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Surface active polycarbodiimides and their dispersions

Assignee: Union Carbide Corp
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Filing: 1987-03-31
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Granted: —
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Expires: 2007-03-31
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Abstract

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.

Inventors

  • 👤 James Wayne Taylor

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-31 16:09
CPC Classifications
C; C08; C08F; C08F20/00; C08F20/02; C08F20/52; C09; C09K; C09K23/00; C09K23/22; C08K; C08K5/00; C08K5/16; C08K5/29; C09K23/16; Y; Y10; Y10S; Y10S260/00; Y10S260/21; Y10S260/45; Y10S516/00; Y10S516/01; Y10S516/03; Y10S516/05; Y10S516/06; Y10S516/07; Y10S516/905; Y10S516/914; Y10S516/915; Y10S516/916; Y10S525/00; Y10S525/907

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 83 words
A surface-active polycarbodiimide of the formula wherein R is a residue of a hydrophobic organic compound containing at least two carbodiimide groups; R' is. a residue of an organic compound having a hydrophilic segment and at least one functional group capable of reacting with a carbodiimide group; and X is a group formed by the reaction of a said carbodiimide group with a said functional group, preferably selected from the group consisting of uretidinone, diazetidine thione, N-acyl urea, guanidine, isourea, isothiourea, and carbodiimide.
Claim 2
Dependent Claim 83 words
A surface-active polycarbodiimide of the formula wherein R is a residue of a hydrophobic organic compound containing at least two carbodiimide groups; R' is. a residue of an organic compound having a hydrophilic segment and at least one functional group capable of reacting with a carbodiimide group; and X is a group formed by the reaction of a said carbodiimide group with a said functional group, preferably selected from the group consisting of uretidinone, diazetidine thione, N-acyl urea, guanidine, isourea, isothiourea, and carbodiimide.
Claim 3
Dependent Claim 44 words
A surface-active polycarbodiimide of Claim 1 wherein R' is a residue of a hydroxyl-containing poly-(alkylene oxide)-based surfactant, preferably in alkoxy-capped, the number of alkylene oxide repeating unites (n) preferably being from 15 to 120, and especially the poly-(alkylene oxide)-based sufactant is a methoxypolyethylene glycol.
Claim 4
Dependent Claim 163 words
A surface-active polycarbodiimide of Claim 1 wherein R is a residue of a monodisperse, branched polycarbodiimide, which preferably has the generalized structure: 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 of 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.
Claim 5
Dependent Claim 162 words
A surface-active polycarbodiimide of Claim 3 wherein the monodisperse, branched pofycarbodiimide has the generalized structure: Wherein: R', R 2 , R 3 and R 4 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, or the generalized structure: wherein: R T , R 2 , and R 4 may be the same or different. and represent alkyl groups having 1 to about 12 carbon atoms; R S and R 6 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.
Claim 6
Dependent Claim 100 words
A surface-active polycarbodiimide of claim 3 wherein the monodisperse, branched polycarbodiimide is 1,3,6-tri-(N-isopropyt-N'-methylene carbodiimide) hexane, 1,3,6-tri-(N-cyclohexyl-N'-methylene carbodiimide) hexane or 1,3,6-tri-(N-n-butyl-N'methytene carbodiimide) hexane. A surface-active polycarbodiimide of Claim 1 wherein R is a residue of polydisperse, linear polycarbodiimide, preferably a residue of a polyfunctional polycarbodiimide(PCDI) 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.
Claim 7
Dependent Claim 32 words
An emulsion comprising an admixture in aqueous medium of: (a) a hydrophobic polycarbodiimide, and (b) a surface-active polycarbodiimide according to anyone of claims 1 to 6 and optionally (c) a supplemental sufactant.
Claim 8
Dependent Claim 47 words
A cross-linkable composition comprising an admixture of (a) an emulsion of a carboxyl-containing resin or neutralized, carboxylated, water-soluble organic resin, and (b) a surface-active polycarbodiimide according to anyone of claims 1 to 6 and/or (c) an emulsion according to Claim 7, and optionally (d) a supplemental surfactant
Claim 9
Independent Claim 46 words
A method of making a surface-active polycarbodiimide comprising reacting, in the presence of a catalyst, a hydrophobic organic compound containing at least two carbodiimide groups with an organic compound having a hydrophilic segment and at least one functional group capable of reacting with a carbodiimide group.
Claim 10
Independent Claim 46 words
A method of making a surface-active polycarbodiimide comprising reacting, in the presence of a catalyst, a hydrophobic organic compound containing at least two carbodiimide groups with an organic compound having a hydrophilic segment and at least one functional group capable of reacting with a carbodiimide group.
Claim 11
Independent Claim 43 words
A method of making an emulsion comprising mixing, in aqueous medium: (a) a hydrophobic carbodiimide, and (b) the surface-active carbodiimide of anyone of claims 1 to 6, wherein the surface-active carbodiimide preferably is formed in situ in a matrix of the hydrophobic carbodiimide.
Claim 12
Dependent Claim 36 words
A method of making a cross-linkable composition comprising mixing: (a) an emulsion of a carboxyl-containing resin, (b) a surface-active polycarbodiimide according to anyone of claims 1 to 6 and/or (c) an emulsion according to claim 7
Claim 13
Independent Claim 46 words
A method for cross-linking a carboxyl-containing resin or a neutralized, carboxylated, water-soluble organic resin comprising: (a) mixing said resin with an emulsion of a surface-active carbodiimide of anyone of claims 1 to 6 and (b) allowing volatilization of certain formulated materials, to produce a cross-linked product
Claim 14
Dependent Claim 10 words
A cross-linked product formed by the method of claim 12.
Claim 15
Dependent Claim 8 words
Claims for the following Contracting State : AT
Claim 16
Independent Claim 126 words
A method for preparing a surface-active polycarbodiimide of the formula wherein R is a residue of a hydrophobic organic compound containing at least two carbodiimide groups; R' is a residue of an organic compound having a hydrophilic segment and at least one functional group capable of reacting with a carbiodiimide group; and X is a group formed by the reaction of a said carbodiimide group with a said functional group, preferably selected from the group consisting of uretidionone, diazetidine thione, N-acyl urea, guanidine, isourea, isothiourea, and carbodiimide. comprising reacting, in the presence of a catalyst, a hydrophobic organic compound containing at least two carbodiimide groups with an organic compound having a hydrophilic segment and at least one functional group capable of reacting with a carbodiimide group.
Claim 17
Independent Claim 126 words
A method for preparing a surface-active polycarbodiimide of the formula wherein R is a residue of a hydrophobic organic compound containing at least two carbodiimide groups; R' is a residue of an organic compound having a hydrophilic segment and at least one functional group capable of reacting with a carbiodiimide group; and X is a group formed by the reaction of a said carbodiimide group with a said functional group, preferably selected from the group consisting of uretidionone, diazetidine thione, N-acyl urea, guanidine, isourea, isothiourea, and carbodiimide. comprising reacting, in the presence of a catalyst, a hydrophobic organic compound containing at least two carbodiimide groups with an organic compound having a hydrophilic segment and at least one functional group capable of reacting with a carbodiimide group.
Claim 18
Dependent Claim 43 words
A method of claim 1 wherein R' is a residue of a hydroxyl-containing poly-(alkylene oxide)-based surfactant, preferably is alkoxy-capped, the number of alkylene oxide repeating unites (n) preferably being from 15 to 120, and especially the poly-(alkylene oxide)-based sufactant is a methoxypolyethylene glycol.
Claim 19
Dependent Claim 162 words
A method of claim 1 wherein R is a residue of a monodisperse, branched polycarbodiimide, which preferably has the generalized structure: 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.
Claim 20
Dependent Claim 160 words
A method of Claim 3 wherein the monodisperse, branched polycarbodiimide has the generalized structure: Wherein: R', R 2 , R3 and R 4 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, or the generalized structure: wherein : R', R 2 , and R * may be the same or different and represent alkyl groups having 1 to about 12 carbon atoms; R S and R 6 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.
Claim 21
Dependent Claim 21 words
A method of claim 3 wherein the monodisperse, branched polycarbodiimide is 1,3,6-tri-(N-isopropyl-N'-methylene carbodiimide) hexane, 1,3,6-tri(N-cyclohexyl-N'-methylene carbodiimide) hexane or 1,3,6-tri-(N-n-butyl-N'-methylene carbodiimide) hexane.
Claim 22
Dependent Claim 78 words
A method of Claim 1 wherein R is a residue of a polydisperse, linear polycarbodiimide, preferably a residue of a polyfunctional polycarbodiimide(PCDI) 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.
Claim 23
Dependent Claim 32 words
An emulsion comprising an admixture in aqueous medium of: (a) a hydrophobic polycarbodiimide, and (b) a surface-active polycarbodiimide according to anyone of claims 1 to 6 and optionally (c) a supplemental sufactant
Claim 24
Dependent Claim 48 words
A cross-linkable composition comprising an admixture of (a) an emulsion of a carboxyl-containing resin or neutralized, carboxylated, water-soluble organic resin, and (b) a surface-active polycarbodiimide prepared according to anyone of claims 1 to 6 and/or (c) an emulsion according to Claim 7, and optionally (d) a supplemental surfactant.
Claim 25
Independent Claim 44 words
A method of making an emulsion comprising mixing, in aqueous medium: (a) a hydrophobic carbodiimide, and . (b) the surface-active carbodiimide of anyone of claims 1 to 6, wherein the surface-active carbodiimide preferably is formed in situ in a matrix of the hydrophobic carbodiimide.
Claim 26
Dependent Claim 36 words
A method of making a cross-linkable composition comprising mixing: (a) an emulsion of a carboxyl-containing resin, (b) a surface-active polycarbodiimide according to anyone of claims 1 to 6 and/or (c) an emulsion according to claim 7.
Claim 27
Independent Claim 46 words
A method for cross-linking a carboxyl-containing resin or a neutralized, carboxylated, water-soluble organic resin comprising: (a) mixing said resin with an emulsion of a surface-active carbodiimide of anyone of claims 1 to 6 and (b) allowing volatilization of certain formulated materials, to produce a cross-linked product.
Claim 28
Dependent Claim 10 words
A cross-linked product formed by the method of claim 12.

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