |
JP5900253B2 (ja) * | 2011-09-29 | 2016-04-06 | 信越化学工業株式会社 | (メタ)アクリル変性オルガノポリシロキサン、放射線硬化性シリコーン組成物及びシリコーン剥離紙並びにそれらの製造方法 |
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- 2017-06-14 JP JP2017117114A patent/JP7008432B2/ja active Active
-
2018
- 2018-03-16 EP EP18776645.6A patent/EP3604666A4/en active Pending
- 2018-03-16 CN CN201880021919.5A patent/CN110475928B/zh active Active
- 2018-03-16 US US16/499,083 patent/US20200040520A1/en not_active Abandoned
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US4654041A (en) * | 1985-04-26 | 1987-03-31 | Hansa Textilchemie Gmbh | Process for the removal of silicones from fibers, yarns or two-dimensional textile materials |
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Cited By (1)
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US11214920B2 (en) | 2017-03-31 | 2022-01-04 | Shin-Etsu Chemical Co., Ltd. | Fiber treatment agent for electron beam fixing |
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CN110475928B (zh) | 2022-10-28 |
EP3604666A4 (en) | 2021-01-13 |
JP2018172835A (ja) | 2018-11-08 |
EP3604666A1 (en) | 2020-02-05 |
CN110475928A (zh) | 2019-11-19 |
JP7008432B2 (ja) | 2022-01-25 |
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