SG187690A1 - Process for preparing aminotriazine alkoxylates - Google Patents
Process for preparing aminotriazine alkoxylates Download PDFInfo
- Publication number
- SG187690A1 SG187690A1 SG2013008164A SG2013008164A SG187690A1 SG 187690 A1 SG187690 A1 SG 187690A1 SG 2013008164 A SG2013008164 A SG 2013008164A SG 2013008164 A SG2013008164 A SG 2013008164A SG 187690 A1 SG187690 A1 SG 187690A1
- Authority
- SG
- Singapore
- Prior art keywords
- aminotriazine
- preparing
- alkoxylate
- oxide
- branched
- Prior art date
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- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 title claims abstract description 133
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 27
- -1 alkylene carbonate Chemical compound 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 60
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000011496 polyurethane foam Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 239000011149 active material Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000011527 polyurethane coating Substances 0.000 claims description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 2
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 claims description 2
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 claims description 2
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 description 52
- 239000000047 product Substances 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 239000000178 monomer Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000007858 starting material Substances 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 7
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960002887 deanol Drugs 0.000 description 6
- 239000012972 dimethylethanolamine Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- 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
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/263—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing heterocyclic amine groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Polyethers (AREA)
Abstract
16 Process for preparing aminotriazine alkoxylatesAbstract 5 The present invention relates to a process for preparing aminotriazine alkoxylates, whichcomprises at least one aminotriazine alkoxylate (a) being admixed with at least one aminotriazine (b) and reacted with at least one alkylene oxide (c), wherein the aminotriazine alkoxylate (a) is obtainable by reacting at least one am inotriazine (d) with at least one alkylene oxide (e) and/or at least one alkylene carbonate (g), and optionally at least one aminotriazine 10 alkoxylate (f).No suitable figure
Description
Process for Preparing aminotriazine alkoxylates
S The present invention relates to a process for Preparing amino-1,3,5-triazine polyetherols (hereinafter referred to as aminotriazine alkoxylates), more particularly 2,4,6-triamino-1 .3,5- triazine polyetherols {also known as melamine alkoxylates), and also to the amino-1,3,5-triazine polyetherols obtainable according to the present invention and their uses,
Prior art;
Preparing alkoxylated aminotriazines is known in principle. US 3812122 describes a process wherein aminotriazines are reacted with alkylene oxides in the presence of basic catalysts in
N,N-dialkylcarboxamides as solvents at 90 —- 200°C.
US 3328321 states that melamine alkoxylates are obtainable for example by reaction of melamine with ethylene carbonate or alkylene oxides in the presence of basic catalysts and solvents such as diethylene glycol dimethyl! ether, dimethylformamide and others.
US 3438986 describes a process for preparing aminotriazine alkoxylates by reacting aminotriazines with alkylene oxides in the presence of aryidiamines as solvents,
GB 1064148 states that the reaction of aminofriazines with alkylene oxides under basic conditions can also be carried out in the presence of aromatic, saturated or unsaturated polyols,
However, the use of melamine requires the additional presence of an inert solvent such as dimethy! sulfoxide.
DE 3412082A1 describes the reaction of aminotriazines with aikylene oxides without the
Presence of a catalyst and without the use of an inert solvent. However, this process utilizes at least one 2- ta 6-hydric aliphatic and/or cycloaliphatic alcohol as co-starter.
The processes described in the documents listed above have serious disadvantages. They require either a) the presence of a polar and hence generally also high-boiling, inert solvent (dimethyiformamide or dimethyl sulfoxide) which, after the reaction, has to be expensively and inconveniently removed again from the product, and/or b) the presence of at least one hydroxyl- or amino-modified co-starter, leading to a mixture of an aminotriazine alkoxylate and the co-starter alkoxylate in the product. Thus, the aminotriazine alkoxylate contains the co-starter alkoxylate as an impurity. Since the removal of the high-boiling polar solvents is associated with appreciable technical inconvenience and the presence of a co-starter alkoxylate has an adverse 40 effect on product properties, products of this kind have hitherto failed to become established in the market.
It is an object of the present invention to develop an alternative process for preparing aminotriazine alkoxylates which a) can proceed without the use of inert solvents and b) provides aminotriazine alkoxylates that do not contain any other polyetherols as impurities,
We have found that this object is surprisingly achieved by the combinations of features in the claims.
The present invention accordingly provides a process for preparing aminotriazine alkoxylates, which comprises at least one aminotriazine alkoxylate (a) being admixed with at least one aminotriazine (b) and reacted with at least one alkylene oxide (c), wherein the aminotriazine alkoxylate (a) is obtainable by reacting at least one aminotriazine (d) with at least one alkylene oxide (e) and/or at least one alkylene carbonate {g), and optionally at least one aminotriazine alkoxylate (f).
The present invention further provides aminotriazine alkoxylates obtainable by the process of the present invention and also the use of aminotriazine alkoxylates obtainable by the process of the present invention for surface-active materials, more particularly surfactants and emulsifiers, dispersants for aqueous systems, for organic solvents or for polyether polyols, solubilizers for water-insoluble compounds (agro or pharma adjuvants), polyetheral component in polyurethane system formulations, preferably in rigid polyurethane foam or polyurethane coating formulations, more preferably in rigid polyurethane foam systems.
In a preferred embodiment of the present invention process for preparing aminotriazine alkoxylates, the aminotriazine alkoxylate (a) is selected from the group comprising reaction products of at least one compound of the following formula:
NR'R" 1)
EN. where R’ and R" are each selected from H, branched or linear C1-C22 compounds, polypropylene glycol and polyethylene glycol, R™ and R™ are each selected from H, NR'R”,
OH, halide, branched or linear G1-C22 chains, C6R5, where R is selected from H, branched or linear C1-C22 alkyl chains, aryl, or a mixture of compounds having this formula, with at least one alkylene oxide (h).
The aminotriazine alkoxylate (a) of the first reaction batch is obtainable by any one of the methods described above in the cited patent documents.
In addition, the aminotriazine alkoxylate (a) of the first reaction batch is obtainable by the following process steps: 1.) reacting an aminotriazine with aqueous KOH or NaOH solution with subsequent removal of water by vacuum stripping, 2.) reacting the resulting metal salt of the aminotriazine with aikylene oxides, 3.) neutralizing the reaction product (preferably with © Brdnstedt acids such as phosphoric acid, hydrochloric acid, sulfuric acid, but also CO, or
Makrosorb® (for example Makrosorb® MP5, a magnesium silicate from INFOS Silicas, specifically developed for purifying polyols), 4.} removing the neutralization salts from step 3 and unconverted aminofriazine of step 2 from the aminotriazine alkoxylate by filtration. The aminotriazine alkoxylate thus neutralized can be used as starting material {a) in the process described above.
The aminotriazine alkoxylate (a) is obtainable in the presence or absence of a catalyst.
In one embodiment of the process of the present invention, the aminotriazine alkoxylate (a), the starting material of the process of the present invention, is obtained in the presence of a solvent. In this case, itis preferable for residuals of the solvent to be removed, in a conventional manner, before using the aminotriazine alkoxylate (a) in the present invention process for preparing aminotriazine alkoxylates.
In a further embodiment of the process of the present invention, the aminotriazine alkoxylate (a) is obtained in the absence of a solvent.
A person having ordinary skill in the art will know that similar processes are also referred to as “heel processes”, which are characterized in that a reaction batch includes a portion of the reaction product from the previous reaction batch (the “heel") together with the starting component, in this case the aminotriazine. This process step improves the solubility of the starter, since the reaction product acts as solubilizer, causing the reaction to proceed more completely and not to leave any unconverted aminotriazine behind in the reaction product.
Unconverted aminotriazine in the reaction product is a disadvantage because it is present in the reaction product in solid form and phase separates with the liquid reaction product.
In many cases, moreover, no catalyst need be added in the process of the present invention since the amino functionalities of the aminotriazines act autocatalytically for the addition step of the alkylene oxides.
The process of the present invention thus offers an economic advantage, inter alia because no catalyst is required in many cases; in addition, the products can be used in pure form and without additional purification requirements (high in conventional processes because of high- boiling solvents or contamination due ta co-starter) directly in the particular application. In 40 contrast to the existing heel processes, moreover, the addition of an alkoxylation catalyst can be dispensed with in this case,
However, since autocatalytic conversion is generally restricted with regard to the molecular weight to be achieved, further reaction of the reaction product from the process described, with alkylene oxide, is alsp possible in the presence of basic catalysts such as alkali metal hydroxides, alkali metal alkoxides or amines, such as dimethylethanolamine or imidazole,
Aminotriazines useful as aminotriazines (b) and (d} include all aminotriazines comprising at least one and preferably at least two amino groups attached in the molecule. These are for example aminotriazines substituted with aliphatic, cycloaliphatic or aromatic radicals having 1 to 18 carbon atoms, such as: 6-methyl-, B-ethyl-, 8-n-propyl-, B-isopropyl-, 6-butyl-, 6-hexyl-, 6-nonyl-, 6-stearyl-, 6-butenyl-, 6-cyclohexyl-, 6-phenyl-, 6-dimethylamino-2,4-diamino-1,3 5. triazine. It is further possible to use aminotriazines having hydroxyl substituents, for example 6-hydroxy-2,4-diamino-1,3 5-triazine (ammeline). Preference is given to using sparingly soluble high-melting aminotriazines such as, for example, 8-methyl-2,4-diamino-1,3,5-triazine, 6-phenyl-2,4-diamino-1,3,5-triazine and, in particular, melamine. The aminotriazines can be 16 used singly or in the form of mixtures,
Aminotriazines (b) and {d) may each also be independently selected from compounds of the following formula:
N R'R FH
I >
M PR sr ow”
R N R where R’ and R” are each selected from H, branched or linear C1-C22 compounds, polypropylene glycol and polyethylene glycol, R™ and R™ are each selected from H, NR'R",
OH, halide, branched or linear C1-C22 chains, C6R5, where R is selected from H, branched or linear C1-C22 alkyl chains, aryl, or 3 mixture of Compounds having this formula,
Here the aminotriazines {b) and (d) can be the same or different.
Preference is given to 2,4,6-triamino-1 .3,5-triazine (also known as melamine) for use as aminotriazine (b) and/or (d).
In a preferred embodiment of the present invention process for preparing aminotriazine alkoxylates, the aminotriazine alkoxylate (f) is selected from the group comprising reaction products of at least one compound of the folowing formula:
NR'R" 0)
AN 2 "n
R' where R' and R” are each selected from H, branched or linear C1-C22 compounds, polypropylene glycol and polyethylene glycol, R™ and R"™ are each selected from H, NR'R”, 5 OH, halide, branched or linear C1-C22 chains, CBRS, where R is selected from H, branched or linear C1-C22 alkyl chains, aryl, or a mixture of compounds having this formula, with at least one alkylene oxide (i).
In one embodiment of the process of the present invention, the aminotriazine alkoxylate (f) is present.
In another embodiment of the process of the present invention, the aminotriazine alkoxylate (f) is not present.
The alkylene oxides (c). (e}, (h) and (i) are preferably each independently selected from the group comprising propylene oxide, ethylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, isobutylene oxide, 1,2-pentene oxide, styrene oxide, epichlorohydrin, glycidol and mixtures thereof. Simitarly, 2,3-pentene oxide, 1,2-hexene oxide, cyclohexene oxide, glycidyl ether and/or butadiene monoxide or mixtures thereof can be used, Particular preference in each case is given to propylene oxide and ethylene oxide.
The alkylene carbonate (9) is preferably selected from the group comprising propylene carbonate, ethylene carbonate, glycerol carbonate and mixtures thereof.
The reaction of the aminotriazines with alkylene oxide in the presence of aminotriazine alkoxylates is preferably carried out at temperatures between 100 and 200°C and more preferably between 150 and 180°C, generally at pressures of 1 —- 10 bar.
In a preferred embodiment of the process of the present invention, the reaction of aminotriazine alkoxylate (a) with at least one aminotriazine (b) and with at least one alkylene oxide (c) is carried out at temperatures between 100 and 200°C and at pressures of 1 — 10 bar in the absence of a catalyst and in the absence of a solvent.
The mass ratio between aminotriazine alkoxylate (a), initially charged to the reactor together with aminotriazine, and the aminotriazine (b) is in the range from 20%:80% to 95%:5% and preferably in the range from 40%:60% to 95%:5%.
The reaction of the aminotriazines with alkylene oxide in the presence of aminoftriazine alkoxylates can take place in the presence of basic catalysts. Useful catalysts include for example alkali and alkaline earth metal hydroxides and alkoxides. In addition, amines can be used as catalysts. The use of amines has the technical advantage, particularly with a view to polyurethane applications, that the catalyst does not have to ba removed from the end product and accordingly no additional neutralization and filtration step is needed. Itis preferable to use 5S tertiary amines. Examples of aminic catalysts are trimethylamine (TMA), tributytamine, triethylamine (TEA), dimethylethanolamine (DMEOA) and dimethyleyclohexylamine (DMCHA), imidazole and substituted imidazole derivatives, preferably dimethylethanolamine.
Particular preference is given to DMEOA (dimethylethanolamine), imidazole,
Carbenes, preferably N-heterocyclic carbenes, can also be used as catalysts.
In a further preferred embodiment, the aminotriazines are reacted with atkylene oxide without the presence of a catalyst. Since the aminotriazines themselves bear catalytically effective functional groups, the reaction can accordingly take place autocatalytically. In this case too there is the technical advantage that there is no need for neutralization and filtration.
After the reaction has ended, the reaction product is generally freed of residual monomer and other volatile components by vacuum stripping. Stripping can be effected for example by means of aninert gas {nitrogen for example) or else with water vapor. When metal hydroxides or metal alkoxides were used as catalysts in the reaction with alkylene oxides, these are for example neutralized by addition of Bronsted acids and the metal saits separated from the reaction product by filtration.
The alkylene oxides can add blockwise or randomly. Both straight and mixed alkylene oxides can be used.
The reaction of the aminotriazine alkoxylate (a) with at least one aminotriazine (b) and with at least one alkylene oxide (c) to prepare aminotriazine alkoxytates is preferably carried out in the invention without use of an inert solvent.
However, preparing the aminotriazine alkoxylate (a) may, as mentioned, optionally be carried out in the presence of an inert solvent,
According to the present invention, the process for preparing aminotriazine alkoxylates by reacting at least one aminotriazine alkoxylate (a) with at least one aminotiiazine (b) and with at least one alkylene oxide (c) preferably does not use any co-starters, for example reactive salvents having hydroxyl or amino groups, 40 Preparing the aminotriazine alkoxylate (a), however, can optionally be carried out in the presence of a hydroxyl and/or amino-functional and hence reactive co-starter,
The process can be carried out discontinuously as a batch process or else ag a semibatch process. The process can also be carried out continuously by continuously feeding the aminotriazine or a mixture of the aminotriazine alkoxylate with the aminotriazine to the reaction tank and continuously removing the product,
The aminotriazine alkoxylates obtainable using the process described generally have a hydroxyl number of 10 —- 600 mg KOH/g, preferably between 50 — 500 mg KOH/g. The functionalities of the aminotriazines of the present invention are generally between 2-8 ang preferably between 3-6. The molecular weights are generally between 300 and 15 000 g/mol and preferably between 400 and 5000 g/mol,
The aminotriazine alkoxylates obtained according to the present invention are useful for a wide variety of purposes, for example for: 1) formaldehyde-free leather tanning agents and/or leather refanning agents 2.) surface-active materials {surfactants, emulsifiers) 3.) dispersants for aqueous systems, for organic solvents or for polyehter polyols 4.) solubilizers for water-insoluble compounds (agro or pharma adjuvants) 5.) polyetherql component in polyurethane system formulations, preferably in rigid palyurethane foam and polyurethane coating formulations, more preferably in rigid palyurethane foam systems. (n addition, the aminotriazine alkoxylates obtainable by the process of the present invention can be used as an initial charge in a process for preparing further aminotriazine alkoxylates, More particularly, the aminotriazine alkoxylates obtainable by the process of the present invention can also be used as an initial charge in a process for preparing further aminotriazine alkoxylates which is analogous to the pracess of the present invention. In this case, the aminotriazine alkoxylates obtainable according to the present invention serve in turn as aminotriazine alkoxylate (a) according to claim 1.
The aminotriazine alkoxylates obtainable according to the present invention are as mentioned very useful for forming surface-active agents of the active type. They are accordingly very useful for moistening or softening wool, cotton or cellulose acetate, cellulose nitrate, viscose and similar materials. They are also useful for emulsifying mineral oils, glycerides, fats, oils and the 33 like. The aminotriazine alkoxylates obtainable accarding to the present invention find application in the formulation of printing inks, dye pastes, dry cleaning baths, leather finishes and flotation agents. By using the aminotriazine alkoxylates obtainable according to the present invention jt is possible to ensure bulk, dissolution resistance and enhanced wet strength in the case of rayon and other fibers. The aminotriazine alkoxylates obtainable according to the present invention 40 also reduce the creasing and wrinkling tendency of treated textile materials,
The examples which follow illustrate the invention.
Example 1: Preparation of an aminotriazine ethoxylate (a1) 48.2 g of melamine were admixed with 1.44 g of aqueous KOH solution (30% strength) in a 300 mL steel autoclave and the reaction mixture was nitrogen inertized three times. Then, the reaction mixture was freed from water by evacuation at 110°C to 10 mbar. This was followed by the metered addition of 183.8 g of ethylene oxide in the course of 4 hours, After the ethylene oxide kicko#f amount had been reached, a postreaction took place until the pressure became constant. After the reaction, the residual monomer was distilled off at 110°C for 30 min at 10 mbar and the crude product was discharged at room temperature. The crude product additionally contained unconverted melamine in solid form, which was initially separated from the liquid melamine ethoxylate by filtration. The basic filtrate was then admixed with 5% of water and 3% of Makrosorb®, heated at 90°C for 60 min, freed at 3 mbar and 120°C from water and other volatile components and finally pressure filtered. The neutralized melamine ethoxylate had a hydroxyl number of 174.0 mg KOH/g and a residual alkalinity of < 10 ppm K+ (determined by atomic absorption Spectrometry, AAS) and was used directly as aminotriazine alkoxylate (a1) for the process of the present invention in accordance with the experimental procedures described hereinbelow,
Example 2: Preparation of a melamine ethoxylate using the product of Example 1 as initia! charge 63 gof the melamine ethoxylate (a1) from Example 1 were initially charged to a 300 mL autoclave together with 7 g of mefamine and the mixture was nitrogen inertized three times.
Then, the reaction batch was heated to 110°C and 104 g of ethylene oxide were metered in over 7.5 hours. On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 170 g of a homogeneous fiquid having a hydroxyl number of 142 mg KOH/q.
Example 3: Preparation of a melamine ethoxylate using the product of Example 2 as initial charge 63 g of the melamine ethoxylate from Example 2 were initially charged to a 300 mL autoclave together with 7 g of melamine and the mixture was nitrogen inertized three times. Then, the reaction batch was heated to 160°C and 104 g of ethylene oxide were metered in over 4 hours.
On completion of the metered addition, a reaction took place for 3 hours. After the reaction had 40 ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 170 g of a homogeneous liquid having a hydroxyl number of 147 mg KOH/g.
Example 4; Preparation of a melamine ethoxylate using the product of Example 3 ag initial charge 40 g of the melamine ethoxylate from Example 3 were initially charged to a 300 mL autoclave together with 10 g of melamine and the mixture was nitrogen inertized three times, Then, the reaction batch was heated to 160°C and 171.6 g of ethylene oxide were metered in over 4 hours. On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 210 g of a homogeneous liquid having a hydroxyl number of 154.6 mg KOH/g.
Example 5: Preparation of a melamine ethoxylate using the product of Exampie 4 as initial charge 28 g of the melamine ethoxylate from Example 4 were initially charged to a 300 mL autociave together with 12 g of melamine and the mixture was nitrogen inertized three times. Then, the reaction batch was heated to 180°C and 196 g of ethylene oxide were metered in over 7.5 hours. On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 230gofa homogeneous liquid having a hydroxyl number of 161.3 mg KOH/qg.
Example 8: Preparation of a melamine ethoxylate using the product of Example 5 as initial charge 20.3 g of the melamine ethoxylate from Example 5 were initially charged to a 300 mi autoclave together with 13.5 g of melamine and the mixture was nitrogen inertized three times. Then, the reaction batch was heated to 160°C and 206.2 g of ethylene oxide were metered in over 10 hours. On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 230 gofa homogeneous liquid having a hydroxyl number of 171.2 mg KOH/g.
Example 7: Preparation of a melamine ethoxylate using the product of Example 6 as initial charge 14.6 g of the melamine ethoxylate from Example 6 were initially charged to a 300 mL autoclave 40 together with 14.5 g of melamine and the mixture was niirogen inertized three times. Then, the reaction batch was heated to 160°C and 200 g of ethylene oxide were metered in over 12 hours, On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 228 g of a homogeneous liquid having a hydroxyl number of 162.5 mg KOH/g.
Example 8; Preparation of a melamine ethoxylate using the product of Example 7 as initial charge 14.6 g of the melamine ethoxylate from Example 7 were initially charged io a 300 mL autoclave together with 14.5 g of melamine and the mixture was nitrogen inertized three times. Then, the reaction batch was heated to 160°C and 209 g of ethylene oxide were metered in over 7.5 hours. On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 228 g of a homogeneous liquid having a hydroxyl number of 162.5 mg KOH/g.
Example 9; Preparation of an aminotriazine Propoxylate (a2) 20.0 g of melamine were admixed with 2.4 g of aqueous KOH solution (50% strength) in a 300 mL steel autoclave and the reaction mixture was nitrogen inertized three times. Then, the reaction mixture was freed from water by evacuation at 110°C to 10 mbar. This was followed by the metered addition of 220.0 g of propylene oxide in the Course of 20 hours, After the propylene oxide kickoff amount had been reached, a postreaction took place until the pressure became constant, After the reaction, the residual monomer was distilled off at 110°C for 30 min at 10 mbar and the crude product was discharged at room temperature. The crude product additionally contained unconverted melamine in solid form, which was initially separated from the liquid melamine Propoxylate by filration. The basic fiitrate was then admixed with 5% of water and 3% of Makrosorb®, heated at 80°C for 60 min, freed at 3 mbar and 120°C from water and other volatile components and finally pressure filtered. The neutralized melamine propoxylate had a hydroxyl number of 238.4 mg KOH/g and a residual alkalinity of < 10 ppm K+ (determined by atomic absorption spectrometry, AAS) and was used directly as starting material for the subsequent batches described hereinbelow.
Example 10; Preparation of a melamine propoxylate using the product of Example 9 as initia] charge 106.1 gofthe melamine propoxylate (a2) from Example 9 were initially charged to a 300 mL autoclave together with 11.8 g of melamine and the mixture was nitrogen inertized three times.
Then, the reaction batch was heated to 160°C and 122.2 g of propylene oxide were metered in over 9 hours. On completion of the metered addition, a reaction took place for 10 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was 40 discharged at room temperature to obtain 230 g of a homogeneous liquid having a hydroxyl number of 273 mg KOH/g.
Example 11; Preparation of a melamine propoxylate using the product of Example 10 as initial charge 63.2 g of the melamine propoxylate from Example 10 were initially charged to a 300 mL 95 autoclave together with 15.8 g of melamine and the mixture was nitrogen inertized three times.
Then, the reaction batch was heated to 160°C and 161 g of propylene oxide were metered in over 12 hours. On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 230 g of a homogeneous liquid having a hydroxy! number of 267 mg KOH/g.
Example 12: Preparation of a melamine propoxylate using the product of Example 11 as initial charge 63.2gofthe melamine propoxylate from Example 10 were initially charged to a 300 mL autoclave together with 15.8 g of melamine and the mixture was nitrogen inertized three times.
Then, the reaction batch was heated to 160°C and 161 g of propylene oxide were metered in over 11 hours. On completion of the metered addition, a reaction took place for 3 hours, After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 230 g of a homogeneous liquid having a hydroxyl number of 270 mg KOH/g.
Example 13: Preparation of a melamine propoxylate using the product of Example 12 as initiai charge 63.2 g of the melamine propoxylate from Example 12 were initially charged to a 300 mL autoclave together with 15.8 g of melamine and the mixture was nitrogen inertized three times.
Then, the reaction batch was heated to 160°C and 140 g of propylene oxide were metered in over 8 hours. On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 210 g of a homogeneous liquid having a hydroxyl number of 285 mg KOH/g.
Example 14: Preparation of a melamine propoxylate using as initial charge a melamine ethoxylate prepared by reaction of melamine with ethylene carbonate 35.2 g of a melamine ethoxylate (a3) having a hydroxyl number of 515.8 mg KOH/g, prepared by reaction of melamine with ethylene carbonate similarly to U.S. Pat. No. 3,328,321, were 40 initially charged to a 300 mL autoclave together with 3.5 g of melamine and the mixture was nitrogen inertized three times. Then, the reaction batch was heated to 100°C and 100 g of propylene oxide were metered in over 2 hours. On completion of the metered addition, a reaction took place for 3 hours. After the reaction had ended, residual monomer was removed in vacuo and the product was discharged at room temperature to obtain 128g of a homogeneous liquid having a hydroxy! number of 195 mg KOH/g.
The experimental results accordingly show that the process of the present invention provides homogeneous aminotriazine alkoxylates without use of non-aminotriazine-containing co-siarters and without use of an inert solvent, Accordingly, the products are pure aminotriazine alkoxylates, which are obtainable via a simple and economical process.
Claims (16)
- We claim:- 1) A process for preparing aminotriazine alkoxylates, which comprises at least one aminotriazine aikoxylate (a) being admixed with at least one aminotriazine (b) and reacted with at least one alkylene oxide (c), wherein the aminotriazine alkoxylate (a) is obtainable by reacting at least one aminotriazine (4) with at least one alkylene oxide (e) and/or at least one alkylene carbonate (g), and optionally at least one aminotriazine alkoxylate (f).
- 2) The process for preparing aminotriazine alkoxylates according to claim 1 wherein the aminotriazine atkoxylate (a) is selected from the group comprising reaction products of at least one compound of the following formula: NR'R" lO)NP . v v where R’ and R" are each selected from H, branched or linear C1-C22 compounds, polypropylene glycol and polyethylene glycol, R” and R"™ are each selected from H, NR'R", OH, halide, branched or linear C1-C22 chains, C6R5, where Ris selected from H, branched or linear C1-C22 alkyl chains, aryl, or a mixture of compounds having this formula, with at least one alkylene oxide (h).
- 3) The process for preparing aminotriazine alkoxylates according to claim 1 or 2 wherein the aminotriazine (b) and the aminotriazine (d) are each independently selected from compounds of the following formula: N R’ R" 1) A A Tre R N R where R’ and R” are each selected from H, branched or linear C1-C22 compounds, polypropylene glycol and polyethylene glycol, R™ and R™ are each selected from H, NR'R", OH, halide, branched or linear C1-C22 chains, C6RS, where R is selected from H, branched or linear C1-C22 alkyl chains, aryl, or a mixture of compounds having this formula,
- 4) The process for preparing aminotriazine alkoxylates according to any preceding claim wherein the aminotriazine (b) and/or the aminotriazine (d) is 2,4,6-triamino-1 ,3,5-triazine.
- 5) The process for preparing aminotriazine alkoxylates according to any preceding claim wherein the mass ratio between aminotriazine alkoxylate (a) and the aminotriazine (b) is in the range from 20:80 to 95:5 and preferably in the range from 40:60 to 95:5.
- 6) The process for preparing aminotriazine alkoxylates according to any preceding claim wherein the aminotriazine alkoxylate (f) is selected from the group comprising reaction products of at least one compound of the following formula: NR'R" I) pm AN R™ where R" and R” are each selected from H, branched or linear C1-C22 compounds,polypropylene glycol and polyethylene glycol, R™ and R™ are each selected from H, NR'R", OH, halide, branched or linear C1-C22 chains, CBRS5, where R is selected from H, branched or linear C1-C22 alkyl chains, aryl, or a mixture of compounds having this formula, with at least one alkylene oxide (j).
- 7) The process for preparing aminotriazine alkoxylates according to any preceding claim wherein the aminotriazine alkoxylate (f) is present.
- 8) The process for preparing aminotriazine alkoxylates according to any one of claims 1 to 6 wherein the aminotriazine alkoxylate (f) is not present.
- 9) The process for preparing aminotriazine aikoxylates according to any preceding claim wherein the alkylene oxides (c}, (e), (h) and {i} are each independently selected from the group comprising propylene oxide, ethylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, isobutylene oxide, 1 ,2-pentene oxide, styrene oxide, epichlorohydrin, glycidol and mixtures thereof, preferably propylene oxide or ethylene oxide,
- 10) The process for preparing aminotriazine alkoxylates according to any preceding claim wherein the alkylene carbonate (9) is selected from the group comprising propylene carbonate, ethylene carbonate, glycerol carbonate and mixtures thereof.
- 11) The process for preparing aminotriazine alkoxylates according to any preceding claim wherein the aminotriazine alkoxylate (a) is obtained in the presence of a solvent.
- 12) The process for preparing aminotriazine alkoxylates according to any of claims 1 io 10 wherein the aminotriazine alkoxylate (a) is obtained in the absence of a solvent,
- 13) The process for preparing aminotriazine alkoxylates according to any preceding claim wherein the reaction of aminotriazine alkoxylate (a) with at least one aminofriazine (b) and with at least one alkylene oxide (c} is carried out at temperatures between 100 and 200°C and at pressures of 1 — 10 bar in the absence of 5 catalyst and in the absence ofa solvent,
- 14) An aminotriazine alkoxylate obtainable by the process of any of claims 1 to 13,
- 15) The use of aminotriazine alkoxylates obtainable by the process of any of claims 1 10 13 for surface-active materials, more particularly surfactants and emulsifiers, dispersants for aqueous systems, for organic solvents or for polyether polyols, solubilizers for water-
- 16 insoluble compounds {agro or pharma adjuvants), polyetherol component in polyurethane system formulations, preferably in rigid polyurethane foam or polyurethane coating formulations, more preferably in rigid polyurethane foam systems.
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US10435503B2 (en) | 2017-09-22 | 2019-10-08 | Hexion Inc. | Compositions for polyurethane applications |
US10604614B2 (en) | 2017-09-22 | 2020-03-31 | Hexion Inc. | Compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensates |
US10640475B2 (en) | 2017-09-22 | 2020-05-05 | Hexion Inc. | Compositions and methods to produce alkoxylated triazine-arlhydroxy-aldehyde condensates |
CN111019113B (en) * | 2019-12-05 | 2023-03-03 | 万华化学(宁波)容威聚氨酯有限公司 | Amino polyether polyol for pure LBA system, preparation method thereof and polyurethane rigid foam prepared by using amino polyether polyol |
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US3256281A (en) | 1963-01-04 | 1966-06-14 | Olin Mathieson | Alkoxylated mixtures of di- and triamino-1, 3, 5-triazine-polyols and a process for their production |
US3438986A (en) | 1965-05-21 | 1969-04-15 | Olin Mathieson | Oxyalkylated nitrogen compounds |
US3328321A (en) | 1966-01-27 | 1967-06-27 | Wismer Marco | Cellular polyurethanes prepared from polyhydroxy resinous reaction products of an amino-s-triazine and an alkylene carbonate or an alkylene oxide |
DE2118868A1 (en) | 1971-04-19 | 1972-10-26 | Basf Ag | Process for the preparation of alkoxylated polyamino-1,3,5-triazines |
US4039576A (en) * | 1972-03-28 | 1977-08-02 | Ciba-Geigy Corporation | Process for the manufacture of alkoxylated N-methylol ureas |
US4356304A (en) * | 1980-11-10 | 1982-10-26 | American Cyanamid Company | Synthesis of oxyalkylated polyamino-1,3,5-triazines |
EP0051734A1 (en) * | 1980-11-10 | 1982-05-19 | American Cyanamid Company | Synthesis of oxyalkylated polyamino-1,3,5-triazines |
DE3412082A1 (en) | 1984-03-31 | 1985-10-03 | Basf Ag, 6700 Ludwigshafen | POLYETHER-POLYOL MIXTURES CONTAINING S-TRIAZINE RESIDUES, METHOD FOR THE PRODUCTION AND THEIR USE |
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JPH10251399A (en) * | 1997-03-10 | 1998-09-22 | Toyo Tire & Rubber Co Ltd | Production of triazine ring-containing polyol |
US6114085A (en) * | 1998-11-18 | 2000-09-05 | Clariant Finance (Bvi) Limited | Antireflective composition for a deep ultraviolet photoresist |
KR20110014697A (en) * | 2008-05-30 | 2011-02-11 | 바스프 에스이 | Amphiphilic molecules with a triazine core |
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