US2008171802A1PendingUtilityA1
Methyltrialkylsilanes containing a cinnamate, cinnamamide, benzalmalonamide or benzalmalonate function and photostabilizing methods
Est. expiryJan 28, 2023(expired)· nominal 20-yr term from priority
Inventors:Herve Richard
C07F 7/081C07F 7/0812A61K 8/893A61K 8/585A61K 8/898A61Q 17/04
56
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
Unique photoprotective compositions contain novel methyltrialkylsilanes bearing a cinnamate, cinnamamide, benzalmalonamide or benzalmalonate function, useful as sunscreens that are active in the field of UV radiation and also useful in methods for photostabilizing synthetic polymers or glasses.
Claims
exact text as granted — not AI-modified1 . A method for photostabilizing a synthetic polymer or a glass, comprising incorporating therein an effective photostabilizing amount of at least one methyltrialkylsilane compound having the formula (I) below:
in which:
B is a chromophoric group having either of formulae (1) and (2) below:
R 1 and R 2 , which may be identical or different, are each a linear or branched C 1 -C 12 alkyl radical, optionally halogenated or containing a double bond or a triple bond, or a phenyl or benzyl radical;
R 3 is a radical R 1 or R 2 or a group B;
n is an integer ranging from 0 to 3 inclusive;
X is —O— or —NR 5 —;
A is a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical, a group SiR 1 R 2 R 3 in which R 1 , R 2 and R 3 are as defined above, with the proviso that R 3 is other than B;
the radical R′ is a hydrogen atom, a linear or branched C 1 -C 10 alkyl radical, a linear or branched C 2 -C 8 alkenyl radical or an Si(CH 3 ) 3 group;
the radicals R″, which may be identical or different, are each a hydroxyl radical, a linear or branched C 1 -C 10 alkyl radical, a linear or branched C 2 -C 8 alkenyl radical, a linear or branched C 1 -C 10 alkoxy radical, with the proviso that R″ may together form with an adjacent R″ or OR′, an alkylidenedioxy group in which the alkylidene group contains one or two carbon atoms, or an —OSi(CH 3 ) 3 group;
Z, Z′ and Z″, which may be identical or different, are each a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical; a group —(C═O)R 4 , —(C═O)OR 4 , —SO 2 R 5 , —(C═O)NR 6 R 7 , —CN or —(C═O)XCHASiR 1 R 2 R 3 in which R 1 , R 2 and R 3 are as defined above, with the proviso that R 3 is other than B, and with the further proviso that:
(i) at least one of the radicals Z′ and Z″ is other than hydrogen, and
(ii) when Z′ is —SO 2 R 5 , then Z″ is other than a —CN group;
R 4 is a hydrogen atom or a linear or branched C 1 -C 20 alkyl radical;
R 5 is a C 1 -C 20 alkyl radical or a C 6 -C 12 aryl radical; and
R 6 and R 7 , which may be identical or different, are each a hydrogen atom or a C 1 -C 4 alkyl radical; with the further proviso that:
Z′ and Z″ may also together form a Meldrum acid of formula (3) below:
in which
R 8 and R 9 , which may be identical or different, are each hydrogen or a linear or branched C 1 -C 20 alkyl radical; and R 8 and R 9 may also together form a C 5 -C 12 ring member.
2 . The method as defined by claim 1 , wherein, in the compound of formula (I), B is a chromophoric group (1).
3 . The method as defined by claim 1 , wherein, in the compound of formula (I), B is a chromophoric group (2).
4 . The method as defined by claim 1 , wherein, in the compound of formula (I), R 3 is a group B.
5 . The method as defined by claim 2 , wherein, in the compound of formula (I), X is —O—.
6 . The method as defined by claim 2 , wherein, in the compound of formula (I), X is —NR 5 .
7 . The method as defined by claim 2 , wherein, in the compound of formula (I):
R 1 , R 2 and R 3 are each a C 1 -C 4 alkyl radical; Z is hydrogen, COOR 4 in which R 4 is a C 1 -C 8 alkyl radical, CN or —(C═O)XCHASiR 1 R 2 R 3 ; A is a hydrogen atom; X is O or NH; n=0; and R′ is a C 1 -C 4 alkyl radical.
8 . The method as defined by claim 7 , wherein, in the compound of formula (I):
Z is COOR 4 and R 4 is methyl; and R 1 , R 2 and R 3 are each methyl.
9 . The method as defined by claim 1 , wherein said at least one methyltrialkylsilane compound of formula (I) is selected from the group consisting of the following compounds:
10 . The method as defined by claim 3 , wherein, in the compound of formula (I):
A is a hydrogen atom; R 1 and R 2 are each a C 1 -C 4 alkyl radical; n=0 or 1 and when n=1, R″ is a C 1 -C 4 alkoxy radical; Z′ and Z″, which may be identical or different, are each a group selected from among: 1) —(C═O)OR 4 in which R 4 is a C 1 -C 8 alkyl radical; 2) —(C═O)NH 2 ; 3) —CN; 4) or a group of formula (3) in which R 8 and R 9 are each a C 1 -C 4 alkyl radical.
11 . The method as defined by claim 10 , wherein, in the compound of formula (I):
R 1 and R 2 are each methyl; Z′ and Z″ form a group of formula (3) and R 8 and R 9 are each methyl; and n=1 and R″ is methoxy.
12 . The method as defined by claim 1 , said at least one methyltrialkylsilane compound of formula (I) being selected from the group consisting of the following compounds:
13 . A synthetic polymer or glass having incorporated therein an effective photostabilizing amount of at least one methyltrialkylsilane compound having the formula (I) below:
in which:
B is a chromophoric group having either of formulae (1) and (2) below:
R 1 and R 2 , which may be identical or different, are each a linear or branched C 1 -C 12 alkyl radical, optionally halogenated or containing a double bond or a triple bond, or a phenyl or benzyl radical;
R 3 is a radical R 1 or R 2 or a group B;
n is an integer ranging from 0 to 3 inclusive;
X is —O— or —NR 5 —;
A is a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical, a group SiR 1 R 2 R 3 in which R 1 , R 2 and R 3 are as defined above, with the proviso that R 3 is other than B;
the radical R′ is a hydrogen atom, a linear or branched C 1 -C 10 alkyl radical, a linear or branched C 2 -C 8 alkenyl radical or an Si(CH 3 ) 3 group;
the radicals R″, which may be identical or different, are each a hydroxyl radical, a linear or branched C 1 -C 10 alkyl radical, a linear or branched C 2 -C 8 alkenyl radical, a linear or branched C 1 -C 10 alkoxy radical, with the proviso that R″ may together form with an adjacent R″ or OR′, an alkylidenedioxy group in which the alkylidene group contains one or two carbon atoms, or an —OSi(CH 3 ) 3 group;
Z, Z′ and Z″, which may be identical or different, are each a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical; a group —(C═O)R 4 , —(C═O)OR 4 , —SO 2 R 5 , —(C═O)NR 6 R 7 , —CN or —(C═O)XCHASiR 1 R 2 R 3 in which R 1 , R 2 and R 3 are as defined above, with the proviso that R 3 is other than B, and with the further proviso that:
(i) at least one of the radicals Z′ and Z″ is other than hydrogen, and
(ii) when Z′ is —SO 2 R 5 , then Z″ is other than a —CN group;
R 4 is a hydrogen atom or a linear or branched C 1 -C 20 alkyl radical;
R 5 is a C 1 -C 20 alkyl radical or a C 6 -C 12 aryl radical; and
R 6 and R 7 , which may be identical or different, are each a hydrogen atom or a C 1 -C 4 alkyl radical; with the further proviso that:
Z′ and Z″ may also together form a Meldrum acid of formula (3) below:
in which
R 8 and R 9 , which may be identical or different, are each hydrogen or a linear or branched C 1 -C 20 alkyl radical; and R 8 and R 9 may also together form a C 5 -C 12 ring member.
14 . A methyltrialkylsilane compound having the formula (1) below:
in which:
B is a chromophoric group having either of formulae (1) and (2) below:
R 1 and R 2 , which may be identical or different, are each a linear or branched C 1 -C 12 alkyl radical, optionally halogenated or containing a double bond or a triple bond, or a phenyl or benzyl radical;
R 3 is a radical R 1 or R 2 or a group B;
n is an integer ranging from 0 to 3 inclusive;
X is —O— or —NR 5 —;
A is a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical, a group SiR 1 R 2 R 3 in which R 1 , R 2 and R 3 are as defined above, with the proviso that R 3 is other than B;
the radical R′ is a hydrogen atom, a linear or branched C 1 -C 10 alkyl radical, a linear or branched C 2 -C 8 alkenyl radical or an Si(CH 3 ) 3 group;
the radicals R″, which may be identical or different, are each a hydroxyl radical, a linear or branched C 1 -C 10 alkyl radical, a linear or branched C 2 -C 8 alkenyl radical, a linear or branched C 1 -C 10 alkoxy radical, with the proviso that R″ may together form with an adjacent R″ or OR′, an alkylidenedioxy group in which the alkylidene group contains one or two carbon atoms, or an —OSi(CH 3 ) 3 group;
Z, Z′ and Z″, which may be identical or different, are each a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical; a group —(C═O)R 4 , —(C═O)OR 4 , —SO 2 R 5 , —(C═O)NR 6 R 7 , —CN or —(C═O)XCHASiR 1 R 2 R 3 in which R 1 , R 2 and R 3 are as defined above, with the proviso that R 3 is other than B, and with the further proviso that:
(i) at least one of the radicals Z′ and Z″ is other than hydrogen, and
(ii) when Z′ is —SO 2 R 5 , then Z″ is other than a —CN group;
R 4 is a hydrogen atom or a linear or branched C 1 -C 20 alkyl radical;
R 5 is a C 1 -C 20 alkyl radical or a C 6 -C 12 aryl radical;
R 6 and R 7 , which may be identical or different, are each a hydrogen atom or a C 1 -C 4 alkyl radical; with the further proviso that:
Z′ and Z″ may also together form a Meldrum acid of formula (3) below:
in which
R 8 and R 9 , which may be identical or different, are each hydrogen or a linear or branched C 1 -C 20 alkyl radical; and R 8 and R 9 may also together form a C 5 -C 12 ring member.
15 . The methyltrialkylsilane compound as defined by claim 14 , wherein B is a chromophoric group (1).
16 . The methyltrialkylsilane compound as defined by claim 14 , wherein B is a chromophoric group (2).
17 . The methyltrialkylsilane compound as defined by claim 14 , wherein R 3 is a group B.
18 . The methyltrialkylsilane compound as defined by claim 15 , wherein X is —O—.
19 . The methyltrialkylsilane compound as defined by claim 15 , wherein X is —NR 5 .
20 . The methyltrialkylsilane compound as defined by claim 15 , wherein:
R 1 , R 2 and R 3 are each a C 1 -C 4 alkyl radical; Z is hydrogen, COOR 4 in which R 4 is a C 1 -C 8 alkyl radical, CN or —(C═O)XCHASiR 1 R 2 R 3 ; A is a hydrogen atom; X is O or NH; n=0; and R′ is a C 1 -C 4 alkyl radical.
21 . The methyltrialkylsilane compound as defined by claim 20 , wherein:
Z is COOR 4 and R 4 is methyl; and R 1 , R 2 and R 3 are each methyl.
22 . The methyltrialkylsilane compound as defined by claim 14 , said compound being selected from the group consisting of the following compounds:
23 . The methyltrialkylsilane compound as defined by claim 16 , wherein:
A is a hydrogen atom; R 1 and R 2 are each a C 1 -C 4 alkyl radical; n=0 or 1 and when n=1, R″ is a C 1 -C 4 alkoxy radical; Z′ and Z″, which may be identical or different, are each a group selected from among: 1) —(C═O)OR 4 in which R 4 is a C 1 -C 8 alkyl radical; 2) —(C═O)NH 2 ; 3) —CN; 4) or a group of formula (3) in which R 8 and R 9 are each a C 1 -C 4 alkyl radical.
24 . The methyltrialkylsilane compound as defined by claim 23 , wherein:
R 1 and R 2 are each methyl; Z′ and Z″ form a group of formula (3) and R 8 and R 9 are each methyl; and n=1 and R″ is methoxy.
25 . The methyltrialkylsilane compound as defined by claim 14 , said compound being selected from the group consisting of the following compounds:Join the waitlist — get patent alerts
Track US2008171802A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.