GB973000A - Organic dimers and higher polymers containing boron-oxygen-boron linkages - Google Patents
Organic dimers and higher polymers containing boron-oxygen-boron linkagesInfo
- Publication number
- GB973000A GB973000A GB3316861A GB3316861A GB973000A GB 973000 A GB973000 A GB 973000A GB 3316861 A GB3316861 A GB 3316861A GB 3316861 A GB3316861 A GB 3316861A GB 973000 A GB973000 A GB 973000A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- tri
- tert
- boron
- dimer
- 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
- 239000000539 dimer Substances 0.000 title abstract 10
- 229920000642 polymer Polymers 0.000 title abstract 6
- VSSOFVGBLTZDEB-UHFFFAOYSA-N [B].[B].[O] Chemical compound [B].[B].[O] VSSOFVGBLTZDEB-UHFFFAOYSA-N 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 125000003118 aryl group Chemical group 0.000 abstract 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- 239000000178 monomer Substances 0.000 abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 4
- 239000004327 boric acid Substances 0.000 abstract 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 3
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical class B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 abstract 3
- 229910052796 boron Inorganic materials 0.000 abstract 3
- 229920006037 cross link polymer Polymers 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 230000000903 blocking effect Effects 0.000 abstract 2
- -1 butoxy borazole Chemical compound 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- WIBYPHGWXYLWQX-UHFFFAOYSA-N methyl 2-bromo-2-chloroacetate Chemical compound COC(=O)C(Cl)Br WIBYPHGWXYLWQX-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000013638 trimer Substances 0.000 abstract 1
Classifications
-
- 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
-
- 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
- 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
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises boron-containing dimers or higher polymers having a boron-oxygen-boron linkage obtainable by condensing under the influence of heat, one or more monomers of the general formula: <FORM:0973000/C1/1> where R is a tertiary alkyl group and each of X and Y, which may be the same or different, is an alkyl group, an aryl group or an aralkyl group or substituted alkyl, aryl or aralkyl group, or X when Y is an aryl group, is an alkoxy group, or X is an alkyl group, an aryl group or an aralkyl group and Y an alkyl group or an aryl group each of which contains a boron atom, e.g. (ButO)2B-C6H4-, and C6H5B(OBut)-C6H4-; or X and Y together with the group >B-O-R in which R is defined as above, form a fully or partly substituted borazole, e.g. a mono-, di- or tri-B-tert.-alkoxy borazole in which at least one alkoxy group is a tert.-alkoxy. The monomer may be refluxed at atmospheric pressure and boric acid may be used as a catalyst. For instance, (C6H5)2-B-O-But on heating gives the dimer (C6H5)2B-O-B(C6H5)2, and C6H5-B-(OBut)2 the dimer C6H5-B(OBut)-OB (OBut)-C6H5. A borazole <FORM:0973000/C1/2> gives <FORM:0973000/C1/3> where R is tert.-alkyl and the R1 groups are each substituted or unsubstituted alkyl, aryl or aralkyl. Continued heating gives rise to linear, branched or cross-linked polymers of formula: <FORM:0973000/C1/4> If intermediates are used containing on one boron atom a blocking group such as alkyl, aryl, substituted amino, alkoxy (other than tert.-alkoxy) or aryloxy, linear polymers are obtained. If two monomers are used which differ in respect of R1, a copolymer is obtained. In examples, (1) tri-B-tert.-butoxy-tri-N-methylborazole made from tri-B-chloro-tri-N-methylborazole and tert.-butanol using triethylamine as base, together with a dimer; (2) the monomer of (1) is heated to form a dimer and a polymer containing 7 borazole units; N-trimethyl-, N-tri-ethyl- and N-tri-n-propyl-B-tri-tert. butoxy borazole and made as in (1); (3) N-trimethyl -B-tri-tert.-butoxy borazole was refluxed with a few mgms of boric acid giving a dimer; (4) the N-triethyl and (5) the N-tri-propyl compounds are converted to the dimer; (9) di-t-butyl phenyl boronate is made from phenyl boron dichloride and tert.-butanol in the presence of triethylamine; the product is refluxed to form a linear dimer and trimer.ALSO:Polymers containing a boron-oxygen-boron linkage are obtainable by condensing under the influence of heat one or more monomers of the general formula <FORM:0973000/C3/1> where R is a tertiary alkyl group and the R1 groups are each a substituted or unsubstituted alkyl, aryl or aralkyl group and may be the same or different. The first product is a dimer but continued heating gives linear, branched or cross-linked polymers fornulated from the units: <FORM:0973000/C3/2> If borazoles containing in place of one OR group a blocking group which may be alkyl, aryl, substituted amine, alkoxy (other than tert.-alkoxy) or aryloxy, linear polymers are obtained. The monomer is preferably heated at atmospheric pressure using boric acid as a catalyst. In examples, N-trimethyl -b - tri-tert.-butoxy borazole is refluxed in the presence of boric acid, to form a cross-linked polymer. The N-triethyl and N-tri-n-propyl compounds give similar products.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3316861A GB973000A (en) | 1961-09-15 | 1961-09-15 | Organic dimers and higher polymers containing boron-oxygen-boron linkages |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3316861A GB973000A (en) | 1961-09-15 | 1961-09-15 | Organic dimers and higher polymers containing boron-oxygen-boron linkages |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB973000A true GB973000A (en) | 1964-10-21 |
Family
ID=10349434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3316861A Expired GB973000A (en) | 1961-09-15 | 1961-09-15 | Organic dimers and higher polymers containing boron-oxygen-boron linkages |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB973000A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112876774A (en) * | 2019-11-29 | 2021-06-01 | 合肥杰事杰新材料股份有限公司 | Polypropylene material and preparation method thereof |
-
1961
- 1961-09-15 GB GB3316861A patent/GB973000A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112876774A (en) * | 2019-11-29 | 2021-06-01 | 合肥杰事杰新材料股份有限公司 | Polypropylene material and preparation method thereof |
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