CA1274532A - Carbamates de silyle et leur utilisation pour la preparation de bis(aminoalkyl)disiloxanes - Google Patents

Carbamates de silyle et leur utilisation pour la preparation de bis(aminoalkyl)disiloxanes

Info

Publication number: CA1274532A
Authority: CA; Canada
Prior art keywords: formula; methyl; bis; silyl carbamate; aminoalkyl
Prior art date: 1985-08-22
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.): Expired

Application number

CA000516668A

Other languages

English (en)

Inventor

Jimmy L. Webb

Cathryn E. Olsen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

General Electric Co

Original Assignee

General Electric Co

Priority date (The priority date 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 date listed.)

1985-08-22

Filing date

1986-08-22

Publication date

1990-09-25

1985-08-22 Priority claimed from US06/768,255 external-priority patent/US4631346A/en

1986-08-22 Application filed by General Electric Co filed Critical General Electric Co

1990-09-25 Application granted granted Critical

1990-09-25 Publication of CA1274532A publication Critical patent/CA1274532A/fr

Status Expired legal-status Critical Current

Links

DRNXZGJGRSUXHW-UHFFFAOYSA-N silyl carbamate Chemical class NC(=O)O[SiH3] DRNXZGJGRSUXHW-UHFFFAOYSA-N 0.000 title claims abstract description 30
125000004103 aminoalkyl group Chemical group 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title abstract description 16
239000000203 mixture Substances 0.000 claims abstract description 39
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 22
238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 14
229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 11
239000001569 carbon dioxide Substances 0.000 claims abstract description 11
238000000034 method Methods 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 22
239000003054 catalyst Substances 0.000 claims description 17
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
150000003058 platinum compounds Chemical class 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 2
BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical class [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 4
238000006460 hydrolysis reaction Methods 0.000 abstract description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 3
DFIMTDUKYCFYKP-UHFFFAOYSA-N N-dimethylsilylprop-2-en-1-amine Chemical compound C[SiH](C)NCC=C DFIMTDUKYCFYKP-UHFFFAOYSA-N 0.000 abstract description 3
230000007062 hydrolysis Effects 0.000 abstract description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 13
229910052697 platinum Inorganic materials 0.000 description 10
-1 carbomethoxyphenyl Chemical group 0.000 description 9
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 6
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 4
ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 4
GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical group NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 3
239000005046 Chlorosilane Substances 0.000 description 3
238000007323 disproportionation reaction Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000004642 Polyimide Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229940045985 antineoplastic platinum compound Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical group C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 2
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920001721 polyimide Polymers 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
239000010703 silicon Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 description 1
ASVKKRLMJCWVQF-UHFFFAOYSA-N 3-buten-1-amine Chemical compound NCCC=C ASVKKRLMJCWVQF-UHFFFAOYSA-N 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
JMXWYCKNTYDKAX-UHFFFAOYSA-N N,N-bis(dimethylsilyl)prop-2-en-1-amine Chemical compound C[SiH](C)N([SiH](C)C)CC=C JMXWYCKNTYDKAX-UHFFFAOYSA-N 0.000 description 1
XCONYYPSSUCMPU-UHFFFAOYSA-N N-dimethylsilyl-N-ethylprop-2-en-1-amine Chemical compound C[SiH](N(CC)CC=C)C XCONYYPSSUCMPU-UHFFFAOYSA-N 0.000 description 1
ZKONNTLRFKQMJE-UHFFFAOYSA-N N-dimethylsilylprop-2-en-1-amine silane Chemical compound [SiH4].C[SiH](C)NCC=C ZKONNTLRFKQMJE-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
JRAGWRJBQKMKAZ-UHFFFAOYSA-N [SiH4].O=C=O Chemical compound [SiH4].O=C=O JRAGWRJBQKMKAZ-UHFFFAOYSA-N 0.000 description 1
FKTVDUYYZGEXJA-UHFFFAOYSA-N [SiH4].[SiH3]N[SiH3] Chemical compound [SiH4].[SiH3]N[SiH3] FKTVDUYYZGEXJA-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004802 cyanophenyl group Chemical group 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000006159 dianhydride group Chemical group 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
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 1
HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001601 polyetherimide Polymers 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

CA000516668A 1985-08-22 1986-08-22 Carbamates de silyle et leur utilisation pour la preparation de bis(aminoalkyl)disiloxanes Expired CA1274532A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/768,255 US4631346A (en)	1985-03-04	1985-08-22	Silyl carbamates and their use in the preparation of bis (aminoalkyl) disiloxanes
US768,255		1985-08-22

Publications (1)

Publication Number	Publication Date
CA1274532A true CA1274532A (fr)	1990-09-25

Family

ID=25081965

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000516668A Expired CA1274532A (fr)	1985-08-22	1986-08-22	Carbamates de silyle et leur utilisation pour la preparation de bis(aminoalkyl)disiloxanes

Country Status (1)

Country	Link
CA (1)	CA1274532A (fr)

1986
- 1986-08-22 CA CA000516668A patent/CA1274532A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1995-03-25	MKLA	Lapsed

Publication	Publication Date	Title
US5026890A (en)	1991-06-25	Method and intermediates for preparation of bis(aminoalkyl)polydiorganosiloxanes
US4631346A (en)	1986-12-23	Silyl carbamates and their use in the preparation of bis (aminoalkyl) disiloxanes
US4584393A (en)	1986-04-22	Bis(aminoalkyl)disiloxanes and method and intermediates for their preparation
US4981988A (en)	1991-01-01	Organosiloxane compound with one end stopped with an aminoalkyl group and a manufacturing method thereof
US5300613A (en)	1994-04-05	Fluorine-containing organosilicon compounds
AU602057B2 (en)	1990-09-27	Novel aminohydrocarbyl-substituted ketoximosilanes
US6297383B1 (en)	2001-10-02	Silicone monomers and oligomers having a carboxyl functional group thereon
CA1274532A (fr)	1990-09-25	Carbamates de silyle et leur utilisation pour la preparation de bis(aminoalkyl)disiloxanes
EP0402632B1 (fr)	1995-03-08	Composés polyimides aromatiques contenant un groupe silanol, leurs précurseurs et leurs polymères
US5514827A (en)	1996-05-07	Silylated cyclic hydrocarbons and their uses
US5239099A (en)	1993-08-24	Azasilacycloalkyl functional alkoxysilanes and azasilacycloalkyl functional tetramethyldisiloxanes
JPH01305094A (ja)	1989-12-08	ω−シリルアルキニルシラン化合物およびその製造方法
US5157095A (en)	1992-10-20	Hydrosilylation of unsaturated aliphatic isocyanates
CA2272557A1 (fr)	1998-05-28	Monomeres et oligomeres a silicone contenant un groupe fonctionnel carboxyle
JPH01125388A (ja)	1989-05-17	アミドシランおよびアミドシロキサンの製造方法
JPS5970691A (ja)	1984-04-21	水素含有シリルカ−バメ−ト
JP7823771B2 (ja)	2026-03-04	アミノアルキルアルコキシジシロキサン化合物およびアミノアルキルアルコキシオリゴシロキサン化合物を含む組成物ならびにその製造方法
JPS6377886A (ja)	1988-04-08	有機けい素化合物
US5780639A (en)	1998-07-14	Silicone monomers and oligomers having a carboxyl functional group thereon
US3780080A (en)	1973-12-18	Silyl maleates and polysiloxane maleates
US6118014A (en)	2000-09-12	Organofunctional cocyclic siloxanes
US5075475A (en)	1991-12-24	Aromatic polyimide silanol compounds, precursors and polymers thereof
US3778459A (en)	1973-12-11	Silyl maleates and polysiloxane maleates
JPS6017796B2 (ja)	1985-05-07	オルガノポリシロキサンの製造方法
JPS62298594A (ja)	1987-12-25	有機けい素化合物