# US 9,005,361 B2 · Defoamer compositions for building-product mixtures

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- Number: US 9,005,361 B2
- Document ID: US9005361B2
- Status: Granted
- Kind: B2
- Application number: 13/719,791
- Filed: 2012-12-19
- Published: 2013-07-11
- Granted: 2015-04-14
- Earliest claimed: 2011-12-22
- Assignees: Evonik Industries AG
- Applicants: Frauke Henning; Anke Reinschmidt; Ralph Scheuermann; George-Hans Bayne; Kerstin Klein; Markus Roos
- Inventors: Frauke Henning; Anke Reinschmidt; Ralph Scheuermann; George-Hans Bayne; Kerstin Klein; Markus Roos
- Web page: https://patentgrep.com/patent/US9005361B2

## CPC

- C04B 24/42: Organo-silicon compounds
- C04B 28/02: containing hydraulic cements other than calcium sulfates
- C04B 28/14: containing calcium sulfate cements {(gypsum-paper plates E04C)}
- C04B 40/0039: {Premixtures of ingredients}
- C07F 7/0896: {Compounds with a Si-H linkage}
- C08L 83/12: containing polyether sequences
- C04B 2103/50: Defoamers, air detrainers
- C08G 77/46: containing polyether sequences
- C04B: LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE {(roofing granules E04D7/005)}; CERAMICS (devitrified glass-ceramics C03C10/00); REFRACTORIES; TREATMENT OF NATURAL STONE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present application relates to compositions comprising at least one siloxane and at least one superplasticizer based on polycarboxylate ethers or sulphonates of lignin, melamine or naphthalene or of resins thereof, and to the use of such compositions as or in building-product mixtures or building products, especially mortar mixtures or concrete mixtures. Preferably the siloxane is a branched siloxane containing at least one “T” unit and containing at least two different polyoxyalkylene moieties.

## Claims

### Claim 1

Composition comprising at least one siloxane of the formula (I)
Ma1MAa2MBa3MCa4Db1DAb2DBb3DCb4Tc1TAc2TBc3TCc4Qd1 (Formula I)
where
a1=0 to 32,
a2=0 to 10,
a3=0 to 32,
a4=0 to 10,
b1=1 to 600,
b2=0 to 10,
b3=0 to 80,
b4=0 to 20,
c1=0 to 30,
c2=0 to 10,
c3=0 to 10,
c4=0 to 10,
d1=0 to 15,
with the proviso that
a1+a2+a3+a4>3, and;
a3+b3+c3≧1, and;
c1+c2+c3+c4>1,
M=[R13SiO1/2]
MA=[R2R12SiO1/2]
MB=[R3R12SiO1/2]
MC=[R4R12SiO1/2]
D=[R12SiO2/2]
DA=[R21R11SiO2/2]
DB=[R31R11SiO2/2]
DC=[R41R11SiO2/2]
T=[R1SiO3/2]
TA=[R2SiO3/2]
TB=[R3SiO3/2]
TC=[R4SiO3/2]
Q=[SiO4/2],
R1 independently represents at least one radical from the group of linear, cyclic or branched, aliphatic or aromatic, saturated or unsaturated hydrocarbon radicals having 1 up to 20 carbon atoms,
R2 independently represents a hydrogen, alkoxy, carboxy, hydroxyl or sulphonic ester radical,
R3 independently represents alike or unalike radicals from the group comprising
—CH2—CH2—CH2—O—(CH2—CH2O—)x—(CH2—C(R′)2O—)y—(SO)z—R″
—CH2—CH2—O—(CH2—CH2O—)x—(CH2—C(R′)2O—)y—R″
where
x=0 to 100,
y=0 to 100,
z=0 to 100,
with the proviso that x may be alike or unalike y,
R′ in each occurrence is the same or different and independently represents hydrogen and/or a saturated, unsaturated or aromatic hydrocarbon radical having 1 to 12 carbon atoms, optionally substituted with heteroatoms, with alkyl or aryl radicals, with haloalkyl, haloaryl radicals, wherein the heteroatoms are selected from the group consisting of O, N and/or S,
R″ represents a hydrogen radical or an alkyl group of 1 to 4 carbon atoms, a group —C(O)—R′″ where R′″=alkyl radical, a group —CH2—O—R′, an alkylaryl group, e.g. a benzyl group, the group —C(O)NH—R′ or —C(O)0—R′,
SO represents a styrene oxide radical —CH(C6H5)—CH2—O—,
R4 independently represents alike or unalike radicals from the group of heteroatom-substituted linear, branched or cyclic, saturated, unsaturated or aromatic, optionally heteroatom-interrupted hydrocarbon radicals,
and at least one superplasticizer based on polycarboxylate ethers or sulphonates of lignin, melamine or naphthalene or of resins thereof,
wherein said at least one siloxane comprises at least two different polyalkoxylene moieties,
wherein a 6.25 wt. % of said at least one siloxane of the formula (I) in water is clear at room temperature.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein
R4 is selected from the group hydroxyalkyl, hydroxyaryl, aminoalkyl, aminoaryl, carboxyalkyl, carboxyaryl, epoxyalkyl, epoxyaryl, chloroalkyl, chloroaryl, fluoroalkyl, cyanoalkyl, alkoxysilylalkyl, acryloyloxyaryl, acryloyloxyalkyl, methacryloyloxyalkyl, methacryloyloxypropyl or vinyl radicals or radicals having quaternary nitrogen groups and also the radicals
where
R5=R1 and/or hydrogen.

### Claim 3 (depends on 2)

The composition according to claim 2, wherein R4 are radicals having quaternary nitrogen groups and said radicals having quaternary nitrogen groups are selected from the group
where
R6, R7, R8=each independently represent hydrogen or alkyl radicals having 1 to 30 carbon atoms or radicals of the formula
R9 represents identical or different radicals from the group —O—; —NR12—;
R10 represents identical or different optionally branched divalent hydrocarbon radicals;
R11 represents identical or different alkyl, aryl or alkaryl radicals of 1 to 30 carbon atoms, which optionally contain ether functions;
R12 represents identical or different radicals from the group hydrogen or alkyl of 1 to 6 carbon atoms;
where
n=2 to 18,
o=0 to 30,
p=0 to 30,
with the proviso that o may be alike or unalike p,
and
A−=identical or different counter-ions to the positive charges on the quaternized nitrogen groups, selected from organic or inorganic anions of the acids HA, and also derivatives thereof.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein a mass fraction of siloxanes of formula (I) based on a total mass fractions of siloxanes of formula (I) and of superplasticizers is from 0.01 to 10%.

### Claim 5 (depends on 1)

The composition according to claim 1, further comprising a binder.

### Claim 6 (depends on 5)

The composition according to claim 5, wherein said composition is a building-product mixture.

### Claim 7 (depends on 6)

The composition according to claim 6, wherein said building-product mixture is at least one of a mortar mixture or a concrete mixture.

### Claim 8 (depends on 1)

A method of preparing a building-product mixture comprising adding the composition according to claim 1 to a binder.

### Claim 9 (depends on 1)

The composition according to claim 1, wherein
R3 independently represents alike or unalike radicals from the group comprising
—CH2—CH2—CH2—O—(CH2—CH2O—)x—(CH2—C(R′)2O—)y—(SO)z—R″
—CH2—CH2—O—(CH2—CH2O—)x—(CH2—C(R′)2O—)y—R″
where
x=0 to 100,
y=0 to 100,
z=0 to 100,
with the proviso that x may be alike or unalike y and at least one of the R3 radicals has x being not less than y.

### Claim 10 (depends on 1)

The composition according to claim 1, wherein R′ is substituted with at least one of a haloalky radical and haloaryl radical selected from the group consisting of para-hlorophenyl or Cl—CH2— radicals.

### Claim 11 (depends on 1)

The composition according to claim 1, wherein R′ is a hydrocarbon radial selected from the group consisting of a CH2═CH—CH2—O—CH2— radical and a methyl group.

### Claim 12 (depends on 3)

The composition according to claim 3, wherein R10 represents ethylene or propylene.

### Claim 13 (depends on 3)

The composition according to claim 3, wherein R13 represents methyl, ethyl or phenyl, especially methyl.

### Claim 14 (depends on 3)

The composition according to claim 3, wherein R13 represents methyl.

### Claim 15 (depends on 3)

The composition according to claim 3, wherein o is not less than p.

### Claim 16 (depends on 5)

The composition according to claim 5, wherein said binder is at least one binder selected from the group consisting of calcium sulphate and cement.

### Claim 17 (depends on 1)

The composition according to claim 1, further comprising water.

### Claim 18 (depends on 5)

The composition according to claim 5, further comprising sand.

### Claim 19

A method of defoaming a building-product mixture comprising a binder and a superplasticizer comprising adding at least one siloxane of the formula (I)
Ma1MAa2MBa3MCa4Db1DAb2DBb3DCb4Tc1TAc2TBc3TCc4Qd1 (Formula I)
where
a1=0 to 32,
a2=0 to 10,
a3=0 to 32,
a4=0 to 10,
b1=1 to 600,
b2=0 to 10,
b3=0 to 80,
b4=0 to 20,
c1=0 to 30,
c2=0 to 10,
c3=0 to 10,
c4=0 to 10,
d1=0 to 15,
with the proviso that
a1+a2+a3+a4>3, and;
a3+b3+c3≧1, and;
c1+c2+c3+c4>1,
M=[R13SiO1/2]
MA=[R2R12SiO1/2]
MB=[R3R12SiO1/2]
MC=[R4R12SiO1/2]
D=[R12SiO2/2]
DA=[R21R11SiO2/2]
DB=[R31R11SiO2/2]
DC=[R41R11SiO2/2]
T=[R1SiO3/2]
TA=[R2SiO3/2]
TB=[R3SiO3/2]
TC=[R4SiO3/2]
Q=[SiO4/2],
R1 independently represents at least one radical from the group of linear, cyclic or branched, aliphatic or aromatic, saturated or unsaturated hydrocarbon radicals having 1 up to 20 carbon atoms,
R2 independently represents a hydrogen, alkoxy, carboxy, hydroxyl or sulphonic ester radical,
R3 independently represents alike or unalike radicals from the group comprising
—CH2—CH2—CH2—O—(CH2—CH2O—)x—(CH2—C(R′)2O—)y—(SO)z—R″
—CH2—CH2—O—(CH2—CH2O—)x—(CH2—C(R′)2O—)y—R″
where
x=0 to 100,
y=0 to 100,
z=0 to 100,
with the proviso that x may be alike or unalike y,
R′ in each occurrence is the same or different and independently represents hydrogen and/or a saturated, unsaturated or aromatic hydrocarbon radical having 1 to 12 carbon atoms, optionally substituted with heteroatoms, with alkyl or aryl radicals, with haloalkyl, haloaryl radicals, wherein the heteroatoms are selected from the group consisting of O, N and/or S,
R″ represents a hydrogen radical or an alkyl group of 1 to 4 carbon atoms, a group —C(O)—R′″ where R′″=alkyl radical, a group —CH2—O—R′, an alkylaryl group, e.g. a benzyl group, the group —C(O)NH—R′ or —C(O)0—R′,
SO represents a styrene oxide radical —CH(C6H5)—CH2—O—,
R4 independently represents alike or unalike radicals from the group of heteroatom-substituted linear, branched or cyclic, saturated, unsaturated or aromatic, optionally heteroatom-interrupted hydrocarbon radicals,
and at least one superplasticizer based on polycarboxylate ethers or sulphonates of lignin, melamine or naphthalene or of resins thereof,
wherein said at least one siloxane comprises at least two different polyalkoxylene moieties,
wherein a 6.25 wt. % of said at least one siloxane of the formula (I) in water is clear at room temperature.

### Claim 20 (depends on 1)

The composition according to claim 1, wherein a 30 wt. % of said at least one siloxane of the formula (I) in water is clear at room temperature.