GB997369A - Catalysed urethane polymers - Google Patents
Catalysed urethane polymersInfo
- Publication number
- GB997369A GB997369A GB2412361A GB2412361A GB997369A GB 997369 A GB997369 A GB 997369A GB 2412361 A GB2412361 A GB 2412361A GB 2412361 A GB2412361 A GB 2412361A GB 997369 A GB997369 A GB 997369A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diisocyanate
- lead
- glycol
- catalysts
- bismuth
- 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
- 229920000642 polymer Polymers 0.000 title abstract 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 4
- 125000005442 diisocyanate group Chemical group 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- 229910052797 bismuth Inorganic materials 0.000 abstract 3
- -1 ethylene, propylene Chemical group 0.000 abstract 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052753 mercury Inorganic materials 0.000 abstract 2
- 229920005862 polyol Polymers 0.000 abstract 2
- 150000003077 polyols Chemical class 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical class CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 1
- NUTVORGGYDQIDD-UHFFFAOYSA-N 1-ethylsulfanylethanol Chemical compound CCSC(C)O NUTVORGGYDQIDD-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- LVSQXDHWDCMMRJ-UHFFFAOYSA-N 4-hydroxybutan-2-one Chemical compound CC(=O)CCO LVSQXDHWDCMMRJ-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- DXCPEDGVEJWXRB-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC(C)=C(C)C=C1C Chemical compound N=C=O.N=C=O.CC1=CC(C)=C(C)C=C1C DXCPEDGVEJWXRB-UHFFFAOYSA-N 0.000 abstract 1
- 229910006653 SnII Inorganic materials 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- 235000019437 butane-1,3-diol Nutrition 0.000 abstract 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 229960002887 deanol Drugs 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- RVPVRDXYQKGNMQ-UHFFFAOYSA-N lead(2+) Chemical compound [Pb+2] RVPVRDXYQKGNMQ-UHFFFAOYSA-N 0.000 abstract 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000005474 octanoate group Chemical group 0.000 abstract 1
- 229940049964 oleate Drugs 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229920001281 polyalkylene Polymers 0.000 abstract 1
- 229920000728 polyester 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
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
- C10M129/95—Esters
-
- 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
- C07F5/04—Esters of boric acids
-
- 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
-
- 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
- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6484—Polysaccharides and derivatives thereof
-
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/395—Isocyanates
- D06M13/398—Isocyanates containing fluorine atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
A method for preparing an elastomer from the curable reaction mixture of an aromatic diisocyanate and an acid-free water-free organic polyol having end groups containing activating radicals selected from OH, S, O and N valence bonded to a carbon atom alpha or beta to a carbon atom carrying a primary or secondary isocyanate-reactive hydroxyl group comprises reacting the reagents in the presence of a catalytic amount of a soluble salt of an organic acid of a metal selected from PbII, HgII, SnII, BiIII and SbIII, the reaction being initiable at room temperature. The polyisocyanates may be moderately hindered diisocyanates, for example tolylene diisocyanate isomers, unhindered diisocyanates such as 4,41-biphenylene diisocyanate, or strongly sterically hindered diisocyanates such as 3,31-dimethoxy-4,41-biphenylene diisocyanate and durene diisocyanate. Suitable polyols are ethylene, propylene and 1,2-, 2,3- and 1,3-butylene glycols, polyalkylene ether glycols, polyesters and cellulose. A small amount of a triol or of a triisocyanate can be included in the reaction mixture to bring about cross-linking. Lead naphthenate, lead tallate, lead 2-ethyl-hexoate, bismuth naphthenate, antimony octoate, mercury naphthenate, stannous octoate and stannous oleate are specified catalysts. In a typical Example, (4) solid polymers are prepared at room temperature from mixtures of 3,31-dimethyldiphenylmethane - 4,41 - diisocyanate and polypropylene glycol (containing some trimethylol propane, the catalysts used being lead, tin and bismuth octoates, mercury and bismuth naphthenates (and, in comparison experiments, cobalt, magnesium and ferric octoates). In Example (1) a table is given which shows the rise in temperature which results on mixing a toluene diisocyanate/trimethylolpropane adduct with the monohydric alcohols C2H5OC2H4OH, C4H9OH and C2H5SC2H4OH, in the presence of the catalysts specified in Example (4). Graphs are given with Example (2), on which rise of temperature is plotted against time, results (using the same catalysts) on reacting a diisocyanate with 2,3-butylene glycol, 2,2-dimethylpropylene glycol, 4-hydroxy 2-butanone, a -hydroxy-acetophenone, glycol monoethyl ether, ethyl thioethanol, dimethylaminoethanol and ethylene glycol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4115360A | 1960-07-06 | 1960-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB997369A true GB997369A (en) | 1965-07-07 |
Family
ID=21915021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2412361A Expired GB997369A (en) | 1960-07-06 | 1961-07-04 | Catalysed urethane polymers |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1300693B (en) |
| GB (1) | GB997369A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419509A (en) * | 1965-11-22 | 1968-12-31 | Wyandotte Chemicals Corp | Mercury compounds as catalysts for the polyurethane reaction |
| US3670070A (en) * | 1968-12-17 | 1972-06-13 | Usm Corp | Processes for molding polyurethane foam articles |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008027914A1 (en) * | 2008-06-12 | 2009-12-17 | Henkel Ag & Co. Kgaa | Crosslinking 2K isocyanate compositions |
-
1961
- 1961-07-04 GB GB2412361A patent/GB997369A/en not_active Expired
- 1961-07-05 DE DE1961M0049577 patent/DE1300693B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419509A (en) * | 1965-11-22 | 1968-12-31 | Wyandotte Chemicals Corp | Mercury compounds as catalysts for the polyurethane reaction |
| US3670070A (en) * | 1968-12-17 | 1972-06-13 | Usm Corp | Processes for molding polyurethane foam articles |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1300693B (en) | 1969-08-07 |
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