GB957841A - The preparation of organo-tin compounds and their use as catalysts in the productionof polymethanes - Google Patents
The preparation of organo-tin compounds and their use as catalysts in the productionof polymethanesInfo
- Publication number
- GB957841A GB957841A GB12804/61A GB1280461A GB957841A GB 957841 A GB957841 A GB 957841A GB 12804/61 A GB12804/61 A GB 12804/61A GB 1280461 A GB1280461 A GB 1280461A GB 957841 A GB957841 A GB 957841A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- tert
- butyl
- alkyl
- monohydric
- 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
- 239000003054 catalyst Substances 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 4
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 5
- -1 2-ethylhexyl Chemical group 0.000 abstract 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 abstract 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 230000001413 cellular effect Effects 0.000 abstract 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical group O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 abstract 2
- 229920002635 polyurethane Polymers 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
- 229920005749 polyurethane resin Polymers 0.000 abstract 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 abstract 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 abstract 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 abstract 1
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 abstract 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 abstract 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- 229910000831 Steel Inorganic materials 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000003063 flame retardant Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- 229920001228 polyisocyanate Polymers 0.000 abstract 1
- 239000005056 polyisocyanate Substances 0.000 abstract 1
- 229920001451 polypropylene glycol Polymers 0.000 abstract 1
- 229940079877 pyrogallol Drugs 0.000 abstract 1
- 239000010959 steel Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 abstract 1
- 229910001887 tin oxide Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
-
- 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
- C07F7/2224—Compounds having one or more tin-oxygen linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention comprises organotin compounds of formula: [R1R2Sn(OH)x]mXn where R1 and R2 are the same or different alkyl aralkyl or cycloalkyl groups and X is the residue of an ortho dihydric phenol which may be attached by the hydroxyl oxygen atoms to one or two tin atoms, or the residue of a monohydric phenol having as an ortho substituent to the hydroxyl group an alkyl, aralkyl, cycloalkyl or dialkylaminoalkyl group, the dihydric or monohydric phenol having additional alkyl or dialkylaminoalkyl substituents in the ring if desired, x is 0 or 1, and when x is 0, m is 1 and n is 1 or 2, and in this case when n is 2, the X's may be derived from one monohydric phenol or two different monohydric phenols, and when x is 1, n is 1 and m is 1 or 2. Examples of groups R1+R2 include alkyl groups such as isopropyl, n-butyl, n-hexyl and 2-ethylhexyl, aralkyl groups such as benzyl and phenylethyl and cycloalkyl groups such as cyclohexyl and methylcyclohexyl. Monohydric phenols specified include 2,6-di-tert.-butyl-4-methylphenol, 2-methyl-6-tert. butylphenol, tris-(a -methylbenzyl) phenol, 2-a -methylcyclohexyl-4, 6-dimethylphenol and 2, 4, 6-tris-(dimethylaminomethyl) phenol. Dihydric phenols specified include catechol, tert. butyl-catechol, pyrogallol, 2, 21-dihydroxy-3, 31-di-tert. octyl-5, 51-dimethyldiphenylethane, 2, 21-methylene bis(6-tert. butyl-p-cresol), 4, 41-methylene bis (2, 6-ditert. butyl phenol) and 4, 41-thiobis (6-tert-butyl-o-cresol). The tin oxide may be reacted with the phenol in the absence of a solvent or more conveniently in the presence of a hydrocarbon solvent such as benzene, light petroleum or toluene, preferably between 80 DEG C. and 120 DEG C. The compounds of the invention may be used as catalysts in the preparation of polyurethane resins (see Division C3). Specification 892,137 is referred to.ALSO:Rigid or flexible, cellular or homogeneous polyurethane products may be made by reacting hydroxyl group-containing polymers containing at least two isocyanate-reactive groups per molecule with organic polyisocyanates in the presence of an organotin compound of formula: [R1R2Sn(OH)x]mXn where R1 and R2 are the same or different alkyl, aralkyl or cycloalkyl groups and X is the residue of an orthodihydric phenol which may be attached by the hydroxyl oxygen atoms to one or two tin atoms, or the residue of a monohydric phenol having as an ortho substituent to the hydroxyl group an alkyl, aralkyl, cycloalkyl or dialkylaminoalkyl group, the dihydric or monohydric phenol having additional alkyl or dialkylaminoalkyl substituents in the ring if desired, x is 0 or 1, and when x is 0, m is 1 and n is 1 or 2, and in this case when n is 2, the x's may be derived from one monohydric phenol or two different monohydric phenols, and when x is 1, n is 1 and m is 1 or 2. The hydroxyl-containing polymer may be a polyester, polyesteramide or polyether or mixtures thereof. Lists of suitable polymers and organic isocyanates are given. Foamed products are obtained by carrying out the reaction in the presence of water and/or a low boiling point liquid e.g. a fluorinated alkane. Tertiary amines (many specified) may be used as additional catalysts. Surface active agents, flame retardants, plasticisers, fillers and antioxidants may also be incorporated in the compositions. Example 6 describes the preparation of polyurethane resins from adipic acid, glycerol, ethylene glycol and tolylene-2:4-diisocyanate in the presence of compounds of formulae: <FORM:0957841/C3/1> <FORM:0957841/C3/2> <FORM:0957841/C3/3> <FORM:0957841/C3/4> <FORM:0957841/C3/5> Example 7 describes the preparation of a cellular product from polypropylene glycol, a mixture of tolylene-2:4-diisocyanate and tolylene-2:6-diisocyanate, an aqueous solution of 4-dimethyl-aminopyridine and the compound of formula IV above. Specification 892,137 is referred to.ALSO:In Example 6, thin steel plates are coated with a polyurethane composition containing as catalysts organotin compounds as specified (see Division C3).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB12804/61A GB957841A (en) | 1961-04-10 | 1961-04-10 | The preparation of organo-tin compounds and their use as catalysts in the productionof polymethanes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB12804/61A GB957841A (en) | 1961-04-10 | 1961-04-10 | The preparation of organo-tin compounds and their use as catalysts in the productionof polymethanes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB957841A true GB957841A (en) | 1964-05-13 |
Family
ID=10011455
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12804/61A Expired GB957841A (en) | 1961-04-10 | 1961-04-10 | The preparation of organo-tin compounds and their use as catalysts in the productionof polymethanes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB957841A (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0569845A1 (en) * | 1992-05-11 | 1993-11-18 | Hoechst Aktiengesellschaft | Reaction products of dialkyl tin oxide and polyhydric phenols |
EP0688778A1 (en) * | 1994-06-20 | 1995-12-27 | General Electric Company | Trisstannoxanes |
US6369157B1 (en) | 2000-01-21 | 2002-04-09 | Cyclics Corporation | Blend material including macrocyclic polyester oligomers and processes for polymerizing the same |
US6420048B1 (en) | 2001-06-05 | 2002-07-16 | Cyclics Corporation | High molecular weight copolyesters from macrocyclic oligoesters and cyclic esters |
US6420047B2 (en) | 2000-01-21 | 2002-07-16 | Cyclics Corporation | Macrocyclic polyester oligomers and processes for polymerizing the same |
US6436548B1 (en) | 2000-09-12 | 2002-08-20 | Cyclics Corporation | Species modification in macrocyclic polyester oligomers, and compositions prepared thereby |
US6436549B1 (en) | 2001-07-16 | 2002-08-20 | Cyclics Corporation | Block copolymers from macrocyclic oligoesters and dihydroxyl-functionalized polymers |
US6525164B2 (en) | 2000-09-01 | 2003-02-25 | Cyclics Corporation | Methods for converting linear polyesters to macrocyclic oligoester compositions and macrocyclic oligoesters |
US6787632B2 (en) | 2001-10-09 | 2004-09-07 | Cyclics Corporation | Organo-titanate catalysts for preparing pure macrocyclic oligoesters |
US6831138B2 (en) | 2002-01-07 | 2004-12-14 | Cyclics Corporation | Polymer-containing organo-metal catalysts |
US7666517B2 (en) | 2001-06-27 | 2010-02-23 | Cyclics Corporation | Isolation, formulation, and shaping of macrocyclic oligoesters |
US7750109B2 (en) | 2000-09-01 | 2010-07-06 | Cyclics Corporation | Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer |
US7767781B2 (en) | 2000-09-01 | 2010-08-03 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
-
1961
- 1961-04-10 GB GB12804/61A patent/GB957841A/en not_active Expired
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5374754A (en) * | 1992-05-11 | 1994-12-20 | Hoechst Ag | Reaction products of dialkyltin oxide and polyhydric phenols |
EP0569845A1 (en) * | 1992-05-11 | 1993-11-18 | Hoechst Aktiengesellschaft | Reaction products of dialkyl tin oxide and polyhydric phenols |
EP0688778A1 (en) * | 1994-06-20 | 1995-12-27 | General Electric Company | Trisstannoxanes |
US6369157B1 (en) | 2000-01-21 | 2002-04-09 | Cyclics Corporation | Blend material including macrocyclic polyester oligomers and processes for polymerizing the same |
US6420047B2 (en) | 2000-01-21 | 2002-07-16 | Cyclics Corporation | Macrocyclic polyester oligomers and processes for polymerizing the same |
US6639009B2 (en) | 2000-01-21 | 2003-10-28 | Cyclis Corporation | Macrocyclic polyester oligomers and processes for polymerizing the same |
US7750109B2 (en) | 2000-09-01 | 2010-07-06 | Cyclics Corporation | Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer |
US8283437B2 (en) | 2000-09-01 | 2012-10-09 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
US6525164B2 (en) | 2000-09-01 | 2003-02-25 | Cyclics Corporation | Methods for converting linear polyesters to macrocyclic oligoester compositions and macrocyclic oligoesters |
US7767781B2 (en) | 2000-09-01 | 2010-08-03 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
US6436548B1 (en) | 2000-09-12 | 2002-08-20 | Cyclics Corporation | Species modification in macrocyclic polyester oligomers, and compositions prepared thereby |
US6713601B2 (en) | 2000-09-12 | 2004-03-30 | Cyclics Corporation | Species modification in macrocyclic polyester oligomers, and compositions prepared thereby |
US6420048B1 (en) | 2001-06-05 | 2002-07-16 | Cyclics Corporation | High molecular weight copolyesters from macrocyclic oligoesters and cyclic esters |
US7666517B2 (en) | 2001-06-27 | 2010-02-23 | Cyclics Corporation | Isolation, formulation, and shaping of macrocyclic oligoesters |
US6436549B1 (en) | 2001-07-16 | 2002-08-20 | Cyclics Corporation | Block copolymers from macrocyclic oligoesters and dihydroxyl-functionalized polymers |
US6787632B2 (en) | 2001-10-09 | 2004-09-07 | Cyclics Corporation | Organo-titanate catalysts for preparing pure macrocyclic oligoesters |
US6831138B2 (en) | 2002-01-07 | 2004-12-14 | Cyclics Corporation | Polymer-containing organo-metal catalysts |
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