# US 7,745,501 B2 · Method for demulsifying

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- Number: US 7,745,501 B2
- Document ID: US7745501B2
- Status: Granted
- Kind: B2
- Application number: 11/472,727
- Filed: 2006-06-22
- Published: 2007-12-27
- Granted: 2010-06-29
- Earliest claimed: 2006-06-22
- Assignees: Momentive Performance Materials Inc.
- Inventors: Kalman Koczo; Sabine Isabelle Azouani; Benjamin Falk
- Web page: https://patentgrep.com/patent/US7745501B2

## CPC

- B01D 17/047: {with separation aids}
- C08G 77/46: containing polyether sequences
- C10G 33/04: with chemical means
- C10L 1/285: {macromolecular compounds}
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS

## Abstract

The invention relates to a method for separating emulsions of oil and water, the method comprising incorporating a demulsifying-effective amount of a silicone demulsifier into an emulsion comprising an oil phase and an aqueous phase, the silicone demulsifier having a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened by reaction with a chemical or group capable of ring-opening an oxirane or oxetane ring, respectively, and wherein a solid filler is substantially excluded from the silicone demulsifier and emulsion. The invention also relates to compositions containing the above-described demulsifier and the water and oil phases of an emulsion.

## Claims

### Claim 1

A composition comprising:
a) a demulsifying-effective amount of a silicone demulsifier having a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a chemical or group capable of ring-opening an oxirane or oxetane ring, respectively, except that an oxetane ring is not ring-opened with water;
b) an aqueous phase; and
c) an oil phase;
wherein a solid filler is substantially excluded from the composition.

### Claim 2 (depends on 1)

The composition of claim 1, further comprising one or more organic demulsifiers selected from hydrocarbon group-containing sulfonic acids, carboxylic acids, thiocarboxylic acids, carboxylic acid esters, phosphinic acids, sulfates, and phosphates; alkyleneoxide polymers or copolymers and their esters; alkyleneoxide-functionalized phenolic resins; epoxy resins; amine alkyleneoxides; polyimine alkoxylates; polyester amines; cationic surfactants; bis-amides; silicone-based polymers or copolymers lacking one of an ethylene oxide component, a propylene oxide component, or an epoxide-containing group; and salts thereof.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the one or more alkylene oxide groups are independently according to the formula —Xz—(OCHRCH2)sOR7 wherein X is an optional linking group with z independently 0 or 1, R is independently selected for each alkylene oxide unit from hydrogen or a hydrocarbon group having one to three carbon atoms, R7 is independently selected from the group consisting of hydrogen or a hydrocarbon group having one to twenty carbon atoms, and s is 1 or a higher integer.

### Claim 4 (depends on 3)

The composition of claim 3, wherein R is independently selected for each alkylene oxide unit from either hydrogen or methyl.

### Claim 5 (depends on 4)

The composition of claim 4, wherein at least one alkylene oxide group is an ethylene oxide-propylene oxide copolymer.

### Claim 6 (depends on 3)

The composition of claim 3, wherein s is 10 or a higher integer.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the silicone demulsifier has a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxirane-containing groups.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the silicone demulsifier has a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxirane-containing groups ring-opened without polymerization by reaction with a chemical or group capable of opening an oxirane ring.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the silicone demulsifier has a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxetane-containing groups.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the silicone demulsifier has a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more unpolymerized alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxetane-containing groups ring-opened without polymerization by reaction with a chemical or group capable of opening an oxetane ring, except that the oxetane ring is not ring-opened with water.

### Claim 11 (depends on 1)

The composition of claim 1, wherein the silicone demulsifier is according to the formula:
M1aM2bM3cD1dD2eD3fT1gT2hT3iQj (1)
wherein:
M1=R13SiO1/2;
M2=R1kR2(3−k)SiO1/2; k=0, 1 or 2
M3=R11R3(3−l)SiO1/2; l=0, 1 or 2
D1=R12SiO2/2;
D2=R1mR2(2−m)SiO2/2; m=0 or 1
D3=R1nR3(2−n)SiO2/2; n=0 or 1
T1=R1SiO3/2;
T2=R2SiO3/2;
T3=R3SiO3/2;
Q=SiO4/2
wherein R1 is independently selected from the group consisting of hydrogen, halogen, linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon groups having one to twenty carbon atoms and optionally heteroatom-substituted with one or more oxygen and/or nitrogen atoms; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6 where p is a number of 0 to 5, and q and r are each independently a number of 0 to 100, provided that the sum of q and r is at least 1; R3 is a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively, except that an oxetane ring is not ring-opened with water; each of R4 and R5 independently represents a divalent hydrocarbon radical having one to five carbon atoms; R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms; a, b, c, d, e, f , g, h, i and j are each independently 0 or a positive integer, provided that (a+b+c) equals (2+g+h+i+2j), the sum (a+b+c+d+e+f+g+h+i+j) is equal to or greater than 3, the sum (g+h+i+j) is equal to or greater than 0 and less than or equal to 10, and the sums (b+e+h) and (c+f+i) are independently a number of 1 to 200.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the sum (a+b+c+d+e+f+g+h+i+j) is equal to or greater than 3 and less than or equal to 500.

### Claim 13 (depends on 11)

The composition of claim 11, wherein the sum (a+b+c+d+e+f+g+h+i+j) is greater than 100.

### Claim 14 (depends on 11)

The composition of claim 11, wherein the silicone demulsifier is according to the formula:
M1D1dD2eD3fM1 (2)
wherein M1=R13SiO1/2; D1=R12SiO2/2; D2=R1mR2(2−m)SiO2/2, where m=0 or 1; D3=R1nR3(2−n)SiO2/2, where n=0 or 1; R1 is independently selected from the group consisting of hydrogen, halogen, linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon groups having one to twenty carbon atoms and optionally heteroatom-substituted with one or more oxygen and/or nitrogen atoms; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6, where one of R4 and R5 is represented by —CH2CH2— and another R4 and R5 by —CH2CH(CH3)— and where p is a number of 0 to 5, and q and r are each independently a number of 1 to 100; R3 is a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively; R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms; d is 0 or a higher number, and e and f are independently 1 or a higher number, such that the sum of d, e, and f is no greater than about 500.

### Claim 15 (depends on 14)

The composition of claim 14, wherein M1=(CH3)3SiO1/2; D1=(CH3)2SiO2/2; D2=(CH3)(R2)SiO2/2, D3=(CH3)(R3)SiO2/2; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6, where one of R4 and R5 is represented by —CH2CH2— and another R4 and R5 by —CH2CH(CH3)— and where p is a number of 0 to 5, and q and r are each independently a number of 1 to 100; R3 is a monovalent hydrocarbon radical having one to twenty carbon atoms and one or more oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively; and R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms.

### Claim 16

A composition comprising:
(a) a demulsifying-effective amount of silicone demulsifier having the formula
M1D1dD2eD3fM1 (2)
wherein M1=R13SiO1/2; D1=R12SiO2/2; D2=R1mR2(2−m)SiO2/2, where m=0 or 1; D3=R1nR3(2−n)SiO2/2, where n=0 or 1; R1 is independently selected from the group consisting of hydrogen, halogen, linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon groups having one to twenty carbon atoms and optionally heteroatom-substituted with one or more oxygen and/or nitrogen atoms; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6, where one of R4 and R5 is represented by —CH2CH2— and another R4 and R5 by —CH2CH(CH3)— and where p is a number of 0 to 5, and q and r are each independently a number of 1 to 100; R3 is a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively, except that an oxetane ring is not ring-opened with water; R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms; d is 0 or a higher number, and e and f are independently 1 or a higher number, such that the sum of d, e, and f is no greater than about 500;
b) an aqueous phase; and
c) an oil phase
wherein a solid filler is substantially excluded from the composition.

### Claim 17

A composition comprising:
(a) a demulsifying-effective amount of silicone demulsifier having the formula
M1aM2bM3cD1dD2eD3fT1gT2hT3iQj (1)
wherein:
M1=R13SiO1/2;
M2=R1kR2(3−k)SiO1/2; k=0, 1 or 2
M3=R1lR3(3−l)SiO1/2; l=0, 1 or 2
D1=R12SiO2/2;
D2=R1mR2(2−m)SiO2/2; m=0 or 1
D3=R1nR3(2−n)SiO2/2; n=0 or 1
T1=R1SiO3/2;
T2=R2SiO3/2;
T3=R3SiO3/2;
Q=SiO4/2
wherein R1 is independently selected from the group consisting of hydrogen, halogen, linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon groups having one to twenty carbon atoms and optionally heteroatom-substituted with one or more oxygen and/or nitrogen atoms; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6 where p is a number of 0 to 5, and q and r are each independently a number of 0 to 100, provided that the sum of q and r is at least 1; R3 is a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively, except that an oxetane ring is not ring-opened with water; each of R4 and R5 independently represents a divalent hydrocarbon radical having one to five carbon atoms; R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms; a, b, c, d, e, f, g, h, i and j are each independently 0 or a positive integer, provided that (a+b+c) equals (2+g+h+i+2j), the sum (a+b+c+d+e+f+g+h+i+j) is greater than 100, the sum (g+h+i+j) is equal to or greater than 0 and less than or equal to 10, and the sums (b+e+h) and (c+f+i) are independently a number of 1 to 200;
b) an aqueous phase; and
c) an oil phase
wherein a solid filler is substantially excluded from the composition.

### Claim 18

A method for separating emulsions of oil and water, the method comprising incorporating a demulsifying-effective amount of a silicone demulsifier into an emulsion comprising an oil phase and an aqueous phase, the silicone demulsifier having a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a chemical or group capable of ring-opening an oxirane or oxetane ring, respectively, except that an oxetane ring is not ring-opened with water, and wherein a solid filler is substantially excluded from the silicone demulsifier and emulsion.

### Claim 19 (depends on 18)

The method of claim 18, wherein the silicone demulsifier is combined with one or more organic demulsifiers selected from hydrocarbon group-containing sulfonic acids, carboxylic acids, thiocarboxylic acids, carboxylic acid esters, phosphinic acids, sulfates, and phosphates; alkyleneoxide polymers or copolymers and their esters; alkyleneoxide-functionalized phenolic resins; epoxy resins; amine alkyleneoxides; polyimine alkoxylates; polyester amines; cationic surfactants; bis-amides; silicone-based polymers or copolymers lacking one of an ethylene oxide component, a propylene oxide component, or an epoxide-containing group; and salts thereof.

### Claim 20 (depends on 18)

The method of claim 18, wherein the one or more alkylene oxide groups are independently according to the formula —XZ—(OCHRCH2)sOR7 wherein X is an optional linking group with z independently 0 or 1, R is independently selected for each alkylene oxide unit from hydrogen or a hydrocarbon group having one to three carbon atoms, R7 is independently selected from the group consisting of hydrogen or a hydrocarbon group having one to twenty carbon atoms, and s is 1 or a higher integer.

### Claim 21 (depends on 20)

The method of claim 20, wherein R is independently selected for each alkylene oxide unit from either hydrogen or methyl.

### Claim 22 (depends on 21)

The method of claim 21, wherein at least one alkylene oxide group is an ethylene oxide-propylene oxide copolymer.

### Claim 23 (depends on 20)

The method of claim 20, wherein s is 10 or a higher integer.

### Claim 24 (depends on 18)

The method of claim 18, wherein the silicone demulsifier has a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxirane-containing groups.

### Claim 25 (depends on 18)

The method of claim 18, wherein the silicone demulsifier has a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxirane-containing groups ring-opened without polymerization by reaction with a chemical or group capable of opening an oxirane ring.

### Claim 26 (depends on 18)

The method of claim 18, wherein the silicone demulsifier has a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxetane-containing groups.

### Claim 27 (depends on 18)

The method of claim 18, wherein the silicone demulsifier has a molecular structure comprising a polysiloxane backbone of at least two siloxane units covalently bound to (i) one or more alkylene oxide groups comprising one or more alkylene oxide units independently having one to five carbon atoms, and (ii) one or more unpolymerized oxetane-containing groups ring-opened without polymerization by reaction with a chemical or group capable of opening an oxetane ring, except that the oxetane ring is not ring-opened with water.

### Claim 28 (depends on 18)

The method of claim 18, wherein the silicone demulsifier is according to the formula:
M1aM2bM3cD1dD2eD3fT1gT2hT3iQj (1)
wherein:
M1=R13SiO1/2;
M2=R1kR2(3−k)SiO1/2; k=0, 1 or 2
M3=R11R3(3−l)SiO1/2; l=0, 1 or 2
D1=R12SiO2/2;
D2=R1mR2(2−m)SiO2/2; m=0 or 1
D3=R1nR3(2−n)SiO2/2; n=0 or 1
T1=R1SiO3/2;
T2=R2SiO3/2;
T3=R3SiO3/2;
Q=SiO4/2
wherein R1 is independently selected from the group consisting of R1 is independently selected from the group consisting of hydrogen, halogen, linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon groups having one to twenty carbon atoms and optionally heteroatom-substituted with one or more oxygen and/or nitrogen atoms; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6 where p is a number of 0 to 5, and q and r are each independently a number of 0 to 100, provided that the sum of q and r is at least 1; R3 is a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring without polymerazation, respectively, except that an oxetane ring is not ring-opened with water; each of R4 and R5 independently represents a divalent hydrocarbon radical having one to five carbon atoms; R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms; a, b, c, d, e, f, g, h, i and j are each independently 0 or a positive integer, provided that (a+b+c) equals (2+g+h+i+2j), the sum (a+b+c+d+e +f+g+h+i+j) is equal to or greater than 3, the sum (g+h+i+j) is equal to or greater than 0 and less than or equal to 10, and the sums (b+e+h) and (c+f+i) are independently a number of 1 to 200.

### Claim 29 (depends on 28)

The method of claim 28, wherein the sum (a+b+c+d+e+f+g+h+i +j) is equal to or greater than 3 and less than or equal to 500.

### Claim 30 (depends on 28)

The method of claim 28, wherein the sum (a+b+c+d+e+f+g+h+i +j) is greater than 100.

### Claim 31 (depends on 28)

The method of claim 28, wherein the silicone demulsifier is according to the formula:
M1D1dD2eD3fM1 (2)
wherein M1=R13SiO1/2; D1=R12SiO2/2; D2=R1mR2(2−m)SiO2/2, where m=0 or 1; D3=R1nR3(2−n)SiO2/2 where n=0 or 1; R1 is independently selected from the group consisting of hydrogen, halogen, linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon groups having one to twenty carbon atoms and optionally heteroatom-substituted with one or more oxygen and/or nitrogen atoms; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6, where one of R4 and R5 is represented by —CH2CH2— and another R4 and R5 by —CH2CH(CH3)— and where p is a number of 0 to 5, and q and r are each independently a number of 1 to 100; R3 is a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively; R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms; d is 0 or a higher number, and e and f are independently 1 or a higher number, such that the sum of d, e, and f is no greater than about 500.

### Claim 32 (depends on 28)

The method of claim 28, wherein M1=(CH3)3SiO1/2; D1=(CH3)2SiO2/2; D2=(CH3)(R2)SiO2/2, D3 =(CH3)(R3)SiO2/2; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6, where one of R4 and R5 is represented by —CH2CH2— and another R4 and R5 by —CH2CH(CH3)— and where p is a number of 0 to 5, and q and r are each independently a number of 1 to 100; R3 is a monovalent hydrocarbon radical having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively; and R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms.

### Claim 33

A method for separating emulsions of oil and water, the method comprising incorporating a demulsifying-effective amount of a silicone demulsifier into an emulsion comprising an oil phase and an aqueous phase, the demulsifier having the formula
M1D1dD2eD3fM1 (2)
wherein M1=R13SiO1/2; D1=R12SiO2/2; D2=R1mR2(2−m)SiO2/2, where m=0 or 1; D3=R1nR3(2−n)SiO2/2 where n=0 or 1; R1 is independently selected from the group consisting of hydrogen, halogen, linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon groups having one to twenty carbon atoms and optionally heteroatom-substituted with one or more oxygen and/or nitrogen atoms; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6, where one of R4 and R5 is represented by —CH2CH2— and another R4 and R5 by —CH2CH(CH3)— and where p is a number of 0 to 5, and q and r are each independently a number of 1 to 100; R3 is a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively, except that an oxetane ring is not ring-opened with water; R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms; d is 0 or a higher number, and e and f are independently 1 or a higher number, such that the sum of d, e, and f is no greater than about 500, and wherein a solid filler is substantially excluded from the silicone demulsifier and emulsion.

### Claim 34

A method for separating emulsions of oil and water, the method comprising incorporating a demulsifying-effective amount of a silicone demulsifier into an emulsion comprising an oil phase and an aqueous phase, the demulsifier having the formula
M1aM2bM3cD1dD2eD3fT1gT2hT3iQj (1)
wherein:
M1=R13SiO1/2;
M2=R1kR2(3−k)SiO1/2; k=0, 1 or 2
M3=R11R3(3−l)SiO1/2; l=0, 1 or 2
D1=R12SiO2/2;
D2=R1mR2(2−m)SiO2/2; m=0 or 1
D3=R1nR3(2−n)SiO2/2; n=0 or 1
T1=R1SiO3/2;
T2=R2SiO3/2;
T3=R3SiO3/2;
Q=SiO4/2
wherein R1 is independently selected from the group consisting of hydrogen, halogen, linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon groups having one to twenty carbon atoms and optionally heteroatom-substituted with one or more oxygen and/or nitrogen atoms; R2 is according to the formula —(CH2)p(OR4)q(OR5)rOR6 where p is a number of 0 to 5, and q and r are each independently a number of 0 to 100, provided that the sum of q and r is at least 1; R3 is a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms and one or more unpolymerized oxirane-containing and/or oxetane-containing groups, wherein said oxirane or oxetane is optionally ring-opened without polymerization by reaction with a suitable chemical or group capable of ring-opening an oxirane or oxetane ring, respectively, except that an oxetane ring is not ring-opened with water; each of R4 and R5 independently represents a divalent hydrocarbon radical having one to five carbon atoms; R6 is hydrogen or a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon group having one to twenty carbon atoms; a, b, c, d, e, f, g, h, i and j are each independently 0 or a positive integer, provided that (a+b+c) equals (2+g+h+i+2j), the sum (a+b+c+d+e+f+g+h+i+j) is greater than 100, the sum (g+h+i+j) is equal to or greater than 0 and less than or equal to 10, and the sums (b+e+h) and (c+f+i) are independently a number of 1 to 200.