GB1056542A - Organobismuth compounds - Google Patents
Organobismuth compoundsInfo
- Publication number
- GB1056542A GB1056542A GB1710264A GB1710264A GB1056542A GB 1056542 A GB1056542 A GB 1056542A GB 1710264 A GB1710264 A GB 1710264A GB 1710264 A GB1710264 A GB 1710264A GB 1056542 A GB1056542 A GB 1056542A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- bis
- ooc
- unsubstituted
- organobismuth
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 8
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000002950 monocyclic group Chemical group 0.000 abstract 6
- ARWJSDBKJGYWET-UHFFFAOYSA-N phenylbismuth Chemical compound [Bi]C1=CC=CC=C1 ARWJSDBKJGYWET-UHFFFAOYSA-N 0.000 abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 3
- 229920000570 polyether Polymers 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002184 metal Chemical group 0.000 abstract 2
- 229910052751 metal Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- 229920001228 polyisocyanate Polymers 0.000 abstract 2
- 239000005056 polyisocyanate Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 229920002635 polyurethane Polymers 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 abstract 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 2
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 abstract 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 abstract 2
- BSVXBXNZZNYAIK-UHFFFAOYSA-L 2,2,2-triphenyl-1,3,2$l^{5}-dioxabismetan-4-one Chemical compound O1C(=O)O[Bi]1(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BSVXBXNZZNYAIK-UHFFFAOYSA-L 0.000 abstract 1
- VBBUJJRPEHFAES-UHFFFAOYSA-N 4-aminobenzoic acid;triphenylbismuthane Chemical compound NC1=CC=C(C(O)=O)C=C1.NC1=CC=C(C(O)=O)C=C1.C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 VBBUJJRPEHFAES-UHFFFAOYSA-N 0.000 abstract 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 abstract 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- NZKWCMHPXDCEER-UHFFFAOYSA-N CCCCCCCC[Bi]CCCCCCCC Chemical compound CCCCCCCC[Bi]CCCCCCCC NZKWCMHPXDCEER-UHFFFAOYSA-N 0.000 abstract 1
- FXLPTIALOJOMIR-UHFFFAOYSA-L OC(C(=O)[O-])O.C1(=CC=CC=C1)[Bi+2].OC(C(=O)[O-])O Chemical compound OC(C(=O)[O-])O.C1(=CC=CC=C1)[Bi+2].OC(C(=O)[O-])O FXLPTIALOJOMIR-UHFFFAOYSA-L 0.000 abstract 1
- AMHKUCNWOUVTRU-UHFFFAOYSA-L OC1=CC=C(C(=O)[O-])C=C1.OC1=CC=C(C(=O)[O-])C=C1.C1(=CC=CC=C1)[Bi+2] Chemical compound OC1=CC=C(C(=O)[O-])C=C1.OC1=CC=C(C(=O)[O-])C=C1.C1(=CC=CC=C1)[Bi+2] AMHKUCNWOUVTRU-UHFFFAOYSA-L 0.000 abstract 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 abstract 1
- 229920002396 Polyurea Polymers 0.000 abstract 1
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 229940064734 aminobenzoate Drugs 0.000 abstract 1
- 229960004050 aminobenzoic acid Drugs 0.000 abstract 1
- IROPSCDCCZHLDE-DPMBMXLASA-N azanium;(z,12r)-12-hydroxyoctadec-9-enoate Chemical compound N.CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IROPSCDCCZHLDE-DPMBMXLASA-N 0.000 abstract 1
- 230000003385 bacteriostatic effect Effects 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- LVUMTHVAWMIGTO-UHFFFAOYSA-M chloro(dioctyl)bismuthane Chemical compound C(CCCCCCC)[Bi](Cl)CCCCCCCC LVUMTHVAWMIGTO-UHFFFAOYSA-M 0.000 abstract 1
- 239000006260 foam Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 235000010292 orthophenyl phenol Nutrition 0.000 abstract 1
- -1 pentachlorophenol Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920001451 polypropylene glycol Polymers 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 239000011496 polyurethane foam Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 abstract 1
- 229940066675 ricinoleate Drugs 0.000 abstract 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract 1
- KVSKGMLNBAPGKH-UHFFFAOYSA-N tribromosalicylanilide Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC1=CC=C(Br)C=C1 KVSKGMLNBAPGKH-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3897—Low-molecular-weight compounds having heteroatoms other than oxygen containing heteroatoms other than oxygen, halogens, nitrogen, sulfur, phosphorus or silicon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Organobismuth compounds of formulae RaBiX3- a and Ar3BiX2 where a is 1 o 2, R (which may contain an inert substituent) is an alkyl or alkenyl group of <20C, a cycloalkyl group or monocyclic aryl group, Ar is an unsubstituted or inertly substituted monocyclic aryl group; and X is a group of formula -OOC(R1)OH, -OOC(R1)NH2 or -S(R1)OH, R1 being an unsubstituted or substituted divalent saturated or ethylenically unsaturated aliphatic group containing <20C, a phenylene or divalent araliphatic group are prepared by (a) RaBiZ3- a + (3-a)MX -> RaBiX3- a + (3-a)MZ, or (b) R3Bi + (3-a)HX -> RaBiX3- a + (3-a)RH where R, R1, a and X are as defined above, M is hydrogen or a metal, and Z is a replaceable group such as -OH,-U or -O-, or (c) Ar3BiZ12 + 2MX -> Ar3BiX2 + 2MZ1 where Ar, R1, M and X are as defined above and Z1 is a replaceable group such as O or CO3. In preparations the following compounds were prepared (1) phenylbismuth bis (p-hydroxybenzoate) from triphenylbismuth and p-hydroxybenzoic acid, (2) triphenylbismuth bis (p-aminobenzoate) from triphenylbismuth carbonate and p-aminobenzoic acid, (3) dioctylbismuth ricinoleate from dioctylbismuth chloride and ammonium ricinoleate and (4) phenylbismuth bis (2-hydroxyethylmercaptide) from triphenylbismuth with 2-mercaptoethanol.ALSO:A polymer containing organobismuth groups is prepared by reacting an organic polyisocyanate with an organobismuth compound of formula RaBiX3- a or Ar3BiX2 where a is 1 or 2, R (which may be substituted by an inert group) is an alkyl or alkenyl group of <20 C, a cycloalkyl group or monocyclic aryl group; Ar is an unsubstituted or inertly substituted monocyclic aryl group; and X is a group of the formula -OOC(R1)OH, -OOC(R1)NH2 or -S(R1)OH, R1 being an unsubstituted or substituted divalent saturated or ethylenically unsaturated aliphatic group of <20 C, a phenylene or divalent or aliphatic group. The reaction mixture may also include a polyether a polyester, e.g. polypropylene oxide or the hydroxyl terminated polyester of adipic acid, ethylene glycol and propylene glycol. Foamed polyurethanes or polyureas may be obtained by incorporating the organobismuth compounds in foam forming recipe. In examples tolylene diisocyanate was reacted with (1) phenylbismuth bis-(2-hydroxyethyl-mercaptide), (2) phenylbismuth bis-hydroxyacetate, (3) hydroxyl terminated polyether and phenylbismuth bis-(2-hydroxyethylmercaptide) in the presence of stannous octoate, (4) hydroxyl terminated polyether, water and phenylbismuth bis-(2-hydroxyethylmercaptide) in the presence of silicone, N-ethylmorpholine, stannous octoate and triethylene diamine to form a polyurethane foam, (5) phenylbismuth bis-(f-aminobenzoate) with the other reactants as in (4) to give a polyurethane containing urea linkages, (6) phenyl bis-(f-hydroxybenzoate) in toluene.ALSO:A bacteriostatic composition comprises a carrier and as an active ingredient a polymer containing organobismuth groups prepared by reacting an organic polyisocyanate with an organobismuth compound of formula Ra Bi X3-a or Ar3 Bi X2 wherein a is 1 or 2, R (which may contain an inert substituent) is an alkyl or alkenyl group containing <20C, a cycloalkyl or a monocyclic aryl group; Ar is an unsubstituted or inertly substituted monocyclic aryl group; and X a group of formula -OOC(R1) OH, -OOC(R1)NH2, or -S(R1)OH, R1 being an unsubstituted or substituted divalent saturated or ethylenically unsaturated aliphatic group containing <20C, a phenylene group or divalent araliphatic group. The composition may also contain other known active compounds, e.g. pentachlorophenol, a triorganotin compound, copper 8 quinolinolate, a bisphenol, O phenyl phenol, a polybrominated salicylanilide or a metal (e.g. Zn) dialkyldithiocarbamate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28010263A | 1963-05-13 | 1963-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1056542A true GB1056542A (en) | 1967-01-25 |
Family
ID=23071682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1710264A Expired GB1056542A (en) | 1963-05-13 | 1964-04-24 | Organobismuth compounds |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4822693B1 (en) |
| CH (1) | CH446262A (en) |
| DE (1) | DE1520385C3 (en) |
| GB (1) | GB1056542A (en) |
| IT (1) | IT972006B (en) |
| NL (1) | NL143603B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009029626A1 (en) * | 2007-08-27 | 2009-03-05 | Dow Global Technologies Inc. | Catalysis of viscoelastic foams with bismuth salts |
| WO2021097159A1 (en) * | 2019-11-13 | 2021-05-20 | University Of Hawaii | Method for preparing heteroleptic triarylbismuthanes and compounds produced by the same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19635419C1 (en) * | 1996-08-23 | 1998-08-20 | Schering Ag | Bismuth dendrimers and their use as X-ray contrast media |
-
1964
- 1964-04-24 GB GB1710264A patent/GB1056542A/en not_active Expired
- 1964-04-29 CH CH560064A patent/CH446262A/en unknown
- 1964-05-06 DE DE19641520385 patent/DE1520385C3/en not_active Expired
- 1964-05-11 JP JP39026390A patent/JPS4822693B1/ja active Pending
- 1964-05-12 IT IT1095664A patent/IT972006B/en active
- 1964-05-13 NL NL6405308A patent/NL143603B/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009029626A1 (en) * | 2007-08-27 | 2009-03-05 | Dow Global Technologies Inc. | Catalysis of viscoelastic foams with bismuth salts |
| WO2021097159A1 (en) * | 2019-11-13 | 2021-05-20 | University Of Hawaii | Method for preparing heteroleptic triarylbismuthanes and compounds produced by the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CH446262A (en) | 1968-03-15 |
| NL143603B (en) | 1974-10-15 |
| CH560064A4 (en) | 1967-07-31 |
| NL6405308A (en) | 1964-11-16 |
| DE1520385A1 (en) | 1969-02-20 |
| JPS4822693B1 (en) | 1973-07-07 |
| DE1520385B2 (en) | 1973-08-09 |
| DE1520385C3 (en) | 1974-04-04 |
| IT972006B (en) | 1974-05-20 |
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