# US 10,766,844 B2 · Aromatic compounds bearing hydroxyl-substituted (per)fluoropolyether chains

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- Number: US 10,766,844 B2
- Document ID: US10766844B2
- Status: Granted
- Kind: B2
- Application number: 15/311,518
- Filed: 2015-05-14
- Published: 2017-03-23
- Granted: 2020-09-08
- Earliest claimed: 2014-05-16
- Assignees: Solvay Specialty Polymers Italy S.P.A.
- Applicants: Solvay Specialty Polymers Italy S.P.A.
- Inventors: Roberto Valsecchi; Pier Antonio Guarda; Rosaldo Picozzi
- Web page: https://patentgrep.com/patent/US10766844B2

## CPC

- C07C 43/23: containing hydroxy or O-metal groups
- C07C 43/1786: {containing halogen}
- C10M 105/54: containing carbon, hydrogen, halogen and oxygen
- C10M 105/56: containing nitrogen
- C10M 107/38: containing halogen
- C10M 131/08: containing carbon, hydrogen, halogen and oxygen
- C10M 131/10: Alcohols; Ethers; Aldehydes; Ketones
- G11B 5/7257: {Perfluoropolyether lubricant}
- C10M 2211/042: Alcohols; Ethers; Aldehydes; Ketones
- C10M 2219/087: containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10N 2040/18: in connection with recordings on magnetic tape or disc
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- G11B: INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER (recording measured values in a way that does not require playback through a transducer G01D9/00; recording or playback apparatus using mechanically marked tape, e.g. punched paper tape, or using unit records, e.g. punched or magnetically marked cards G06K; transferring data from one type of record carrier to another G06K1/18; circuits for coupling output of reproducer to radio receiver H04B1/20; gramophone pick-ups or like acoustic electromechanical transducers or circuits therefor H04R)
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

Compounds [compounds (L)] comprising at least one monocyclic, polycyclic or polycondensed aromatic moiety [moiety (A*)], wherein: at least one carbon atom of moiety (A*) is substituted with a fluoropolyoxyalkene chain [chain (Rf)], said chain (Rf) comprising: a) a fluorocarbon segment having ether linkages in the main chain and b) at least one hydroxyl group and wherein: at least one other carbon atom of moiety (A*) is substituted with an electron-withdrawing group and mixtures thereof are herein disclosed. Disclosed are also a process for manufacturing compounds (L), a method for lubricating MRM comprising using compounds (L), a lubricant composition comprising one or more compounds (L) and a method for manufacturing a composition (C).

## Claims

### Claim 1

A compound (L) comprising at least one moiety (A*) wherein moiety (A*) is selected from benzene, biphenyl and naphthalene, and wherein:
at least two carbon atoms of moiety (A*) are substituted with a fluoropolyoxyalkene chain (Rf), each chain (Rf) comprising:
a) a fluorocarbon segment having ether linkages in the main chain and
b) at least one hydroxyl group,
each chain (Rf) being bound to an sp2 carbon atom of said moiety (A*) through bridging group (B) comprising at least one heteroatom directly bound to said sp2 carbon atom, and wherein:
in moiety (A*), all carbon atoms which do not bear a chain (Rf) are substituted with a fluorine atom.

### Claim 2 (depends on 1)

A compound (L) according to claim 1 wherein chain (Rf) comprises repeating units R°, said repeating units being selected from:
(i) —CFXO—, wherein X is F or CF3,
(ii) —CFXCFXO—, wherein X, equal or different at each occurrence, is F or CF3, with the provision that at least one of X is F,
(iii) —CF2CF2CW2O—, wherein each of W, equal or different from each other, are F, Cl, 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 —ORf′T3, wherein Rf′ is a fluoropolyoxyalkene chain comprising a number of repeating units from 0 to 10, said recurring units being selected from: —CFXO—, —CF2CFXO—, —CF2CF2CF2O—, —CF2CF2CF2CF2O—, with each of each of X being independently F or CF3 and T3 being a C1-C3 perfluoroalkyl group.

### Claim 3 (depends on 2)

A compound (L) according to claim 2, wherein chain (Rf) complies with formula (Rf-I) here below:
—(CFX1O)g1(CFX2CFX3O)g2(CF2CF2CF2O)g3(CF2CF2CF2CF2O)g4— (Rf-I)
wherein:
X1, X2, X3 equal or different from each other and at each occurrence are independently —F, —CF3;
g1, g2, g3, and g4, equal or different from each other, are independently integers≥0, such that g1+g2+g3+g4 is in the range from 2 to 300; should at least two of g1, g2, g3 and g4 be different from zero, the different recurring units are generally statistically distributed along the chain.

### Claim 4 (depends on 1)

A compound (L) according to claim 1, wherein the compound is of formula:
wherein
A* is selected from benzene, biphenyl and naphthalene;
B is a bridging group (B) selected from a C1-C20 divalent alkylene group comprising at least one sulfur or oxygen atom directly bound to an sp2 carbon atom of moiety (A*), said group being optionally fluorinated and optionally containing one or more hydroxyl groups and from a group forming with moiety (A*) a condensed ring (R) comprising aromatic moiety (A*) and a non-aromatic cyclic moiety comprising two heteroatoms, each heteroatom being directly bound to an sp2 carbon atom of moiety (A*);
Rf is a divalent fluoropolyoxyalkene chain (Rf) wherein chain (Rf) comprises repeating units R°, said repeating units being chosen from:
(i) —CFXO—, wherein X is F or CF3,
(ii) —CFXCFXO—, wherein X, equal or different at each occurrence, is F or CF3, with the provision that at least one of X is —F,
(iii) —CF2CF2CW2O—, wherein each of W, equal or different from each other, are F, Cl, 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 —ORf′T3, wherein Rf′ is a fluoropolyoxyalkene chain comprising a number of repeating units from 0 to 10, said recurring units being selected from:
—CFXO—, —CF2CFXO—, —CF2CF2CF2O—, —CF2CF2CF2CF2O—, with each of each of X being independently F or CF3 and T3 being a C1-C3 perfluoroalkyl group;
Y is a hydrocarbon group, optionally fluorinated, which comprises at least one hydroxyl group;
G is a fluorine atom;
x is an integer of at least 2;
y is an integer of z−x, wherein z is the number of carbon atoms of moiety (A*), when bridging group (B) is a divalent alkylene group as defined above or z−2x, when bridging group (B) forms a condensed ring (R) as defined above, with the proviso that, when moiety (A*) is a polycyclic or polycondensed aromatic moiety, the number of bridging carbon atoms is to be detracted from z.

### Claim 5 (depends on 4)

A compound (L) according to claim 4 of formula (L-1*) below:
wherein x is an integer of at least 2, and n is 6−x.

### Claim 6 (depends on 5)

A compound (L) according to claim 5 wherein x is an integer ranging from 2 to 4.

### Claim 7 (depends on 6)

A compound (L) according to claim 6 which is selected from:
a compound (L-1*a), wherein B is —OCH2CF2O— and Y is —CF2CH2OH;
a compound (L-1*b), wherein B is —OCH2CH(OH)CH2OCH2CF2O— and Y is —CF2CH2OCH2CHOHCH2OH;
a compound (L-1*c), wherein B is —OCH2CF2O— and Y is —CF2CH2OCH2CHOHCH2OH;
a compound (L-1*d) wherein B is —OCH2CH(OH)CH2OCH2CF2O— and Y is —CF2CH2OH;
and wherein:
chain (Rf) complies with formula (Rf-III) below:
—O(CF2CF2O)a1(CF2O)a2— (Rf-III)
wherein:
a1, and a2 are integers>0 such that the number average molecular weight is between 400 and 10,000, with the ratio a2/a1 being comprised between 0.1 and 10, and
x ranges from 2 to 4 and n is 6−x.

### Claim 8 (depends on 1)

A process for the manufacture of a compound (L) according to claim 1, said process comprising the reaction of a perfluorinated monocyclic, polycyclic or polycondensed aromatic compound (A) with a (per)fluoropolyether (PFPE) polyol [PFPE (Ppol)].

### Claim 9 (depends on 1)

A lubricant composition for magnetic recording media (MRM), said composition comprising one or more compounds (L) as defined in claim 1 in admixture with further ingredients.

### Claim 10 (depends on 1)

A method of lubricating a magnetic recording media (MRM), said method comprising using one or more compounds (L) as defined in claim 1.

### Claim 11 (depends on 3)

A compound (L) according to claim 3, wherein g1+g2+g3+g4 is in the range from 2 to 100.

### Claim 12 (depends on 7)

A compound (L) according to claim 7, wherein a1, and a2 are integers>0 such that the number average molecular weight is between 400 and 5,000 and wherein the ratio a2/a1 is between 0.2 and 5.