Ester-modified organosilicon-based surfactants, methods of making same and applications containing the same

A polyalkylene-oxide-free surfactant composition comprising an ester-modified organosilicon having the general formula (I):

• AOaR4b(BOcR11d)e(C)fDg (I)
• where
• A=R1R2R3Si—
• B=—Si(R5)(R6)
• C=R7R8R9Si—
• D=—O(R14)pR19
• where R4 and R11 are each independently selected from a branched or linear divalent hydrocarbon radical of 1 to 12 carbons, subscripts a, b, c, d, e, f, g and p are each 0 or 1 and subject to the following provisos:
• a+b=1;
• when e=1, c+d=1;
• and, when g=1, then a+e+f=0;
• R1R2R3R5R7R8 are each independently selected from the group consisting of monovalent hydrocarbon radicals having from 1 to 8 carbon atoms, and an aryl or alkaryl hydrocarbon radical of from 6 to 12 carbon atoms, and R10;
• where each R10 is independently selected from the group consisting of branched monovalent hydrocarbon radicals of from 3 to 6 carbon atoms;
• R6 and R9 are each independently selected from the group consisting of linear or branched monovalent hydrocarbon radicals containing from 1 to 8 carbon atoms, and R12, provided that in formula (I) R6 and R9 are different and one of R6 and R9 is R12,
• wherein R12 is —R13O(R4), R9 or a cyclohexyl group of the general formula (Q):
• where R13 is selected from a branched or linear divalent hydrocarbon radical containing from 3 to 12 carbon atoms, which is optionally —OH substituted;
• R14 is selected from —CH2CH(R20)CH2O—, —CH2(CH2)xCH(R20)CH2O—, and a bridging group of the general formula (Y):
• —[C2H4O]h—[C3H6O]i—[C4H8O]j—[C2H4O]k—[CH2CH(R20)CH2O]n— (Y);
• wherein subscripts h, i, j, and k are zero or one and satisfy the following relationships:
• 0≦h+i+j+≦1, and 0≦h+k≦1
• R20 is H, OH or —OR19,
• subscript x is from 1 to 9,
• subscripts p and n are 0 or 1, and
• R15 and R16 are each independently selected from H or methyl;
• R17 and R18 are each independently OH or —OR19;
• provided that in formula (Q) R17 and R18 are the same or different, and at least one of R17 and R18 is OR19,
• where R19 is derived from the esterification of the corresponding hydroxy carboxylic acid or a mixture of corresponding hydroxy carboxylic acids, which hydroxy carboxylic acid(s) contain(s) from 2 to 8 carbon atoms,
• and where R19 is of the general formula (Z):
• —C(═O)—CR21R22R23 (Z)
• where R21, R22, R23 are each independently selected from H, —OH, —CH2OH, —OZ, —(R24)mO—R27, —CH3, —CH2CH3, and —(R24)mO—C(═O(CR25R26)tCH2OR27
• where R24 is a divalent hydrocarbon radical of 1 to 3 carbon atoms,
• R25 and R26 are each independently selected from H, —OH, —CH2OH, —OZ, —(R24)mO—R27, —CH3, —CH2CH3, and —(R24)mO—C(═O)—(CR25R26)tCH2OR27
• R27 is independently selected from H, Z, —CH2OH, —CH3, —CH2CH3, and [—C(═O)(CR25R26)tCH2O]w—R29,
• R29 is independently selected from H, —CH2OH, —CH3, and —CH2CH3
• subscript m is 0 to 3, t is 1 to 5 and w is 1 to 5;
• the number of Z groups in R19 is between 1 and 10;
• and, provided that when any one or more of R21, R22 and R23 are of the formula —(R24)mO—C(═O)—(CR25CR26)tCH2OR27 that R21, R22 or R23 group contains from 1 to 10 —(R24)mO—C(═O)—(CR25CR26)tCH2OR27 groups.