Resin, composition and use

Patent metadata

Field	Value
Publication number	US-9902870-B2
Application number	US-201314398051-A
Country	US
Kind code	B2
Filing date	May 8, 2013
Priority date	May 8, 2012
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

There is described a low VOC, unsaturated alkyd resin obtained by reacting (A) to (E): (A) optionally from 0 to 30% w/w naturally occurring Rosin, comprising from 40 to 80 w/w parts per hundred of Rosin of an unsaturated mono carboxylic acid with at least one C 15-25 cyclohydrocarbo moiety capable of a Diels Alder or Ene reaction (pref monoacids being abietic acid, palustric acid, levopimaric acid, sandaracopimaric acid, and/or anhydrides thereof); (B) from 25 to 80% w/w of a linear C 12-60 hydrocarbo carboxylic acid with at least one (preferably at least two conjugated) C═C bonds (=unsaturated fatty acid); (C) optionally from 1 to 30% w/w of an ethylenically unsaturated C 5-6 hydrocarbo dicarboxylic acid and/or anhydride thereof, being reactive as a dienophile and/or enophile with A and/or B (pref C are itaconic acid, citraconic acid and/or anhydrides thereof); (D) from 1 to 40% w/w of at least one polyol; (E) optionally at least one monomer other than A to D—the total of A to E being 100%. There is a further optional step (II) where more or new (C) may be blended with the alkyd resin; the amount of C in blend being from 1 to 30 parts w/w of 100 parts of monomers (A) to (E)—and where (C) is at least used as a monomer and/or as a diluent in the blend and where alkyd resin (i) has acid value of <50 KOH/g of alkyd; (ii) Mn of >=1200 g/mol (iii) oil length <80; (iv) optionally biorenewable content >=50%.

First claim

The invention claimed is:

1. A low VOC alkyd resin blended composition comprising unsaturated alkyd resin P′ obtained by reaction in a process (I) between the following components:
(A) Optional Component A comprising from 0 to 30% by weight of naturally occurring Rosin, the Rosin comprising from 40 to 80 parts per hundred by weight of Rosin of an unsaturated mono carboxylic acid comprising at least one C 15-25 cyclohydrocarbo moiety capable of undergoing a Diels Alder or Ene reaction;
(B) Component B comprising from 25 to 80% by weight of a linear C 12-60 hydrocarbo carboxylic acid comprising at least one conjugated ethylenically unsaturated double bond;
(C) Optional Component C comprising from 1 to 30% by weight of an ethylenically unsaturated C 5-6 hydrocarbo dicarboxylic acid, ester thereof, and/or anhydride thereof, being reactive as a dienophile and/or enophile with Component B and/or Component A where present;
(D) Component D comprising from 1 to 40% by weight of at least one polyhydric alcohol (polyol);
(E) Optional Component E comprising at least one monomer other than any of Components A to D;
the total of Components A to E being100%;
to obtain the alkyd resin P′ and then
(II) in a blending step, adding Component C as a diluent to the alkyd resin P′ to form an admixture therewith; Component C being present in an amount of from 1 to 30 parts by weight with respect to 100 parts of monomers (A) to (E) above;
wherein the alkyd resin P′ obtained from the process (I) has:
(i) an acid value of no more than 50 mg KOH per g of the solid alkyd resin;
(ii) a number average molecular weight (Mn) of at least 1200 g/mol;
(iii) optionally an oil length less than 80; and
(iv) optionally a renewable content of at least 50% by weight of components (A) to (E) where present; and
wherein low VOC denotes that the total amount of organic compounds that have a boiling point from 50 to 250° C. that are present in the composition is less than 100 g/I.

2. The low VOC alkyd resin blended composition as claimed in claim 1 , wherein the alkyd resin P′ obtained from the process (I) has an oil length less than 80.

3. The low VOC alkyd resin blended composition as claimed in claim 1 , wherein the alkyd resin P′ obtained from the process (I) has an oil length less than or equal to 78.

4. The low VOC alkyd resin blended composition as claimed in claim 1 , wherein the alkyd resin P′ obtained from the process (I) has an oil length from 60 to 78.

5. The low VOC alkyd resin blended composition as claimed in claim 1 , wherein the alkyd resin P′ obtained from the process (I) has an oil length from 65 to 78.

6. The low VOC alkyd resin blended composition as claimed in claim 1 , wherein Component C used as a diluent in the blending step (II) is selected from itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride and/or mixtures thereof; and wherein the amount of unreacted Component C present as a diluent in the blending step (II) is from 5 to 28 parts by weight relative to the total amount of monomer A to E being 100 parts by weight.

7. The low VOC alkyd resin blended composition as claimed in claim 2 , wherein Component C used as a diluent in the blending step (II) is selected from itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride and/or mixtures thereof; and wherein the amount of unreacted Component C present as a diluent in the blending step (II) is from 5 to 28 parts by weight relative to the total amount of monomer A to E being 100 parts by weight.

8. The low VOC alkyd resin blended composition as claimed in claim 3 , wherein Component C used as a diluent in the blending step (II) is selected from itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride and/or mixtures thereof; and wherein the amount of unreacted Component C present as a diluent in the blending step (II) is from 5 to 28 parts by weight relative to the total amount of monomer A to E being 100 parts by weight.

9. The low VOC alkyd resin blended composition as claimed in claim 4 , wherein Component C used as a diluent in the blending step (II) is selected from itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride and/or mixtures thereof; and wherein the amount of unreacted Component C present as a diluent in the blending step (II) is from 5 to 28 parts by weight relative to the total amount of monomer A to E being 100 parts by weight.

10. The low VOC alkyd resin blended composition as claimed in claim 5 , wherein Component C used as a diluent in the blending step (II) is selected from itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride and/or mixtures thereof; and wherein the amount of unreacted Component C present as a diluent in the blending step (II) is from 5 to 28 parts by weight relative to the total amount of monomer A to E being 100 parts by weight.

11. The low VOC alkyd resin blended composition as claimed in claim 1 , wherein the Component C used as a monomer in the process (I) is not optional, and wherein the process (I) comprises a cyclo-addition step and an esterification step which may be performed in any order, wherein
the cyclo-addition step of process (I) comprises cyclo-reacting Component (C) which is reactive as a dienophile and/or enophile and comprises an ethylenically unsaturated C 5-6 hydrocarbo dicarboxylic acid, ester thereof, and/or anhydride thereof, with at least one dienophile and/or enophile reactive component selected from the group consisting of:
Component (A) comprising a naturally occurring Rosin comprising from 40 to 80 parts per hundred by weight of Rosin of an unsaturated mono carboxylic acid comprising at least one C 15-25 cyclohydrocarbo moiety capable of undergoing a Diels Alder or Ene reaction;
Component (B) comprising a linear C 12-60 hydrocarbo carboxylic acid comprising at least one conjugated ethylenically unsaturated double bond;
an alkyd adduct formed by reacting Component (D) comprising a polyol with at least one of Component (A) and Component (B); and wherein

the esterification step of process (I) comprises reacting at least one acid functional component selected from the group consisting of;
an acid functional alkyd adduct formed by reacting Component (D) with at least one of Component (A) and Component (B);
Component (A); and
Component (B);

with at least one hydroxy functional component selected from the group consisting of:
a hydroxyl functional alkyd adduct formed by reacting a Component (D) with at least one of Component (A) and Component (B); and
Component D; wherein

the Component (B) is present in at least one of the cyclo-addition step and the esterification step; and
the Component (D) is present in at least one of the cyclo-addition step and the esterification step.

12. The low VOC alkyd resin blended composition as claimed in claim 11 , wherein the Component C used as a monomer in the process (I) is not optional, and wherein the process (I) comprises the steps of:
(1) cyclo-reacting in a first (cycloaddition) step:
(i) Component (C) being reactive as a dienophile and/or enophile and comprising an ethylenically unsaturated C 5-6 hydrocarbo dicarboxylic acid, ester thereof, and/or anhydride thereof, with at least one of
(ii) optional Component (A) comprising a naturally occurring Rosin comprising from 40 to 80 parts per hundred by weight of Rosin of an unsaturated mono carboxylic acid comprising at least one C 15-25 cyclohydrocarbo moiety capable of undergoing a Diels Alder or Ene reaction; and/or
(iii) optional Component (B) comprising a linear C 12 -60 hydrocarbo carboxylic acid comprising at least one conjugated ethylenically unsaturated double bond;
to

Assignees

• Dsm Ip Assets Bv

Inventors

• Hendriks Johannes Wilhelmus Maria
• Lansbergen Adrianus Jozephus Hendricus

Classifications

• C08G63/48

  by unsaturated higher fatty oils or their acids; by resin acids · CPC title

• C08G63/52

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

• C08G63/54

  the acids or hydroxy compounds containing carbocyclic rings · CPC title

• C09D167/08 Primary

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

• C08G63/47

  by unsaturated monocarboxylic acids or unsaturated monohydric alcohols or reactive derivatives thereof · CPC title