Patent EP-2103622-A1 (EP)
Inventor: CHROBACZEK HARALD DR
IPC: C07F7/18
Filed: 2008-03-20
Abstract: Monomeric silane compound (XXXV) obtained by reacting a silane compound (II) with a polyether amine compound (III), or a compound (T), which is e.g. 3-morpholin-4-yl-propylamine or 3-(2-aminoethyl)-aminopropyl-methyl-silsesquioxane with terminal methoxy group, is new. Monomeric silane compound of formula ((RO) 2-Si(R 20>)(R 1>)) (XXXV) obtained by reacting a silane compound of formula (II) with a polyether amine compound (III) of formula (CH 3-(O-CH 2-CH 2) k-(O-CH 2-CH(CH 3) l-NH 2)), or (NH 2-(CH(CH 3)-CH 2-O) l-CH 2-CH(CH 3)-NH 2) or H 2N-CH(CH 3)-CH 2-(O-CH 2-CH(CH 3) l-(O-CH 2-CH 2) k-(O-CH 2-CH(CH 3)) l-NH 2, or NH 2-CH(CH 3)-CH 2-(O-CH(CH 3)-CH 2) w-O-CH 2-C-(CH 2-O-(CH 2-CH(CH 3)-O) w-CH 2-CH(CH 3)-NH 2) 3, or a compound (T), which is 3-morpholin-4-yl-propylamine, H 2N-CH 2-CH 2-CH 2-Si(CH 3)-(O-Si(CH 3) 3) 2, HO-(CH 2-CH 2-O) k-((CH(R 3>)) 2-O) l-CH 2-CH 2-CH 2-Si(CH 3)-(O-Si(CH 3) 3)) 2or 3-(2-aminoethyl)-aminopropyl-methyl-silsesquioxane with terminal methoxy group, is new. R : phenyl residue or 1-18C-alkyl, preferably CH 3or CH 2-CH 3; R 1>R, OR or methyl-phenyl-amine moiety; R 20>-R 21>-NH-(CH 2) 2-C(=O)-O-R 22>-O-C(=O)-(CH 2) 2-NH-R 21>-Si(OR) 2(R 1>) (XXXVI), -R 21>-NH-(CH 2) 2-C(=O)-O-R 23>(XXXVII), -R 21>-NH-(CH 2) 2-C(=O)-O-(CH 2-CH 2-O) k-(CH(R 3>)-CH(R 3>)-O) l-R23a) (XXXVIII), -R 22>-NH-(CH 2) 2-C(=O)-N(R 24>) 2(XXXIX), -R21a-CH(OH)-CH 2-NH-R21a-NH-CH 2-CH(OH)-R21a-Si(OR) 2(R 1>) (XL), silane substituted cyclohexane group of formula (XL1), -R 21>-NH-C(=O)-O-CH 2-CH(R)-OH (XL1a), -R 21>-NH-C(=O)-O-CH(R)-CH 2-OH (XL1b), -R 21>-NH-CH 2-CH(R)-OH (XL1c), -R 21>-NH-CH(R)-CH 2-OH (XL1d), -R 21>-NH-C(=O)-O-CH 2-CH(R)-O-C(=O)-CH=CH 2(XL1e), -R 21>-NH-C(=O)-O-CH(R) -CH 2-O-C(=O)-CH=CH 2(XL1f), -R 21>-NH-CH 2-CH(R)-O-C(=O)-CH=CH 2(XL1g) or -R 21>-NH-CH(R)-CH 2-C(=O)-CH=CH 2(XL1h); R 21>3-8C-alkylene (which is interrupted by one or more NH-bonds), or formula (i); R21a : R 21>or a bivalent residue of formula -CH 2-CH 2-NH-CH 2-CH(CH 3)-CH 2-Si(CH 3) 2-O-Si(CH 3) 2-CH 2-CH(CH 3)-CH 2-NH-CH 2-CH 2-; R 22>6-18C-alkylene, -CH 2-CH 2-O-C(=O)-NH-R 21>-NH-C(=O)-O-R 21>-O-C(=O)-NH-R 21>-NH-C(=O)-O-CH 2-CH 2-, or -CH 2-CH 2-O-C(=O)-(CH 2) 5-O-C(=O)-NH-R 21>-NH-C(=O)-O-CH 2-CH 2-; R 23>8-16C-alkyl, -(CH 2-CH 2-O-), or -(CH(R 3>)-CH(R 3>)-O-); R23a : 8-16C-alkyl or H; R 3>H or CH 3; either k, l : 1-22; or k+l : 3-25; R 24>1-6C-alkyl; x : 0-1500, preferably 10-1500; and w : 2-8. An independent claim is included for a polyorganosiloxane compound obtained by reacting polyorganosiloxane compound of formula ((R 7>)(R) 2-Si-O-(Si(R)(R 6>)-O) x-Si(R) 2(R 7>)) (VIII) or its mixture with (XXXV) or a silane compound of formula (Si(OR) 2(R 1>)(R 2>)) (I). R 6>R or -(O-Si(R) 2) y-O-Si(R) 2-R 7>(IX); y : 0-500; R 7>R, OH or OR; R 2>vinyl residue, 1-18C-alkyl (which is optionally substituted by one or more quaternary amino-, amido-, mercapto-, epoxy-, phosphono- group, OH or F), -R 4>-O-CH 2-CH(O-R 5>)-CH 2-O-R 5>, -R 4>-NH-C(=O)-(CH 2) 3-O-C(=O)-C(R 3>)=CH 2, -R 4>-NH-((CH 2) 2-NH) p-C(=O)-(CH 2) 3-O-C(=O)-C(R 3>)=CH 2, -R 4>-O-C(=O)-C(R 3>)=CH 2, -(CH 2) 3-O-CH 2-C(R)-(CH 2-O-C(=O)-C(R 3>)=CH 2) 2, -R 4>-NH-CH(R 9>)-CH(R 3>)-COOR 8>, -R 4>-NH-CH 2-CH 2-NH-CH(R 9>)-CH(R 3>)-COOR 8>, -R 4>-R 10>-R 4>-Si(OR) 2(R 1>), -R 4>-(NH-CH 2-CH 2) p-NH-(CH(R 3>)) 2-C(=O)-N(R) 2, -R 4>-(NH-CH 2-CH 2) p-NH-(CH(R 3>)) 2-C(=O)-O-R 14>, -R 4>-(NH-CH 2-CH 2) p-NH-C(=O)-CH 2-CH 2-CH 2-OH, methyl-phenyl-amine moiety, -R 4>-(N(R 16>)-CH 2-CH 2) p-N(R 16>)-(C(=O)-O) f-CH(R)-CH 2-OH, -R 4>-(N(R 16>)-CH 2-CH 2) p-N(R 16>)-(C(=O)-O) f-CH(R)-CH 2-O-C(=O)-CH=CH 2, -R 4>-O-CH 2-CH(OH)-CH 2-NH-(CH 2-CH 2-O) u-A-((CH(R 3>)) 2-O-) v-R 17>, -R 4>-O-CH 2-CH(OH)-CH 2-N(R 13>)-(CH 2) 3-M, hydroxyl group substituted cyclohexane group of formula (XVIIIa), -R 4>-O-CH 2-CH(OH)-CH 2-O-(CH 2-CH 2-O) k-((CH(R 3>)) 2-O) l-(CH 2) 3-Si((O-Si(CH 3) 3) 2(CH 3), -R 4>-(NH-CH 2-CH 2) p-NH-CH 2-CH(OH)-CH 2-RF, -R 4>-(NH-CH 2-CH 2) p-NH-CH(CH 2OH)-RF, -R 4>-(NH-CH 2-CH 2) p-NH-CH 2-CH(OH)-CH 2-O-C(=O)-C(R 3>)=CH 2or -R 4>-(NH-CH 2-CH 2) p-NH-CH 2-CH(OH)-CH 2-NR 2>; A : a direct bond or a divalent residue of formula -CH 2-C(R 12>)(CH 2-O-(CH(R 3>)) 2-O) s-R 17>)-CH 2-O-; R 5>(-C(=O)-C(R 3>)=CH 2) or H; p : 0-2; R 4>a bivalent 1-4C-hydrocarbon; R 8>H, CH 3, C 2H 5or CH 2CH 2-OH; R 9>H or COOR 8>; R 14>H, 1-18C-alkyl or -R 4>-O-CH 2-CH(OH)-CH 2-O-(CH 2-CH 2-O) k-((CH(R 3>)) 2-O) l-(CH 2) 3-Si(OSi(CH 3) 3) 2(CH 3) (where the single units -(CH 2-CH 2-O)- and -(CHR 3>-CHR 3>-O)-); f : 0 or 1; R 16>H, -(C(=O)-O) f-CH(R)-CH 2-OH or -(C(=O)-O) f-CH(R)-CH 2-O-C(=O)-CH=CH 2; u, v, s : a value, which makes the equivalent weight of the residue R 2>of 100-5000, where one or two of u, v and s is 0; R 12>H or C 2H 5; R 17>R, -R 4>-NH 2or -CH 2-CH(CH 3)-NH-CH 2-CH(OH)-CH 2-O-R 4>-Si(OR) 2(R 1>); M : OR, N(R) 2, morpholine or -Si(CH 3)-(OSi(CH 3) 3) 2; RF : 5-23C-perfluoroalkyl; R 10>a divalent residue of formula -O-CH 2-CH(OH)-CH 2-N(R 13>)-R 11>-N(R 13>)-CH 2-CH(OH)-CH 2-O-, hydroxyl group substituted cyclohexane group of formula (XXII), -(NH-CH 2-CH 2) p-NH-(CH(R 3>)) 2-C(=O)-O-K 1>-O-C(=O)-(CH(R 3>)) 2-NH-(CH 2-CH 2-NH) p-, amide substituted cyclohexane group of formula (XXIV), or substituted benzene group of formula (XXIVa), -(CH 2) 2-NH-(CH 2) 2-, piperazine group of formula (XXVI), bis-methyl-benzen-1,4-yl, 1-chloro-4-[(4-chlorophenyl)methyl]benzene, methyl-1,3,3-trimethyl-cyclohexan-1,5-yl, -(CH 2) 2-NH-R 4>-(Si(R) 2-O) z-Si(R) 2-R 4>-NH-(CH 2) 2or -R 4>-(Si(R) 2-O) z-Si(R) 2-R 4>-, where complete or a part of N in the above formula are not a part of an amide group and exists in quaternized form; z : 8-500, preferably 8-20; f : 0 or 1; K 1>2-18C-alkylene; R 11>-(CH 2) d-; d : 1-6; and R 13>H, CH(CH 3) 2or CH 2-CH(CH 3) 3. 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