GB857176A - Preparation of aminoboranes - Google Patents
Preparation of aminoboranesInfo
- Publication number
- GB857176A GB857176A GB20729/59A GB2072959A GB857176A GB 857176 A GB857176 A GB 857176A GB 20729/59 A GB20729/59 A GB 20729/59A GB 2072959 A GB2072959 A GB 2072959A GB 857176 A GB857176 A GB 857176A
- Authority
- GB
- United Kingdom
- Prior art keywords
- borane
- tris
- alkylamino
- radical
- butylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KKAXNAVSOBXHTE-UHFFFAOYSA-N boranamine Chemical class NB KKAXNAVSOBXHTE-UHFFFAOYSA-N 0.000 title 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 6
- 125000003282 alkyl amino group Chemical group 0.000 abstract 5
- TVJORGWKNPGCDW-UHFFFAOYSA-N aminoboron Chemical compound N[B] TVJORGWKNPGCDW-UHFFFAOYSA-N 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 229910000085 borane Inorganic materials 0.000 abstract 3
- 238000005891 transamination reaction Methods 0.000 abstract 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000005001 aminoaryl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- MJFUPLXSCJXXIK-UHFFFAOYSA-N n-[bis(butylamino)boranyl]butan-1-amine Chemical compound CCCCNB(NCCCC)NCCCC MJFUPLXSCJXXIK-UHFFFAOYSA-N 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- FXJDOPDOPGNJEB-UHFFFAOYSA-N 1-bis(2-phenylhydrazinyl)boranyl-2-phenylhydrazine Chemical compound C1(=CC=CC=C1)NNB(NNC1=CC=CC=C1)NNC1=CC=CC=C1 FXJDOPDOPGNJEB-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- VMGCWHHRKPAOLW-UHFFFAOYSA-N N-[butylamino(methyl)boranyl]butan-1-amine Chemical compound CB(NCCCC)NCCCC VMGCWHHRKPAOLW-UHFFFAOYSA-N 0.000 abstract 1
- LUTCEEPEOIJIEI-UHFFFAOYSA-N N-anilinoboranylaniline Chemical compound C1(=CC=CC=C1)NBNC1=CC=CC=C1 LUTCEEPEOIJIEI-UHFFFAOYSA-N 0.000 abstract 1
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004984 aromatic diamines Chemical class 0.000 abstract 1
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical class B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- SFGIOBIGJOFJNW-UHFFFAOYSA-N n-[(tert-butylamino)-phenylboranyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)NB(NC(C)(C)C)C1=CC=CC=C1 SFGIOBIGJOFJNW-UHFFFAOYSA-N 0.000 abstract 1
- FDKMNUKIBSZTAU-UHFFFAOYSA-N n-bis(propan-2-ylamino)boranylpropan-2-amine Chemical compound CC(C)NB(NC(C)C)NC(C)C FDKMNUKIBSZTAU-UHFFFAOYSA-N 0.000 abstract 1
- MBNDZJCFAHJKNZ-UHFFFAOYSA-N n-dianilinoboranylaniline Chemical compound C=1C=CC=CC=1NB(NC=1C=CC=CC=1)NC1=CC=CC=C1 MBNDZJCFAHJKNZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 abstract 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/08—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing boron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
A polymer having as the sole recurring unit the grouping -B(R)-N(Rd)-Re-N(Rc)- is formed by a transamination reaction between a bis (alkylamino) borane, tris (alkylamino) borane, bis (phenylamino) borane, or tris (phenylamino) borane, and a primary or secondary aliphatic or aromatic diamine or triamine, a mixed aliphaticaromatic diamine, or an aminotriazine. A homopolymer having the recurring unit -Re -B(R)-N(Rd)- is formed by a transamination reaction between molecules of an alkyl alkylamino aminoalkyl borane or an aromatic or aliphatic-aromatic analogue thereof, this reaction being effected by heating the aminoborane in question. In the above formulae, R is an alkyl, aryl, alkaryl, aralkyl, aminoalkyl, aminoaryl, aminoalkaryl or aminoarakyl radical, Rc and Rd represent hydrogen atoms, C1-C18 alkyl groups, phenyl, substituted phenyl, alkylamino or phenylamino radicals, and Re is an alkylene, phenylene or other divalent organic radical. Novel polymers specified are those obtained from melamine and tris (isopropylamino)- borane, from hexamethylene diamine and phenyl bis (t-butylamino) borane, and from p-phenylene diamine and tris (n-butylamino)-borane.ALSO:An aminoborane is made by effecting a transamination reaction between an amino-borane having in its molecule one or more amino radicals which are not desired in the product, or a substituted borazole corresponding thereto, and a primary or secondary amine corresponding to an amino radical which is desired in the product. For example R3-zB(N Ra Rb)z-x (NRcRd)x is made from R3-zB (N Ra Rb)z and HN Rc Rd where Z is an integer from 1 to 3, X is less than or equal to Z, R is an alkyl, aryl, alkaryl, aralkyl, aminoalkyl, aminoaryl, amino-alkaryl or aminoaralkyl radical, and Ra, Rb, Rc and Rd are each a hydrogen atom, or a C1-C18 alkyl group, or a phenyl, substituted phenyl, alkylamino or phenylamino radical. The reaction proceeds at room temperature but heating may be advantageous. Tris-(n-butylamino) borane, tris (phenylhydrazino) borane and methyl-bis (n-butylamino) borane are novel compounds. An aminoborane enriched in N15 isotope may be made using an amine enriched in N15 isotope as a reactant.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US857176XA | 1958-06-30 | 1958-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB857176A true GB857176A (en) | 1960-12-29 |
Family
ID=22193490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20729/59A Expired GB857176A (en) | 1958-06-30 | 1959-06-17 | Preparation of aminoboranes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB857176A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297749A (en) * | 1961-04-29 | 1967-01-10 | Bayer Ag | Process for the production of substituted borazoles |
| GB2163761A (en) * | 1984-08-11 | 1986-03-05 | Isoji Taniguchi | Process of preparing organoboron nitride polymer |
| EP2881398A1 (en) | 2013-12-04 | 2015-06-10 | Université de Bordeaux I | Method for preparing aminoarylborane compounds or derivatives thereof |
-
1959
- 1959-06-17 GB GB20729/59A patent/GB857176A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297749A (en) * | 1961-04-29 | 1967-01-10 | Bayer Ag | Process for the production of substituted borazoles |
| GB2163761A (en) * | 1984-08-11 | 1986-03-05 | Isoji Taniguchi | Process of preparing organoboron nitride polymer |
| EP2881398A1 (en) | 2013-12-04 | 2015-06-10 | Université de Bordeaux I | Method for preparing aminoarylborane compounds or derivatives thereof |
| WO2015082592A2 (en) | 2013-12-04 | 2015-06-11 | Universite de Bordeaux | Method for preparing aminoarylborane compounds or derivatives thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3522303A (en) | Phosphorous compounds | |
| GB857176A (en) | Preparation of aminoboranes | |
| GB959144A (en) | Improvements in or relating to siloxanes | |
| US3155628A (en) | Production of polymers containing s-triazine nuclei linked together by a nitrogen atom comprising reacting s-triazines with nitrogen compounds | |
| US4219626A (en) | Accelerators for radical polymerization reactions with initiators free from peroxide groups | |
| GB1382456A (en) | Process for the manufacture of rigid foamed polymers | |
| ES247824A1 (en) | Diphenyl alkylenediamines and methods of preparing the same | |
| US3546141A (en) | Phosphorus-nitrogen polymers and process | |
| ES345756A1 (en) | Novel epoxy curing agents | |
| US5691388A (en) | Method of decomposing polycyanurate-containing materials | |
| GB1012317A (en) | Boron nitrogen polymers | |
| IL59345A0 (en) | Silicone-containing bis-ether and bis-thioether aromatic amines and their manufacture | |
| ES453241A1 (en) | Process for the preparation of stable heterogenous dispersions of polyisocyanate-polyaddition products | |
| US2312694A (en) | Triazine derivatives | |
| US3165481A (en) | Polymeric organoboron compounds | |
| DK303188A (en) | Thermostable block copolymers with sequence structure of imide-amide and urea-siloxane blocks | |
| GB854270A (en) | Polymeric organo-boron compounds and their preparation | |
| US3028368A (en) | Polymeric organo-boron compounds and their preparation | |
| ES259956A1 (en) | Polymeric olefin compositions stabilized with a thiodialkanoic acid ester and a trihydroxyaryl hydrocarbon | |
| GB929221A (en) | Phosphorus and nitrogen containing condensation polymers | |
| US3116316A (en) | Tertiary phosphines and methods of preparing same | |
| US2295562A (en) | Triazine derivatives | |
| US3635947A (en) | Catalytic process for the preparation of monocarbodiimides and isocyanate-monocarbodiimide adducts | |
| GB954201A (en) | Process for the preparation of stabilised linear polyureas | |
| GB859834A (en) | Improvements in or relating to ion-exchange resins |