Carbamates for the modification of rheological properties
Carbamates obtainable by reacting a) at least one isocyanate of the general formula (II) and/or (IIa) (OCN—R 1 —NCO) (II) (R 4 —NCO) (IIa) b) at least one hydroxyl compound of the general formula (III) and/or (IIIa) and/or (IIIb) (R 2 —(R 3 O) n —OH) (III) HO—CH 2 —(CH—OH) m —CH 2 —OH (IIIa) R—O—[Z] b (IIIb) are described as well as their use for the modification of Theological properties of homogeneous-phase systems or hetergeneous-phase systems which contain at least one hydrophobic component.
1 . A carbamate obtainable by reacting
a) at least one isocyanate of the general formula (II), (IIa), or a combination thereof
(OCN—R 1 —NCO) (II)
(R 4 —NCO) (IIa)
in which
R 1 , R 4 independently of one another is an aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, an aromatic hydrocarbon radical or a mixture thereof, with
b) at least one hydroxyl compound of the general formula (III), (IIIa), (IIIb), or a combination thereof
(R 2 —(R 3 O) n —OH) (III)
HO—CH 2 —(CH—OH) m —CH 2 —OH (IIIa)
R—O—[Z] b (IIIb)
in which
R 2 is a branched or straight-chain C 8 -C 50 -alkyl, a branched or straight-chain C 8 -C 50 -alkenyl radical, or a C 6 -C 20 -aryl branched or straight-chain alkyl or alkenyl radical,
R 3 is C a H 2a where a=2 to 12,
R is an alkyl or alkenyl radical having 6 to 22 C atoms or H,
Z is a sugar radical having 5 or 6 carbon atoms,
b is 1 to 10,
n is 0 to 200, and
m is 1 to 4.
2 . A carbamate as claimed in claim 1 , wherein a is 2.
3 . A carbamate as claimed in claim 1 , wherein n is 5 to 50.
4 . A carbamate as claimed in claim 1 , comprising compounds of the general formula (I)
R 2 —(R 3 O) n —O—C(O)−N(H)—R 1 —N(H)—C(O)—O—(OR 3 ) n —R 2 (I)
which are obtainable by reacting
a) at least one diisocyanate of the general formula (II)
(OCN—R 1 —NCO) (II)
R 1 is an aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, an aromatic hydrocarbon radical or a mixture thereof, with
b) alkyl polyethers of the general formula (III)
(R 2 —(R 3 O) n —OH) (III)
in which
R 2 is a branched or straight-chain C 8 -C 50 -alkyl, a branched or straight-chain C 8 -C 50 -alkenyl radical, or a C 6 -C 20 -aryl branched or straight-chain alkyl or alkenyl radical,
R 3 is C a H 2a where a=2 to 12.
5 . A carbamate as claimed in claim 4 , wherein a is 2.
6 . A carbamate as claimed in claim 1 , obtainable by reacting at least
a) one isocyanate of the general formula (IIa) and optionally (II)
(OCN—R 1 —NCO) (II)
R 4 —NCO) (II a)
in which
R 1 , R 4 independently of one another is an aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, an aromatic hydrocarbon radical or a mixture thereof, with
b) at least one hydroxyl compound of the general formula (IIIa), (IIIb), or a mixture thereof
HO—CH 2 —(CH—OH) m —CH 2 —OH (IIIa)
R—O—[Z] b (II)
in which
R is an alkyl or alkenyl radical having 6 to 22 C atoms or H,
Z is a sugar radical having 5 or 6 carbon atoms,
b is 1 to 10,
n is 0 to 200, and
m is 1 to 4.
7 . A carbamate as claimed in claim 1 , wherein the isocyanate according to general formula (II) additionally used is at least one compound selected from hexamethylene diisocyanate, tetra-methylene diisocyanate, isophorone diisocyanate, or dicyclohexylmethane-4,4′-diisocyanate.
8 . A carbamate as claimed in claim 1 , wherein the isocyanate according to general formula (IIa) additionally used is at least one compound in which the radical R 4 is an optionally branched alkyl radical having 6 to 22 C atoms.
9 . A carbamate as claimed in claim 4 , wherein the hydroxyl compound according to general formula (III) additionally used is at least one compound in which R 2 is a branched or straight-chain C 8 -C 22 -alkyl or alkenyl radical and R 3 is the radical —(C 2 H 4 O) n —, where n=5 to 15.
10 . A carbamate as claimed in claim 6 , wherein the hydroxyl compound according to general formula (IIIa) additionally used is at least one compound in which m=2 to 4.
11 . A carbamate as claimed in claim 6 , wherein the hydroxyl compound according to general formula (IIIb) additionally used is at least one compound in which Z is at least one sorbitol, glucose or fructose radical.
12 . A homogeneous-phase or heterogeneous-phase composition comprising at least one water-insoluble, liquid compound, and a carbamate as claimed in claim 1 for the modification of the rheological properties of the composition.
13 . A composition consisting of at least one carbamate as claimed in claim 1 and at least one water-insoluble, liquid compound selected from the group consisting of oils, fats, saturated acyclic and cyclic hydrocarbons, esters of monocarboxylic acids with mono-, di- or trihydric alcohols, silicone oils and their mixtures with one another and among one another.
14 . A cosmetic or pharmaceutical composition comprising at least one carbamate as claimed in claim 1 , at least one water-insoluble, liquid compound, at least one cosmetically or pharmaceutically active substance and optionally at least one additive.
15 . A method of preparing a carbamate comprising reacting
a) at least one isocyanate of the general formula (II), (IIa), or a combination thereof
(OCN—R 1 —NCO) (II)
(R 4 —NCO) (IIa)
in which
R 1 , R 4 independently of one another is an aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, an aromatic hydrocarbon radical or a mixture thereof, with
b) at least one hydroxyl compound of the general formula (III), (IIIa), (IIIb), or a combination thereof
(R 2 —(R 3 O) n —OH) (III)
HO—CH 2 —(CH—OH) m —CH 2 —OH (IIIa)
R—O—[Z] b (IIIb)
in which
R 2 is a branched or straight-chain C 8 -C 50 -alkyl, a branched or straight-chain C 8 -C 50 -alkenyl radical, or a C 6 -C 20 -aryl branched or straight-chain alkyl or alkenyl radical,
R 3 is C a H 2a where a=2 to 12,
R is an alkyl or alkenyl radical having 6 to 22 C atoms or H,
Z is a sugar radical having 5 or 6 carbon atoms,
b is 1 to 10,
n is 0 to 200, and
m is be 1 to 4.
16 . The method of claim 15 wherein a) is at least one diisocyanate of the general formula (II)
(OCN—R 1 —NCO) (II)
R 1 is an aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, an aromatic hydrocarbon radical or a mixture thereof, and
b) is alkyl polyethers of the general formula (III)
(R 2 —(R 3 O) n —OH) (III)
in which
R 2 is a branched or straight-chain C 8 -C 50 -alkyl, a branched or straight-chain C 8 -C 50 -alkenyl radical, or a C 6 -C 20 -aryl branched or straight-chain alkyl or alkenyl radical,
R 3 is C a H 2a where a=2 to 12.
17 . The method of claim 15 wherein a) is at least one isocyanate of the general formula (IIa) and optionally (II)
(OCN—R 1 —NCO) (II)
(R 4 —NCO) (II a)
in which
R 1 , R 4 independently of one another is an aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, an aromatic hydrocarbon radical or a mixture thereof, and
b) is at least one hydroxyl compound of the general formula (IIIa), (IIIb), or a mixture thereof
HO—CH 2 —(CH—OH) m —CH 2 —OH (IIIa)
R—O—[Z] b (IIIb)
in which
R is an alkyl or alkenyl radical having 6 to 22 C atoms or H,
Z is a sugar radical having 5 or 6 carbon atoms,
b is 1 to 10,
n is 0 to 200, and
m is 1 to 4.
18 . The method of claim 15 , wherein the isocyanate according to general formula (II) additionally used is at least one compound selected from hexamethylene diisocyanate, tetra-methylene diisocyanate, isophorone diisocyanate, or dicyclohexylmethane-4,4′-diisocyanate.
19 . The method of claim 15 , wherein the isocyanate according to general formula (IIa) additionally used is at least one compound in which the radical R 4 is an optionally branched alkyl radical having 6 to 22 C atoms.
20 . The method of claim 16 , wherein the hydroxyl compound according to general formula (III) additionally used is at least one compound in which R 2 is a branched or straight-chain C 8 -C 22 -alkyl or alkenyl radical and R 3 is the radical —(C 2 H 4 O) n —, where n=5 to 15.
21 . The method of claim 17 , wherein the hydroxyl compound according to general formula (IIIa) additionally used is at least one compound in which m=2 to 4.
22 . The method of claim 17 , wherein the hydroxyl compound according to general formula (IIIb) additionally used is at least one compound in which Z is at least one sorbitol, glucose or fructose radical.