JPH02147688A - Icing-preventive composition - Google Patents
Icing-preventive compositionInfo
- Publication number
- JPH02147688A JPH02147688A JP30350788A JP30350788A JPH02147688A JP H02147688 A JPH02147688 A JP H02147688A JP 30350788 A JP30350788 A JP 30350788A JP 30350788 A JP30350788 A JP 30350788A JP H02147688 A JPH02147688 A JP H02147688A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- integer
- compound
- icing
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 229920005989 resin Polymers 0.000 claims abstract description 37
- 239000011347 resin Substances 0.000 claims abstract description 37
- -1 1,3-propylene Chemical group 0.000 claims abstract description 32
- 229920002050 silicone resin Polymers 0.000 claims abstract description 27
- 229920002545 silicone oil Polymers 0.000 claims abstract description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 230000002265 prevention Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- 239000003380 propellant Substances 0.000 claims description 8
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 7
- 239000000443 aerosol Substances 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- 239000008096 xylene Substances 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- QRYCGRZUSNDTIH-UHFFFAOYSA-N hydroperoxy-hydroxy-dimethylsilane Chemical class C[Si](C)(O)OO QRYCGRZUSNDTIH-UHFFFAOYSA-N 0.000 description 7
- 239000004645 polyester resin Substances 0.000 description 7
- 229920001225 polyester resin Polymers 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 229920000178 Acrylic resin Polymers 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 125000005372 silanol group Chemical group 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 239000003915 liquefied petroleum gas Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
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- 238000009472 formulation Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 2
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- 239000003921 oil Substances 0.000 description 2
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- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
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- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
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- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
- C09K3/185—Thawing materials
-
- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、新規な着氷防止組成物及び着氷防止方法に関
する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a novel anti-icing composition and method.
従来の技術及びその課題
自動車のフロントガラス、ワイパー ミラータイヤハウ
ス、鍵穴等の凍結した箇所を解氷させるため、アルコー
ル、エチレングリコール、界面活性剤などを炭酸ガス、
LPGガスなどの噴射ガス剤と共に充填し、凍結した箇
所に吹き付けて一時的に解凍させる解氷材が市販され、
使用されている。しかしながら、これらの解氷材は一時
的に解凍させるものであって効果が持続しない欠点があ
り、また事前に塗布しておいて結氷を防ぐ機能も有さな
い。Conventional technology and its problems In order to thaw frozen areas such as automobile windshields, wiper mirrors, tire houses, and keyholes, alcohol, ethylene glycol, surfactants, etc. are mixed with carbon dioxide gas,
Deicing materials are available on the market that are filled with a propellant gas such as LPG gas and sprayed onto frozen areas to temporarily thaw them.
It is used. However, these deicing agents have the disadvantage that their effects do not last because they temporarily thaw the ice, and they also do not have the ability to prevent ice formation by applying them in advance.
一般に、ヘラ、ハンマー、根棒などの道具を用いずに氷
を剥すことのできる着氷力の値は約1kg/cm2以下
であるが、市販解氷材は使用後再凍結すると1 kg/
cm2を超える値を示す。即ち、解氷材を噴射塗布し
た箇所は、よく水洗して薬液成分が残存しないようにし
ておかないと、再結氷したときはより強く着氷するとい
う欠点もある。In general, the value of the icing force that allows ice to be removed without using tools such as spatulas, hammers, and sticks is approximately 1 kg/cm2 or less, but commercially available de-icing materials have a value of 1 kg/cm2 or less when refrozen after use.
Indicates a value exceeding cm2. That is, unless the area where the deicing agent is sprayed is thoroughly washed with water to prevent any chemical components from remaining, there is also the disadvantage that when it refreezes, it will freeze even more strongly.
特開昭62−185776号公報には、グリコール、ア
クリル酸又はアルカリ金属アクリレートの単一重合体、
アクリルアミド/アクリル酸−共重合体又はアクリルア
ミド/アルカリ金属アクリレート−共重合体、アルカリ
金属アルキルアリールスルホナート、腐食防止剤、pH
調整のための3種の塩基性化合物及び水からなる除氷及
び着氷防止組成物が開示されている。この組成物は、飛
行機の離陸時など剪断力のかかる状態で除氷及び着氷防
止に効果的であるが、静止したものに対する除氷及び着
氷防止という点では、着氷力がまだ高いため不充分であ
る。JP-A-62-185776 discloses a homopolymer of glycol, acrylic acid or alkali metal acrylate,
Acrylamide/acrylic acid copolymer or acrylamide/alkali metal acrylate copolymer, alkali metal alkylaryl sulfonate, corrosion inhibitor, pH
A de-icing and anti-icing composition is disclosed comprising three basic compounds for conditioning and water. This composition is effective in deicing and preventing icing in situations where shearing forces are applied, such as when an airplane takes off, but its icing ability is still high in terms of deicing and preventing icing on stationary objects. It is insufficient.
課題を解決するための手段
従来から、容易に氷が除去でき、即ち着氷力が約1 k
g/ cm2より低く、かつ着氷防止効果が長期間持続
できる着氷防止剤が望まれており、この課題に向かって
本発明者は研究を重ねてきた。Means for solving the problem Conventionally, ice can be easily removed, that is, the icing force is about 1 k
There is a desire for an anti-icing agent that is lower than g/cm2 and can maintain its anti-icing effect for a long period of time, and the inventors have conducted repeated research toward this goal.
本発明者は、ジメチルポリシロキサン(シリコンオイル
)が疎水性で低表面エネルギーを有していることに着目
し、検討を行なったが、このものは、凝集力が低いため
氷の離脱と共に剥落し、低着氷力が持続しなかった。そ
こで本発明者はジメチルポリシロキサン鎖による低着氷
力の利点を生かし、かつ低着氷力を持続でき、上記課題
を解決できる着氷防止組成物を得るべく鋭意研究の結果
、特定のアルコキシジメチルシロキサン化合物を用いた
縮合物を含有する組成物が前記課題を解決できることを
見出し、本発明に到達した。The inventor of the present invention focused on the fact that dimethylpolysiloxane (silicone oil) is hydrophobic and has low surface energy, and conducted an investigation, but this material has a low cohesive force and does not peel off when the ice leaves. , the low icing force did not persist. Therefore, as a result of intensive research, the present inventors made use of the advantage of the low icing power due to dimethylpolysiloxane chains, and in order to obtain an anti-icing composition that could sustain the low icing power and solve the above problems, they discovered that a specific alkoxydimethyl The inventors have discovered that a composition containing a condensate using a siloxane compound can solve the above problems, and have arrived at the present invention.
即ち本発明は、一般式
〔式中、R1はメチル基またはエチル基を示し、Aは酸
素原子、エチレン基又は1,3−プロピレン基を示し、
aは5〜150の整数、b及びeは同−又は異なる1〜
3の整数を示し、Cは3−bSdは3−eの整数を示す
。〕
で表わされるアルコキシジメチルシロキサン化合物を縮
合して得られるか、或いは該一般式(1)の化合物と一
般式
(R3)i−8l (OR2)j (
II)〔式中、R2はメチル基又はエチル基を示し、R
3は炭素数1〜8のアルキル基を示し、iは0〜3の整
数、jは4−iを示す。〕
で表わされるアルコキシシラン化合物及び/又は一般式
〔式中、kは10〜200の整数を示す。〕で表わされ
るジヒドロキシジメチルシロキサン化合物との混合物を
共縮合して得られるシリコン樹脂(以下、「縮合シリコ
ン樹脂」と略称する。)を含有することを特徴とする着
氷防止組成物に係る。That is, the present invention relates to the general formula [wherein R1 represents a methyl group or an ethyl group, and A represents an oxygen atom, an ethylene group, or a 1,3-propylene group,
a is an integer from 5 to 150, b and e are the same or different from 1 to
C represents an integer of 3, and 3-bSd represents an integer of 3-e. ] It is obtained by condensing an alkoxydimethylsiloxane compound represented by the formula (R3)i-8l (OR2)j (
II) [In the formula, R2 represents a methyl group or an ethyl group, and R
3 represents an alkyl group having 1 to 8 carbon atoms, i represents an integer of 0 to 3, and j represents 4-i. ] An alkoxysilane compound and/or a general formula represented by [where k represents an integer of 10 to 200]. ] This relates to an anti-icing composition characterized by containing a silicone resin (hereinafter abbreviated as "condensed silicone resin") obtained by co-condensing a mixture with a dihydroxydimethylsiloxane compound represented by the following.
また、本発明は、該縮合シリコン樹脂と、更に湿気硬化
型被膜形成樹脂を含有する着氷防止組成物に係る。The present invention also relates to an anti-icing composition containing the condensed silicone resin and a moisture-curable film-forming resin.
また、本発明は、上記の着氷防止組成物を噴射ガス剤を
媒体とするエアロゾルとして塗布する着氷防止方法に係
る。The present invention also relates to an icing prevention method in which the above-mentioned icing prevention composition is applied as an aerosol using a propellant gas agent as a medium.
本発明における縮合シリコン樹脂としては、■前記一般
式(I)で表わされるアルコキシジメチルシロキサン化
合物(以下、「式(I)の化合物」と略称する。)の縮
合物、■式(I)の化合物と前記一般式(n)で表わさ
れるアルコキシシラン化合物との縮合物、0式(I)の
化合物と前記−般式(m)で表わされるジヒドロキシジ
メチルシロキサン化合物との縮合物、及び0式(I)の
化合物、式(n)のアルコキシシラン及び式(m)のジ
ヒドロキシジメチルシロキサンの3者の縮合物のうちの
いずれか一種もしくは二種以上の混合物が挙げられ、疎
水性ジメチルシロキサン鎖を多く有するものであり、特
に側鎖に疎水性ジメチルシロキサン鎖を有する櫛形縮合
物であることが好ましい。The condensed silicone resin in the present invention includes (1) a condensate of an alkoxydimethylsiloxane compound represented by the general formula (I) (hereinafter abbreviated as "compound of formula (I)"), (2) a compound of formula (I). and an alkoxysilane compound represented by the general formula (n), a condensate of a compound of the formula (I) and a dihydroxydimethylsiloxane compound represented by the general formula (m), and a condensate of the compound of the formula (I) ), an alkoxysilane of formula (n) and a condensation product of dihydroxydimethylsiloxane of formula (m). A comb-shaped condensate having a hydrophobic dimethylsiloxane chain in its side chain is particularly preferred.
上記■及び■の反応は、部分加水分解共縮合反応により
行なわれ、■の反応を代表的に示すと、となり、また、
■及び■の反応は上記と同様に部分加水分解共縮合反応
により行なうことができるが、また加水分解せずに行な
うこともでき、例えば■を例にとって示すと、
の反応を利用して行なうこともできる。The above reactions (1) and (2) are carried out by a partial hydrolysis co-condensation reaction, and the reaction (2) is typically shown as follows, and
Reactions (2) and (2) can be carried out by partial hydrolysis co-condensation reaction in the same manner as above, but they can also be carried out without hydrolysis. You can also do it.
上記■の反応において、式(I)の化合物と式(II)
のアルコキシシランとの比率は、両者の合計景に対して
、式(II)のアルコキシシランの口が30重量%以下
であることが好ましい。30重量%を超えると極性基で
あるアルコキシ基又は加水分解されたシラノール基が残
存し易くなり、着氷力が上がる原因となる。In the above reaction (■), a compound of formula (I) and a compound of formula (II)
It is preferable that the ratio of the alkoxysilane of formula (II) to the alkoxysilane of formula (II) is 30% by weight or less based on the total weight of both. If it exceeds 30% by weight, polar groups such as alkoxy groups or hydrolyzed silanol groups tend to remain, causing an increase in icing power.
また、上記■の反応において、式(I)の化合物と式(
III)のジヒドロキシジメチルシロキサンとの比率は
、両者の合計量に対して式(m)のジヒドロキシジメチ
ルシロキサンの量が80重量%以下であることが好ま1
7<、20〜70重足%の範囲にあることがより好まし
い。式(m)のジヒドロキシジメチルシロキサンの量が
80重合%を超えると、未反応のシラノール基が多く残
存し易くなり、着氷力が上がる原因となる。In addition, in the reaction (■) above, a compound of formula (I) and a compound of formula (
The ratio of dihydroxydimethylsiloxane of formula (m) to dihydroxydimethylsiloxane of formula (m) is preferably 80% by weight or less based on the total amount of both.
It is more preferable that the content is in the range of 7<, 20 to 70% by weight. When the amount of dihydroxydimethylsiloxane of formula (m) exceeds 80% polymerization, many unreacted silanol groups tend to remain, which causes an increase in icing power.
また、上記■の反応において式(I)の化合物、式(I
I)のアルコキシシラン及び式(IIII)のジヒドロ
キシジメチルシロキサンの3者の比率は、3者の合計量
に対し、
式(I)の化合物:好ましくは20重量%以上、更に好
ましくは30〜70重量%、
式(U)のアルコキシシラン:好ましくは30重M%以
下、更に好ましくは20重量%以下、式(III)のジ
ヒドロキンジメチルシロキサン:好ましくは80重重量
以下、更に好ましくは30〜70重量96
の範囲内にあることが適当である。In addition, in the reaction (①) above, the compound of formula (I), the compound of formula (I
The ratio of the alkoxysilane of I) and the dihydroxydimethylsiloxane of formula (III) is as follows: Compound of formula (I): preferably 20% by weight or more, more preferably 30 to 70% by weight, based on the total amount of the three. %, alkoxysilane of formula (U): preferably 30% by weight or less, more preferably 20% by weight or less, dihydroquine dimethylsiloxane of formula (III): preferably 80% by weight or less, more preferably 30 to 70% by weight It is appropriate that it be within the range of 96.
式(I)の化合物の量が20重量%未満では、側鎖とな
る疎水性のジメチルシラン基の量が少なくなり着氷力が
上がる原因となる。If the amount of the compound of formula (I) is less than 20% by weight, the amount of hydrophobic dimethylsilane groups serving as side chains will decrease, causing an increase in icing power.
式(II)のアルジキシシランの盆が30重量%Gmえ
るど極性基であるアルコキシ基又は加水分解されたシラ
ノール基が残存しやすくなり、着氷力が上がる原因とな
る。When the aldoxysilane tray of formula (II) has 30% Gm by weight, alkoxy groups or hydrolyzed silanol groups, which are polar groups, tend to remain, which causes an increase in icing power.
また式(m)のジヒドロキシジメチルシロキサンの毒が
80重旦%を超えると未反応のシラノール基が多く残存
し易くなり、着氷力が上がる原因となる。Furthermore, if the toxicity of the dihydroxydimethylsiloxane of formula (m) exceeds 80% by weight, many unreacted silanol groups tend to remain, which causes an increase in icing power.
本発明組成物において、縮合シリコン樹脂は式(I)の
化合物を縮合して得られるか、又は式(I)の化合物と
式(IT)のアルキコシシラン及び/又は式(III)
のジヒドロキシジメチルシロキ・サンとの混合物を共縮
合して得られるが、得られる縮合シリコン樹脂の重量平
均分子貴が15000〜200000、好ましくは20
000〜150000の範囲となるよう、原料種、配合
割合、反応触媒種、触媒量、反応温度、反応時間を適宜
選択することが好ましい。反応触媒としては、塩酸や硫
酸などの鉱酸;ギ酸や酢酸などの有機酸;マンガン、コ
バルト、鉛、ニッケル、鉄、スズ及び亜鉛などの金属の
、ステアリン酸塩、オクチル酸塩などの脂肪酸塩、及び
これらの金属のアセチルアセトン錯体が挙げられる。こ
れらの反応触媒は、通常(I)〜(III)で表わされ
るシリコン化合物の総和100重量部に対して0.00
1〜1重皿部の範囲で使用される。また縮合反応は、通
常50〜150°Cの温度で30分〜10時間加熱する
ことによって行なわれる。In the composition of the present invention, the condensed silicone resin is obtained by condensing the compound of formula (I), or the compound of formula (I) and the alkoxysilane of formula (IT) and/or the alkoxysilane of formula (III)
is obtained by co-condensing a mixture with dihydroxydimethylsiloxane of
It is preferable to appropriately select the raw material type, blending ratio, reaction catalyst type, catalyst amount, reaction temperature, and reaction time so as to fall within the range of 000 to 150,000. Reaction catalysts include mineral acids such as hydrochloric acid and sulfuric acid; organic acids such as formic acid and acetic acid; fatty acid salts of metals such as manganese, cobalt, lead, nickel, iron, tin, and zinc, such as stearates and octylates. , and acetylacetone complexes of these metals. These reaction catalysts are usually used in an amount of 0.00 parts by weight per 100 parts by weight of the silicon compounds represented by (I) to (III).
It is used in the range of 1 to 1 double plate portion. The condensation reaction is usually carried out by heating at a temperature of 50 to 150°C for 30 minutes to 10 hours.
本発明においては、前記縮合シリコン樹脂のみ、又は縮
合シリコン樹脂と有機溶剤とからなっていてもよいが、
被膜強度や素地との密着性を向上させて着氷防止効果の
持続性の向上を図るため、湿気硬化型被膜形成樹脂を配
合することがより好ましい。In the present invention, the condensed silicone resin may be composed of only the condensed silicone resin, or the condensed silicone resin and an organic solvent.
In order to improve the film strength and adhesion to the base material and to improve the durability of the anti-icing effect, it is more preferable to blend a moisture-curable film-forming resin.
本発明において、湿気硬化型被膜形成樹脂としては、一
般式
〔式中、R5は炭素数1〜10までのアルキル基、アリ
ール基、アラルキル基より選ばれる炭化水素基、Zはハ
ロゲン、アルコキシ、アシロキシ、フェノキシ及びチオ
アルコキシ基より選ばれる基、tは1〜3の整数である
。〕で表わされる末端或いは側鎖に加水分解性基と結合
した珪素基を1分子中に少なくとも1個、好ましくは2
個以上有する樹脂である。In the present invention, the moisture-curable film-forming resin has the general formula [wherein R5 is a hydrocarbon group selected from an alkyl group, an aryl group, and an aralkyl group having 1 to 10 carbon atoms, and Z is a halogen, alkoxy, or acyloxy , a group selected from phenoxy and thioalkoxy groups, and t is an integer of 1 to 3. ] At least 1 silicon group, preferably 2 silicon groups bonded to a hydrolyzable group at the terminal or side chain in one molecule.
It is a resin having more than
上記の加水分解性基と結合した珪素基を樹脂中に導入す
る方法としては、
(a)一般式
H−8t妖Z)1
〔式中、R5、Z及びtは上記の通り。〕で表わされる
ヒドロシラン化合物を重合性炭素−炭素二重結合を有す
る樹脂と■族遷移金属触媒の存在下でヒドロシリル化反
応させる方法、
(b)一般式
〔式中、R6は重合性炭素−炭素二重結合を有する有機
残基、R5、z及びtは前記の通り。〕で表わされるシ
ラン化合物と重合性不飽和化合物とをラジカル共重合さ
せる方法
等が有効に利用できる。As a method for introducing the silicon group bonded to the above-mentioned hydrolyzable group into the resin, (a) General formula H-8t-Z)1 [wherein R5, Z and t are as described above. ] A method of hydrosilylating a hydrosilane compound represented by the following with a resin having a polymerizable carbon-carbon double bond in the presence of a group II transition metal catalyst; The organic residues having a double bond, R5, z and t are as described above. ] A method of radical copolymerization of a silane compound and a polymerizable unsaturated compound can be effectively used.
前記(a)法に使用されるヒドロシラン化合物を具体的
に例示すると、メチルジクロルシラン、トリクロルシラ
ン、フエニルジクロルシランの如きハロゲン化シラン類
;メチルジェトキシシラン、メチルジメトキシシラン、
フエニルジメトキシシラン、トリメトキシシラン、トリ
エトキシシランの如きアルコキシシラン類;メチルジア
セトキシシラン、フエニルジアセトキシシラン、トリア
セトキシシランの如きアシロキシシラン類等の各種シラ
ン類が挙げられる。Specific examples of the hydrosilane compounds used in the method (a) include halogenated silanes such as methyldichlorosilane, trichlorosilane, and phenyldichlorosilane; methyljethoxysilane, methyldimethoxysilane,
Examples include various silanes such as alkoxysilanes such as phenyldimethoxysilane, trimethoxysilane and triethoxysilane; and acyloxysilanes such as methyldiacetoxysilane, phenyldiacetoxysilane and triacetoxysilane.
これらのヒドロシラン化合物のうち、ハロゲン化シラン
類も容易に使用できるが、ハロゲン化シラン類を用いて
得られる、加水分解性基と結合した珪素基を有する樹脂
は、空気中に暴露すると塩化水素を発生しながら常温で
速やかに硬化するが、塩化水素による刺激臭や腐食に問
題があり限定された用途にしか実用上使用できないので
、更に続いてハロゲン官能基を他の加水分解性官能基に
変換することが望ましい。Among these hydrosilane compounds, halogenated silanes can also be easily used, but resins containing silicon groups bonded to hydrolyzable groups, which are obtained using halogenated silanes, release hydrogen chloride when exposed to air. Although it cures quickly at room temperature while generating hydrogen chloride, it can only be used in limited applications due to problems with the irritating odor and corrosion caused by hydrogen chloride, so the halogen functional group is subsequently converted to other hydrolyzable functional groups. It is desirable to do so.
(a)法に使用される重合性炭素−炭素二重結合を有す
る樹脂としては、水酸基を有さない樹脂であることが必
要であり、ビニル系樹脂、ポリエステル系樹脂、ポリブ
タジェン系樹脂、ウレタン系樹脂等が使用できる。The resin having a polymerizable carbon-carbon double bond used in method (a) must be a resin without hydroxyl groups, such as vinyl resin, polyester resin, polybutadiene resin, or urethane resin. Resin etc. can be used.
上記ビニル系樹脂としては、メチル(メタ)アクリレー
ト、エチル(メタ)アクリレート、プロピル(メタ)ア
クリレート、n−ブチル(メタ)アクリレート、i−ブ
チル(メタ)アクリレート、t−ブチル(メタ)アクリ
レート、2−エチルヘキシル(メタ)アクリレート、シ
クロヘキシル(メタ)アクリレート、n−オクチル(メ
タ)アクリレート、ラウリル(メタ)アクリレート、シ
クロヘキシル(メタ)アクリレート及びベンジル(メタ
)アクリレート等の(メタ)アクリル酸エステル;スチ
レン、α−メチルスチレン、ビニルトルエン、p−クロ
ルスチレン、p−t−ブチルスチレン等のビニル芳香族
化合物; (メタ)アクリル酸、クロトン酸、フマル酸
、(無水)マレイン酸、(無水)イタコン酸等の不飽和
カルボン酸;グリシジル(メタ)アクリレート、ビニル
グリシジルエーテル、アリルグリシジルエーテル等のグ
リシジル基含有ビニル化合物;酢酸ビニル、安息香酸ビ
ニル、rVEOVAJ (シェル化学■商品)のよう
なビニルエステル類; (メタ)アクリルアミド、N、
N−ジメチル(メタ)アクリルアミド、N−アルコキシ
メチル化(メタ)アクリルアミド、ジアセトンアクリル
アミド、N−メチロール(メタ)アクリルアミドのよう
なカルボン酸アミド系単量体; (メタ)アクリロニト
リルのようなシアノ基含有単量体、N、N−ジメチルア
ミノエチル(メタ)アクリレ−)、N、N−ジエチルア
ミノエチル(メタ)アクリレート等のN、N−ジアルキ
ルアミノアルキル(メタ)アクリレート系3級アミノ基
含有単景体;n−ブチルビニルエーテル、エチルビニル
エーテル、メチルビニルエーテル等のビニルエーテル類
等のビニル系化合物を共重合して成る共重合体を主成分
とする樹脂である。Examples of the vinyl resin include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, i-butyl (meth)acrylate, t-butyl (meth)acrylate, 2 - (meth)acrylic acid esters such as ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-octyl (meth)acrylate, lauryl (meth)acrylate, cyclohexyl (meth)acrylate and benzyl (meth)acrylate; styrene, α - Vinyl aromatic compounds such as methylstyrene, vinyltoluene, p-chlorostyrene, and pt-butylstyrene; (meth)acrylic acid, crotonic acid, fumaric acid, (anhydrous) maleic acid, (anhydrous) itaconic acid, etc. Unsaturated carboxylic acids; vinyl compounds containing glycidyl groups such as glycidyl (meth)acrylate, vinyl glycidyl ether, and allyl glycidyl ether; vinyl esters such as vinyl acetate, vinyl benzoate, and rVEOVAJ (Shell Chemical ■product); (meth) acrylamide, N,
Carboxylic acid amide monomers such as N-dimethyl(meth)acrylamide, N-alkoxymethylated (meth)acrylamide, diacetone acrylamide, and N-methylol(meth)acrylamide; Cyano group-containing such as (meth)acrylonitrile Monomers, N,N-dialkylaminoalkyl (meth)acrylate-based tertiary amino group-containing monomers such as N,N-dimethylaminoethyl (meth)acrylate) and N,N-diethylaminoethyl (meth)acrylate ; It is a resin whose main component is a copolymer formed by copolymerizing vinyl compounds such as vinyl ethers such as n-butyl vinyl ether, ethyl vinyl ether, and methyl vinyl ether.
この共重合体の製造時に、一部アクリル酸アリルやメタ
クリル酸アリル等を配合しアゾ系重合開始剤を使用して
ラジカル重合させることによって共重合体中に重合性炭
素−炭素二重結合であるアリル基を導入することができ
る。また共重合体製造時に一部アクリル酸2−ヒドロキ
シエチルやメタアクリル酸2−ヒドロキシエチル等の水
酸基含有重合性不飽和化合物を共重合させ、この水酸基
全量に、イソホロンジイソシアネート又はトリレンジイ
ソシアネートとヒドロキシ(メタ)アクリレートとの1
/1モル付加物、イソシアノエチルアクリレート、イソ
シアノエチルメタクリレート、及びm−イソプロペニル
−α、α′−ジメチルベンジルイソシアネートのような
イソシアネート基を有する重合性不飽和化合物を反応さ
せることによって重合性二重結合を導入することができ
る。During the production of this copolymer, allyl acrylate, allyl methacrylate, etc. are partially blended and radical polymerization is performed using an azo polymerization initiator to form polymerizable carbon-carbon double bonds in the copolymer. Allyl groups can be introduced. In addition, during copolymer production, a portion of a hydroxyl group-containing polymerizable unsaturated compound such as 2-hydroxyethyl acrylate or 2-hydroxyethyl methacrylate is copolymerized, and the entire amount of hydroxyl groups is added with isophorone diisocyanate or tolylene diisocyanate and hydroxy ( 1 with meth)acrylate
/1 mole adduct, isocyanoethyl acrylate, isocyanoethyl methacrylate, and polymerizable double bonds by reacting polymerizable unsaturated compounds having isocyanate groups such as m-isopropenyl-α,α′-dimethylbenzyl isocyanate. can be introduced.
逆に、共重合体中にイソシアネート基を含有させ、この
イソシアネート基に水酸基含有重合性不飽和化合物を反
応させる方法によっても導入することができる。上記イ
ソシアネート基と水酸基との反応以外に、水酸基とカル
ボキシル基、水酸基と酸無水基との反応等、相互に反応
することができる官能基の反応を利用して共重合体に重
合性二重結合を導入することができる。Conversely, it can also be introduced by a method of containing isocyanate groups in the copolymer and reacting the isocyanate groups with a hydroxyl group-containing polymerizable unsaturated compound. In addition to the reaction between isocyanate groups and hydroxyl groups mentioned above, reactions of functional groups that can react with each other, such as reactions between hydroxyl groups and carboxyl groups, and hydroxyl groups and acid anhydride groups, are used to create polymerizable double bonds in copolymers. can be introduced.
(a)法に使用されるポリエステル系樹脂としては、通
常のポリエステル樹脂の製造に用いられる有機酸成分及
びアルコール成分を原料に用いて縮合してなるポリエス
テル樹脂を主成分とするものである。有機酸成分として
は、通常多塩基酸が用いられ、多塩基酸としては、例え
ばフタル酸、イソフタル酸、テレフタル酸、テトラヒド
ロフタル酸、テトラヒドロテレフタル酸、ヘキサヒドロ
フタル酸、ヘキサビトロイソフタル酸、ヘキサヒドロテ
レフタル酸、ヘット酸、トリメリット酸、ヘキサヒドロ
トリメリット酸、ピロメリット酸、シクロヘキサンテト
ラカルボン酸、メチルテトラヒドロフタル酸、メチルへ
キサヒドロフタル酸、エンドメチレンへキサヒドロフタ
ル酸、メチルエンドメチレンテトラヒドロフタル酸、マ
レイン酸、フマル酸、イタコン酸、コハク酸、グルタル
酸、アジピン酸、アゼライン酸、セパチン酸、デカンジ
カルボン酸、スペリン酸、ピメリン酸、ダイマー酸くト
ール油脂肪酸の二量体)、テトラクロロフタル酸、ナフ
タレンジカルボン酸、4,4′ジフエニルメタンジカル
ボン酸、4.4”−ジカルボキシビフェニル等やこれら
の酸無水物やジアルキルエステル、特にジメチルエステ
ル等が挙げられる。The polyester resin used in method (a) is mainly composed of a polyester resin obtained by condensing organic acid components and alcohol components used in the production of ordinary polyester resins as raw materials. As the organic acid component, polybasic acids are usually used, and examples of the polybasic acids include phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, tetrahydroterephthalic acid, hexahydrophthalic acid, hexabitroisophthalic acid, and hexahydrophthalic acid. Terephthalic acid, hetate acid, trimellitic acid, hexahydrotrimellitic acid, pyromellitic acid, cyclohexanetetracarboxylic acid, methyltetrahydrophthalic acid, methylhexahydrophthalic acid, endomethylene hexahydrophthalic acid, methylendomethylenetetrahydrophthalic acid acids, maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, cepatic acid, decanedicarboxylic acid, superic acid, pimelic acid, dimer of tall oil fatty acids), tetrachloro Examples include phthalic acid, naphthalenedicarboxylic acid, 4,4'-diphenylmethanedicarboxylic acid, 4.4''-dicarboxybiphenyl, and their acid anhydrides and dialkyl esters, especially dimethyl ester.
またアルコール成分としては、通常二価アルコールや三
価アルコール等が用いられる。二価アルコールとしては
、例えばエチレングリコール、プロピレングリコール、
1,4−ブタンジオール、1.3−ブタンジオール、2
,3−ブタンジオール、1,2−ブタンジオール、1,
5−ベンタンジオール、1,4−ベンタンジオール、2
,4−ベンタンジオール、2,3−ジメチルトリメチレ
ングリコール、3−メチル−ペンタン−1,5−ジオー
ル、3−メチル−4,5−ベンタンジオール、2. 2
.4−トリメチル−1,3−ベンタンジオール、1,6
−ヘキサンジオール、1,5−ヘキサンジオール、1,
4−ヘキサンジオール、2.5−ヘキサンジオール、1
,4−シクロヘキサンジメタツール、ジエチレングリコ
ール、ジプロピレングリコール、トリエチレングリコー
ル、ネオペンチルグリコール、ヒドロキシピバリン酸ネ
オペンチルグリコールエステル、ポリアルキレンオキサ
イド、ビスヒドロキシエチルテレフタレート、(水素添
加)ビスフェノールAのアルキレンオキサイド付加物等
が挙げられる。またカージュラE10〔シェル化学社製
〕、α−オレフィンエポキシド、ブチレンオキサイド等
のモノエポキシ化合物もグリコールの1種として使用で
きる。Further, as the alcohol component, dihydric alcohol, trihydric alcohol, etc. are usually used. Examples of dihydric alcohols include ethylene glycol, propylene glycol,
1,4-butanediol, 1,3-butanediol, 2
, 3-butanediol, 1,2-butanediol, 1,
5-bentanediol, 1,4-bentanediol, 2
, 4-bentanediol, 2,3-dimethyltrimethylene glycol, 3-methyl-pentane-1,5-diol, 3-methyl-4,5-bentanediol, 2. 2
.. 4-trimethyl-1,3-bentanediol, 1,6
-hexanediol, 1,5-hexanediol, 1,
4-hexanediol, 2.5-hexanediol, 1
, 4-cyclohexane dimetatool, diethylene glycol, dipropylene glycol, triethylene glycol, neopentyl glycol, hydroxypivalic acid neopentyl glycol ester, polyalkylene oxide, bishydroxyethyl terephthalate, (hydrogenated) alkylene oxide adduct of bisphenol A etc. Monoepoxy compounds such as Cardura E10 (manufactured by Shell Chemical Co., Ltd.), α-olefin epoxide, and butylene oxide can also be used as a type of glycol.
また三価以上の多価アルコールとしては、例えばグリセ
リン、トリメチロールプロパン、トリメチロールエタン
、ジグリセリン、ペンタエリスリトール、ジペンタエリ
スリトール、ソルビトール等が挙げられる。Examples of trihydric or higher polyhydric alcohols include glycerin, trimethylolpropane, trimethylolethane, diglycerin, pentaerythritol, dipentaerythritol, and sorbitol.
また、分子内にカルボン酸及び水酸基の双方を有する化
合物も使用できる。斯かる化合物としては、例えばジメ
チロールプロピオン酸、ピバリン酸、12−ヒドロキシ
ステアリン酸、リシノール酸等が挙げられる。またε−
カプロラクトン、γ−バレロラクトン等のラクトン類も
環状エステル化合物なので、上記化合物の範時に属する
。Furthermore, compounds having both carboxylic acid and hydroxyl groups in the molecule can also be used. Examples of such compounds include dimethylolpropionic acid, pivalic acid, 12-hydroxystearic acid, and ricinoleic acid. Also ε−
Lactones such as caprolactone and γ-valerolactone are also cyclic ester compounds and therefore belong to the above-mentioned category of compounds.
上記有機酸成分やアルコール成分の一部を、各種の天然
及び合成の高級脂肪酸、高級アルコール、アクリル酸2
−ヒドロキシエチル、メタクリル酸2−ヒドロキシエチ
ル、アクリル酸、メタクリル酸、安息香酸、p−t−ブ
チル安息香酸等の一官能性原料や天然の油類で置き換え
ることもできる。Some of the above organic acid components and alcohol components are combined with various natural and synthetic higher fatty acids, higher alcohols, and acrylic acid 2.
-Hydroxyethyl methacrylate, 2-hydroxyethyl methacrylate, acrylic acid, methacrylic acid, benzoic acid, pt-butylbenzoic acid, and other monofunctional raw materials or natural oils can also be substituted.
有機酸成分やアルコール成分として重合性不飽和基を有
するものを使用することによって樹脂中に重合性二重結
合を導入することができる。その他の方法とし7て、有
機酸成分及びアルコール成分を縮合してなるポリエステ
ル樹脂が水酸基を有する場合、この水酸基の全量に、前
記イソシアネート基を有する重合性不飽和化合物を反応
させることによって重合性二重結合を導入することがで
きる。また、この水酸基の全量に、カルボキシル基また
は酸無水基を有する重合性不飽和化合物を反応させるこ
とによって重合性二重結合を導入することもできる。一
方、ポリエステル樹脂がカルボキシル基を有する場合に
は、カルボキシル基に対して当合以下の水酸基を有する
重合性不飽和化合物を反応させることによって重合性二
重結合を導入できる。By using an organic acid component or an alcohol component having a polymerizable unsaturated group, a polymerizable double bond can be introduced into the resin. As another method 7, when the polyester resin formed by condensing an organic acid component and an alcohol component has hydroxyl groups, the entire amount of the hydroxyl groups is reacted with the polymerizable unsaturated compound having an isocyanate group to form a polymerizable compound. Double bonds can be introduced. Furthermore, a polymerizable double bond can be introduced by reacting the entire amount of the hydroxyl groups with a polymerizable unsaturated compound having a carboxyl group or an acid anhydride group. On the other hand, when the polyester resin has a carboxyl group, a polymerizable double bond can be introduced by reacting a polymerizable unsaturated compound having a hydroxyl group equal to or less than that of the carboxyl group.
上記(a)法においては、ヒドロシラン化合物を重合性
二重結合に反応させる段階で遷移金属錯体が触媒として
必要である。遷移金属錯体触媒としては、白金、ロジウ
ム、コバルト、パラジウム及びニッケルから選ばれた■
族遷移金属錯体化合物が有効に使用され、このヒドロシ
リル化反応は、通常50〜150°Cの任意の温度で1
〜10時間程度反応させることによって達成される。In the above method (a), a transition metal complex is required as a catalyst in the step of reacting a hydrosilane compound with a polymerizable double bond. The transition metal complex catalyst is selected from platinum, rhodium, cobalt, palladium and nickel.
Group transition metal complex compounds are effectively used, and the hydrosilylation reaction is typically carried out at any temperature between 50 and 150°C.
This is achieved by reacting for about 10 hours.
用いるヒドロシラン化合物の量は、ビニル系樹脂中に含
まれる炭素−炭素二重結合に対し、任意愈の使用が可能
であるが、0.5〜2倍モルの使用が好ましい。これ以
上のシラン量の使用を妨げるものではないが未反応のヒ
ドロシランとして回収されるだけである。The amount of the hydrosilane compound to be used can be set arbitrarily, but it is preferably used in an amount of 0.5 to 2 times the mole of carbon-carbon double bonds contained in the vinyl resin. Although this does not preclude the use of a larger amount of silane, it will simply be recovered as unreacted hydrosilane.
前記(b)法において使用されるシラン化合物としては
、例えばγ−アクリロイルオキシプロピルメチルジメト
キシシラン、γ−アクリロイルオキシプロピルトリメト
キシシラン、γ−アクリロイルオキシプロピルメチルジ
クロロシラン、γ−アクリロイルオキシプロピルトリク
ロロシラン、γ−メタクリロイルオキシプロピルメチル
ジメトキシシラン、γ−メタクリロイルオキシプロピル
トリメトキシシラン、
及び
等が挙げられる。Examples of the silane compounds used in the method (b) include γ-acryloyloxypropylmethyldimethoxysilane, γ-acryloyloxypropyltrimethoxysilane, γ-acryloyloxypropylmethyldichlorosilane, γ-acryloyloxypropyltrichlorosilane, Examples include γ-methacryloyloxypropylmethyldimethoxysilane, γ-methacryloyloxypropyltrimethoxysilane, and the like.
(b)法において上記シラン化合物と共重合させる重合
性不飽和化合物としては、前記(a)法におけるビニル
系樹脂の主成分である共重合体の合成に使用されるビニ
ル系化合物を使用できる。As the polymerizable unsaturated compound to be copolymerized with the silane compound in the method (b), a vinyl compound used in the synthesis of the copolymer that is the main component of the vinyl resin in the method (a) can be used.
これらビニル系化合物とシラン化合物の共重合体の合成
は、通常の溶液重合法で行なわれ、ビニル系化合物、シ
ラン化合物、ラジカル開始剤、また適当な分子】のシリ
ル基含有共重合体を得るために必要に応じてn−ドデシ
ルメルカプタン、t−ドデシルメルカプタンの如き連鎖
移動剤を加え50〜150°Cで反応させる。溶剤は、
使用しても、しなくてもよいが、使用する場合はエーテ
ル類、炭化水素類、酢酸エステル類の如き非反応性の溶
剤の使用が好ましい。Synthesis of these copolymers of vinyl compounds and silane compounds is carried out by ordinary solution polymerization methods to obtain silyl group-containing copolymers of vinyl compounds, silane compounds, radical initiators, and appropriate molecules. If necessary, a chain transfer agent such as n-dodecylmercaptan or t-dodecylmercaptan is added to the reaction mixture at 50 to 150°C. The solvent is
It may or may not be used, but when used, it is preferable to use a non-reactive solvent such as ethers, hydrocarbons, and acetic esters.
本発明における湿気硬化型樹脂組成物の分子量は特に限
定されるものではないが、被膜形成時の塗装性及び被膜
形成性の点から重量平均分子量3000〜200000
が好ましく、更に5000〜100000の範囲内にあ
ることがより好ましい。The molecular weight of the moisture-curable resin composition in the present invention is not particularly limited, but from the viewpoint of coating properties and film forming properties, the weight average molecular weight is 3,000 to 200,000.
is preferable, and more preferably within the range of 5,000 to 100,000.
(a)法又は(b)法によって得られた、加水分解性基
と結合した珪素基を有する樹脂は、公知の方法で加水分
解性基を他の加水分解性基に変換することが可能である
。In the resin having a silicon group bonded to a hydrolyzable group obtained by method (a) or method (b), the hydrolyzable group can be converted into another hydrolyzable group by a known method. be.
本発明組成物が、上記湿気硬化型被膜形成樹脂を含有す
る場合、縮合シリコン樹脂と湿気硬化型被膜形成樹脂と
の反応性シリル基間の縮合反応を速やかに進行させ、被
膜強度を増大させる目的で、一般式
〔式中、R3及びR4は同−又は異なってメチル基又は
エチル基を示し、D及びEは同−又は異なって酸素原子
、エチレン基又は1,3−プロピレン基を示す。Xは3
〜30の整数を示し、又、m及びrは同−又は異なって
1〜3の整数を示し、nは3−m、Sは3−rを示す。When the composition of the present invention contains the moisture-curable film-forming resin, the purpose is to rapidly advance the condensation reaction between the reactive silyl groups of the condensed silicone resin and the moisture-curable film-forming resin to increase film strength. and the general formula [wherein R3 and R4 are the same or different and represent a methyl group or an ethyl group, and D and E are the same or different and represent an oxygen atom, an ethylene group or a 1,3-propylene group. X is 3
It represents an integer of ~30, m and r are the same or different and represent an integer of 1 to 3, n represents 3-m, and S represents 3-r.
〕
で表わされる両末端アルコキシシリル基含有ジメチルシ
ロキサン化合物を必要に応じて配合することができる。] A dimethylsiloxane compound containing an alkoxysilyl group at both terminals represented by the following can be blended as necessary.
縮合シリコン樹脂と湿気硬化型被膜形成樹脂との混合物
を被塗物に塗布した場合、湿気硬化型被膜形成樹脂が下
層(被塗物側)に、縮合シリコン樹脂が上層(大気側)
に偏在し、この両者の樹脂の結合を促進し、長期の低着
氷力持続性の改良に(IV)式のジメチルシロキサンは
役立つものである。When a mixture of condensed silicone resin and moisture-curable film-forming resin is applied to an object, the moisture-curable film-forming resin is in the lower layer (on the object side) and the condensed silicone resin is in the upper layer (atmospheric side).
The dimethylsiloxane of formula (IV) is unevenly distributed in the siloxane, promotes the bonding of both resins, and is useful for improving the long-term sustainability of low icing power.
本発明組成物には、更に必要に応じて、一般式
〔式中、yは1〜20000の整数を示す。〕で表わさ
れるシリコーンオイルを配合することができる。(V)
式のシリコーンオイルを本発明組成物中に配合すること
によって、縮合シリコン樹脂中の疎水性のポリジメチル
シロキサン鎖とアルキル鎖の大気側への配向を促し、極
性の高いアルコキシシリル基の大気表面側への配向を防
ぎやすくする。The composition of the present invention may further contain a compound having the general formula [where y represents an integer of 1 to 20,000], if necessary. ] can be blended. (V)
By blending the silicone oil of the formula into the composition of the present invention, the hydrophobic polydimethylsiloxane chains and alkyl chains in the condensed silicone resin are promoted to the atmosphere side, and the highly polar alkoxysilyl groups are directed to the atmosphere surface side. Make it easier to prevent orientation.
本発明組成物において、縮合シリコン樹脂、湿気硬化型
被膜形成樹脂、(TV)式のジメチルシロキサン及び(
V)式のシリコーンオイルの配合割合は、これれら4者
の合計量に対し、以下の範囲内にあることが望ましい。In the composition of the present invention, a condensed silicone resin, a moisture-curable film-forming resin, a dimethylsiloxane of the (TV) formula, and a (
The blending ratio of the silicone oil of formula V) is preferably within the following range with respect to the total amount of these four components.
縮合シリコン樹脂:2〜100重口%、好ましくは5〜
95重量%、
湿気硬化型被膜形成樹脂:98重ユニ以下、好ましくは
3〜95重合%、
(rV)式のジメチルシロキサ2230重量%以下、好
ましくは20重重量以下、
(V)式のシリコーンオイル:30重11%以下好まし
くは20重量%以下。Condensed silicone resin: 2-100% by weight, preferably 5-100% by weight
95% by weight, moisture-curable film-forming resin: 98% by weight or less, preferably 3 to 95% by weight, dimethylsiloxa of formula (rV) 2230% by weight or less, preferably 20% by weight or less, silicone of formula (V) Oil: 30 weight 11% or less, preferably 20 weight % or less.
縮合シリコン樹脂の盆が2重世%未満又は、湿気硬化型
被膜形成樹脂の量が98重量%を超えた場合には、着氷
力が上がる傾向がある。(IV)式のジメチルシロキサ
ンの足が30重量%を超えると未反応のアルコキシ基が
多く残存し着氷力を上げる虞れがある。また(V)式の
シリコーンオイルの量が30重重量を超えると、塗布し
た組成物被膜の乾燥性が劣り表面が汚れ易くなったり、
素地への密着性が悪くなる傾向がある。If the content of the condensed silicone resin tray is less than 2% by weight or if the amount of moisture-curable film-forming resin exceeds 98% by weight, the icing power tends to increase. If the proportion of dimethylsiloxane of formula (IV) exceeds 30% by weight, many unreacted alkoxy groups remain, which may increase the icing power. Furthermore, if the amount of silicone oil of formula (V) exceeds 30 weight, the drying properties of the applied composition film will be poor and the surface will become easily stained.
Adhesion to the substrate tends to deteriorate.
また、本発明組成物は、有機溶剤を含有L2ていてもよ
く、また噴射ガス剤と共に密閉容器中に充1填すること
により手軽に吹付けのできるエアゾール噴射式着氷防止
剤とすることができる。有機溶剤としては、本発明組成
物を溶解乃至は分散できるものであれば使用でき、例え
ば、キシレン、トルエン、メタノール、エタノール、イ
ソプロパツール、n−ブタノール、イソブタノール、酢
酸エチル、酢酸ブチル、メチルエチルケトン、メチルイ
ソブチルケトン、ヘキサン、ヘプタン、イソオクタン、
エチレングリコール、モノエチルエーテル、エチレング
リコールモノブチルエーテル、酢酸エチレングリコール
モノメチルエーテル等を適宜使用することができる。噴
射ガス剤としては、液化石油ガス(LPG)、液化炭酸
ガス及びフロンガス等通常、エアゾール用噴射ガス剤と
して利用されているものを使用できる。本発明組成物は
エアゾールとして塗布できるほか、ハケ塗りやスプレー
塗装によって塗布できる。Further, the composition of the present invention may contain an organic solvent, and can be made into an aerosol injection type anti-icing agent that can be easily sprayed by filling it into a closed container together with a propellant gas agent. can. Any organic solvent that can dissolve or disperse the composition of the present invention can be used, such as xylene, toluene, methanol, ethanol, isopropanol, n-butanol, isobutanol, ethyl acetate, butyl acetate, and methyl ethyl ketone. , methyl isobutyl ketone, hexane, heptane, isooctane,
Ethylene glycol, monoethyl ether, ethylene glycol monobutyl ether, acetic acid ethylene glycol monomethyl ether, etc. can be used as appropriate. As the propellant gas agent, those normally used as propellant gas agents for aerosols can be used, such as liquefied petroleum gas (LPG), liquefied carbon dioxide, and fluorocarbon gas. The composition of the present invention can be applied as an aerosol or by brushing or spray painting.
作用及び発明の効果
本発明組成物は、疎水性ジメチルシロキサン鎖を多く有
する縮合シリコン樹脂を含有するものであり、本発明の
縮合シリコン樹脂は直鎖のジメチルシロキサン鎖そのも
のであるシリコーンオイルに比べ、優れた着氷防止性を
示すと共に、アルコキシ基及び/又はシラノール基を有
しているため素地に対する付着性が優れ、着氷防止効果
の持続性に優れる。更に縮合シリコン樹脂に湿気硬化型
被膜形成樹脂及び必要に応じて(IV)式で表わされる
化合物を配合することによって被膜強度を向上し、着氷
防止効果を更に長期に持続さけることが可能である。Actions and Effects of the Invention The composition of the present invention contains a condensed silicone resin having a large number of hydrophobic dimethylsiloxane chains, and the condensed silicone resin of the present invention has a higher concentration than silicone oil, which is a linear dimethylsiloxane chain itself. It exhibits excellent anti-icing properties, and since it contains an alkoxy group and/or a silanol group, it has excellent adhesion to substrates and has an excellent long-lasting anti-icing effect. Furthermore, by blending the condensed silicone resin with a moisture-curable film-forming resin and, if necessary, a compound represented by formula (IV), it is possible to improve the film strength and maintain the anti-icing effect for an even longer period of time. .
実施例
以下、実施例を挙げて本発明をさらに具体的に説明する
。なお、以下「部」及び「%」は「重量部」及び「重量
%」を意味する。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples. Note that hereinafter "parts" and "%" mean "parts by weight" and "% by weight."
縮合シリコン樹脂液の製造
製造例1
〔式中、Xは平均約10の整数を示す。〕〔式中、Xは
平均約100の整数を示す。〕CH3CH2Cl−12
81(OCII3) 3 10部0.1規定塩
酸水溶液 4部キ シ し ン
50部メチル
イソブチルケトン 50部上記上記物をガ
ラス反応容器中で攪拌しながら85℃で3時間反応させ
、次いで120℃で2時間60部脱溶媒置換させなから
縮合を進め、重量平均分子曾約38000の縮合シリコ
ン樹脂Al液を得た。Production Example 1 of Condensed Silicone Resin Liquid [In the formula, X represents an integer of about 10 on average. [In the formula, X represents an integer with an average of about 100. ]CH3CH2Cl-12
81 (OCII3) 3 10 parts 0.1N aqueous hydrochloric acid solution 4 parts Xylene 50 parts Methyl isobutyl ketone 50 parts The above materials were reacted at 85°C for 3 hours with stirring in a glass reaction vessel, then at 120°C. Condensation was proceeded while removing and replacing 60 parts of the solvent for 2 hours to obtain a condensed silicone resin Al liquid having a weight average molecular weight of about 38,000.
製造例2
〔式中、Xは平均約25の整数を示す。〕オクチル酸錫
触媒 0.5部ト ル エ ン
100部上記上
記物をガラス反応容器中で攪拌しながら105℃で2時
間反応させ、更に2時間60部脱溶媒置換させなから縮
合を進め、重量平均分子間約47000の縮合シリコン
樹脂A2液を得た。Production Example 2 [wherein, X represents an integer with an average of about 25]. ] Tin octylate catalyst 0.5 parts Toluene 100 parts The above-mentioned materials were reacted at 105°C for 2 hours with stirring in a glass reaction vessel, and 60 parts were removed for another 2 hours to proceed with condensation without solvent displacement. A condensed silicone resin A2 liquid having a weight average molecular weight of about 47,000 was obtained.
製造例3
〔式中、Xは平均約50の整数を示す。〕OCH3Si
(OCH3) 3 20部0.1規定塩
酸水溶液 4部キ シ し ン
50部メチル
イソブチルケトン 50部上記上記物をガ
ラス反応容器中で攪拌しながら80℃で3時間反応させ
、次いで120℃で2時間60部脱溶媒置換させなから
縮合を進め、重量平均分子量的34000の縮合シリコ
ン樹脂A3液を得た。Production Example 3 [In the formula, X represents an integer of about 50 on average. ]OCH3Si
(OCH3) 3 20 parts 0.1N aqueous hydrochloric acid 4 parts Condensation was proceeded without solvent removal and substitution for 60 parts to obtain a condensed silicone resin liquid A3 having a weight average molecular weight of 34,000.
製造例4
〔式中、Xは平均約25の整数を示す。〕オクチル酸錫
触媒 0.5部ト ル エ ン
100部上記上
記物をガラス反応容器中で攪拌しながら105℃で2時
間反応させ、次いで同温度で2時間35部脱溶媒置換さ
せなから縮合を進め、重量平均分子量的27000の縮
合シリコン樹脂A4液を得た。Production Example 4 [wherein, X represents an integer with an average of about 25]. ] Tin octylate catalyst 0.5 parts Toluene 100 parts The above-mentioned materials were reacted at 105°C for 2 hours with stirring in a glass reaction vessel, and then 35 parts were removed at the same temperature for 2 hours before condensation. A condensed silicone resin A4 liquid having a weight average molecular weight of 27,000 was obtained.
製造例5
35部
〔式中、Xは平均約30の整数を示す。〕OCH35i
(OCTo ) 3 15部〔式中、X
は平均約10の整数を示す。〕0.1規定塩酸水溶液
5.5部キ シ し ン
50部メチルイソブチ
ルケトン 50部上記上記物をガラス反応
容器中で攪拌しながら83℃で3時間反応させ、次いで
120℃で2時間60部脱溶媒置換させなから縮合を進
め、重量平均分子量的20000の縮合シリコン樹脂A
5液を得た。Production Example 5 35 parts [wherein, X represents an integer with an average of about 30]. ]OCH35i
(OCTo) 3 15 parts [wherein, X
represents an integer with an average of about 10. ]0.1N hydrochloric acid aqueous solution
5.5 parts
50 parts Methyl isobutyl ketone 50 parts The above-mentioned material was reacted at 83°C for 3 hours with stirring in a glass reaction vessel, and then at 120°C for 2 hours 60 parts to proceed with condensation without removing the solvent and replacing the solvent with a weight average molecular weight of 20,000. condensed silicone resin A
5 liquids were obtained.
湿気硬化型被膜形成樹脂液の製造
製造例6
γ−メタクリルオキシプロピル
トリメトキシシラン 30部n−ブチ
ルアクリレート 20部メチルメタクリレ
ート 50部α、α −アゾビスイソブ
チロニトリル 1部キシレン30部、酢酸ブチル30部
及びn−ブチルアルコール15部をガラス製反応容器中
に仕込み、90℃に加熱、保持し、滴下ロートより上記
モノマーと触媒との混合物を4時間かけて滴下した。滴
下終了後、110℃に加熱、保持し、このものに、キシ
レン10部、酢酸ブチル10部、n−ブチルアルコール
5部及び2,2′ −アゾビス−2,4−ジメチルバレ
ロニトリル1部の混合物を滴下ロートより30分かけて
滴下し、滴下終了後110℃に1時間保持し、重量平均
分子量的36000のアルコキシシリル基含有アクリル
樹脂の固形分的50%の溶液を得た。Production of moisture-curable film-forming resin liquid Production Example 6 γ-methacryloxypropyltrimethoxysilane 30 parts n-butyl acrylate 20 parts Methyl methacrylate 50 parts α,α-azobisisobutyronitrile 1 part xylene 30 parts, butyl acetate 30 parts and 15 parts of n-butyl alcohol were charged into a glass reaction vessel, heated and maintained at 90°C, and the mixture of the above monomer and catalyst was added dropwise from the dropping funnel over 4 hours. After completion of the dropwise addition, the temperature was heated and maintained at 110°C, and a mixture of 10 parts of xylene, 10 parts of butyl acetate, 5 parts of n-butyl alcohol, and 1 part of 2,2'-azobis-2,4-dimethylvaleronitrile was added to the mixture. was added dropwise from a dropping funnel over a period of 30 minutes, and after the addition was completed, the temperature was maintained at 110° C. for 1 hour to obtain a solution of an alkoxysilyl group-containing acrylic resin having a weight average molecular weight of 36,000 and a solid content of 50%.
製造例7
γ−メタクリルオキシプロピル
メチルジメトキシシラン 50部t−ブチル
メタクリレート 40部ラウリルアクリレー
ト 10部α、α′ −アゾビスイソ
ブチロニトリル0.9部
キシレン38部及びn−ブチルアルコール37部をガラ
ス製反応容器中に仕込み、90℃に加熱、保持し、滴下
ロートより上記モノマーと触媒との混合物を4時間かけ
て滴下した。滴下終了後、110℃に加熱、保持し、こ
のものに、キシレン12部、n−ブチルアルコール13
部及び2゜2′−アゾビス−2,4−ジメチルバレロニ
トリル1部の混合物を滴下ロートより1時間かげて滴下
し、滴下終了後110℃に30分間保持し、重量平均分
子量的42000のアルコキシシリル基含有アクリル樹
脂の固形分約50%の溶液を得た。Production Example 7 γ-methacryloxypropylmethyldimethoxysilane 50 parts t-butyl methacrylate 40 parts lauryl acrylate 10 parts α,α'-azobisisobutyronitrile 0.9 parts 38 parts of xylene and 37 parts of n-butyl alcohol were added to a glass The mixture was charged into a reaction vessel made of aluminum, heated and maintained at 90°C, and the mixture of the monomer and catalyst was added dropwise from the dropping funnel over 4 hours. After dropping, heat and maintain at 110°C, add 12 parts of xylene and 13 parts of n-butyl alcohol.
A mixture of 1 part of 2゜2'-azobis-2,4-dimethylvaleronitrile was added dropwise from the dropping funnel over 1 hour, and after the addition was completed, the mixture was kept at 110°C for 30 minutes to form an alkoxysilyl with a weight average molecular weight of 42,000. A solution of about 50% solids of group-containing acrylic resin was obtained.
製造例8
アリルアクリレート 25部メチル
メタクリレート 30部n−ブチルアク
リレート 45部α、α′−アゾビスイソ
ブチロニトリル 1部キシレン40部及び酢酸ブチル4
0部をガラス製反応容器中に仕込み、90℃に加熱、保
持し、滴下ロートより上記モノマーと触媒との混合物を
4時間かけて滴下した。滴下終了後、90℃に保持した
まま、このものに、キシレン10部、酢酸ブチル10部
及び2,2′−アゾビス−2,4−ジメチルバレロニト
リル1部の混合物を30分かけて滴下し、滴下終了後9
0℃に1時間保持し、重量平均分子量約40000のア
クリル樹脂を得た。Production Example 8 Allyl acrylate 25 parts Methyl methacrylate 30 parts n-butyl acrylate 45 parts α,α'-Azobisisobutyronitrile 1 part Xylene 40 parts and butyl acetate 4 parts
0 part was charged into a glass reaction vessel, heated and maintained at 90°C, and the mixture of the monomer and catalyst was added dropwise from the dropping funnel over 4 hours. After completion of the dropwise addition, a mixture of 10 parts of xylene, 10 parts of butyl acetate, and 1 part of 2,2'-azobis-2,4-dimethylvaleronitrile was added dropwise to this mixture over 30 minutes while maintaining the temperature at 90°C. After completion of dripping 9
The mixture was kept at 0° C. for 1 hour to obtain an acrylic resin having a weight average molecular weight of about 40,000.
次いで得られた樹脂溶液を80°Cに保゛持し、このも
のに白金触媒0.4部、トリメトキシヒドロシラン28
部及びキシレン28部の混合物を3時間かけて滴下した
。滴下終了後、100℃に加熱保持し、白金触媒0.1
部を配合し2時間反応を行なってアルコキシシリル基含
有アクリル樹脂の固形分約50%の溶液を得た。Next, the obtained resin solution was maintained at 80°C, and 0.4 parts of platinum catalyst and 28 parts of trimethoxyhydrosilane were added to this solution.
A mixture of 1 part and 28 parts of xylene was added dropwise over 3 hours. After completing the dropping, heat and maintain at 100°C, add platinum catalyst 0.1
A solution of the alkoxysilyl group-containing acrylic resin with a solid content of about 50% was obtained by blending the two parts and reacting for 2 hours.
製造例9
無水フタル酸 32.1部トリメチ
ロールプロパン 14.1部ペンタエリスリト
ール 14.5部大豆油脂肪酸
46.2部上記混合物をガラス製反応容器中に
仕込み加熱攪拌した。180℃まで昇温した後、180
℃に1時間保ちエステル化反応を進めた。その後キシレ
ン5部を加え、230℃まで昇温した後、230°Cで
キシレンを還流させながら反応を進め、約4時間後酸価
(固形分)が15に達したところで反応を止めた。冷却
後キシレンを加え固形分濃度50%の樹脂溶液とした。Production Example 9 Phthalic anhydride 32.1 parts Trimethylolpropane 14.1 parts Pentaerythritol 14.5 parts Soybean oil fatty acid
46.2 parts of the above mixture was charged into a glass reaction vessel and heated and stirred. After raising the temperature to 180℃,
The mixture was kept at ℃ for 1 hour to advance the esterification reaction. Thereafter, 5 parts of xylene was added, the temperature was raised to 230°C, and the reaction was proceeded while refluxing the xylene at 230°C. After about 4 hours, the reaction was stopped when the acid value (solid content) reached 15. After cooling, xylene was added to obtain a resin solution with a solid content concentration of 50%.
得られた樹脂の重量平均分子量は約23000であった
。The weight average molecular weight of the obtained resin was about 23,000.
次いで得られた樹脂溶液を80℃に保持し、このものに
イソシアノエチルメタクリレート27部を配合し、イソ
シアネート基が実質的に存在しなくなるまで反応させた
。次いで、80℃に保持した反応物溶液中にトリメトキ
シヒドロシラン21.1部、白金触媒0,15部及びキ
シレン21部の混合物を3時間かけて滴下した。滴下終
了後、100℃に加熱、保持し、白金触媒を0.05部
配合し、2時間反応を行なってアルコキシシリル基含有
ポリエステル樹脂溶液を得た。Next, the obtained resin solution was maintained at 80° C., and 27 parts of isocyanoethyl methacrylate was added thereto, and the mixture was reacted until substantially no isocyanate groups were present. Next, a mixture of 21.1 parts of trimethoxyhydrosilane, 0.15 parts of platinum catalyst, and 21 parts of xylene was added dropwise into the reactant solution maintained at 80° C. over 3 hours. After completion of the dropwise addition, the mixture was heated and maintained at 100° C., 0.05 part of a platinum catalyst was added, and the reaction was carried out for 2 hours to obtain an alkoxysilyl group-containing polyester resin solution.
実施例1
製造例1で得た縮合
シリコン樹脂A1液 20部製造例6で
得たアクリル樹脂溶液 2部(TV)式のジメチ
ルシロキサン(a)(注1) 2部
シリコーンオイル(b)(注2)2.5部イソオクタン
40部エタノール
33.5部上記混合物100部を噴射剤
となるLPGガス200部と共に密閉容器に詰め、アル
ミ板に乾燥膜厚約5ミクロンとなるよう塗布し、24時
間室温で乾燥させた後、着氷力を測定した。その結果を
第2表に示す。Example 1 Condensed silicone resin A1 liquid obtained in Production Example 1 20 parts Acrylic resin solution obtained in Production Example 6 2 parts (TV) type dimethylsiloxane (a) (Note 1) 2 parts Silicone oil (b) (Note 2) 2.5 parts isooctane 40 parts ethanol
33.5 parts 100 parts of the above mixture was packed in a sealed container along with 200 parts of LPG gas as a propellant, and coated on an aluminum plate to a dry film thickness of approximately 5 microns. After drying at room temperature for 24 hours, the icing power was measured. The results are shown in Table 2.
(注1):化学式
〔式中、Xは平均的5の整数を示す。〕で表わされるジ
メチルシリコン。(Note 1): Chemical formula [wherein, X represents an average integer of 5]. ] Dimethyl silicone.
(注2):化学式
〔式中、Xは平均約8の整数を示す。〕で表わされるシ
リコーンオイル。(Note 2): Chemical formula [wherein, X represents an integer with an average of about 8]. ] Silicone oil.
実施例2〜9及び比較例1
第1表に示す配合とする以外は実施例1と同様に行ない
、着氷剪断破壊強度(kg/CI!12)を測定した。Examples 2 to 9 and Comparative Example 1 The same procedure as Example 1 was conducted except that the formulations shown in Table 1 were used, and the icing shear fracture strength (kg/CI!12) was measured.
結果を第2表に示す。The results are shown in Table 2.
なお第1表における(注3)、 (注5)は下記の通りである。In addition, (Note 3) in Table 1, (Note 5) is as follows.
(注3):化学式
〔式中、Xは平均約20の整数を示す。〕で表わされる
ジメチルシロキサン。(Note 3): Chemical formula [wherein, X represents an integer with an average of about 20]. ] Dimethylsiloxane.
(注4):化学式
〔式中、Xは平均約200の整数を示す。〕で表わされ
るシリコーンオイル。(Note 4): Chemical formula [wherein, X represents an integer with an average of about 200]. ] Silicone oil.
(注5):化学式
で表わされる粘度約1000ストークス(25℃)のシ
リコーンオイルであって、式中、Xは平均約1000程
度の整数である。(Note 5): A silicone oil with a viscosity of about 1000 Stokes (25°C) expressed by the chemical formula, where X is an integer with an average of about 1000.
また、第2表における(注6)、(注7)及び(注8)
の試験方法は下記の方法に従って行なった。Also, (Note 6), (Note 7) and (Note 8) in Table 2
The test method was conducted according to the following method.
(注6)@氷剪断破壊強度試験方法:
試験板(着氷防止組成物が塗布、乾燥されたアルミニウ
ム板)上にステンレス製リング(内面積5cm2)を置
き、これを−10°Cの冷凍試験恒温槽の中に入れ、9
0分間予備冷却する。次いで5°Cに保たれた蒸留脱イ
オン水2mQをステンレス製リング中に注ぎ氷結させる
ことにより被験体表面に接着した氷を得る。このものを
−10°Cで2時間この状態に放置した後、ロードセル
に連結され、動力によって駆動する金属製作動棒によっ
てリングに力を加えて、接着した氷を剥離させるときの
剪断破壊強度を測定した(単位: kg/cm2)。(Note 6) @Ice shear fracture strength test method: A stainless steel ring (inner area 5 cm2) was placed on the test plate (aluminum plate coated with anti-icing composition and dried) and frozen at -10°C. Place it in a test thermostat, 9
Precool for 0 minutes. Next, 2 mQ of distilled deionized water kept at 5°C is poured into the stainless steel ring to freeze it, thereby obtaining ice that adheres to the surface of the subject. After this thing was left in this state for 2 hours at -10°C, force was applied to the ring by a metal moving rod connected to a load cell and driven by power, and the shear fracture strength when peeling off the adhered ice was measured. It was measured (unit: kg/cm2).
(注7)繰返しテスト:
(注6)の試験を試験板の同一箇所について繰返し行な
った時の着氷剪断破壊強度を測定し、10.20.30
.40及び50回目の値を記載した。(Note 7) Repeated test: The icing shear fracture strength was measured when the test in (Note 6) was repeated on the same location on the test plate, and 10.20.30
.. The 40th and 50th values are listed.
(注8)屋外バクロテスト:
神奈川県平塚市において傾斜角35°で南向きに試験板
を暴露し、暴露2.4.8及び12週間の試験板につい
て(注6)の試験を行なった。(Note 8) Outdoor Bacro test: The test board was exposed to the south at an inclination angle of 35° in Hiratsuka City, Kanagawa Prefecture, and the test (Note 6) was conducted on the test board after exposure for 2, 4, 8 and 12 weeks.
また着氷剪断破壊強度はテストされていない初期の試験
板についても測定した。Icing shear failure strength was also measured on initial test plates that had not been tested.
第2表の試験結果から明らかなように、本発明による着
氷防止剤を塗布した表面は氷の固着力が小さい。このよ
うな効果は、エアゾール噴射によって塗布した場合だけ
ではな(、噴射剤を除いた配合で、ハケやエアスプレー
などによって塗布した場合も同様な結果を示した。As is clear from the test results in Table 2, the surface coated with the anti-icing agent of the present invention has a low ice adhesion force. Such an effect is not only seen when applied by aerosol spraying (similar results were also shown when applied with a brush or air spray with a formulation that does not contain a propellant).
また、実施例6の組成物に比べ、湿気硬化型被膜形成樹
脂を配合した、実施例6以外の実施例の組成物は、より
長期間の着氷防止効果を示した。Moreover, compared to the composition of Example 6, the compositions of Examples other than Example 6, which were blended with a moisture-curable film-forming resin, exhibited a longer-term icing prevention effect.
(以 上)(that's all)
Claims (1)
酸素原子、エチレン基又は1,3−プロピレン基を示し
、aは5〜150の整数、b及びeは同一又は異なる1
〜3の整数を示し、cは3−b、dは3−eの整数を示
す。〕 で表わされるアルコキシジメチルシロキサン化合物を縮
合して得られるか、或いは該一般式( I )の化合物と
一般式 (R_3)i−Si−(OR_2)j(II)〔式中、R
_2はメチル基又はエチル基を示し、R_3は炭素数1
〜8のアルキル基を示し、iは0〜3の整数、jは4−
iを示す。〕 で表わされるアルコキシシラン化合物及び/又は一般式 ▲数式、化学式、表等があります▼(III) 〔式中、kは10〜200の整数を示す。〕で表わされ
るジヒドロキシジメチルシロキサン化合物との混合物を
共縮合して得られるシリコン樹脂を含有することを特徴
とする着氷防止組成物。 [2]湿気硬化型被膜形成樹脂を含有する請求項1記載
の着氷防止組成物。 [3]一般式 ▲数式、化学式、表等があります▼(IV) 〔式中、R_3及びR_4は同一又は異なってメチル基
又はエチル基を示し、D及びEは同一又は異なって酸素
原子、エチレン基又は1,3−プロピレン基を示す。X
は3〜30の整数を示し、又、m及びrは同一又は異な
って1〜3の整数を示し、nは3−m、Sは3−rを示
す。〕 で表わされる両末端アルコキシシリル基含有ジメチルシ
ロキサン化合物を含有する請求項2記載の着氷防止組成
物。 [4]一般式 ▲数式、化学式、表等があります▼(V) 〔式中、yは1〜20000の整数を示す。〕で表わさ
れるシリコーンオイルを含有する請求項1〜3のいずれ
かに記載の着氷防止組成物。 [5]請求項1〜4記載のいずれかの着氷防止組成物を
噴射ガス剤を媒体とするエアロゾルとして塗布する着氷
防止方法。[Claims] [1] General formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) [In the formula, R_1 represents a methyl group or an ethyl group, and A represents an oxygen atom, an ethylene group, or a 1,3- represents a propylene group, a is an integer of 5 to 150, b and e are the same or different 1
Indicates an integer of ~3, c indicates an integer of 3-b, and d indicates an integer of 3-e. ] or obtained by condensing an alkoxydimethylsiloxane compound represented by the formula (I), or a compound of the general formula (I) and the general formula (R_3)i-Si-(OR_2)j(II) [wherein R
_2 represents a methyl group or an ethyl group, R_3 has 1 carbon number
~8 alkyl group, i is an integer of 0 to 3, j is 4-
Indicates i. ] Alkoxysilane compound and/or general formula represented by ▲ Numerical formula, chemical formula, table, etc. ▼ (III) [In the formula, k represents an integer from 10 to 200. An anti-icing composition characterized by containing a silicone resin obtained by co-condensing a mixture with a dihydroxydimethylsiloxane compound represented by the following. [2] The anti-icing composition according to claim 1, which contains a moisture-curable film-forming resin. [3] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (IV) [In the formula, R_3 and R_4 are the same or different and represent a methyl group or ethyl group, and D and E are the same or different and represent an oxygen atom, ethylene group or 1,3-propylene group. X
represents an integer of 3 to 30, m and r are the same or different and represent an integer of 1 to 3, n represents 3-m, and S represents 3-r. ] The anti-icing composition according to claim 2, which contains a dimethylsiloxane compound containing an alkoxysilyl group at both terminals. [4] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (V) [In the formula, y represents an integer from 1 to 20,000. The anti-icing composition according to any one of claims 1 to 3, which contains a silicone oil represented by the following. [5] An icing prevention method comprising applying the icing prevention composition according to any one of claims 1 to 4 as an aerosol using a propellant gas agent as a medium.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30350788A JPH02147688A (en) | 1988-11-29 | 1988-11-29 | Icing-preventive composition |
DE19893939482 DE3939482C2 (en) | 1988-11-29 | 1989-11-29 | De-icing and anti-icing method |
US07/790,088 US5188750A (en) | 1988-11-29 | 1991-11-13 | Anti-icing composition and method of preventing icing |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30350788A JPH02147688A (en) | 1988-11-29 | 1988-11-29 | Icing-preventive composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH02147688A true JPH02147688A (en) | 1990-06-06 |
Family
ID=17921804
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP30350788A Pending JPH02147688A (en) | 1988-11-29 | 1988-11-29 | Icing-preventive composition |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPH02147688A (en) |
DE (1) | DE3939482C2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002256218A (en) * | 2001-03-02 | 2002-09-11 | Mitsunori Yoshida | Composition for preventing snow and ice accretion and member for preventing snow and ice accretion using the same |
WO2019013207A1 (en) * | 2017-07-12 | 2019-01-17 | イムラ・ジャパン株式会社 | Nonfreezing composition and nonfreezing polymer |
WO2020031300A1 (en) * | 2018-08-08 | 2020-02-13 | 日立化成株式会社 | Snow-ice accretion preventing agent, snow-ice accretion prevention structure, and production method for snow-ice accretion prevention structure |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4113554A1 (en) * | 1991-04-25 | 1992-10-29 | Wacker Chemie Gmbh | ORGANO (POLY) SILOXANS, THEIR PRODUCTION AND USE |
US5685506A (en) * | 1995-03-31 | 1997-11-11 | General Electric Company | Insect abatement system |
WO2005118721A1 (en) * | 2004-04-16 | 2005-12-15 | University Of Washington | Method for rapid crosslinking of silicone compounds by in situ water generation |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4636324A (en) * | 1984-03-30 | 1987-01-13 | Kansai Paint Company, Ltd. | Anti-icing compositions |
DE3535283A1 (en) * | 1985-10-03 | 1987-04-09 | Byk Chemie Gmbh | POLYSILOXANES CONTAINING POLYESTER GROUPS FOR VARNISHES AND MOLDS AND THE USE THEREOF |
DE3541100A1 (en) * | 1985-11-21 | 1987-05-27 | Bayer Ag | USE OF SILICONE MATERIALS TO PREVENT ICING ON SUBSTRATES |
DE3817953C1 (en) * | 1988-05-27 | 1989-05-11 | Vegla Vereinigte Glaswerke Gmbh, 5100 Aachen, De |
-
1988
- 1988-11-29 JP JP30350788A patent/JPH02147688A/en active Pending
-
1989
- 1989-11-29 DE DE19893939482 patent/DE3939482C2/en not_active Expired - Fee Related
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002256218A (en) * | 2001-03-02 | 2002-09-11 | Mitsunori Yoshida | Composition for preventing snow and ice accretion and member for preventing snow and ice accretion using the same |
WO2019013207A1 (en) * | 2017-07-12 | 2019-01-17 | イムラ・ジャパン株式会社 | Nonfreezing composition and nonfreezing polymer |
JP2019019167A (en) * | 2017-07-12 | 2019-02-07 | イムラ・ジャパン株式会社 | Non-icing composition and non-icing polymer |
WO2020031300A1 (en) * | 2018-08-08 | 2020-02-13 | 日立化成株式会社 | Snow-ice accretion preventing agent, snow-ice accretion prevention structure, and production method for snow-ice accretion prevention structure |
JPWO2020031300A1 (en) * | 2018-08-08 | 2021-08-02 | 昭和電工マテリアルズ株式会社 | Manufacturing method of snow ice prevention agent, snow ice prevention structure, snow ice prevention structure |
Also Published As
Publication number | Publication date |
---|---|
DE3939482A1 (en) | 1990-05-31 |
DE3939482C2 (en) | 1998-07-09 |
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