Hydrophobic coating compositions

A coating composition, comprising:

• (i) an organic binder;
• and
• (ii) a polyorganosiloxane of formula (IIA):
• wherein Z1, Z2, Z3 and Z4 can be same or different, wherein the subscript n is 0 or an integer of from 1 to 20, the subscript m is 0 or an integer of from 1 to 20, the subscript o is 0 or an integer of from 1 to 20,
• wherein R or R′ is a saturated hydrocarbon substituent selected from a group consisting of a monovalent alkyl containing from 1 to 22 carbon atoms, optionally substituted by F, an aryl containing from 6 to 22 carbon atoms, a polycyclic aryl containing from 8 to 22 carbon atoms, a alkylaryl containing from 7 to 22 carbon atoms, an arylalkyl group containing from 7 to 22 carbon atoms, and H;
• or L1-Z1, L2-Z2, L3-Z3 or L4-Z4, and wherein R, and R′ can be the same or different;
• wherein Z1, Z2, Z3 or Z4 of formula (IIA) is a monovalent group selected from the group consisting of R, R′, R1;
• an alkylarylalkyl containing from 8 to 22 carbon atoms;
• an aryl ether containing from 6 to 22 carbon atoms;
• a cycloalkyl containing from 6 to 22 carbon atoms;
• a cycloalkylalkylene containing from 7 to 22 carbon atoms;
• a bicycloalkyl containing from 7 to 22 carbon atoms;
• cyclothioalkyl containing from 6 to 12 carbon atoms;
• an aryl containing 5 to 12 carbon atoms and a hetero atom selected from the group consisting of —N, —O, and —S;
• an alkyl aldehyde containing from 1 to 20 carbon atoms;
• and an alkylaryl aldehyde containing from 7 to 20 carbon atoms, each of which groups can optionally be substituted by an alkyl of 1 to 8 carbon atoms, OH, Cl, or Br, or a silyl ether group R13Si—O—,
• wherein R1 is a monovalent unsaturated, unsubstituted or substituted alkenyl or alkynyl group selected from the group consisting of an alkenyl containing from 2 to 22 carbon atoms, a cycloalkenyl containing from 6 to 22 carbon atoms, a bicycloalkenylalkylene containing from 7 to 22 carbon atoms, an acrylate group, a methacrylate group, an alkynyl containing from 2 to 22 carbon atoms, and oxiranyl and carbonate derivatives of the respective R1 groups, and oxiranyl groups containing 3 to 22 carbon atoms, carbonate groups containing from 4 to 23 carbon atoms, Cl, Br, I, —SH, —S—R, —OH, —O—R, —CN, —NCO, and blocked —NCO, (X)x(Y)3-xSi—, R6xR′3-xSi—, a polyether group, carboxy (—COOH), diacids, diesters, polyester moiety, nitro-alkyl-, cyano-alkyl-, acyl- or alkyl sulfonyl fluoride- groups and, an ionic group derived from an ester of a carboxylic acid, sulphonic acid or phosphonic acid, phosphines, an amino group, a primary amine, a secondary amine, a tertiary amine, a keto group, and betaines,
• and wherein R is as defined above, and the subscript x is an integer of from 1 to 3, X and Y are each selected from the group consisting of OH, OR′, —N(R′)2, R′ O(O)—O—, and R′, wherein R′ is as defined above, and X and Y can be same or different, and wherein each R6 is an aryl containing from 6 to 10 carbon atoms, an arylalkyl containing from 7 to 12 carbon atoms, a cycloalkyl containing from 6 to 12 carbon atoms, a bicycloalkyl containing from 7 to 16 carbon atoms, an epoxy alkyl containing from 3 to 12 carbon atoms, an epoxy cycloalkyl containing from 6 to 12 carbon atoms, an epoxy bicycloalkyl containing from 7 to 16 carbon atoms, thiocycloalkyl containing from 6 to 12 carbon atoms, and an aryl containing from 5 to 12 carbon atoms, wherein the aryl, arylalkyl, or cycloalkyl contains hetero substitutions of one or more of a —N, —O, and —S— atom;
• and wherein Z1, Z2, Z3 and Z4 can be same or different;
• and
• wherein each L1, L2, L3 and L4 is selected from the group consisting of a single bond, a divalent alkylene group having at least two carbon atoms, and a trivalent group;
• optionally the two carbon atoms of the divalent alkylene group is interrupted by one or more of —O—, —NR3—C(O)—, —NR3—, —OC(O)NR3—, and/or —NR3—C(O)—NR3— moieties bonded via carbon bond of L1 or L2 to the silicon atom of the respective siloxy unit of the polyorganosiloxane (I) and wherein R3 is hydrogen, Me3Si— or an alkyl containing from 1 to 8 carbon atoms, optionally the divalent alkylene group is substituted by one or more OH groups,
• and wherein L1, L2, L3 and L4 can be same or different.

A process of making a coating composition comprising, combining:

• (i) an organic binder;
• and
• (ii) a polyorganosiloxane of formula (I):
• Z1-L1{[Si(R)(R′)O]p—SiR″2}m-L2-Z2 (I);
• wherein the subscript p>9,
• wherein the subscript m is an integer of from 1 to 5,
• wherein each R, R′ or R″ is selected from the group consisting of a saturated hydrocarbon substituent selected from the group consisting of a monovalent alkyl containing from 1 to 22 carbon atoms, optionally substituted by F or a —OH group, an aryl containing from 6 to 22 carbon atoms, a polycyclic aryl containing from 8 to 22 carbon atoms, an alkylaryl containing from 7 to 23 carbon atoms, and an arylalkyl group containing from 7 to 22 carbon atoms, and H, or L1-Z1 or L2-Z2, and wherein each R, R′ and R″ can be same or different;
• wherein, each L1 or L2 is selected from the group consisting of a single bond, a divalent alkylene group having at least two carbon atoms, optionally interrupted by one or more of —O—, —NR3—C(O)—, and/or —NR3—, —OC(O)NR3—, —NR3—C(O)—NR3— moieties bonded via carbon bond of L1 or L2 to the silicon atom of the respective siloxy unit of the polyorganosiloxane (I), and optionally substituted by one or more OH groups, or is a trivalent group, and wherein L1 and L2 can be same or different, and wherein R3 is hydrogen, Me3Si— or an alkyl containing from 1 to 8 carbon atoms,
• wherein Z1 or Z2 is a monovalent group selected from the group consisting of R, R′, R″, R1, an alkylarylalkyl containing from 8 to 22 carbon atoms, an aryl ether containing from 6 to 22 carbon atoms, a cycloalkyl containing from 6 to 22 carbon atoms, a cycloalkylalkylene containing from 7 to 22 carbon atoms, a bicycloalkyl containing from 7 to 22 carbon atoms, cyclothioalkyl containing from 6 to 12 carbon atoms, an aryl containing 5 to 12 carbon atoms and a hetero atom selected from the group consisting of —N, —O, and —S, an alkyl aldehyde containing from 1 to 20 carbon atoms, and an alkylaryl aldehyde containing from 7 to 20 carbon atoms, and wherein Z1 or Z2 is optionally substituted by an alkyl of from 1 to 8 carbon atoms,
• wherein each R1 is a monovalent unsaturated, unsubstituted or substituted alkenyl or alkynyl group selected from the group consisting of an alkenyl containing from 2 to 22 carbon atoms;
• a cycloalkenyl containing from 6 to 22 carbon atoms;
• a bicycloalkenylalkylene containing from 7 to 22 carbon atoms;
• an acrylate group;
• a methacrylate group;
• an alkynyl containing from 2 to 22 carbon atoms;
• and oxiranyl and carbonate derivatives of the respective R1 groups;
• and oxiranyl groups containing 3 to 22 carbon atoms;
• carbonate groups containing from 4 to 23 carbon atoms;
• Cl, Br, I, —SH, —S—R, —OH, —O—R, —CN, —NCO, and blocked —NCO, (X)x(Y)3-xSi—, R6xR′3-xSi—;
• a polyether group, carboxy (—COOH), diacids, diesters, a polyester group, nitro-alkyl-, cyano-alkyl-, acyl- or alkyl sulfonyl fluoride- groups and, an ionic group derived from an ester of a carboxylic acid or sulphonic acid, or phosphonic acid, phosphonate, phosphines, amines, a keto group, and betaines,
• and wherein R is as defined above, and the subscript x is an integer of from 1 to 3, X and Y are each selected from the group consisting of OH, OR′, —N(R′)2, R′ O(O)—O—, and R′, wherein R′ is as defined above, and X and Y can be same or different, and wherein each R6 is an aryl containing from 6 to 10 carbon atoms, an arylalkyl containing from 7 to 12 carbon atoms, a cycloalkyl containing from 6 to 12 carbon atoms, a bicycloalkyl containing from 7 to 16 carbon atoms, an epoxy alkyl containing from 3 to 12 carbon atoms, an epoxy cycloalkyl containing from 6 to 12 carbon atoms, an epoxy bicycloalkyl containing from 7 to 16 carbon atoms, thiocycloalkyl containing from 6 to 12 carbon atoms, and an aryl containing from 5 to 12 carbon atoms, wherein the aryl, arylalkyl, or cycloalkyl contains hetero substitutions of one or more of a —N, —O, and —S— atom.

A process of making a coating composition comprising, combining:

• (i) an organic binder;
• and
• (ii) a polyorganosiloxane of formula (IIA):
• wherein Z1, Z2, Z3 and Z4 can be same or different, wherein the subscript n is 0 or an integer of from 1 to 20, the subscript m is 0 or an integer of from 1 to 20, the subscript o is 0 or an integer of from 1 to 20,
• wherein R or R′ is a saturated hydrocarbon substituent selected from a group consisting of a monovalent alkyl containing from 1 to 22 carbon atoms, optionally substituted by F, an aryl containing from 6 to 22 carbon atoms, a polycyclic aryl containing from 8 to 22 carbon atoms, a alkylaryl containing from 7 to 22 carbon atoms, an arylalkyl group containing from 7 to 22 carbon atoms, and H;
• or L1-Z1, L2-Z2, L3-Z3 or L4-Z4, and wherein R, and R′ can be the same or different;
• wherein Z1, Z2, Z3 or Z4 of formula (IIA) is a monovalent group selected from the group consisting of R, R′, R1;
• an alkylarylalkyl containing from 8 to 22 carbon atoms;
• an aryl ether containing from 6 to 22 carbon atoms;
• a cycloalkyl containing from 6 to 22 carbon atoms;
• a cycloalkylalkylene containing from 7 to 22 carbon atoms;
• a bicycloalkyl containing from 7 to 22 carbon atoms;
• cyclothioalkyl containing from 6 to 12 carbon atoms;
• an aryl containing 5 to 12 carbon atoms and a hetero atom selected from the group consisting of —N, —O, and —S;
• an alkyl aldehyde containing from 1 to 20 carbon atoms;
• and an alkylaryl aldehyde containing from 7 to 20 carbon atoms, each of which groups can optionally be substituted by an alkyl of 1 to 8 carbon atoms, OH, Cl, or Br, or a silyl ether group R13Si—O—,
• wherein R1 is a monovalent unsaturated, unsubstituted or substituted alkenyl or alkynyl group selected from the group consisting of an alkenyl containing from 2 to 22 carbon atoms, a cycloalkenyl containing from 6 to 22 carbon atoms, a bicycloalkenylalkylene containing from 7 to 22 carbon atoms, an acrylate group, a methacrylate group, an alkynyl containing from 2 to 22 carbon atoms, and oxiranyl and carbonate derivatives of the respective R1 groups, and oxiranyl groups containing 3 to 22 carbon atoms, carbonate groups containing from 4 to 23 carbon atoms, Cl, Br, I, —SH, —S—R, —OH, —O—R, —CN, —NCO, and blocked —NCO, (X)x(Y)3-xSi—, R6xR′3-xSi—, a polyether group, carboxy (—COOH), diacids, diesters, polyester moiety, nitro-alkyl-, cyano-alkyl-, acyl- or alkyl sulfonyl fluoride- groups and, an ionic group derived from an ester of a carboxylic acid, sulphonic acid or phosphonic acid, phosphines, an amino group, a primary amine, a secondary amine, a tertiary amine, a keto group, and betaines,
• and wherein R is as defined above, and the subscript x is an integer of from 1 to 3, X and Y are each selected from the group consisting of OH, OR′, —N(R′)2, R′ O(O)—O—, and R′, wherein R′ is as defined above, and X and Y can be same or different, and wherein each R6 is an aryl containing from 6 to 10 carbon atoms, an arylalkyl containing from 7 to 12 carbon atoms, a cycloalkyl containing from 6 to 12 carbon atoms, a bicycloalkyl containing from 7 to 16 carbon atoms, an epoxy alkyl containing from 3 to 12 carbon atoms, an epoxy cycloalkyl containing from 6 to 12 carbon atoms, an epoxy bicycloalkyl containing from 7 to 16 carbon atoms, thiocycloalkyl containing from 6 to 12 carbon atoms, and an aryl containing from 5 to 12 carbon atoms, wherein the aryl, arylalkyl, or cycloalkyl contains hetero substitutions of one or more of a —N, —O, and —S— atom;
• and wherein Z1, Z2, Z3 and Z4 can be same or different;
• and
• wherein each L1, L2, L3 and L4 is selected from the group consisting of a single bond, a divalent alkylene group having at least two carbon atoms, and a trivalent group;
• optionally the two carbon atoms of the divalent alkylene group is interrupted by one or more of —O—, —NR3—C(O)—, —NR3—, —OC(O)NR3—, and/or —NR3—C(O)—NR3— moieties bonded via carbon bond of L1 or L2 to the silicon atom of the respective siloxy unit of the polyorganosiloxane (I) and wherein R3 is hydrogen, Me3Si— or an alkyl containing from 1 to 8 carbon atoms, optionally the divalent alkylene group is substituted by one or more OH groups,
• and wherein L1, L2, L3 and L4 can be same or different.