Addition compounds useful as dispersing agents and dispersion stabilizers, process for producing them, their use and solids coated therewith

A process for producing an addition compound or salt thereof useful as a dispersing agent or dispersion stabilizer comprising the steps of:

• (a) reacting a polyisocyanate having an average functionality of 2.5 to 10 with a monohydroxy compound of formula I
• Y--OH I
• in which Y represents
• (i) an aliphatic or cycloaliphatic hydrocarbon group having 8 to 30 carbon atoms in which hydrogen atoms may be partly replaced by halogen or aryl substituents, or
• (ii) an aliphatic, cycloaliphatic or aromatic group containing at least one --O-- or --COO-- group, having an average molecular weight M.sub.n of 200 to 10,000, and in which hydrogen atoms may be partly replaced by halogen,
• in an amount sufficient to react 10 to 70% of the isocyanate groups originally present in the isocyanate;
• (b) reacting with a compound of formula II
• G--(E).sub.n II
• in which
• E represents at least one of --OH, --NH.sub.2 and --NHR in which R is an alkyl group having 1 to 4 carbon atoms,
• n represents 2 or 3, and
• G represents an aliphatic, cycloaliphatic and/or aromatic group containing at least 2 carbon atoms, having an average molecular weight M.sub.n of not more than 3000, and which may contain at least one group selected from the group consisting of --O--, --COO--, --CONH--, --S-- and --SO.sub.2 --,
• in an amount sufficient to react 1 to 50% of the isocyanate groups originally present in the isocyanate, and to react a total of 20 to 85% of the isocyanate groups originally present in the polyisocyanate in stages (a) and (b);
• and
• (c) reacting with a compound of formula III
• Z--(CH.sub.2).sub.p --Q III
• in which
• Q represents --OH, --SH, --NH.sub.2 or --NHR in which R is an alkyl group having 1 to 4 carbon atoms,
• Z represents an aliphatic group having 2 to 10 C atoms and carrying at least one tertiary amino group or represents a heterocyclic group having at least one basic ring nitrogen atom not bonded to a hydrogen atom, and
• p is 0 when Z is an aliphatic group or an integer from 0 to 10 when Z is a heterocyclic group,
• in an amount sufficient to provide at least one molecule of formula III for each isocyanate group in the polyisocyanate unreacted after stages (a) and (b);
• wherein
• at least 1 mole % of the compound of formula I defined above is replaced by a compound of formula Ia
• Y'--OH Ia
• in which Y' represents an aliphatic, cycloaliphatic or aromatic group having an average molecular weight M.sub.n of 200 to 10,000 in which hydrogen atoms may be partly replaced by halogen and containing at least one --NHCOO-- group, or
• at least 1 mole % of the compound of formula I defined above is replaced by a monohydroxyfunctional polyacrylic or polymethacrylic acid ester or a copolymer thereof with up to 50 mole % relative to monomer units of a vinyl comonomer, having an average molecular weight M.sub.n of not more than 10,000, or
• at least 1 mole % of the compound of formula II defined above is replaced by a compound of formula IIa
• G'--(OH).sub.n IIa
• in which G' represents an aliphatic, cycloaliphatic or aromatic group containing at least 2 carbon atoms, having an average molecular weight M.sub.n of not more than 3000, and containing at least one --NHCOO-- or --Si(CH.sub.3).sub.2 O-- group, and n represents a number from 2 to 3.

Liquid dispersible pulverulent or fibrous solids coated with a dispersing agent comprising an addition compound or salt thereof obtained by

• (a) reacting a polyisocyanate having an average functionality of 2.5 to 10 with a monohydroxy compound of formula I
• Y--OH I
• in which Y represents
• (i) an aliphatic or cycloaliphatic hydrocarbon group having 8 to 30 carbon atoms in which hydrogen atoms may be partly replaced by halogen or aryl substituents, or
• (ii) an aliphatic, cycloaliphatic or aromatic group containing at least one --O-- or --COO-- group, having an average molecular weight M.sub.n of 200 to 10,000, and in which hydrogen atoms may be partly replaced by halogen,
• in an amount sufficient to react 10 to 70% of the isocyanate groups originally present in the isocyanate;
• (b) reacting with a compound of formula II
• G--(E).sub.n II
• in which
• E represents at least one of --OH, --NH.sub.2 and --NHR in which R is an alkyl group having 1 to 4 carbon atoms,
• n represents 2 or 3, and
• G represents an aliphatic, cycloaliphatic and/or aromatic group containing at least 2 carbon atoms, having an average molecular weight M.sub.n of not more than 3000, and which may contain at least one group selected from the group consisting of --O--, --COO--, --CONH--, --S-- and --SO.sub.2 --,
• in an amount sufficient to react 1 to 50% of the isocyanate groups originally present in the isocyanate, and to react a total of 20 to 85% of the isocyanate groups originally present in the polyisocyanate in stages (a) and (b);
• and
• (c) reacting with a compound of formula III
• Z--(CH.sub.2).sub.p --Q III
• in which
• Q represents --OH, --SH, --NH.sub.2 or --NHR in which R is an alkyl group having 1 to 4 carbon atoms,
• Z represents an aliphatic group having 2 to 10 C atoms and carrying at least one tertiary amino group or represents a heterocyclic group having at least one basic ring nitrogen atom not bonded to a hydrogen atom, and
• p is 0 when Z is an aliphatic group or an integer from 0 to 10 when Z is a heterocyclic group,
• in an amount sufficient to provide at least one molecule of formula III for each isocyanate group in the polyisocyanate unreacted after stages (a) and (b);
• wherein
• at least 1 mole % of the compound of formula I defined above is replaced by a compound of formula Ia
• Y'--OH Ia
• in which Y' represents an aliphatic, cycloaliphatic or aromatic group having an average molecular weight M.sub.n of 200 to 10,000 in which hydrogen atoms may be partly replaced by halogen and containing at least one --NHCOO-- group, or
• at least 1 mole % of the compound of formula I defined above is replaced by a monohydroxyfunctional polyacrylic or polymethacrylic acid ester or a copolymer thereof with up to 50 mole % relative to monomer units of a vinyl comonomer, having an average molecular weight Mn of not more than 10,000, or
• at least 1 mole % of the compound of formula II defined above is replaced by a compound of formula IIa
• G'--(OH).sub.n IIa
• in which G' represents an aliphatic, cycloaliphatic or aromatic group containing at least 2 carbon atoms, having an average molecular weight M.sub.n of not more than 3000, and containing at least one --NHCOO-- or --Si(CH.sub.3).sub.2 O-- group, and n represents a number from 2 to 3.