GB733624A - New synthetic resins derived from linear aliphatic polyethers and bifunctional isocyanates and rubber-like materials derived therefrom - Google Patents
New synthetic resins derived from linear aliphatic polyethers and bifunctional isocyanates and rubber-like materials derived therefromInfo
- Publication number
- GB733624A GB733624A GB9207/52A GB920752A GB733624A GB 733624 A GB733624 A GB 733624A GB 9207/52 A GB9207/52 A GB 9207/52A GB 920752 A GB920752 A GB 920752A GB 733624 A GB733624 A GB 733624A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isocyanate
- reaction
- rubber
- oxide
- polyether
- 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
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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7678—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing condensed aromatic rings
-
- 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
- C08G18/088—Removal of water or carbon dioxide from the reaction mixture or reaction components
- C08G18/0885—Removal of water or carbon dioxide from the reaction mixture or reaction components using additives, e.g. absorbing agents
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts 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
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
-
- 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
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- 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
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Synthetic resins are produced by reacting preferably at 120-160 DEG C., an aliphatic linear polyether with terminal hydroxyl groups and an average molecular weight greater than 1000 with an excess of a bifunctional isocyanate under substantially anhydrous conditions. Some of the suitable isocyanates mentioned are hexamethylene di-isocyanate 2-nitrodiphenylene-4 - 41 - di - isocyanate, 2 - nitrodiphenylmethane - 4,41 - di - isocyanate, naphthylene-1,4 - di - isocyanate, chrysene - 2,8 - di - isocyanate, tolylene, 4,41 - di - isocyanate, diphenylene - 4,41 - di - isocyanate and 4,41 - cyclohexyl di-isocyanate. Suitable polyethers are obtained by polymerization or copolymerization of ethylene oxide, isopropylene oxide, trimethylene oxide, a -methyltrimethylene oxide, 3,31-dimethyl trimethylene oxide, tetrahydrofurane, 1,3-dioxane or dioxolane. If the terminal groups are other than hydroxyl, e.g. chloro, they must be converted to hydroxyl, e.g. by heating with dilute alkali. The reaction mixture of di-isocyanate and polyether is made neutral or alkaline, e.g. by addition of a base such as triethylamine. the polyether is preferably dried, e.g. by heating in dry inert gas. If the molecular weight of the polyether is below 5000, the excess of di-isocyanate is relatively small to increase the chain length of the polymer. With polyethers of mol. weight above 5000, a large excess of di-isocyanate is used. The products have the general formula <FORM:0733624/IV (a)/1> in which R is the same or different aliphatic hydrocarbon radicals, the X's are divalent organic radical and a and b are integers, a being such that HO(R.O)oH has a mol. weight of at least 1000 and b such that the polymer has a mol. weight of at p least 2000. Rubber-like materials may be produced by heating these synthetic resins in presence of a basic catalyst, e.g. sodium methoxide or ethoxide; calcium or barium oxide or hydroxide; beryllium, lithium or sodium hydroxide; tri-methyl-, ethyl-, propyl-, butyl-, amyl- or benzyl-amine or dimethylaniline. The catalyst is mixed with the polyether before or after reaction with the di-isocyanate, by stirring or on a mill or Banbury mixer. Colouring materials may be added. Rubber-like materials may also be produced by modifying the resins with water, steam, ammonia or a compound with two groups capable of reacting with isocyanate groups. If the mixture is fluid reaction may be performed in a stirred mixer, otherwise on rolls or in a Banbury mixer. With water reaction may be at below 100 DEG , e.g. 80 DEG C., but preferred reaction temperatures are 120-160 DEG C. followed by mastication at 103-140 DEG C. Water may be added as a hydrated salt, e.g. sodium sulphate decahydrate. With diamines, dicarboxylic acids or amino acids cooling is necessary to permit mixing before reaction at higher temperature. Steam or ammonia as modifying agents may be blown on to the surface of the resin. Suitable bifunctional reagents are ethylene glycols; 1,3-propane diol; 1,4-butane diol; ethylene diamine; tri- or tetra-methylene diamine; m-phenylene diamine; naphthylene diamines; tolylene 2,4 - diamine; aminobenzylaniline; aminodiphenylamine; 2 - aminoethyl alcohol, 2 - amino - 1 - naphthol; m - aminophenol; glycollic acid; a - hydroxypropionic acid; amino acetic acid; and aminobenzoic acid. The products of the invention may also be converted to rubber-like products by reaction with polyhydroxy compounds, e.g. glycerol, pentaerythritol, trihydroxy tertiary butane, trimethylol propane, trimethylol ethane, 1,2,4-butane triol or Novolak resins of low molecular weight. The polyhydric compound may be mixed with the synthetic resin while it is still hot from its production or they may be mixed cold for conversion to the rubber-like state later. Conventional additives may be incorporated at any stage before conversion. The compositions ready for conversion to rubber-like state may be cast, moulded, or extruded as ribbon, film, fibres or filaments, or may be applied as coatings or impregnants. In examples tetrahydrofurane is polymerized, dried and reacted with various di-isocyanates. The products were (1) moulded after addition of water; (2) mixed to a crepe on a roll mill with tolylene diamine; (3) formed to a sheet by reaction with (a) triethylamine or (b) 1.4 butane diol; (4) moulded after admixture with sodium methoxide; (5) formed to a crepe on a roll mill with glycerol or 1,2,4-butane triol. Other examples are similar. In two of the examples the initial polyether was polytrimethylene oxide or poly-a -methyl trimethylene oxide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB318202X | 1952-04-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB733624A true GB733624A (en) | 1955-07-13 |
Family
ID=10328893
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9207/52A Expired GB733624A (en) | 1952-04-10 | 1952-04-10 | New synthetic resins derived from linear aliphatic polyethers and bifunctional isocyanates and rubber-like materials derived therefrom |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE519014A (en) |
CH (5) | CH341645A (en) |
DE (1) | DE1056821B (en) |
FR (1) | FR1074451A (en) |
GB (1) | GB733624A (en) |
Cited By (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2830038A (en) * | 1957-05-07 | 1958-04-08 | Du Pont | Poly (polyalkylene ether urethane) polymers containing terminal epoxide groups |
US2881065A (en) * | 1957-02-18 | 1959-04-07 | Mobay Chemical Corp | Polishing instrument |
US2888437A (en) * | 1956-11-20 | 1959-05-26 | Goodyear Tire & Rubber | Catalyst |
US2899411A (en) * | 1956-07-30 | 1959-08-11 | Polyurethane elastomers from hy- | |
US2917488A (en) * | 1959-12-15 | X x x x x | ||
US2953533A (en) * | 1958-04-04 | 1960-09-20 | Allied Chem | Highly cross-linked non flammable polyurethane foams and preparation of same |
US2956031A (en) * | 1958-04-04 | 1960-10-11 | Allied Chem | Highly cross-linked non-flammable polyurethane compositions and preparation of same |
US2961428A (en) * | 1955-10-24 | 1960-11-22 | Bayer Ag | Polyacetal-polyisocyanate polymers |
US2964422A (en) * | 1958-02-28 | 1960-12-13 | Johnson & Johnson | Pressure sensitive adhesive sheet and method of manufacture |
DE1104174B (en) * | 1955-08-04 | 1961-04-06 | Du Pont | Process for the production of an elastomer having urethane groups |
US2983693A (en) * | 1956-12-20 | 1961-05-09 | Du Pont | Isocyanate terminated polyurethane adhesive composition |
US3004840A (en) * | 1957-10-17 | 1961-10-17 | Dow Chemical Co | Solid composite propellants containing polyalkylene oxides |
US3004939A (en) * | 1958-08-19 | 1961-10-17 | Us Rubber Co | Method of making polyurethane rubber articles |
US3012987A (en) * | 1957-04-08 | 1961-12-12 | Du Pont | Coating composition comprising a blend of polyurethane reaction products |
US3033825A (en) * | 1959-03-26 | 1962-05-08 | Goodrich Co B F | Stable polyurethane rubbers |
US3036997A (en) * | 1956-11-21 | 1962-05-29 | Du Pont | Diene-modified polymers and elastomers thereform |
US3042631A (en) * | 1956-08-03 | 1962-07-03 | Simoniz Co | Polyurethane prepolymer and expanded product prepared therefrom |
US3049513A (en) * | 1959-03-26 | 1962-08-14 | Wyandotte Chemicals Corp | Ordered isocyanate-terminated polyether-based urethane compositions |
US3054778A (en) * | 1959-10-19 | 1962-09-18 | Dow Chemical Co | Acetic anhydride modified polyurethane |
US3074911A (en) * | 1957-12-05 | 1963-01-22 | Du Pont | Polyurethane resin coating composition containing carbamyl chloride stabilizer |
US3098658A (en) * | 1958-11-12 | 1963-07-23 | Goodrich Co B F | Golf ball having a polyetherurethane core |
US3105062A (en) * | 1958-08-18 | 1963-09-24 | Us Rubber Co | Method of making shaped polyurethane elastomer |
US3135711A (en) * | 1959-04-25 | 1964-06-02 | Bayer Ag | Polyurethane coating composition containing isocyanuric acid rings |
US3147974A (en) * | 1959-11-12 | 1964-09-08 | American Mach & Foundry | Synthetic bowling pins |
US3165566A (en) * | 1961-06-29 | 1965-01-12 | Goodrich Co B F | One step polyamine curing for polyurethane threads |
US3192187A (en) * | 1961-01-17 | 1965-06-29 | Air Prod & Chem | Preparation of stretchable polyurethane castings using a cocatalyst system of an epoxy alkane and a bicyclic amine |
US3201136A (en) * | 1960-07-06 | 1965-08-17 | Minnesota Mining & Mfg | Pipe joint of cast in place polyurethane |
US3216973A (en) * | 1961-11-16 | 1965-11-09 | Mobay Chemical Corp | Polyurethane plastics made with a triol bearing strictly secondary hydroxyl groups |
US3219634A (en) * | 1960-04-05 | 1965-11-23 | Dunlop Rubber Co | Polyurethanes based upon a polyepichlorohydrin polyol |
DE1219187B (en) * | 1965-02-24 | 1966-06-16 | Pittsburgh Plate Glass Co | Laminated safety glass |
US3267078A (en) * | 1963-12-16 | 1966-08-16 | Wyandotte Chemicals Corp | Polyether urethane coating composition cured with a di-imine |
US3287330A (en) * | 1958-02-06 | 1966-11-22 | Du Pont | Polyether polymers having unsaturated side chains |
US3359217A (en) * | 1961-07-21 | 1967-12-19 | Atlas Chem Ind | Rigid urethane foam compositions prepared utilizing an acid catalyzed sorbitol-propylene oxide condensation product |
DE1256892B (en) * | 1959-01-26 | 1967-12-21 | Wyandotte Chemicals Corp | Process for the production of polyadducts containing urethane and urea groups |
DE1273194B (en) * | 1959-01-26 | 1968-07-18 | Wyandotte Chemicals Corp | Process for the production of polyadducts containing urethane and urea groups |
US3475803A (en) * | 1965-08-27 | 1969-11-04 | Edward D Hill | Roller for applying paint,ink and the like |
US5145935A (en) * | 1988-09-30 | 1992-09-08 | Mitsubishi Jukogyo Kabushiki Kaisha | Shape memory polyurethane elastomer molded article |
US6559196B2 (en) | 2000-06-28 | 2003-05-06 | World Properties, Inc. | Tough, fire resistant polyurethane foam and method of manufacture thereof |
US6635688B2 (en) | 2000-06-28 | 2003-10-21 | World Properties, Inc. | Composite polyurethane foams and method of manufacture thereof |
US6653361B2 (en) | 2000-12-29 | 2003-11-25 | World Properties, Inc. | Flame retardant polyurethane composition and method of manufacture thereof |
US6780516B2 (en) | 2002-01-31 | 2004-08-24 | General Electric Company | Anti-fog coating composition, process, and article |
US6803495B2 (en) | 2000-06-28 | 2004-10-12 | World Properties, Inc. | Polyurethane foam composition and method of manufacture thereof |
US6872758B2 (en) | 2000-12-27 | 2005-03-29 | World Properties, Inc. | Polyurethane foams and method of manufacture thereof |
EP1546229A1 (en) * | 2002-08-09 | 2005-06-29 | E.I. Du Pont De Nemours And Company | Polyurethane and polyurethane-urea elastomers from polytrimethylene ether glycol |
US6915741B2 (en) | 2000-07-26 | 2005-07-12 | World Properties, Inc. | Method of printing including mounting plate on cylinder using foam cushion tape |
US7338983B2 (en) | 2004-02-10 | 2008-03-04 | World Properties, Inc. | Low density polyurethane foam, method of producing, and articles comprising the same |
EP1873178A3 (en) * | 2006-07-01 | 2008-05-21 | Bayer MaterialScience AG | Foamed and massive polyurethane elastomers on the basis of HMP polyisocyanates, method for its manufacture and use |
WO2010138724A1 (en) | 2009-05-27 | 2010-12-02 | Rogers Corporation | Polishing pad, polyurethane layer therefor, and method of polishing a silicon wafer |
WO2015187439A1 (en) | 2014-06-05 | 2015-12-10 | Rogers Corporation | Compressible thermally conductive articles |
WO2016127016A1 (en) | 2015-02-05 | 2016-08-11 | Rogers Corporation | Foam products and methods of producing the same |
WO2018048831A1 (en) | 2016-09-07 | 2018-03-15 | Rogers Corporation | Compressible thermally conductive articles |
WO2018075302A1 (en) | 2016-10-17 | 2018-04-26 | Rogers Corporation | Method for delaying curing in polyurethane and compositions and articles made therefrom |
WO2018093987A1 (en) | 2016-11-16 | 2018-05-24 | Rogers Corporation | Method for the manufacture of thermally conductive composite materials and articles comprising the same |
WO2019055607A1 (en) | 2017-09-14 | 2019-03-21 | Rogers Corporation | Methods of manufacture of a boron nitride foam |
CN111393467A (en) * | 2020-04-26 | 2020-07-10 | 扬州天启新材料股份有限公司 | Preparation method of organic silicon toughened isocyanate resin based on chemical bonding |
US20210292463A1 (en) * | 2020-03-18 | 2021-09-23 | Northwestern University | Dynamic polyurethane networks with post-recycling retention of cross-linking densities and mechanical properties |
CN113621121A (en) * | 2021-07-15 | 2021-11-09 | 中联重科股份有限公司 | Polyurethane composition, preparation method and application of polyurethane material |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2929802A (en) * | 1955-01-31 | 1960-03-22 | Du Pont | Elastic filaments of linear copolyurethanes |
US2929801A (en) * | 1955-01-31 | 1960-03-22 | Du Pont | Elastic amide/urethane/ether copolymers and process for making the same |
US2929804A (en) * | 1955-01-31 | 1960-03-22 | Du Pont | Elastic filaments of linear segmented polymers |
US2929803A (en) * | 1955-01-31 | 1960-03-22 | Du Pont | Elastic copolyureas from secondary diamines and process for making the same |
US2843568A (en) * | 1955-01-31 | 1958-07-15 | Du Pont | Polymeric polyether-polyurethanes |
DE1069379B (en) * | 1955-03-24 | 1959-11-19 | E. I. du Pont de Nemours and Company, Wilmington, 1DeI. (V. St. A.) | Process for the production of homogeneous plastics based on urethane groups and optionally also polyglycol ethers containing thioher groups |
US2948707A (en) * | 1955-09-14 | 1960-08-09 | Du Pont | Isocyanate-based polymers containing at least two different types of polymeric segments |
DE1059656B (en) * | 1955-11-21 | 1959-06-18 | Us Rubber Co | Production of open-cell foams |
DE1161007B (en) * | 1955-12-29 | 1964-01-09 | E. I. du Pont de Nemours & Company, Wilmington, Del. (V. St. A.) | Manufacture of synthetic resin films or threads |
US2901467A (en) * | 1956-04-20 | 1959-08-25 | Du Pont | Polyurethane coating compositions |
NL110107C (en) * | 1956-09-18 | |||
DE1029559B (en) * | 1956-11-16 | 1958-05-08 | Bayer Ag | Process for the production of high molecular weight crosslinked plastics with shaping |
US2980651A (en) * | 1957-04-29 | 1961-04-18 | Du Pont | Polyureylenes |
US3009901A (en) * | 1958-01-09 | 1961-11-21 | Du Pont | Reaction products of phenolic diamines with isocyanate terminated polyethers |
DE1160651B (en) * | 1960-04-14 | 1964-01-02 | Henschel Werke Ag | Callipers for determining the diameter and offset of workpieces, especially pipes and shafts |
US3234184A (en) * | 1961-06-29 | 1966-02-08 | Du Pont | Polyurethanes from ring-polyhalogenated diisocyanate |
DE4308791A1 (en) * | 1993-03-18 | 1994-09-22 | Bayer Ag | Process for the thermoplastic processing of polyurethanes |
-
0
- BE BE519014D patent/BE519014A/xx unknown
-
1952
- 1952-04-10 GB GB9207/52A patent/GB733624A/en not_active Expired
-
1953
- 1953-04-09 CH CH341645D patent/CH341645A/en unknown
- 1953-04-09 CH CH346024D patent/CH346024A/en unknown
- 1953-04-09 CH CH341310D patent/CH341310A/en unknown
- 1953-04-09 CH CH342750D patent/CH342750A/en unknown
- 1953-04-09 CH CH318202D patent/CH318202A/en unknown
- 1953-04-10 DE DEI13204A patent/DE1056821B/en active Pending
- 1953-04-10 FR FR1074451D patent/FR1074451A/en not_active Expired
Cited By (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2917488A (en) * | 1959-12-15 | X x x x x | ||
DE1104174B (en) * | 1955-08-04 | 1961-04-06 | Du Pont | Process for the production of an elastomer having urethane groups |
US2961428A (en) * | 1955-10-24 | 1960-11-22 | Bayer Ag | Polyacetal-polyisocyanate polymers |
US2899411A (en) * | 1956-07-30 | 1959-08-11 | Polyurethane elastomers from hy- | |
DE1112291B (en) * | 1956-07-30 | 1961-08-03 | Goodrich Co B F | Process for the production of rubber-like, thermoplastic polyurethanes |
US3042631A (en) * | 1956-08-03 | 1962-07-03 | Simoniz Co | Polyurethane prepolymer and expanded product prepared therefrom |
US2888437A (en) * | 1956-11-20 | 1959-05-26 | Goodyear Tire & Rubber | Catalyst |
US3036997A (en) * | 1956-11-21 | 1962-05-29 | Du Pont | Diene-modified polymers and elastomers thereform |
US2983693A (en) * | 1956-12-20 | 1961-05-09 | Du Pont | Isocyanate terminated polyurethane adhesive composition |
US2881065A (en) * | 1957-02-18 | 1959-04-07 | Mobay Chemical Corp | Polishing instrument |
US3012987A (en) * | 1957-04-08 | 1961-12-12 | Du Pont | Coating composition comprising a blend of polyurethane reaction products |
US2830038A (en) * | 1957-05-07 | 1958-04-08 | Du Pont | Poly (polyalkylene ether urethane) polymers containing terminal epoxide groups |
US3004840A (en) * | 1957-10-17 | 1961-10-17 | Dow Chemical Co | Solid composite propellants containing polyalkylene oxides |
US3074911A (en) * | 1957-12-05 | 1963-01-22 | Du Pont | Polyurethane resin coating composition containing carbamyl chloride stabilizer |
US3287330A (en) * | 1958-02-06 | 1966-11-22 | Du Pont | Polyether polymers having unsaturated side chains |
US2964422A (en) * | 1958-02-28 | 1960-12-13 | Johnson & Johnson | Pressure sensitive adhesive sheet and method of manufacture |
US2956031A (en) * | 1958-04-04 | 1960-10-11 | Allied Chem | Highly cross-linked non-flammable polyurethane compositions and preparation of same |
US2953533A (en) * | 1958-04-04 | 1960-09-20 | Allied Chem | Highly cross-linked non flammable polyurethane foams and preparation of same |
US3105062A (en) * | 1958-08-18 | 1963-09-24 | Us Rubber Co | Method of making shaped polyurethane elastomer |
US3004939A (en) * | 1958-08-19 | 1961-10-17 | Us Rubber Co | Method of making polyurethane rubber articles |
DE1122699B (en) * | 1958-08-19 | 1962-01-25 | Us Rubber Co | Process for the production of polyurethane elastomers |
US3098658A (en) * | 1958-11-12 | 1963-07-23 | Goodrich Co B F | Golf ball having a polyetherurethane core |
DE1256892B (en) * | 1959-01-26 | 1967-12-21 | Wyandotte Chemicals Corp | Process for the production of polyadducts containing urethane and urea groups |
DE1273194B (en) * | 1959-01-26 | 1968-07-18 | Wyandotte Chemicals Corp | Process for the production of polyadducts containing urethane and urea groups |
US3033825A (en) * | 1959-03-26 | 1962-05-08 | Goodrich Co B F | Stable polyurethane rubbers |
US3049513A (en) * | 1959-03-26 | 1962-08-14 | Wyandotte Chemicals Corp | Ordered isocyanate-terminated polyether-based urethane compositions |
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Also Published As
Publication number | Publication date |
---|---|
CH342750A (en) | 1959-11-30 |
BE519014A (en) | |
CH346024A (en) | 1960-04-30 |
CH318202A (en) | 1956-12-31 |
CH341645A (en) | 1959-10-15 |
FR1074451A (en) | 1954-10-06 |
CH341310A (en) | 1959-09-30 |
DE1056821B (en) | 1959-05-06 |
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