Coated carbon fiber reinforced plastic parts

Patent metadata

Field	Value
Publication number	US-2016009952-A1
Application number	US-201414438719-A
Country	US
Kind code	A1
Filing date	Mar 31, 2014
Priority date	Apr 2, 2013
Publication date	Jan 14, 2016
Grant date	—

Abstract

Carbon fiber reinforced plastic parts are advantageously coated with powder coating formulations comprising certain red-shifted hydroxyphenylbenzotriazole ultraviolet light absorbers (UVAs). The benzotriazole UVAs are of formulae (I) or (II) The coated carbon fiber reinforced plastic parts are suitable in aerospace applications, automotive parts and sporting goods.

First claim

1 . A composition comprising a carbon fiber reinforced plastic part and a coating layer in adherence thereto,
wherein the coating layer is a cured powder coating formulation comprising a) a powder coating resin, b) a red-shifted hydroxyphenylbenzotriazole ultraviolet light absorber, c) a hindered amine light stabilizer and optionally d) a compound selected from the group consisting of further ultraviolet light absorbers, phenolic antioxidants and organic or inorganic pigments, where the red-shifted hydroxyphenyhlbenzotriazoles are of formulae (I) or (II)

wherein
R 1 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; or
R 1 is a group

or a group

wherein L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms, benzylidene, p-xylylene or cycloalkylene of 5 to 7 carbon atoms;
R 2 is 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 3 alkyl of 1 to 4 carbon atoms; or
said alkyl substituted by one or more —OH, —OCO—R 11 , —OR 14 , —NCO or —NH 2 groups or mixtures thereof, or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NR 14 — groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OR 14 or —NH 2 groups or mixtures thereof; where
R 11 is hydrogen, straight or branched chain C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl, straight or branched chain C 3 -C 8 alkenyl, phenyl, naphthyl or C 7 -C 15 phenylalkyl; and
R 14 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms; or
R 2 is —OR 14 , a group —C(O)—O—R 14 , —C(O)—NHR 14 or —C(O)—NR 14 R′ 14 wherein R′ 14 has the same meaning as R 14 ; or
R 2 is —SR 13 , —NHR 13 or —N(R 13 ) 2 ; or
R 2 is —(CH 2 ) m —CO—X 1 —(Z) p —Y—R 15 wherein
X 1 is —O— or —N(R 16 )—,
Y is —O— or —N(R 17 )— or a direct bond,
Z is C 2 -C 12 -alkylene, C 4 -C 12 alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C 3 -C 12 alkylene, butenylene, butynylene, cyclohexylene or phenylene, each of which may be additionally substituted by a hydroxyl group;
or a group

wherein * denotes a bond; or when Y is a direct bond, Z can additionally also be a direct bond;
m is zero, 1 or 2,
p is 1, or p is also zero when X and Y are —N(R 16 )— and —N(R 17 )—, respectively,
R 15 is hydrogen, C 1 -C 12 alkyl, a group

or a group —CO—C(R 18 )═C(H)R 19 or, when Y is —N(R 17 )—, forms together with R 17 a group —CO—CH═CH—CO— wherein
R 18 is hydrogen or methyl and R 19 is hydrogen, methyl or —CO—X 1 —R 20 , wherein
R 20 is hydrogen, C 1 -C 12 alkyl or a group of formulae

R 5 , R 6 , R 7 and R 8 are independently hydrogen, halogen, CN, NO 2 or NH 2 ;
R 13 is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl or naphthyl, which both may be substituted by one or two alkyl of 1 to 4 carbon atoms;
R 16 and R 17 independently of one another are hydrogen, C 1 -C 12 -alkyl, C 3 -C 12 -alkyl interrupted by 1 to 3 oxygen atoms, or is cyclohexyl or C 7 -C 15 phenylalkyl and R 16 together with R 17 in the case where Z is ethylene, also forms ethylene;
X is O or NE 1 wherein
E 1 is hydrogen, straight or branched chain C 1 -C 24 alkyl, straight or branched chain C 2 -C 18 alkenyl, C 2 -C 6 alkyinyl, C 5 -C 12 cycloalkyl, phenyl, naphthyl or C 7 -C 15 phenylalkyl; or said straight or branched chain C 1 -C 24 alkyl, straight or branched chain C 2 -C 24 alkenyl, C 5 -C 12 cycloalkyl, C 2 -C 6 alkinyl can be substituted by one or more —F, —OH, —OR 22 , —NH 2 , —NHR 22 , —N(R 22 ) 2 , —NHCOR 23 , —NR 22 COR 23 , —OCOR 24 , —COR 25 , —SO 2 R 26 , —PO(R 27 ) n (R 28 ) 2-n , —Si(R 29 ) n (R 30 ) 3-n , —Si(R 22 ) 3 , —N + (R 22 ) 3 A − , —S + (R 22 ) 2 A − , -oxiranyl groups or mixtures thereof; said straight or branched chain C 1 -C 24 alkyl, straight or branched chain unsubstituted or substituted C 2 -C 24 alkenyl, C 5 -C 12 cycloalkyl or C 2 -C 6 alkinyl can also be interrupted by one or more —O—, —S—, —NH— or —NR 22 — groups or combinations thereof;
said phenyl, naphthyl or C 7 -C 15 phenylalkyl can also be substituted by one or more halogen, —CN, —CF 3 , —NO 2 , —NHR 22 , —N(R 22 ) 2 , —SO 2 R 26 , —PO(R 27 ) n (R 28 ) 2-n , —OH, —OR 22 , —COR 25 , —R 25 ; wherein n is 0, 1 or 2;
R 22 is straight or branched chain C 1 -C 18 alkyl, straight or branched chain C 2 -C 18 alkenyl, C 5 -C 10 cycloalkyl, phenyl or naphthyl, C 7 -C 15 phenylalkyl, or two R 22 when attached to an N or Si atom can form together with the atom to which they are bonded a pyrrolidine, piperidine or morpholine ring;
R 23 is hydrogen, OR 22 , NHR 22 , N(R 22 ) 2 or has the same meaning as R 22 ,
R 24 is OR 22 , NHR 22 , N(R 22 ) 2 or has the same meaning as R 22 ,
R 25 is hydrogen, OH, OR 22 , NHR 22 or N(R 22 ) 2 , O-glycidyl or has the same meaning as R 22 ,
R 26 is OH, OR 22 , NHR 22 or N(R 22 ) 2 ,
R 27 is NH 2 , NHR 22 or N(R 22 ) 2 ,
R 28 is OH or OR 22 ,
R 29 is Cl or OR 22 ,
R 30 is straight or branched chain C 1 -C 18 alkyl; or
E 1 is a group

wherein
R 1 to R 8 have the meanings as defined above and
Q is straight or branched C 2 -C 12 alkylene, C 2 -C 12 alkylene, which is interrupted by one or more —O—, NH or NR 14 atoms, C 5 -C 10 cycloalkylene, para-phenylene or a group

wherein * denotes a bond.

2 . A composition according to claim 1 where in the compounds of formulae (I) or (II),
R 1 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; or
R 1 is a group

or a group

wherein L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms, benzylidene, p-xylylene or cycloalkylene of 5 to 7 carbon atoms;
R 2 is 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

Assignees

• Basf Se

Inventors

• Wood Mervin Gale
• BARBER Don
• Hasan Syed
• Braig Adalbert

Classifications

• C09D5/036 Primary

  Stabilisers (organic stabilisers for paints C09D7/48) · CPC title

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C09D175/06 Primary

  from polyesters · CPC title

• C09D7/48

  Stabilisers against degradation by oxygen, light or heat · CPC title

• C08K5/3475

  condensed with carbocyclic rings · CPC title