Substrate including a surface coated with an epilame agent and method for coating such a substrate with epilame

Patent metadata

Field	Value
Publication number	US-10385155-B2
Application number	US-201715672510-A
Country	US
Kind code	B2
Filing date	Aug 9, 2017
Priority date	Sep 1, 2016
Publication date	Aug 20, 2019
Grant date	Aug 20, 2019

Abstract

The invention relates to a copolymer and a substrate having a surface, at least one part of which is coated with an epilame agent comprising at least one compound in the form of a copolymer comprising V units, N units, optionally at least one M unit, and optionally at least one P unit, linked by covalent bonds by their main chains, wherein

wherein W, X, Y, Z are spacer arms, T is a tracer group arranged to determine the concentration of epilame agent in an epilame-coating bath, L is a halogenated, preferably fluorinated, C 1 -C 20 carbon moiety, A is a substrate anchoring moiety, Q is H, CH 3 , or a hydrocarbon chain different from T.

The invention also concerns a method for coating such a substrate with epilame, said method comprising a step of checking the concentration of epilame agent in the epilame-coating bath by means of the tracer group and if necessary, a step of readjusting the concentration of epilame agent in the epilame-coating bath.

First claim

What is claimed is:

1. A copolymer comprising V units, N units, at least one M unit and optionally at least one P unit, linked by covalent bonds by their main chains, wherein

where R 1 , R 2 , R 3 , R 4 , which may be identical or different, are each selected from the group consisting of H, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkenyl group,
W, X, Y, Z, which may be identical or different, are spacer arms formed of a heteroatom or of a hydrocarbon chain that may contain at least one linear or branched heteroatom group comprising at least one carbon atom
T, which may be identical or different, is a tracer group arranged to determine the concentration of copolymer in a medium
L, which may be identical or different, is a halogenated C 1 -C 20 carbon moiety
A, which may be identical or different, forms an anchoring moiety for the substrate, and is chosen from the group consisting of thiols, thioethers, thioesters, sulphides, thioamides, silanols, alkoxysilanes, silane halides, hydroxyls, phosphates, protected or non-protected phosphonic acids, protected or non-protected phosphonates, amines, ammoniums, nitrogenated heterocycles, carboxylic acids, anhydrides, and catechol
Q, which may be identical or different, is selected from the group consisting of H, CH 3 , and a hydrocarbon chain that may contain at least one linear or branched, saturated or unsaturated heteroatom group, comprising at least 2 carbon atoms,
wherein the copolymer comprises, in molar percent, between 3% and 10% of V units, between 70% and 95% of N units, between 1% and 20% of M units, and between 0% and 20% of P units.

2. The copolymer according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , which may be identical or different, are H or CH 3 .

3. The copolymer according to claim 1 , wherein L, which may be identical or different, is a fluorinated C 1 -C 20 carbon moiety.

4. The copolymer according to claim 1 , wherein W, X, Y, Z, which may be identical or different, are selected from the group consisting of C 1 -C 20 ester groups, amide groups, and styrene derivative groups.

5. The copolymer according to claim 1 , wherein T, which may be identical or different, is a UV-absorbing group or a fluorophore.

6. The copolymer according to claim 1 , wherein T, which may be identical or different, is a UV-absorbing group derived from a compound selected from the group consisting of benzotriazoles, triazines, phenones, and acylphosphine oxides.

7. The copolymer according to claim 1 , wherein T, which may be identical or different, is a fluorophore moiety derived from a compound chosen from the group consisting of fluorescein, a naphtyl, anthracene, coumarin, rhodamine, and a fluorobenzoate.

8. The copolymer according to claim 1 , wherein L is a C 2 -C 20 carbon moiety.

9. The copolymer according to claim 8 , wherein L is a C 4 -C 20 carbon moiety.

10. The copolymer according to claim 1 , wherein L is an at least partially fluorinated moiety.

11. The copolymer according to claim 10 , wherein L is a completely fluorinated moiety.

12. The copolymer according to claim 1 , wherein the copolymer comprises between 10 and 350 units.

13. A method for coating with epilame at least one part of a substrate surface, the method comprising:
a) preparing an epilame-coating bath containing an epilame agent comprising at least one copolymer according to claim 1 ;
b) optionally, preparing the substrate surface;
c) monitoring the concentration of epilame agent in the epilame-coating bath by means of the tracer group;
d) optionally readjusting the concentration of epilame agent in the epilame-coating bath;
e) placing the substrate surface in contact with the epilame agent in the epilame-coating bath; and
f) drying.

14. The epilame-coating method according to claim 13 , wherein said epilame-coating method is continuous and wherein steps c) and d) are repeated over time.

15. The epilame-coating method according to claim 13 , wherein the preparation of the epilame agent is achieved by copolymerization of monomers capable of forming the V units with monomers capable of forming the N units, with monomers capable of forming at least one M unit and optionally with monomers capable of forming at least one P unit.

16. The epilame-coating method according to claim 13 , wherein after step e), the method also comprises a complementary cross-linking step g).

17. The epilame-coating method according to claim 13 , wherein the monomers are selected from the group consisting of acrylate, methacrylate, acrylamide, methacrylamide, vinyl and styrene monomers.

18. A method for coating with epilame at least one part of a substrate surface, the method comprising:
a) preparing an epilame-coating bath containing an epilame agent comprising at least one copolymer;
b) optionally, preparing the substrate surface;
c) monitoring the concentration of epilame agent in the epilame-coating bath by means of the tracer group;
d) optionally readjusting the concentration of epilame agent in the epilame-coating bath;
e) placing the substrate surface in contact with the epilame agent in the epilame-coating bath; and
f) drying,
wherein the copolymer comprises V units, N units, optionally at least one M unit and optionally at least one P unit, linked by covalent bonds by their main chains, wherein

where R 1 ,R 2 , R 3 , R 4 ,which may be identical or different, are each selected from the group consisting of H, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkenyl group,
W, X, Y, Z, which may be identical or different, are spacer arms formed of a heteroatom or of a hydrocarbon chain that may contain at least one linear or branched heteroatom group comprising at least one carbon atom
T, which may be identical or different, is a tracer group arranged to determine the concentration of copolymer in a medium
L, which may be identical or different, is a halogenated C 1 -C 20 carbon moiety
A, which may be identical or different, forms an anchoring moiety for the substrate, and is chosen from the group consisting of thiols, thioethers, thioesters, sulphides, thioamides, silanols, alkoxysilanes, silane halides, hydroxyls, phosphates, protected or non-protected phosphoric acids, protected or non-protected phosphonates, amines, ammoniums, nitrogenated heterocycles, carboxylic acids, anhydrides, and catechol
Q, which may be identical or different, is selected from the group consisting of H, CH 3 , and a hydrocarbon chain that may contain at least one linear or branched, saturated or unsaturated heteroatom group, comprising at least 2 carbon atoms.

19. The epilame-coating method according to claim 18 , wherein said epilame-coating method is continuous and wherein steps c) and d) are repeated over time.

20. The epilame-coating method according to claim 18 , wherein the preparation of the epilame agent is achieved by copolymerization of monomers capable of forming the V units with monomers capable of forming the N units, optionally with monomers capable of forming at least one M unit and optionally with monomers capable of forming at least one P unit.

21. The epilame-coating method according to claim 18 , wherein after step e), the method also comprises a complementary cross-link

Assignees

• Swatch Group Res & Dev Ltd

Inventors

• Letondor Christophe
• Rannoux Claire

Classifications

• C10N2040/06

  Instruments or other precision apparatus, e.g. damping fluids · CPC title

• C10N2030/26

  Waterproofing or water resistance · CPC title

• C10M2217/0245

  used as base material · CPC title

• C10M107/50

  containing silicon · CPC title

• C10M2221/025

  used as base material · CPC title