CN108611865B - A kind of high fastness azobenzene polyurethane hydrophobic textile product processing method and its textile - Google Patents
A kind of high fastness azobenzene polyurethane hydrophobic textile product processing method and its textile Download PDFInfo
- Publication number
- CN108611865B CN108611865B CN201810392506.XA CN201810392506A CN108611865B CN 108611865 B CN108611865 B CN 108611865B CN 201810392506 A CN201810392506 A CN 201810392506A CN 108611865 B CN108611865 B CN 108611865B
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- CN
- China
- Prior art keywords
- azobenzene
- polyurethane
- hydrophobic
- processing method
- high fastness
- 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.)
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- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 62
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 239000004753 textile Substances 0.000 title claims abstract description 48
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 41
- 239000004814 polyurethane Substances 0.000 title claims abstract description 41
- 238000003672 processing method Methods 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 239000004744 fabric Substances 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- -1 alkyl isocyanate compound Chemical class 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 6
- WKODVHZBYIBMOC-UHFFFAOYSA-N chembl116175 Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(O)C=C1 WKODVHZBYIBMOC-UHFFFAOYSA-N 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 230000004048 modification Effects 0.000 claims description 6
- 238000012986 modification Methods 0.000 claims description 6
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- 239000004417 polycarbonate Substances 0.000 claims description 6
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 6
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 claims description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- 238000009990 desizing Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000007711 solidification Methods 0.000 claims description 5
- 230000008023 solidification Effects 0.000 claims description 5
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 claims description 3
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 claims description 3
- GFLXBRUGMACJLQ-UHFFFAOYSA-N 1-isocyanatohexadecane Chemical compound CCCCCCCCCCCCCCCCN=C=O GFLXBRUGMACJLQ-UHFFFAOYSA-N 0.000 claims description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 2
- IGQLTMLBFFIKBR-UHFFFAOYSA-N SCO[Si](OC)(C)CCCO Chemical compound SCO[Si](OC)(C)CCCO IGQLTMLBFFIKBR-UHFFFAOYSA-N 0.000 claims description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 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 claims 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 claims 1
- 230000008859 change Effects 0.000 abstract description 5
- 239000000835 fiber Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 238000012545 processing Methods 0.000 abstract description 3
- 238000005316 response function Methods 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 2
- 229920000742 Cotton Polymers 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 229940043237 diethanolamine Drugs 0.000 description 3
- 230000002045 lasting effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 206010034960 Photophobia Diseases 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 208000013469 light sensitivity Diseases 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 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 1
- 238000011056 performance test Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000005067 remediation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002351 wastewater Substances 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester 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
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
- D06M10/00—Physical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. ultrasonic, corona discharge, irradiation, electric currents, or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
- D06M10/001—Treatment with visible light, infrared or ultraviolet, X-rays
-
- 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
- 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
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
-
- 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
-
- 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/32—Polyesters
Abstract
The invention discloses a kind of high fastness azobenzene polyurethane hydrophobic textile product processing method and its textiles, the processing technology includes preparing azobenzene long alkyl chain type Hydrophobic Derivatives, prepare double bond containing azobenzene hydrophobic polyurethane, sulfhydryl modified textile is prepared, high fastness azobenzene polyurethane hydrophobic textile product are finally obtained.The processing method of the invention thermosetting mode traditional by light-initiated substitution, energy-saving and emission-reduction, reduce influence of the heat to fabric feeling and gloss, simultaneous selection azobenzene is under the irradiation of UV light and visible light, pass through cis-trans isomerism, change molecular structure, so as to realize the hydrophobic size control of textile.The present invention can effectively improve the disadvantage of the response function textile fastness difference of conventional coatings method preparation, have broad application prospects by the function textile of chemical reaction preparation photoresponse due to passing through chemical bonding between azobenzene molecule and fiber.
Description
Technical field
The present invention relates to belong to chemical field, and in particular to a kind of high fastness azobenzene polyurethane hydrophobic textile product processing
Method and its textile.
Background technique
Photosensitive textile has its good characteristic, has responsiveness to light, and hydrophilic and hydrophobic and the conversion of other performances can occur.It
More comfortable, safety and entertaining can be provided, provided for us and preferably experience and promoted working efficiency, it can more " clever "
Ground is customer service.People looking for novelty and gradually mentioning to Functional Requirement also with improvement of living standard to textile
It is high.Photosensitive textile has just catered to this consumer psychology of people, and demand is increasing, quickly grows in recent years.Therefore,
Photosensitive textile becomes the emphasis that textile industry is studied at present.
In azobenzene molecule one end, grafting and fiber-reactive group, the functional groups of other end grafted hydrophobic/hydrophilic lead to
Chemical reaction is crossed, the function textile of photoresponse can be prepared, and due to that, by chemical bonding, can have between azobenzene molecule and fiber
Effect improves the disadvantage of the standby response function textile fastness difference of traditional law system, has broad application prospects.Azo benzylcellulose
It is absorbing material, reversible change can occur for its structure under the stimulation of the Noninvasive and common light of respective wavelength, lead
Cause its physical property, such as color, shape, size, dissolubility and viscosity change.Such polymer is shown in many fields
Its application.Therefore, the synthesis of azo benzylcellulose, characterization and application are paid close attention to by academic and industrial circle research.
Summary of the invention
Goal of the invention: in view of the problems of the existing technology, it is an object of that present invention to provide a kind of high fastness azobenzenes
Polyurethane hydrophobic textile product and its processing method.Processing method of the invention by ultraviolet light-initiated sulfhydryl modified textile with
Double bond containing azobenzene hydrophobic polyurethane reaction, can assign the hydrophobicity of the high fastness to washing of textile.
The present invention also provides the high fastness azobenzene polyurethane hydrophobic textile product that above-mentioned processing method is processed
Technical solution: to achieve the goals above, a kind of high hydrophobic spinning of fastness azobenzene polyurethane as described herein
The processing method of fabric, includes the following steps:
(1) dibutyl tin dilaurate is added dropwise into the solution for dissolving 4,4 '-dihydroxy azobenzenes by ethyl acetate to urge
Agent, then the tetrahydrofuran solution containing long alkyl isocyanate compound is added dropwise, azobenzene long alkyl chain type is prepared after reaction
Hydrophobic Derivatives；
(2) isophorone diisocyanate and polycarbonate glycol 500 and polyethylene glycol 400 are added in container, oil bath
Reaction obtains base polyurethane prepolymer for use as, and N methyldiethanol amine is added dropwise, and carries out chain extending reaction；By azobenzene prepared by step (1)
Long alkyl chain type Hydrophobic Derivatives, which are directly added into the reaction system after the chain extension of step (2), is reacted, and end-capping reagent season is added
Penta tetrol triacrylate, then react and continue, acetone most is removed through rotating pressure-decreasing distillation afterwards, it is hydrophobic poly- to obtain double bond containing azobenzene
Urethane；
(3) it prepares the ethyl acetate solution containing mercaptosilane coupling agents and triethylamine is added, then will have been subjected to desizing kiering
Textile be impregnated in prepared solution, handled, then removal is sufficiently washed with dehydrated alcohol, dried, and obtains sulfydryl
Modified textile；
(4) sulfhydryl modified textile is impregnated in the double bond containing azobenzene hydrophobic polyurethane modification liquid that step (2) obtains
In, photoinitiator is added, then UV solidifies to get high fastness azobenzene polyurethane hydrophobic textile product in photo solidification machine.
Preferably, step (1) the long alkyl isocyanate compound is dodecyl isocyanate, cetyl is different
One or more of cyanate and octadecylisocyanate.
Wherein, ethyl acetate described in step (1) every 100mL dissolves 4,4 '-dihydroxy azobenzene of 2.5-4.2g.It is every simultaneously
Two to three drop dibutyl tin dilaurates can be added after 100mL ethyl acetate dissolution 2.5-4.2g 4,4 '-dihydroxy azobenzene
Catalyst,
Wherein, 3-3.5g long alkyl isocyanate compound is dissolved in tetrahydrofuran solution described in step (1) every 50mL.
Preferably, step (1) and with column chromatography (eluent: ethyl acetate/dichloromethane=1/5, volume ratio) into
One step separating-purifying.
Wherein, step (2) the oil bath reaction is to be warming up to 80-90 DEG C of reaction 1h.It can be by the different Buddhist of 10g in step (2)
That ketone diisocyanate and 8g polycarbonate glycol 500 and 3g polyethylene glycol 400 add to three mouthfuls equipped with stirring rod and condenser pipe
In flask, oil bath is warming up to 80-90 DEG C of reaction 1h.
Step (2) chain extending reaction is 50 DEG C of chain extending reaction 30-40min.
Wherein, the mercaptosilane coupling agents for being 15-40% containing mass concentration in step (3) described ethyl acetate solution.
Preferably, step (3) mercaptosilane coupling agents are γ-mercaptopropyl trimethoxysilane, γ-mercapto propyl three
Ethoxysilane, 2- mercaptoethyl triethoxysilane, in mercapto hydroxypropyl methyl dimethoxysilane in any one.
Wherein, step (3) textile is cotton fabric or itself and terylene, polyamide fibre, acrylic fibers, wool or viscose fiber
Blended fabric.
Wherein, step (4) photoinitiator be photoinitiator 1173, photoinitiator 184, in photoinitiator TPO extremely
Few one kind.
The high fastness azobenzene polyurethane hydrophobic textile product that processing method of the present invention is processed.
The present invention induces urethane monomer to polymerize using light as initiation means, and by the double bond containing azo containing hydrophobic long-chain
Benzene hydrophobic polyurethane and the modified fabric polymerization reaction for having sulfydryl, and selecting azobenzene is because containing in azobenzene photosensitive molecular
There is the azobenzene group of light sensitivity, under the irradiation of UV light and visible light, by cis-trans isomerism, changes molecular structure, so as to
To realize the hydrophobic size control of textile, realize that fabric has the intelligent response of dynamic moisture.Since it is with light
Quick isomery reversibility is superior, light sensitivity is high and electrochemistry is active and is widely paid close attention to, and can be applied to preparation photoresponse
Functional material, drug release, environment remediation etc..
The utility model has the advantages that compared with prior art, the present invention has the advantage that
Processing of the invention will not damage environment using luminous energy as initiation means cleanliness without any pollution；Energy-saving and emission-reduction save
A large amount of thermal energy is removed, while the generation without waste water, exhaust gas.The processing method only light requirement source device, processing sample homogeneity is good, letter
It is single efficient, at low cost, yield height etc..
The azobenzene polyurethane hydrophobic textile product that the present invention processed the obtain thermosetting side traditional by light-initiated substitution
Formula reduces influence of the heat to fabric feeling, gloss and strength, due to that, by chemical bonding, can have between azobenzene molecule and fiber
Effect improves the disadvantage of the response function textile fastness difference of conventional coatings method preparation, has broad application prospects.And pass through
Cis-trans isomerism changes molecular structure, can also realize the hydrophobic size control of textile, has intelligent response.
Detailed description of the invention
Fig. 1 is the contact angle performance schematic diagram of the high hydrophobic pure cotton fabric of fastness azobenzene polyurethane of the invention.
Specific embodiment
Below in conjunction with drawings and examples, the invention will be further described.
Embodiment 1
4,4 '-dihydroxy azobenzene of 2.8g is dissolved using 100mL ethyl acetate, two drop dibutyl tin dilaurates are added
Then 3g octadecylisocyanate is dissolved in 50mL tetrahydrofuran solution and is added dropwise to 4,4 '-dihydroxy by catalyst
In azo benzole soln, 2h is reacted at 45 DEG C, prepares azobenzene long alkyl chain type Hydrophobic Derivatives, and (eluted with column chromatography
Liquid: ethyl acetate/dichloromethane=1/5, volume ratio) further separating-purifying.
10g isophorone diisocyanate and 8g polycarbonate glycol 500 and 3g polyethylene glycol 400 are added to equipped with stirring
In the three-necked flask of stick and condenser pipe, oil bath is warming up to 80 DEG C of reaction 1h, obtains base polyurethane prepolymer for use as, and 2.1g N- methyl is added dropwise
Diethanol amine, and at 50 DEG C carry out chain extending reaction 40min；Prepared azobenzene long alkyl chain type Hydrophobic Derivatives are straight
It connects in the reaction system after chain extension is added, 2h is reacted at 60 DEG C, then reduce temperature to 50 DEG C of reaction 2h, end-capping reagent season is added
Penta tetrol triacrylate 1.6g, then lasting 4h is reacted, acetone most is removed through rotating pressure-decreasing distillation afterwards, obtains double bond containing azobenzene
Hydrophobic polyurethane；
The ethyl acetate solution of the gamma-mercaptopropyltriethoxysilane of 20% mass concentration is prepared, 5% mass is then added
The triethylamine (ethyl acetate solution relative to gamma-mercaptopropyltriethoxysilane) of score, then will have been subjected to desizing kiering
Pure cotton fabric be impregnated in prepared solution (mass ratio 1:50), handle 2h, then removal sufficiently washed with dehydrated alcohol,
Drying, obtains sulfhydryl modified pure cotton fabric；
Sulfhydryl modified pure cotton fabric is impregnated in the double bond containing azobenzene hydrophobic polyurethane modification liquid that solid content is 10%
In, cotton fabric and modification liquid mass ratio 1:50 are added photoinitiator 1173, make its azobenzene hydrophobic polyurethane quality with double bond
Than 1:5, then UV solidifies 1min to get the high hydrophobic pure cotton fabric of fastness azobenzene polyurethane in photo solidification machine.
Embodiment 2
4,4 '-dihydroxy azobenzene of 2.5g is dissolved using 100mL ethyl acetate, two drop dibutyl tin dilaurates are added
Then 3g hexadecyl isocyanate is dissolved in 50mL tetrahydrofuran solution and is added dropwise to 4,4 '-dihydroxy by catalyst
In azo benzole soln, 2h is reacted at 45 DEG C, prepares azobenzene long alkyl chain type Hydrophobic Derivatives, and (eluted with column chromatography
Liquid: ethyl acetate/dichloromethane=1/5, volume ratio) further separating-purifying.
10g isophorone diisocyanate and 8g polycarbonate glycol 500 and 3g polyethylene glycol 400 are added to equipped with stirring
In the three-necked flask of stick and condenser pipe, oil bath is warming up to 90 DEG C of reaction 1h, obtains base polyurethane prepolymer for use as, and 2.1g N- methyl is added dropwise
Diethanol amine, and at 50 DEG C carry out chain extending reaction 30min；Prepared azobenzene long alkyl chain type Hydrophobic Derivatives are straight
It connects in the reaction system after chain extension is added, 2h is reacted at 60 DEG C, then reduce temperature to 50 DEG C of reaction 2h, end-capping reagent season is added
Penta tetrol triacrylate 1.6g, then lasting 4h is reacted, acetone most is removed through rotating pressure-decreasing distillation afterwards, obtains double bond containing azobenzene
Hydrophobic polyurethane；
The ethyl acetate solution of the gamma-mercaptopropyltriethoxysilane of 15% mass concentration is prepared, the three of 5% are then added
Ethamine (ethyl acetate solution relative to gamma-mercaptopropyltriethoxysilane) has been subjected to the pure cotton fabric dipping of desizing kiering
In prepared solution (mass ratio 1:50), 2h is handled, then removal is sufficiently washed with dehydrated alcohol, dried, and obtains sulfydryl
Modified cotton-polyester blend fabric；
Sulfhydryl modified cotton-polyester blend fabric is impregnated in the double bond containing azobenzene hydrophobic polyurethane that solid content is 10% to change
Property liquid in, photoinitiator 184 is added in cotton-polyester blend fabric and modification liquid mass ratio 1:50, keeps it hydrophobic with the azobenzene of double bond
Polyurethane mass ratio 1:5, then in photo solidification machine UV solidify 1min washed to get the high hydrophobic cotton of fastness azobenzene polyurethane it is mixed
Textile fabric.
Embodiment 3
4,4 '-dihydroxy azobenzene of 4.2g is dissolved using 100mL ethyl acetate, three drop dibutyl tin dilaurates are added
Then 3g dodecyl isocyanate is dissolved in 50mL tetrahydrofuran solution and is added dropwise to 4,4 '-dihydroxy by catalyst
In azo benzole soln, 2h is reacted at 45 DEG C, prepares azobenzene long alkyl chain type Hydrophobic Derivatives, and (eluted with column chromatography
Liquid: ethyl acetate/dichloromethane=1/5, volume ratio) further separating-purifying.
10g isophorone diisocyanate and 8g polycarbonate glycol 500 and 3g polyethylene glycol 400 are added to equipped with stirring
In the three-necked flask of stick and condenser pipe, oil bath is warming up to 85 DEG C of reaction 1h, obtains base polyurethane prepolymer for use as, and 2.1g N- methyl is added dropwise
Diethanol amine, and at 50 DEG C carry out chain extending reaction 35min；Prepared azobenzene long alkyl chain type Hydrophobic Derivatives are straight
It connects in the reaction system after chain extension is added, 2h is reacted at 60 DEG C, then reduce temperature to 50 DEG C of reaction 2h, end-capping reagent season is added
Penta tetrol triacrylate 1.6g, then lasting 4h is reacted, acetone most is removed through rotating pressure-decreasing distillation afterwards, obtains double bond containing azobenzene
Hydrophobic polyurethane；
The ethyl acetate solution of the 2- mercaptoethyl triethoxysilane of 40% mass concentration is prepared, is then added 5%
Triethylamine (ethyl acetate solution relative to 2- mercaptoethyl triethoxysilane) has been subjected to the pure cotton fabric leaching of desizing kiering
Stain handles 2h, then removal is sufficiently washed with dehydrated alcohol, dried, and obtains mercapto in prepared solution (mass ratio 1:50)
Base is modified cotton/glutinous blended fabric；
Sulfhydryl modified cotton/glutinous blended fabric is impregnated in the double bond containing azobenzene hydrophobic polyurethane that solid content is 10% to change
Property liquid in, photoinitiator TPO is added in cotton/glutinous blended fabric and modification liquid mass ratio 1:50, keeps it hydrophobic with the azobenzene of double bond
Polyurethane mass ratio 1:5, then UV solidifies 1min to get the high hydrophobic cotton of fastness azobenzene polyurethane/glutinous in photo solidification machine
Blended fabric.
Test example 1
Modified fabric performance is characterized by following performance test:
(1) contact angle test: under normal temperature conditions, fabric contact angle is surveyed using DSA100 Drop Shape Analyzer
Examination, water 8uL, water droplet are read after contacting 20s with fabric, and same fabric measures 3 times in different location, take its average value.
(2) hydrophobic durability test: the hydrophobic durability of fabric is according to " fabric color fastness tests fastness to soaping " mark
Quasi- (GB/T 3921-2008) is measured, and configures the liquid of soaping of soap flakes containing standard 5g/L and natrium carbonicum calcinatum 2g/L, and bath raio is
1:50, fabric sample wash 30min at a temperature of 60 DEG C, after cleaned and dried.
The embodiment of the present invention 1 processes the contact angle performance of the obtained high hydrophobic pure cotton fabric of fastness azobenzene polyurethane,
As shown in Figure 1, can reach 150 or more, and its hydrophobicity is held essentially constant after washing 10 times, fastness to washing reaches 5 grades.
Claims (10)
1. a kind of processing method of high fastness azobenzene polyurethane hydrophobic textile product, which comprises the steps of:
(1) dibutyl tin dilaurate catalyst is added dropwise into the solution for dissolving 4,4 '-dihydroxy azobenzenes by ethyl acetate,
The tetrahydrofuran solution containing long alkyl isocyanate compound is added dropwise again, prepares that azobenzene long alkyl chain type is hydrophobic to spread out after reaction
Biology；
(2) isophorone diisocyanate and polycarbonate glycol 500 and polyethylene glycol 400 are added in container, oil bath reaction,
Base polyurethane prepolymer for use as is obtained, N methyldiethanol amine is added dropwise, carries out chain extending reaction；By the long alkane of azobenzene prepared by step (1)
Base chain Hydrophobic Derivatives, which are directly added into the system after the chain extending reaction of step (2), is reacted, and end-capping reagent Ji Wusi is added
Alcohol triacrylate, then react and continue, acetone most is removed through rotating pressure-decreasing distillation afterwards, obtains the hydrophobic poly- ammonia of double bond containing azobenzene
Ester；
(3) it prepares the ethyl acetate solution containing mercaptosilane coupling agents and triethylamine is added, then will have been subjected to the spinning of desizing kiering
Fabric is impregnated in prepared solution, is handled, and then removal is sufficiently washed with dehydrated alcohol, dried, and is obtained sulfhydryl modified
Textile；
(4) sulfhydryl modified textile is impregnated in the double bond containing azobenzene hydrophobic polyurethane modification liquid that step (2) obtains, is added
Enter photoinitiator, then UV solidifies to get high fastness azobenzene polyurethane hydrophobic textile product in photo solidification machine.
2. the processing method of high fastness azobenzene polyurethane hydrophobic textile product according to claim 1, which is characterized in that
Step (1) the long alkyl isocyanate compound is dodecyl isocyanate, hexadecyl isocyanate and octadecyl
One or more of isocyanates.
3. the processing method of high fastness azobenzene polyurethane hydrophobic textile product according to claim 1, which is characterized in that
Ethyl acetate described in step (1) every 100mL dissolves 2.5-4.2g 4,4 '-dihydroxy azobenzene.
4. the processing method of high fastness azobenzene polyurethane hydrophobic textile product according to claim 1, which is characterized in that
3-3.5g long alkyl isocyanate compound is dissolved in tetrahydrofuran solution described in step (1) every 50mL.
5. the processing method of high fastness azobenzene polyurethane hydrophobic textile product according to claim 1, which is characterized in that
Step (2) the oil bath reaction is to be warming up to 80-90 DEG C of reaction 1h.
6. the processing method of high fastness azobenzene polyurethane hydrophobic textile product according to claim 1, which is characterized in that
Step (2) chain extending reaction is 50 DEG C of chain extending reaction 30-40min.
7. the processing method of high fastness azobenzene polyurethane hydrophobic textile product according to claim 1, which is characterized in that
The mercaptosilane coupling agents for being 15-40% containing mass concentration in step (3) described ethyl acetate solution.
8. the processing method of high fastness azobenzene polyurethane hydrophobic textile product according to claim 1, which is characterized in that
Step (3) mercaptosilane coupling agents are γ-mercaptopropyl trimethoxysilane, gamma-mercaptopropyltriethoxysilane, 2- sulfydryl
Any one in ethyl triethoxysilane, mercapto hydroxypropyl methyl dimethoxysilane.
9. the processing method of high fastness azobenzene polyurethane hydrophobic textile product according to claim 1, which is characterized in that
Step (4) photoinitiator is at least one of photoinitiator 1173, photoinitiator 184, photoinitiator TPO.
10. the high fastness azobenzene polyurethane that a kind of any processing method of claim 1-9 is processed is hydrophobic
Textile.
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