CN115135637A - 聚氨酯化合物 - Google Patents
聚氨酯化合物 Download PDFInfo
- Publication number
- CN115135637A CN115135637A CN202180016271.4A CN202180016271A CN115135637A CN 115135637 A CN115135637 A CN 115135637A CN 202180016271 A CN202180016271 A CN 202180016271A CN 115135637 A CN115135637 A CN 115135637A
- Authority
- CN
- China
- Prior art keywords
- compound
- polyurethane
- diisocyanate
- alcohol
- agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 79
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 79
- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 20
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 17
- 239000012948 isocyanate Substances 0.000 claims abstract description 12
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 11
- 150000001298 alcohols Chemical class 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 64
- -1 alcohol compound Chemical class 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 239000005056 polyisocyanate Substances 0.000 claims description 22
- 229920001228 polyisocyanate Polymers 0.000 claims description 22
- 229920005862 polyol Polymers 0.000 claims description 21
- 150000003077 polyols Chemical class 0.000 claims description 21
- 239000006185 dispersion Substances 0.000 claims description 17
- 239000002981 blocking agent Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000004381 surface treatment Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 13
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 9
- 238000012986 modification Methods 0.000 claims description 8
- 230000004048 modification Effects 0.000 claims description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000004417 polycarbonate Substances 0.000 claims description 6
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 235000013877 carbamide Nutrition 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 150000003217 pyrazoles Chemical class 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 18
- 239000004744 fabric Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000000835 fiber Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000000123 paper Substances 0.000 description 12
- 239000012756 surface treatment agent Substances 0.000 description 12
- 239000005871 repellent Substances 0.000 description 11
- 239000004811 fluoropolymer Substances 0.000 description 9
- 229920002313 fluoropolymer Polymers 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 239000010985 leather Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000013043 chemical agent Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 241000219146 Gossypium Species 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000002940 repellent Effects 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- NODLZCJDRXTSJO-UHFFFAOYSA-N 1,3-dimethylpyrazole Chemical compound CC=1C=CN(C)N=1 NODLZCJDRXTSJO-UHFFFAOYSA-N 0.000 description 2
- SZQCPPRPWDXLMM-UHFFFAOYSA-N 1,4-dimethylpyrazole Chemical compound CC=1C=NN(C)C=1 SZQCPPRPWDXLMM-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- VQTVFIMEENGCJA-UHFFFAOYSA-N 3,4-dimethyl-1H-pyrazole Chemical compound CC=1C=NNC=1C VQTVFIMEENGCJA-UHFFFAOYSA-N 0.000 description 2
- OFQCJVVJRNPSET-UHFFFAOYSA-N 3,5-dimethyl-4-nitro-1h-pyrazole Chemical compound CC1=NNC(C)=C1[N+]([O-])=O OFQCJVVJRNPSET-UHFFFAOYSA-N 0.000 description 2
- RISOHYOEPYWKOB-UHFFFAOYSA-N 4-bromo-3,5-dimethyl-1h-pyrazole Chemical compound CC1=NNC(C)=C1Br RISOHYOEPYWKOB-UHFFFAOYSA-N 0.000 description 2
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- NFKGQHYUYGYHIS-UHFFFAOYSA-N dibutyl propanedioate Chemical compound CCCCOC(=O)CC(=O)OCCCC NFKGQHYUYGYHIS-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- LWIWFCDNJNZEKB-UHFFFAOYSA-N dipropyl propanedioate Chemical compound CCCOC(=O)CC(=O)OCCC LWIWFCDNJNZEKB-UHFFFAOYSA-N 0.000 description 2
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
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- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
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- MCRZWYDXIGCFKO-UHFFFAOYSA-N 2-butylpropanedioic acid Chemical compound CCCCC(C(O)=O)C(O)=O MCRZWYDXIGCFKO-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- ABMULKFGWTYIIK-UHFFFAOYSA-N 2-hexylphenol Chemical class CCCCCCC1=CC=CC=C1O ABMULKFGWTYIIK-UHFFFAOYSA-N 0.000 description 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- GVLZCADFQWZNQM-UHFFFAOYSA-N 2-methyl-3,4-dipropylphenol Chemical compound CCCC1=CC=C(O)C(C)=C1CCC GVLZCADFQWZNQM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
本发明提供聚氨酯化合物,其能够获得提供高拨水拨油性的交联剂。该聚氨酯化合物(A)由异氰酸酯(A1)和式:HO-Z(Y-R)n[式中,R分别独立地为-O-、-NH-、-O-C(=O)-、-NH-C(=O)-、-C(=O)-NH-、-O-C(=O)-NH-、-NH-C(=O)-O-、-NH-C(=O)-NH-、-NH-S(=O)2-、-S(=O)2-NH-、-NH-(CH2)m-NH-S(=O)2-或-NH-(CH2)m-S(=O)2-NH-等(其中,m为1~5的整数),Z为直接键合、或者2价或3价的碳原子数1~5的烃基,n为1或2]所示的长链醇(A2)形成。
Description
技术领域
本发明涉及聚氨酯化合物、以及含有聚氨酯化合物的水性聚氨酯组合物。
背景技术
在含氟排斥剂和非氟排斥剂等排斥剂中,需求高性能。作为用于辅助拨水性的添加剂,可以列举交联剂。主要的交联剂有异氰酸酯系交联剂,例如封端剂具有特征的异氰酸酯交联剂。
专利文献1(国际公开2006/038466号公报)公开了一种以特定化学式所示的多异氰酸酯为必须成分的水分散型聚氨酯组合物。
专利文献2(日本专利公开2014-210882号公报)公开了一种封端多异氰酸酯组合物,其具有多异氰酸酯单元、作为单末端羟基的聚环氧乙烷单元和封端剂单元、并且脲基甲酸酯基/异氰脲酸酯基的数量比率为30/100~200/100。
现有技术文献
专利文献
专利文献1:国际公开2006/038466号公报
专利文献2:日本专利公开2014-210882号公报
发明内容
发明要解决的技术问题
利用现有的交联剂未必能够充分地辅助拨水拨油性,需求更高性能的辅助洗涤耐久性的交联剂。
用于解决技术问题的技术手段
本发明提供一种由具有碳原子数7~40的烃基的长链醇形成的聚氨酯化合物。
本发明的优选的方式如下。
方式1:
一种聚氨酯化合物(A),包含由异氰酸酯(A1)和式:HO-Z(Y-R)n所示的长链醇(A2)形成的单元。
[式中,R分别独立地为碳原子数7~40的烃基,
Y分别独立地为-O-、-NH-、-NH-C(=O)-、-C(=O)-NH-、-NH-C(=O)-O-、-NH-C(=O)-NH-、-C6H4-、-NH-(CH2)m-NH-、-NH-(CH2)m-O-、-O-C(=O)-、-C(=O)-O-、-NH-(CH2)m-O-C(=O)-、-NH-(CH2)m-C(=O)-O-、-O-C(=O)-NH-、-O-C6H4-、-NH-S(=O)2-、-S(=O)2-NH-、-NH-(CH2)m-O-C(=O)-NH-、-NH-(CH2)m-NH-C(=O)-O-、-NH-(CH2)m-C(=O)-NH-、-NH-(CH2)m-NH-C(=O)-、-NH-(CH2)m-NH-C(=O)-NH-、-NH-(CH2)m-O-C6H4-、-NH-(CH2)m-NH-C6H4-、-NH-(CH2)m-NH-S(=O)2-或-NH-(CH2)m-S(=O)2-NH-(其中,m为1~5的整数),
Z为直接键合、或者2价或3价的碳原子数1~5的烃基,
n为1或2。]
方式2:
如方式1所述的聚氨酯化合物,其中,还包含由选自封端剂(A3)和醇化合物(A4)中的至少1种形成的单元。
方式3:
如方式1或2所述的聚氨酯化合物,其中,异氰酸酯(A1)为选自甲苯二异氰酸酯(TDI)、二苯甲烷二异氰酸酯(MDI)、MDI低聚物、萘-1,5-二异氰酸酯、苯二甲基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、4,4-二环己基甲烷二异氰酸酯、降冰片烷二异氰酸酯、异佛尔酮二异氰酸酯(IPDI)、二异氰酸酯的加成物、脲基甲酸酯改性物、缩二脲改性物、异氰脲酸酯改性物或碳二亚胺改性物和聚氨酯预聚物中的至少1种。
方式4:
如方式1~3中任一项所述的聚氨酯化合物,其中,
长链醇(A2)为选自下式中的至少1种:
HO-(CH2)m-NH-C(=O)-R、
HO-(CH2)m-C(=O)-NH-R、
HO-(CH2)m-O-C(=O)-R、
HO-(CH2)m-C(=O)-O-R、
HO-(CH2)m-NH-C(=O)-O-R、
HO-(CH2)m-O-C(=O)-NH-R、
HO-(CH2)m-NH-C(=O)-NH-R、
HO-(CH2)m-NH-S(=O)2-R、和
HO-(CH2)m-S(=O)2-NH-R。
[式中,R为碳原子数12~30的烃基,
m为1~5的整数]。
方式5:
如方式2~4中任一项所述的聚氨酯化合物,其中,封端剂(A3)为选自肟、酚、醇、硫醇、酰胺、酰亚胺、咪唑、尿素、胺、亚胺、吡唑和活性亚甲基化合物中的至少1种。
方式6:
如方式2~5中任一项所述的聚氨酯化合物,其中,
醇化合物(A4)为单醇(mono-ol)或多元醇,
单醇是C2或C3环氧烷与碳原子数1~10的起始一元醇(mono alcohol)加成而成的化合物,
多元醇是二元醇和具有3个以上羟基的多元醇,为选自低分子多元醇、聚醚多元醇、聚酯多元醇、聚酯聚碳酸酯多元醇、结晶性或非晶性的聚碳酸酯多元醇中的至少1种。
方式7:
一种聚氨酯混合物,其含有方式1~6中任一项所述的聚氨酯化合物、以及选自多异氰酸酯(A1)、长链醇(A2)、封端剂(A3)和醇化合物(A4)中的至少1种。
方式8:
一种水性聚氨酯组合物,其含有:方式1~6中任一项所述的聚氨酯化合物(A);和水(B)。
方式9:
如方式8所述的水性聚氨酯组合物,其中,水性聚氨酯组合物是水分散体。
方式10:
如方式8或9所述的水性聚氨酯组合物,其中,水性聚氨酯组合物是交联剂或辅助剂。
方式11:
一种方式8~10中任一项所述的水性聚氨酯组合物的制造方法,其中,将异氰酸酯(A1)和长链醇(A2)在有机溶剂中混合并使其反应,再与水混合。
方式12:
一种基材的处理方法,其包括:利用含有方式1~6中任一项所述的聚氨酯化合物的表面处理组合物对基材进行处理的步骤。
方式13:
一种经过处理的纤维制品,其中,方式1~6中任一项所述的聚氨酯化合物以交联物的形态附着于被处理物。
发明效果
根据本发明,能够获得作为提高拨水拨油剂等表面处理剂性能的辅助剂发挥作用的聚氨酯化合物。聚氨酯化合物辅助表面处理剂提供高拨水拨油性。根据聚氨酯化合物,能够获得高洗涤耐久性,特别是能够提供对于拨水性的高洗涤耐久性。
具体实施方式
本发明涉及含有聚氨酯化合物(A)和水(B)的水性聚氨酯组合物。
聚氨酯化合物(A)由多异氰酸酯(A1)和式:HO-Z(Y-R)n所示的长链醇(A2)形成。
[式中,R分别独立地为碳原子数7~40的烃基,
Y分别独立地为-O-、-NH-、-NH-C(=O)-、-C(=O)-NH-、-NH-C(=O)-O-、-NH-C(=O)-NH-、-C6H4-、-NH-(CH2)m-NH-、-NH-(CH2)m-O-、-O-C(=O)-、-C(=O)-O-、-NH-(CH2)m-O-C(=O)-、-NH-(CH2)m-C(=O)-O-、-O-C(=O)-NH-、-O-C6H4-、-NH-S(=O)2-、-S(=O)2-NH-、-NH-(CH2)m-O-C(=O)-NH-、-NH-(CH2)m-NH-C(=O)-O-、-NH-(CH2)m-C(=O)-NH-、-NH-(CH2)m-NH-C(=O)-、-NH-(CH2)m-NH-C(=O)-NH-、-NH-(CH2)m-O-C6H4-、-NH-(CH2)m-NH-C6H4-、-NH-(CH2)m-NH-S(=O)2-、或-NH-(CH2)m-S(=O)2-NH-(其中,m为1~5的整数),
Z为直接键合、或者2价或3价的碳原子数1~5的烃基,
n为1或2。]
即,聚氨酯化合物(A)具有由多异氰酸酯(A1)形成的单元、和由长链醇(A2)形成的单元。
聚氨酯化合物(A)可以进一步具有由选自封端剂(A3)和醇化合物(A4)中的至少1种形成的单元。聚氨酯化合物(A)优选具有由封端剂(A3)形成的单元和由醇化合物(A4)形成的单元双方。
聚氨酯化合物(A)可以由如下成分形成。
成分(A1)+成分(A2)
成分(A1)+成分(A2)+成分(A3)
成分(A1)+成分(A2)+成分(A4)
或者成分(A1)+成分(A2)+成分(A3)+成分(A4)
在本发明中,多异氰酸酯(A1)、长链醇(A2)、封端剂(A3)和醇化合物(A4)的任意种可以至少部分未反应。因此,本发明提供含有选自多异氰酸酯(A1)、长链醇(A2)、封端剂(A3)和醇化合物(A4)中的至少1种、以及聚氨酯化合物(A)的聚氨酯混合物。
多异氰酸酯(A1)的例子有甲苯二异氰酸酯(TDI)、二苯甲烷二异氰酸酯(MDI)、MDI低聚物、萘-1,5-二异氰酸酯、苯二甲基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、4,4-二环己基甲烷二异氰酸酯、降冰片烷二异氰酸酯、异佛尔酮二异氰酸酯(IPDI)、二异氰酸酯的加成物、脲基甲酸酯改性物、缩二脲改性物、异氰脲酸酯改性物或碳二亚胺改性物、和聚氨酯预聚物。
多异氰酸酯(A1)优选为二异氰酸酯。多异氰酸酯(A1)优选为下式所示的化合物。
O=C=N-R0-N=C=O
[式中,R0为2价的有机基团。]
R0是由多异氰酸酯除去异氰酸酯基后的基团。R0例如可以是碳原子数为3~30、例如为4~20或5~15的烃基。
在长链醇(A2)中,R优选为直链或支链的烃基。烃基特别地可以为直链的烃基。烃基优选为脂肪族烃基,特别优选为饱和的脂肪族烃基,特别优选为烷基。烃基的碳原子数优选为12~30,更优选为16~22。
在长链醇(A2)中,Y可以为-O-、-NH-、-NH-C(=O)-、-C(=O)-NH-、-NH-C(=O)-O-、-NH-C(=O)-NH-、-C6H4-、-NH-(CH2)m-NH-、-NH-(CH2)m-O-、-O-C(=O)-、-C(=O)-O-、-NH-(CH2)m-O-C(=O)-、-NH-(CH2)m-C(=O)-O-、-O-C(=O)-NH-、-O-C6H4-、-NH-S(=O)2-、-S(=O)2-NH-、-NH-(CH2)m-O-C(=O)-NH-、-NH-(CH2)m-NH-C(=O)-O-、-NH-(CH2)m-C(=O)-NH-、-NH-(CH2)m-NH-C(=O)-、-NH-(CH2)m-NH-C(=O)-NH-、-NH-(CH2)m-O-C6H4-、-NH-(CH2)m-NH-C6H4-、-NH-(CH2)m-NH-S(=O)2-、或-NH-(CH2)m-S(=O)2-NH-。
[式中,m为1~5,特别是2或4。]
Y优选为-O-、-NH-、-O-C(=O)-、-NH-C(=O)-、-C(=O)-NH-、-O-C(=O)-NH-、-NH-C(=O)-O-、-NH-C(=O)-NH-、-NH-S(=O)2-、-S(=O)2-NH-、-NH-(CH2)m-NH-S(=O)2-、或-NH-(CH2)m-S(=O)2-NH-。
[式中,m为1~5的整数,特别是2或4。]
Y更优选为-NH-C(=O)-、-C(=O)-NH-。
在长链醇(A2)中,Z为直接键合、或者2价或3价的碳原子数1~5的烃基,可以具有直链结构,也可以具有分支结构。Z的碳原子数优选为2~4,特别优选为2。Z的具体例有:直接键合、-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、具有分支结构的-CH2CH=、具有分支结构的-CH2(CH-)CH2-、具有分支结构的-CH2CH2CH=、具有分支结构的-CH2CH2CH2CH2CH=、具有分支结构的-CH2CH2(CH-)CH2-、具有分支结构的-CH2CH2CH2CH=。Z优选为-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-。
Z优选不是直接键合。
长链醇(A2)的优选的具体例如下。
HO-(CH2)m-NH-C(=O)-R
HO-(CH2)m-C(=O)-NH-R
HO-(CH2)m-O-C(=O)-R
HO-(CH2)m-C(=O)-O-R
HO-(CH2)m-NH-C(=O)-O-R
HO-(CH2)m-O-C(=O)-NH-R
HO-(CH2)m-NH-C(=O)-NH-R
HO-(CH2)m-NH-S(=O)2-R
HO-(CH2)m-S(=O)2-NH-R
[式中,R为碳原子数7~40的烃基,
m为1~5的整数。]
封端剂(A3)是掩蔽多异氰酸酯的异氰酸酯基、从而抑制异氰酸酯基的反应的化合物。作为封端剂(A3)的示例,可以列举肟、酚、醇、硫醇、酰胺、酰亚胺、咪唑、尿素、胺、亚胺、吡唑和活性亚甲基化合物。封端剂(A3)的其他示例,可以列举吡啶酚(pyridinol)、硫酚、双酮和酯。封端后的多异氰酸酯(封端异氰酸酯化合物)可以利用具有亲水性基团的化合物进行改性。作为封端剂(A3),肟、吡唑和活性亚甲基化合物因拨水性和拨油性提高而优选。
通过存在封端剂,拨水性的洗涤耐久性提高。
作为肟的示例,可以列举氨基甲肟、乙醛肟、丙酮肟、甲乙酮肟和环己酮肟。
作为酚的示例,可以列举根据情况可以具有至少1个(优选1个或2个)C1-10烷基的酚。作为酚的具体例,可以列举:苯酚;单烷基苯酚(例如甲酚、乙基苯酚、丙基苯酚、丁基苯酚、己基苯酚、2-乙基己基苯酚和辛基苯酚);以及二烷基苯酚(例如二乙基苯酚、二丙基苯酚、二丙基甲酚、二丁基苯酚、二-2-乙基己基苯酚、二辛基苯酚和二壬基苯酚)。
酚的追加的具体例,可以列举经苯乙烯化的苯酚、羟基苯甲酸酯。
作为醇的示例,可以列举具有C1-C30烷基的(优选一元的)醇(特别是烷醇)。
作为醇的具体例,可以列举甲醇、乙醇、丙醇、1-丁醇、仲丁醇、2-乙基-1-己醇、2-甲氧基乙醇、2-丁氧基乙醇、2-甲氧基-1-丙醇和3-甲基-2-戊烯-4-炔-1-醇。
作为硫醇的具体例,可以列举丁硫醇和十二烷基硫醇。
作为酰胺(优选酸性酰胺)的具体例,可以列举乙酰苯胺、乙酰胺、β-丙内酰胺、γ-丁内酰胺、δ-戊内酰胺、ε-己内酰胺、月桂内酰胺、硬脂内酰胺、N-甲基-ε-己内酰胺和吡咯烷酮。
作为酰亚胺的具体例,可以列举马来酰亚胺和琥珀酰亚胺等酸酰亚胺。
作为咪唑的具体例,可以列举咪唑和2-甲基咪唑。
作为尿素的具体例,可以列举尿素、硫脲和亚乙基脲。
作为胺的具体例,可以列举二苯胺、苯胺、咔唑、二乙胺、二丙胺和丙乙胺。
作为亚胺的具体例,可以列举亚乙基亚胺和聚乙烯亚胺。
作为吡唑的具体例,可以列举2-甲基吡唑、3-甲基吡唑、4-甲基吡唑、2,4-二甲基吡唑、2,5-二甲基吡唑、3,4-二甲基吡唑、3,5-二甲基吡唑、4-硝基-3,5-二甲基吡唑、4-溴-3,5-二甲基吡唑。
作为活性亚甲基化合物的示例,可以列举丙二酸酯(例如C1-30-烷基的丙二酸酯)、乙酰乙酸酯(例如C1-30-烷基乙酰乙酸酯)和乙酰丙酮。
用于形成封端异氰酸酯化合物的封端剂优选为吡唑化合物或丙二酸酯化合物,特别优选吡唑化合物。
吡唑化合物可以为下式所示的化合物。
[式中,各个R11相同或不同,为烷基、烯基、芳烷基、N-取代氨基甲酰基、苯基、NO2、卤原子或-C(=O)OR12基(R12为碳原子数1~4的烷基),
n为0、1、2或3。]
作为吡唑化合物的具体例,可以列举2-甲基吡唑、3-甲基吡唑、4-甲基吡唑、2,4-二甲基吡唑、2,5-二甲基吡唑、3,4-二甲基吡唑、3,5-二甲基吡唑、4-硝基-3,5-二甲基吡唑、4-溴-3,5-二甲基吡唑。
丙二酸酯化合物是丙二酸与醇(例如一元醇)的反应生成物(单酯或二酯(优选二酯))。通常,醇具有与羟基键合的具有1~30个碳原子的烃基。烃基优选为烷基,特别优选为具有1~4个碳原子的烷基。
作为丙二酸酯的具体例,可以列举丙二酸二甲酯、丙二酸二乙酯、丙二酸二丙酯、丙二酸二丁酯、丙二酸甲酯、丙二酸乙酯、丙二酸丙酯和丙二酸丁酯。优选二酯。作为丙二酸酯的优选的具体例,可以列举丙二酸二甲酯、丙二酸二乙酯、丙二酸二丙酯和丙二酸二丁酯。
醇化合物(A4)可以为单醇或多元醇。
单醇优选为C2或C3环氧烷与碳原子数1~10的起始一元醇(甲醇等)加成而成的化合物。
多元醇可以为二元醇以及具有3个以上羟基的多元醇。多元醇可以是低分子多元醇、聚醚多元醇、聚酯多元醇、聚酯聚碳酸酯多元醇、或者结晶性或非晶性的聚碳酸酯多元醇。
醇化合物(A4)优选除了具有羟基之外,还具有亲水基。亲水基不会因氨基甲酸酯反应而被消耗。亲水基的示例有C2或C3环氧烷基、氨基等。
聚氨酯化合物的分子量因交联而增加,因而醇化合物(A4)可以仅由单醇构成。
聚氨酯化合物优选具有源自多异氰酸酯(A1)的R0基、源自长链醇(A2)的-Z(Y-R)n基,还具有源自封端剂(A3)的基团、源自醇化合物(A4)的基团。
关于长链醇(A2)和醇化合物(A4)的合计量,可以为异氰酸酯指标[多异氰酸酯中的异氰酸酯基相对于醇中的活泼氢基的当量比]达到2~0.5、优选1.5~0.8、特别是1.2~0.9的量。长链醇(A2)与醇化合物(A4)的摩尔比可以为10﹕90~100﹕0、10﹕90~90﹕10、例如20﹕80~80﹕20、特别是30﹕70~70﹕30。
封端剂(A3)的量(当量比)相对于多异氰酸酯中的异氰酸酯基的当量可以为1~50当量%、例如2~30当量%、特别是3~20当量%。
水性聚氨酯组合物含有聚氨酯化合物(A)和水(B)。关于水(B)的量,可以为聚氨酯化合物(A)的量相对于水性聚氨酯组合物达到0.1~70重量%、例如1~50重量%的量。水性聚氨酯组合物也可以含有有机溶剂,有机溶剂的量相对于水(B)100重量份可以为200重量份以下、例如1~50重量份。
水性聚氨酯组合物优选为水分散体。水性聚氨酯组合物优选为自乳化型。水性聚氨酯组合物可以含有(相对于聚氨酯化合物(A)100重量份为0.1~10重量份的量的)乳化剂,但优选不含乳化剂。
聚氨酯化合物(A)可以通过使长链醇(A2)、和根据需要的醇化合物(A4)与多异氰酸酯(A1)反应、并根据需要使封端剂(A3)反应来制造。
水性聚氨酯组合物可以通过将多异氰酸酯(A1)和长链醇(A2)在有机溶剂中混合并使其反应,再添加水来制造。或者,水性聚氨酯组合物也可以通过将多异氰酸酯(A1)、长链醇(A2)和醇化合物(A4)在有机溶剂中混合并使其反应、再使封端剂(A3)反应、接着添加水来制造。在添加水之后,可以将有机溶剂除去。
使长链醇(A2)和醇化合物(A4)与多异氰酸酯(A1)反应的温度和时间可以为0~60℃、1分钟~24小时。使封端剂(A3)反应的温度和时间可以为30~120℃、1分钟~24小时。
聚氨酯化合物(A)(和水性聚氨酯组合物)能够作为交联剂或辅助剂发挥作用。“辅助剂”是指辅助表面处理剂的性能的药剂(提高拨水拨油性、防污性、去污性、剥离性和/或脱模性的药剂,特别是提高拨水拨油性的药剂)、对被处理物进行改性的药剂(特别是对纤维制品进行改性的药剂、例如提高纤维制品手感的药剂)、或者在表面处理剂处理时辅助稳定的加工的药剂。
通过将水性聚氨酯组合物与表面处理剂混合,能够得到表面处理组合物。
与聚氨酯化合物(A)混合的表面处理剂为任意物质均可,可以为氟系、硅系、聚氨酯系、丙烯酸系等。表面处理剂可以为溶液、乳液(特别是水性分散液)或气溶胶的形态,但优选为水性分散液。表面处理剂的有效成分的示例有含氟聚合物、含硅聚合物、聚氨酯、非氟非硅聚合物等。在表面处理组合物中,聚氨酯化合物(A)的量相对于表面处理剂的有效成分100重量份可以为1~100重量份、特别是5~50重量份。
表面处理组合物能够作为拨水剂、拨油剂、防污剂、去污剂、剥离剂和脱模剂使用。
表面处理组合物能够通过现有已知的方法应用于被处理物。通常采用如下方法:将该处理剂分散于水(和/或有机溶剂)中进行稀释,通过浸渍涂布、喷雾涂布、泡沫涂布等已知的方法,使其附着于被处理物的表面,并进行干燥。优选进行熟化(curing)。熟化的温度可以为60~250℃、特别是100~200℃,熟化的时间可以为1秒钟~10分钟、特别是10秒钟~3分钟。还可以在表面处理组合物中添加并用防虫剂、柔软剂、抗菌剂、阻燃剂、抗静电剂、定涂剂、防皱剂等。与基材接触的处理液中的聚氨酯含氟聚合物的浓度可以为0.01~10重量%(特别是在浸渍涂布时)、例如0.05~10重量%。
作为利用表面处理组合物(例如拨水拨油剂)进行处理的被处理物,可以列举纤维制品、石材、过滤器(例如静电过滤器)、防尘罩、燃料电池的部件(例如气体扩散电极和气体扩散支撑体)、玻璃、纸、木、皮革、毛皮、石棉、砖、水泥、金属和氧化物、陶瓷制品、塑料、涂面和灰泥(plaster)等。作为纤维制品,可以列举各种示例。例如可以列举棉、麻、羊毛、丝绸等动植物性天然纤维、聚酰胺、聚酯、聚乙烯醇、聚丙烯腈、聚氯乙烯、聚丙烯等合成纤维、人造丝(rayon)、醋酸纤维等半合成纤维、玻璃纤维、碳纤维、石棉纤维等无机纤维、或者它们的混合纤维。
纤维制品为纤维、布等任意形态均可。
表面处理组合物能够对基材的表面赋予所希望的剥离性。因此,能够容易地将基材的表面从其他表面(该基材的其他表面、或者其他基材的表面)剥离。
应用表面处理组合物的基材的示例有纤维制品(例如无纺布和织布)、纸、石材、皮革、树脂、玻璃、金属等。基材优选为布或纸。
表面处理组合物能够用于同样基材(例如布与布、纸与纸)之间的剥离、或者不同基材(例如布与树脂、布与金属、纸与布、纸与玻璃)之间的剥离。表面处理组合物能够用于粘接片材、粘接胶带的粘接面的保护材料、脱模膜、脱模纸、便签纸的制造等。
表面处理组合物还能够用作内部脱模剂或外部脱模剂。
含氟聚合物能够通过已知的用于利用液体对纤维制品进行处理的任意方法应用于纤维状基材(例如纤维制品等)。在纤维制品为布时,可以将布浸渍在溶液中,或者使溶液附着于布或者向布喷雾溶液。对于经过处理的纤维制品,为了表现拨油性,可以进行干燥,优选例如以100℃~200℃进行加热。
或者含氟聚合物可以通过清洗法应用于纤维制品,例如可以为洗涤应用或者在干式清洗法等应用于纤维制品。
被处理的纤维制品典型地为布,其包括织物、编物和无纺布、服装形态的布和地毯,也可以为纤维、丝或中间纤维制品(例如棉条(sliver)或粗丝等)。纤维制品材料可以为天然纤维(例如棉或羊毛等)、化学纤维(例如粘胶人造丝(viscose rayon)或莱赛尔等)、或合成纤维(例如聚酯、聚酰胺或丙烯酸纤维等),或者也可以为纤维的混合物(例如天然纤维和合成纤维的混合物等)。本发明的含氟聚合物在使纤维素系纤维(例如棉或人造丝等)具有疏油性和拨油性方面特别有效。另外,本发明的方法通常使纤维制品具有疏水性和拨水性。
或者纤维状基材也可以为皮革。为了使皮革具有疏水性和疏油性,可以在皮革加工的各个阶段、例如皮革的湿润加工期间中或者皮革的精加工期间中,将含氟聚合物从水溶液或水性乳化物应用于皮革。
或者纤维状基材还可以为纸。可以将含氟聚合物应用于预先形成的纸,或者也可以在制纸的各个阶段、例如在纸的干燥期间中应用。
“处理”意指通过浸漬、喷雾、涂布等将处理剂(表面处理组合物)应用于被处理物。通过处理,作为处理剂有效成分的聚合物浸透被处理物的内部、并且/或者附着于被处理物的表面。
聚氨酯化合物的交联物(表面处理剂的有效成分与聚氨酯化合物的反应产物)附着于被处理物。
实施例
下面,列举实施例和比较例具体地说明本发明,但这些说明并不限定本发明。
以下,只要没有特别说明,份、%或比表示重量份、重量%或重量比。
以下所使用的试验方法如下。
喷淋拨水性试验
依照AATCC试验法22-2010进行喷淋拨水性试验。
使用体积至少为250ml的玻璃漏斗和能够在20秒~30秒内喷雾250ml水的喷嘴。试验片支架是直径为15cm的金属支架。准备3片尺寸为约20cm×20cm的试验片,将片材固定在试验片保持支架上,使片材没有皱褶。将喷雾的中心置于片材的中心。向玻璃漏斗内注入室温的水(250mL),并向试验片喷雾(持续25秒~30秒的时间)。将保持支架从台座上取下,抓住保持支架的一端使得前方表面朝下,并用硬物轻轻击打相反侧的一端。再将保持支架旋转180°,重复同样的步骤使过剩的水滴掉落。将湿润的试验片与湿润对照标准物比较,按照拨水性从差到好的顺序评级为0、50、70、80、90和100分(拨水性No.)。由三次测定的平均值获得结果。数字后的标记“+”表示评价比该数字高,标记“-”表示评价比该数字低。
拨油性试验
按照AATCC试验法118-1992进行拨油性试验。
将经过处理的试验布在温度21℃、湿度65%的恒温恒湿器中保存4小时以上。试验液也使用在温度21℃保存过的试验液。试验在温度21℃、湿度65%的恒温恒湿室中进行。在试验布上静静地滴加试验液0.05ml,放置30秒钟后,如果液滴残留在试验布上,则评价为通过(pass)该试验液。拨油性设为所通过的试验液的最高分数,按照从拨油性差到好的水平,评价为不合格、1、2、3、4、5、6、7和8这九个等级。数字后的标记“+”表示评价比该数字高,标记“-”表示评价比该数字低。
拨油性试验液
拨水拨油性的洗涤耐久性
按照JIS L-0217-103法,反复洗涤5次、10次或15次,评价之后的拨水拨油性(HL5、HL10或HL15)。HL0是未进行洗涤的初始的拨水拨油性。
合成例1
在300mL烧瓶中加入1,6-六亚甲基二异氰酸酯的脲酸酯体(NCO含量21.8%)32.5g和二丙二醇二甲醚30g、硬脂酰胺乙醇4.85g,在氮气气氛中在搅拌下将内部温度从室温升至85℃,加入二月桂酸二丁基锡0.020g,搅拌2小时。之后,加入聚乙二醇单甲醚(分子量1000)5g,搅拌3小时,再加入二甲基吡唑14.3g,搅拌2小时。利用IR确认NCO基消失,冷却至室温。冷却后,在强力搅拌下添加40℃的水,搅拌10分钟,制造固态成分为20%的水分散体。
比较合成例1
在300mL烧瓶中加入二苯基二异氰酸酯(NCO含量21.8%)32.5g和二丙二醇二甲醚30g,在氮气气氛中在搅拌下将内部温度从室温升至85℃,加入二月桂酸二丁基锡0.020g,搅拌2小时。之后,加入聚乙二醇单甲醚(分子量1000)5g,搅拌3小时,再加入甲酮肟14.3g,搅拌2小时。利用IR确认NCO基消失,冷却至室温。冷却后,在强力搅拌下添加40℃的水,搅拌10分钟,制造固态成分为20%的水分散体。
比较合成例2
在300mL烧瓶中加入1,6-六亚甲基二异氰酸酯的脲酸酯体(NCO含量21.8%)32.5g和二丙二醇二甲醚30g、硬脂醇4.05g,在氮气气氛中在搅拌下将内部温度从室温升至85℃,加入二月桂酸二丁基锡0.020g,搅拌2小时。之后,加入聚乙二醇单甲醚(分子量1000)5g,搅拌3小时,再加入二甲基吡唑14.3g,搅拌2小时。利用IR确认NCO基消失,冷却至室温。冷却后,在强力搅拌下添加40℃的水,搅拌10分钟,制造固态成分为20%的水分散体。
合成例2
在1000mL高压釜中加入CF3CF2-(CF2CF2)n-CH2CH2OCOC(Cl)=CH2(n=2.0)(13FClA)65.1g、CF3CF2-(CF2CF2)n-CH2CH2OCOCH=CH2(n=2.0)(13FA)65.1g、丙烯酸硬脂酯30.9g、纯水400g、水溶性二醇系溶剂56g、烷基二甲基氯化铵1.56g、聚氧亚乙基烷基醚16.1g,在搅拌下利用超声波以60℃进行15分钟的乳化分散。对烧瓶内进行氮置换后,压入填充氯乙烯(VCM)61.2g,添加含偶氮基的水溶性引发剂0.4g,以60℃反应20小时,得到含氟聚合物的水性分散液(含氟拨水拨油剂)。聚合物的组成与入料单体的组成基本一致。
合成例3
在500mL高压釜中加入丙烯酸硬脂酯=45g、甲基丙烯酸异冰片酯=5g、纯水=145g、三丙二醇=15g、山梨糖醇酐单油酸酯=1.5g、聚氧亚乙基(EO:18)仲烷基(C12-14)醚=2g、二(十八烷基)二甲基氯化铵=1.5g,在搅拌下利用超声波以60℃进行15分钟的乳化分散。对高压釜内进行氮置换后,添加2,2-偶氮双(2-脒基丙烷)2盐酸盐=0.5g,以60℃反应3小时,得到非氟聚合物的水性分散液。再利用纯水将固态成分浓度调整为30%。生成聚合物的单体组成与单体入料组成基本一致。
实施例1
将合成例2中得到的含氟拨水拨油剂(以具有C6全氟烷基的含氟丙烯酸聚合物为有效成分的拨水拨油剂)用水稀释成4%,添加合成例1中得到的水分散体使其达到1%,均匀搅拌。将10片尼龙织布(500mm×200mm)、棉布(500mm×200mm)连续地浸渍于该试验液中,通入轧布机,利用针式拉幅机以170℃处理1分钟。之后,对尼龙织布和棉布的各布料,进行喷淋拨水性试验、拨油性试验及其洗涤耐久性试验。将结果示于表A。
比较例1和2
代替合成例1中得到的水分散体,使用比较合成例1(比较例1)或比较合成例2(比较例2)中得到的水分散体,除此以外,重复进行与实施例1同样的步骤。将结果示于表A。
实施例2
代替合成例2中得到的含氟聚合物的水分散体,使用合成例3中得到的非氟聚合物的水分散体,除此以外,重复进行与实施例1同样的步骤。将结果示于表A。
比较例3和4
代替合成例1中得到的水分散体,使用比较合成例1(比较例3)或比较合成例2(比较例4)中得到的水分散体,除此以外,重复进行与实施例2同样的步骤。将结果示于表A。
产业上的可利用性
本发明的聚氨酯组合物能够作为交联剂或辅助剂使用。本发明的聚氨酯组合物能够与表面处理剂一起使用,能够提高表面处理剂的效能、提高效能的耐久性(特别是洗涤耐久性)。
Claims (13)
1.一种聚氨酯化合物,其特征在于:
该聚氨酯化合物(A)包含由异氰酸酯(A1)和式:HO-Z(Y-R)n所示的长链醇(A2)形成的单元,
式中,R分别独立地为碳原子数7~40的烃基,
Y分别独立地为-O-、-NH-、-NH-C(=O)-、-C(=O)-NH-、-NH-C(=O)-O-、-NH-C(=O)-NH-、-C6H4-、-NH-(CH2)m-NH-、-NH-(CH2)m-O-、-O-C(=O)-、-C(=O)-O-、-NH-(CH2)m-O-C(=O)-、-NH-(CH2)m-C(=O)-O-、-O-C(=O)-NH-、-O-C6H4-、-NH-S(=O)2-、-S(=O)2-NH-、-NH-(CH2)m-O-C(=O)-NH-、-NH-(CH2)m-NH-C(=O)-O-、-NH-(CH2)m-C(=O)-NH-、-NH-(CH2)m-NH-C(=O)-、-NH-(CH2)m-NH-C(=O)-NH-、-NH-(CH2)m-O-C6H4-、-NH-(CH2)m-NH-C6H4-、-NH-(CH2)m-NH-S(=O)2-或-NH-(CH2)m-S(=O)2-NH-,其中m为1~5的整数,
Z为直接键合、或者2价或3价的碳原子数1~5的烃基,
n为1或2。
2.如权利要求1所述的聚氨酯化合物,其特征在于,还包含:
由选自封端剂(A3)和醇化合物(A4)中的至少1种形成的单元。
3.如权利要求1或2所述的聚氨酯化合物,其特征在于:
异氰酸酯(A1)为选自甲苯二异氰酸酯(TDI)、二苯甲烷二异氰酸酯(MDI)、MDI低聚物、萘-1,5-二异氰酸酯、苯二甲基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、4,4-二环己基甲烷二异氰酸酯、降冰片烷二异氰酸酯、异佛尔酮二异氰酸酯(IPDI)、二异氰酸酯的加成物、脲基甲酸酯改性物、缩二脲改性物、异氰脲酸酯改性物或碳二亚胺改性物和聚氨酯预聚物中的至少1种。
4.如权利要求1~3中任一项所述的聚氨酯化合物,其特征在于:
长链醇(A2)为选自下式中的至少1种,
HO-(CH2)m-NH-C(=O)-R、
HO-(CH2)m-C(=O)-NH-R、
HO-(CH2)m-O-C(=O)-R、
HO-(CH2)m-C(=O)-O-R、
HO-(CH2)m-NH-C(=O)-O-R、
HO-(CH2)m-O-C(=O)-NH-R、
HO-(CH2)m-NH-C(=O)-NH-R、
HO-(CH2)m-NH-S(=O)2-R、和
HO-(CH2)m-S(=O)2-NH-R,
式中,R为碳原子数12~30的烃基,
m为1~5的整数。
5.如权利要求2~4中任一项所述的聚氨酯化合物,其特征在于:
封端剂(A3)为选自肟、酚、醇、硫醇、酰胺、酰亚胺、咪唑、尿素、胺、亚胺、吡唑和活性亚甲基化合物中的至少1种。
6.如权利要求2~5中任一项所述的聚氨酯化合物,其特征在于:
醇化合物(A4)为单醇或多元醇,
单醇是C2或C3环氧烷与碳原子数1~10的起始一元醇加成而成的化合物,
多元醇是二元醇和具有3个以上羟基的多元醇,为选自低分子多元醇、聚醚多元醇、聚酯多元醇、聚酯聚碳酸酯多元醇、结晶性或非晶性的聚碳酸酯多元醇中的至少1种。
7.一种聚氨酯混合物,其特征在于:
含有权利要求1~6中任一项所述的聚氨酯化合物、以及选自多异氰酸酯(A1)、长链醇(A2)、封端剂(A3)和醇化合物(A4)中的至少1种。
8.一种水性聚氨酯组合物,其特征在于,含有:
权利要求1~6中任一项所述的聚氨酯化合物(A);和
水(B)。
9.如权利要求8所述的水性聚氨酯组合物,其特征在于:
水性聚氨酯组合物是水分散体。
10.如权利要求8或9所述的水性聚氨酯组合物,其特征在于:
水性聚氨酯组合物为交联剂或辅助剂。
11.一种权利要求8~10中任一项所述的水性聚氨酯组合物的制造方法,其特征在于:
将异氰酸酯(A1)和长链醇(A2)在有机溶剂中混合并使其反应,再与水混合。
12.一种基材的处理方法,其特征在于,包括:
利用含有权利要求1~6中任一项所述的聚氨酯化合物的表面处理组合物对基材进行处理的步骤。
13.一种经过处理的纤维制品,其特征在于:
权利要求1~6中任一项所述的聚氨酯化合物以交联物的形态附着于被处理物。
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