Reaction products containing urethane groups and urea groups

Abstract

The present invention relates to reaction products containing urethane groups and urea groups, containing at least one species of general formula (I), to a method for producing said reaction products, to the use of said reaction products as wetting agents, dispersants, dispersion stabilizers, and/or adhesion promoters, and to compositions that contain the reaction products containing urethane groups and urea groups.

1 . A reaction product containing urethane and urea groups, comprising at least one species of the general formula (I) 
       
         
           
           
               
               
           
         
         where a+b+c=x,
 r+s=q−1 
 p+y=w−1 
 
         x is an integer from 2 to 10, 
         a is an integer from 1 to 9, 
         b is an integer from 1 to 9, 
         c is an integer from 0 to 8, 
         q is an integer from 1 to 5, 
         r is an integer from 0 to 4, 
         s is an integer from 0 to 4, 
         w is an integer from 1 to 10, 
         p is an integer from 0 to 9, 
         y is an integer from 0 to 9, and 
       
       R is the organic radical of a corresponding polyisocyanate R(NCO) x , R is a branched or unbranched, saturated or unsaturated organic radical having 1 to 150 carbon atoms and does not contain any free isocyanate groups, 
       the Y radical(s) is/are independently the organic radical(s) of a corresponding alcohol Y(OH) q  where q is an integer from 1 to 5 and Y is a branched or unbranched, saturated or unsaturated organic radical having 1 to 1000 carbon atoms, 
       the X group(s) is/are independently O, NH and/or NZ 2  and the XH group(s) is/are independently a hydroxyl group OH, a primary amino group NH 2  and/or a secondary amino group NHZ 2  where 
       the Z 2  radical(s) is/are independently a branched or unbranched, saturated or unsaturated organic radical G(XH) j (XP) i  where i+j=k, 
       k is an integer from 0 to 9, 
       j is an integer from 0 to 9, 
       i is an integer from 0 to 9, and 
       the G radical is a branched or unbranched, saturated or unsaturated organic radical, and 
       the A radical(s) is/are independently a radical of the general formula (II) 
       
         
           
           
               
               
           
         
       
       where 
       the R 1  radical is H or NH 2  or a branched or unbranched, saturated or unsaturated organic radical having 1 to 25 carbon atoms or, if Z b  is C and R 2  is —CH═N—, where the nitrogen atom of 
       the R 2  radical is bonded directly to Z b  to form a 5-membered ring, R 1  is OH, 
       the Z a  group is CH or N or CR 3  where the R 3  radical is a branched or unbranched, saturated or unsaturated organic radical having 1 to 18 carbon atoms, 
       the Z b  group is CH or N or, if R 1  is OH, Z b  is C, 
       the R 2  radical is H or, if R 1  is OH, R 2  is —CH═N—, and 
       the Z 1  radical(s) is/are independently the organic radical of a corresponding species of the general formula (III)
   (HX) y -Z 1 —(XH) p+1   (III)
 
 
       where 
       Z 1  is a branched or unbranched, saturated or unsaturated organic radical containing 1 to 150 carbon atoms, 
       the P radical(s) is/are independently a radical of the general formula (IVa)
   —(CO)—NH—R-(Q) x−1   (IVa)
 
 
       where 
       the Q radical(s) is/are independently a radical
   —NH—(CO)-A or
 
   —NH—(CO)—X—Z 1 (XH) y (X—U) p  or
 
   —NH—(CO)—O—Y(OH) r (O—U) s  
 
 
       where 
       the U radical(s) is/are independently a radical of the general formula (IVb)
   —(CO)—NH—R—(V) x−1   (IVb)
 
 
       where 
       the V radical(s) is/are independently a radical
   —NH—(CO)-A or
 
   —NH—(CO)—X—Z 1 (XH) y  or
 
   —NH—(CO)—O—Y(OH) r .
 
 
     
     
         2 . The reaction product containing urethane and urea groups as claimed in  claim 1 , containing at least 40% by weight of one or more species of the general formula (I). 
     
     
         3 . The reaction product containing urethane and urea groups as claimed in  claim 1 , wherein x is an integer from 2 to 7, a is an integer from 1 to 6 and b is an integer from 1 to 6. 
     
     
         4 . The reaction product containing urethane and urea groups as claimed in  claim 3 , wherein x is 2, a is 1 and b is 1. 
     
     
         5 . The reaction product containing urethane and urea groups as claimed in  claim 1 , wherein the following conditions are applicable to the A radical(s) of the general formula (II):
 the R 1  radical is H or a branched or unbranched, saturated or unsaturated organic radical having 1 to 25 carbon atoms,   the Z a  group is CH or N,   the Z b  group is CH or N, and   the R 2  radical is H.   
     
     
         6 . The reaction product containing urethane and urea groups as claimed in  claim 1 , wherein p is an integer from 0 to 3, and s is an integer from 0 to 2. 
     
     
         7 . The reaction product containing urethane and urea groups as claimed in  claim 1 , wherein Y contains at least one polyether radical, polyester radical, hydrocarbyl radical and/or polysiloxane radical. 
     
     
         8 . A process for preparing a reaction product containing urethane and urea groups as claimed in  claim 1 , wherein
 i) b alcohols Y—(OH), are reacted with at least one polyisocyanate R(NCO) x  to form at least one urethane of the general formula (V)
   ((HO) q−1 —Y—O—CO—NH) b —R—(NCO) x−b   (V)
 
 where 
 the urethane of the general formula (V) contains at least one free isocyanate group, and 
   ii) at least one urethane of the general formula (V) is reacted with a species of the general formula (IIa)   
       
         
           
           
               
               
           
         
         iii) optionally with c components of the general formula (III)
   (HX) y -Z 1 —(XH) p+1   (III),
 
 
         to give a reaction product containing urethane and urea groups, comprising at least one species of the general formula (I) 
       
       
         
           
           
               
               
           
         
       
     
     
         9 . A wetting agent and dispersant comprising a reaction product containing urethane and urea groups as claimed in  claim 1 . 
     
     
         10 . An adhesion promoter comprising a reaction product containing urethane and urea groups as claimed in  claim 1 . 
     
     
         11 . A composition comprising a reaction product containing urethane and urea groups as claimed in  claim 1 . 
     
     
         12 . A reaction product containing urethane and urea groups as claimed in  claim 1  as an additive, wetting agent, dispersant, dispersion stabilizer, adhesion promoter, viscosity reducer, or compatibilizer in coatings, varnishes, plastics, pigment pastes, sealants, cosmetics, ceramics, adhesives, potting compounds, spackling compounds, printing inks and other inks. 
     
     
         13 . A reaction product containing urethane and urea groups as claimed in  claim 1  which is one species of the general formula (I). 
     
     
         14 . A reaction product containing urethane and urea groups, comprising one or more salt(s) and/or one or more quaternization product(s) of the species of the general formula (I) as claimed in  claim 1 . 
     
     
         15 . A reaction product containing urethane and urea groups, comprising one or more modification products of the species general formula (I) as claimed in  claim 1 , wherein one or more tertiary amino groups in the structural element of the general formula (I) have been converted to amine oxides with oxygen and/or peroxo compounds and/or XH groups still present in the structural element of the general formula (I) have been reacted with carboxylic anhydrides.