GB1016529A - Novel organotin compounds - Google Patents
Novel organotin compoundsInfo
- Publication number
- GB1016529A GB1016529A GB1710364A GB1710364A GB1016529A GB 1016529 A GB1016529 A GB 1016529A GB 1710364 A GB1710364 A GB 1710364A GB 1710364 A GB1710364 A GB 1710364A GB 1016529 A GB1016529 A GB 1016529A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isocyanate
- product
- reaction
- compound
- active hydrogen
- 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 13
- 239000000047 product Substances 0.000 abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 9
- 239000012948 isocyanate Substances 0.000 abstract 8
- 239000005056 polyisocyanate Substances 0.000 abstract 6
- 229920001228 polyisocyanate Polymers 0.000 abstract 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 4
- 125000000732 arylene group Chemical group 0.000 abstract 4
- 239000003701 inert diluent Substances 0.000 abstract 4
- 229910052718 tin Inorganic materials 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 abstract 2
- QSGUSUIWSCEITD-UHFFFAOYSA-L 2,2-dihydroxyacetate dioctyltin(2+) Chemical compound OC(C(=O)[O-])O.C(CCCCCCC)[Sn+2]CCCCCCCC.OC(C(=O)[O-])O QSGUSUIWSCEITD-UHFFFAOYSA-L 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 2
- WWEXBGFSEVKZNE-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=CC2=CC=CC=C21 Chemical compound N=C=O.N=C=O.C1=CC=CC2=CC=CC=C21 WWEXBGFSEVKZNE-UHFFFAOYSA-N 0.000 abstract 2
- FSFMRMVHSRFBLQ-UHFFFAOYSA-L OC(C(=O)[O-])O.C(CCC)[Sn+2]CCCC.OC(C(=O)[O-])O Chemical compound OC(C(=O)[O-])O.C(CCC)[Sn+2]CCCC.OC(C(=O)[O-])O FSFMRMVHSRFBLQ-UHFFFAOYSA-L 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 abstract 2
- KUCPUSUXIGWHFB-UHFFFAOYSA-N diphenyltin Chemical compound C=1C=CC=CC=1[Sn]C1=CC=CC=C1 KUCPUSUXIGWHFB-UHFFFAOYSA-N 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract 2
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- -1 phenylene, tolylene Chemical group 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
- 229920002635 polyurethane Polymers 0.000 abstract 2
- 239000002243 precursor Substances 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/1077—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing polyurethane
-
- 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
- C07F7/22—Tin 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)
Abstract
The invention comprises monomeric or polymeric organotin compounds which are the product of the reaction between an organic polyisocyanate and a compound RaSnX4-a, wherein a is 1, 2 or 3, R is an alkyl, aryl, alkenyl, cycloalkyl or aralkyl radical and X is a group containing at least one Zerewitinoff active hydrogen atom and bound to the tin atom through a sulphur or oxygen atom. The group X is preferably that represented by the formula YR1Zc, wherein Y is a divalent residue such as -O-, -S- or -COO- linking a hydrocarbon residue R1, substituted by C groups Z containing the active hydrogen atom, to the tin atom. Z may be an amine, hydroxyl, mercaptan or hydroxyl group. Preferably all Z groups are the same and are attached to different carbon atoms of R1. Numerous examples of X are listed, and compounds prepared from dibutyltin bis-hydroxyacetate, dibutyltin bis-hydroxy-ethylmercaptide, di-n-octyltin bis-hydroxyacetate, diphenyltin bis-hydroxyethylmercaptide and triphenyltin dimethylol propionate are claimed. When c is one and a is three, the organotin compound contains only one active hydrogen atom and the product is a monomer. When c is greater than one, typically 2, or when a is less than 3, or both the product is a polymer. The compound RaSnX4-a may be prepared by the reaction of e.g. an organotin oxide, hydroxide or halide with a compound MX, wherein M is metal, ammonium or hydrogen, at e.g. 60-120 DEG C. in the optional presence of an inert diluent and removing the inorganic by-product. The product may be isolated or used without separation. Numerous precursors of RaSn4-a are listed. The organic polyisocyanate may be an alkylene di-isocyanate such as hexamethylene or decamethylene di-isocyanate, an arylene di-isocyanate such as phenylene, tolylene or naphthalene di-isocyanate, or a tri-isocyanate such as the product of reaction of 3 moles of an arylene di-isocyanate with one mole of hexanetriol or trimethylol propane. Sufficient polyisocyanate is supplied to react with all of the active hydrogen atoms, preferably up to ten mole per cent excess. An inert diluent may be employed or a conventional polyurethane catalyst, or the reaction may be initiated by heating.ALSO:The invention comprises monomeric or polymeric organotin compounds which are the product of the reaction between an organic polyisocyanate and a compound RaSnX4-a, wherein a is 1, 2 or 3, R is an alkyl, aryl, alkenyl, cycloalkyl, alkaryl or aralkyl radical, and X is a group containing at least one Zerewitinoff active hydrogen atom and bound to the tin atom through a sulphur or oxygen atom. The group X is preferably that represented by the formula YR1Zc, wherein Y is a divalent residue such as -O-, -S- or -OOC- linking a hydrocarbon residue R1, substituted by c groups Z containing the active hydrogen atom, to the tin atom. Z may be an amine, hydroxyl, mercaptan or carboxyl group. Preferably all Z groups are the same, and are attached to different carbon atoms of R1. Numerous examples of X are listed, and compounds prepared from dibutyltin bis-hydroxyacetate, dibutyltin bis-hydroxy-ethylmercaptide, di-n-octyltin bis-hydroxyacetate, diphenyltin bis-hydroxyethylmercaptide and triphenyltin dimethylol propionate are claimed. The compound RaSnX4-a may be prepared by the reaction of e.g. an organotin oxide, hydroxide or halide with a compound MX, wherein M is metal, ammonium or hydrogen at e.g. 60 DEG -120 DEG C. in the optional presence of an inert diluent and removing the inorganic byproduct. The product may be isolated or used without separation. Numerous precursors of RaSnX4-a are listed. The organic polyisocyanate may be an alkylene di-isocyanate such as hexamethylene or decamethylene di-isocyanate, an arylene di-isocyanate such as phenylene, tolylene or naphthalene di-isocyanates, or a tri-isocyanate such as the products of reaction of three moles of an arylene di-isocyanate with one mole of hexanetriol or trimethylol propane, or mixtures thereof. Sufficient polyisocyanate is supplied to react with all of the reactive hydrogen atoms, and preferably up to ten mole per cent excess. An inert diluent may be employed, or a conventional polyurethane catalyst, or one reaction may be initiated by heating. When c in the formula YR1Zc is 1 and a in RaSnX4-a is 3, the organotin compound contains only one active hydrogen atom and the product is a monomer. When c is greater than 1, typically 2, or when a is less than 3, or both, the product is a polymer.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27961363A | 1963-05-10 | 1963-05-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1016529A true GB1016529A (en) | 1966-01-12 |
Family
ID=23069704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1710364A Expired GB1016529A (en) | 1963-05-10 | 1964-04-24 | Novel organotin compounds |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4826002B1 (en) |
| CH (1) | CH471836A (en) |
| DE (1) | DE1520387A1 (en) |
| GB (1) | GB1016529A (en) |
| NL (1) | NL6405136A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3511803A (en) * | 1966-02-15 | 1970-05-12 | Nitto Kasei Co Ltd | Hindered phenolic-containing organotin stabilizer for polymers |
| US7723318B2 (en) | 2004-03-31 | 2010-05-25 | Mitsui Chemicals, Inc. | Polymerizable compound and use thereof |
| US7772348B2 (en) | 2004-11-16 | 2010-08-10 | Mitsui Chemicals, Inc. | Metal-containing compound and use thereof |
-
1964
- 1964-04-24 GB GB1710364A patent/GB1016529A/en not_active Expired
- 1964-05-08 NL NL6405136A patent/NL6405136A/xx unknown
- 1964-05-08 DE DE19641520387 patent/DE1520387A1/en active Pending
- 1964-05-08 JP JP2583464A patent/JPS4826002B1/ja active Pending
- 1964-05-08 CH CH603464A patent/CH471836A/en not_active IP Right Cessation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3511803A (en) * | 1966-02-15 | 1970-05-12 | Nitto Kasei Co Ltd | Hindered phenolic-containing organotin stabilizer for polymers |
| US7723318B2 (en) | 2004-03-31 | 2010-05-25 | Mitsui Chemicals, Inc. | Polymerizable compound and use thereof |
| US7906494B2 (en) | 2004-03-31 | 2011-03-15 | Mitsui Chemicals, Inc. | Polymerizable compound and use thereof |
| US7998944B2 (en) | 2004-03-31 | 2011-08-16 | Mitsui Chemicals, Inc. | Polymerizable compound and use thereof |
| US7772348B2 (en) | 2004-11-16 | 2010-08-10 | Mitsui Chemicals, Inc. | Metal-containing compound and use thereof |
| CN101061160B (en) * | 2004-11-16 | 2011-02-16 | 三井化学株式会社 | Metal-containing compound and use thereof |
| US7951968B2 (en) | 2004-11-16 | 2011-05-31 | Mitsui Chemicals, Inc. | Metal-containing compound and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CH471836A (en) | 1969-04-30 |
| NL6405136A (en) | 1964-11-11 |
| JPS4826002B1 (en) | 1973-08-03 |
| DE1520387A1 (en) | 1969-03-27 |
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