TWI708813B - 包括含異氰酸酯衍生烯系不飽和單體之寡聚物的無氟纖維處理組成物、及處理方法 - Google Patents
包括含異氰酸酯衍生烯系不飽和單體之寡聚物的無氟纖維處理組成物、及處理方法 Download PDFInfo
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- TWI708813B TWI708813B TW105104348A TW105104348A TWI708813B TW I708813 B TWI708813 B TW I708813B TW 105104348 A TW105104348 A TW 105104348A TW 105104348 A TW105104348 A TW 105104348A TW I708813 B TWI708813 B TW I708813B
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- Prior art keywords
- isocyanate
- carbon atoms
- group
- independently
- fluorine
- Prior art date
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 186
- 239000000203 mixture Substances 0.000 title claims abstract description 183
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 173
- 239000000178 monomer Substances 0.000 title claims abstract description 107
- 238000000034 method Methods 0.000 title claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 160
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 238000006243 chemical reaction Methods 0.000 claims abstract description 103
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 97
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 87
- 239000011541 reaction mixture Substances 0.000 claims abstract description 55
- 239000002981 blocking agent Substances 0.000 claims abstract description 40
- 239000000758 substrate Substances 0.000 claims abstract description 39
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 14
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 14
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 carbon atoms Ester Chemical class 0.000 claims description 59
- 239000003999 initiator Substances 0.000 claims description 37
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 37
- 150000003254 radicals Chemical class 0.000 claims description 37
- 150000003573 thiols Chemical group 0.000 claims description 37
- 238000002360 preparation method Methods 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000006185 dispersion Substances 0.000 claims description 16
- 238000006384 oligomerization reaction Methods 0.000 claims description 15
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- 239000004094 surface-active agent Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
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- 230000000977 initiatory effect Effects 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- 230000002528 anti-freeze Effects 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 144
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 88
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 72
- 239000000463 material Substances 0.000 description 54
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
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- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 20
- 239000007921 spray Substances 0.000 description 20
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 19
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 19
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- 230000000052 comparative effect Effects 0.000 description 15
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 14
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- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 150000002009 diols Chemical class 0.000 description 13
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- 239000003054 catalyst Substances 0.000 description 12
- QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
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- 125000000732 arylene group Chemical group 0.000 description 8
- 238000006482 condensation reaction Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000001568 sexual effect Effects 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
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- 238000003786 synthesis reaction Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000003708 ampul Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 5
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- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 5
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- PLFJWWUZKJKIPZ-UHFFFAOYSA-N 2-[2-[2-(2,6,8-trimethylnonan-4-yloxy)ethoxy]ethoxy]ethanol Chemical compound CC(C)CC(C)CC(CC(C)C)OCCOCCOCCO PLFJWWUZKJKIPZ-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- 229920001410 Microfiber Polymers 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 3
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- 239000008346 aqueous phase Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
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- VPASWAQPISSKJP-UHFFFAOYSA-N ethyl prop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C=C VPASWAQPISSKJP-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 2
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
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- 239000013500 performance material Substances 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
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- 150000003673 urethanes Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
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Classifications
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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- 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
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- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/775—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur sulfur
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
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- 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
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- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/8077—Oximes
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- 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
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- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
- C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/395—Isocyanates
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties
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- Polyurethanes Or Polyureas (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| CN109563339B (zh) | 2016-08-12 | 2022-03-01 | 3M创新有限公司 | 无氟纤维处理组合物、经处理基底以及处理方法 |
| CN109715692B (zh) | 2016-09-19 | 2021-09-07 | 美国陶氏有机硅公司 | 皮肤接触粘合剂及其制备和使用方法 |
| EP3515961A1 (en) | 2016-09-19 | 2019-07-31 | Dow Silicones Corporation | Polyurethane-polyorganosiloxane copolymer and method for its preparation |
| US20210177726A1 (en) | 2017-02-15 | 2021-06-17 | Dow Silicones Corporation | Personal care compositions including a polyurethane - polyorganosiloxane copolymer |
| KR101962816B1 (ko) * | 2017-06-14 | 2019-03-27 | (주)대동켐텍 | 폴리아크릴계 표면 발수제 및 그를 이용한 발수성 섬유제품 |
| CN107700214B (zh) * | 2017-10-24 | 2019-12-24 | 广东德美精细化工集团股份有限公司 | 包含遥爪聚合物的高效无氟防水剂及制备方法 |
| EP3717691A1 (en) * | 2017-11-30 | 2020-10-07 | 3M Innovative Properties Company | Compositions, treating methods, and treated fibrous substrates |
| US11015012B2 (en) | 2017-12-27 | 2021-05-25 | 3M Innovative Properties Company | Hydrophobic polyurethane resins |
| KR102684589B1 (ko) | 2018-12-13 | 2024-07-15 | 헨켈 아이피 앤드 홀딩 게엠베하 | (메트)아크릴레이트-관능화된 왁스 및 그로 제조된 경화성 조성물 |
| FR3095207B1 (fr) * | 2019-04-16 | 2021-04-23 | Commissariat Energie Atomique | Procédé de fonctionnalisation de surface en milieu fluide supercritique |
| US20220325016A1 (en) * | 2019-08-02 | 2022-10-13 | 3M Innovative Properties Company | Acrylate oligomers, acrylate oligomer emulsions, and fluorine-free stain-release compositions containing the same |
| US20210106080A1 (en) * | 2019-10-04 | 2021-04-15 | Under Armour, Inc. | Light weight rain apparel |
| JP7447484B2 (ja) * | 2019-12-26 | 2024-03-12 | ａｒｔｉｅｎｃｅ株式会社 | 樹脂組成物及び積層体 |
| WO2022167974A1 (en) * | 2021-02-03 | 2022-08-11 | 3M Innovative Properties Company | Acrylate oligomers, acrylate oligomer emulsions, and fluorine-free stain-release compositions containing the same |
| CN114933681B (zh) * | 2022-05-16 | 2023-11-21 | 杭州美高华颐化工有限公司 | 一种异氰酸酯改性聚丙烯酸酯无氟防水剂及其制备方法 |
| WO2025083484A1 (en) | 2023-10-19 | 2025-04-24 | 3M Innovative Properties Company | Gas diffusion layer and microporous layer including non-fluorinated hydrophobic material |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010132844A (ja) * | 2008-12-08 | 2010-06-17 | Asahi Glass Co Ltd | ウレタン／尿素化合物、その製造方法および撥水剤組成物 |
| US8440779B2 (en) * | 2004-11-04 | 2013-05-14 | 3M Innovative Properties Company | Carbodiimide compound and compositions for rendering substrates oil and water repellent |
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- 2016-02-09 CN CN201680009108.4A patent/CN107223144B/zh active Active
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- 2016-02-15 TW TW105104348A patent/TWI708813B/zh active
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| JP2010132844A (ja) * | 2008-12-08 | 2010-06-17 | Asahi Glass Co Ltd | ウレタン／尿素化合物、その製造方法および撥水剤組成物 |
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| US10294609B2 (en) | 2019-05-21 |
| CN107223144B (zh) | 2021-02-02 |
| US20180023245A1 (en) | 2018-01-25 |
| BR112017017170B1 (pt) | 2022-05-10 |
| KR102451753B1 (ko) | 2022-10-05 |
| EP3256536B1 (en) | 2021-03-24 |
| EP3256536A1 (en) | 2017-12-20 |
| KR20170118122A (ko) | 2017-10-24 |
| JP6741676B2 (ja) | 2020-08-19 |
| BR112017017170A2 (pt) | 2018-04-03 |
| WO2016130503A1 (en) | 2016-08-18 |
| CN107223144A (zh) | 2017-09-29 |
| TW201700606A (zh) | 2017-01-01 |
| JP2018510234A (ja) | 2018-04-12 |
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