# US 8,569,385 B2 · Hydrolysis resistant organomodified silylated ionic surfactants

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- Number: US 8,569,385 B2
- Document ID: US8569385B2
- Status: Granted
- Kind: B2
- Application number: 12/955,276
- Filed: 2010-11-29
- Published: 2011-05-05
- Granted: 2013-10-29
- Earliest claimed: 2006-12-11
- Assignees: Momentive Performance Materials Inc.
- Applicants: Mark D. Leatherman; George A. Policello; Wenqing N. Peng; Liping Zeng; Ronald Wagner; Suresh K. Rajamaran; Zijun Xia
- Inventors: Mark D. Leatherman; George A. Policello; Wenqing N. Peng; Liping Zeng; Ronald Wagner; Suresh K. Rajamaran; Zijun Xia
- Web page: https://patentgrep.com/patent/US8569385B2

## CPC

- A01N 25/30: characterised by the surfactants
- A61K 8/585: {Organosilicon compounds}
- A61Q 19/00: Preparations for care of the skin
- C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
- C10G 33/04: with chemical means
- C11D 3/162: {containing Si}
- D21C 3/28: Prevention of foam
- D21H 21/12: Defoamers
- D21H 17/59: obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon
- D21H 19/32: obtained by reactions forming a linkage containing silicon in the main chain of the macromolecule
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- D21C: PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21H: PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR

## Abstract

The present invention provides for a composition comprising a silane having the formula: (R1)(R2)(R3)Si—R4—Si(R5)(R6)(R7) wherein R1, R2, R3, R5, and R6 are each independently selected from the group consisting of 1 to 6 monovalent hydrocarbon radicals, aryl, and a hydrocarbon group of 7 to 10 carbons containing an aryl group; R4 is a hydrocarbon group of 1 to 3 carbons; R7 comprises an anionic, cationic or zwitterionic substituent. The silanes of the present invention exhibit resistance to hydrolysis over a wide pH range.

## Claims

### Claim 1

An aqueous emulsion composition comprising a discontinuous phase and a continuous phase wherein said discontinuous phase comprises water and said continuous phase a silane having the formula:
(R1)(R2)(R3)Si—R4—Si(R5)(R6)(R7)
wherein
R1, R2, R3, R5, and R6 are each methyl;
R4 is a hydrocarbon group of 1 to 3 carbons;
R7 is selected from the group consisting of R9—RC, and R10—RZ;
R9 is a monovalent radical selected from the group consisting of
R16(O)w(R17)x—, and R18O(C2H4O)d(C3H8O)e(C4H8O)fCH2CH(OH)CH2;
where R16 and R17 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms; R18 is a divalent hydrocarbon group of 2 to 4 carbon atoms; subscripts w and x are 1;
the subscripts d, e and f are zero or positive and satisfy the following relationships:
1≦d+e+f≦10 with d≧1;
Rc is selected from the group consisting of N(R19)(R20),
where R19 and R20 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, R26N(R29)(R30), and —R27O(C7H4O)g(C3H6O)h(C4H8O)iR28;
the subscripts g, h and i are zero or positive and satisfy the following relationships:
1≦g+h+i≦10 with g≧1;
R21, R23, R24, R25 are each independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;
R22 is a monovalent radical selected from the group consisting of H, branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and —R31O(C2H4O)jC3H6O)k(C4H8O)lR32;
the subscripts j, k and l are zero or positive and satisfy the following relationships:
1≦j+k+l≦10 with j≧1;
R26 is a divalent hydrocarbon radical of 1 to 6 carbons, or
R33O(C7H4O)m(C3H6O)n(C4H8O)oR34;
the subscripts m, n and o are zero or positive and satisfy the following relationships:
1≦m+n+o≦10 with m≧1;
R29 and R30 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, and linear monovalent hydrocarbon radical of 1 to 4 carbons;
R27, R31 and R33 are independently selected from the group consisting of a divalent hydrocarbon group of 2 to 4 carbon atoms;
R28 is a monovalent radical selected from the group consisting of H, a monovalent hydrocarbon radical of 1 to 6 carbons and N(R40)(R41);
R32 and R34 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and R37N(R38)(R39); where R37 is a divalent hydrocarbon radical of 1 to 6 carbons;
R35, R36, R38 and R39 are independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;
R10 is a monovalent radical selected from the group consisting of R40(O)y(R41)z— and R42O(C2H4O)p(C3H6O)q(C4H8O)rCH2CH(OH)CH2—; where R40 and R41 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms;
R42 is a divalent hydrocarbon group of 2 to 4 carbon atoms;
the subscripts y and z are 1;
the subscripts p, q and r are zero or positive and satisfy the following relationships:
1≦p+q+r≦10 with p≧1;
RZ is —N—(R43)(R44)αR45SO3(MK)β-, —N—(R46)(R47)γR48COO(MK)δ, —N+—(R49)(R50)R51OP(═O)(A)(B) or, (—C(═O)N(R52)R53N—(R54)(R55))+-(R56OP(═O)(A)(B))(X)ε; where R43, R44, R46, R47, R49, R50, R52, R54 and R55 are independently selected from the group consisting of H, a branched monovalent hydrocarbon radical of 1 to 4 carbons, linear monovalent hydrocarbon radical of 1 to 4 carbons, and an alkanolamine group having alkyl groups of 2 to 4 carbons; R45 is a divalent group of 3 to 4 carbons;
MK is a cation selected from the group consisting of Na+, K+, Ca2+, NH4+Li+ monovalent ammonium ions derived from mono-, di- and trialkylamines comprising alkyl groups of 2 to 4 carbons and mono-, di- and trialkanolamines comprising alkyl groups of 2 to 4 carbons;
subscripts α, β, γ and δ are zero or 1 subject to the following relationships: α+β=1 and γ+δ=1;
R48 and R51 are independently a divalent group of 1 to 4 carbons;
R53 and R56 are each independently a divalent group of 2 to 4 carbons;
A and B are selected from O− and OMK; X is an anion selected from the group consisting of Cl, Br, and I; and the subscript ε is 0, 1 or 2.

### Claim 2 (depends on 1)

The composition of claim 1 where R7 is R9—Rc.

### Claim 3 (depends on 1)

The composition of claim 1 where RCC is N(R19)(R20).

### Claim 4 (depends on 1)

The composition of claim 1 where R7 is R10-RZ.

### Claim 5 (depends on 1)

The composition of claim 1 where RZ is —N—(R43)(R44)αR45SO3(MK)δ.

### Claim 6 (depends on 1)

The composition of claim 1 where RZ is —N—(R46)(R47)γR48COO(MK)δ.

### Claim 7

A non-aqueous emulsion comprising a discontinuous phase and a continuous phase wherein said discontinuous phase comprises a non-aqueous hydroxylic solvent and said continuous phase a silane having the formula:
(R1)(R2)(R3)S1—R4—Si(R5)(R6)(R7)
wherein
R1, R2, R3, R5, and R6 are each methyl;
R4 is a hydrocarbon group of 1 to 3 carbons;
R7 is selected from the group consisting of R9—RC and R10—RZ;
R9 is a monovalent radical selected from the group consisting of
R16(O)w(R17)x— and R18O(C2H4O)d(C3H6O)e(C6H8O)fCH2CH(OH)CH2;
where R16 and R17 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms; R18 is a divalent hydrocarbon group of 2 to 4 carbon atoms; subscripts w and x are 1;
the subscripts d, e and f are zero or positive and satisfy the following relationships:
1≦d+e+f≦10 with d≧1;
RC is selected from the group consisting of N(R19)(R20),
where R19 and R20 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, R26N(R29)(R30), and —R27O(C2H4O)g(C3H6O)h(C4H8O)iR28;
the subscripts g, h and i are zero or positive and satisfy the following relationships:
1≦g+h+i≦10 with g≧1;
R21, R23, R24, R25 are each independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;
R22 is a monovalent radical selected from the group consisting of H, branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and —R31O(C2H4O)i(C3H6O)k(C4H8O)lR32;
the subscripts j, k and l are zero or positive and satisfy the following relationships:
1≦j+k+l≦10 with j≧1;
R26 is a divalent hydrocarbon radical of 1 to 6 carbons, or
R33O(C2H4O)m(C3H6O)n(C4H8O)oR34;
the subscripts m, n and o are zero or positive and satisfy the following relationships:
1≦m+n+o≦10 with m≧1;
R29 and R30 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, and linear monovalent hydrocarbon radical of 1 to 4 carbons;
R27, R31 and R33 are independently selected from the group consisting of a divalent hydrocarbon group of 2 to 4 carbon atoms;
R28 is a monovalent radical selected from the group consisting of H, a monovalent hydrocarbon radical of 1 to 6 carbons and N(R40)(R41);
R32 and R34 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and R37N(R38)(R39); where R37 is a divalent hydrocarbon radical of 1 to 6 carbons;
R35, R36, R38 and R39 are independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;
R10 is a monovalent radical selected from the group consisting of
R40(O)y(R41)z— and R42O(C2H4O)p(C3H6O)q(C4H8O)rCH2CH(OH)CH2—;
where R40 and R41 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms;
R42 is a divalent hydrocarbon group of 2 to 4 carbon atoms;
the subscripts y and z are 1;
the subscripts p, q and r are zero or positive and satisfy the following relationships:
1≦p+q+r≦10 with p≧1;
RZ is —N—(R43)(R44)αR45SO3(MK)β, —N—(R46)(R47)γR48COO(MK)δ,
—N+—(R49)(R50)R51OP(═O)(A)(B) or,
(—C(═O)N(R52)R53N—(R54)(R55))+-(R56OP(═O)(A)(B))(X−)ε;
where R43, R44, R46, R47, R49, R50, R52, R54 and R55 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, linear monovalent hydrocarbon radical of 1 to 4 carbons and an alkanolamine group having alkyl groups of 2 to 4 carbons; and R45 is a divalent group of 3 to 4 carbons;
MK is a cation selected from the group consisting of Na+,K+, Ca2+, NH4+, and Li+, monovalent ammonium ions derived from mono-, di- and trialkylamines comprising alkyl groups of 2 to 4 carbons, and mono-, di- and trialkanolamines comprising alkyl groups of 2 to 4 carbons;
subscripts α, β, γ and δ are zero or 1 subject to the following relationships:
α+β=1 and γ+δ=1;
R48 and R51 are independently a divalent group of 1 to 4 carbons;
R53 and R56 are each independently a divalent group of 2 to 4 carbons;
A and B are selected from O− and OMK; X is an anion selected from the group consisting of Cl, Br, and I; and the subscript ε is 0, 1 or 2.

### Claim 8 (depends on 7)

The non-aqueous emulsion of claim 7 where R7 is R9—RC.

### Claim 9 (depends on 7)

The non-aqueous emulsion of claim 7 where RC is N(R19)(R20).

### Claim 10 (depends on 7)

The non-aqueous emulsion of claim 7 where R7 is R10—RZ.

### Claim 11 (depends on 7)

The non-aqueous emulsion of claim 7 where RZ is —N—(R43)(R44)c,R45SO3(MK)β.

### Claim 12 (depends on 7)

The non-aqueous emulsion of claim 7 where RZ is —N—(R46)(R47)γR48COO(MK)δ.

### Claim 13

A non-aqueous emulsion comprising a continuous phase and a discontinuous phase wherein said continuous phase comprises a non-aqueous hydroxylic organic solvent and said discontinuous phase comprises a silane having the formula:
(R1)(R2)(R3)Si—R4—Si(R5)(R6)(R7)
wherein
R1, R2, R3, R5, and R6 are each methyl;
R4 is a hydrocarbon group of 1 to 3 carbons;
R7 is selected from the group consisting of R9—RC and R10—RZ;
R9 is a monovalent radical selected from the group consisting of
R16(O)w(R17)x— and R18O(C2H4O)d(C3H6O)e(C6H8O)fCH2CH(OH)CH2;
where R16 and R17 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms; R18 is a divalent hydrocarbon group of 2 to 4 carbon atoms; subscripts w and x are 1;
the subscripts d, e and f are zero or positive and satisfy the following relationships:
1≦d+e+f≦10 with d≧1;
RC is selected from the group consisting of N(R19)(R20),
where R19 and R20 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, R26N(R29)(R30), and —R27O(C2H4O)g(C3H6O)h(C4H8O)iR28;
the subscripts g, h and i are zero or positive and satisfy the following relationships:
1≦g+h+i≦10 with g≧1;
R21, R23, R24, R25 are each independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;
R22 is a monovalent radical selected from the group consisting of H, branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and —R31O(C2H4O)j(C3H6O)k(C4H8O)lR32;
the subscripts j, k and 1 are zero or positive and satisfy the following relationships:
1≦j+k+l≦10 with j≧1;
R26 is a divalent hydrocarbon radical of 1 to 6 carbons, or
R33O(C2H4O)m(C3H6O)n(C4H8O)oR34;
the subscripts m, n and o are zero or positive and satisfy the following relationships:
1≦m+n+o≦10 with m≧1;
R29 and R30 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, and linear monovalent hydrocarbon radical of 1 to 4 carbons;
R27, R31 and R33 are independently selected from the group consisting of a divalent hydrocarbon group of 2 to 4 carbon atoms;
R28 is a monovalent radical selected from the group consisting of H, a monovalent hydrocarbon radical of 1 to 6 carbons and N(R40)(R41);
R32 and R34 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and R37N(R38)(R39); where R37 is a divalent hydrocarbon radical of 1 to 6 carbons;
R35, R36, R38 and R39 are independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;
R10 is a monovalent radical selected from the group consisting of
R40(O)y(R41)n— and R42O(C2H4O)p(C3H6O)q(C4H8O)rCH2CH(OH)CH2—;
where R40 and R41 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms;
R42 is a divalent hydrocarbon group of 2 to 4 carbon atoms;
the subscripts y and z are 1;
the subscripts p, q and r are zero or positive and satisfy the following relationships:
1≦p+q+r≦10 with p≧1;
RZ is —N—(R43)(R44)αR45SO3(MK)β, —N—(R46)(R47)γR48COO(MK)δ,
—N+—(R49)(R50)R51OP(═O)(A)(B) or,
(—C(═O)N(R52)R53N—(R54)(R55))+—(R56OP(═O)(A)(B))(X)ε;
where R43, R44, R46, R47, R49, R50, R52, R54 and R55 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, linear monovalent hydrocarbon radical of 1 to 4 carbons and an alkanolamine group having alkyl groups of 2 to 4 carbons; and R45 is a divalent group of 3 to 4 carbons;
MK is a cation selected from the group consisting of Na+,K+, Ca2+, NH4+, and Li+, monovalent ammonium ions derived from mono-, di- and trialkylamines comprising alkyl groups of 2 to 4 carbons, and mono-, di- and trialkanolamines comprising alkyl groups of 2 to 4 carbons;
subscripts α, β, γ and δ are zero or 1 subject to the following relationships:
α+β=1 and γ+δ=1;
R48 and R51 are independently a divalent group of 1 to 4 carbons;
R53 and R56 are each independently a divalent group of 2 to 4 carbons;
A and B are selected from O− and OMK; X is an anion selected from the group consisting of Cl, Br, and I; and the subscript ε is 0, 1 or 2.

### Claim 14 (depends on 13)

The non-aqueous emulsion of claim 13 where R7 is R9—RC.

### Claim 15 (depends on 13)

The non-aqueous emulsion of claim 13 where RC is N(R19)(R20).

### Claim 16 (depends on 13)

The non-aqueous emulsion of claim 13 where R7 is R10—RZ.

### Claim 17 (depends on 13)

The non-aqueous emulsion of claim 13 where RZ is —N—(R43)(R44)αR45 SO3(MK)β.

### Claim 18 (depends on 13)

The non-aqueous emulsion of claim 13 where RZ is —N—(R46)(R47)γR48COO(MK)δ.