IP Library Granted Patent US 9,550,954
Granted Patent B2
US 9,550,954 · App. 13/989,549 · Granted Jan 24, 2017

Triazine derivative

Inventors: Roberto Valsecchi (Osio Sopra, IT); Fabrizio Mutta (Fin Mornasco, IT); Claudio Adolfo Pietro Tonelli (Monza, IT)
Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
C10M133/42C08G65/00C08G65/007C08G65/33317C10M2213/0606C10M2215/2225
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Quick Facts
Patent No.
US 9,550,954
App. No.
13/989,549
Granted
Jan 24, 2017
Kind
B2
Abstract

The invention pertains to certain (per)fluoropolyether triazine derivatives comprising at least one triazine group and at least one fluoropolyoxyalkene chain (chain R f ) comprising a fluorocarbon segment having ether linkages in main chain, said chain R f comprising at least one hydroxyl group, to a method for their manufacture and to their use in lubrication, in particular for lubricating sliding or moving parts of magnetic recording media.

Claims (120)

1. A triazine derivative of formula (T-1) or formula (T-2):

wherein:

each of Y, Y′, Y″, Y°, Y°′, Y°″, Y°′″, Y°″″ equal to or different from each other, is independently a hydrocarbon group, optionally fluorinated, wherein at least one of Y, Y′, Y″ in formula (T-1) and at least one of Y°, Y°′, Y°″, Y°′″, Y°″″ in formula (T-2) is selected from the group consisting of:

groups of formula —CF 2 CH 2 O(CH 2 CH 2 O) s′ H and —CF 2 CF 2 CH 2 O(CH 2 CH 2 O) s″ H, wherein s′ and s″, equal to or different from each other and at each occurrence, are integers from 0 to 5; and

groups of formula —CF 2 CH 2 O(CH 2 CH 2 O) w′ J′(OH) e′ and —F 2 CF 2 CH 2 O(CH 2 CH 2 O) w″ J″(OH) e″ , wherein w′ and w″, equal to or different from each other and at each occurrence, are integers from 0 to 5, J′ and J″ are C 1 -C 12 hydrocarbon bridging group, optionally comprising ethereal bonds; and e′ and e″ are integers from 2 to 4;

each of R F , R′ F , R″ F , R° F , R°′ F , R°″ F , R°′″ F , R°″″ F , R°* F , R°** F , equal to or different from each other, is independently a divalent fluoropolyoxyalkene chain (R f ) comprising repeating units R°, said repeating units selected from the group consisting of:

(i) —CFXO—, wherein X is F or CF 3 ,

(ii) —CFXCFXO—, wherein X, equal to or different at each occurrence, is F or CF 3 , wherein at least one of X is —F,

(iii) —CF 2 CF 2 CW 2 O—, wherein each of W, equal to or different from each other, are selected from F, Cl, and H,

(iv) —CF 2 CF 2 CF 2 CF 2 O—, and

(v) —(CF 2 ) j —CFZ—O—wherein j is an integer from 0 to 3 and Z is a group of general formula —OR f ′T 3 , wherein R f ′ is a fluoropolyoxyalkene chain comprising between 0 and 10 repeating units each independently selected from the group consisting of —CFXO—, —CF 2 CFXO—, —CF 2 CF 2 CF 2 O—, and —CF 2 CF 2 CF 2 CF 2 O—, with each of X being independently F or CF 3 , and wherein T 3 is a C 1 —C 3 perfluoroalkyl group;

each of E, E′, E″, E°, E°′, E°″, E°′″, E°″″, E°*, E°**, E°***, E°****, equal to or different from each other, is independently a bond or a C 1 -C 20 divalent bridging group, optionally comprising heteroatoms, optionally fluorinated, optionally further comprising one or more than one hydroxyl group; and

n in formula (T-2) is zero or an integer from 1 to 5.

2. The triazine derivative of claim 1 , wherein said at least one of Y, Y′, Y″ in formula (T-1) and said at least one of Y°, Y°′, Y°″, Y°′″, Y°″″ in formula (T-2) is selected from the group consisting of:

groups of formula —CF 2 CH 2 OH and CF 2 CF 2 CH 2 OH; and

groups of formula —CF 2 CH 2 O(CH 2 CHOHCH 2 O) d′ H and —CF 2 CF 2 CH 2 O(CH 2 CHOHCH 2 O) d″ H, wherein d′ and d″, equal to or different from each other and at each occurrence, are integers from 1 to 3.

3. The triazine derivative of claim 2 , complying with any of formula (T-1a) and (T-2a) herein below:

wherein:

each of n1, n2, n1′, n2′, n1″, n2″, n1#, n2#, n1*, n2*, n1′*, n2′*, n1″*, n2″*, n1′″*, n2′″*, equal to or different from each other, is independently an integer from 0 to 5

each of f1, f2, f1′, f2′, f1″, f2″, f1*, f2*, f1′*, f2′*, f1″*, f2″*, f1′″*, f2′″*, f1#, f2#, equal to or different from each other, is independently an integer of 1 to 2;

each of R F , equal to or different from each other and at each occurrence, is independently a divalent fluoropolyoxyalkene chain (R f ); and

each of G, G′, G″, G*, G′*, G″*, G′″*, equal to or different from each other, is independently a hydroxyl-containing group,

wherein said R f is a chain comprising repeating units R°, said repeating units selected from the group consisting of:

—CFXO—,  (i)

wherein X is F or CF 3 ,

—CFXCFXO—,  (ii)

wherein X, equal to or different at each occurrence, is F or CF 3 , wherein at least one of X is —F,

—CF 2 CF 2 CW 2 O—,  (iii)

wherein each of W, equal to or different from each other, are F, Cl, and H,

—CF 2 CF 2 CF 2 CF 2 O—,  (iv)

and

—(CF 2 ) j —CFZ—O—,  (v)

wherein j is an integer from 0 to 3 and Z is a group of general formula —OR f ′T 3 , wherein R f ′ is a fluoropolyoxyalkene chain comprising between 0 and 10 repeating units each independently selected from the group consisting of —CFXO—, —CF 2 CFXO—, —CF 2 CF 2 CF 2 O—, and —CF 2 CF 2 CF 2 CF 2 O—, with each of X being independently F or CF 3 , and wherein T 3 is a C 1 -C 3 perfluoroalkyl group.

4. The triazine derivative of claim 2 , complying with any of formula (T-1b) and (T-2b) herein below:

wherein:

each of n2, n2′, n2″, n2#, n2*, n2′*, n2″*, n2′″*, equal to or different from each other, is independently an integer from 0 to 5;

each of f1, f2, f1′, f2′, f1″, f2″, f1*, f2*, f1′*, f2′*, f1″*, f2″*, f1′″*, f2′″*, f1#, f2#, equal to or different from each other, is independently an integer of 1 to 2;

each of R F , equal to or different from each other and at each occurrence, is independently a divalent fluoropolyoxyalkene chain (R f );

each of R H , equal to or different from each other and at each occurrence, is independently a hydrogen atom, a C 1 -C 6 alkyl group or a (chain R f )—C(O)— group, in which chain (R f ) is a fluoropolyoxyalkylene chain containing at least one hydroxyl group; and

each of G, G′, G″, G*, G′*, G″*, G′″*, equal to or different from each other, is independently a hydroxyl-containing group,

wherein said R f is a chain comprising repeating units R°, said repeating units selected from the group consisting of:

—CFXO—,  (i)

wherein X is F or CF 3 ,

—CFXCFXO—,  (ii)

wherein X, equal to or different at each occurrence, is F or CF 3 , wherein at least one of X is —F,

—CF 2 CF 2 CW 2 O—,  (iii)

wherein each of W, equal to or different from each other, are F, Cl, and H,

—CF 2 CF 2 CF 2 CF 2 O—,  (iv)

and

—(CF 2 ) j —CFZ—O—,  (v)

wherein j is an integer from 0 to 3 and Z is a group of general formula —OR f ′T 3 , wherein R f ′ is a fluoropolyoxyalkene chain comprising between 0 and 10 repeating units each independently selected from the group consisting of —CFXO—, —CF 2 CFXO—, —CF 2 CF 2 CF 2 O—, and —CF 2 CF 2 CF 2 CF 2 O—, with each of X being independently F or CF 3 , and wherein T 3 is a C 1 -C 3 perfluoroalkyl group.

5. The triazine derivative of claim 4 wherein each of R H , equal to or different from each other and at each occurrence, is independently a group complying with formula —CO—(CF 2 ) f1 a —R F a —(CF 2 ) f2 a —CH 2 —(OCH 2 CH 2 ) n2 a -G a , wherein n2 a is an integer of 0 to 5 0; each of f1 a and f2 a is independently an integer of 1 or 2; R F a is a divalent difluoropolyoxyalkylene chain (R f ) and G a is a hydroxyl-containing group, wherein said R f is a chain comprising repeating units R°, said repeating units is selected from the group consisting of:

—CFXO—,  (i)

wherein X is F or CF 3 ,

—CFXCFXO—,  (ii)

wherein X, equal to or different at each occurrence, is F or CF 3 , wherein at least one of X is —F,

—CF 2 CF 2 CW 2 O—,  (iii)

wherein each of W, equal to or different from each other, are F, Cl, and H,

—CF 2 CF 2 CF 2 CF 2 O—,  (iv)

and

—(CF 2 ) j —CFZ—O—,  (v)

wherein j is an integer from 0 to 3 and Z is a group of general formula —OR f ′T 3 , wherein R f ′ is a fluoropolyoxyalkene chain comprising between 0 and 10 repeating units each independently selected from the group consisting of —CFXO—, —CF 2 CFXO—, —CF 2 CF 2 CF 2 O—, and —CF 2 CF 2 CF 2 CF 2 O—, with each of X being independently F or CF 3 , and wherein T 3 is a C 1 -C 3 perfluoroalkyl group.

6. The triazine derivative of claim 2 complying with any of formula (T-1c) and (T-2c) herein below:

wherein:

each of n2, n2′, n2″, n2#, n2*, n2′*, n2″*, n2′″*, equal to or different from each other, is independently an integer from 0 to 5;

each of f1, f2, f1′, f2′, f1″, f2″, f1*, f2*, f1′*, f2′*, f1″*, f2″*, f1′″*, f2′″*, f1#, f2#, equal to or different from each other, is independently an integer of 1 to 2;

u is 0 or 1;

each of R F , equal to or different from each other and at each occurrence, is independently a divalent fluoropolyoxyalkene chain (R f );

each of R H , equal to or different from each other and at each occurrence, is independently a hydrogen atom, a C 1 -C 6 alkyl group or a group of formula (chain R f )—CF 2 (CH 2 O) u CH 2 — or of formula (chain R f )—CF 2 CF 2 (CH 2 O) u CH 2 —, wherein said chain R f is a fluoropolyoxyalkylene chain containing at least one hydroxyl group;

each of G, G′, G″, G*, G′*, G″*, G′″*, equal to or different from each other, is independently a hydroxyl-containing group,

wherein said R f is a chain comprising repeating units R°, said repeating units selected from the group consisting of:

—CFXO—,  (i)

wherein X is F or CF 3 ,

—CFXCFXO—,  (ii)

wherein X, equal to or different at each occurrence, is F or CF 3 , wherein at least one of X is —F,

—CF 2 CF 2 CW 2 O—,  (iii)

wherein each of W, equal to or different from each other, are F, Cl, and H,

—CF 2 CF 2 CF 2 CF 2 O—,  (iv)

and

—(CF 2 ) j —CFZ—O—,  (v)

wherein j is an integer from 0 to 3 and Z is a group of general formula —OR f ′T 3 , wherein R f ′ is a fluoropolyoxyalkene chain comprising between 0 and 10 repeating units each independently selected from the group consisting of —CFXO—, —CF 2 CFXO—, —CF 2 CF 2 CF 2 O—, and —CF 2 CF 2 CF 2 CF 2 O—, with each of X being independently F or CF 3 , and wherein T 3 is a C 1 -C 3 perfluoroalkyl group.

7. The triazine derivative of claim 6 wherein each of R H , equal to or different from each other and at each occurrence, is a group of formula —CH 2 —(OCH 2 ) u —(CF 2 ) f1 a —R F a —(CF 2 ) f2 a —CH 2 —(OCH 2 CH 2 ) f2 a -G a , wherein u is 0 or 1, n2 a is an integer of 0 to; each of f1 a and f2 a is independently an integer of 1 or 2; R F a is a divalent fluoropolyoxyalkylene chain (R f ) and G a is a hydroxyl-containing group,

wherein said R f is a chain comprising repeating units R°, said repeating units selected from the group consisting of:

—CFXO—,  (i)

wherein X is F or CF 3 ,

—CFXCFXO—,  (ii)

wherein X, equal to or different at each occurrence, is F or CF 3 , wherein at least one of X is —F,

—CF 2 CF 2 CW 2 O—,  (iii)

wherein each of W, equal to or different from each other, are F, Cl, and H,

—CF 2 CF 2 CF 2 CF 2 O—,  (iv)

and

—(CF 2 ) j —CFZ—O—,  (v)

wherein j is an integer from 0 to 3 and Z is a group of general formula —OR f ′T 3 , wherein R f ′ is a fluoropolyoxyalkene chain comprising between 0 and 10 repeating units each independently selected from the group consisting of —CFXO—, —CF 2 CFXO—, —CF 2 CF 2 CF 2 O—, and —CF 2 CF 2 CF 2 CF 2 O—, with each of X being independently F or CF 3 , and wherein T 3 is a C 1 -C 3 perfluoroalkyl group.

8. The triazine derivative of claim 2 , complying with any of formula (T-1d) and (T-2d) herein below:

wherein:

each of n2, n2′, n2″, n2#, n2*, n2′*, n2″*, n2′″*, equal to or different from each other, is independently an integer from 0 to 5;

each of f1, f2, f1′, f2′, f1″, f2″, f1*, f2*, f1′*, f2′*, f1″*, f2″*, f1′″*, f2′″*, f1#, f2#, equal to or different from each other, is independently an integer of 1 to 2;

each of R F , equal to or different from each other and at each occurrence, is independently a divalent fluoropolyoxyalkene chain (R f ); and

each of G, G′, G″, G*, G′*, G″*, G′″*, equal to or different from each other, is independently a hydroxyl-containing group,

wherein said R f is a chain comprising repeating units R°, said repeating units is selected from the group consisting of:

—CFXO—,  (i)

wherein X is F or CF 3 ,

—CFXCFXO—,  (ii)

wherein X, equal to or different at each occurrence, is F or CF 3 , wherein at least one of X is —F,

—CF 2 CF 2 CW 2 O—,  (iii)

wherein each of W, equal to or different from each other, are F, Cl, and H,

—CF 2 CF 2 CF 2 CF 2 O—,  (iv)

and

—(CF 2 ) j —CFZ—O—,  (v)

wherein j is an integer from 0 to 3 and Z is a group of general formula —OR f ′T 3 , wherein R f ′ is a fluoropolyoxyalkene chain comprising between 0 and 10 repeating units each independently selected from the group consisting of —CFXO—, —CF 2 CFXO—, —CF 2 CF 2 CF 2 O—, and —CF 2 CF 2 CF 2 CF 2 O—, with each of X being independently F or CF 3 , and wherein T 3 is a C 1 -C 3 perfluoroalkyl group.

9. A lubricant composition comprising a triazine derivative and at least one lubricant, wherein the triazine derivative comprises at least one triazine group and at least one fluoropolyoxyalkene chain (chain Rf) comprising a fluorocarbon segment having ether linkages in the main chain, wherein chain Rf comprises at least one hydroxyl group.

10. The lubricant composition of claim 9 comprising at least one perfluoropolyether (PFPE) lubricant comprising a perfluorooxyalkylene chain, wherein said chain comprises recurring units having at least one ether bond and at least one fluorocarbon moiety, different from said triazine derivative.

11. A method for lubricating a magnetic recording medium comprising coating on at least one of its surface a composition comprising a triazine derivative, wherein the triazine derivative comprises at least one triazine group and at least one fluoropolyoxyalkene chain (chain Rf) comprising a fluorocarbon segment having ether linkages in the main chain, wherein chain Rf comprises at least one hydroxyl group.

12. The method of claim 11 , wherein the magnetic recording medium is a hard disk.

13. The triazine derivative of claim 3 , wherein each of G, G′, G″, G*, G′*, G″*, G′″*, equal to or different from each other, is independently a hydroxyl-containing group selected from the group consisting of formula (g1), (g2) and (g3):

14. The triazine derivative of claim 4 , wherein each of G, G′, G″, G*, G′*, G″*, G′″*, equal to or different from each other, is independently a hydroxyl-containing group selected from the group consisting of formula (g1), (g2) and (g3):

15. The triazine derivative of claim 6 , wherein each of G, G′, G″, G*, G′*, G″*, G′″*, equal to or different from each other, is independently a hydroxyl-containing group selected from the group consisting of formula (g1), (g2) and (g3):

16. The triazine derivative of claim 8 , wherein each of G, G′, G″, G*, G′*, G″*, G′″*, equal to or different from each other, is independently a hydroxyl-containing group selected from the group consisting of formula (g1), (g2) and (g3):

17. The triazine derivative of claim 5 , wherein G a is a hydroxyl-containing group selected from the group consisting of formula (g1), (g2) and (g3):

18. The triazine derivative of claim 10 , wherein G a is a hydroxyl-containing group selected from the group consisting of formula (g1), (g2) and (g3):

Assignments (1)
MERGER Recorded May 24, 2013
From: SOLVAY SOLEXIS S.P.A.
To: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
Reel/Frame 030482/0192 →
Priority Claims (1)
EP 10193692 · Dec 3, 2010 · regional
Continuity (1)
Related Publication 20130237462A1 · Sep 12, 2013