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
- 229920002396 Polyurea Polymers 0.000 title abstract 5
- 229920001228 polyisocyanate Polymers 0.000 abstract 9
- 239000005056 polyisocyanate Substances 0.000 abstract 9
- 239000000203 mixture Substances 0.000 abstract 8
- 229920000768 polyamine Polymers 0.000 abstract 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 abstract 6
- 125000001931 aliphatic group Chemical group 0.000 abstract 5
- 125000005442 diisocyanate group Chemical group 0.000 abstract 5
- 239000011521 glass Substances 0.000 abstract 5
- 150000004658 ketimines Chemical class 0.000 abstract 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 4
- 239000011135 tin Substances 0.000 abstract 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 abstract 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- DFTRQFUCZMJEGU-UHFFFAOYSA-N N,N-diaminohenicosan-1-amine Chemical compound NN(N)CCCCCCCCCCCCCCCCCCCCC DFTRQFUCZMJEGU-UHFFFAOYSA-N 0.000 abstract 3
- 229910000831 Steel Inorganic materials 0.000 abstract 3
- 150000004705 aldimines Chemical class 0.000 abstract 3
- 238000000576 coating method Methods 0.000 abstract 3
- -1 polymethylene Polymers 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 239000010959 steel Substances 0.000 abstract 3
- 239000000758 substrate Substances 0.000 abstract 3
- 229960001124 trientine Drugs 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 2
- 239000011248 coating agent Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229920000162 poly(ureaurethane) Polymers 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
- 229920002635 polyurethane Polymers 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000010960 cold rolled steel Substances 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- VJZWIFWPGRIJSN-XRHABHTOSA-N dilinoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O.CCCCC\C=C/C\C=C/CCCCCCCC(O)=O VJZWIFWPGRIJSN-XRHABHTOSA-N 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 abstract 1
- 229920005906 polyester polyol Polymers 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 150000003335 secondary amines Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000003784 tall oil Substances 0.000 abstract 1
- 150000004072 triols Chemical class 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- 239000008096 xylene Substances 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
- C08G18/28—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 |
| EP0149765A3 (en) * | 1984-01-11 | 1985-08-21 | American Cyanamid Company | Coating compositions containing a ketimine |
| 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 | Polyurethane composition with low plasticizer 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 BE BE681917D patent/BE681917A/xx unknown
- 1966-06-01 GB GB2447466A patent/GB1073209A/en not_active Expired
- 1966-06-01 NL NL6607543A patent/NL6607543A/xx unknown
Cited By (8)
| 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 |
| EP0149765A3 (en) * | 1984-01-11 | 1985-08-21 | American Cyanamid Company | Coating compositions containing a ketimine |
| 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 | Polyurethane composition with low plasticizer 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 |
|---|---|
| DE1595748A1 (en) | 1970-05-14 |
| BE681917A (en) | 1966-11-14 |
| NL6607543A (en) | 1966-12-02 |
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