US 6,515,050 B1 · Comb-shaped diol, water-soluble polyurethane, and application thereof

Abstract

A water-soluble polyurethane obtained from water-soluble polyalkylene glycol, polydiisocyanate, and comb-shaped hydrophobic diol represented by the following general formula: wherein R1 is a hydrocarbon group of 1 to 20 carbon atoms; each of R2 and R3 is a hydrocarbon group or halogenated hydrocarbon group of 4 to 21 carbon atoms; each of X, X′ and X″ is an alkylene group of 2 to 10 carbon atoms; the hydrogen atoms of the above alkylene group may be substituted with an alkyl group, chlorine or an alkyl chloride group; each of Z and Z′ is oxygen, sulfur or a CH2 group; R4 is an alkylene group of 2 to 10 carbon atoms in all; k is an integer of 0 to 15; n is an integer of 0 to 15 when Z is oxygen and is 0 when Z is sulfur or a CH2 group; n′ is an integer of 0 to 15 when Z′ is oxygen and is 0 when Z′ is sulfur or a CH2 group. The water-soluble polyurethane is used as, for example, an extruding auxiliary for use in cement-based materials, a mortar thickening agent, a thickening agent for underwater concrete, a ceramics forming binder and a moisturizer for hair cosmetics, all of which are characterized by low tackiness and high shape retention.

Claims35

Dependent claims

A comb-shaped diol represented by the following general formula (1b):

wherein R1 is a hydrocarbon group of 1 to 20 carbon atoms;
each of R2 and R3 is a hydrocarbon group of 4 to 21 carbon atoms;
some or all of the hydrogen atoms of the hydrocarbon groups R1, R2 and R3 may be substituted with fluorine, chlorine, bromine or iodine;
R2 and R3 may be the same or different from each other;
each of X, X′ and X″ is an alkylene group of 2 to 10 carbon atoms;
X, X′ and X″ may be the same or different from each other;
some of the hydrogen atoms of the above alkylene group may be substituted with an alkyl group, chlorine or an alkyl chloride group;
each of Z and Z′ is oxygen, sulfur or a CH2 group;
Z and Z′ may be the same or different from each other;
R4 is an alkylene group of 2 to 10 carbon atoms in all;
n is an integer of 0 to 15 when Z is oxygen and is 0 when Z is sulfur or a CH2 group;
n′ is an integer of 0 to 15 when Z′ is oxygen and is 0 when Z′ is sulfur or a CH2 group;
and n and n′ may be the same or different from each other.

10 more elements

Water-soluble polyurethane comprising a polymer having a repeating unit (U-1) represented by the following general formula (3):

and a repeating unit (U-2) represented by the following general formula (4):
wherein A is a bivalent group derived from a water-soluble polyalkylene polyol having the general formula HO—A—OH, having hydroxyl groups at least on both terminals thereof and having a number average molecular weight of 400 to 100,000;
B is a bivalent group derived from a polyisocyanate compound selected from the group consisting of polyisocyanates represented by the general formula OCN—B—NCO and having 3 to 18 carbon atoms;
and D is a bivalent group such that the compounds having the general formula HO—D—OH are comb-shaped hydrophobic diol represented by the following general formula (1):
wherein R1 is a hydrocarbon group of 1 to 20 carbon toms;
each of R2 and R3 is a hydrocarbon group of 4 to 21 carbon atoms;
some or all of the hydrogen atoms of the hydrocarbon groups R1, R2 and R3 may be substituted with fluorine, chlorine, bromine or iodine;
R2 and R3 may be the same or different from each other;
each of X, X′ and X″ is an alkylene group of 2 to 10 carbon atoms;
X, X′ and X″ may be the same or different from each other;
some of the hydrogen atoms of the above alkylene group may be substituted with an alkyl group, chlorine or an alkyl chloride group;
each of Z and Z′ is oxygen, sulfur or a CH2 group;
Z and Z′ may be the same or different from each other;
R4 is an alkylene group of 2 to 10 carbon atoms in all;
k is an integer of 0 to 15;
n is an integer of 0 to 15 when Z is oxygen and is 0 when Z is sulfur or a CH2 group;
n′ is an integer of 0 to 15 when Z′ is oxygen and is 0 when Z′ is sulfur or a CH2 group;
and n and n′ may be the same or different from each other,
wherein the molar ratio of the repeating unit (U-1) is 0.5 or higher and 0.999 or lower, the molar ratio of the repeating unit (U-2) is 0.001 or higher and 0.5 or lower, and that the weight average molecular weight measured by the GPC is in the range of 10,000 to 10,000,000.

16 more elements

Dependencies are inferred from the claim text.

Comb-shaped diol, water-soluble polyurethane, and application thereof

Life of this patent

Comb-shaped diol, water-soluble polyurethane, and application thereof

Life of this patent

Abstract

Claims35