Triazine derivative

Patent metadata

Field	Value
Publication number	US-9550954-B2
Application number	US-201113989549-A
Country	US
Kind code	B2
Filing date	Nov 28, 2011
Priority date	Dec 3, 2010
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

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.

First claim

The invention claimed is:

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—, —C

Assignees

• Valsecchi Roberto
• Mutta Fabrizio
• Tonelli Claudio Adolfo Pietro
• Solvay Specialty Polymers It

Inventors

• Valsecchi Roberto
• Mutta Fabrizio
• Tonelli Claudio Adolfo Pietro

Classifications

• C10M133/42 Primary

  Triazines · CPC title

• C08G65/33317

  heterocyclic · CPC title

• C08G65/007 Primary

  containing fluorine · CPC title

• C10M2215/2225

  used as base material · CPC title

• C08G65/00

  Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule · CPC title