Quaternary compounds, compositions containing them, and uses thereof

A composition comprising a compound selected from the group consisting of compounds of the following structural formula (2A):

• and the protonated and quaternized derivatives thereof of the following structural formula (2B):
• wherein R1 is a C14 to C22 hydrocarbyl group;
• each R2 is independently selected from the group consisting of hydrogen, a C1 to C22 hydrocarbyl group,
• and R3)yH, where y is 1 to 100;
• each R3 is independently selected from the group consisting of an ethylene oxide group (C2H4O), a propylene oxide group (C3H6O), a butylene oxide group (C4H8O) and mixtures thereof;
• each R4 is independently a C3 to C21 hydrocarbyl group;
• each R5 is independently a hydrogen or a C1 to C6 hydrocarbyl group, where each w is independently 0 or 1;
• each R6 is independently a C1 to C6 hydrocarbyl group;
• x is 3 to 100;
• z is 1, 2, 3, 4 or 5;
• and
• A− is an anion that balances the charge of the compounds.

A paper web comprising:

• (a) papermaking fiber;
• and
• (b) a compound selected from compounds of the group consisting of compounds of the following structural formula (1)B):
• wherein
• R1 is a C14 to C22 hydrocarbyl group;
• R2 is hydrogen or a C1 to C22 hydrocarbyl group, or is
• or (R3)yH, where y is 1 to 100;
• each R3 is independently selected from a group consisting of an ethylene oxide group (C2H4O), a propylene oxide group (C3H6O), a butylene oxide group (C4H8O) and mixtures thereof;
• each R4 is a C3 to C2, hydrocarbyl group;
• R5 is hydrogen or a C1 to C8 hydrocarbyl group;
• and
• x is 3 to 100;
• and
• A− is an anion.

A paper web comprising:

• (a) papermaking fiber;
• and
• (b) a compound selected from compounds of the following structural formula (2A):
• and the protonated and quaternized derivatives thereof of the following structural formula (2B):
• wherein R1 is a C14 to C22 hydrocarbyl group;
• each R2 is independently selected from the group consisting of hydrogen, a C1 to C22 hydrocarbyl group,
• and (R3)yH, where y is 1 to 100;
• each R3 is independently selected from the group consisting of an ethylene oxide group (C2H4O), a propylene oxide group (C3H6O), a butylene oxide group (C4H8O) and mixtures thereof;
• each R4 is independently a C3 to C21 hydrocarbyl group;
• each R5 is independently a hydrogen or a C1 to C6 hydrocarbyl group, where each w is independently 0 or 1;
• each R6 is independently a C1 to C6 hydrocarbyl group;
• x is 3 to 100;
• z is 1, 2, 3, 4 or 5;
• and
• A− is an anion that balances the charge of the compounds.

A method of treating a paper web comprising applying to the paper web a composition which comprises at least one compound of structural formula (1B):

• wherein
• R1 is a C14 to C22 hydrocarbyl group;
• R2is hydrogen or a C1 to C22 hydrocarbyl group, or is
• or (R3)yH, where y is 1 to 100;
• each R3 is independently selected from a group consisting of an ethylene oxide group (C2H4O), a propylene oxide group (C3H6O), a butylene oxide group (C4H8O) and mixtures thereof;
• each R4 is a C3 to C2, hydrocarbyl group;
• R5 is hydrogen or a C1 to C8 hydrocarbyl group;
• and
• x is 3 to 100;
• and
• A− is an anion;
• or at least one compound of structural formula (2A):
• or the protonated and quaternized derivatives thereof of the following structural formula (2B):
• wherein R1 is a C14 to C22 hydrocarbyl group;
• each R2 is independently selected from the group consisting of hydrogen, a C1 to C22 hydrocarbyl group,
• and (R3)yH, where y is 1 to 100;
• each R3is independently selected from the group consisting of an ethylene oxide group (C2H4O), a propylene oxide group (C3H6O), a butylene oxide group (C4H8O) and mixtures thereof;
• each R4 is independently a C3 to C21 hydrocarbyl group;
• each R5 is independently a hydrogen or a C1 to C6 hydrocarbyl group, where each w is independently 0 or 1;
• each R6 is independently a C1 to C6 hydrocarbyl group;
• x is 3 to 100;
• z is 1, 2, 3, 4 or 5;
• and
• A− is an anion that balances the charge of the compounds.

An organoclay composition made by the reaction of:

• (a) one or more clays;
• (b) one or more compounds selected from the group consisting of:
• (i) compounds of the following structural formula (1B):
• (ii) compounds of the following structural formula (2B):
• wherein
• R1 is a C14 to C22 hydrocarbyl group;
• each R2 is independently selected from the group consisting of hydrogen, a C1 to C22 hydrocarbyl group,
• and (R3)yH, where y is 1 to 100;
• each R3 is independently selected from the group consisting of an ethylene oxide group (C2H4O), a propylene oxide group (C3H6O), a butylene oxide group (C4H8O) and mixtures thereof;
• each R4 is independently a C3 to C21 hydrocarbyl group;
• each R5 is independently a hydrogen or a C1 to C6 hydrocarbyl group, where each w is independently 0 or 1;
• each R6 is independently a C3 to C8 hydrocarbyl group;
• x is 3 to 100;
• z is 1, 2, 3, 4 or 5;
• and
• A− is an anion that balances the charge of the compounds;
• and
• (c) one or more quaternary compounds of the structural formula:
• wherein each of R* and R** is independently a linear, branched or cyclic alkylene group containing 2 to 12 carbon atoms, wherein no two nitrogen atoms are separated by fewer than 2 carbon atoms;
• each of A1, A2, A3, A4, and A5 is independently a straight or branched alkylene containing 2 to 4 carbon atoms;
• each of R26, R27, R28, R29, and R30 is independently —H or RAC(O)— wherein RA is straight or branched alkyl or alkenyl containing 7 to 21 carbon atoms and 0 to 4 carbon-carbon double bonds;
• provided that at least one of R26, R27, R28, R29, or R30 is RAC(O)—;
• each of Q1, Q2 and Q3 is independently —H, —CH3, —C2H5, —C3H7, —C4H5, benzyl, —CH2COOH, or —CH2COOX−;
• or, if R* is a —CH2CH2— group, Q1 and Q3 together or Q1 and Q2 together can be a —CH2CH2— group to form a six-membered piperazine ring;
• or, if R** is a —CH2CH2— group, Q2 and Q3 together can be a —CH2CH2— group to form a six-membered piperazine ring;
• m is 0 to 4;
• r is 0 to 2;
• each of v, w, x, y, and z is independently 1 to 8;
• i is 0 to 1, j is 0 to 1, and each k is 0 to 1, and the sum of (i+j+k) is 0 to;
• 3 with the proviso that when r=2, then the sum of (i+j+k) is 4;
• each X− is independently an anion selected from the group consisting of fluoride, chloride, bromide, iodide, chlorite, chlorate, hydroxide, hypophosphite, phosphite, phosphate, carbonate, formate, acetate, lactate, oxalate, methyl sulfate, ethyl sulfate, benzoate, and salicylate;
• and n is the number of moles of X− needed to give the quaternary ammonium compound a zero net charge.