A Process to Produce Polycarbamate, Polycarbamate Produced Thereby and a Coating Composition Comprising the Polycarbamate

Patent metadata

Field	Value
Publication number	US-2016200871-A1
Application number	US-201414912161-A
Country	US
Kind code	A1
Filing date	Aug 15, 2014
Priority date	Aug 15, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

A process to prepare polycarbamate comprising adding urea to a polyol in the presence of at least one catalyst selected from the group consisting of compounds having the following formula M m Z n ; wherein M is a divalent metal, and Z is an anionic functionality or a functionality capable of forming a covalent bond with M and wherein n times a valence number of Z equals X and m times two equals Y wherein the absolute value of X equals the absolute value of Y is provided. Also provided are a polycarbamate produced according to the process and a coating composition comprising the polycarbamate.

First claim

1 . A process to prepare polycarbamate comprising:
adding urea to a polyol in the presence of at least one catalyst selected from the group consisting of compounds having the following formula M m Z n ; wherein M is a divalent metal, and Z is an anionic functionality or a functionality capable of forming a covalent bond with M and wherein n times a valence number of Z equals X and m times two equals Y wherein the absolute value of X equals the absolute value of Y.

2 . The process according to claim 1 , wherein a second catalyst selected from the group consisting of carbamylation catalysts is present.

3 . The process according to claim 2 , wherein the second catalyst is dibutyltin oxide and/or dibutyltin acetate.

4 . The process according to claim 1 , wherein M is Manganese (II) (“Mn(II)”), Zinc(II) (“Zn(II)”), Calcium(II) (“Ca(II)”), Magnesium(II) (“Mg(II)”), Lead(II) (“Pb”), Cobalt (II) (“Co”) and Barium(II) (“Ba(II)”).

5 . The process according to claim 1 , wherein anionic functionalities (ligands) include 2-ethylhexanoate, benzoate, hexafluoroacetylacetonate, isopropoxide, acetyl acetonate, phenoxide, 2-mercaptopyridine-N-oxide, toluenesulfonate, stearate, tert-butoxide, neodecanoate, citrate, trifluoromethane sulfonate, n-butoxide, trifluoroacetate, dibutyldithiocarbamate, 1,1,1-trifluoro-2,4-pentanedionate, 2,2,6,6,-tetramethyl-3,5-hexanedionate, cresylate, ethoxide, methoxide, triethanolaminato, 2-methyl-2-butoxide, oxo, fluoride, chloride, bromide or iodide as well as other anionic functionalities capable of binding to a trivalent metal

6 . The process according to claim 1 , wherein the catalyst is selected from the group consisting of: Zn(II) acetylacetonate, Zn(II) 2-ethylhexanoate, Zn(II) triflate, Zn(II) trifluoro acetate hydrate, Zn(II) 2-mercaptopyridine-N-oxide, Zn(II) Bis(2,2,6,6-tetramethyl-3,5-hetanedionate, Zn(II) toluenesulfonate, Zn(II) dibutyldithiocarbamate, Zn(II) hexafluoroacetylacetonate , zinc oxides, zinc halides, zinc hydroxide and zinc halide hydroxide and any combination thereof.

7 . The process according to claim 1 , wherein the catalyst is selected from the group consisting of: Ca(II) acetylacetonate, Ca(II) 2-ethylhexanoate, Ca(II) bis(trifluoromethanesulfonate), Calcium carbonate, Calcium stearate, Ca(ClO 4 ) 2 , Calcium halides, Calcium hydroxide, Calcium methoxide, Calcium ethoxide, Calcium isopropoxide and Ca(II)oxide and any combination thereof.

8 . The process according to claim 1 , wherein the catalyst is selected from the group consisting of: Mg(II) acetylacetonate, Mg(II) 2-ethylhexanoate, Mg(II) bis(trifluoromethanesulfonate), Magnesium carbonate, Magnesium stearate, Mg(ClO 4 ) 2 , and Magnesium halides, Magnesium hydroxide, Magnesium ethoxide, Magnesium butoxide, Mg(II)oxide and any combination thereof.

9 . The process according to claim 1 any one of the preceding claims having a hydroxyl conversion greater than a comparative process identical in components and conditions except in the absence of a catalyst.

10 . A polycarbamate produced according to the process of claim 9 .

11 . A coating comprising the polycarbamate according to claim 10 .

Assignees

• Dow Global Technologies Llc

Inventors

• Yu Xinrui
• He Ylyong
• Hull Jr John W
• Beigzadeh Daryoosh
• Romer Duane R
• Clark Thomas P
• Margl Peter
• Lu Congcong

Classifications

• C08G65/33306

  acyclic · CPC title

• C08G65/33324

  acyclic · CPC title

• C08G71/04 Primary

  Polyurethanes · CPC title

• C09D175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title