JP2021515059A - 硬化性オルガノポリシロキサン組成物 - Google Patents
硬化性オルガノポリシロキサン組成物 Download PDFInfo
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- JP2021515059A JP2021515059A JP2020540536A JP2020540536A JP2021515059A JP 2021515059 A JP2021515059 A JP 2021515059A JP 2020540536 A JP2020540536 A JP 2020540536A JP 2020540536 A JP2020540536 A JP 2020540536A JP 2021515059 A JP2021515059 A JP 2021515059A
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- methacrylate
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- 239000000203 mixture Substances 0.000 title claims abstract description 170
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 27
- 239000000945 filler Substances 0.000 claims abstract description 85
- -1 siloxane units Chemical group 0.000 claims abstract description 64
- 229920005989 resin Polymers 0.000 claims abstract description 38
- 239000011347 resin Substances 0.000 claims abstract description 38
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- 239000003999 initiator Substances 0.000 claims abstract description 23
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 10
- 239000000835 fiber Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 150000002430 hydrocarbons Chemical group 0.000 claims description 18
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- 238000000465 moulding Methods 0.000 claims description 7
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- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 3
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- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 9
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- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 6
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 5
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- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 4
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- BTLPDSCJUZOEJB-UHFFFAOYSA-N triethoxy(2-triethoxysilylethenyl)silane Chemical compound CCO[Si](OCC)(OCC)C=C[Si](OCC)(OCC)OCC BTLPDSCJUZOEJB-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- UWSYCPWEBZRZNJ-UHFFFAOYSA-N trimethoxy(2,4,4-trimethylpentyl)silane Chemical compound CO[Si](OC)(OC)CC(C)CC(C)(C)C UWSYCPWEBZRZNJ-UHFFFAOYSA-N 0.000 description 1
- JPMBLOQPQSYOMC-UHFFFAOYSA-N trimethoxy(3-methoxypropyl)silane Chemical compound COCCC[Si](OC)(OC)OC JPMBLOQPQSYOMC-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- PTVDYMGQGCNETM-UHFFFAOYSA-N trityl 2-methylprop-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C(=C)C)C1=CC=CC=C1 PTVDYMGQGCNETM-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L83/04—Polysiloxanes
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- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B20/00—Use of materials as fillers for mortars, concrete or artificial stone according to more than one of groups C04B14/00 - C04B18/00 and characterised by shape or grain distribution; Treatment of materials according to more than one of the groups C04B14/00 - C04B18/00 specially adapted to enhance their filling properties in mortars, concrete or artificial stone; Expanding or defibrillating materials
- C04B20/0048—Fibrous materials
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- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/12—Nitrogen containing compounds organic derivatives of hydrazine
- C04B24/121—Amines, polyamines
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/30—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Other silicon-containing organic compounds; Boron-organic compounds
- C04B26/32—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Other silicon-containing organic compounds; Boron-organic compounds containing silicon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/10—Reinforcing macromolecular compounds with loose or coherent fibrous material characterised by the additives used in the polymer mixture
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/101—Esters; Ether-esters of monocarboxylic acids
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/544—Silicon-containing compounds containing nitrogen
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Abstract
Description
(A)一般式
RaR1 b(OR2)cSiO(4−a−b−c)/2(I)、
の単位からなるオルガノポリシロキサン樹脂、
式中、
Rは同じであるか、又は異なっていてもよく、水素原子又は脂肪族炭素−炭素多重結合を含まない、一価のSiC結合の任意に置換される炭化水素基であり、
R1は同じであるか、又は異なっていてもよく、脂肪族炭素−炭素多重結合を有する、一価のSiC結合の任意に置換される炭化水素基であり、
R2は同じであるか、又は異なっていてもよく、水素原子又は一価の任意に置換される炭化水素基であり、
aは0、1、2、又は3であり、
bは0又は1であり、及び
cは0、1、2、又は3であり、
ただし、それぞれの場合に、オルガノポリシロキサン樹脂(A)中の式(I)のすべてのシロキサン単位に基づいて、式(I)においてa+b+cの合計は≦3であり、式(I)の少なくとも1つの単位においてb=1であり、式(I)の単位の少なくとも50%、好ましくは少なくとも60%、特に好ましくは少なくとも80%、特に少なくとも90%においてa+b=1であり、及び式(I)の単位の最大10%、好ましくは最大8%、特に好ましくは最大6%においてa+b=3であり、
(B)式
CR3 2=CR3−CO−Z−(II)、
の少なくとも1つの単位を有する有機化合物、
式中、
R3は同じであるか、又は異なっていてもよく、水素原子、シアノ基−CN又はヘテロ原子によって中断され得る一価の任意に置換される炭化水素基であり、
Zは同じであるか、又は異なっていてもよく、−O−又は−NR5−であり、
及び
R5は同じであるか、又は異なっていてもよく、水素原子又はヘテロ原子によって中断され得る一価の任意に置換される炭化水素基であり、
(C)開始剤、
(D)充填剤並びに
(K)アミン
を含む組成物に関する。
特に好ましくは1〜8個の炭素原子を有するアルキル又はアリール基、特にメチル基である。
(MeSiO3/2)0.36(ViSiO3/2)0.09(Me(MeO)SiO2/2)0.39(Vi(MeO)SiO2/2)0.10(Me(HO)SiO2/2)0.02(Me2SiO2/2)0.01(Me(MeO)2SiO1/2)0.03(数平均モル質量Mnは1680g/mol及び重量平均モル質量Mwは4340g/mol)、
(MeSiO3/2)0.40(ViSiO3/2)0.10(Me(MeO)SiO2/2)0.34(Vi(MeO)SiO2/2)0.08(Me(HO)SiO2/2)0.02(Me2SiO2/2)0.01(Me(MeO)2SiO1/2)0.02(Me3SiO1/2)0.03(数平均モル質量Mnは1640g/mol及び重量平均モル質量Mwは4080g/mol)、
(MeSiO3/2)0.44(MaSiO3/2)0.11(Me(MeO)SiO2/2)0.28(Ma(MeO)SiO2/2)0.07(Me(HO)SiO2/2)0.02(Ma(HO)SiO2/2)0.01(Me2SiO2/2)0.01(Me(MeO)2SiO1/2)0.03(Me3SiO1/2)0.03(数平均モル質量Mnは1710g/mol及び重量平均モル質量Mwは4700g/mol)、
(MeSiO3/2)0.48(ViSiO3/2)0.12(Me(MeO)SiO2/2)0.26(Vi(MeO)SiO2/2)0.07(Me(HO)SiO2/2)0.02(Me2SiO2/2)0.03(Me(MeO)2SiO1/2)0.01(Me2(OH)SiO1/2)0.01(数平均モル質量Mnは1710g/mol及び重量平均モル質量Mwは4700g/mol)、
(MeSiO3/2)0.48(ViSiO3/2)0.12(IoSiO3/2)0.01(Me(MeO)SiO2/2)0.26(Vi(MeO)SiO2/2)0.07(Me(HO)SiO2/2)0.02(Io(HO)SiO2/2)0.01(Me2SiO2/2)0.01(Me(MeO)2SiO1/2)0.01(Io(OH)2SiO1/2)0.01(数平均モル質量Mnは1540g/mol及び重量平均モル質量Mwは3630g/mol)、
(MeSiO3/2)0.25(ViSiO3/2)0.10(PhSiO3/2)0.15(Me(MeO)SiO2/2)0.21(Vi(MeO)SiO2/2)0.09(Ph(MeO)SiO2/2)0.11(Me(HO)SiO2/2)0.01(Ph(HO)SiO2/2)0.02(Me2SiO2/2)0.01(Me(MeO)2SiO1/2)0.01(Ph(OH)(MeO)SiO1/2)0.01(Me3SiO1/2)0.03(数平均モル質量Mnは1040g/mol及び重量平均モル質量Mwは1590g/mol)、
(MeSiO3/2)0.46(ViSiO3/2)0.11(Me(EtO)SiO2/2)0.28(Vi(EtO)SiO2/2)0.08(Me(HO)SiO2/2)0.02(Me2SiO2/2)0.01(Me(EtO)2SiO1/2)0.01(Me3SiO1/2)0.03(数平均モル質量Mnは1610g/mol及び重量平均モル質量Mwは3690g/mol)、
(MeSiO3/2)0.29(ViSiO3/2)0.22(Me(MeO)SiO2/2)0.08(Vi(MeO)SiO2/2)0.06(Me(HO)SiO2/2)0.01(Me2SiO2/2)0.24(Me(MeO)2SiO1/2)0.01(Me(MeO)SiO2/2)0.05(Me3SiO1/2)0.04(数平均モル質量Mnは2200g/mol及び重量平均モル質量Mwは6800g/mol)であり、
式中、Meはメチル基、Viはビニル基、Etはエチル基、Phはフェニル基、Maは3−メタクリルオキシプロピル基、Ioは2,4,4−トリメチルペンチル基である。
R7 3N(III)
のアミンであり、
式中
R7は同じであるか、又は異なっていてもよく、水素原子、又はヒドロキシル基、ハロゲン原子、アミノ基、エーテル基、エステル基、エポキシ基、メルカプト基、シアノ基、又は(ポリ)グリコール基で任意に置換され、ヘテロ原子によって中断され得る一価又は二価の炭化水素基であるが、
ただし、式(III)において最大2つの基R7が水素原子の定義を有し、
又は脂肪族環状アミン、例えばピペリジン及びモルホリンである。
R8 kR10 lSi(OR9)mO(4−k−l−m)/2(IV)、
の単位で構成されるアミンであり
式中、
R8は同じであるか、又は異なっていてもよく、塩基性窒素を含まない、一価のSiC結合の有機基であり、
R9は同じであるか、又は異なっていてもよく、基R2に指定された定義を有し、
R10は同じであるか、又は異なっていてもよく、塩基性窒素を有する一価のSiC結合の基であり、
kは0、1、2、又は3であり、
lは0、1、2、3、又は4であり、及び
mは0、1、2、又は3であり、
ただし、k+l+mの合計が4以下であり、分子あたり少なくとも1つの基R10が存在する。
HO−Si(CH3)2−(O−Si(CH3)2)0−100−(O−Si(OCH3)(CH2)3NH(CH2)2NH2)0−100−O−Si(CH3)2−OH
及び
シクロ−C6H11NH(CH2)3−Si(OCH3)2−(O−Si(CH3)2)1−100−0−Si(OCH3)2−(CH2)3NHシクロ−C6H11及び/又はその部分加水分解物及び/又はSi−O−Si含有化合物との平衡反応によって生成できる化合物であり、特に好ましいのは、H2N(CH2)3−Si(OC2H5)2−O−Si(CH3)(OC2H5)2、H2N(CH2)3−Si(OCH2CH3)2−(O−Si(OCH2CH3)2)1−100−(O−Si(OCH2CH3)(CH2)3NH2)0−100−O−Si(OCH2CH3)2−(CH2)3NH2又はH2N(CH2)2NH(CH2)3−Si(OCH3)2−(O−Si(CH3)2)0−100−(O−Si(OCH3)(CH2)3NH(CH2)2NH2)0−100−O−Si(OCH3)2−(CH2)3NH(CH2)2NH2である。
(A)オルガノポリシロキサン樹脂、
(B)式(II)の少なくとも1つの単位を有する有機化合物、
(C)開始剤、
(D)充填剤、
任意に(E)促進剤、
任意に(F)顔料、
任意に(G)有機ケイ素化合物、
(H)安定剤、
(K)アミン、
任意に(L)溶媒及び
任意に(M)調整剤
を含む。
(A)オルガノポリシロキサン樹脂、
(B)少なくとも1つのアクリレート又はメタクリレート単位を有する有機化合物、
(C)開始剤、
(D)充填剤、
(E)促進剤、
任意に(F)顔料、
任意に(G)有機ケイ素化合物、
(H)安定剤、
(K)アミン、
任意に(L)溶媒及び
任意に(M)調整剤
を含む。
(A)オルガノポリシロキサン樹脂、
(B)式(II)の少なくとも1つの単位を有する有機化合物、
(C)開始剤、
(D1)組成物1の100重量部に基づいて70〜99重量部の量の充填剤、
任意に(E)促進剤、
任意に(F)顔料、
任意に(G)有機ケイ素化合物、
(H)安定剤、
(K2)アミン、
任意に(L)溶媒及び
任意に(M)調整剤
を含む。
(A)オルガノポリシロキサン樹脂、
(B)少なくとも1つのアクリレート又はメタクリレート単位を有する有機化合物、
(C)開始剤、
(D1)組成物1の100重量部に基づいて80〜95重量部の量の充填剤(ただし、細粒及び粗粒充填剤を含む混合物が充填剤(D1)として使用され、細粒充填剤と粗粒充填剤との重量比は5:1〜1:5である)、
任意に(E)促進剤、
(F)顔料、
任意に(G)有機ケイ素化合物、
(H)安定剤、
(K2)アミン、
任意に(L)溶剤及び
任意に(M)調整剤
を含む。
(A)オルガノポリシロキサン樹脂、
(B)式(II)の少なくとも1つの単位を有する有機化合物、
(C)開始剤、
(D2)組成物2の100重量部に基づいて、少なくとも40〜90重量部の量の充填剤(ただし、充填剤(D2)は、数層の繊維織物、又は数層の繊維性レイドスクリムからなる)、
任意に(E)促進剤、
任意に(F)顔料、
任意に(G)有機ケイ素化合物、
(H)安定剤、
(K)アミン、
任意に(L)溶媒及び
任意に(M)調整剤
を含む。
(A)オルガノポリシロキサン樹脂、
(B)少なくとも1つのアクリレート又はメタクリレート単位を有する有機化合物、
(C)開始剤、
(D2)組成物2の100重量部に基づいて、少なくとも40〜90重量部の量の充填剤(ただし、充填剤(D2)は、数層の繊維織物又は数層の繊維レイドスクリムからなる)、
任意に(E)促進剤、
任意に(F)顔料、
任意に(G)有機ケイ素化合物、
(H)安定剤、
(K2)アミン、
任意に(L)溶媒及び
任意に(M)調整剤
を含む。
本発明の文脈において、粘度は、特に明記しない限り、23℃の温度及び1013hPaの大気圧で、以下の手順により低剪断速度で決定される。測定のために、20gの組成物1が、量が30mmの直径を有するように円形テンプレートを使用して、100mlの切頂プラスチックシリンジによってポリエチレンフィルムに塗布される。30分後、円形のテンプレートを上から1mmの精度で読み取り、サンプルの直径を再決定する。より大きな直径は、混合物のより高い流動性又はより低い粘度に対応する。試験の結果を表1に示す。
本発明において、曲げ強度は、ISO 178:2011−04方法Aに従って、60mmの支持距離にて2mm/分の試験速度で測定された。この場合の手順は次のとおりであった、長さ×幅×厚さ=80mm×10mm×4mmの寸法の試験片を使用した。測定は、それぞれの場合に5つの試験片で行われた。試験片は、実施例1に示されるように、DIN EN ISO 10724−1:2002−04に従って交換可能な成形キャビティプレートを有するモールドを使用する射出成形方法によって製造され、実施例1に指定された条件(温度、時間)の下で硬化された。試験中、サンプル試験片は、射出成形モールドに配置されたときと同じ方法で、すなわち底面が下になるように、常に機械に挿入された。表1に報告されているMPa単位の曲げ強度の値は、DIN 1333:1992−02セクション4に従って整数に四捨五入された、個々の測定のそれぞれの平均値に対応する。
ショアD硬度は、DIN EN ISO868:2003−10に従って決定された。測定は、ショアDデュロメータを使用して、長さ×幅×厚さ=40mm×40mm×6mmの寸法のプレートサンプル試験片で行われ、実施例1に記載されているDIN EN ISO 10724−1:2002−04フォーム2に従って、これらの試験片は交換可能なモールドキャビティプレートを有するモールドを用いる射出成形方法により、実施例1に指定されている条件(温度、時間)で硬化させた。ショアD硬度は、それぞれの場合、3つの試験片の表側及び裏側の両方で測定され、合計6つの測定値が得られた。表1に報告されている値は、個々の測定の平均値に対応している。
Meはメチル基であり、Viはビニル基であり、Etはエチル基であり、Phはフェニル基であり、Maは3−メタクリロイルオキシプロピル基であり、Ioは2,4,4−トリメチルペンチル基である。
KPGスターラを備えた加熱可能なガラス反応器で、技術等級のメチルトリメトキシシラン(Wacker Chemie AG,Munich,GermanyからSilan M1−trimethoxyの名前で市販)2080g、ビニルトリメトキシシラン(Wacker Chemie AG,Munich,GermanyからSilan V−trimethoxyの名前で市販)568.0g及びヘキサメチルジシロキサン(Wacker Chemie AG,Munich,GermanyからOl AK0,65の名前で市販)48.0gを50℃に加熱し、10分かけて水520.0g及び塩酸(水中20%、塩化水素21.9mmol、Bernd Kraft GmbH,Duisburg,GermanyからSalzsaure20%zur Analyseの名前で市販)4.00gの混合物を添加し、混合物を還流下で90分間撹拌する。続いて、2分間にわたって、混合物をナトリウムメトキシド溶液(メタノール中25%、21.1mmolのナトリウムメトキシド、SIGMA−ALDRICH Chemie GmbH、Taufkirchen,Germanyから市販)4.56gで中和する。
0.3〜0.9mmの平均粒径を有する粗粒石英顆粒(Amberger Kaolinwerke Eduard Kick GmbH,Hirschau,GermanyからSB0,3−0,9Tの名前で市販)70gに、3−アミノプロピルトリエトキシシラン(Wacker Chemie AG,Munich,GermanyからGENIOSIL(R)GF93の名前で市販)0.034gを添加し、これを、Thinkyからの「Thinky Mixer ARV−310」自転公転式ミキサーにおいて、大気圧にて1500回転/分で30秒間混合する。続いて、前処理された顆粒を23℃に冷却させる。
実施例1に記載されている手順を繰り返し、粗粒石英顆粒を3−アミノプロピルトリメトキシシランで前処理せず、むしろ3−アミノプロピルトリメトキシシランを1500回転/分にて大気圧でThinky Mixer ARV−310において、樹脂混合物1と15秒間予備混合される。次いで、実施例1に記載されているような細粒石英粉、前処理されていない粗粒石英顆粒及びtert−ブチルペルオキシベンゾエートを連続的に混合する。
3−アミノプロピルトリメトキシシランの代わりにN−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン(Wacker Chemie AG,Munich,GermanyからGENIOSIL(R)GF91の名前で市販)を使用する変更を加えて、実施例1に記載の手順を繰り返す。
3−アミノプロピルトリメトキシシランの代わりに、2−(ジメチルアミノ)エチルメタクリレート(CAS、2867−47−2)(SIGMA−ALDRICH Chemie GmbH,Taufkirchen,Germanyから市販)を使用するという変更を加えて、実施例1に記載の手順を繰り返す。
3−アミノプロピルトリメトキシシランの代わりにトリエタノールアミン(SIGMA−ALDRICH Chemie GmbH,Taufkirchen,Germanyから市販)を使用するという変更を加えて、実施例1に記載の手順を繰り返す。
3−アミノプロピルトリメトキシシランの代わりにアミン含有シリコーン油(Wacker Chemie AG,Munich,GermanyからWACKER(R)FLUID NH15 Dの名前で市販されている)を使用するという変更を加えて、実施例1に記載の手順を繰り返す。
3−アミノプロピルトリメトキシシランの代わりにメチルトリメトキシシランを使用するという変更を加えて、実施例1に記載の手順を繰り返す。
3−アミノプロピルトリメトキシシランの代わりにアミンを含まないシリコーン油(Wacker Chemie AG,Munich,GermanyからWACKER(R)WEICHMACHER X345の名前で市販されている)を使用するという変更を加えて、実施例1に記載の手順を繰り返す。
3−アミノプロピルトリメトキシシランの代わりにアミンを含まないメチルシロキサン(Wacker Chemie AG,Munich,GermanyからSILRES(R)MSE 100の名前で市販されている)を使用するという変更を加えて、実施例1に記載の手順を繰り返す。
3−アミノプロピルトリメトキシシランを使用しないという変更を加えて、実施例1に記載の手順を繰り返す。
Claims (12)
- (A)一般式
RaR1 b(OR2)cSiO(4−a−b−c)/2(I)、
の単位からなるオルガノポリシロキサン樹脂、
式中、
Rは同じであるか、又は異なっていてもよく、水素原子又は脂肪族炭素−炭素多重結合を含まない、一価のSiC結合の任意に置換される炭化水素基であり、
R1は同じであるか、又は異なっていてもよく、脂肪族炭素−炭素多重結合を有する、一価のSiC結合の任意に置換される炭化水素基であり、
R2は同じであるか、又は異なっていてもよく、水素原子又は一価の、任意に置換される炭化水素基であり、
aは0、1、2、又は3であり、
bは0又は1であり、及び
cは0、1、2、又は3であり、
ただし、それぞれの場合に、オルガノポリシロキサン樹脂(A)中の式(I)のすべてのシロキサン単位に基づいて、式(I)においてa+b+cの合計は≦3であり、式(I)の少なくとも1つの単位においてb=1であり、式(I)の単位の少なくとも50%においてa+b=1であり、及び式(I)の単位の最大10%においてa+b=3であり、
(B)式
CR3 2=CR3−CO−Z−(II)、
の少なくとも1つの単位を有する有機化合物、
式中、
R3は同じであるか、又は異なっていてもよく、水素原子、シアノ基−CN又はヘテロ原子によって中断され得る一価の、任意に置換される炭化水素基であり、
Zは同じであるか、又は異なっていてもよく、−O−又は−NR5−であり、
及び
R5は同じであるか、又は異なっていてもよく、水素原子又はヘテロ原子によって中断され得る一価の、任意に置換される炭化水素基であり、
(C)開始剤、
(D)充填剤並びに
(K)アミン
を含む組成物。 - オルガノポリシロキサン樹脂(A)において、R1=ビニル基である式(I)の単位の合計が、b=1である式(I)のすべての単位に基づいて、少なくとも80%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、成分(A)100重量部に基づいて、成分(B)を1〜250重量部の量で含むことを特徴とする、請求項1又は2に記載の組成物。
- 樹脂(A)において、b=1である式(I)の単位の合計が10%〜40%であることを特徴とする、請求項1〜3の1つ以上に記載の組成物。
- 成分(D)が、5cmまでの長さの繊維(D1)及び5cmを超える長さを有する繊維を含む繊維半製品(D2)を含む、粒子状充填剤から選択される成分を含むことを特徴とする、請求項1〜4の1つ以上に記載の組成物。
- 細粒及び粗粒充填剤を含む混合物が成分(D1)として使用されることを特徴とする、請求項5に記載の組成物。
- 織物、レイドスクリム、ニット、ブレード、マット又は不織布が成分(D2)として使用されることを特徴とする、請求項5に記載の組成物。
- 前記組成物が、成分(A)及び(B)の総重量の100重量部に基づいて、成分(K)を0.001〜5重量部の量で含むことを特徴とする、請求項1〜7の1つ以上に記載の組成物。
- 個々の成分を任意の順序で混合することにより、請求項1〜8の1つ以上に記載の組成物を製造する方法。
- 請求項1〜8の1つ以上に記載の組成物を架橋することにより製造された、又は請求項9に記載のように製造された成形品。
- 請求項6に記載の組成物を成形し、架橋させることを特徴とする、人工石の製造方法。
- 請求項7に記載の組成物を成形し、架橋させることを特徴とする、繊維複合体の製造方法。
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