Powder coating composition

Patent metadata

Field	Value
Publication number	US-11920058-B2
Application number	US-201916956814-A
Country	US
Kind code	B2
Filing date	Jan 25, 2019
Priority date	Jan 26, 2018
Publication date	Mar 5, 2024
Grant date	Mar 5, 2024

Abstract

The invention relates to powder coating compositions suitable for low temperature powder coating crosslinking typically at curing temperature is between 75 and 140° C. which can be used for powder coating temperature-sensitive substrates like MDF, wood, plastic or temperature sensitive metal alloys.

First claim

The invention claimed is:

1. A powder coating composition comprising one or more crosslinkable components and a catalyst characterized in that the one or more crosslinkable components are crosslinkable by Real Michael Addition (RMA) reaction, the powder coating composition comprising:
a. a crosslinkable component A having at least 2 acidic C—H donor groups in activated methylene or methine,
b. a crosslinkable component B having at least 2 activated unsaturated acceptor groups C═C, which react with component A by Real Michael Addition (RMA) to form a crosslinked network,
c. a latent catalyst system C comprising a strong base or a precursor of a strong base to catalyze the RMA crosslinking reaction at a curing temperature below 200° C. and at least 70° C.,
wherein the catalyst system C is a latent catalyst system LC selected from the group consisting of
a latent catalytic system LCC having chemical latency comprising components that react at the curing temperature to initiate the reaction between crosslinkable components A and B, said latent catalytic system LCC comprising embodiment LCC1:
a) a weak base C2,
b) an activator C1 reactive with C2 or a protonated C2 at the curing temperature, and
c) optionally further comprising an acid C3.

2. The powder coating composition according to claim 1 , wherein in latent catalyst system embodiment LCC1,
the activator C1 is epoxide-, the weak base C2 has a pKa of a conjugated acid of more than 1, units lower than the pKa of the acidic C—H groups of the majority component A, and the weak base C2 is carboxylate, and the latent catalyst system optionally comprises acid C3 having a pKa of more than 1 units lower than the pKa of the acidic C—H groups of majority component A.

3. The powder coating composition according to claim 1 , wherein weak base C2 is added as a salt comprising a cation,
wherein the cation is a non-acidic cation according to formula Y(R′) 4 , wherein Y represents N or P, and wherein each R′ can be a same or different alkyl, aryl or aralkyl group optionally linked to a polymer, or
wherein the cation is a protonated very strong basic amine selected from amidines or guanidines.

4. The powder coating composition according to claim 1 , comprising
a. in catalyst system LCC1, an activator C1 in an amount between 1 and 600 μeq/gr, wherein μeq/gr is μeq relative to total weight of binder components A and B and catalyst system LCC or, in case of catalyst system LCC2, an activator S1 in an amount of at least 1 μeq/gr,
b. weak base C2 in an amount between 1 and 300 μeq/gr relative to total weight of binder components A and B and catalyst system LC,
c. optionally an acid C3 in an amount between 1 and 500,
d. wherein the amount of C1 or respectively S1
i. is higher than the amount of C3 by an amount between 1 and 300 μeq/gr, or
ii. is higher than the amount of C2, or
iii. is higher than the sum of the amount of C2 and C3.

5. The powder coating composition according to claim 1 , wherein
a. the weak base C2 represents between 10 and 100 mol % of the sum of C2 and C3,
b. the amount of acid C3 is 20-400 mol %, of the amount of C2,
c. the ratio of the molar amount of C1 to the sum of the amount of C2 and C3 is at least 0.5, or
d. the ratio of C1 to C3 is at least 1.

6. The powder coating composition according to claim 1 , having a curing profile, as determined by measuring the conversion of the unsaturated bonds C═C of component B as a function of time by FTIR, at a curing temperature chosen between 80 and 200° C., wherein the ratio of the time to go from 20% to 60% C═C conversion to the time to reach 20% conversion is less than 1, with the time to reach 60% conversion being less than 30 min and with the time to reach 20% conversion at 100° C. being at least 1 min.

7. The powder coating composition according to claim 1 , wherein
crosslinkable component A is a malonate, and providing at least 50% of the total of C—H acidic groups in crosslinkable component A,
b. Component B is acryloyl,
wherein at least one of components A or B is a polymer, and

wherein the composition comprises a total amount donor groups C—H and acceptor groups C═C per gram binder solids from 0.05 to 6 meq/gr binder solids, and
the ratio of acceptor groups C═C to donor groups C—H is more than 0.1 and less than 10.

8. The powder coating composition according to claim 1 , wherein at least one of crosslinkable components A or B or a hybrid A/Bis a polymer, wherein the hybrid A/Bis a molecule comprising the crosslinkable components A and B, wherein the polymer is selected from the group consisting of acrylic, polyester, polyester amide, and polyester-urethane polymers, which polymer
a) has a number average molecular weight Mn, as determined with GPC, of at least 450 gr/mole,
b) has a weight average molecular weight Mw, as determined with GPC, of at most 20000 gr/mole,
c) has a molecular weight distribution Mw/Mn below 4,
d) has an equivalent weight EQW in C—H or C═C of at least 150 gr/mole and at most 2500 gr/mole and a number average functionality of reactive groups C—H or C═C between 1-25, C—H groups per molecule,
e) has a melt viscosity at a temperature in the range between 100 and 140° C. less than 60 Pas,
f) comprises amide, urea or urethane bonds and/or comprises high Tg monomers selected from the group consisting of 1,4-dimethylol cyclohexane (CHDM), tricyclodecanedimethanol (TCD diol), isosorbide, penta-spiroglycol or hydrogenated bisphenol A, and tetramethyl-cyclobutanediol, or
g) has a Tg above 25° C. as the midpoint value determined by DSC at a heating rate of 10° C./min or is a crystalline polymer with a melting temperature between 40° C. and 150 as determined by DSC at a heating rate of 10° C./min.

9. The powder coating composition according to claim 1 , comprising one or more components A or B or components of catalyst system C or separate different plasticizers that are in a crystalline or semi-crystalline state in the powder and have a melting temperature between 40 and 130° C.

10. The powder coating composition according to claim 1 , wherein component Bis a polyester(meth)acrylate, a polyester urethane(meth)acrylate, an epoxy (meth)acrylate or a urethane(meth)acrylate, or is a polyester comprising fumarate, maleate or itaconate units, or is a polyester end-capped with isocyanate or epoxy functional activated unsaturated group.

11. A process for the preparation of a powder coating composition according to claim 1 , comprising the step of
a. providing component A, component B, catalyst system C and optional additives,
b. extruding the components, at a temperature Tcomp below 140° C.,
c. cooling, which optionally includes an annealing step to allow crystallization of crystallizable components,
d. shaping the extruded mixture to form a granulate, before, during or after cooling,
e. optionally adding further additives, and
f. grinding the granulate to powder.

12. A method for powder-coating a substrate comprising
a. providing a powder having a powder coating composition according to claim 1 ,
b. applying a layer of the powder to a substrate surface wherein the substrate is a temperature sensitive substrate,
c. heating to a curing temperature Tcur between 75 and 200° C.,
d. wherein the melt viscosity at the curing temperature Tcur is less than 60 Pas
e. and curing at Tcur for a curing time less than 40 minutes.

13. Articles coated with a powder having a coating composition according to claim 1 , having a temperature sensitive substrate selected from the group consisting of MDF, wood, plastic, and metal alloys,
wherein the crosslinking density XLD is at least 0.01 mmol/ml and is

Assignees

• Allnex Netherlands Bv

Inventors

• Brinkhuis Richard Hendrikus Gerrit
• Watson Robert
• Bosma Martin
• Elfrink Petrus Johannes Maria David
• Buser Antonius Johannes Wilhelmus
• Yang Pengcheng
• Cavalieri Roberto
• Censi Massimiliano
• Chinellato Robertino
• Minesso Alessandro

Classifications

• C09D5/03 Primary

  Powdery paints · CPC title

• C08G18/4211

  derived from aromatic dicarboxylic acids and dialcohols · CPC title

• C08G18/606

  Polyester-amides · CPC title

• C08G18/6225

  Polymers of esters of acrylic or methacrylic acid · CPC title

• C08G18/73

  acyclic · CPC title