JP6285518B2 - 不飽和基を含むオルガノポリシロキサン - Google Patents
不飽和基を含むオルガノポリシロキサン Download PDFInfo
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- JP6285518B2 JP6285518B2 JP2016189368A JP2016189368A JP6285518B2 JP 6285518 B2 JP6285518 B2 JP 6285518B2 JP 2016189368 A JP2016189368 A JP 2016189368A JP 2016189368 A JP2016189368 A JP 2016189368A JP 6285518 B2 JP6285518 B2 JP 6285518B2
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- polyolefin
- polyorganosiloxane
- bond
- formula
- Prior art date
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- 229920001296 polysiloxane Polymers 0.000 title claims description 19
- -1 siloxane units Chemical group 0.000 claims description 116
- 229920000098 polyolefin Polymers 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 66
- 239000004743 Polypropylene Substances 0.000 claims description 48
- 229920001155 polypropylene Polymers 0.000 claims description 43
- 150000003254 radicals Chemical class 0.000 claims description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 239000000945 filler Substances 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 229910021419 crystalline silicon Inorganic materials 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229910021485 fumed silica Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- 150000003377 silicon compounds Chemical class 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 claims description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011324 bead Substances 0.000 claims description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims description 3
- 235000007164 Oryza sativa Nutrition 0.000 claims description 3
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 3
- 239000002956 ash Substances 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 239000010903 husk Substances 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 235000009566 rice Nutrition 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052582 BN Inorganic materials 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical group O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004113 Sepiolite Substances 0.000 claims description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 239000005083 Zinc sulfide Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052586 apatite Inorganic materials 0.000 claims description 2
- 229960000892 attapulgite Drugs 0.000 claims description 2
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 claims description 2
- 229910002113 barium titanate Inorganic materials 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000000378 calcium silicate Substances 0.000 claims description 2
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 239000004568 cement Substances 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000010459 dolomite Substances 0.000 claims description 2
- 229910000514 dolomite Inorganic materials 0.000 claims description 2
- 239000010433 feldspar Substances 0.000 claims description 2
- 239000010881 fly ash Substances 0.000 claims description 2
- 239000005350 fused silica glass Substances 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052982 molybdenum disulfide Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 2
- 229910052625 palygorskite Inorganic materials 0.000 claims description 2
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 claims description 2
- 239000010451 perlite Substances 0.000 claims description 2
- 235000019362 perlite Nutrition 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000008262 pumice Substances 0.000 claims description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 claims description 2
- 239000010453 quartz Substances 0.000 claims description 2
- 239000004576 sand Substances 0.000 claims description 2
- 229910052624 sepiolite Inorganic materials 0.000 claims description 2
- 235000019355 sepiolite Nutrition 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 239000010454 slate Substances 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 239000010455 vermiculite Substances 0.000 claims description 2
- 229910052902 vermiculite Inorganic materials 0.000 claims description 2
- 235000019354 vermiculite Nutrition 0.000 claims description 2
- 239000010456 wollastonite Substances 0.000 claims description 2
- 229910052882 wollastonite Inorganic materials 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 229910052984 zinc sulfide Inorganic materials 0.000 claims description 2
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 claims description 2
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 claims description 2
- 229910000859 α-Fe Inorganic materials 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229910052788 barium Inorganic materials 0.000 claims 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 235000002918 Fraxinus excelsior Nutrition 0.000 claims 1
- 150000001638 boron Chemical class 0.000 claims 1
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 239000000779 smoke Substances 0.000 claims 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 claims 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 45
- 239000004205 dimethyl polysiloxane Substances 0.000 description 44
- 125000003118 aryl group Chemical group 0.000 description 43
- 230000000694 effects Effects 0.000 description 33
- 229920000642 polymer Polymers 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 28
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 27
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 19
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 229920000573 polyethylene Polymers 0.000 description 15
- 239000004698 Polyethylene Substances 0.000 description 14
- 229910008051 Si-OH Inorganic materials 0.000 description 14
- 229910006358 Si—OH Inorganic materials 0.000 description 14
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 14
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
- 239000000835 fiber Substances 0.000 description 11
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- 150000002978 peroxides Chemical class 0.000 description 10
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- 239000003054 catalyst Substances 0.000 description 9
- 230000004580 weight loss Effects 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000012752 auxiliary agent Substances 0.000 description 7
- 238000010894 electron beam technology Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229920002959 polymer blend Polymers 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 6
- 239000002023 wood Substances 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- OZZYKXXGCOLLLO-TWTPFVCWSA-N ethyl (2e,4e)-hexa-2,4-dienoate Chemical group CCOC(=O)\C=C\C=C\C OZZYKXXGCOLLLO-TWTPFVCWSA-N 0.000 description 5
- 229920001112 grafted polyolefin Polymers 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
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- 229910000077 silane Inorganic materials 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
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- 150000001412 amines Chemical class 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 229940075582 sorbic acid Drugs 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
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- 229920005629 polypropylene homopolymer Polymers 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
Description
欧州特許第1022302号公報には、シラノール基を重合可能なエチレン性不飽和基を含むアルコキシシランと反応させるための触媒系が開示されている。この触媒系は、有機リチウム試薬及びヒドロキシアミンを含む。
C−Si結合及びSi−O−Si結合は、Si−O−C結合よりも加水分解的に安定である。
・ポリオルガノシロキサンは、2〜2000のシロキサン単位を含み、シロキサン単位の少なくとも90モル%がD単位であるのが好ましい。
・ポリオルガノシロキサンは、式−X−CH=CH−R”(I)または−X−C≡C−R”(II)の少なくとも1つの末端基を有するポリジメチルシロキサンであるのが好ましい。
・ポリオルガノシロキサンは、ポリジオルガノシロキサン分子の両端に式−X−CH=CH−R”(I)または−X−C≡C−R”(II)の末端基を有する直鎖状ポリジオルガノシロキサンであるのが好ましい。
・ポリオルガノシロキサンは、式−X−CH=CH−R”(I)または−X−C≡C−R”(II)の少なくとも1つのペンダント基を有するのが好ましい。
・式−X−CH=CH−R”(I)または−X−C≡C−R”(II)の基は、C−Si結合によりポリオルガノシロキサンに結合しているのが好ましい。
・式−X−CH=CH−R”(I)の基は、アクリルオキシアルキル基であるのが好ましい。
・助剤は、ビニル芳香族化合物であるのが好ましく、好適にはスチレンまたはソルビン酸エステル、好適にはソルビン酸エチルである。
・助剤は、全組成の0.1〜15.0重量%で存在するのが好ましい。
・式−X−CH=CH−R”(I)または−X−C≡C−R”(II)の基は、式CH2=CH−C6H4−A−(III)またはCH≡C−C6H4−A−(IV)(式中のAは直接結合または1〜12の炭素原子を有する二価の有機基を表し、任意に−O−、−S−及び−NH−から選択される二価のヘテロ原子の連結基を含む)を有するのが好ましい。
・式−X−CH=CH−R”(I)の基は、式R2−CH=CH−CH=CH−X−(V)(式中のR2は水素または1〜12の炭素原子を有するヒドロカルビル基を表す)を有するのが好ましい。
・式−X−CH=CH−R”(I)の基は、ソルビルオキシ基であるのが好ましい。
・組成物は、1〜99重量%のポリオレフィン及び99〜1重量%のポリオルガノシロキサンを含むのが好ましく、5〜95重量%のポリオレフィン及び95〜5重量%のポリオルガノシロキサンを含むのがより好ましい。
・フリーラジカルサイトをポリオレフィンにもたらし得る有機過酸化化合物は、全組成の0.01〜2重量%で存在するのが好ましい。
・好適には、本発明はポリオルガノシロキサンの製造方法を提供するもので、シロキサン単位の少なくとも50モル%が本明細書で定義するD単位であり、少なくとも1つのSi−OH基を含むポリオルガノシロキサンを、式−X−CH=CH−R”(I)または−X−C≡C−R”(II)の不飽和基を含むアルコキシシランと反応させることを特徴とする。
・好適には、本発明はフリーラジカルサイトをポリオレフィンにもたらし得る手段の存在下ポリオレフィンを不飽和基を含むケイ素化合物と反応させる工程を備えるシリコーンをポリオレフィンにグラフトする方法を提供するもので、該ケイ素化合物はシロキサン単位の少なくとも50モル%が本明細書で定義するD単位であり、少なくとも1つの不飽和基を含むポリオルガノシロキサンであることを特徴とし、また前記不飽和基が式−X−CH=CH−R”(I)または−X−C≡C−R”(II)(式中のXは−CH=CH−結合若しくは−C≡C−結合に対して電子求引効果を有し、及び/または芳香族環若しくは追加的なオレフィンの二重結合若しくはアセチレン不飽和を含む二価の有機結合を表し、前記芳香族環若しくは追加的なオレフィンの二重結合若しくはアセチレン不飽和は−X−CH=CH−R”のオレフィン不飽和または−X−C≡C−R”のアセチレン不飽和と共役し、またR”は水素または−CH=CH−結合若しくは−C≡C−結合に対して電子求引効果若しくは任意の他の活性化効果を有する基を表す)の基であることを特徴とする。
・式−X−CH=CH−R”(I)または−X−C≡C−R”(II)の少なくとも1つの基を含むポリオルガノシロキサンを、ポリオレフィンと反応させる前に充填剤上に堆積させるのが好ましい。
・式−X−CH=CH−R”(I)または−X−C≡C−R”(II)の少なくとも1つの基を含むポリオルガノシロキサンと充填剤とを、現場で反応させるのが好ましい。
使用したポリマーは以下の通りとした。
・PP=Borealis(登録商標)HB 205 TFとして供給されるイソタクチックポリプロピレンのホモポリマー(メルトフローインデックスMFRは、ISO1133に従って測定して230℃/2.16kgで1g/10分)
・PPH=PPH 7060としてTotal Petrochemicals(登録商標)により販売されるポリプロピレンのホモポリマー(MFRは、230℃/2.16kgで12g/10分);多孔性PPは、Accurel(登録商標)XP100としてMembranaにより提供される微孔性ポリプロピレンであった。この微孔性ポリマーを液体成分の吸収のために用いた。Accurel(登録商標)XP100の特性として、MFR(2.16kg/230℃)は2.1g/10分(ISO1133の方法)、融点(DSC)は156℃である。
・木粉=American Wood Fibers(登録商標)により販売される松の木粉。
・MAg−PP=Orevac(登録商標)CA100、Arkema(登録商標)により販売される無水マレイン酸ポリプロピレン(MFRは230℃/2.16kgで150〜200g/10分)。
・DHBPは、Arkema Luperox(登録商標)101 の過酸化物として販売される2.5−ジメチル−2,5−ジ−(tert−ブチルペルオキシ)ヘキサンペルオキサイドであった。
・スチレンは、Sigma−Aldrich Reagent Plus(登録商標)により販売される純度99%以上のものであった(ref.S4972)。
・ソルビン酸エチルは、Sigma−Aldrich Reagent Plus(登録商標)により供給される純度98%以上のものであった(ref.177687)。
・nの値が様々、すなわち様々な重合度(DP)であるα、ω−ジ−ヒドロキシ官能化ポリジメチルシロキサン HO−[Si(Me2)−O]n−Hは、Dow Corning(登録商標)から内部的に供給された。
・Irgafos 168は、Irgafos(登録商標)168としてCibaにより供給されるトリス−(2,4−ジ−tert−ブチルフェニル)ホスファイトの酸化防止剤であった。
・Irganox 1010は、Irganox(登録商標) 1010としてCibaにより供給されるテトラキス[メチレン−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル−プロピオナート)]のメタンフェノール系酸化防止剤であった。
DP=4のヒドロキシ末端ポリジメチルシロキサン(ヒドロキシ−PDMS)を等モル量(ヒドロキシ官能基のモル量に対し)のソルビルオキシプロピルトリメトキシシランと反応させることにより、α,ω−ジ−ソルビルオキシプロピルシリケート官能性ポリジメチルシロキサン(ソルベート−PDMS)Me−CH=CH−CH=CH−(C=O)−O−(CH2)3−Si(OMe)2−O−[Si(Me2)−O]n−Si(OMe)2−(CH2)3−O−(C=O)−CH=CH−CH=CH−Me(式中、n=4である)を調製した。これら材料を窒素下で数分間撹拌し、次いで2gのチタンn−ブトキシドを撹拌下で加えた。生成物が完全に均質になるまで混合を続けた。形成したポリマー生成物の特性から、鎖グループ構造−SiR(OR’)2(式中のRはソルビルオキシプロピルであり、R’はそれぞれメチルである)を有するソルビルオキシプロピルシリケート官能性ポリジメチルシロキサンの形成が裏付けられた。
対応するDPのヒドロキシ末端ポリジメチルシロキサンから実施例1の方法により、表1に示すように様々なシロキサン鎖長を有するソルベート−PDMSを調製した。
DP=12のヒドロキシ末端ポリジメチルシロキサンを等モル量(ヒドロキシ官能基のモル量に対し)のアクリルオキシプロピルトリメトキシシラン(Dow Corning(登録商標)Z−6530)と反応させることにより、α,ω−ジ−アクリルオキシプロピルシリケート官能化ポリジメチルシロキサン(アクリレート−PDMS)H2C=CH−(C=O)−O−(CH2)3−Si(OMe)2−O−[Si(Me2)−O]n−Si(OMe)2−(CH2)3−O−(C=O)−CH2(式中、n=12である)を調製した。これら材料を窒素下数分間撹拌し、次いで2gのチタンn−ブトキシドを撹拌下で加えた。生成物が完全に均質になるまで混合を続けた。形成したポリマー生成物の特性から、鎖グループ構造−SiR(OR’)2(式中のRはアクリルオキシであり、R’はそれぞれメチルである)を有するアクリルオキシプロピルシリケート官能性ポリジメチルシロキサンの形成が裏付けられた。
表2に示すように、n=12のアクリレート−PDMSと等モル比で異なるラジカル安定化助剤を加えて実施例6を繰り返した。
表3に示すように、DP=12のヒドロキシ−PDMSを同量の比較例C3〜C5の各ヒドロキシ−PDMSに置き換えて比較例2を繰り返した。
表4における処方に従い、ポリプロピレン及び25重量%の木粉を含む実施例1のn=4であるソルベート−PDMSの化合物を調製した。
表4における処方に従い、ポリプロピレン及び25重量%の木粉を含む実施例2のn=12であるソルベート−PDMSの化合物を調製した。実施例11におけるソルベート−PDMSの量は、実施例10におけるソルベート官能基と等モルの量である。
表4に示すように、γ−ATM、ソルベート−PDMS及びDHBPを省き、実施例1を繰り返した。
表4に示すように、MAg−PPを加えて比較例C7を繰り返した。
・T1=180℃
・T2=180℃
・T3=190℃
・T4=190℃
・T5=190℃
・T6=180℃
Claims (13)
- ポリオレフィンと、シロキサン単位の少なくとも50モル%がR2SiO2/2(D単位、式中の各Rは有機基、水素またはヒドロキシル基を表す)であるポリオルガノシロキサンとを含む組成物であって、
前記ポリオルガノシロキサンが、前記ポリオルガノシロキサン中の式
CH 3 −CH=CH−CH=CH−C(=O)O−R * (I)
(式中のR *はアルキレン基を表す)
のソルビルオキシアルキル基のフリーラジカル重合によって形成された結合により少なくとも部分的に前記ポリオレフィンにグラフトされていることを特徴とする、組成物。 - 前記ソルビルオキシアルキル基が、式CH3−CH=CH−CH=CH−C(=O)O−(CH2)3−のソルビルオキシプロピル基であることを特徴とする、請求項1に記載の組成物。
- 前記ポリオレフィンが、ポリプロピレンである、請求項1に記載の組成物。
- 前記ソルビルオキシアルキル基が、C−Si結合により前記ポリオルガノシロキサンに結合していることを特徴とする、請求項1に記載の組成物。
- 前記ポリオルガノシロキサンが、ポリジオルガノシロキサン分子の両端に末端ソルビルオキシアルキル基を有する直鎖状ポリジオルガノシロキサンであることを特徴とする、請求項4に記載の組成物。
- 前記ポリオルガノシロキサンが、少なくとも1つのペンダントソルビルオキシアルキル基を有することを特徴とする、請求項4に記載の組成物。
- 前記ポリオルガノシロキサンが2〜2000のシロキサン単位を含み、該シロキサン単位の少なくとも90モル%がD単位であることを特徴とする、請求項1に記載の組成物。
- 前記組成物が、充填剤をさらに含むことを特徴とする、請求項1に記載の組成物。
- 前記充填剤が、三水酸化アルミニウム、二水酸化マグネシウム、カオリン;無水和、部分水和若しくは水和の、ナトリウム、カリウム、マグネシウム、カルシウム又はバリウムのフッ化物、塩化物、臭化物、ヨウ化物、クロム酸塩、水酸化物、リン酸塩、リン酸水素塩、硝酸塩、酸化物又は硫酸塩;酸化亜鉛、酸化アルミニウム、五酸化アンチモン、三酸化アンチモン、酸化ベリリウム、酸化クロム、酸化鉄、リトポン、ホウ酸またはホウ酸塩、ホウ酸亜鉛、メタホウ酸バリウム若しくはホウ酸アルミニウム、混合金属酸化物、アルミノケイ酸塩、バーミキュライト;ヒュームドシリカ、溶融シリカ、沈殿シリカ、石英、砂又はシリカゲルを含むシリカ;もみ殻灰、セラミックビーズ、ガラスビーズ、ゼオライト、アルミニウムのフレーク若しくは粉末、ブロンズ粉、モリブデン、ニッケル、ステンレス鋼の粉、タングステン、水和ケイ酸カルシウム、チタン酸バリウム、シリカ−カーボンブラック複合物、セメント、フライアッシュ、スレート粉、ベントナイト、クレイ、タルク、無煙灰、リン灰石、アタパルジャイト、窒化ホウ素、クリストバライト、珪藻土、ドロマイト、フェライト、長石、黒鉛、焼成カオリン、二硫化モリブデン、パーライト、軽石、パイロフィライト、セピオライト、スズ酸亜鉛、硫化亜鉛または珪灰石を含むことを特徴とする、請求項8に記載の組成物。
- フリーラジカルサイトを前記ポリオレフィンにもたらし得る有機過酸化化合物を、全組成物の0.01〜2重量%さらに含むことを特徴とする、請求項1に記載の組成物。
- ポリオレフィンを、不飽和基を含むケイ素化合物と、フリーラジカルサイトを前記ポリオレフィンにもたらし得る手段の存在下で反応させる工程を備える、シリコーンをポリオレフィンへグラフトする方法あって、
前記ケイ素化合物は、シロキサン単位の少なくとも50モル%がR2SiO2/2(D単位、式中の各Rは有機基、水素またはヒドロキシル基を表す)であり、少なくとも1つの不飽和基を含むポリオルガノシロキサンであることを特徴とし、また前記不飽和基が式
CH 3 −CH=CH−CH=CH−C(=O)O−R * (I)
(式中のR *はアルキレン基を表す)
のソルビルオキシアルキル基であることを特徴とする、方法。 - 前記少なくとも1つの不飽和基を含むポリオルガノシロキサンを、前記ポリオレフィンと反応させる前に充填剤上に堆積させることを特徴とする、請求項11に記載の方法。
- 前記ポリオレフィンと、前記少なくとも1つの不飽和基を含むポリオルガノシロキサンと、充填剤とを現場で反応させることを特徴とする、請求項11に記載の方法。
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