US20120282210A1 - Novel organomodified siloxanes having primary amino functions, novel organomodified siloxanes having quaternary ammonium functions and the method for the production thereof - Google Patents
Novel organomodified siloxanes having primary amino functions, novel organomodified siloxanes having quaternary ammonium functions and the method for the production thereof Download PDFInfo
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- US20120282210A1 US20120282210A1 US13/521,351 US201013521351A US2012282210A1 US 20120282210 A1 US20120282210 A1 US 20120282210A1 US 201013521351 A US201013521351 A US 201013521351A US 2012282210 A1 US2012282210 A1 US 2012282210A1
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- United States
- Prior art keywords
- sio
- range
- ammonium
- group
- radical
- Prior art date
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- -1 siloxanes Chemical class 0.000 title claims abstract description 80
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 18
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 150000003254 radicals Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910020388 SiO1/2 Inorganic materials 0.000 claims description 24
- 229910020447 SiO2/2 Inorganic materials 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 229910020487 SiO3/2 Inorganic materials 0.000 claims description 6
- 229910020485 SiO4/2 Inorganic materials 0.000 claims description 6
- 239000003995 emulsifying agent Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- 238000007142 ring opening reaction Methods 0.000 claims description 6
- 239000002318 adhesion promoter Substances 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000003868 ammonium compounds Chemical class 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000001099 ammonium carbonate Substances 0.000 claims description 3
- 239000002518 antifoaming agent Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 3
- 239000004569 hydrophobicizing agent Substances 0.000 claims description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 238000009988 textile finishing Methods 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- KWIPUXXIFQQMKN-UHFFFAOYSA-N 2-azaniumyl-3-(4-cyanophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(C#N)C=C1 KWIPUXXIFQQMKN-UHFFFAOYSA-N 0.000 claims description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005695 Ammonium acetate Substances 0.000 claims description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004251 Ammonium lactate Substances 0.000 claims description 2
- 239000004254 Ammonium phosphate Substances 0.000 claims description 2
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 claims description 2
- 235000019257 ammonium acetate Nutrition 0.000 claims description 2
- 229940043376 ammonium acetate Drugs 0.000 claims description 2
- 229940090948 ammonium benzoate Drugs 0.000 claims description 2
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 claims description 2
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229940059265 ammonium lactate Drugs 0.000 claims description 2
- 235000019286 ammonium lactate Nutrition 0.000 claims description 2
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims description 2
- 235000019289 ammonium phosphates Nutrition 0.000 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- NHJPVZLSLOHJDM-UHFFFAOYSA-N azane;butanedioic acid Chemical compound [NH4+].[NH4+].[O-]C(=O)CCC([O-])=O NHJPVZLSLOHJDM-UHFFFAOYSA-N 0.000 claims description 2
- QYTOONVFPBUIJG-UHFFFAOYSA-N azane;cyanic acid Chemical compound [NH4+].[O-]C#N QYTOONVFPBUIJG-UHFFFAOYSA-N 0.000 claims description 2
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 claims description 2
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 claims description 2
- AJGPQPPJQDDCDA-UHFFFAOYSA-N azanium;hydron;oxalate Chemical compound N.OC(=O)C(O)=O AJGPQPPJQDDCDA-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- YXVFQADLFFNVDS-UHFFFAOYSA-N diammonium citrate Chemical compound [NH4+].[NH4+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O YXVFQADLFFNVDS-UHFFFAOYSA-N 0.000 claims description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 150000002118 epoxides Chemical group 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000003141 primary amines Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 150000003335 secondary amines Chemical class 0.000 description 13
- 238000003756 stirring Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000006459 hydrosilylation reaction Methods 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- 0 CC1CC2CC1C(N)C2O.CC1CC2CC1C(O)C2N.CCCC1CCC(N)C(O)C1.CCCC1CCC(O)C(N)C1.CCCCOCC(N)CO.CCOCC(N)CO.CCOCC(O)CN.CCOCC(O)CN.[6*]C(CC)C(=O)O[7*]C(N)CO.[6*]C(CC)C(=O)O[7*]C(O)CN Chemical compound CC1CC2CC1C(N)C2O.CC1CC2CC1C(O)C2N.CCCC1CCC(N)C(O)C1.CCCC1CCC(O)C(N)C1.CCCCOCC(N)CO.CCOCC(N)CO.CCOCC(O)CN.CCOCC(O)CN.[6*]C(CC)C(=O)O[7*]C(N)CO.[6*]C(CC)C(=O)O[7*]C(O)CN 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000005337 ground glass Substances 0.000 description 6
- 239000012263 liquid product Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000010517 secondary reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 150000001343 alkyl silanes Chemical class 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- 229910052723 transition metal Inorganic materials 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZPZDIFSPRVHGIF-UHFFFAOYSA-N 3-aminopropylsilicon Chemical compound NCCC[Si] ZPZDIFSPRVHGIF-UHFFFAOYSA-N 0.000 description 1
- RUVWDGDZMPTZOS-UHFFFAOYSA-N 3-cyclohex-2-en-1-yloxycyclohexene Chemical compound C1CCC=CC1OC1C=CCCC1 RUVWDGDZMPTZOS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Chemical class 0.000 description 1
- 239000002879 Lewis base Chemical class 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ZGSDJMADBJCNPN-UHFFFAOYSA-N [S-][NH3+] Chemical class [S-][NH3+] ZGSDJMADBJCNPN-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical class [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- CVEGDJIFCXGXJU-UHFFFAOYSA-N chloro(3-chloropropyl)silane Chemical class ClCCC[SiH2]Cl CVEGDJIFCXGXJU-UHFFFAOYSA-N 0.000 description 1
- BGPCFXZWLWDDDU-UHFFFAOYSA-N chloro(propyl)silane Chemical compound CCC[SiH2]Cl BGPCFXZWLWDDDU-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- KISVAASFGZJBCY-UHFFFAOYSA-N methyl undecenate Chemical compound COC(=O)CCCCCCCCC=C KISVAASFGZJBCY-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical compound [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
Definitions
- the invention relates to novel organomodified siloxanes having primary amino functions and novel organomodified siloxanes having quaternary ammonium functions and the method for the production thereof.
- Aminoalkyl-functional alkoxysilanes are used as adhesion promoters in coatings or adhesives and sealants. They are produced by the platinum(0)-catalyzed hydrosilylation of allyl chloride, as is described, for example, in DE 10104966 A1. On account of secondary reactions, propene, chloropropane and propylchlorosilane are formed, meaning that distillative purification of the product is required.
- the haloalkyl function of the 3-chloropropylchlorosilanes obtained in this way can, according to EP 1273612 A1, be further functionalized in diverse ways, for example by reaction with ammonia, hydrogen sulfide, alkali metal or ammonium sulfides, rhodanides and also methacrylates.
- the functional chlorosilanes can be converted to the corresponding alkoxysilanes.
- Aminopropylalkoxysilanes can be converted to polysiloxanes by means of hydrolysis and condensation reactions. On account of the basic amino function, preference is given to using alkaline catalysts such as, for example, KOH, ammonium hydroxide or carboxylate.
- alkaline catalysts such as, for example, KOH, ammonium hydroxide or carboxylate.
- EP 1580215 A1 and the specifications cited therein may be incorporated herewith as reference.
- This synthesis route has limits.
- the price of the expensive special silane is increasingly driving the material costs upwards and, at the same time, the yield is reduced by the amount of alcohol liberated during the hydrolysis.
- silazanes can also arise as by-products.
- EP 1008614 A2 claims linear polydimethylsiloxanes, the chain ends of which are SiC-linked with in each case one allyl polyether and one alkanolamine or alkanolalkylamine.
- the production takes place from a linear, epoxy- and polyether-functional polydimethylsiloxane by titanium-catalyzed epoxide ring opening for example with diethanolamine at 80° C.
- Polysiloxanes having primary amino functions cannot be produced by the described methods and are neither specified nor claimed.
- US 2008/0314518 A1 describes the reaction of amino-functional silanes or of ethylenediamine in situ with glycidoxypropyltriethoxysilane for producing an aqueous two-component adhesion promoter.
- the crosslinking required for good adhesion is ensured since an amino function reacts with more than one of the epoxide rings added in excess.
- the prior art discloses siloxanes with not more than two amino functions and often without further functional groups.
- Amino-functional siloxanes and in particular their charged derivatives which are accessible by reaction of the amino function with various acids or else also by their alkylation to give quaternary nitrogen compounds, have a marked electrostatic affinity towards surfaces and consequently provide for good substantivity of the compounds.
- the substantivity of the aminosiloxane being its ability to anchor itself electrostatically to substrates, is associated with its functionality density, i.e. with the number of uncharged or else also charge-carrying nitrogen functions based on the molecular weight.
- the amino-functional polysiloxanes described in EP 1008614 A2 are low molecular weight and have only one terminal amino function per chain.
- EP 1956038 A1 likewise describes only linear terminal amino-functional intermediates. Consecutive reactions of the primary amines formed lead in the first instance to chain extension and not to a gelation as a result of crosslinking. As soon as the siloxane has lateral substituents and particularly when more than two amino functions are to be linked to the siloxane, a further reaction of the primary and secondary amines leads to comparatively large viscosity increases. The gelation risk increases with increasing molar mass of the product and also, associated therewith, with increasing product viscosity. Moreover, secondary amines are toxicologically unacceptable since they form carcinogenic nitrosamines with nitrites or nitrous gas oxides from the air.
- One object of the present invention consists in producing siloxanes having primary amino functions and further organomodifications in a selective and cost-effective manner.
- the aim is to ensure a high yield of primary amino functions while simultaneously avoiding the formation of secondary amines.
- a further object of the present invention furthermore consists in developing a cost-effective method for producing siloxanes with a high chemoselectivity for the formation of primary amino groups.
- the invention therefore provides a method for producing selectively primary amino group-carrying siloxanes by reacting laterally epoxy-modified siloxanes with gaseous, dissolved or in situ generated ammonia.
- alkyl-substituted amines are relatively strong nucleophiles and thus favor further reactions of the desired product with other epoxide rings to form secondary amines over the primary reaction. This is true in particular for the case of a high functionality density and thus a high concentration of epoxide groups in the system.
- a further object of the present invention consists in modifying siloxanes not only at the chain ends, but also laterally with primary amino functions in order to achieve higher functionality densities.
- the invention provides siloxanes of the general formula 1
- the various monomer units of the building blocks given in the formulae can be constructed blockwise among one another with any desired number of blocks and be based on an arbitrary sequence or a statistical distribution.
- the indices used in the formulae are to be regarded as statistical average values.
- the invention further provides ionic adducts of the amino-functional siloxanes according to the invention with protic reactants H + A ⁇ .
- the adduct is present in the form of —NH 3 + A ⁇ .
- the anions A ⁇ are identical or different counterions to the positive charges on the protonated, primary amino groups, selected from inorganic or organic anions of the acids H + A ⁇ , and also derivatives thereof.
- Preferred anions are, for example, chloride, sulfate and hydrogensulfates, carbonate and hydrogencarbonate, phosphate and hydrogenphosphates, acetate and homologous carboxylates with linear or branched, saturated or olefinically unsaturated alkyl chains, aromatic carboxylates, carboxylates formed from amino acids, citrates, malonates, fumarates, maleates, substituted and unsubstituted succinates and carboxylates formed from L-hydroxycarboxylic acids, such as, for example, lactate.
- the aminosiloxanes according to the invention and their ionic adducts can be present in dissociation equilibria depending on the stability of the adduct formed.
- the invention provides the quaternary ammonium compounds deriving from the alkylation of the primary amine function of the formula 2
- radicals R 1 , R 3 , R 4 and R 5 likewise satisfy the definition given above and
- the compounds of the formula 1 according to the invention are reacted with the alkylating reagents.
- alkylating reagents known to the person skilled in the art, such as e.g. alkyl halides or dialkylsulfates, in particular, can be used.
- the invention furthermore provides preparations in the form of solutions, emulsions, dispersions and/or mixtures comprising the compounds according to the invention of the formulae 1 or 2.
- preparations can comprise further additives and accessory materials, for example, but not limited to those selected from the group of fillers, emulsifiers, dyes, pigments.
- the invention further provides the use of the amino-functional siloxanes of the formulae 1 or 2 according to the invention as emulsifier for cosmetic preparations, compatibilizer for plastic blends, release agent, hydrophobicizing agent, dispersant for colored pigments and fillers, additives for textile finishing (softeners), conditioner for hair, primer for surface coating/adhesion promoter, additive for corrosion protection formulations, PU foam stabilizer, antifoam and/or as wetting agent.
- the invention further provides the method for producing the aminosiloxanes of the formula 1 according to the invention.
- the compounds of formula 1 according to the invention are produced from epoxy-functional compounds of the formula 3
- radicals R 1 , R 3 , R 4 and R 5 likewise satisfy the definition specified above and R 10 independently of the others, is identical or different organic epoxy radicals.
- Suitable epoxy radicals R 10 are, for example, preferably identical or different radicals selected from the group
- the epoxy-functional siloxanes which can also carry further substituents, are produced as described in the prior art—for example in EP 0415208 A2- by means of transition metal-catalyzed hydrosilylation.
- the ring-opening reaction is then carried out with the introduction of ammonia, with or without using solvents, at atmospheric pressure or in the autoclave at superatmospheric pressure.
- the ammonia can also be generated in situ from compounds which cleave off ammonia, for example when increasing the temperature.
- a large number of customary solvents is suitable for the production according to the invention of the amino-functional siloxanes.
- the solvent is selected according to its dissolving capacity for starting material and product.
- the solvent should behave largely inertly both towards ammonia and also towards the epoxy-functional preproduct under the selected reaction conditions.
- aromatic hydrocarbons, but also ethers or alcohols are suitable.
- Preference is given to using toluene, xylene, methanol, ethanol, propanol and its isomers, in particular 2-propanol.
- reaction temperatures of up to 150° C., preferably 60° C. to 130° C.
- the pressure build-up in the closed autoclave during heating can be in the range from 1 to 50 bar, preferably 5 to 20 bar.
- a closed pressurized reactor is charged with ammonia gas via a gassing device, a pregiven pressure of 1 to 50 bar, preferably from 5 to 20 bar, can be established during the charging.
- the reaction times can be 1 to 10 hours, preferably 1 to 5 hours.
- a particular advantage of the method at pressures greater than 1 bar and at temperatures above 50° C. is that, compared to the prior art, it is possible to realize shorter reaction times of less than 12 hours.
- the higher local concentration of ammonia in the dissolved phase influences the selectivity in a positive manner since the ratio of ammonia to the formed primary amine, i.e. of the reagents competing for the ring openings, is increased in favor of the ammonia.
- Preferred process pressures are in the range from 2 to 50 bar, in particular 5 to 20 bar.
- a further advantage of the higher reaction temperature is evident in the case of the reaction of relatively high molecular weight epoxy siloxanes.
- the viscosity of the starting compounds is reduced at higher temperatures, which facilitates the mixing and the mass transfer and thus likewise brings about a rapid reaction.
- the higher reaction temperature likewise brings about a more rapid degassing of the ammonia, it may be advantageous to work on a small scale with a gas frit and on a production scale with a bubble-column reactor.
- a minimum temperature of 50° C. preferably of 60° C.
- Heterogeneous or homogeneous catalysts from the area of acids, Lewis acids or bases, and also metal salts or complexes, or transition metal salts or complexes can be used.
- the reaction can be carried out in a one-pot method or continuously.
- the product is distilled off in order to remove residual ammonia and optionally also the solvent used.
- the pH can be adjusted by means of solid or dissolved buffer systems. If a pH adjustment is carried out with solid salts, a filtration step then follows. In the event of product clouding arising, a filtration does not necessarily have to take place.
- Ammonia can be used as a reagent not only in molecularly gaseous form or in the form of a saturated solution, but can also be used in chemically bonded form.
- amine and/or ammonium compounds which release ammonia at elevated temperatures with decomposition or else during hydrolysis in solution, such as, for example, ammonium halides, ammonium carbonate and/or hydrogencarbonate, ammonium sulfate and/or hydrogensulfate, ammonium sulfamate, ammonium phosphate, hydrogenphosphate and/or dihydrogenphosphate, ammonium cyanate, ammonium carboxylates such as, for example, ammonium acetate, ammonium hydrogenoxalate and/or oxalate, ammonium hydrogencitrate, ammonium benzoate, ammonium formate, ammonium carbamate, ammonium lactate
- organomodified polysiloxanes which can have different monomer units several times, then these can occur in these compounds in random distribution (random oligomer) or in an ordered manner (block oligomer). Data relating to the number of units in such compounds is to be understood as meaning statistical average values, averaged over all of the corresponding compounds.
- ammonia is introduced into a solution of 100 g of ethanol and 1.0 g of 1-methylimidazole (99%, Sigma Aldrich) and, at 50° C. with stirring, 100 g of the epoxy-functional polyethersiloxane are added dropwise via a dropping funnel over a period of 1.5 hours. When the metered addition is complete, ammonia is introduced for a further 4 hours at 50° C. Distillation on a rotary evaporator at 70° C.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010001531.8 | 2010-02-03 | ||
| DE102010001531A DE102010001531A1 (de) | 2010-02-03 | 2010-02-03 | Neuartige organomodifizierte Siloxane mit primären Aminofunktionen, neuartige organomodifizierte Siloxane mit quaternären Ammoniumfunktionen und das Verfahren zu deren Herstellung |
| PCT/EP2010/070855 WO2011095261A1 (de) | 2010-02-03 | 2010-12-29 | Neuartige organomodifizierte siloxane mit primären aminofunktionen, neuartige organomodifizierte siloxane mit quaternären ammoniumfunktionen und das verfahren zu deren herstellung |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2010/070855 A-371-Of-International WO2011095261A1 (de) | 2010-02-03 | 2010-12-29 | Neuartige organomodifizierte siloxane mit primären aminofunktionen, neuartige organomodifizierte siloxane mit quaternären ammoniumfunktionen und das verfahren zu deren herstellung |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/548,724 Division US9695202B2 (en) | 2010-02-03 | 2014-11-20 | Organomodified siloxanes having primary amino functions, novel organomodified siloxanes having quaternary ammonium functions and the method for the production thereof |
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| Publication Number | Publication Date |
|---|---|
| US20120282210A1 true US20120282210A1 (en) | 2012-11-08 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US13/521,351 Abandoned US20120282210A1 (en) | 2010-02-03 | 2010-12-29 | Novel organomodified siloxanes having primary amino functions, novel organomodified siloxanes having quaternary ammonium functions and the method for the production thereof |
| US14/548,724 Expired - Fee Related US9695202B2 (en) | 2010-02-03 | 2014-11-20 | Organomodified siloxanes having primary amino functions, novel organomodified siloxanes having quaternary ammonium functions and the method for the production thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/548,724 Expired - Fee Related US9695202B2 (en) | 2010-02-03 | 2014-11-20 | Organomodified siloxanes having primary amino functions, novel organomodified siloxanes having quaternary ammonium functions and the method for the production thereof |
Country Status (8)
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| US20120247363A1 (en) * | 2009-12-22 | 2012-10-04 | Lecomte Jean-Paul H | Aqueous Emulsions Of Alkylalkoxysilanes |
| US8722836B2 (en) | 2011-12-16 | 2014-05-13 | Evonik Industries Ag | Siloxane nitrones and use thereof |
| EP2840087A1 (de) | 2013-08-23 | 2015-02-25 | Evonik Degussa GmbH | Guanidingruppen aufweisende semi-organische Siliciumgruppen enthaltende Verbindungen |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2013518945A (ja) | 2013-05-23 |
| US9695202B2 (en) | 2017-07-04 |
| DE102010001531A1 (de) | 2011-08-04 |
| WO2011095261A1 (de) | 2011-08-11 |
| US20150080593A1 (en) | 2015-03-19 |
| EP2531547A1 (de) | 2012-12-12 |
| CN102741326A (zh) | 2012-10-17 |
| CA2788748A1 (en) | 2011-08-11 |
| BR112012019049A2 (pt) | 2016-09-13 |
| CN102741326B (zh) | 2015-07-15 |
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