Water-dispersible polyurethanes

• US 4,190,566 A
• Filed: 12/02/1976
• Issued: 02/26/1980
• Est. Priority Date: 12/10/1975
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Pedain, Josef, Noll, Klaus
• Primary Examiner(s): Cockeram, H. S.
• Application Number:
  US05/746,919
• Time in Patent Office: 1,181 Days
• Field of Search: 260/29.2 TN, 260/77.5 AQ, 260/77.5 AT, 260/77.5 AM, 260/75 NQ, 260/75 NT, 260/75 NP, 528/76, 528/79, 528/80
• US Class Current: 524/839
• CPC Class Codes: C08G 18/4837 and other oxyalkylene units
• CPC Class Codes: C08G 18/5042 containing ureum groups
• CPC Class Codes: C08G 18/7818 containing ureum or ureum derivative groups
• CPC Class Codes: C08G 18/8064 with monohydroxy compounds

Abstract

The present invention relates to non-ionic, water-dispersible polyurethanes having a substantially linear molecular structure and lateral polyalkylene oxide polyether chains containing ethylene oxide units characterized in that from about 40 to 95% of the alkylene oxide units of the lateral polyalkylene oxide polyether chains consist of ethylene oxide units and from about 5 to 60% consist of propylene oxide, butylene oxide or styrene oxide, to aqueous dispersions of these non-ionic, water-dispersible polyurethanes and to processes for producing these non-ionic, water-dispersible polyurethanes.

Claims

1. Non-ionic, water-dispersible polyurethanes produced using an isocyanate group to isocyanate-reactive group equivalent ratio of from about 0.8:

1 to 2.5;

1 having a substantially linear molecular structure and about 3 to 30% by weight, based on the weight of the polyurethane, of lateral polyalkylene oxide polyether chains containing ethylene oxide units which are responsible for dispersibility, wherein from about 40 to 95% of the alkylene oxide units of the lateral polyalkylene oxide polyether chains, based on the number of alkylene oxide units, consist of ethylene oxide units and from about 5 to 60% are selected from the group consisting of propylene oxide, butylene oxide and styrene oxide units.

2. Aqueous dispersions of the polyurethanes claimed in claim 1.

8. The aqueous dispersions of claim 2 wherein the average particle size is from about 10 mμ

to 5μ

.

3. A process for producing water-dispersible polyurethanes having a substantially linear molecular structure and about 3 to 30% by weight, based on weight of the polyurethane, of lateral polyalkylene oxide polyether chains by reacting organic diisocyanates with difunctional organic compounds ("difunctional" in the context of the isocyanate polyaddition reaction) containing terminal isocyanate-reactive hydrogen atoms and having a molecular weight of from about 300 to 6000 in the presence of synthesis components containing hydrophilic groups which guarantee the dispersibility of the polyurethanes and optionally in the presence of chain extenders having a molecular weight below about 300 known in polyurethane chemistry and optionally in the presence of the aids and additives commonly used in polyurethane chemistry, wherein the synthesis components containing hydrophilic groups are diols corresponding to the following general formula:

##STR7## and/or diisocyanates corresponding to the following general formula;

##STR8## wherein R--represents a difunctional radical of the type obtained by removing the isocyanate groups from a diisocyanate having a molecular weight of from about 112 to 1000,

R'"'"'--represents a hydrogen atom or a monofunctional hydro-carbon radical having from 1 to 8 carbon atoms,

X--represents a difunctional radical obtained by removing the terminal oxygen atom from a polyalkylene oxide radical having from about 5 to 90 alkylene oxide units, of which, based on the number thereof, from about 40 to 95% consist of ethylene oxide units and from about 5 to 60% are selected from the group consisting of propylene oxide, butylene oxide and styrene oxide units,

Y--represents oxygen or --NR"'"'"'--,

R" and R"'"'"' which may be the same or different, each represent monofunctional hydrocarbon radicals having from 1 to 12 carbon atoms, and

Z--represents a radical which has the same definition as Y

and wherein the equivalent ratio of isocyanate groups to isocyanate-reactive groups is from about 0.8;

1 to 2.5;

1.

4. A process for the production of a non-ionic water-dispersible polyurethane having a substantially linear molecular structure comprising reacting in an equivalent ratio of isocyanate groups to isocyanate-reactive groups of from about 0.8:

1 to 2.5;

1;

(a) organic diisocyanates,

(b) organic difunctional compounds having isocyanate-reactive end groups and having a molecular weight of from about 300 to 6000, and

(c) synthesis components containing hydrophilic groups which are responsible for the dispersibility of the polyurethane, said synthesis components selected from the group consisting of diols of the formula ##STR9## and diisocyanates of the formula ##STR10## wherein R--represents a difunctional radical of the type obtained by removing the isocyanate groups from a diisocyanate having a molecular weight of from about 112 to 1000,

R'"'"'--represents a hydrogen atom or a monofunctional hydrocarbon radical having from 1 to 8 carbon atoms,

X--represents a difunctional radical obtained by removing the terminal oxygen atom from a polyalkylene oxide radical having from about 5 to 90 alkylene oxide units, of which, based on the number thereof, from about 40 to 95% consist of ethylene oxide units and from about 5 to 60% consist of the alkylene oxide units selected from the group consisting of propylene oxide, butylene oxide and styrene oxide units,

Y--represents oxygen or --NR"'"'"'--,

R" and R"'"'"', which may be the same or different, each represent monofunctional hydrocarbon radicals having from 1 to 12 carbon atoms, and

Z--represents a radical which has the same definition as Y,

so as to produce a polyurethane which contains from about 3 to 30% by weight of lateral polyalkylene polyether chains.

5. The process of claim 4 wherein X represents a difunctional polyalkylene oxide radical having from about 20 to 70 alkylene oxide units, of which, based on the number thereof, from about 60 to 90% consist of ethylene oxide units and from about 10 to 40% consist of alkylene oxide units selected from the group consisting of propylene oxide, butylene oxide and styrene oxide units.

6. The process of claim 4 wherein chain extenders having a molecular weight below about 300 are used.

7. The process of claim 4 wherein the organic difunctional compounds having isocyanate-reactive end groups are selected from the group of compounds consisting of dihydroxy polyesters, dihydroxy polylactones, dihydroxy polyethers and dihydroxy polycarbonates.

9. Non-ionic, water-dispersible polyurethanes produced using an isocyanate group to isocyanate-reactive group equivalent ratio of from about 0.95:

1 to 1.5;

1 having a substantially linear molecular structure and about 3 to 30% by weight, based on the weight of the polyurethane, of lateral polyalkylene oxide polyether chains containing ethylene oxide units which are responsible for dispersibility, wherein from about 40 to 95% of the alkylene oxide units of the lateral polyalkylene oxide polyether chains, based on the number of alkylene oxide units, consist of ethylene oxide units and from about 5 to 60% are selected from the group consisting of propylene oxide, butylene oxide and styrene oxide units, said alkylene oxide units contributed by synthesis components selected from the group consisting of diols of the formula ##STR11## and diisocyanates of the formula ##STR12## wherein R--represents a difunctional radical of the type obtained by removing the isocyanate groups from a diisocyanate having a molecular weight of from about 112 to 1000,

R'"'"'--represents a hydrogen atom or a monofunctional hydrocarbon radical having from 1 to 8 carbon atoms,

X--represents a difunctional radical obtained by removing the terminal oxygen atom from a polyalkylene oxide radical having from about 5 to 90% alkylene oxide units, of which, based on the number thereof, from about 40 to 95% consist of ethylene oxide units and from about 5 to 60% consist of the alkylene oxide units selected from the group consisting of propylene oxide, butylene oxide and styrene oxide units,

Y--represents oxygen or --NR"'"'"'--,

R" and R"'"'"', which may be the same or different, each represent monofunctional hydrocarbon radicals having from 1 to 12 carbon atoms, and

Z--represents a radical which has the same definition as Y.