Removable coating systems and methods

Patent metadata

Field	Value
Publication number	US-11033482-B2
Application number	US-201515524048-A
Country	US
Kind code	B2
Filing date	Nov 6, 2015
Priority date	Nov 7, 2014
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

Disclosed herein are coating compositions that may include at least one urethane (meth)acrylate oligomer having a molecular weight between about 2,000 g/mol and about 50,000 g/mol and at least one cycloaliphatic (meth)acrylate. The coating compositions may also optionally include at least one photo-initiator, adhesion promoter, pigment, dye and/or plasticizer. The coating compositions may be hardened, after application, by curing by exposure to radiant energy, by exposure to electron beam radiation, by exposure to heat, by exposure to chemicals and combinations thereof. Upon hardening, the coating composition typically has two phases, a soft phase which has a Tg between −50° C. and 0° C. and a hard phase which has a Tg between 60° C. and 120° C. Methods of using the coating compositions are also described.

First claim

The invention claimed is:

1. A coating composition comprising:
a) at least one urethane (meth)acrylate oligomer of formula (I)

wherein 2≤n≤20 and 2≤m≤4;
R1 is selected from the group consisting of alkylene, cycloalkylene, arylene, arylkylene and combinations thereof;
R2 is selected from the group consisting of alkylenes, cycloalkylenes and arylalkylenes;
R3 comprises a moiety of —R4-OH, wherein the oligomer a) has a mean free OH value of about 2 mg KOH/g to about 50 mg KOH/g and R3 comprises a moiety of —R5-(meth)acryloyl;
R4 and R5 being a bivalent radical selected from the group consisting of alkylenes, cycloalkylenes and arylalkylenes, with R4 and R5 being identical or different from each other; and
wherein the at least one urethane (meth)acrylate oligomer has a number average molecular weight Mn measured by GPC, of from about 2,000 g/mol to about 50,000 g/mol and wherein the at least one urethane (meth)acrylate oligomer a) has an average in number-functionality of from about 1.1 to about 1.9 (meth)acrylates;
b) at least one cycloaliphatic (meth)acrylate; and
c) optionally, at least one allylic compound from allylic monomers and/or oligomers bearing at least one allylic group,
d) optionally, at least one component selected from the group of additives consisting of an adhesion promoter, a photo-initiator, a thiol compound, a pigment, a dye, a plasticizer and combinations thereof.

2. The coating composition of claim 1 , wherein the said composition is curable.

3. The coating composition of claim 1 , wherein the coating composition comprises less than 1% by weight of non-reactive solvent and less than 1% by weight of non-reactive, solvent-dissolvable polymer.

4. The coating composition of claim 1 , wherein the coating composition comprises an adhesion promoter that includes one or more functional groups selected from the group consisting of hydroxyl groups, carboxylic acids, phosphoric acids and combinations thereof.

5. The coating composition of claim 4 , wherein the adhesion promoter is selected from the group consisting of hydroxylethyl (meth)acrylate, hydroxylpropyl (meth)acrylates, pyromellitic dianhydride dialkyl(meth)acrylate, phathalic acid monoalkyl (meth)acrylates, succinic acid monoalkyl (meth)acrylates, phosphoric acid or phosphoric ester functional (meth)acrylates and carboxylic acid functional (meth)acrylates and combinations thereof.

6. The coating composition of claim 1 , wherein said composition further comprises an allylic compound c) bearing at least one allylic group and optionally a metal ion catalyst.

7. The coating composition of claim 2 , wherein the coating composition comprises a photo-initiator selected from the group consisting of α-hydroxyketones, phenylglyoxylates, benzyldimethylketals, α-aminoketones, mono-acyl phosphines, bis-acyl phosphines, phosphine oxides and metallocenes and combinations thereof.

8. The coating composition of claim 1 , wherein the cycloaliphatic (meth)acrylate b) comprises a (meth)acrylate monomer bearing at least one mono-, bi- or tri-cyclic group.

9. The coating composition of claim 1 , wherein the cycloaliphatic (meth)acrylate b) is selected from the group consisting of 3,3,5-Trimethycyclohexyl acrylate, tricyclodecane dimethanol (meth)acrylate, (alkoxylated) isobornyl (meth)acrylate, (alkoxylated) isophoryl (meth)acrylate, (alkoxylated) trimethylolpropane cyclic formal (meth)acrylate, (alkoxylated) tertiobutylcyclohexyl (meth)acrylate, (alkoxylated) tetrahydrofurfuryl (meth)acrylate, (alkoxylated) dicyclopentadiene (alkoxylated) (meth)acrylate, (alkoxylated) tricyclodecane dimethanol (meth)acrylate, (alkoxylated) cyclohexane dimethanol (meth)acrylate, (alkoxylated) (di)cyclopentenyl (meth)acrylate, (alkoxylated) cyclohexyl (meth)acrylate, (alkoxylated) norbornyl (meth)acrylate, (alkoxylated) (meth)acrylate based on rosin (hydroxyalkyl (meth)acrylate ester with abietic acid) and combinations thereof.

10. The coating composition of claim 1 , wherein the cycloaliphatic (meth)acrylate b) is present from 20% to about 80% by weight of the coating composition.

11. The coating composition of claim 1 , wherein the cured coating has two phases, a soft phase which has a Tg between −50° C. and 0° C. and a hard phase which has a Tg between 60° C. and 120° C.

12. The coating composition of claim 1 , wherein the at least one urethane (meth)acrylate oligomer a) has a molecular weight Mn of from about 3,000 g/mol to about 25,000 g/mol.

13. The coating composition of claim 1 , wherein 3≤n≤10.

14. A coating composition comprising:
a) at least one urethane (meth)acrylate oligomer of formula (I)

wherein 2≤n≤20 and 2≤m≤4;
R1 is selected from the group consisting of alkylene, cycloalkylene, arylene, aralkylene and combinations thereof;
R2 is selected from the group consisting of alkylenes, cycloalkylenes, arylalkylenes and combinations thereof;
R3 comprises a moiety of —R4-OH, wherein the oligomer a) has a mean free OH value of about 2 mg KOH/g to about 50 mg KOH/g and R3 comprises a moiety of —R5-(meth)acryloyl;
R4 and R5 being a bivalent radical selected from the group consisting of alkylenes, cycloalkylenes and arylalkylenes, with R4 and R5 being identical or different from each other; and
wherein the at least one urethane (meth)acrylate oligomer has a molecular weight of from about 2,000 g/mol to about 50,000 g/mol and wherein the at least one urethane (meth)acrylate oligomer
a) has an average in number-functionality of from about 1.1 to about 1.9 (meth)acrylates;
b) at least one cycloaliphatic (meth)acrylate; and
c) optionally, at least one allylic compound from allylic monomers and/or oligomers bearing at least one allylic group,
d) optionally, at least one component selected from the group consisting of an adhesion promoter, a photo-initiator, a pigment, a dye, a plasticizer and combinations thereof; and
wherein the coating composition comprises less than 1% by weight of non-reactive solvent and less than 1% by weight of non-reactive, solvent-dissolvable polymer and the coating after curing has two phases, a soft phase which has a Tg between −50° C. and 0° C. and a hard phase which has a Tg between 60° C. and 120° C.

15. The coating composition of claim 14 , wherein the composition is curable.

16. The coating composition of claim 14 , wherein said composition comprises an allylic compound c) bearing at least one allylic group.

17. A method of coating a nail with the composition of claim 1 , comprising:
applying the coating composition to a nail and
hardening (curing) the coating composition.

18. The method of claim 17 , wherein the hardening (curing) comprises curing the coating composition by exposure to radiant (radiation) energy, by exposure to electron beam radiation, by exposure to heat, by exposure to chemicals or combinations thereof.

19. The coating composition of claim 1 , wherein it is suitable for nail cosmetics.

20. The coating composition of claim 1 , suitable for nail coatings.

21. A coating resulting from curing (hardening) the coating composition of claim 1 .

22. The coating of claim 21 , wherein it is a cosmetic or a nail coating.

Assignees

• Arkema France

Inventors

• Lu Jin
• Wu Jinping
• Dong Xiaoxing

Classifications

• A61Q3/02 Primary

  Nail coatings · CPC title

• C08G18/4238

  derived from dicarboxylic acids and dialcohols · CPC title

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08G18/227

  of antimony, bismuth or arsenic · CPC title

• C08G18/672 Primary

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title