Powder coating composition

Patent metadata

Field	Value
Publication number	US-12577409-B2
Application number	US-202418425558-A
Country	US
Kind code	B2
Filing date	Jan 29, 2024
Priority date	Jan 26, 2018
Publication date	Mar 17, 2026
Grant date	Mar 17, 2026

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, wherein the one or more crosslinkable components are crosslinkable by Real Michael Addition (RMA) reaction, and the powder coating composition comprises
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 with a delay at a curing temperature of at least 80° C. and below 200° C., wherein the catalyst system C is a latent catalyst system LCC having chemical latency comprising components that react at the curing temperature to initiate the reaction between crosslinkable components A and B with a delay, said latent catalytic system LCC comprising embodiment LCC2:
a) a weak base C2 that is a Michael addition donor S2, and
b) an activator C1 that is a Michael acceptor S1 comprising an activated unsaturated group C═C reactive with S2 at the curing temperature,
c) optionally further comprising an acid C3 being an acid S3 of which the corresponding base also is a Michael addition donor, or a protonated S2,
wherein
in case S1 is an acrylate, S2 has a pKa of the conjugated acid below 8, wherein pKa is defined as the value in an aqueous environment, and
in case S1 is a methacrylate, fumarate, itaconate or maleate, S2 has a pKa of the conjugated acid below 10.5, and
wherein the powder coating composition has 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, 90, 100 and 200, 150, 135 or 120° 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, and with the time to reach 20% conversion at 100° C. is at least 1 minute.

2 . The powder coating composition according to claim 1 , wherein in latent catalyst system embodiment LCC2
the weak base S2 is selected from the group consisting of phosphines, N-alkylimidazoles and fluorides or is a weak base nucleophile anion X-from an acidic X-H group containing compound wherein X is N, P, O, S or C, wherein anion X- is a Michael Addition donor reactive with activator S1 and anion X- is characterized by a pKa of the corresponding conjugate acid X—H of less than 8 and more than 1 units lower than the pKa of the acidic C—H groups of majority component A, and the latent catalyst system comprises acid S3 having a pKa of more than 1 units lower than the pKa of the acidic C—H groups of majority component A, or wherein acid S3 is a protonated S2.

3 . The powder coating composition according to claim 1 , wherein weak base C2 is added as a salt comprising a cation that is not acidic, or a 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 possibly linked to a polymer.

4 . The powder coating composition according to claim 1 , comprising
a. in 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 LCC, c. optionally an acid C3 in an amount between 1 and 500 μeq/gr, 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 ,
a. wherein the weak base C2 represents between 10 and 100 mol % of the sum of C2 and C3, or b. the amount of acid C3 is 20-400 mol % of the amount of C2, or c. wherein the ratio of the molar amount of C1 to the sum of the amount of C2 and C3 is at least 0.5, and at most 3 or d. the ratio of C1 to C3 is at least 1.

6 . The powder coating composition according to claim 1 wherein
a. crosslinkable component A comprises at least 2 acidic C—H donor groups in activated methylene or methine in a structure Z1 (—C(—H) (-R)-) Z2 wherein R is hydrogen, a hydrocarbon, an oligomer or a polymer, and wherein Z1 and Z2 are the same or different electron-withdrawing groups selected from keto, ester or cyano or aryl groups, and comprises an activated C—H derivative having a structure according to formula 1:

wherein R is hydrogen or an optionally substituted alkyl or aryl and Y and Y′ are identical or different substituent groups selected from alkyl, aralkyl or aryl, or alkoxy or wherein in formula 1 the —C (═O)-Y and/or —C (═O)-Y′ is replaced by CN or aryl, with no more than one aryl or wherein Y or Y′ can be NRR′, and R and R′ are H or optionally substituted alkyl, wherein R, Y or Y′ optionally provide connection to an oligomer or polymer, said component A providing at least 50% of the total of C—H acidic groups in crosslinkable component A,
b. Component B comprising the at least 2 activated unsaturated RMA acceptor groups originate from acryloyl, methacryloyl, itaconates, maleate or fumarate functional groups,
wherein at least one of components A or B is a polymer and
wherein the composition comprises a total amount of donor groups C—H and acceptor groups C═C per gram binder solids of 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.

7 . The powder coating composition according to claim 1 , wherein at least one of crosslinkable components A or B or a hybrid A/B is a polymer, 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, or g) has a Tg above 25° Cas 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.

8 . 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 (semi-) crystalline state in the powder and have a melting temperature between 40 and 130° C.

9 . The powder coating composition according to claim 1 wherein component B is 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.

10 . A process for the preparation of a powder coating composition according to claim 1 , comprising the step of
a. Providing component A

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

• C08L2312/00

  Crosslinking · CPC title

• C08L75/06

  from polyesters · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08K5/105

  with phenols · CPC title