Isocyanate functional prepolymers and coating materials based thereon

• US 4,560,494 A
• Filed: 12/27/1984
• Issued: 12/24/1985
• Est. Priority Date: 12/27/1984
• Status: Expired due to Term

• Current Assignee: Sherwin-Williams Company
• Original Assignee: Sherwin-Williams Company
• Inventors: Druetzler, Thomas W.
• Primary Examiner(s): Cockeram, Herbert S.
• Application Number:
  US06/686,943
• Time in Patent Office: 362 Days
• Field of Search: 528/49, 528/59, 528/73, 252/182, 521/902, 521/116
• US Class Current: 560/158
• CPC Class Codes: C08G 18/2815 Monohydroxy compounds
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/6225 Polymers of esters of acrylic or methacrylic acid
• CPC Class Codes: C08G 18/8064 with monohydroxy compounds
• CPC Class Codes: C08L 75/08 from polyethers
• CPC Class Codes: C09D 7/65 macromolecular C09D7/41-C09D7/48 take precedence
• CPC Class Codes: Y10S 521/902 Cellular polymer containing an isocyanurate structure

Abstract

A flexibilizing additive compatible with a wide variety of polymeric vehicles is provided wherein the additive comprises the reaction product of (a) an aliphatic polyisocyanate; (b) at least one monofunctional alcohol containing an ether or carboxyl oxygen; and (c) at least one diol. The flexibilizing additive can be combined with a thermoplastic or thermosetting film-forming vehicle to provide improved coating compositions.

Claims

1. An isocyanate functional urethane which comprises the reaction product of:

(a) an aliphatic polyisocyanate having an average of at least 2.1 isocyanate groups per molecule and selected from the group consisting of the biurets and isocyanurates of linear aliphatic diisocyanates; and

(b) at least one monofunctional alcohol having a molecular weight less than about 500 and which is selected from the group consisting of;

##STR11## wherein n is from 1 to about 10;

R₁ is an aliphatic radical of 1 to about 12 carbons;

R₂ is H or CH₃ ;

R₃ and R₄ are independently aliphatic of 1 to about 12 carbons or H;

R₅ is an aliphatic radical of 1 to about 8 carbons or nothing;

##STR12## where R₆ is an aliphatic radical of 1 to about 12 carbons; and

(c) at least one diol having the formula;

##STR13## wherein R₇ is H or CH₃ and y is from 1 to about 40;

wherein the total NCO/OH equivalents ratio is greater than 1.0 and the ratio of OH equivalents from (b) to OH equivalents from (c) ranges from 0.3;

1 to 2.0;

1.0.

2. The urethane of claim 1 further characterized in that the isocyanate functional urethane has an isocyanate equivalent weight ranging from about 280 to about 4200.

3. The urethane of claim 1 further characterized in that the total NCO/OH equivalent ratio is from 1/0.5 to 1/0.99.

4. The urethane of claim 1 further characterized in that the aliphatic polyisocyanate is selected from the group consisting of the biuret of hexamethylene diisocyanate and the isocyanurate of hexamethylene diisocyanate.

5. The urethane of claim 1 further characterized in that the monofunctional alcohol is ethylene glycol mono butyl ether.

6. An isocyanate functional urethane which comprises the reaction product of:

(a) an aliphatic polyisocyanate selected from the group consisting of the biuret and isocyanurate of hexamethylene diisocyanate; and

(b) at least one monofunctional alcohol having a molecular weight less than about 500 and having the structure;

##STR14## wherein n is from 1 to about 10;

R₁ is an aliphatic radical of 1 to about 6 carbons;

R₂ is H or CH₃ ; and

(c) at least one diol having the formula;

##STR15## wherein R₇ is H or CH₃ ; and

y is from 1 to about 40;

wherein the total NCO/OH equivalents ratio is from 1/0.5 to 1/0.99 and the ratio of OH equivalents from (b) to OH equivalents from (c) ranges from 0.5;

1 to 2.0;

1.

7. The urethane of claim 6 further characterized in that the isocyanate functional urethane has an isocyanate equivalent weight ranging from about 280 to about 4200.

8. The urethane of claim 6 further characterized in that the monofunctional alcohol is ethylene glycol mono butyl ether.