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1. (WO2019042678) NOVEL (PER)FLUOROPOLYETHER POLYMERS AND USE THEREOF
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Claims

Claim 1. A (per)fluoropolyether polymer [polymer (P)] comprising at least one (per)fluoropolyoxyalkylene chain [chain (RPf)] having two chain ends, wherein at least one of said chain ends bears at least one group of formula -B-(E)t, wherein:

t is an integer equal to or higher than 2, more preferably from 2 to 5, even more preferably from 2 to 3;

B is a group complying with the following formula (B-l):

wherein

R1 , R2 and R5, identical or different each other, are a linear or cyclic aliphatic group comprising 6 carbon atoms, optionally substituted with one or more linear or branched alkyl group having from 1 to 3 carbon atoms, or a

6-membered aromatic group, optionally substituted with one or more linear or branched alkyl group having from 1 to 3 carbon atoms,

R3 and R4 are each hydrogen atom or together they form a group of formula -C(=O)-,

n is an integer from 1 to 4, preferably from 1 to 2,

symbol (*) indicates the bond to said chain (RPf), and

each symbol (§) indicates the bond to said moiety E; and

E is a moiety of formula (E-l):

(E-l) -[OCH(CH3)CH2]z-Ru

wherein

z is in an integer from 1 to 15,

(Ru) is an unsaturated moiety.

Claim 2. The polymer (P) according to claim 1 , wherein said chain (RPf) is a chain of formula

-(CFX)ziO(Rf)(CFX')z2-D-0- wherein

z1 and z2, equal or different from each other, are equal to or higher than 1 , preferably from 1 to 10, more preferably from 1 to 3;

X and X', equal or different from each other, are -F or -CF3,

provided that when a and/or b are higher than 1 , X and X' are -F;

D is a hydrogenated alkylene chain comprising from 1 to 6 and even more preferably from 1 to 3 carbon atoms, said alkyl chain being optionally substituted with at least one perfluoroalkyl group comprising from 1 to 3 carbon atoms;

(Rf) comprises, preferably consists of, repeating units R°, said repeating units being independently selected from the group consisting of:

(i) -CFXO-, wherein X is F or CF3;

(ii) -CFXCFXO-, wherein X, equal or different at each occurrence, is F or CF3, with the proviso that at least one of X is -F;

(iii) -CF2CF2CW2O-, wherein each of W, equal or different from each other, are F, CI, H;

(iv) -CF2CF2CF2CF2O-;

(v) -(CF2)j-CFZ-O- wherein j is an integer from 0 to 3 and Z is a group of general formula -O-R(f-a)-T, wherein R(f-a) is a fluoropolyoxyalkene chain comprising a number of repeating units from 0 to 10, said recurring units being chosen among the following : -CFXO- , -CF2CFXO-, -CF2CF2CF2O-,

-CF2CF2CF2CF2O-, with each of each of X being independently F or CF3 and T being a C1-C3 perfluoroalkyl group.

Claim 3. The polymer (P) according to claim 1 , wherein said moiety (Ru) is selected in the group consisting of:

(Ru-I) -O-C(=O)-CRH=CH2

(Ru-ll) -O-C(=O)-NH-CO-CRH=CH2

wherein

RH is H or a linear or branched Ci-C6 alkyl group; more preferably H or a I or branched Ci-C3 alkyl group.

Clainn 4. The polymer (P) according to claim 1 , wherein said group (B) complies with the following formulae (B-l-i) to (B-l-v):


wherein

symbol (*) indicates the bond to said chain (RPf) and

each of symbols (§) indicates the bond to a group of formula (E-l).

Claim 5. The polymer (P) according to any one of the preceding claims, wherein said polymer (P) complies with the following formula (P-l):

(P-l) T-(Rpf)-B-[(E-l)]t

wherein

(RPf), (B), (E-l) and t are as defined above and

T is a neutral group selected from: -H, -F, -CI and linear or branched

perfluoroalkyl group comprising from 1 to 3 carbon atoms; or a group of formula (T-l):

(T-l)

wherein

B and (E-l) have the same meanings defined in claim 1 ,

D* has the same meanings defined for D in claim 2, and

t* has the same meanings defined for t in claim 1.

Claim 6. A process for the synthesis of polymer (P) as defined in any one of claims 1 to 5 , said process comprising the following steps:

(I) contacting at least one poli-isocyanate compound [compound (NCO)] with at least one compound [compound (U)] of formula

H-[OCH(CH3)CH2]z-Ru

wherein Ru is an unsaturated moiety and z is an integer from 1 to 15, wherein the ratio between the equivalents of said compound (NCO) and of said compound (U) is higher than 1 ;

(II) contacting the compound obtained in step (I) with at least one

(per)fluoropolyether polymer [polymer (PFPE-OH)] comprising a

(per)fluoropolyoxyalkylene chain having two chain ends, wherein at least one of said chain ends comprises a hydroxy group, thus obtaining said polymer (P).

Claim 7. The process according to claim 6, wherein said compound (NCO) is obtained from the reaction of at least three molecules of the same diisocyanate compound, which react together to form a linear or cyclic molecule comprising at least three isocyanate groups; said diisocyanate compound being preferably selected in the group comprising, more preferably consisting of:

hexamethylene diisocyanate (HDI); isophorone diisocyanate (IPDI); xylylene diisocyanate; hydrogenated xylylene diisocyanate; isomers of methylene- bis(cyclohexyl isocyanate) [also referred to as hydrogenated MDI] and mixtures thereof; isomers of toluene diisocyanate (TDI), such as 2,4-TDI and 2,6-TDI, and mixtures thereof; isomers of methylene diphenyl

diisocyanate (MDI) such as 2,2'-MDI, 2,4'-MDI and 4,4'-MDI and mixtures

thereof; toluidine diisocyanate; and naphthalene diisocyanate.

Claim 8. The process according to claim 7, wherein said compound (NCO) comprises at least three isocyanate groups, more preferably from 3 or 4 isocyanate groups.

Claim 9. The process according to any one of claims 6 to 8, wherein said compound (NCO) comprising three isocyanate groups are represented by the following formulae (I) to (IV):

and wherein said compound (NCO) comprising four isocyanate groups are represented by the following formula (V):

Claim 10. The process according to claim 6, wherein the equivalent ratio

between said compound (NCO) and said compound (U) is from 1.1 to 2, more preferably from 1.2 to 1.8.

Claim 1 1. The process according to claim 6, wherein said step (II) is performed in the presence of a fluorinated solvent, preferably selected in the group comprising: fluorinated hydrocarbons, hexafluoroxylene, chlorotrifluoro- toluene, trifluorotoluene, hexafluorobenzene and mixtures thereof.

Claim 12. A composition [composition (C)] comprising at least one polymer (P) as defined in any one of claims 1 to 5 and at least one solvent, said solvent being preferably selected in the group comprising: ketones for instance methylethylketone (MEK), methylisobutylketone (MIBK); esters for instance ethyl acetate, butyl acetate, isobutyl acetate; organic solvents containing in the molecule an ester-ether group such as polyoxyethylene monoethyl-ether acetate, polyoxyethylene monobutylether acetate, polyoxy butylene monoethyl-ether acetate, polyoxy-butylene monobutylether acetate, polyoxyethylene diacetate, polyoxybutylene-diacetate, 2-ethoxy ethylacetate, ethyleneglycol diacetate, butyleneglycol diacetate; and mixtures thereof.

Claim 13. The composition (C) according to claim 12, said composition (C) further comprising at least one UV-curable component, such that the amount of said polymer (P) in said composition (C) is from 0.01 to 8 wt.%, more preferably from 0.5 to 5 wt.%, based on the total weight of said

composition (C).

Claim 14. A method for providing a transparent coating onto at least one surface of a plastic substrate, said method comprising:

(i) providing at least one plastic substrate having at least one surface, said plastic substrate being preferably selected in the group comprising, preferably consisting of: polyethylene terephthalate (PET), polycarbonate (PC), polyvinyl chloride (PVC), thermoplastic olefin (TPO), thermoplastic polyurethane (TPU), polypropylene (PP), acrylonitrile butadiene styrene (ABS) and

polyamides (PA);

(ii) contacting said at least one surface with polymer (P) as defined in any one of claims 1 to 5 or with composition (C) as defined in any one of claims 12 and 13; and

(iii) curing said polymer (P) or said composition (C) onto said at least one surface.

Claim 15. Use of said composition (C) as defined in any one of claims 12

and 13 or of said polymer (P) as defined in any one of claims 1 to 5, for providing a transparent coating onto at least one surface of a plastic substrate, said plastic substrate being preferably selected in the group comprising, preferably consisting of: polyethylene terephthalate (PET), polycarbonate (PC), polyvinyl chloride (PVC), thermoplastic olefin (TPO), thermoplastic

polyurethane (TPU), polypropylene (PP), acrylonitrile butadiene styrene (ABS) and polyamides (PA).