Photostable, silylated benzotriazole UV absorbers and...

Details Photostable, silylated benzotriazole UV absorbers and... Photostable, silylated benzotriazole UV absorbers and...

2001-08-01

2004-01-13

Wilson, D. R. (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C548S100000, C548S255000, C548S257000, C548S260000, C524S091000, C524S104000, C524S106000, C524S167000, C524S261000, C524S543000, C524S567000, C524S570000

Reexamination Certificate

active

06677392

ABSTRACT:

The instant invention pertains to photostable, silylated benzotriazole UV absorbers and compositions stabilized therewith. These benzotriazole compounds are novel and exhibit enhanced durability due to either the incorporation of electron withdrawing moieties at the 5-position of the benzo ring or to the presence of an &agr;-cumyl group on the phenol ring. The polymer compositions containing said benzotriazoles are advantageously stabilized, especially high performance coatings such as organopolysiloxanes. The instant compounds are red-shifted and show increased absorption in the 350-400 nm region of the UV spectrum.
BACKGROUND OF THE INVENTION
Copending patent application Ser. No. 08/981,433, now U.S. Pat. No. 6,005,036, describes polysiloxanes themselves which are useful as process stabilizers.
U.S. Pat. No. 4,859,759 describes in the most generic manner siloxane compounds containing at least one benzotriazole and one hindered amine substituent covalently coupled to a silicon atom. This reference does not supply any specific exemplification of such structures. The particular structures of the instant invention are neither disclosed nor suggested by this reference.
U.S. Pat. Nos. 5,707,690 and 5,756,793 disclose the use of silylated benzophenones for the protective coatings for wood. EP 675,108 B1 describes thioether substituted benzophenone UV absorbers which may also contain silylated substituents.
U.S. Pat. Nos. 5,185,445 and 5,837,792 describe polysiloxane light stabilizers which contain pendant hydroxyphenyl-diaryl-s-triazine moieties.
U.S. Pat. Nos. 5,219,905; 5,321,066; 5,418,267; 5,463,058 and 5,578,665 disclose hindered amines containing siloxane and other silyl moieties as stabilizers.
U.S. Pat. Nos. 5,391,795 and 5,679,820 describe the preparation and use of silylated benzophenone UV absorbers. U.S. Pat. No. 5,391,795 compares these silylated benzophenone UV absorbers with one example of a silylated benzotriazole UV absorber which is 2-{2-hydroxy-5-[3-(3-triethoxysilyl)propylcarbamoyloxy]propylphenyl}2H-benzotriazole. This silylated benzotriazole compound contains neither a bulky substituent ortho to the hydroxy group in the phenyl ring nor an electron withdrawing group at the 5-position of the benzo ring. Both of these two substitution patterns are shown to be particularly efficacious in enhancing long term photostability of the benzotriazoles. The electron withdrawing group at the 5-position of the benzo ring allows for the red-shifting of the UV spectrum of the benzotriazoles.
U.S. Pat. No. 4,373,061 teaches the use of silicone coatings for unprimed plastic substrates and coated articles. The silicone coating contains a UV absorbing organic group attached to silicon by carbon-silicon bonds. The UV absorber is a silylated hydroxy-benzophenone.
U.S. Pat. No. 4,322,455 describes a process for producing an ultraviolet radiation stabilized polymeric article which contains on the surface of said article a UV absorbing composition. The UV absorber may be generically any of the known types of compounds such as benzophenones, benzotriazole, cyanoacrylates or benzylidene malonates. The only benzotriazole disclosed is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole.
Copending application Ser. No. 09/234,880, now U.S. Pat. No. 6,166,218, demonstrates the value of having such substitution at the 3-position of the phenyl ring by a bulky group and at the 5-position of the benzo ring by an electron withdrawing moiety. All the instant compounds have an electron withdrawing moiety at the 5-position of the benzo ring. When there is a bulky substituent at the 3-position of the phenyl ring, particularly an &agr;-cumyl group, the photostability of the benzotriazole is particularly enhanced.
OBJECTS OF THE INVENTION
The first object of this invention is to provide for new monomeric benzotriazole UV absorbers which contain silicon moieties.
Another object of this invention is to provide silicone/siloxane hardcoat or softcoat resin compositions containing said benzotriazole UV absorbers which can be added to or copolymerized into such hardcoat or softcoat resins.
Still another object of the invention is to provide for articles which contain the siliconelsiloxane hardcoat or softcoat composition as a screening layer in a laminate composition, such as over polycarbonate.
Another object of the invention is provide automotive coating compositions which the instant compounds are melamine/siloxane crosslinked structures.
Still another object of the invention is to provide for polymer compositions where the instant compounds are used in conjunction with silylated hindered amines including inter alia N-hydrocarbyloxy and N-hydroxyalkyloxy substituted hindered amines.
Still another object of the invention is to provide for silicone/siloxane hardcoat or softcoat compositions containing post-added other advanced benzotriazoles which do not contain silicon moieties and with or without the concomitant presence of hindered amines, N-hydrocarbyloxy- or N-hydroxyalkyloxy-substituted hindered amines.
DETAILED DISCLOSURE
The instant invention pertains to benzotriazole compounds of formula (I) or (II)
wherein
G
1
and G
6
are independently hydrogen or halogen;
G
2
and G
7
are independently cyano, perfluoroalkyl of 1 to 12 carbon atoms, fluoro, chloro, —CO—G
3
, —COOG
3
, —CONHG
3
, —CON(G
3
)
2
, E
3
SO—, E
3
SO
2
—, —PO(C
6
H
5
)
2
,
O—CO—NH—T
2
—Si(OR
2
)
n
(R
1
)
3-n
or —CO—X—T
1
—Si(OR
2
)
n
(R
1
)
3-n
;
or G
7
is also hydrogen;
or G
2
may also be hydrogen when E
1
is a group of formula (IV) or (V);
T
1
and T
2
are independently alkylene of 1 to 18 carbon atoms, preferably alkylene of 2 or 3 carbon atoms, or alkylene-phenylene-alkylene of 8 to 20 carbon atoms;
R
1
and R
2
are independently alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 10 carbon atoms or phenylalkyl of 7 to 20 carbon atoms, preferably alkyl of 1 to 6 carbon atoms or phenyl;
n is 0, 1, 2 or 3;
X is —O—, —NE
4
— or —NH—;
G
3
is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms;
E
1
is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms or by one or more of the following groups —T
1
—Si(OR
2
)
n
(R
1
)
3-n
, —T
1
—X—CO—X—T
2
—Si(OR
2
)
n
(R
1
)
3-n
, —T
1
—CO—X—T
2
—Si(OR
2
)
n
(R
1
)
3-n
, —X—T
1
—Si(OR
2
)
n
(R
1
)
3-n
, or —X—T
1
—X—CO—X—T
2
—Si(OR
2
)
n
(R
1
)
3-n
;
or E
1
is alkyl of 1 to 24 carbon atoms substituted by one or two hydroxy groups;
or E
1
is a group of formula (IV) or (V)
where
E
27
and E
28
are independently alkyl of 1 to 18 carbon atoms, or cycloalkyl of 5 to 12 carbon atoms;
E
22
, E
23
, E
24
, E
25
and E
26
are independently hydrogen, halogen, straight or branched alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more halogen, —OCOE
11
, —OE
4
, —NCO, —NHCOE
11
, or —NE
7
E
8
, or mixtures thereof, where E
4
is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms; or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NE
4
— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OE
4
or —NH
2
, or mixtures thereof; or
E
22
, E
23
, E
24
, E
25
and E
26
are independently phenyl, —OH, —OCOE
11
, —OE
29
, —NCO, —NHCOE
11
, or —NE
7
E
8
, cyano, nitro, perfluoroalkyl of 1 to 12 carbon atoms, —COG
3
, —COOG
3
, —CON(G
3
)
2
, —CONHG
3
, E
3
S—, E
3
SO—, E
3
SO
2
—, —P(O)(C
6
H
5
)
2
, —P(O))OG
3
)
2
, —SO
2
—X
1
—E
29
;
X
1
is —O—, —NH— or —

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