TWI635119B - 包含含氮有機氧矽烷化合物的組成物及其製造方法 - Google Patents
包含含氮有機氧矽烷化合物的組成物及其製造方法 Download PDFInfo
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- TWI635119B TWI635119B TW103140061A TW103140061A TWI635119B TW I635119 B TWI635119 B TW I635119B TW 103140061 A TW103140061 A TW 103140061A TW 103140061 A TW103140061 A TW 103140061A TW I635119 B TWI635119 B TW I635119B
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- Prior art keywords
- nitrogen
- compound
- general formula
- mass
- containing organic
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 62
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title description 8
- -1 nitrogen-containing organosiloxane compound Chemical class 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 27
- 229910052697 platinum Inorganic materials 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 7
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 6
- 239000000853 adhesive Substances 0.000 abstract description 6
- 230000001070 adhesive effect Effects 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 239000000835 fiber Substances 0.000 abstract description 6
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 239000012756 surface treatment agent Substances 0.000 abstract description 6
- 230000000996 additive effect Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 239000003973 paint Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 239000001099 ammonium carbonate Substances 0.000 description 10
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 9
- 150000003512 tertiary amines Chemical group 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 8
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 8
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 7
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical group CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JXNGSNLOFNAVJI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n,n-dimethylpropan-1-amine Chemical compound CO[Si](C)(OC)CCCN(C)C JXNGSNLOFNAVJI-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- KXYIXMDBNFMXIW-UHFFFAOYSA-N n,n-dimethyl-1-triethoxysilylpropan-2-amine Chemical compound CCO[Si](OCC)(OCC)CC(C)N(C)C KXYIXMDBNFMXIW-UHFFFAOYSA-N 0.000 description 5
- BMEQUUBENOHASH-UHFFFAOYSA-N n,n-dimethyl-1-trimethoxysilylpropan-2-amine Chemical compound CO[Si](OC)(OC)CC(C)N(C)C BMEQUUBENOHASH-UHFFFAOYSA-N 0.000 description 5
- AQIQPUUNTCVHBS-UHFFFAOYSA-N n,n-dimethyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(C)C AQIQPUUNTCVHBS-UHFFFAOYSA-N 0.000 description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 5
- TXCYYEDNKVBQPW-UHFFFAOYSA-N 1-[dimethoxy(methyl)silyl]-N,N-dimethylpropan-2-amine Chemical compound CO[Si](C)(CC(C)N(C)C)OC TXCYYEDNKVBQPW-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NALIQVLPVWZDOO-UHFFFAOYSA-N 1-$l^{1}-oxidanyloxypropane Chemical compound CCCO[O] NALIQVLPVWZDOO-UHFFFAOYSA-N 0.000 description 1
- QBWNUJUVFDWMRN-UHFFFAOYSA-N 1-methyl-4-prop-2-enylpiperazine Chemical compound CN1CCN(CC=C)CC1 QBWNUJUVFDWMRN-UHFFFAOYSA-N 0.000 description 1
- KYGMSGYKSGNPHM-UHFFFAOYSA-N 1-prop-2-enylpiperidine Chemical compound C=CCN1CCCCC1 KYGMSGYKSGNPHM-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HCBHAYZGECJCGL-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]-n,n-diethylpropan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN(CC)CC HCBHAYZGECJCGL-UHFFFAOYSA-N 0.000 description 1
- ZZNRMMYTKJBVPD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]-n,n-dimethylpropan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN(C)C ZZNRMMYTKJBVPD-UHFFFAOYSA-N 0.000 description 1
- FHLZUEPKLGQEQP-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCC[Si](C)(OC)OC FHLZUEPKLGQEQP-UHFFFAOYSA-N 0.000 description 1
- SWFMEKYKNYKVQN-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n,n-dipropylpropan-1-amine Chemical compound CCCN(CCC)CCC[Si](C)(OC)OC SWFMEKYKNYKVQN-UHFFFAOYSA-N 0.000 description 1
- JFQQDUFCGOBUNA-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]-n,n-diethylpropan-1-amine Chemical compound CCO[Si](C)(C)CCCN(CC)CC JFQQDUFCGOBUNA-UHFFFAOYSA-N 0.000 description 1
- URWZAYNFHNPVLO-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]-n,n-dipropylpropan-1-amine Chemical compound CCCN(CCC)CCC[Si](C)(C)OCC URWZAYNFHNPVLO-UHFFFAOYSA-N 0.000 description 1
- BNNQAWRZJYZWDX-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]-n,n-dimethylpropan-1-amine Chemical compound CO[Si](C)(C)CCCN(C)C BNNQAWRZJYZWDX-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical class CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- SUSANAYXICMXBL-UHFFFAOYSA-N 4-prop-2-enylmorpholine Chemical compound C=CCN1CCOCC1 SUSANAYXICMXBL-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RFIAUHDYYXYZQE-UHFFFAOYSA-N C(=C)[Si](N[Si](C)(C)C=C)(C)C.[Pt] Chemical compound C(=C)[Si](N[Si](C)(C)C=C)(C)C.[Pt] RFIAUHDYYXYZQE-UHFFFAOYSA-N 0.000 description 1
- NQVWLHZKUBUSCU-UHFFFAOYSA-N CCCCN(CCCC)C(C)C[Si](C)(C)OC Chemical compound CCCCN(CCCC)C(C)C[Si](C)(C)OC NQVWLHZKUBUSCU-UHFFFAOYSA-N 0.000 description 1
- SRHLMGJYPUZDIV-UHFFFAOYSA-N CCCCN(CCCC)C(C)C[Si](C)(C)OCC Chemical compound CCCCN(CCCC)C(C)C[Si](C)(C)OCC SRHLMGJYPUZDIV-UHFFFAOYSA-N 0.000 description 1
- AIAHPAVEIWYJEB-UHFFFAOYSA-N CCCCN(CCCC)C(C)C[Si](C)(OC)OC Chemical compound CCCCN(CCCC)C(C)C[Si](C)(OC)OC AIAHPAVEIWYJEB-UHFFFAOYSA-N 0.000 description 1
- NFDJPQYASAQEGH-UHFFFAOYSA-N CCCCN(CCCC)C(C)C[Si](C)(OCC)OCC Chemical compound CCCCN(CCCC)C(C)C[Si](C)(OCC)OCC NFDJPQYASAQEGH-UHFFFAOYSA-N 0.000 description 1
- SKNYSPJTHITTCE-UHFFFAOYSA-N CCCCN(CCCC)C(C)C[Si](OC)(OC)OC Chemical compound CCCCN(CCCC)C(C)C[Si](OC)(OC)OC SKNYSPJTHITTCE-UHFFFAOYSA-N 0.000 description 1
- OQEMHGJSBMOEDW-UHFFFAOYSA-N CCCCN(CCCC)C(C)C[Si](OCC)(OCC)OCC Chemical compound CCCCN(CCCC)C(C)C[Si](OCC)(OCC)OCC OQEMHGJSBMOEDW-UHFFFAOYSA-N 0.000 description 1
- HGFCVHNZYAMREP-UHFFFAOYSA-N CCCCN(CCCC)CCC[Si](C)(C)OCC Chemical compound CCCCN(CCCC)CCC[Si](C)(C)OCC HGFCVHNZYAMREP-UHFFFAOYSA-N 0.000 description 1
- VCFCGVWYNFVSCP-UHFFFAOYSA-N CCCCN(CCCC)CCC[Si](C)(OCC)OCC Chemical compound CCCCN(CCCC)CCC[Si](C)(OCC)OCC VCFCGVWYNFVSCP-UHFFFAOYSA-N 0.000 description 1
- HMXNCCAJJYYKPZ-UHFFFAOYSA-N CCCN(CCC)C(C)C[Si](C)(C)OC Chemical compound CCCN(CCC)C(C)C[Si](C)(C)OC HMXNCCAJJYYKPZ-UHFFFAOYSA-N 0.000 description 1
- CIIKGJFCNXULSH-UHFFFAOYSA-N CCCN(CCC)C(C)C[Si](C)(C)OCC Chemical compound CCCN(CCC)C(C)C[Si](C)(C)OCC CIIKGJFCNXULSH-UHFFFAOYSA-N 0.000 description 1
- RSIYXIIAYJKDBB-UHFFFAOYSA-N CCCN(CCC)C(C)C[Si](C)(OC)OC Chemical compound CCCN(CCC)C(C)C[Si](C)(OC)OC RSIYXIIAYJKDBB-UHFFFAOYSA-N 0.000 description 1
- BCVIWKVMPMGAMX-UHFFFAOYSA-N CCCN(CCC)C(C)C[Si](C)(OCC)OCC Chemical compound CCCN(CCC)C(C)C[Si](C)(OCC)OCC BCVIWKVMPMGAMX-UHFFFAOYSA-N 0.000 description 1
- JHPIZVOEHUKUMG-UHFFFAOYSA-N CCCN(CCC)C(C)C[Si](OC)(OC)OC Chemical compound CCCN(CCC)C(C)C[Si](OC)(OC)OC JHPIZVOEHUKUMG-UHFFFAOYSA-N 0.000 description 1
- YOWQDNFSIRNYHB-UHFFFAOYSA-N CCCN(CCC)C(C)C[Si](OCC)(OCC)OCC Chemical compound CCCN(CCC)C(C)C[Si](OCC)(OCC)OCC YOWQDNFSIRNYHB-UHFFFAOYSA-N 0.000 description 1
- SNWLMLOOYREREK-UHFFFAOYSA-N CCCN(CCC)CCC[Si](C)(C)OC Chemical compound CCCN(CCC)CCC[Si](C)(C)OC SNWLMLOOYREREK-UHFFFAOYSA-N 0.000 description 1
- IDOMDOFIAIFXRI-UHFFFAOYSA-N CCCN(CCC)CCC[Si](C)(OCC)OCC Chemical compound CCCN(CCC)CCC[Si](C)(OCC)OCC IDOMDOFIAIFXRI-UHFFFAOYSA-N 0.000 description 1
- ISMYKHKQXWEGOF-UHFFFAOYSA-N CCN(CC)C(C)C[Si](C)(C)OC Chemical compound CCN(CC)C(C)C[Si](C)(C)OC ISMYKHKQXWEGOF-UHFFFAOYSA-N 0.000 description 1
- WNAQAPGGEYIYFY-UHFFFAOYSA-N CCN(CC)C(C)C[Si](C)(OC)OC Chemical compound CCN(CC)C(C)C[Si](C)(OC)OC WNAQAPGGEYIYFY-UHFFFAOYSA-N 0.000 description 1
- MXJIHSYLHKAHTK-UHFFFAOYSA-N CCN(CC)C(C)C[Si](OC)(OC)OC Chemical compound CCN(CC)C(C)C[Si](OC)(OC)OC MXJIHSYLHKAHTK-UHFFFAOYSA-N 0.000 description 1
- ZVASEAHCZYYKPQ-UHFFFAOYSA-N CCO[Si](C)(C)CC(C)N(CC)CC Chemical compound CCO[Si](C)(C)CC(C)N(CC)CC ZVASEAHCZYYKPQ-UHFFFAOYSA-N 0.000 description 1
- XQJKCCMLKFILEI-UHFFFAOYSA-N CCO[Si](C)(C)CC(C)NCc1ccccc1 Chemical compound CCO[Si](C)(C)CC(C)NCc1ccccc1 XQJKCCMLKFILEI-UHFFFAOYSA-N 0.000 description 1
- OXHNEUCSRLXRHH-UHFFFAOYSA-N CCO[Si](C)(CC(C)N(C)C)OCC Chemical compound CCO[Si](C)(CC(C)N(C)C)OCC OXHNEUCSRLXRHH-UHFFFAOYSA-N 0.000 description 1
- RDLNXZGJYKEYRX-UHFFFAOYSA-N CCO[Si](C)(CC(C)N(CC)CC)OCC Chemical compound CCO[Si](C)(CC(C)N(CC)CC)OCC RDLNXZGJYKEYRX-UHFFFAOYSA-N 0.000 description 1
- NYGDEIQVQGCJQB-UHFFFAOYSA-N CCO[Si](C)(CC(C)NCc1ccccc1)OCC Chemical compound CCO[Si](C)(CC(C)NCc1ccccc1)OCC NYGDEIQVQGCJQB-UHFFFAOYSA-N 0.000 description 1
- YIYDPGGLZQOASJ-UHFFFAOYSA-N CCO[Si](CC(C)N(CC)CC)(OCC)OCC Chemical compound CCO[Si](CC(C)N(CC)CC)(OCC)OCC YIYDPGGLZQOASJ-UHFFFAOYSA-N 0.000 description 1
- ONLWLCVRUGYHHC-UHFFFAOYSA-N CCO[Si](CC(C)NCc1ccccc1)(OCC)OCC Chemical compound CCO[Si](CC(C)NCc1ccccc1)(OCC)OCC ONLWLCVRUGYHHC-UHFFFAOYSA-N 0.000 description 1
- JZVLRNIOLSVDSU-UHFFFAOYSA-N CN1CCN(CC1)C(C[Si](OC)(C)C)C Chemical compound CN1CCN(CC1)C(C[Si](OC)(C)C)C JZVLRNIOLSVDSU-UHFFFAOYSA-N 0.000 description 1
- HPNSSBAAWMIPDC-UHFFFAOYSA-N CN1CCN(CC1)C(C[Si](OC)(OC)C)C Chemical compound CN1CCN(CC1)C(C[Si](OC)(OC)C)C HPNSSBAAWMIPDC-UHFFFAOYSA-N 0.000 description 1
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- UDYOPKBLCKMWJC-UHFFFAOYSA-N CN1CCN(CC1)C(C[Si](OCC)(C)C)C Chemical compound CN1CCN(CC1)C(C[Si](OCC)(C)C)C UDYOPKBLCKMWJC-UHFFFAOYSA-N 0.000 description 1
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- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
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- 229910052786 argon Inorganic materials 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 235000019838 diammonium phosphate Nutrition 0.000 description 1
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- PXLCGNYELDUAJK-UHFFFAOYSA-N dimethoxy-methyl-(3-piperidin-2-ylpropyl)silane Chemical compound CO[Si](C)(OC)CCCC1CCCCN1 PXLCGNYELDUAJK-UHFFFAOYSA-N 0.000 description 1
- BHNDAMNVBFKORD-UHFFFAOYSA-N dimethoxy-methyl-(3-piperidin-3-ylpropyl)silane Chemical compound CO[Si](C)(CCCC1CCCNC1)OC BHNDAMNVBFKORD-UHFFFAOYSA-N 0.000 description 1
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- SDSOGGABQAVLEB-UHFFFAOYSA-N dimethyl-[(2-methylpropan-2-yl)oxy]-propylsilane Chemical compound CCC[Si](C)(C)OC(C)(C)C SDSOGGABQAVLEB-UHFFFAOYSA-N 0.000 description 1
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
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- QTUUPKROZQAGNZ-UHFFFAOYSA-N methoxy-dimethyl-[3-(4-methylpiperazin-1-yl)propyl]silane Chemical compound CO[Si](C)(C)CCCN1CCN(C)CC1 QTUUPKROZQAGNZ-UHFFFAOYSA-N 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
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- SLONIUALCCYCDN-UHFFFAOYSA-N n,n-diethyl-3-[methoxy(dimethyl)silyl]propan-1-amine Chemical compound CCN(CC)CCC[Si](C)(C)OC SLONIUALCCYCDN-UHFFFAOYSA-N 0.000 description 1
- BVBBZEKOMUDXMZ-UHFFFAOYSA-N n,n-diethyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(CC)CC BVBBZEKOMUDXMZ-UHFFFAOYSA-N 0.000 description 1
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 1
- JWAJUTZQGZBKFS-UHFFFAOYSA-N n,n-diethylprop-2-en-1-amine Chemical compound CCN(CC)CC=C JWAJUTZQGZBKFS-UHFFFAOYSA-N 0.000 description 1
- NSHXKSKCSAEYMF-UHFFFAOYSA-N n,n-dipropyl-3-triethoxysilylpropan-1-amine Chemical compound CCCN(CCC)CCC[Si](OCC)(OCC)OCC NSHXKSKCSAEYMF-UHFFFAOYSA-N 0.000 description 1
- WLBHGVYLQDPNCL-UHFFFAOYSA-N n,n-dipropyl-3-trimethoxysilylpropan-1-amine Chemical compound CCCN(CCC)CCC[Si](OC)(OC)OC WLBHGVYLQDPNCL-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical group CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- UBGBYUQXKCSQKS-UHFFFAOYSA-N n-benzyl-3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCNCC1=CC=CC=C1 UBGBYUQXKCSQKS-UHFFFAOYSA-N 0.000 description 1
- FKLYLJYMNADAQF-UHFFFAOYSA-N n-benzyl-3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCNCC1=CC=CC=C1 FKLYLJYMNADAQF-UHFFFAOYSA-N 0.000 description 1
- GVZFVGOROJUZTI-UHFFFAOYSA-N n-benzyl-3-[ethoxy(dimethyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(C)CCCNCC1=CC=CC=C1 GVZFVGOROJUZTI-UHFFFAOYSA-N 0.000 description 1
- ILRLVKWBBFWKTN-UHFFFAOYSA-N n-benzyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCC1=CC=CC=C1 ILRLVKWBBFWKTN-UHFFFAOYSA-N 0.000 description 1
- CLYWMXVFAMGARU-UHFFFAOYSA-N n-benzyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCC1=CC=CC=C1 CLYWMXVFAMGARU-UHFFFAOYSA-N 0.000 description 1
- DLAUQJZKDAKQGO-UHFFFAOYSA-N n-butyl-n-(3-triethoxysilylpropyl)butan-1-amine Chemical compound CCCCN(CCCC)CCC[Si](OCC)(OCC)OCC DLAUQJZKDAKQGO-UHFFFAOYSA-N 0.000 description 1
- YGYLBNUUMURMPO-UHFFFAOYSA-N n-butyl-n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCN(CCCC)CCC[Si](OC)(OC)OC YGYLBNUUMURMPO-UHFFFAOYSA-N 0.000 description 1
- GLRJALJAKGWUEF-UHFFFAOYSA-N n-butyl-n-[3-[dimethoxy(methyl)silyl]propyl]butan-1-amine Chemical compound CCCCN(CCCC)CCC[Si](C)(OC)OC GLRJALJAKGWUEF-UHFFFAOYSA-N 0.000 description 1
- XXKFHYIDWHPLHG-UHFFFAOYSA-N n-butyl-n-prop-2-enylbutan-1-amine Chemical compound CCCCN(CC=C)CCCC XXKFHYIDWHPLHG-UHFFFAOYSA-N 0.000 description 1
- URBIUAWKOUCECW-UHFFFAOYSA-N n-prop-2-enyl-n-propylpropan-1-amine Chemical compound CCCN(CCC)CC=C URBIUAWKOUCECW-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- XAKYZBMFCZISAU-UHFFFAOYSA-N platinum;triphenylphosphane Chemical compound [Pt].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 XAKYZBMFCZISAU-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- XHSMJSNXQUKFBB-UHFFFAOYSA-N triethoxy(3-morpholin-4-ylpropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCOCC1 XHSMJSNXQUKFBB-UHFFFAOYSA-N 0.000 description 1
- IAQZGDZLEOYROO-UHFFFAOYSA-N triethoxy(3-piperidin-3-ylpropyl)silane Chemical compound CCO[Si](CCCC1CCCNC1)(OCC)OCC IAQZGDZLEOYROO-UHFFFAOYSA-N 0.000 description 1
- LJSCMFMGPIFSDE-UHFFFAOYSA-N triethoxy-[3-(4-methylpiperazin-1-yl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCN(C)CC1 LJSCMFMGPIFSDE-UHFFFAOYSA-N 0.000 description 1
- SZUDBEZTBZNXDA-UHFFFAOYSA-N trimethoxy(3-piperidin-2-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCC1CCCCN1 SZUDBEZTBZNXDA-UHFFFAOYSA-N 0.000 description 1
- BSHSWKDSNHUZLL-UHFFFAOYSA-N trimethoxy(3-piperidin-3-ylpropyl)silane Chemical compound CO[Si](CCCC1CCCNC1)(OC)OC BSHSWKDSNHUZLL-UHFFFAOYSA-N 0.000 description 1
- JBYYGVMOBTYNOM-UHFFFAOYSA-N trimethoxy-[3-(4-methylpiperazin-1-yl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCN1CCN(C)CC1 JBYYGVMOBTYNOM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
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Abstract
本發明係關於一種包含含氮有機氧矽烷化合物的組成物,其係由以下述通式(1)表示之含氮有機氧矽烷化合物90~99質量份,及以下述通式(2)表示之含氮有機氧矽烷化合物1~10質量份所成:
(R1、R2、R4、R5為碳數1~20之取代或未取代之1價烴基,亦可相互鍵結與該等所鍵結之氮原子一起形成環,該環除上述氮原子外亦可介隔有雜原子,亦可具有取代基,R3為碳數1~10之2價烴基,n為0、1或2),
(R1、R2、R3、R4、R5、n與上述相同)。
本發明之包含含氮有機氧矽烷化合物之組成物由於可
賦予適度之硬化性、添加效果,故可有用作為塗料添加劑、接著劑、矽烷偶合劑、纖維處理劑、表面處理劑等。
Description
本發明係關於有用作為塗料添加劑、接著劑、矽烷偶合劑、纖維處理劑、表面處理劑等之包含含氮有機氧矽烷化合物之組成物及其製造方法。
具有胺基之矽烷化合物有用作為塗料添加劑、接著劑、矽烷偶合劑、纖維處理劑、表面處理劑,作為具有該等胺基之矽烷化合物已知有胺基丙基三甲氧基矽烷等具有1級胺基之有機氧矽烷化合物或N-苯基胺基丙基三甲氧基矽烷等具有2級胺基之有機氧矽烷化合物,或二甲胺基丙基三甲氧基矽烷等具有3級胺基之有機氧矽烷化合物等。
上述具有胺基之有機氧矽烷化合物通常大多情況係以單品使用,但亦有包含具有分支構造之異構物時較佳之情況。例如,使用於液晶配向膜用時藉由存在異構物而可調節液晶之配向性。此外,作為其他例,針對於單
一成分熔點高而處理不易之化合物,藉由存在異構物而降低熔點,可使處理變容易。但,用於上述用途時,存在過多異構物時會有損及原有效果之可能性,故較佳為適度含有異構物之包含具有胺基之有機氧矽烷之組成物。
上述具有胺基之有機氧矽烷中,二甲胺基丙基三甲氧基矽烷等具有3級胺基之有機氧矽烷化合物係作為酸酐、聚胺、聚醯胺系環氧樹脂硬化劑之促進劑或共硬化劑有用之化合物。具有3級胺基之有機氧矽烷化合物中,若完全無異構物則使用作為環氧樹脂添加劑等時,會有硬化速度變快之可能性,含有較多異構物時會有硬化速度過慢之可能性,故較佳為適度含有異構物之組成物。
獲得上述具有3級胺基之有機氧矽烷化合物時,一般係採用利用鉑觸媒進行之由具有3級胺基之含不飽和鍵之化合物與氫有機氧矽烷化合物之氫矽烷基化反應而合成之方法(非專利文獻1:Zh.Obshch.Khim.,(1984)54,657)。又,作為獲得具有3級胺基之有機氧矽烷化合物之另一種方法,例示有使2級胺化合物與鹵烷基有機氧矽烷化合物反應之方法(專利文獻1:日本特開2008-143855號公報)。
〔專利文獻1〕日本特開2008-143855號公報
〔非專利文獻1〕Zh. Obshch. Khim., (1984) 54,657
然而,非專利文獻1之方法之情況下,氫矽烷基化反應時生成30~50質量%左右之加成異構物,而成為含有較多異構物之具有3級胺基之有機氧矽烷化合物之組成物。另外,專利文獻1之情況下,由於完全不生成異構物,故無法獲得含有適度異構物之具有3級胺基之含有機氧矽烷化合物之組成物。此外,上述方法在反應時生成胺鹽酸鹽,故不僅需要過濾等複雜之操作,且有於製品中混入胺鹽酸鹽,而對品質造成不良影響之可能性。進而,2級胺化合物使用二甲基胺等之在室溫下為氣體之化合物時,必須於加壓下實施反應,於工業上不利。
本發明係鑑於上述問題而完成者,其目的係提供一種作為塗料添加劑、接著劑、矽烷偶合劑、纖維處理劑、表面處理劑等使用時,可賦予適度硬化性之包含含氮有機氧矽烷化合物之組成物及其製造方法。
本發明人等為達成上述目的而重複積極檢討之結果,發現利用鉑觸媒使具有3級胺基之含不飽和鍵之
化合物與氫有機氧矽烷化合物之氫矽烷基化反應而合成具有3級胺基之有機氧矽烷化合物時,若在無機酸之銨鹽存在下實施反應,則可使加成異構物成為1~10質量%,含有如此適量之該加成異構物之包含含氮有機氧矽烷化合物作為塗料添加劑、接著劑、矽烷偶合劑、纖維處理劑、表面處理劑等使用時,可賦予適度之硬化性、添加效果,因而至於完成本發明。
據此,本發明係提供包含下述所示之含氮有機氧矽烷化合物之組成物及其製造方法。
〔1〕一種包含含氮有機氧矽烷化合物的組成物,其係由以下述通式(1)表示之含氮有機氧矽烷化合物90~99質量份,及以下述通式(2)表示之含氮有機氧矽烷化合物1~10質量份所成:
(式中,R1、R2為碳數1~20之取代或未取代之1價烴基,亦可相互鍵結與該等所鍵結之氮原子一起形成環,該環除上述氮原子外可介隔有雜原子,亦可具有取代基,R3為碳數1~10之2價烴基,R4、R5為碳數1~20之取代或未取代之1價烴基,n為0、1或2),
(式中,R1、R2、R3、R4、R5、n與上述相同)。
〔2〕如[1]所記載之組成物,其中R1、R2為甲基,R3為亞甲基。
〔3〕一種如[1]或[2]所記載之包含含氮有機氧矽烷化合物的組成物之製造方法,其特徵係在無機酸之銨鹽存在下使用鉑觸媒使以下述通式(3)所示之包含含氮不飽和鍵之化合物與以下述通式(4)表示之氫有機氧矽烷化合物進行氫矽烷基化,
(式中,R1、R2、R3與上述相同),HSiR4 n(OR5)3-n (4)(式中,R4、R5、n與上述相同)。
本發明提供之包含含氮有機氧矽烷化合物組成物由於可賦予適度之硬化性、添加效果,故可有用作為塗料添加劑、接著劑、矽烷偶合劑、纖維處理劑、表面處理劑等。
本發明之含氮有機氧矽烷化合物的組成物係
由以下述通式(1)表示之含氮有機氧矽烷化合物90~99質量份,及以下述通式(2)表示之含氮有機氧矽烷化合物1~10質量份所成之組成物:
(式中,R1、R2為碳數1~20之取代或未取代之1價烴基,亦可相互鍵結與該等所鍵結之氮原子一起形成環,R3為碳數1~10之2價烴基,R4、R5為碳數1~20之取代或未取代之1價烴基,n為0、1或2),
(式中,R1、R2、R3、R4、R5、n與上述相同)。
本文中,R1、R2、R4、R5之碳數1~20,較佳為1~10之取代或未取代之1價烴基列舉為直鏈狀、分支鏈狀或環狀之烷基、烯基、芳基、芳烷基等。具體而言例示為甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、癸基、十二烷基、十四烷基、十六烷基、十八烷基、二十烷基等直鏈狀之烷基,異丙基、異丁基、第二丁基、第三丁基、第三己基(thexyl)、2-乙基己基等分支鏈狀之烷基,環戊基、環己基等環狀烷基,乙烯基、烯丙基、丙烯基等烯基,苯基、甲苯基等芳基,苄基等芳烷基等,尤其就原料取得容易性之觀點而言,以甲基、乙基、異丙
基、第二丁基、第三丁基較佳。此外,烴基之氫原子之一部分或全部亦可經取代,作為該取代基具體列舉為例如甲氧基、乙氧基、(異)丙氧基等烷氧基;氟原子、氯原子、溴原子、碘原子等鹵原子;氰基、胺基;碳數2~10之醯基、各別之各烷基、各烷氧基為碳數1~5之三烷基矽烷基、三烷氧基矽烷基、二烷基單烷氧基矽烷基或單烷基二烷氧基矽烷基,亦可組合該等使用。
另外,R1與R2結合並與該等所鍵結之氮原子一起形成環時,R1R2N-成為含氮雜環。含氮雜環除使R1之碳原子與R2之碳原子所直接鍵結者外,R1之碳原子與R2之碳原子亦可介隔1個以上之氧原子、氮原子等雜原子鍵結而形成環者。R1與R2形成環時之環中所含之碳數較佳為3~6。
含氮雜環亦可具有取代基,作為取代基具體列舉為例如甲基、乙基、(異)丙基、己基等烷基;甲氧基、乙氧基、(異)丙氧基等烷氧基;由氟原子、氯原子、溴原子、碘原子等鹵原子所成之基、氰基、胺基、芳香族烴基、酯基、醚基、醯基、硫醚基等。亦可組合該等而使用。該等取代基之取代位置並無特別限制,取代基數亦無限制。作為該等含氮雜環具體列舉為例如哌啶、哌嗪、嗎啉、吡咯啶、吡咯啶酮、哌啶酮及該等之衍生物等。
R3為碳數1~10,較佳為1~6之2價烴基。作為碳數1~10之2價烴基具體例示為亞甲基、伸乙基、甲基伸乙基、伸丙基、甲基伸丙基、四亞甲基、六亞甲基、
八亞甲基、十亞甲基、異伸丁基等伸烷基,伸苯基等伸芳基、亞甲基伸苯基、亞甲基伸苯基亞甲基等伸芳烷基。
以上述通式(1)表示之含氮有機氧矽烷化合物之具體例例示為3-二甲胺基丙基三甲氧基矽烷、3-二甲胺基丙基甲基二甲氧基矽烷、3-二甲胺基丙基二甲基甲氧基矽烷、3-二甲胺基丙基三乙氧基矽烷、3-二甲胺基丙基甲基二乙氧基矽烷、3-二甲胺基丙基二甲基乙氧基矽烷、3-二乙胺基丙基三甲氧基矽烷、3-二乙胺基丙基甲基二甲氧基矽烷、3-二乙胺基丙基二甲基甲氧基矽烷、3-二乙胺基丙基三乙氧基矽烷、3-二乙胺基丙基甲基二乙氧基矽烷、3-二乙胺基丙基二甲基乙氧基矽烷、3-二丙胺基丙基三甲氧基矽烷、3-二丙胺基丙基甲基二甲氧基矽烷、3-二丙胺基丙基二甲基甲氧基矽烷、3-二丙胺基丙基三乙氧基矽烷、3-二丙胺基丙基甲基二乙氧基矽烷、3-二丙胺基丙基二甲基乙氧基矽烷、3-二丁胺基丙基三甲氧基矽烷、3-二丁胺基丙基甲基二甲氧基矽烷、3-二丁胺基丙基二甲基甲氧基矽烷、3-二丁胺基丙基三乙氧基矽烷、3-二丁胺基丙基甲基二乙氧基矽烷、3-二丁胺基丙基二甲基乙氧基矽烷、3-苯基甲基胺基丙基三甲氧基矽烷、3-苯基甲基胺基丙基甲基二甲氧基矽烷、3-苯基甲基胺基丙基二甲基甲氧基矽烷、3-苯基甲基胺基丙基三乙氧基矽烷、3-苯基甲基胺基丙基甲基二乙氧基矽烷、3-苯基甲基胺基丙基二甲基乙氧基矽烷、3-哌啶基丙基三甲氧基矽烷、3-哌啶基丙基甲基二甲氧基矽烷、3-哌啶基丙基二甲基甲氧基矽烷、3-
哌啶基丙基三乙氧基矽烷、3-哌啶基丙基甲基二乙氧基矽烷、3-哌啶基丙基二甲基乙氧基矽烷、3-嗎啉基丙基三甲氧基矽烷、3-嗎啉基丙基甲基二甲氧基矽烷、3-嗎啉基丙基二甲基甲氧基矽烷、3-嗎啉基丙基三乙氧基矽烷、3-嗎啉基丙基甲基二乙氧基矽烷、3-嗎啉基丙基二甲基乙氧基矽烷、3-(4-甲基哌嗪-1-基)丙基三甲氧基矽烷、3-(4-甲基哌嗪-1-基)丙基甲基二甲氧基矽烷、3-(4-甲基哌嗪-1-基)丙基二甲基甲氧基矽烷、3-(4-甲基哌嗪-1-基)丙基三乙氧基矽烷、3-(4-甲基哌嗪-1-基)丙基甲基二乙氧基矽烷、3-(4-甲基哌嗪-1-基)丙基二甲基乙氧基矽烷等。
此外,以上述通式(2)表示之含氮有機氧矽烷化合物與以上述通式(1)表示之含氮有機氧矽烷化合物為異構物之關係。以上述通式(2)表示之化合物之具體例例示為2-二甲胺基丙基三甲氧基矽烷、2-二甲胺基丙基甲基二甲氧基矽烷、2-二甲胺基丙基二甲基甲氧基矽烷、2-二甲胺基丙基三乙氧基矽烷、2-二甲胺基丙基甲基二乙氧基矽烷、2-二甲胺基丙基二甲基乙氧基矽烷、2-二乙胺基丙基三甲氧基矽烷、2-二乙胺基丙基甲基二甲氧基矽烷、2-二乙胺基丙基二甲基甲氧基矽烷、2-二乙胺基丙基三乙氧基矽烷、2-二乙胺基丙基甲基二乙氧基矽烷、2-二乙胺基丙基二甲基乙氧基矽烷、2-二丙胺基丙基三甲氧基矽烷、2-二丙胺基丙基甲基二甲氧基矽烷、2-二丙胺基丙基二甲基甲氧基矽烷、2-二丙胺基丙基三乙氧基矽烷、
2-二丙胺基丙基甲基二乙氧基矽烷、2-二丙胺基丙基二甲基乙氧基矽烷、2-二丁胺基丙基三甲氧基矽烷、2-二丁胺基丙基甲基二甲氧基矽烷、2-二丁胺基丙基二甲基甲氧基矽烷、2-二丁胺基丙基三乙氧基矽烷、2-二丁胺基丙基甲基二乙氧基矽烷、2-二丁胺基丙基二甲基乙氧基矽烷、2-苯基甲基胺基丙基三甲氧基矽烷、2-苯基甲基胺基丙基甲基二甲氧基矽烷、2-苯基甲基胺基丙基二甲基甲氧基矽烷、2-苯基甲基胺基丙基三乙氧基矽烷、2-苯基甲基胺基丙基甲基二乙氧基矽烷、2-苯基甲基胺基丙基二甲基乙氧基矽烷、2-哌啶基丙基三甲氧基矽烷、2-哌啶基丙基甲基二甲氧基矽烷、2-哌啶基丙基二甲基甲氧基矽烷、2-哌啶基丙基三乙氧基矽烷、2-哌啶基丙基甲基二乙氧基矽烷、2-哌啶基丙基二甲基乙氧基矽烷、2-嗎啉基丙基三甲氧基矽烷、2-嗎啉基丙基甲基二甲氧基矽烷、2-嗎啉基丙基二甲基甲氧基矽烷、2-嗎啉基丙基三乙氧基矽烷、2-嗎啉基丙基甲基二乙氧基矽烷、2-嗎啉基丙基二甲基乙氧基矽烷、2-(4-甲基哌嗪-1-基)丙基三甲氧基矽烷、2-(4-甲基哌嗪-1-基)丙基甲基二甲氧基矽烷、2-(4-甲基哌嗪-1-基)丙基二甲基甲氧基矽烷、2-(4-甲基哌嗪-1-基)丙基三乙氧基矽烷、2-(4-甲基哌嗪-1-基)丙基甲基二乙氧基矽烷、2-(4-甲基哌嗪-1-基)丙基二甲基乙氧基矽烷等。
本發明中之以上述通式(1)表示之含氮有機氧矽烷化合物與以上述通式(2)表示之含氮有機氧矽烷
化合物之組成比,為以上述通式(1)表示之含氮有機氧矽烷化合物90~99質量份,以上述通式(2)表示之含氮有機氧矽烷化合物1~10質量份,更佳以上述通式(1)表示之含氮有機氧矽烷化合物90~95質量份,以上述通式(2)表示之含氮有機氧矽烷化合物5~10質量份。
本發明中之包含含氮有機氧矽烷化合物的組成物之製造方法例示為例如在無機酸之銨鹽存在下使用鉑觸媒使以下述通式(3)所示之包含含氮不飽和鍵之化合物與以下述通式(4)表示之氫有機氧矽烷化合物進行氫矽烷基化之方法,
(式中,R1、R2、R3與上述相同),HSiR4 n(OR5)3-n (4)
(式中,R4、R5、n與上述相同)。
作為以上述通式(3)表示之包含含氮不飽和鍵之化合物具體例示為二甲基烯丙基胺、二乙基烯丙基胺、二丙基烯丙基胺、二丁基烯丙基胺、苯基甲基烯丙基胺、N-烯丙基哌啶、N-烯丙基嗎啉、1-烯丙基-4-甲基哌嗪等。
以上述通式(4)表示之氫有機氧矽烷化合物
具體例示為三甲氧基矽烷、甲基二甲氧基矽烷、二甲基甲氧基矽烷、三乙氧基矽烷、甲基二乙氧基矽烷、二甲基乙氧基矽烷等。
以上述通式(3)表示之包含含氮不飽和鍵之化合物與以上述通式(4)表示之氫有機氧矽烷化合物之調配比並無特別限制,但就反應性、生產性之觀點而言,相對於以通式(3)表示之化合物1莫耳,以通式(4)表示之化合物較佳在0.1~4莫耳,特佳在0.2~2莫耳之範圍。
上述反應中使用之無機酸之銨鹽例示為例如氯化銨、硫酸銨、硫酸氫銨、硝酸銨、磷酸二氫銨、磷酸氫二銨、磷酸銨、二亞磷酸銨、碳酸銨、碳酸氫銨、硫化銨、硼酸銨、硼氟化銨等,尤其就提高反應性、異構物之生成比抑制效果之觀點而言,較佳為pKa為2以上之無機酸之銨鹽,特佳為碳酸銨、碳酸氫銨。
無機酸之銨鹽之使用量並無特別限制,但就反應性、選擇性、生產性之觀點而言,相對於以通式(3)表示之含有不飽和鍵之化合物1莫耳,較佳為0.00001~0.1莫耳,特佳為0.0001莫耳~0.05莫耳之範圍。
作為上述反應中所用之鉑觸媒例示為氯化鉑酸、氯化鉑酸之醇溶液、鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之甲苯或二甲苯溶液、肆三苯膦鉑、二氯雙三苯膦鉑、二氯雙乙腈鉑、二氯雙苯甲腈鉑、二氯環辛
二烯鉑、鉑-活性碳等。
鉑觸媒之使用量並無特別限制,但就反應性、生產性之觀點而言,相對於以通式(3)表示之包含含氮不飽和鍵化合物1莫耳,較佳為0.000001~0.01莫耳,特佳為0.00001~0.001莫耳之範圍。
上述反應之反應溫度並無特別限制,但較佳為0~200℃,特佳為20~150℃,反應時間亦無特別限制,但較佳為1~40小時,特佳為1~20小時。反應環境較佳為氮、氬等惰性氣體環境。
又,上述反應亦可在無溶劑下進行,但亦可使用溶劑。作為使用之溶劑例示為戊烷、己烷、環己烷、庚烷、異辛烷、苯、甲苯、二甲苯等烴系溶劑,二***、四氫呋喃、二噁烷等醚系溶劑,乙酸乙酯、乙酸丁酯等酯系溶劑,乙腈、N,N-二甲基甲醯胺、N-甲基吡咯啶酮等非質子系極性溶劑,二氯甲烷、氯仿等氯化烴系溶劑等。該等溶劑可單無使用1種,或亦可混合2種以上使用。
藉由上述反應獲得之包含含氮聚矽氧化合物之組成物依據其目的品質,亦可利用蒸餾、過濾、洗淨、管柱分離、固體吸附等各種純化法進一步純化使用。為了去除觸媒等之微量雜質而成為高純度,較佳以蒸餾純化。
以下,列示實施例及比較例具體說明本發明,但本發明並不受限於下述之實施例。
於具備攪拌機、回流器、滴加漏斗及溫度計之燒瓶中饋入二甲基烯丙基胺97.9g(1.15莫耳)、1.5g(以Pt計為45mg)之鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之3質量%甲苯溶液、碳酸氫銨1.8g(0.023莫耳),加熱至55℃。使內溫安定後,在7小時內滴加三甲氧基矽烷140.6g(1.15莫耳),且在該溫度下攪拌1小時。反應液以氣體層析及GC-MS分析,生成3-二甲胺基丙基三甲氧基矽烷與2-二甲胺基丙基三甲氧基矽烷,生成比為92.8:7.2。反應液經蒸餾,獲得164.5g之沸點78-81℃/1.0kPa之餾份。餾份中含有3-二甲胺基丙基三甲氧基矽烷92.5質量%、2-二甲胺基丙基三甲氧基矽烷6.7質量%。
於具備攪拌機、回流器、滴加漏斗及溫度計之燒瓶中饋入二甲基烯丙基胺85.2g(1.0莫耳)、1.3g(以Pt計為39mg)之鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之3質量%甲苯溶液、碳酸氫銨1.6g(0.02莫耳),加熱至55℃。使內溫安定後,在9小時內滴加三乙氧基矽烷164.3g(1.0莫耳),且在該溫度下攪拌8小時。反應液以氣體層析及GC-MS分析,生成3-二甲胺基丙基三乙氧基矽烷與2-二甲胺基丙基三乙氧基矽烷,生成比為
91.7:8.3。反應液經蒸餾,獲得180.7g之沸點93-96℃/1.0kPa之餾份。餾份中含有3-二甲胺基丙基三乙氧基矽烷92.3質量%、2-二甲胺基丙基三乙氧基矽烷6.8質量%。
除了未添加碳酸氫銨以外,餘進行與實施例1相同之反應,反應液中之3-二甲胺基丙基三甲氧基矽烷與2-二甲胺基丙基三甲氧基矽烷之生成比為63.8:36.2。反應液經蒸餾,獲得156.5g之沸點77-81℃/1.0kPa之餾份。餾份中含有3-二甲胺基丙基三甲氧基矽烷65.5質量%、2-二甲胺基丙基三甲氧基矽烷33.5質量%。
除了未添加碳酸氫銨以外,餘進行與實施例2相同之反應,反應液中之3-二甲胺基丙基三乙氧基矽烷與2-二甲胺基丙基三乙氧基矽烷之生成比為56.7:43.3。反應液經蒸餾,獲得175.4g之沸點92-96℃/1.0kPa之餾份。餾份中含有3-二甲胺基丙基三乙氧基矽烷57.9質量%、2-二甲胺基丙基三乙氧基矽烷41.1質量%。
於具備攪拌機、回流器、滴加漏斗及溫度計之燒瓶中饋入二甲基烯丙基胺127.8g(1.5莫耳)、2.0g(以Pt計
為60mg)之鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之3質量%甲苯溶液、碳酸氫銨1.2g(0.015莫耳),加熱至45℃。使內溫安定後,在6小時內滴加甲基二甲氧基矽烷159.3g(1.5莫耳),且在該溫度下攪拌6小時。反應液以氣體層析及GC-MS分析,生成3-二甲胺基丙基甲基二甲氧基矽烷與2-二甲胺基丙基甲基二甲氧基矽烷,生成比為90.7:9.3。反應液經蒸餾,獲得223.4g之沸點85-89℃/2.5kPa之餾份。餾份中含有3-二甲胺基丙基甲基二甲氧基矽烷91.4質量%、2-二甲胺基丙基甲基二甲氧基矽烷8.0質量%。
除了未添加碳酸氫銨以外,餘進行與實施例3相同之反應,反應液中之3-二甲胺基丙基甲基二甲氧基矽烷與2-二甲胺基丙基甲基二甲氧基矽烷之生成比為56.4:43.6。反應液經蒸餾,獲得218.8g之沸點84-89℃/2.5kPa之餾份。餾份中含有3-二甲胺基丙基甲基二甲氧基矽烷58.1質量%、2-二甲胺基丙基甲基二甲氧基矽烷41.0質量%。
Claims (3)
- 如請求項1之組成物,其中R1、R2為甲基,R3為亞甲基。
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