GB2098229A - Stable polyurethane dispersions - Google Patents
Stable polyurethane dispersions Download PDFInfo
- Publication number
- GB2098229A GB2098229A GB8114139A GB8114139A GB2098229A GB 2098229 A GB2098229 A GB 2098229A GB 8114139 A GB8114139 A GB 8114139A GB 8114139 A GB8114139 A GB 8114139A GB 2098229 A GB2098229 A GB 2098229A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitrogen compound
- isocyanate
- polyether polyol
- molecule
- stoichiometric amount
- 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.)
- Withdrawn
Links
- 229920003009 polyurethane dispersion Polymers 0.000 title claims abstract description 12
- 239000012948 isocyanate Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 26
- 229910017464 nitrogen compound Inorganic materials 0.000 claims abstract description 22
- 150000002830 nitrogen compounds Chemical class 0.000 claims abstract description 22
- 229920005862 polyol Polymers 0.000 claims abstract description 19
- 150000003077 polyols Chemical class 0.000 claims abstract description 19
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 18
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 18
- 229920000570 polyether Polymers 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 229920002635 polyurethane Polymers 0.000 claims abstract description 10
- 239000004814 polyurethane Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000006185 dispersion Substances 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 4
- 229960004418 trolamine Drugs 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic isocyanates Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- VOUDXMXYROJCKN-UHFFFAOYSA-N 2,4-diisocyanato-1,3,5-triazine Chemical compound O=C=NC1=NC=NC(N=C=O)=N1 VOUDXMXYROJCKN-UHFFFAOYSA-N 0.000 description 1
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- GPDWNEFHGANACG-UHFFFAOYSA-L [dibutyl(2-ethylhexanoyloxy)stannyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)O[Sn](CCCC)(CCCC)OC(=O)C(CC)CCCC GPDWNEFHGANACG-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
-
- 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
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0871—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic
- C08G18/0876—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic the dispersing or dispersed phase being a polyol
-
- 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
- C08G18/3271—Hydroxyamines
- C08G18/3278—Hydroxyamines containing at least three 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
- C08G18/409—Dispersions of polymers of C08G in organic compounds having active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
A process for the production of a stable polyurethane dispersion in a liquid polyether polyol by mixing and reacting a nitrogen compound comprising hydroxyl groups in its molecule with a substantially stoichiometric amount or less than stoichiometric amount of an organic isocyanate while the nitrogen compound is dissolve or dispersed in the polyether polyol, the said nitrogen compound containing in its molecule three or more hydroxy-alkyl groups attached to the nitrogen atom or to nitrogen atoms, and polyurethanes produced by the said process. The nitrogen compound may be triethanolamine, tripropanolamine, a tetra(hydroxy alkyl) hydrazine, or tetra(2-hydroxypropyl) ethylene diamine.
Description
SPECIFICATION
Stable polyurethane dispersions
The invention relates to a process for the production of a stable polyurethane dispersion in a liquid polyether polyol by mixing and reacting a nitrogen compound comprising hydroxyl groups in its molecule with a substantially stoichiometric amount or less than stoichiometric amount of an organic isocyanate while the nitrogen compound is dissolved or dispersed in the polyether polyol.
Such a process is known from U.K. Patent
Specification 1,053,131 and uses a high molecular weight dihydric alcohol having substantially exclusively secondary hydroxyl groups as the dispersion medium and a dihydric primary alcohol as the compound to react with the isocyanate. The document teaches that the formation of the polyurethane dispersion as obtained by the process is based on a preferential reaction between the hydrogen atoms of the dihydric primary alcohol and the isocyanate groups without substantial reaction of the active hydrogen of the dispersion medium with the isocyanate, provided that no more than a stoichiometric amount of the isocyanate is employed.
This known process has the disadvantage of being limited in several respects, i.a. to the use of a dihydric alcohol having secondary hydroxyl groups, whilst many polyols conventionally used as starting materials for the production of polyurethanes are tri- or polyhydric, and in many cases have a considerable proportion of primary hydroxyl groups in the molecule.
It has now been found that the disadvantages indicated above are circumvented by using, as the compound to react preferentially with the isocyanate, a nitrogen compound which contains in its molecule three or more hydroxyalkyl groups attached to the nitrogen atom or to nitrogen atoms.
Accordingly, the invention provides a process for the production of a stable polyurethane dispersion in a liquid polyether polyol by mixing and reacting a nitrogen compound comprising hydroxyl groups in its molecule with a substantially stoichiometric amount or less than stoichiometric amount of an organic isocyanate while the nitrogen compound is dissolved or dispersed in the polyether polyol, characterized in that the nitrogen compound contains in its molecule three or more hydroxyalkyl groups attached to the nitrogen atom or to nitrogen atoms. In the preceding sentence and hereinafter the term "liquid" means that the polyether polyol is liquid at the reaction temperature.
It has been found that the polyurethane which results from the preferential reaction between the isocyanate and the nitrogen compound is produced in such a finely divided form in the polyether polyol that under normal conditions no sedimentation occurs even after prolonged standing. However, even if under certain extreme conditions sedimentation should occur, the stability of the dispersion can be easily restored by stirring.
Any suitable nitrogen compound satisfying the above-mentioned conditions may be used in the present process, and they comprise compounds having primary or secondary hydroxyl groups.
Preferred nitrogen compounds to be used in the present process are triethanolamine and tripropanolamine. Also preferred are diamines, such as a tetra(hydroxyalkyl)hydrazine and substituted alkylene diamines, for instance tetra(2-hydroxypropyl)ethylene diamine. It is within the scope of the invention to use mixtures of the nitrogen compounds as defined, e.g., a commercially available mixture of a major amount of triethanolamine and diethanolamine.
Any suitable organic isocyanate may be used in the process of the invention, including aliphatic and aromatic isocyanates, whilst di-isocyanates are preferred. Examples of suitable organic diisocyanates include the heterocyclic organic diisocyanates such as 1 ,6-hexamethylene diisocyanate, 1,4-butylene di-isocyanate, furfurylidene di-isocyanate and the preferred aromatic polyisocyanates such as 2,4-toluylene di-isocyanate, 2,6-toluylene di-isocyanate and mixtures thereof, preferably a mixture of about 80 per cent 2,4- and 20 per cent 2,6-toluylene diisocyanate, 4,4'-diphenylmethane di-isocyanate, 4,4'-diphenyl-3,3'-dimethyl methane diisocyanate, 1 ,5-naphthalene di-isocyanate, 1methyl-2,4-di-isocya nate-5-chlorobenzene, 2,4di-isocyanato-s-triazine, 1-methyl-2,4-di- isocyanato cyclohexane, p-phenylene diisocyanate and 1,4-naphthalene di-isocyanate.
As indicated above, substantially stoichiometric equivalents or less of isocyanato groups per equivalent of the reactive hydrogen atoms present in the nitrogen compound are used in the present process. In a preferred embodiment 1 0-60% of the stoichiometric amount of the isocyanate is used, whilst an isocyanate amount of 3050% of the stoichiometric amount is particularly preferred.
Suitable polyether polyols to be used in the present process are condensation products of one or more alkylene oxides with an initiator. The initiator may be difunctional, such as water, ethylene glycol, propylene glycol, and N (methyl)diethanolamine, trifunctional, such as glycerol, trimethylolpropane and tri-ethanolamine, or polyfunctional, such as pentaerythritol, sorbitol and sucrose. The hydroxyl groups of the polyether polyol may be exclusively secondary, such as the condensation products of propylene oxide. In some cases it is preferred to use a polyether polyol containing in its molecule substantially exclusively primary hydroxyl groups, such as condensation products of ethylene oxide or those obtained by oxyalkylation with propylene oxide followed by oxyalkylation with ethylene oxide.In other cases it is preferred to use a polyether polyol containing in its molecule both primary and secondary hydroxyl groups. In general the polyether polyols have a molecular weight between 500 and 10,000, preferably between 600 and 5000.
In many cases it is advantageous to use a catalyst for the preferential reaction between the nitrogen compound and the isocyanate. Suitable catalysts include tin compounds, such as stannous octoate, stannous stearate, dibutyltin dilaurate and dibutyltin 2-ethylhexanoate, and tertiary amines, such as triethylene diamine, Nmethylmorpholine and triethylamine.
In the process of the invention the reaction is usually carried out by first mixing the polyether polyol at, preferably, room temperature or, if required, at elevated temperatures, e.g. between 30 and 800C. After addition of the isocyanate the reaction mixture is stirred, preferably at a temperature between 20 and 250C, whilst the reaction takes place, yielding the desired stable polyurethane dispersion. The quantities of the starting materials to be used depend on the desired viscosity of the dispersion. Generally, the quantities and proportions of the starting materials are chosen so that the dispersion product has a solids content of between 5 and 40% by weight.
The invention includes stable polyurethane dispersions produced by the present process, which dispersions are useful for producing polyurethanes with attractive properties, e.g.
flexible foams having increased hardness and/or a high proportion of open cells. Because such dispersions are particularly suitable as starting materials for polyurethanes, in particular polyurethane foams, the invention also includes the production of polyurethanes by reacting the just-mentioned dispersions with isocyanate and polyurethanes so produced.
The invention is illustrated by the following
Example, in which parts are parts by weight.
EXAMPLE
100 parts of CARADOL 36-3 (CARADOL is a registered trade mark), a commercially available triol made by oxyalkylation based on glycerol, having a MW of approximately 4600 and hydroxyl groups which are preponderantly primary, and 3 parts of 85% pure triethanolamine were intimately mixed. After the addition of 0.2 ml of stannous octoate, 2.5 parts of CARADATE 80 (CARADATE is a registered trade mark), a 80/20 isomer mixture of 2,4- and 2,6-toluylene di-isocyanate, were added dropwise under vigorous stirring, whereby the temperature rose to 400C and polyurethane settled out. The reaction mixture was stirred for another 30 minutes to form a stable polyurethane dispersion having a viscosity at 25 C of 1 140 cP.
This dispersion was used in a well-known high resilience slabstock formulation to produce a polyurethane foam having the following properties:
density, kg/m3 30.7
hardness, kN/m2 2.48
tensile strength, kN/m2 105
elongation, % 1 60 tear strength, kN/m 0.25
resilience, % 61
Claims (12)
1. A process for the production of a stable polyurethane dispersion in a liquid polyether polyol by mixing and reacting a nitrogen compound comprising hydroxyl groups in its molecule with a substantially stoichiometric amount or less than stoichiometric amount of an organic isocyanate while the nitrogen compound is dissolved or dispersed in the polyether polyol, characterized in that the nitrogen compound contains in its molecule three or more hydroxyalkyl groups attached to the nitrogen atom or to nitrogen atoms.
2. A process as claimed in claim 1, in which the nitrogen compound is triethanolamine or tripropanolamine.
3. A process as claimed in claim 1, in which the nitrogen compound is a tetra(hydroxyalkyl)hydrazine.
4. A process as claimed in claim 1, in which the nitrogen compound is tetra(2hydroxypropyl)ethylene diamine.
5. A process as claimed in any one of claims 1-4, in which 1060% of the stoichiometric amount of the isocyanate is used.
6. A process as claimed in claim 5, in which 3050% of the stoichiometric amount of isocyanate is used.
7. A process as claimed in any one of claims 1-6, in which the polyether polyol contains in its molecule substantially exclusively primary hydroxyl groups.
8. A process as claimed in any one of claims 1-6, in which the polyether polyol contains in its molecule both primary and secondary hydroxyl groups.
9. A process for the production of stable polyurethane dispersions substantially as herein described with reference to the Example.
1 0. Stable polyurethane dispersions whenever produced by a process as claimed in any one of claims 1-9.
11. A process for the production of a polyurethane which comprises reacting a dispersion as claimed in claim 10 with isocyanate.
12. Polyurethanes produced by a process as claimed in claim 11.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8114139A GB2098229A (en) | 1981-05-08 | 1981-05-08 | Stable polyurethane dispersions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8114139A GB2098229A (en) | 1981-05-08 | 1981-05-08 | Stable polyurethane dispersions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2098229A true GB2098229A (en) | 1982-11-17 |
Family
ID=10521672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8114139A Withdrawn GB2098229A (en) | 1981-05-08 | 1981-05-08 | Stable polyurethane dispersions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2098229A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2139238A (en) * | 1983-05-05 | 1984-11-07 | Mobay Chemical Corp | Flexible polyurethane foams |
| GB2163762A (en) * | 1984-08-30 | 1986-03-05 | Hickory Springs Mfg Co | Polyurethane foams |
| GB2221217A (en) * | 1988-07-28 | 1990-01-31 | Mobay Corp | Process for the production of stable dispersions,the dispersions so produced, and the use thereof in the manufacture of polyurethanes |
| EP0441817A4 (en) * | 1988-11-01 | 1993-01-27 | Polylactane, Inc. | Improved polyols, use and method of preparation |
| WO2008116605A1 (en) * | 2007-03-24 | 2008-10-02 | Fritz Nauer Ag | Polyurethane foam |
| EP3133099A1 (en) | 2015-08-18 | 2017-02-22 | PCC Rokita SA | Polymer-modified polyol dispersion |
-
1981
- 1981-05-08 GB GB8114139A patent/GB2098229A/en not_active Withdrawn
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2139238A (en) * | 1983-05-05 | 1984-11-07 | Mobay Chemical Corp | Flexible polyurethane foams |
| GB2163762A (en) * | 1984-08-30 | 1986-03-05 | Hickory Springs Mfg Co | Polyurethane foams |
| US5506278A (en) * | 1984-08-30 | 1996-04-09 | Hickory Springs Manufacturing Company | Polyurethane foams |
| US5536757A (en) * | 1984-08-30 | 1996-07-16 | Hickory Springs Manufacturing Company | Polyurethane foams |
| US5569682A (en) * | 1984-08-30 | 1996-10-29 | Hickory Springs Manufacturing Company | Fire-retardant polyurethane foams and method of producing |
| GB2221217A (en) * | 1988-07-28 | 1990-01-31 | Mobay Corp | Process for the production of stable dispersions,the dispersions so produced, and the use thereof in the manufacture of polyurethanes |
| EP0441817A4 (en) * | 1988-11-01 | 1993-01-27 | Polylactane, Inc. | Improved polyols, use and method of preparation |
| WO2008116605A1 (en) * | 2007-03-24 | 2008-10-02 | Fritz Nauer Ag | Polyurethane foam |
| RU2462482C2 (en) * | 2007-03-24 | 2012-09-27 | Фритц Науэр Аг. | Foamed polyurethane |
| AU2008232006B2 (en) * | 2007-03-24 | 2013-09-12 | Fritz Nauer Ag | Polyurethane foam |
| EP3133099A1 (en) | 2015-08-18 | 2017-02-22 | PCC Rokita SA | Polymer-modified polyol dispersion |
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