CN117265875A - Treating agent and fiber fabric or coating - Google Patents
Treating agent and fiber fabric or coating Download PDFInfo
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- CN117265875A CN117265875A CN202310988989.0A CN202310988989A CN117265875A CN 117265875 A CN117265875 A CN 117265875A CN 202310988989 A CN202310988989 A CN 202310988989A CN 117265875 A CN117265875 A CN 117265875A
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- Prior art keywords
- meth
- alkyl
- acrylate
- equal
- group
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 50
- 239000004744 fabric Substances 0.000 title claims abstract description 37
- 239000000835 fiber Substances 0.000 title claims abstract description 24
- 238000000576 coating method Methods 0.000 title claims abstract description 20
- 239000011248 coating agent Substances 0.000 title claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 131
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 62
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000010703 silicon Substances 0.000 claims abstract description 42
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 42
- 239000005871 repellent Substances 0.000 claims abstract description 17
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 13
- 239000012736 aqueous medium Substances 0.000 claims abstract description 7
- 230000003373 anti-fouling effect Effects 0.000 claims abstract description 6
- 229920001558 organosilicon polymer Polymers 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 116
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- -1 Cyclic hydrocarbon radicals Chemical class 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 79
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 73
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 70
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 69
- 125000002947 alkylene group Chemical group 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 30
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 239000000839 emulsion Substances 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 20
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 8
- 239000002736 nonionic surfactant Substances 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000003093 cationic surfactant Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 125000003438 dodecyl group Chemical group [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])* 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 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 claims description 5
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 3
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003901 ceryl 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])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 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000755 henicosyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002960 margaryl 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])[H] 0.000 claims description 3
- 125000001802 myricyl 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])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 description 3
- 125000001421 myristyl 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])[H] 0.000 claims description 3
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 claims description 3
- 125000002958 pentadecyl 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])[H] 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 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 description 3
- 239000002280 amphoteric surfactant Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000004513 sizing Methods 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 21
- 230000002940 repellent Effects 0.000 abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 150000002430 hydrocarbons Chemical group 0.000 description 19
- 238000012360 testing method Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 125000000732 arylene group Chemical group 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- ITRHZTGVVSWIDC-UHFFFAOYSA-N 11-methyl-1-(11-methyldodecoxy)dodecane Chemical compound CC(C)CCCCCCCCCCOCCCCCCCCCCC(C)C ITRHZTGVVSWIDC-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 4
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 150000001924 cycloalkanes Chemical class 0.000 description 4
- 150000001925 cycloalkenes Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl 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])[H] 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003725 azepanyl group Chemical group 0.000 description 3
- 229960003237 betaine Drugs 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- JFUWJIKJUNAHEN-UHFFFAOYSA-N 1-ethenyl-3-ethylpyrrolidin-2-one Chemical compound CCC1CCN(C=C)C1=O JFUWJIKJUNAHEN-UHFFFAOYSA-N 0.000 description 2
- CRJHKHYPIUPQSX-UHFFFAOYSA-N 1-ethenyl-4,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(=O)N(C=C)C1C CRJHKHYPIUPQSX-UHFFFAOYSA-N 0.000 description 2
- JBKFPCSZNWLZAS-UHFFFAOYSA-N 1-ethenyl-4-methylpiperidin-2-one Chemical compound CC1CCN(C=C)C(=O)C1 JBKFPCSZNWLZAS-UHFFFAOYSA-N 0.000 description 2
- IXUHPUSIYSUGNR-UHFFFAOYSA-N 1-ethenyl-5,5-dimethylpyrrolidin-2-one Chemical compound CC1(C)CCC(=O)N1C=C IXUHPUSIYSUGNR-UHFFFAOYSA-N 0.000 description 2
- DJABNVJZYFGAJE-UHFFFAOYSA-N 1-ethenyl-5-ethylpyrrolidin-2-one Chemical compound CCC1CCC(=O)N1C=C DJABNVJZYFGAJE-UHFFFAOYSA-N 0.000 description 2
- RESPXSHDJQUNTN-UHFFFAOYSA-N 1-piperidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCCC1 RESPXSHDJQUNTN-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000002393 azetidinyl group Chemical group 0.000 description 2
- 125000004069 aziridinyl group Chemical group 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000002704 decyl group Chemical group [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])* 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
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- WDFKEEALECCKTJ-UHFFFAOYSA-N n-propylprop-2-enamide Chemical compound CCCNC(=O)C=C WDFKEEALECCKTJ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004928 piperidonyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000012502 risk assessment Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000011850 water-based material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 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
- D06M15/21—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F130/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F130/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F130/08—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- C—CHEMISTRY; METALLURGY
- 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
- C09D143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
-
- 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
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/11—Oleophobic properties
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present application relates to a treating agent and a treated fiber fabric or coating thereof. The treating agent comprises an organosilicon polymer, an emulsifying agent and an aqueous medium, wherein the organosilicon polymer comprises structural units generated by a monomer I, the monomer I comprises a silicon monomer I-A and an optional silicon monomer I-B, and all the monomers are defined as the specification. The treating agent can simultaneously endow the fiber fabric with good oil and water repellent function and good antifouling or anti-graffiti capability of the coating.
Description
Technical Field
The present application relates to a treating agent and a treated fiber fabric or coating thereof.
Technical Field
In the past, fluoropolymers have been used for the surface water-repellent and oil-repellent treatment of fiber fabrics, and since the surface tension of the fluoropolymers is low, the surface properties of the fiber fabrics can be changed, but the appearance and the like of the fiber fabrics are not affected, and thus the fluoropolymers have been widely used.
However, in recent years, as the international society has increased attention to polyfluoroalkyl compounds (PFAS), month 3 of 2023, the european union chemical administration (ECHA) has opened public consultations concerning the increased restrictions on PFAS manufacture, release and use proposals in REACH restrictions (REACH appendix XIVII) submitted to ECHA in denmark, germany, the netherlands, norway and sweden, with the aim of giving the interested parties the opportunity to take PFAS REACH restrictions for regulatory comments, and after the public consultation has ended. The ECHA's Committee for Risk Assessment (RAC) and socioeconomic analysis Committee (SEAC) will evaluate proposed restrictions and develop comments based on consultation comments, ultimately being governed by the European Committee's decision whether to incorporate PFAS into restrictions.
In view of the above, new non-fluorine compounds have been proposed to replace existing fluorine-containing finishes.
CN107849187a proposes a polymer formed by copolymerizing acrylic acid ester and vinyl chloride, which has a good water repellent effect on textile finishing.
CN105765025B proposes a copolymer of long chain alkyl acrylate, the resulting polymer also has good water repellent effect for finishing textiles. CN105764980B and CN 105745272B both use similar processes to synthesize treatment agents to achieve water repellency.
CN114573768B proposes a polymer self-dispersible in water using silicone, and the formed polymer finishes a fiber fabric, and has a certain water-repellent effect and an oil-repellent effect, but the water-repellent effect is not outstanding.
It is therefore desirable to invent a non-fluorine based treatment agent that has excellent water repellency while having oil repellency that is effective against a variety of stains both water-based and oil-based.
Disclosure of Invention
In a first aspect, the present application provides a silicone polymer obtained by emulsion polymerization, which can be used for the water-and oil-repellent treatment of fibrous fabrics or for the anti-fouling or anti-graffiti treatment of paints.
In particular, the silicone polymers provided herein include structural units derived from monomer I, which includes silicon monomer I-A and optionally silicon monomer I-B,
a) The structural general formula of the silicon monomer I-A is shown in the formula I-A:
M-Z 1 or Z is 1 -M-Z 1
Formula I-A
Wherein M contains a polymerizable functional group;
Z 1 selected from the structures shown below:
Z 1 wherein R is 4 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 20 An alkylene group of 1.ltoreq.a.ltoreq.200;
Y 1 and Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Or of formula (1), and further satisfies Y when a is 1 1 And/or Y 2 Is of the formula (1), at least one Y when a is greater than 1 and less than or equal to 200 1 Is a structure of formula (1) and/or at least one Y 2 Is a structure of formula (1):
R 7 each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Is an alkylaryl group of (C)Radical, C 1 -C 20 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 20 The alkylene of (2) is more than or equal to 0 and less than or equal to 200;
b) The structural general formula of the silicon monomer I-B is shown in the formula I-B:
M-Z 2 or Z is 2 -M-Z 2
Formula I-B
Wherein M contains a polymerizable functional group;
Z 2 selected from the group consisting of the structures shown in the following,
Z 2 wherein R is 3 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 4 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 20 Is not less than 1 and not more than 200.
In some embodiments, the polymerizable functional group in M is selected from groups containing carbon-carbon double bonds.
In some embodiments, in formula I-A and/or formula I-B, M is as shown in formula I-1:
CH 2 ＝C(R 1 )-X-B-
I-1
in the formula I-1, R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl of (a); b is selected from C 1 -C 20 Alkylene group, C 6 -C 20 And combinations thereof,
x is selected from the group shown as X-1 and X-2,
-C(O)-O-
X-1
-C(O)-N(R 2 )-
X-2
R 2 selected from hydrogen atoms or C 1 -C 20 Is a hydrocarbon group.
In some embodiments, in formula I-1, R 1 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments, in formula I-1, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-1, B is C 6 -C 15 Arylene groups of (2), e.g. C 6 -C 9 Arylene of (C) 10 -C 12 Arylene or C of (2) 13 -C 15 Arylene group of (a).
In some embodiments, R in the groups represented by X-1 and X-2 2 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group.
In some embodiments, in formula I-1, R 1 Selected from a hydrogen atom or a methyl group; b is C 1 -C 6 An alkylene group of (a); x, R 2 Selected from hydrogen atoms or methyl groups.
In some embodiments, in formula I-A and/or formula I-B, M is as shown in formula I-2:
CH 2 ＝C(R 1 )-W-B-
I-2
in the formula I-2, R 1 Selected from hydrogen atoms or C 1 -C 20 An alkyl group;
w is selected from the group shown in W-1, W-2, W-3 and W-4,
-O-C(O)-N(R 2 )- W-2
-O-C(O)-O- W-3
-O-C(O)-O-D-N(R 2 )- W-4
R 2 selected from hydrogen atoms or C 1 -C 20 Alkyl, D is C 1 -C 20 An alkylene group of (a); when W is selected from W-1, B is absent or C 1 -C 20 When W is selected from W-2, W-3,W-4, B is selected from C 1 -C 20 Alkylene group, C 6 -C 20 Aryl groups of (a) and combinations thereof.
In some embodiments, in formula I-2, R 1 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments, in formula I-2, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-2, R 2 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments, in formula I-2, D is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-2, R 1 And R is 2 Selected from hydrogen atoms or methyl groups, B and D being C 1 -C 6 Alkylene groups of (a).
In some embodiments, when W is selected from W-1, B is absent or C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, when W is selected from W-2, W-3,W-4, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, when W is selected from W-2, W-3,W-4, B is C 6 -C 15 Arylene groups of (2), e.g. C 6 -C 9 Arylene of (C) 10 -C 12 Arylene or C of (2) 13 -C 15 Arylene group of (a).
In some embodiments, in formula I-A and/or formula I-B, M is as shown in formula I-3:
in the formula I-3, R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl, B is independently selected from C 1 -C 20 Alkylene group, C 6 -C 20 Aryl groups of (a) and combinations thereof.
In some embodiments, in formula I-3, R 1 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments, in formula I-3, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-3, B is C 6 -C 15 Arylene of (2)Radicals, e.g. C 6 -C 9 Arylene of (C) 10 -C 12 Arylene or C of (2) 13 -C 15 Arylene group of (a).
In some embodiments, in formula I-3, R 1 Selected from hydrogen atoms or methyl groups.
In some embodiments, Z 1 Wherein R is 4 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 10 And/or 1.ltoreq.a.ltoreq.100, e.g.1.ltoreq.a.ltoreq.80; r is R 7 Each independently is C 1 -C 10 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 10 And/or 0.ltoreq.b.ltoreq.100, e.g.0.ltoreq.b.ltoreq.80.
In some embodiments, Z 1 Wherein R is 4 Each independently is C 1 -C 6 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R 5 -O-R 6 -a group, R 5 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 6 Is C 1 -C 6 An alkylene group of 1.ltoreq.a.ltoreq.30; r is R 7 Each independently is C 1 -C 6 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 6 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 10 Is C 1 -C 6 The alkylene group of (2) is more than or equal to 0 and less than or equal to 30.
In some embodiments, a is an integer from 1 to 80, an integer from 1 to 30, an integer from 1 to 20, or an integer from 1 to 10.
In some embodiments, b is 0. In some embodiments, b is an integer from 1 to 30, an integer from 1 to 20, an integer from 1 to 10, or an integer from 1 to 5.
Specifically indicated, R 4 ，R 8 Representative is C 1 -C 20 Alkyl of C 1 -C 20 Alkoxy, C 6 -C 20 Of the aryl radicals, in particular C 1 -C 8 Alkyl of C 1 -C 4 Alkoxy groups of (a). For example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, and the like. Aryl groups such as phenyl, tolyl, naphthyl, and the like. R is R 4 ，R 8 It is also possible to have such a structure (R 5 -O-R 6 )-，R 5 Is C 1 -C 10 Alkyl of R 6 Is C 1 -C 10 Alkylene groups of (2), more commonly such as CH 3 O(CH 2 ) x -and the like. R is R 6 Is a slave C 1 -C 20 Alkyl groups and C of (C) 6 -C 20 For example, an aryl group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, hexadecyl and the like, and an aryl group such as phenyl, tolyl, naphthyl and the like.
In some embodiments, Z 1 One or more selected from the following structures i-1 to i-4:
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, R is C 1 -C 3 For example methyl.
In some preferred embodiments, Z 1 Selected from the following structures:
one or more of the following;
me represents methyl, 1.ltoreq.m+1.ltoreq.60, preferably 1.ltoreq.m+1.ltoreq.30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, Z 2 Wherein R is 3 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 4 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 10 Alkylene groups of (a).
In some embodiments, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 100. In some embodiments, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 80. According to some embodiments of the present application, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 30. According to some embodiments of the present application, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 20. According to some embodiments of the present application, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 10.
In some embodiments, Z 2 Wherein R is 3 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 4 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 6 Is C 1 -C 10 Is not less than 1 and not more than 10.
In some embodiments, Z 2 One or more selected from the following structures ii-1 to ii-2:
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl of (a)Or C 7 -C 12 Alkylaryl groups of (a);
m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, Z 2 Selected from the following structures:
one or more of the following;
me represents methyl, ph represents phenyl; m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, m is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.
In some embodiments, x is 1, 2, 3, 4, 5, 6, or 7.
In some embodiments, silicon monomer I-A is selected from
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝C(CH 3 )C(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-NH-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝CHC(O)-NH-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-CH 2 -Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(CH 3 )[O-[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ] 2 ，0≤n≤25；
CH 2 ＝CH-ph-Si(OSi(CH 3 ) 3 ) 3 (ph represents)；
CH 2 ＝CH-ph-(CH 2 ) 2 Si(OSi(CH 3 ) 3 ) 3 (ph represents)；
CH 2 ＝CH-O-C(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 2 -NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ] 2 ；
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ] 2 。
In some embodiments, silicon monomer I-B is selected from
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 8 H 17 ，1≤n≤25；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ，1≤n≤25；
CH 2 ＝CH-ph-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl, ph represents )，1≤n≤25；
CH 2 ＝CH-O-C(O)-NH-(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 2 -NH-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl),
1≤n≤25；
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝C(CH 3 )-C(O)-N[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25.
In some embodiments, the silicone polymer further comprises structural units derived from monomer II,
CH 2 ＝C(R 1 )-C(O)-O-R 3 II
R 1 is a hydrogen atom or C 1 -C 20 An alkyl group; r is R 3 Is C 1 -C 40 Alkyl, C 4 -C 30 Cyclic hydrocarbons or C 7 -C 20 Alkylaryl groups.
In some embodiments, in formula II, R 1 Is a hydrogen atom or C 1 -C 10 Alkyl radicals, preferably hydrogen atoms or C 1 -C 6 Alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or n-hexyl.
In some embodiments, in formula II, R 3 Selected from C 1 -C 30 Alkyl or C 4 -C 20 Cyclic hydrocarbon groups. In some embodiments, in formula II, R 3 Selected from C 1 -C 10 Alkyl, C 11 -C 20 Alkyl, C 20 -C 30 Alkyl, C 4 -C 10 Cycloalkyl, C 11 -C 20 Cycloalkane, C 31 -C 30 Cycloalkane, C 4 -C 10 Cycloalkenyl, C 11 -C 20 Cycloolefin, C 31 -C 30 Cycloolefin, C 7 -C 15 Alkylaryl groups.
In some embodiments, monomer II is selected from one or more of methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, dodecyl (meth) acrylate, myristyl (meth) acrylate, pentadecyl (meth) acrylate, cetyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate, eicosyl (meth) acrylate, heneicosyl (meth) acrylate, docosyl (meth) acrylate, hexacosyl (meth) acrylate, triacontyl (meth) acrylate, cyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, benzyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentadienyl (meth) acrylate, tricyclopentyl (meth) acrylate, adamantyl (meth) acrylate, 2-methyl-2-adamantyl (meth) acrylate, or 2-ethyl-2-adamantyl (meth) acrylate.
In some embodiments, the silicone polymer does not include structural units derived from monomer IV, wherein monomer IV is selected from one or more of dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, diethylaminoethyl (meth) acrylate, diethylaminopropyl (meth) acrylate, N-t-butylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylamide, diethylaminoethyl (meth) acrylamide, dipropylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, diethylaminopropyl (meth) acrylamide, or dipropylaminopropyl (meth) acrylamide.
In some embodiments, the structural formula of monomer IV is as shown in formula IV:
CH 2 ＝C(R 1 )-P-B-N(R 3 R 4 ) IV
in the formula IV, P is selected from groups shown as P-1 and P-2,
-C(O)-O-
P-1
-C(O)-N(R 2 )-
P-2
b is C 1 -C 20 An alkylene group of (a); r is R 1 And R is 2 Each independently is a hydrogen atom or C 1 -C 20 An alkyl group; r is R 3 And R4 are each independently a hydrogen atom, C 1 -C 18 Alkyl, hydroxyethyl or benzyl, or R 3 And R is 4 And combine with the nitrogen atom to form morpholino, piperidino, or pyrrolidino.
In some embodiments, the proportion of structural units produced by silicon monomer I-a in the total amount of structural units produced by silicon monomer I-a to structural units produced by silicon monomer I-B is 1% to 100%,5% to 100%,10% to 100%, or 50% to 100%, e.g., 1%, 5%, 10%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, or any two of them, in mass percent. The total amount of structural units produced by silicon monomer I-A and structural units produced by silicon monomer I-B, i.e., the total amount of structural units produced by monomer I.
In some embodiments, monomer I produces structural units in a mass content of 30% to 100%. In some embodiments, monomer I produces structural units in a mass content of 40% to 85%. In some embodiments, monomer I produces structural units in a mass content of 50% to 80%. In some embodiments, monomer I produces structural units in a mass content of 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or a range of any two compositions thereof.
In some embodiments, monomer II produces structural units in a mass content of 5% to 70%. In some embodiments, monomer II produces structural units in a mass content of 10% to 70%. In some embodiments, monomer II produces structural units in a mass content of 15% to 50%. In some embodiments, monomer II produces structural units in a mass content of 20% to 45%. In some embodiments, monomer II produces structural units in a mass content of 5%, 7%, 10%, 20%, 25%, 35%, 40%, 45%, 50%, 55%, 60%, 65% or a range of any two compositions thereof.
In some embodiments, the silicone polymer further comprises structural units derived from a crosslinking monomer III, which is a compound having two reactive groups and/or an unsaturated carbon-carbon double bond (preferably a (meth) acrylate), and may also be a compound having at least 2 unsaturated carbon-carbon double bonds (preferably a (meth) acrylate), or a compound having at least one unsaturated carbon-carbon double bond and at least one reactive group, examples of which are preferably hydroxyl, epoxy, chloromethyl, blocked isocyanate, amino or carboxyl groups, and the like.
In some embodiments, crosslinking monomer III may be selected from one or more of diacetone (meth) acrylamide, N-methylol (meth) acrylamide, 3-chloro-2-hydroxypropyl (meth) acrylate, 2-acetoacetylethyl (meth) acrylate, glycidyl (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, or the 2-butanone oxime adduct of ethyl ester of 2-isocyanato (meth) acrylate.
In some embodiments, the silicone polymer does not include structural units derived from monomer V, wherein monomer V is selected from one or more of 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, or methoxypolyethylene glycol (meth) acrylate.
In some embodiments, monomer V has the general structural formula shown in formula V:
CH 2 ＝C(R 1 )-G-(R 2 O) q -R 3 V
in the formula V, R 1 Represents a hydrogen atom or a methyl group, R 2 Each independently is C 1 -C 6 Alkylene of (C) is preferred 2 -C 4 Q is an integer from 1 to 50, preferably an integer from 1 to 20; r is R 3 Represents a hydrogen atom or C 1 -C 20 Alkyl radicals of (2), preferably hydrogen atoms or C 1 -C 10 More preferably a hydrogen atom, C 1 -C 3 Alkyl of (a);
wherein G is selected from the group shown in G-1 and G-2,
-C(O)-O-B-
G-1
-C(O)-N(R 4 )-B-
G-2
r4 represents a hydrogen atom or a methyl group, B is absent or C 1 -C 20 Alkylene of (2), preferably absent or C 1 -C 10 Alkylene groups of (a).
In some embodiments, in formula V, R 2 Is C 2 -C 4 Alkylene groups of (a). In some embodiments, q is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, or 49 in formula V. In some embodiments, in formula V, q is an integer from 1 to 20.
In some embodiments, in formula V, R 3 Is a hydrogen atom or C 1 -C 10 Alkyl radicals of (2), e.g. hydrogen atoms, C 1 -C 3 Alkyl or C of (2) 4 -C 6 Is a hydrocarbon group.
In some embodiments, B is absent or C in the groups shown in G-1 and G-2 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene or C of (2) 4 -C 6 Alkylene groups of (a).
In some embodiments, the silicone polymer does not include structural units derived from monomer VI, wherein, the monomer VI is selected from the group consisting of N-vinyl-2-pyrrolidone, N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-3, 3-dimethyl-2-pyrrolidone, N-vinyl-5-ethyl-2-pyrrolidone, N-vinyl-3-ethylpyrrolidone, N-vinyl-4, 5-dimethylpyrrolidone, N-vinyl-5, 5-dimethylpyrrolidone, N-vinyl-3, 5-trimethylpyrrolidone, N-vinyl-5-methyl-5-ethylpyrrolidone, N-vinyl-3, 4, 5-trimethyl-3-ethylpyrrolidone, N-vinyl-5-ethyl-2-pyrrolidone, N-vinyl-3-ethylpyrrolidone, N-vinyl-4, 5-dimethylpyrrolidone, N-vinyl-5, 5-dimethylpyrrolidone, N-vinyl-3, 5-trimethylpyrrolidone, N-vinyl-5-ethyl-5-pyrrolidone, N-vinyl-3, 5-trimethyl-3-ethylpyrrolidone, N-ethyl-5-methylpyrrolidone, N-vinyl-3, 5-trimethyl-5-ethylpyrrolidone, one or more of N-vinyl-2-piperidone, N-vinyl-3-methylpiperidone, N-vinyl-3-methylcaprolactam, N-vinyl-4-methylpiperidone, N-vinyl-4-methylcaprolactam, N-vinyl-4-methylpiperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3, 5-dimethyl-2-piperidone, N-vinyl-4, 4-dimethyl-2-piperidone, N-vinyl-2-caprolactam, N-vinyl-7-methylcaprolactam, N-vinyl-7-ethylcaprolactam, N-vinyl-3, 5-dimethylcaprolactam, N-vinyl-4, 6-dimethylcaprolactam, N-vinyl-3, 5, 7-trimethylcaprolactam, N-vinyl-2-valerolactam, N-vinylhexahydro-2-azetidinone, N-vinyloctahydro-2-azetidinone and N-vinyldecahydrodecan-2-azepinone.
In some embodiments, monomer VI has the general structural formula shown in formula VI:
in the formula VI, n is an integer between 1 and 6, s is an integer between 0 and 16, each R is the same or different and is independently selected from C 1 -C 20 Preferably selected from C 1 -C 10 More preferably selected from C 1 -C 6 Is a hydrocarbon group.
In some embodiments, in formula VI, n is 1, 2, 3, 4, 5, or 6.
In some embodiments, in formula VI, s is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16.
In some embodiments, each R is the same or different and is independently selected from C1-C6 alkyl, e.g., C1-C3 alkyl, C4-C6 alkyl.
In some embodiments, the silicone polymer does not include structural units derived from monomer VII, wherein monomer VII is selected from one or more of acrylamide, methacrylamide, N-ethylacrylamide, N-propylacrylamide, N-isopropylacrylamide, N-butylacrylamide, N-methylacrylamide, N-ethylmethacrylamide, N-propylmethacrylamide, N-isopropylmethacrylamide, N-dimethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-diisopropyl (meth) acrylamide, N-butylmethacrylamide, N- (meth) acryloylpyrrolidone, N- (meth) acryloylpiperidine, N- (meth) acryloylpyrrolidine, N- (meth) acryloylpiperidine, N- (meth) acryloylmorpholine, N- (meth) acryloylpiperazine, N- (meth) acryloylaziridine, N- (meth) acryloylazetidine, N- (meth) acryloylazepine, and N- (meth) azacyclooctane.
In some embodiments, the general structural formula of monomer VII is shown in formula VII:
CH 2 ＝C(R 1 )-C(O)-N(R 2 R 3 ) VII
in formula VII, R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl of R 1 Preferably selected from hydrogen atoms or methyl groups;
R 2 and R is 3 Each independently selected from hydrogen atoms or C 1 -C 20 Alkyl of R 2 And R is 3 Preferably selected from hydrogen atoms or C 1 -C 10 More preferably selected from hydrogen atoms or C 1 -C 6 Alkyl of (a);
or R is 2 And R is 3 Taken together with the nitrogen atom to which they are attached to form C 3 -C 8 Is preferably formed into pyrrolidone, piperidinyl, pyrrolidinyl, pyrrolyl, piperidoneA group, morpholinyl, piperazinyl, aziridinyl, azetidinyl, azepanyl or azepanyl group.
In some embodiments, in formula VII, R 1 Selected from hydrogen atoms or C 1 -C 10 Is a hydrocarbon group. In some embodiments, in formula VII, R 1 Selected from hydrogen atoms or C 1 -C 6 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Is a hydrocarbon group. In some embodiments, R 1 Preferably selected from hydrogen atoms or methyl groups.
In some embodiments, in formula VII, R 2 And R is 3 Each independently selected from hydrogen atoms or C 1 -C 10 Is a hydrocarbon group. In some embodiments, in formula VII, R 2 And R is 3 Each independently selected from hydrogen atoms or C 1 -C 6 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Is a hydrocarbon group.
In some embodiments, in formula VII, R 2 And R is 3 Taken together with the nitrogen atom to which they are attached to form an azacyclo C 3 -C 8 An alkyl group.
In some embodiments, in formula VII, R 2 And R is 3 Taken together with the nitrogen atom to which they are attached form pyrrolidone, piperidinyl, pyrrolidinyl, pyrrolyl, piperidonyl, morpholinyl, piperazinyl, aziridinyl, azetidinyl, azepanyl, or azacyclooctyl.
In some embodiments, the silicone polymer has a weight average molecular weight of 1000 to 300 ten thousand, for example 5000 to 250 ten thousand. The weight average molecular weight can be measured by gel chromatography (GPC).
In a second aspect, the present application provides a novel silicone polymer emulsion treatment that can impart excellent water and oil repellency to the surface of a fibrous fabric or impart excellent stain or graffiti resistance to a coating material, such that the fibrous fabric and coating material can be effectively resistant to water-based and oil-based stains.
In some embodiments, the treatment agent provided herein includes a silicone polymer, an emulsifier, and an aqueous medium, wherein the silicone polymer is the silicone polymer of the first aspect.
In other embodiments, the treatment agents provided herein include a silicone polymer, an emulsifier, and an aqueous medium, wherein the silicone polymer includes structural units derived from monomer I, monomer I including silicon monomer I-A and optional silicon monomer I-B,
a) The structural general formula of the silicon monomer I-A is shown in the formula I-A:
M-Z 1 or Z is 1 -M-Z 1
Formula I-A
Wherein M contains a polymerizable functional group;
Z 1 selected from the structures shown below:
Z 1 wherein R is 4 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 20 An alkylene group of 1.ltoreq.a.ltoreq.200;
Y 1 and Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Or of formula (1), and further satisfies Y when a is 1 1 And/or Y 2 Is of the formula (1), at least one Y when a is greater than 1 and less than or equal to 200 1 Is a structure of formula (1) and/or at least one Y 2 Is a structure of formula (1):
R 7 each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 20 The alkylene of (2) is more than or equal to 0 and less than or equal to 200;
b) The structural general formula of the silicon monomer I-B is shown in the formula I-B:
M-Z 2 or Z is 2 -M-Z 2
Formula I-B
Wherein M contains a polymerizable functional group;
Z 2 Selected from the group consisting of the structures shown in the following,
Z 2 wherein R is 3 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 4 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 20 Is not less than 1 and not more than 200.
The inventors of the present application have unexpectedly found that a polymer emulsion obtained by polymerizing the above monomer I and the optional monomer II has an excellent water repellent effect and simultaneously has an oil repellent effect, thereby imparting excellent oil and water repellent properties to a fibrous fabric and antifouling and anti-graffiti properties to a coating.
In some embodiments, the polymerizable functional group in M is selected from groups containing carbon-carbon double bonds.
In some embodiments, in formula I-A and/or formula I-B, M is as shown in formula I-1:
CH 2 ＝C(R 1 )-X-B-
I-1
in the formula I-1, R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl of (a); b is selected from C 1 -C 20 Alkylene group, C 6 -C 20 And combinations thereof,
x is selected from the group shown as X-1 and X-2,
-C(O)-O- X-1
-C(O)-N(R 2 )- X-2
R 2 selected from hydrogen atoms or C 1 -C 20 Is a hydrocarbon group.
In some embodiments, in formula I-1, R 1 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments, in formula I-1, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-1, B is C 6 -C 15 Arylene groups of (2), e.g. C 6 -C 9 Arylene of (C) 10 -C 12 Arylene or C of (2) 13 -C 15 Arylene group of (a).
In some embodiments, R in the groups represented by X-1 and X-2 2 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group.
In some embodiments, in formula I-1, R 1 Selected from a hydrogen atom or a methyl group; b is C 1 -C 6 An alkylene group of (a); x, R 2 Selected from hydrogen atoms or methyl groups.
In some embodiments, in formula I-A and/or formula I-B, M is as shown in formula I-2:
CH 2 ＝C(R 1 )-W-B- I-2
in the formula I-2, R 1 Selected from hydrogen atoms or C 1 -C 20 An alkyl group;
w is selected from the group shown in W-1, W-2, W-3 and W-4,
-O-C(O)-N(R 2 )- W-2
-O-C(O)-O- W-3
-O-C(O)-O-D-N(R 2 )- W-4
R 2 selected from hydrogen atoms or C 1 -C 20 Alkyl, D is C 1 -C 20 An alkylene group of (a); when W is selected from W-1, B is absent or C 1 -C 20 When W is selected from W-2, W-3,W-4, B is selected from C 1 -C 20 Alkylene group, C 6 -C 20 Arylene groups of (a) and combinations thereof.
In some embodiments, in formula I-2, R 1 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments In the formula I-2, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-2, R 2 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments, in formula I-2, D is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-2, R 1 And R is 2 Selected from hydrogen atoms or methyl groups, B and D being C 1 -C 6 Alkylene groups of (a).
In some embodiments, when W is selected from W-1, B is absent or C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, when W is selected from W-2, W-3,W-4, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, when W is selected from W-2, W-3,W-4, B is C 6 -C 15 Arylene groups of (2), e.g. C 6 -C 9 Arylene of (C) 10 -C 12 Arylene or C of (2) 13 -C 15 Arylene group of (a).
In some embodiments, in formula I-A and/or formula I-B, M is as shown in formula I-3:
in the formula I-3, R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl, B is independently selected from C 1 -C 20 Alkylene group, C 6 -C 20 Aryl groups of (a) and combinations thereof.
In some embodiments, in formula I-3, R 1 Selected from hydrogen atoms or C 1 -C 10 Alkyl groups of (2), e.g. C 1 -C 3 Alkyl, C of (2) 4 -C 6 Alkyl or C of (2) 8 -C 10 Is a hydrocarbon group. In some embodiments, in formula I-3, B is C 1 -C 10 Alkylene of (C) 1 -C 3 Alkylene group, C 4 -C 6 Alkylene or C of (2) 8 -C 10 Alkylene groups of (a).
In some embodiments, in formula I-3, B is C 6 -C 15 Arylene groups of (2), e.g. C 6 -C 9 Arylene of (C) 10 -C 12 Arylene or C of (2) 13 -C 15 Arylene group of (a).
In some embodiments, in formula I-3, R 1 Selected from hydrogen atoms or methyl groups.
In some embodiments, Z 1 Wherein R is 4 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 10 And/or 1.ltoreq.a.ltoreq.100, e.g.1.ltoreq.a.ltoreq.80; r is R 7 Each independently is C 1 -C 10 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl group(s),C 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 10 And/or 0.ltoreq.b.ltoreq.100, e.g.0.ltoreq.b.ltoreq.80.
In some embodiments, Z 1 Wherein R is 4 Each independently is C 1 -C 6 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R 5 -O-R 6 -a group, R 5 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 6 Is C 1 -C 6 An alkylene group of 1.ltoreq.a.ltoreq.30; r is R 7 Each independently is C 1 -C 6 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 6 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 10 Is C 1 -C 6 The alkylene group of (2) is more than or equal to 0 and less than or equal to 30.
In some embodiments, a is an integer from 1 to 80, an integer from 1 to 30, an integer from 1 to 20, or an integer from 1 to 10.
In some embodiments, b is 0. In some embodiments, b is an integer from 1 to 30, an integer from 1 to 20, an integer from 1 to 10, or an integer from 1 to 5.
Specifically indicated, R 4 ，R 8 Representative is C 1 -C 20 Alkyl of C 1 -C 20 Alkoxy, C 6 -C 20 Of the aryl radicals, in particular C 1 -C 8 Alkyl of C 1 -C 4 Alkoxy groups of (a). For example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, and the like. Aryl groups such as phenyl, tolyl, naphthyl, and the like. R is R 4 ，R 8 It is also possible to have such a structure (R 5 -O-R 6 )-，R 5 Is C 1 -C 10 Alkyl of R 6 Is C 1 -C 10 Alkylene groups of (2), more commonly such as CH 3 O(CH 2 ) x -and the like. R is R 6 Is a slave C 1 -C 20 Alkyl groups and C of (C) 6 -C 20 For example, an aryl group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, hexadecyl and the like, and an aryl group such as phenyl, tolyl, naphthyl and the like.
In some embodiments, Z 1 One or more selected from the following structures i-1 to i-4:
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, R is C 1 -C 3 For example methyl.
In some preferred embodiments, Z 1 Selected from the following structures:
one or more of the following;
me represents methyl, 1.ltoreq.m+1.ltoreq.60, preferably 1.ltoreq.m+1.ltoreq.30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, Z 2 Wherein R is 3 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 4 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 10 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 10 Alkylene groups of (a).
In some embodiments, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 100. In some embodiments, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 80. According to some embodiments of the present application, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 30. According to some embodiments of the present application, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 20. According to some embodiments of the present application, Z 2 In the formula, a is more than or equal to 1 and less than or equal to 10.
In some embodiments, Z 2 Wherein R is 3 Each independently is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 4 Each independently isC 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl of (C) 7 -C 10 Alkylaryl, C 1 -C 6 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 6 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 10 Aralkyl or C of (C) 7 -C 10 Alkylaryl group R of (2) 6 Is C 1 -C 10 Is not less than 1 and not more than 10.
In some embodiments, Z 2 One or more selected from the following structures ii-1 to ii-2:
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, Z 2 Selected from the following structures:
one or more of the following;
me represents methyl, ph represents phenyl; m+1 is less than or equal to 1 and less than or equal to 60, preferably m+1 is less than or equal to 1 and less than or equal to 30; x is more than or equal to 1 and less than or equal to 9, preferably x is more than or equal to 1 and less than or equal to 7.
In some embodiments, m is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.
In some embodiments, x is 1, 2, 3, 4, 5, 6, or 7.
In some embodiments, silicon monomer I-A is selected from
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝C(CH 3 )C(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-NH-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝CHC(O)-NH-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-CH 2 -Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(CH 3 )[O-[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ] 2 ，0≤n≤25；
CH 2 ＝CH-ph-Si(OSi(CH 3 ) 3 ) 3 (ph represents)；
CH 2 ＝CH-ph-(CH 2 ) 2 Si(OSi(CH 3 ) 3 ) 3 (ph represents)；
CH 2 ＝CH-O-C(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 2 -NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ] 2 ；
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ] 2 。
In some embodiments, silicon monomer I-B is selected from
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 8 H 17 ，1≤n≤25；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ，1≤n≤25；
CH 2 ＝CH-ph-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl, ph tableShowing the )，1≤n≤25；
CH 2 ＝CH-O-C(O)-NH-(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 2 -NH-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝C(CH 3 )-C(O)-N[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 represents butyl), n is more than or equal to 1 and less than or equal to 25.
In some embodiments, the silicone polymer further comprises structural units derived from monomer II,
CH 2 ＝C(R 1 )-P-R 3 II
in the formula II, P is selected from groups shown as P-1 and P-2,
-C(O)-O- P-1
-C(O)-N(R 2 )- P-2
R 1 and R is 2 Each independently is a hydrogen atom or C 1 -C 20 An alkyl group; r is R 3 Is C 1 -C 40 Alkyl, C 4 -C 30 Cyclic hydrocarbons or C 7 -C 20 Alkylaryl groups.
In some embodiments, in formula II, R 1 Is a hydrogen atom or C 1 -C 10 Alkyl radicals, preferably hydrogen atoms or C 1 -C 6 Alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or n-hexyl.
In some embodiments, in formula II, R 2 Hydrogen atom or C 1 -C 10 Alkyl radicals, preferably hydrogen atoms or C 1 -C 6 Alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or n-hexyl.
In some embodiments, in formula II, R 3 Selected from C 1 -C 30 Alkyl or C 4 -C 20 Cyclic hydrocarbon groups. In some embodiments, in formula II, R 3 Selected from C 1 -C 10 Alkyl, C 11 -C 20 Alkyl, C 20 -C 30 Alkyl, C 4 -C 10 Cycloalkyl, C 11 -C 20 Cycloalkane, C 31 -C 30 Cycloalkane, C 4 -C 10 Cycloalkenyl, C 11 -C 20 Cycloolefin, C 31 -C 30 Cycloolefin, C 7 -C 15 Alkylaryl groups.
In some embodiments, monomer II is selected from one or more of methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, dodecyl (meth) acrylate, myristyl (meth) acrylate, pentadecyl (meth) acrylate, cetyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate, eicosyl (meth) acrylate, heneicosyl (meth) acrylate, docosyl (meth) acrylate, hexacosyl (meth) acrylate, triacontyl (meth) acrylate, cyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, benzyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentadienyl (meth) acrylate, tricyclopentyl (meth) acrylate, adamantyl (meth) acrylate, 2-methyl-2-adamantyl (meth) acrylate, or 2-ethyl-2-adamantyl (meth) acrylate.
In some embodiments, the silicone polymer does not include structural units derived from monomer IV, wherein monomer IV is selected from one or more of dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, diethylaminoethyl (meth) acrylate, diethylaminopropyl (meth) acrylate, N-t-butylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylamide, diethylaminoethyl (meth) acrylamide, dipropylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, diethylaminopropyl (meth) acrylamide, or dipropylaminopropyl (meth) acrylamide.
In some embodiments, the structural formula of monomer IV is as shown in formula IV:
CH 2 ＝C(R 1 )-P-B-N(R 3 R 4 ) IV
in the formula IV, P is selected from groups shown as P-1 and P-2,
-C(O)-O- P-1
-C(O)-N(R 2 )- P-2
b is C 1 -C 20 An alkylene group of (a); r is R 1 And R is 2 Each independently is a hydrogen atom or C 1 -C 20 An alkyl group; r is R 3 And R is 4 Each independently is a hydrogen atom, C 1 -C 18 Alkyl, hydroxyethyl or benzyl, or R 3 And R is 4 And combine with the nitrogen atom to form morpholino, piperidino, or pyrrolidino.
In some embodiments, the proportion of structural units produced by silicon monomer I-a in the total amount of structural units produced by silicon monomer I-a to structural units produced by silicon monomer I-B is 1% to 100%,5% to 100%,10% to 100%, or 50% to 100%, e.g., 1%, 5%, 10%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, or any two of them, in mass percent. The total amount of structural units produced by silicon monomer I-A and structural units produced by silicon monomer I-B, i.e., the total amount of structural units produced by monomer I.
In some embodiments, monomer I produces structural units in a mass content of 30% to 100%. In some embodiments, monomer I produces structural units in a mass content of 40% to 85%. In some embodiments, monomer I produces structural units in a mass content of 50% to 80%. In some embodiments, monomer I produces structural units in a mass content of 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or a range of any two compositions thereof.
In some embodiments, monomer II produces structural units in a mass content of 5% to 70%. In some embodiments, monomer II produces structural units in a mass content of 10% to 70%. In some embodiments, monomer II produces structural units in a mass content of 15% to 50%. In some embodiments, monomer II produces structural units in a mass content of 20% to 45%. In some embodiments, monomer II produces structural units in a mass content of 5%, 7%, 10%, 20%, 25%, 35%, 40%, 45%, 50%, 55%, 60%, 65% or a range of any two compositions thereof.
In some embodiments, the silicone polymer further comprises structural units derived from a crosslinking monomer III, which is a compound having two reactive groups and/or an unsaturated carbon-carbon double bond (preferably a (meth) acrylate), and may also be a compound having at least 2 unsaturated carbon-carbon double bonds (preferably a (meth) acrylate), or a compound having at least one unsaturated carbon-carbon double bond and at least one reactive group, examples of which are preferably hydroxyl, epoxy, chloromethyl, blocked isocyanate, amino or carboxyl groups, and the like.
In some embodiments, crosslinking monomer III may be selected from one or more of diacetone (meth) acrylamide, N-methylol (meth) acrylamide, 3-chloro-2-hydroxypropyl (meth) acrylate, 2-acetoacetylethyl (meth) acrylate, glycidyl (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, or the 2-butanone oxime adduct of ethyl ester of 2-isocyanato (meth) acrylate.
In some embodiments, the silicone polymer has a weight average molecular weight of 1000 to 300 ten thousand, for example 5000 to 250 ten thousand. The weight average molecular weight can be measured by gel chromatography (GPC).
In some embodiments, the emulsifier is selected from one or more of a nonionic surfactant, an anionic surfactant, a cationic surfactant, and an amphoteric surfactant.
In some embodiments, the nonionic surfactant is selected from one or more of ethers, esters, ester ethers, alkanolamides, polyols, and amine oxide surfactants. In some embodiments, the nonionic surfactant is a nonionic surfactant having an oxyalkylene group.
In some embodiments, the nonionic surfactant may be one or more of alkylene oxide adducts of linear and/or branched aliphatic groups, polyalkylene glycol esters of linear and/or branched fatty acids, polyoxyethylene (POE)/polyoxypropylene (POP) copolymers (random or block copolymers), alkylene oxide adducts of acetylenic diols.
In some embodiments, the nonionic surfactant includes addition products of ethylene oxide with hexylphenol, isooctylphenol, cetyl alcohol, oleic acid, an alkyl (C12-C16) thiol, sorbitan mono fatty acid (C7-C9) or (C12-C18) amine, and the like.
In some embodiments, the cationic surfactant is selected from one or more of amines, amine salts, delegate amine salts, imidazolines, and imidazolinium salt surfactants.
In some embodiments, examples of cationic surfactants are those wherein R 1 、R 2 、R 3 And R is 4 Independently of one another, are identical or different hydrogen atoms or hydrocarbon radicals having 1 to 50 carbon atoms (e.g. C 1 -C 6 Alkyl, C 7 -C 10 Alkyl, C 11 -C 15 Alkyl or C 16 -C 20 Alkyl), an aryl group having 6 to 50 carbon atoms, an aralkyl group having 7 to 50 carbon atoms, or an alkylaryl group having 7 to 50 carbon atoms, and X is a halogen (for example, chlorine or bromine), an acid (for example, an inorganic acid such as hydrochloric acid, or an organic acid (particularly, a fatty acid) such as acetic acid).
In some embodiments, the cationic surfactant comprises one or more of dodecyl trimethyl ammonium acetate, tetradecyl trimethyl ammonium chloride, hexadecyl trimethyl ammonium bromide, and trimethyl octadecyl ammonium chloride.
In some embodiments, examples of anionic surfactants are fatty alcohol sulfates, such as sodium lauryl sulfate; alkyl sulfonates, such as sodium lauryl sulfonate; alkylbenzene sulfonates, such as sodium dodecylbenzene sulfonate; and fatty acid salts such as sodium stearate and the like. In some embodiments, the zwitterionic surfactant may be exemplified by alanines, imidazoline betaines, amidobetaines, acetic acid betaines, and the like, and specifically may be exemplified by lauryl betaine, stearyl betaine, lauryl carboxymethyl hydroxyethyl imidazoline betaine, lauryl dimethyl amino acetic acid betaine, fatty amidopropyl dimethyl amino acetic acid betaine, and the like.
In some embodiments, the emulsifiers are nonionic surfactants and cationic surfactants.
In some embodiments, the emulsifier is present in an amount of 0.1% to 20% by mass, such as 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18% or 19% by mass, based on the mass of the silicone polymer.
In some embodiments, the aqueous medium is preferably water. In some embodiments, the aqueous medium includes water and an organic solvent. The organic solvent is not particularly limited, and any organic solvent that can be mixed with water is suitable for use in the present application, and examples of the organic solvent include acetone, methyl ethyl ketone, ethyl acetate, ethanol, isopropyl alcohol, butyl diglycol, propylene glycol, dipropylene glycol, tripropylene glycol, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol dimethyl ether, propylene glycol monomethyl ether acetate, and the like. The ratio of water to the organic solvent is not particularly limited.
In a third aspect, the present application provides a method for preparing the treating agent according to the second aspect, which includes the steps of:
(1) Mixing water, a monomer (a monomer I, an optional monomer II), an emulsifier and an optional organic solvent to obtain a pre-emulsion;
(2) And adding an initiator and an optional molecular weight regulator into the pre-emulsion to carry out polymerization reaction to obtain the polymer emulsion.
In some embodiments, monomer I is used in an amount of from 30% to 100%, preferably from 40% to 85%, more preferably from 50% to 80%, such as 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or any two of these ranges of composition by mass of the total amount of monomers.
In some embodiments, monomer II is used in an amount of 5% to 70% by mass, preferably 10% to 70% by mass, more preferably 15% to 50% by mass, even more preferably 20% to 45% by mass, such as 5%, 10%, 20%, 25%, 35%, 40%, 45%, 50%, 55%, 60%, 65% by mass, or any two of these ranges.
In some embodiments, the amount of silicon monomer I-a is in a range of 1% to 100%,5% to 100%,10% to 100%,50% to 98%, such as 1%, 5%, 10%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, or any two of them, by mass, based on the total amount of silicon monomer I-a and silicon monomer I-B.
In some embodiments, the initiator is selected from one or more of peroxides, azo-based compounds, and persulfuric-based compounds. In some embodiments, the initiator is selected from water-soluble initiators.
In some embodiments, the water soluble initiator is selected from one or more of 2,2 '-azobisisobutylaminidine dihydrochloride, 2' -azobis (2-methylpropionamidine) hydrochloride, 2 '-azobis [2- (2-imidazolin-2-yl) propane ] sulfate hydrate, 2' -azobis [2- (5-methyl-imidazolin-2-yl) propane ] hydrochloride, potassium persulfate, barium persulfate, ammonium persulfate, hydrogen peroxide, and t-butyl hydroperoxide.
In some embodiments, the initiator is preferably a water-soluble azo compound having a half-life of 10 hours and a decomposition temperature of 40 ℃ or higher, such as 2,2' -azobisisobutylamidine dihydrochloride, and the like.
In some embodiments, the initiator is present in an amount of 0.1% to 5% by mass, e.g., 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4% or 4.5% by mass, based on the mass of the monomer.
In some embodiments, the molecular weight regulator is selected from the group consisting of mercapto compounds, such as 2-mercaptopropionic acid, 2-mercaptoethanol, alkyl mercaptans, or mercaptopropionic acid.
In some embodiments, the molecular weight regulator is present in an amount of 0.01% to 10% by mass, e.g., 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9% by mass, based on the mass of the monomer.
In some embodiments, the polymerization reaction temperature is 40 ℃ to 90 ℃. In some embodiments, the polymerization reaction is for a period of time ranging from 4 hours to 20 hours.
In some embodiments, the emulsion polymerization process typical of the present application is as follows,
mixing water, a monomer, an emulsifying agent and an organic solvent, emulsifying the monomer at a high speed, introducing nitrogen for replacement, adding an initiator, an optional molecular weight regulator and an optional organic solvent, heating to a reaction temperature of 40-90 ℃ for 4-20 hours, and obtaining the product.
In a fourth aspect, the present application provides the use of the silicone polymer of the first aspect or the treatment of the second aspect or the treatment prepared by the method of the third aspect in a fibrous web or coating.
In a fifth aspect, the present application provides a water-and oil-repellent fibrous web comprising a fibrous web and the silicone polymer of the first aspect or the treating agent of the second aspect or the treating agent prepared by the method of the third aspect.
The present application also provides an antifouling or anti-graffiti coating comprising the coating and the silicone polymer of the first aspect or the treating agent of the second aspect or the treating agent prepared by the method of the third aspect.
In some embodiments, the silicone polymer of the first aspect or the treating agent of the second aspect or the treating agent prepared by the method of the third aspect is attached to the surface and/or the interior of the fibrous web or coating.
In a sixth aspect, the present application provides a method of treating a fibrous web comprising contacting the fibrous web with the silicone polymer of the first aspect or the treating agent of the second aspect or the treating agent prepared by the method of the third aspect.
The present application also provides a method of treating a coating comprising contacting the coating with the silicone polymer of the first aspect or the treating agent of the second aspect or the treating agent prepared by the method of the third aspect.
In some embodiments, the contacting is achieved by a surface sizing process, a surface coating process, a wet end addition process, or a soaking treatment process.
The treating agent of the present application can be applied to an object to be treated by a conventionally known method. In general, the treatment agent is diluted in an organic solvent or water, and is applied to the surface of the object to be treated by a known method such as dip coating, spray coating, or foam, followed by drying. In addition, vulcanization may be applied with a suitable crosslinking agent (e.g., blocked isocyanate) if desired. Insect repellent, softener, antibacterial agent, flame retardant, antistatic agent, crease-resist agent, etc. may be added to the treatment agent of the present application. The concentration of the polymer in the treatment liquid in contact with the substrate may be 0.01 to 10% by weight (particularly in the case of dip coating), for example 0.05 to 10% by weight.
In the present application, various examples of the fiber fabric are given. Examples include: animal or plant natural fibers such as cotton, hemp, wool, silk and the like, synthetic fibers such as polyamide, polyester, polyvinyl alcohol, polyacrylonitrile, polyvinyl chloride, polypropylene and the like, semisynthetic fibers such as rayon, acetate and the like, inorganic fibers such as glass fibers, carbon fibers, asbestos fibers and the like, or mixed fiber fabrics thereof.
ADVANTAGEOUS EFFECTS OF INVENTION
The organosilicon polymer or the treating agent is applied to the treatment of the fiber fabric or the paint, and can endow the surface of the fiber fabric with oil and water repellency and the antifouling or anti-graffiti performance of the paint after the treatment.
The specific embodiment is as follows:
in order to make the objects, technical solutions and advantages of the present application more apparent, the present application will be further described in detail with reference to the following examples. These examples are only for the purpose of explaining the present application and are not intended to constitute any limitation to the present application. The actual scope of the application is set forth in the following claims.
Unless otherwise indicated herein, the terms used herein have their ordinary meanings as known to those skilled in the art.
In this application, the term "alkyl" refers to a straight chain alkyl or branched alkyl group, non-limiting examples of which include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-ethylpropyl, 2-methylbutyl, 3-methylbutyl, 2-dimethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, and the like.
In the present application, the term "alkylene" refers to a straight chain alkylene groupAlkyl or branched alkylene groups, non-limiting examples of which include: methylene, ethylene, n-propylene, n-butylene, n-pentylene, -CHCH 3 CH 2 -、-CHCH 3 CH 2 CH 2 -、CH 2 CH 3 CHCH 2 -and the like.
In the present application, "%" means mass percent unless otherwise specified.
1. Polymerization process
A typical emulsion polymerization process of the present application is as follows,
mixing water, monomer, emulsifier and organic solvent, shearing, emulsifying and homogenizing the monomer at high speed, introducing nitrogen for replacement, adding initiator and optional molecular weight regulator, heating to 40-90 deg.C, and reacting for 4-20 hr.
The process for producing the treating agent of the present application comprises the following steps:
(1) Homogenizing and mixing water, a monomer, an emulsifier and an optional organic solvent to obtain a pre-emulsion;
(2) And adding an initiator and an optional molecular weight regulator into the pre-emulsion to carry out polymerization reaction to obtain the polymer emulsion.
2. Test method
Treatment of fibrous fabrics
The fabrics treated in this example were dyed 100% polyester cloth and 100% kaki fabric. The treatment method comprises the following steps: the cloth sample was placed to contain a certain concentration of the treating agent (polymer emulsion) of the present application to carry out impregnation treatment (material absorption rate of 70%), and then dried at 110 ℃ for 90 seconds and baked at 170 ℃ for 60 seconds to obtain a cloth sample. The sample cloth was evaluated for water repellency, and oil repellency.
Evaluation method
Method for testing water repellency of fiber fabrics
According to the Teflon global specification and quality control test method, the samples are tested by using liquids with different isopropanol volume contents, and the degree of surface wetting is observed and determined. This test provides a rough index of resistance to water staining. The higher the repellency rating, the better the resistance of the final substrate to water-based materials, the composition of the standard test liquids is shown in table 1 below,
table 1 Water resistance test grade composition
| Water resistance rating | Composition by volume, isopropanol | Make up volume percent, water |
| 1 | 2 | 98 |
| 2 | 5 | 95 |
| 3 | 10 | 90 |
| 4 | 20 | 80 |
| 5 | 30 | 70 |
| 6 | 40 | 60 |
| 7 | 50 | 50 |
| 8 | 60 | 40 |
| 9 | 70 | 30 |
| 10 | 80 | 20 |
| 11 | 90 | 10 |
| 12 | 100 | 0 |
Method for testing fiber fabrics-spray water repellency test
The dynamic water resistance of the treated substrates was measured according to the American textile dyeing chemical Association (AATCC) TM-22, reference being made to published standards. A glass funnel having a volume of at least 250mL and a nozzle capable of ejecting 250mL of water in 20-30 seconds was used. The test piece frame was a metal frame having a diameter of 15 cm. 3 test pieces having a size of about 20 cm. Times.20 cm were prepared, and the pieces were fixed to a test piece holder frame so that the pieces were free from wrinkles. The center of the spray was centered on the sheet, room temperature water (250 mL) was added to the glass funnel and the test sheet (25 seconds to 30 seconds) was sprayed. The holding frame is removed from the table, one end of the frame is grasped, the underside of the front face is brought into contact with the opposite end with a hard object. The same procedure was repeated while the rotation was maintained at 180 ° again, so that the excessive water droplets were dropped. Wet test pieces were given scores of 0, 50, 70, 80, 90, 100 in the order of starting poor water repellency (as shown in table 2 below). Comparison was made with a wet comparison standard. The results were obtained from the average of 3 determinations.
Table 2 Water repellency rating table
| Water repellency No. | Status of |
| 100 | The surface is free from wetting or adhesion of water drops |
| 90 | The surface is not moist but exhibits the adhesion of small water droplets |
| 80 | The surface presents a small, individual drop-like wetting |
| 70 | Half of the surface is moist and assumes the state of a small, individually moist, permeable cloth |
| 50 | The surface as a whole is moist |
| 0 | The surface and the back are integrally wet |
Method for testing oil resistance of fiber fabrics
The oil repellency was evaluated according to the test method of AATCC-TM118, the basic principle being to apply test oil drops of different surface tension to the test cloth, the higher the rating, the better the oil repellency, the composition of the standard test liquid being shown in Table 3 below.
Table 3 fabric oil repellency test grade composition
| Oil repellency rating | Test solution | Surface tension mN/m |
| 8 | N-heptane | 20.0 |
| 7 | N-octane | 21.8 |
| 6 | N-decane | 23.5 |
| 5 | N-dodecane | 25.0 |
| 4 | N-tetradecane | 26.7 |
| 3 | N-hexadecane | 27.3 |
| 2 | 65 parts of liquid paraffin and 35 parts of n-hexadecane | 29.6 |
| 1 | Liquid paraffin | 31.2 |
3. Examples and comparative examples
The abbreviations for chemicals are shown in table 4.
Table 4 codes and chemical formulas of the respective substances
Example 1
Into a four-necked flask equipped with a reflux condenser, a nitrogen inlet, a thermometer and a stirrer, 490 g of deionized water, 135 g of Si-B3 monomer, 33 g of dipropylene glycol methyl ether, 6 g of polyoxyethylene isotridecyl ether (EO: 18, number of ethylene oxide units: 18), 1.5 g of polyoxyethylene isotridecyl ether (EO: 3, number of ethylene oxide units: 3) and 60 g of octadecyl trimethyl ammonium chloride (10% solution) were charged. Dispersing by ultrasonic emulsification at 60 ℃ for 30 minutes under stirring. After nitrogen substitution in the reaction flask, a solution of 1.2 g of 2,2' -azobis (2-amidinopropane) dihydrochloride and 20 g of water was added. Heating to 60 ℃, reacting for 10 hours to obtain polymer emulsion, and regulating the solid content to 20% by using deionized water. Comparison of the theoretical solids content with the measured solids content shows a monomer conversion of greater than 98%.
Examples 2 to 7
As in example 1, but replacing Si-B3 with a monomer I of a different structure, respectively, si-NB3 (example 2), si-ph-B3 (example 3), si-OCN-B3 (example 4), si-OCO-B3 (example 5), si-B2 (example 6), si-N2-B2 (example 7).
The polymer emulsion was subjected to a fiber fabric test: respectively selecting 100% polyester cloth and 100% cotton cloth, diluting the obtained polymer emulsion into 5%,3% and 2% (polymer emulsion content) liquid with tap water, padding, drying at 110deg.C for 90 s, and baking at 170deg.C for 60 s. The sample cloth was evaluated for water repellency, and oil repellency. The water repellency, water repellency and oil repellency were measured separately and the results are shown in Table 5.
Table 5 performance test table
Example 8
Into a four-necked flask equipped with a reflux condenser, a nitrogen inlet, a thermometer and a stirrer, 490 g of deionized water, 100 g of Si-B3 monomer, 35 g of Si-5 (average molecular weight: 500) monomer, 33 g of dipropylene glycol methyl ether, 6 g of polyoxyethylene isotridecyl ether (EO: 18, number of oxyethylene units: 18), 1.5 g of polyoxyethylene isotridecyl ether (EO: 3, number of oxyethylene units: 3), and 60 g of octadecyl trimethyl ammonium chloride (10% solution) were charged. Dispersing by ultrasonic emulsification at 60 ℃ for 30 minutes under stirring. After nitrogen substitution in the reaction flask, a solution of 1.2 g of 2,2' -azobis (2-amidinopropane) dihydrochloride and 20 g of water was added. Heating to 60 ℃, reacting for 10 hours to obtain polymer emulsion, and regulating the solid content to 20% by using deionized water. Comparison of the theoretical solids content with the measured solids content shows a monomer conversion of greater than 98%.
Example 9
Into a four-necked flask equipped with a reflux condenser, a nitrogen inlet, a thermometer and a stirrer, 490 g of deionized water, 100 g of Si-B3 monomer, 35 g of StA monomer, 33 g of dipropylene glycol methyl ether, 6 g of polyoxyethylene isotridecyl ether (EO: 18, number of ethylene oxide units: 18), 1.5 g of polyoxyethylene isotridecyl ether (EO: 3, number of ethylene oxide units: 3) and 60 g of octadecyl trimethyl ammonium chloride (10% solution) were charged. Dispersing by ultrasonic emulsification at 60 ℃ for 30 minutes under stirring. After nitrogen substitution in the reaction flask, a solution of 1.2 g of 2,2' -azobis (2-amidinopropane) dihydrochloride and 20 g of water was added. Heating to 60 ℃, reacting for 10 hours to obtain polymer emulsion, and regulating the solid content to 20% by using deionized water. Comparison of the theoretical solids content with the measured solids content shows a monomer conversion of greater than 98%.
Performance tests were conducted according to the test methods of examples 1 to 7, and the results are shown in Table 6.
Table 6 performance test table
Comparative example 1
Into a four-necked flask equipped with a reflux condenser, a nitrogen inlet, a thermometer and a stirrer were charged 135 g of Si-B3 monomer, 45 g of DN,15 g of HEMA and 195 g of methyl ethyl ketone. Nitrogen is introduced for 30 minutes, the temperature is slowly raised to 50-60 ℃, 2.5 g of peroxide initiator tert-butyl peroxypivalate is added in portions, the reaction temperature is controlled at 60 ℃ for 20 hours, and about 390 g of polymer A solution with the solid content of about 50% is obtained.
560 g of water and 18 g of glacial acetic acid are added, the mixture is stirred at 70℃for more than 1 hour, MEK in the solution of the polymer A is distilled off under reduced pressure, and the solids are adjusted to 25% aqueous solution with deionized water.
Comparative example 2
Into a four-necked flask equipped with a reflux condenser, a nitrogen inlet, a thermometer and a stirrer, 490 g of deionized water, 135 g of StA monomer, 33 g of dipropylene glycol methyl ether, 6 g of polyoxyethylene isotridecyl ether (EO: 18, number of ethylene oxide units: 18), 1.5 g of polyoxyethylene isotridecyl ether (EO: 3, number of ethylene oxide units: 3) and 60 g of octadecyl trimethyl ammonium chloride (10% solution) were charged. Dispersing by ultrasonic emulsification at 60 ℃ for 30 minutes under stirring. After nitrogen substitution in the reaction flask, a solution of 1.2 g of 2,2' -azobis (2-amidinopropane) dihydrochloride and 20 g of water was added. Heating to 60 ℃, reacting for 10 hours to obtain polymer emulsion, and regulating the solid content to 20% by using deionized water. Comparison of the theoretical solids content with the measured solids content shows a monomer conversion of greater than 98%.
Comparative example 3
135 g of amino silicone oil (ammonia value 0.5mmol/g, viscosity 1200cp (25 ℃) and 9 g of isomeric tridecanol polyoxyethylene ether (EO number: 9), 9 g of isomeric tridecanol polyoxyethylene ether (EO number: 5) are added into a 1 liter plastic cup, stirred at high speed, 610 g of deionized water is slowly added (30 minutes are added), stirred at high speed for 5 minutes after the addition is completed, and stirred at low speed for 5 minutes again, so that stable silicone oil emulsion with the effective content of 20% is obtained.
Performance tests were performed according to the test methods of examples 1 to 7, and the results are shown in table 7.
Table 7 performance test table
The solids content of example 1, comparative example 2 and comparative example 3 were 20% and the solids content of comparative example 1 was 25%, but the contents of silicon monomer or silicon compound (or long-chain hydrocarbon monomer) in these four examples were substantially uniform.
The polymer emulsions obtained in examples 1-9 of the present application all showed good oil and water repellency when applied to a fibrous web, as summarized in Table 5, table 6, and Table 7.
Comparative example 1 uses the same silicon monomer I as example 1, but because of the solution polymerization, and the product finally needs to be dissolved in water, more water-soluble monomer is introduced into the structure to assist dissolution, and finally the treating agent of the structure has better oil-repellent performance, but the water-repellent performance is obviously insufficient compared with the application.
Comparative example 2 uses a long chain alkyl monomer as the main reactant, and the result shows that the treating agent has certain water repellency but no oil repellency in the fiber fabric. Comparative example 3 uses a long-chain silicone oil as a raw material, and as a result, the treatment agent also shows that the treatment agent has a certain water repellency but does not have oil repellency in a fiber fabric.
The technical solution of the present application is not limited to the above specific embodiments, and all technical modifications made according to the technical solution of the present application fall within the protection scope of the present application.
Claims (14)
1. A treatment agent comprising a silicone polymer, an emulsifier, and an aqueous medium, wherein the silicone polymer comprises structural units derived from monomer I comprising silicon monomer I-A and optionally silicon monomer I-B,
a) The structural general formula of the silicon monomer I-A is shown in the formula I-A:
M-Z 1 or Z is 1 -M-Z 1
Formula I-A
Wherein M contains a polymerizable functional group;
Z 1 selected from the structures shown below:
Z 1 wherein R is 4 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (a)Or C 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 20 An alkylene group of 1.ltoreq.a.ltoreq.200;
Y 1 and Y 2 Identical or different, each independently selected from C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Or of formula (1), and further satisfies Y when a is 1 1 And/or Y 2 Is of the formula (1), at least one Y when a is greater than 1 and less than or equal to 200 1 Is a structure of formula (1) and/or at least one Y 2 Is a structure of formula (1):
R 7 each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 20 The alkylene of (2) is more than or equal to 0 and less than or equal to 200;
b) The structural general formula of the silicon monomer I-B is shown in the formula I-B:
M-Z 2 or Z is 2 -M-Z 2
Formula I-B
Wherein M contains a polymerizable functional group;
Z 2 selected from the group consisting of the structures shown in the following,
Z 2 wherein R is 3 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 4 Each independently is C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl of (C) 7 -C 12 Alkylaryl, C 1 -C 20 Alkoxy or R of (A) 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 20 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 20 Is not less than 1 and not more than 200.
2. The treatment agent according to claim 1, wherein,
m is shown as a formula I-1:
CH 2 ＝C(R 1 )-X-B-
I-1
in the formula I-1, R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl of (a); b is selected from C 1 -C 20 Alkylene group, C 6 -C 20 Arylene groups of (a) and combinations thereof;
x is selected from the group shown as X-1 and X-2,
-C(O)-O-
X-1
-C(O)-N(R 2 )-
X-2
R 2 selected from hydrogen atoms or C 1 -C 20 Alkyl of (a);
and/or
M is shown as a formula I-2:
CH 2 ＝C(R 1 )-W-B-
I-2
in the formula I-2, R 1 Selected from hydrogen atoms or C 1 -C 20 An alkyl group;
w is selected from the group shown in W-1, W-2, W-3 and W-4,
-O-C(O)-O-D-N(R 2 )- W-4
R 2 selected from hydrogen atoms or C 1 -C 20 Alkyl, D is C 1 -C 20 An alkylene group of (a); when W is selected from W-1, B is absent or C 1 -C 20 When W is selected from W-2, W-3,W-4, B is selected from C 1 -C 20 Alkylene group, C 6 -C 20 Arylene groups of (a) and combinations thereof;
and/or
M is shown as a formula I-3:
in the formula I-3, R 1 Selected from hydrogen atoms or C 1 -C 20 Alkyl, B is independently selected from C 1 -C 20 Alkylene group, C 6 -C 20 Arylene groups of (a) and combinations thereof.
3. The treatment agent according to claim 1 or 2, wherein the silicone polymer further comprises structural units derived from monomer II,
CH 2 ＝C(R 1 )-C(O)-O-R 3 II
R 1 is a hydrogen atom or C 1 -C 20 An alkyl group; r is R 3 Is C 1 -C 40 Alkyl, C 4 -C 30 Cyclic hydrocarbon radicals or C 7 -C 20 Alkylaryl groups.
4. A treatment agent according to any one of claims 1 to 3, wherein the silicone polymer does not comprise structural units derived from monomer IV, wherein monomer IV is selected from one or more of dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, diethylaminoethyl (meth) acrylate, diethylaminopropyl (meth) acrylate, N-t-butylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylamide, diethylaminoethyl (meth) acrylamide, dipropylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, diethylaminopropyl (meth) acrylamide or dipropylaminopropyl (meth) acrylamide,
Preferably, the structural general formula of the monomer IV is shown in formula IV:
CH 2 ＝C(R 1 )-P-B-N(R 3 R 4 ) IV
in the formula IV, P is selected from groups shown as P-1 and P-2,
-C(O)-O-
P-1
-C(O)-N(R 2 )-
P-2
b is C 1 -C 20 An alkylene group of (a); r is R 1 And R is 2 Each independently is a hydrogen atom or C 1 -C 20 An alkyl group; r is R 3 And R is 4 Each independently is a hydrogen atom, C 1 -C 18 Alkyl, hydroxyethyl or benzyl, or R 3 And R is 4 And combine with the nitrogen atom to form morpholino, piperidino, or pyrrolidino.
5. The treatment agent according to any one of claims 1 to 4, wherein the emulsifier is selected from one or more of nonionic surfactant, anionic surfactant, cationic surfactant and amphoteric surfactant; and/or
The aqueous medium comprises water and optionally an organic solvent.
6. The treating agent according to any one of claims 1 to 5, wherein the proportion of the structural units produced by the silicon monomer I-a in the total amount of the structural units produced by the silicon monomer I-a and the structural units produced by the silicon monomer I-B is 1% to 100%,5% to 100%,10% to 100% or 50% to 100% in mass percent; and/or
The mass content of the structural units generated by the monomer I in the organosilicon polymer is 30-100%, preferably 40-85%, more preferably 50-80%; and/or
The mass content of the structural units produced by the monomer II in the organosilicon polymer is 5% -70%, preferably 10% -70%, more preferably 15% -50%, and still more preferably 20% -45%.
7. The treatment agent according to any one of claims 1 to 6, wherein R in the silicon monomers I-A and I-B 1 Selected from hydrogen atoms or methyl groups, B being C 1 -C 10 Alkylene of (C), preferably B is C 1 -C 6 An alkylene group of (a);
silicon monomers I-A and I-B, X, R 2 Selected from a hydrogen atom or a methyl group;
in the silicon monomer I-A, Z 1 Wherein R is 4 Each independently is C 1 -C 10 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Or R 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 10 An alkylene group of 1.ltoreq.a.ltoreq.80; r is R 7 Each independently is C 1 -C 10 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a); r is R 8 Each independently is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Or R 9 -O-R 10 -a group wherein R 9 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl of (a)Or C 7 -C 12 Alkylaryl group R of (2) 10 Is C 1 -C 10 Alkylene of 0.ltoreq.b.ltoreq.80;
in the silicon monomer I-B, Z 2 Wherein R is 3 Each independently is C 1 -C 10 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 4 Each independently is C 1 -C 10 Alkyl of C 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Or R 5 -O-R 6 -a group, R 5 Is C 1 -C 10 Alkyl, C of (2) 6 -C 10 Aryl, C of (2) 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl group R of (2) 6 Is C 1 -C 10 An alkylene group of (a); a is more than or equal to 1 and less than or equal to 80; and/or
In monomer II, R 1 Selected from a hydrogen atom or a methyl group; r is R 3 Selected from C 1 -C 30 Alkyl, C 4 -C 20 Cyclic hydrocarbon radicals or C 7 -C 15 Alkylaryl groups.
8. The treatment agent according to any one of claims 1 to 7, wherein Z 1 One or more selected from the following structures i-1 to i-4:
Z 1 preferably selected from
One or more of the following;
Z 2 one or more selected from the following structures ii-1 to ii-2:
Z 2 preferably selected from:
one or more of the following;
r is each independently selected from C 1 -C 10 Alkyl, C 6 -C 10 Aryl, C 7 -C 12 Aralkyl or C of (C) 7 -C 12 Alkylaryl groups of (a);
me represents methyl, ph represents phenyl, 1.ltoreq.m+1.ltoreq.60, preferably 1.ltoreq.m+1.ltoreq.30; p is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; q is more than or equal to 0 and less than or equal to 60, preferably more than or equal to 0 and less than or equal to 30; x is not less than 1 and not more than 9, preferably not less than 1 and not more than 7, and each x can be the same or different.
9. The treatment agent according to any one of claims 1 to 8, wherein the silicon monomer I-a is selected from
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝C(CH 3 )C(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-NH-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝CHC(O)-NH-(CH 2 ) 3 Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
CH 2 ＝CHC(O)-O-(CH 2 ) 3 Si(OSi(CH 2 CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-CH 2 -Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 Si(CH 3 )[O-[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 ] 2 ，0≤n≤25；
CH 2 ＝CH-ph-Si(OSi(CH 3 ) 3 ) 3 (ph represents)；
CH 2 ＝CH-ph-(CH 2 ) 2 Si(OSi(CH 3 ) 3 ) 3 (ph represents)；
CH 2 ＝CH-O-C(O)-NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 2 -NH-(CH 2 ) 3 Si(OSi(CH 3 ) 3 ) 3 ；
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -Si(OSi(CH 3 ) 3 ) 3 ] 2 ；
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -Si(CH 3 )(OSi(CH 3 ) 3 ) 2 ] 2 The method comprises the steps of carrying out a first treatment on the surface of the And/or
Silicon monomer I-B is selected from
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 8 H 17 ，1≤n≤25；
CH 2 ＝C(CH 3 )C(O)-O-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ，1≤n≤25；
CH 2 ＝CH-ph-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl, ph represents
)，1≤n≤25；
CH 2 ＝CH-O-C(O)-NH-(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 3 -[Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 Indicating a butyl pieceBase), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝CH-O-C(O)-O-(CH 2 ) 2 -NH-(CH 2 ) 3 [Si(CH 3 ) 2 O]n-Si(CH 3 ) 2 C 4 H 9 (C 4 H 9 represents butyl), 1
≤n≤25；
CH 2 ＝CH-C(O)-N[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 Represents butyl), n is more than or equal to 1 and less than or equal to 25;
CH 2 ＝C(CH 3 )-C(O)-N[-(CH 2 ) 3 -(Si(CH 3 ) 2 O) n -Si(CH 3 ) 2 C 4 H 9 ] 2 (C 4 H 9 represents butyl), 1.ltoreq.n.ltoreq.n
25, a step of selecting a specific type of material; and/or
Monomer II is selected from one or more of methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, dodecyl (meth) acrylate, myristyl (meth) acrylate, pentadecyl (meth) acrylate, cetyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate, eicosyl (meth) acrylate, heneicosyl (meth) acrylate, behenyl (meth) acrylate, hexacosyl (meth) acrylate, triacontyl (meth) acrylate, cyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, benzyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentyl (meth) acrylate, tricyclopentyl (meth) acrylate, adamantyl (meth) acrylate, 2-methyl-2-adamantyl (meth) acrylate, or 2-ethyl-2-adamantyl (meth) acrylate.
10. A process for preparing the treatment agent of any one of claims 1 to 9, comprising the steps of:
(1) Mixing water, a monomer, an emulsifier and an optional organic solvent to obtain a pre-emulsion;
(2) And adding an initiator and an optional molecular weight regulator into the pre-emulsion to carry out polymerization reaction to obtain the polymer emulsion.
11. Use of a treatment according to any one of claims 1 to 9 or a treatment prepared by a method according to claim 10 in a fibrous web or coating.
12. A water-repellent and oil-repellent fiber fabric comprising a fiber fabric and the treating agent according to any one of claims 1 to 9 or the treating agent produced by the method according to claim 10,
preferably, the treatment agent according to any one of claims 1 to 9 or the treatment agent prepared by the method according to claim 10 is attached to the surface and/or the interior of the fibrous web.
13. A method for treating a fibrous web, comprising contacting the fibrous web with the treating agent of any one of claims 1 to 9 or the treating agent prepared by the method of claim 10,
preferably, the contacting is achieved by a surface sizing process, a surface coating process, a wet end addition process, or a soaking treatment process.
14. An antifouling or anti-graffiti coating comprising the coating and a treatment according to any one of claims 1 to 9 or a treatment prepared by the process of claim 10,
preferably, the treatment agent according to any one of claims 1 to 9 or the treatment agent prepared by the method according to claim 10 is attached to the surface and/or the interior of the coating.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310988989.0A CN117265875A (en) | 2023-08-07 | 2023-08-07 | Treating agent and fiber fabric or coating |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310988989.0A CN117265875A (en) | 2023-08-07 | 2023-08-07 | Treating agent and fiber fabric or coating |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117265875A true CN117265875A (en) | 2023-12-22 |
Family
ID=89207126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310988989.0A Pending CN117265875A (en) | 2023-08-07 | 2023-08-07 | Treating agent and fiber fabric or coating |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117265875A (en) |
-
2023
- 2023-08-07 CN CN202310988989.0A patent/CN117265875A/en active Pending
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