Polyfunctional compounds

Patent metadata

Field	Value
Publication number	US-10189783-B2
Application number	US-201515535832-A
Country	US
Kind code	B2
Filing date	Dec 21, 2015
Priority date	Dec 19, 2014
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

The present invention relates to a an imide compound according to anyone of formulas Ia, Ib, Ic, or Ie wherein R1 is H or a C1-C20 optionally substituted hydrocarbon group; both R2 and R5 are a COOH group or one of R2 and R5 is a COOH group while the other substituent is H, methyl or ethyl group; R3 and R4 are independently H, or C1-C20 optionally substituted hydrocarbon group; R6 is H or a methyl group; R7 and R8 are independently H, methyl or ethyl.

First claim

The invention claimed is:

1. An imide compound according to any one of formulas Ia, Ib, Ic, Id or Ie:

wherein R 1 is H, methyl, hydroxymethyl, 1-hydroxyethyl, isopropyl, sec-butyl, 2-methyl-propyl, 2(methylthio)ethyl, benzyl, tolyl, parahydroxytolyl, or an organic fragment of an amino acid selected from the group consisting of arginine, histidine, lysine, aspartic acid, glutamic acid, serine, threonine, asparagine, glutamine, cysteine, selenocysteine, glycine, proline, alanine, valine, isoleucine, methionine, phenylalanine, tyrosine and tryptophan;
both R 2 and R 5 are a COOH group or one of R 2 and R 5 is a COOH group while another of R 2 and R 5 is H, methyl or an ethyl group;
R 3 and R 4 are independently H or a C1-C20 hydrocarbon group;
R 6 is H or a methyl group; and
R 7 and R 8 are independently H, methyl or ethyl.

2. The compound according to claim 1 , wherein R 6 is a methyl group.

3. The compound according to claim 1 , wherein R 1 is selected from H, methyl, hydroxymethyl, 1-hydroxyethyl, isopropyl, sec-butyl, 2-methyl-propyl, 2(methylthio)ethyl, benzyl, tolyl and parahydroxytolyl.

4. The compound according to claim 1 , wherein R 1 is selected from H and benzyl.

5. The compound according to claim 1 , wherein one of R 2 and R 5 is a COOH group, while another of R 2 and R 5 is H, methyl or an ethyl group.

6. The compound according to claim 1 , wherein one of R 2 and R 5 is a COOH group, while another of R 2 and R 5 is methyl.

7. The compound according to claim 1 , wherein R 3 and/or R 4 is H.

8. A polyester prepared from a compound according to claim 1 .

9. A polyester comprising a compound according to claim 1 .

10. A resin composition comprising at least one compound according to claim 1 .

11. An alkyd resin composition comprising:
(a) 1-60 wt % of a compound according to claim 1 ;
(b) 10-40 wt % of an alcohol having a number average hydroxyl functionality ≥2.0; and
(c) 30-70 wt % of fatty acids and/or vegetable oils, wherein
the wt % is determined relative to total of weight of compounds (a), (b), and (c).

12. An alkyd resin obtained by polycondensation of an alkyd resin composition according to claim 11 .

13. A coating obtained by applying a layer of the alkyd resin according to claim 12 on an object followed by curing of the layer.

14. A process of making a polymer or a resin composition using a compound according to claim 1 .

15. An object containing coating layers obtained by application of the alkyd resin according to claim 12 followed by curing.

16. An alkyd emulsion comprising an alkyd resin according to claim 12 , wherein the alkyd emulsion is water borne.

17. A resin for powder coatings, wherein said resin composition comprises
(a′) 1-85 wt % of a compound according to anyone of formulas Ia, Ib, Ic, Id or Ie, as claimed in claim 1 ,
(b′) 10-60 wt % of a diol, and
(c′) 0-80 wt % of a diacid, wherein
the wt % are calculated relative to the total weight of compounds (a′), (b′), and (c′).

18. A resin powder coatings prepared from a resin composition according to claim 17 .

19. A thermosetting powder comprising a resin according to claim 18 .

20. A powder coating derived upon partial or full cure of a thermosetting powder according to claim 19 .

21. A substrate having coated and cured thereon a thermosetting powder according to claim 19 .

Assignees

• Dsm Ip Assets Bv

Inventors

• Koning Cornelis Eme
• Buijsen Paulus Franciscus Anna
• Lansbergen Adrianus Jozephus Hendricus
• Papegaaij Alwin
• Hayden Douglas

Classifications

• C09D167/08

  Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids · CPC title

• C09D5/03

  Powdery paints · CPC title

• C08G73/16 Primary

  Polyester-imides · CPC title

• C08G63/6858

  Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation · CPC title

• C08G63/685

  containing nitrogen · CPC title