GB1073209A - Improvements in or relating to polyureas - Google Patents
Improvements in or relating to polyureasInfo
- Publication number
- GB1073209A GB1073209A GB2447466A GB2447466A GB1073209A GB 1073209 A GB1073209 A GB 1073209A GB 2447466 A GB2447466 A GB 2447466A GB 2447466 A GB2447466 A GB 2447466A GB 1073209 A GB1073209 A GB 1073209A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- polyurea
- glass
- methyl isobutyl
- isobutyl ketone
- 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
- C08G18/28—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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
-
- 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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
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)
- Paints Or Removers (AREA)
Abstract
Ketimines are prepared by condensing methyl isobutyl ketone with (I) triethylene tetramine, (II) N,N-diaminopropyl stearylamine, (III) iminobispropylamine and (IV) methylimino-bispropylamine.ALSO:Polyureas or polyurea/polyurethane are prepared by adding moisture to an anhydrous composition comprising an aliphatic, cycloaliphatic or araliphatic polyisocyanate and a blocked polyamine which is an aldimine or ketimine of an aliphatic polyamine, the blocked polyamine having not more than one active hydrogen atom. Suitable polyisocyanates are polymethylene, alkylene, alkylidene, cycloalkylene and cycloalkylidene diisocyanates, triisocyanates and numerous araliphatic diisocyanates which may contain one or two aromatic rings and optionally, chlorine, methoxy, methyl and cyano radicals and substituents. Particularly suitable polyisocyanates are those derived from polymeric fat acids and having the formula [R]-[(CH2)yNCO]x where y is 0 or 1, x is 2 to 4 and R is the hydrocarbon group of a polymeric fat acid. Aromatic polyisocyanates may be mixed with the above less reactive polyisocyanates. The polyisocyanates may also be in the form of a polyurethate prepolymer which has been prepared by reacting a polyisocyanate with a polyol which may be monomeric or polymeric e.g. organic diols and triols and polyether and polyester polyols. The aldimines and ketimines are suitably prepared by reacting a carbonyl compound having a total of 2 to 6 carbon atoms with an aliphatic polyamine which preferably contains not more than 2 secondary amine groups, e.g. ethylene diamine, diethylene triamine, triethylene tetramine and the corresponding propylene and butylene diamines and N,N-diaminopropyl stearylamine. It is preferred to use a carbonyl compound which boils below or near the boiling point of water or which readily distils with water. The two components of the composition are simply mixed, if desired in the presence of a solvent, and to form a polyurea, moisture is added or the composition is exposed to atmospheric moisture.ALSO:Various substrates may be coated with a composition comprising an aliphatic, cycloaliphatic or araliphatic polyisocyanate and a blocked polyamine which is an aldimine or ketinine of an aliphatic polyamine, the blocked polyamine having not more than one active hydrogen atom, which composition may then be contacted with moisture to provide the substrate with a coating of a polyurea or polyurea / polyurethane. Examples describe the coating of (a) tin and glass with a diisocyanate prepared from dilinoleic acid of tall oil and aketimine prepared from triethylene tetramine and methylisobutyl ketone, (b) tin, steel, wood and glass with a diisocyanate as used in (a) above and a ketimine prepared from diethylene triamine and methyl isobutyl ketone (c) tin, glass and steel with a diisocyanate as used in (a) above and aketimine prepared from iminobispropylamine and methyl isobutyl ketone, (d) tin and glass with a mixture of p-phenylene-bis (ethyl-2-isocyanate) and aketimine from diethylene triamine and methyl isobutyl ketone dissolved in an organic acetate/xylene solvent and (e) glass, black plate steel and cold rolled steel with a mixture of a polyisocyanate prepolymer prepared from hexamethylene diisocyanate and water and a ketimine from ethylene diamine and methyl isobutyl ketone in an ethyl acetate solvent. The above compositions were cured at 50% relative humidity for a period of days to provide the substrates with tough polyurea coatings.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US46049065A | 1965-06-01 | 1965-06-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1073209A true GB1073209A (en) | 1967-06-21 |
Family
ID=23828914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2447466A Expired GB1073209A (en) | 1965-06-01 | 1966-06-01 | Improvements in or relating to polyureas |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE681917A (en) |
DE (1) | DE1595748A1 (en) |
GB (1) | GB1073209A (en) |
NL (1) | NL6607543A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2125247A1 (en) * | 1971-04-06 | 1972-10-19 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Stable mixtures of enamine compounds and polyisocyanates. Eliminated from: 2116882 |
US4469831A (en) * | 1981-08-26 | 1984-09-04 | Basf Aktiengesellschaft | Moisture-curing, storage stable, single-component polyurethane systems |
EP0149765A2 (en) * | 1984-01-11 | 1985-07-31 | American Cyanamid Company | Coating compositions containing a ketimine |
EP0985693A1 (en) * | 1998-03-25 | 2000-03-15 | The Yokohama Rubber Co., Ltd. | One-pack type moisture-curable composition |
CN108368232A (en) * | 2015-12-21 | 2018-08-03 | Sika技术股份公司 | Urethane composition with low plasticiser migration |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5104930A (en) * | 1990-02-27 | 1992-04-14 | Raychem Corporation | Polyurea gel compositions and articles therefrom |
NZ237054A (en) * | 1990-02-27 | 1993-03-26 | Raychem Corp | Crosslinked polyurea gels |
-
1966
- 1966-05-27 DE DE19661595748 patent/DE1595748A1/en active Pending
- 1966-06-01 GB GB2447466A patent/GB1073209A/en not_active Expired
- 1966-06-01 NL NL6607543A patent/NL6607543A/xx unknown
- 1966-06-01 BE BE681917D patent/BE681917A/xx unknown
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2125247A1 (en) * | 1971-04-06 | 1972-10-19 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Stable mixtures of enamine compounds and polyisocyanates. Eliminated from: 2116882 |
DE2125247B2 (en) * | 1971-04-06 | 1977-08-11 | Ausscheidung aus: 21 16 882 Schering AG, 1000 Berlin und 4619 Bergkamen | PROCESS FOR APPLYING VARNISHES, GROUTING COMPOUNDS, FILLING COMPOUNDS, COATING COMPOUNDS |
DE2125247C3 (en) * | 1971-04-06 | 1981-07-23 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Process for the application of paints, casting compounds, leveling compounds, coverings and coating compounds |
US4469831A (en) * | 1981-08-26 | 1984-09-04 | Basf Aktiengesellschaft | Moisture-curing, storage stable, single-component polyurethane systems |
EP0149765A2 (en) * | 1984-01-11 | 1985-07-31 | American Cyanamid Company | Coating compositions containing a ketimine |
EP0149765A3 (en) * | 1984-01-11 | 1985-08-21 | American Cyanamid Company | Coating compositions containing a ketimine |
EP0985693A1 (en) * | 1998-03-25 | 2000-03-15 | The Yokohama Rubber Co., Ltd. | One-pack type moisture-curable composition |
EP0985693A4 (en) * | 1998-03-25 | 2001-06-13 | Yokohama Rubber Co Ltd | One-pack type moisture-curable composition |
CN108368232A (en) * | 2015-12-21 | 2018-08-03 | Sika技术股份公司 | Urethane composition with low plasticiser migration |
CN108368232B (en) * | 2015-12-21 | 2021-07-30 | Sika技术股份公司 | Polyurethane compositions with low plasticizer migration |
Also Published As
Publication number | Publication date |
---|---|
NL6607543A (en) | 1966-12-02 |
DE1595748A1 (en) | 1970-05-14 |
BE681917A (en) | 1966-11-14 |
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