Surface active polycarbodiimides and their dispersions

• US 5,047,588 A
• Filed: 01/30/1989
• Issued: 09/10/1991
• Est. Priority Date: 03/31/1986
• Status: Expired due to Fees

• Current Assignee: Union Carbide Chemicals And Plastics Company, Inc.
• Original Assignee: Union Carbide Chemicals & Plastics Technology Corporation (Dow, Inc.)
• Inventors: Taylor, James W.
• Primary Examiner(s): Reamer, James H.
• Application Number:
  US07/303,231
• Time in Patent Office: 953 Days
• Field of Search: 564/252, 560/115
• US Class Current: 564/252
• CPC Class Codes: C08K 5/29 Compounds containing one or more carbon-to-nitrogen double bonds
• CPC Class Codes: C09K 23/16 Amines or polyamines
• CPC Class Codes: C09K 23/22 Amides or hydrazides
• CPC Class Codes: Y10S 260/21 Polymer chemically or physically modified to impart antistatic properties and methods of antistatic agent addition
• CPC Class Codes: Y10S 260/45 Polymer dispersions
• CPC Class Codes: Y10S 516/05 Organic amine, amide, or n-base containing
• CPC Class Codes: Y10S 516/06 Protein or carboxylic compound containing
• CPC Class Codes: Y10S 516/07 Organic amine, amide, or n-base containing
• CPC Class Codes: Y10S 516/914 The agent contains organic compound containing nitrogen, except if present solely as NH4+
• CPC Class Codes: Y10S 516/915 The compound contains -C[=O]NHH where substitution may be made for the hydrogen
• CPC Class Codes: Y10S 516/916 The compound contains repeating -OCnH2n-, i.e. repeating unsubstituted oxyalkylene
• CPC Class Codes: Y10S 525/907 Polycarbodiimide

Abstract

Disclosed are surface-active polycarbodiimides containing a hydrophilic portion and a hydrophobic portion joined through the reaction of a carbodiimide group with a reactive functional group. The surface-active polycarbodiimides may be linear or branched, monodisperse or polydisperse, but preferably are of the branched, monodispers type. The surface-active polycarbodiimides are useful as surfactants, and are particularly useful as emulsifiers in cross-linkable, carboxyl-containing resin systems, such as aqueous latexes.

Claims

1. A carboxyl-reactive surface-active polycarbodiimide of the formula

View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)

2. A surface-active polycarbodiimide of claim 1 wherein X is selected from the group consisting of uretidinone, diazetidine thione, N-acyl urea, guanidine, isourea, isothiourea, and carbodiimide.

3. A surface-active polycarbodiimide of claim 1 wherein R is a residue of a monodisperse, branched polycarbodiimide.

4. A carboxyl-reactive surface-active polycarbodiimide of claim 3 wherein the monodisperse, branched polycarbodiimide has the generalized structure:

space="preserve" listing-type="equation">M--[(R".sub.d NCN--R).sub.n ].sub.m --[(R".sub.d NCN--R'"'"').sub.p --Q].sub.q

wherein;

M and Q may be the same or different and each represents the residue of a compound adapted to function as a site for branching;

R and R'"'"' may be the same or different and represent an alkyl (including cycloalkyl) or aryl, radical or diradical which may be or contain cyano, nitro, halo, alkyl sulfide, dialkylaminoalkyl, substituted silane, alkoxy, and aryloxy moieties, and other substituted species of any of the foregoing;

R" represents the same or different alkyl (including cycloalkyl) or aryl diradical which may contain cyano, nitro, halo, alkyl sulfide, dialkylamino, substituted silane, alkoxy, and aryloxy moieties, and other substituted species of any of the foregoing; and

wherein d is 0 to about 12, n is 0 to about 6, m is 3 to about 5, p is 1 to about 6, and q is 0 to about 4.

5. A surface-active polycarbodiimide of claim 4 wherein the monodisperse, branched polycarbodiimide has the generalized structure:

##STR6## wherein;

R¹, R², R³ and R⁴ may be the same or different and represent organic residues which do not substantially interfere with the multifunctional carbodiimide for its intended purpose; and

D is an organic residue; and

r, s, t, x and y are 1 to about 6.

6. A surface-active polycarbodiimide of claim 4 wherein the monodisperse, branched polycarbodiimide has the generalized structure:

##STR7## wherein;

R¹, R², and R⁴ may be the same or different and represent alkyl groups having 1 to about 12 carbon atoms;

R⁵ and R⁶ may be the same or different and represent hydrogen, alkyl (including cycloalkyl), aryl, aralkyl, alkaryl, heterocyclic, cyano, nitro, halo, alkyl sulfide, dialkylaminoalkyl, silane, alkoxy, and aryloxy groups, and substituted species of any of the foregoing;

Z is the residue of a compound adapted to function as a site for branching; and

wherein a, b, and c are 0 to about 12.

7. A surface-active polycarbodiimide of claim 4 wherein the monodisperse, branched polycarbodiimide is 1,3,6-tri-(N-isopropyl-N'"'"'-methylene carbodiimide) hexane.

8. A surface-active polycarbodiimide of claim 4 wherein the monodisperse, branched polycarbodiimide is 1,3,6-tri-(N-cyclohexyl-N'"'"'-methylene carbodiimide) hexane.

9. A surface-active polycarbodiimide of claim 4 wherein the monodisperse, branched polycarbodiimide is 1,3,6-tri-(N-n-butyl-N'"'"'-methylene carbodiimide) hexane.

10. A surface-active polycarbodiimide of claim 1 wherein R is a residue of a polydisperse, linear polycarbodiimide.

11. A surface-active polycarbodiimide of claim 10 wherein R is a residue of a polyfunctional PCD1 derived from the reaction of mono-, di-, and tri-cycloaliphatic or saturated aliphatic isocyanates wherein the cycloaliphatic moieties contain from 5 to about 7 carbons and can be substituted with alkyl having 1 to about 6 carbons, and oxygen, and the saturated aliphatic moieties contain from 1 to about 18 carbons, wherein the mono- and triisocyanates are optional.