Patent TW-375650-B (TW)
Title: Stabilization of paints with spiroindane derivatives
Inventor: LAVER HUGH STEPHEN
IPC: C07D211/46
Filed: 1997-06-11
Granted: 1999-12-01
Abstract: Paint or coating compositions are stabilized by spiroindane compounds of the following formula (1), wherein the number radicals R have the meanings given in claim 1, and optionally phosphite stabilizers and phenolic antioxidants. The claimed product includes a mixture of 100 parts by weight, consisting of (A) coating material or paint, (B) at least a compound of 0.01-10 parts by weight with the following formulas, where R1, R2, R3 and R4 are each independently (a) C1-C18 unsubstituted alkyl or C1-C18 alkyl, substituted by one or more OH, C1-C18 alkoxy, C2-C18 alkenoxy, halogen, phenoxy group (which is unsubstituted or substituted by C1-C18 alkyl group, C1-C18 alkoxy or halogen), -COOR8, -CONH2, -CONHR9 or CONR9R10; (b) C5-C12 cycloalkyl, unsubstituted or substituted by OH or -OCOR11; (c) a 5- or 6-member heterocyclic ring, saturated or unsaturated; (d) C7-C11 phenyl alkyl, unsubstituted or substituted by one or more OH, C1 or CH3; (e) C2-C18 is alkenyl; (f) C4-C30 alkyl group, interrupted by one or more O atoms and substitutable by OH; (g) -CO-R12 or -(CH2)n-CO-R12; (h) -SO2-R13; n is 1 to 18; R5 is H, C1-C18 straight chained or branch chained alkyl, C2-C18 alkenyl or C6-C12 aryl; R6 and R7 are independently H, halogen, C-C18 alkyl, C2-C6 alkenyl, C1-C12 alkoxy or C2-C12 alkenoxy; R8 is C1-C18 alkyl, C2-C18 alkenyl; C3-C20 alkyl, substituted by one or more O atoms, NR9 or S interrupted and/or OH, C1-C4 alkyl (substituted by -P(O) (OR18)2, C3-C8 alkynyl, or C7-C11 phenyl alkyl); R9 and R10 are each independently C 1-C12 alkyl, C3-C12 alkoxy alkyl, C4-C16 dialkyl aminoalkyl or C5-C12 cycloalkyl, or R9 and R10 together are C3-C9 alkylene or C3-C9 oxy heteroalkylene or C3-C9 nitroheteroalkylene; R11 is C1-C18 alkyl, C2-C18 alkenyl or phenyl; R12 is C1-C18, C2-C18 alkenyl, phenyl, C1-C12 alkoxy, phenoxy, C1-C12 alkylamino or C6-C12 arylamino or -R19-COOH; R13 is C1-C12 alkyl, C6-C12 aryl or C7-C14 alkylaryl; R14 is hydrogen, oxy, hydroxy, -CH2CN, C1-C18, C1-C18 alkoxy, C3-C8 alkenyl, C3-C8 alkynyl, C5-C8 cycloalkyl or alkoxy, phenyl, naphthyl, C7-C12 phenylalkyl, or alkoxy, phenyl, or phenylalkyl substituted by alkyl or phenyl having 7-14 carbon atoms, C3-C5 enoyl, C1-C18 alkynyl acyloxy, benzyloxy, or CH2(OH)-Z, wherein z is H, CH3 or phenyl, or a group having the following formula: wherein D' is C1-C18 alkyl, C1-C18 alkoxy, phenyl or phenyl substituted by hydroxyl, C1-C8 alkyl, C1-C8 alkoxy, amino, or C1-C8 alkyl or phenyl mono- or di-substituted phenyl; R15 is H, C1-C18 alkyl, or C3-C18 alkyl, interrupted by one or more oxygen atoms, cyanoethyl, benzyl, cyclooxypropyl, aliphatic, cycloaliphatic, monovalent reaction group of aliphatic like or aryl carboxyl, or monovalent reaction group containing aminoformic acid, or sulfuric acid, or monovalent silicon reaction group -Si(R21) (R22)(R23); R16 is H, -COR11, -Si(R21)(R22)(R23) or -COOR24; R17 is C1-C16 alkyl, C2-C18 alkenyl, phenyl-C1-C4 alkyl, C3-C24 alkyl or C2-C14 hydroxyalkyl, wherein each is interrupted by one or more O atoms, or phenyl, or unsubstituted, or substituted by C1-C4 alkyl, C1-C4 alkoxy or halogen, C5-C12 cycloalkyl, unsubstituted or substituted by 1-3 C1-C8 alkyl or COR11, or (formula) R18 is C1-C18 alkyl or phenyl; R19 is C1-C18 alkylene, ethylene, or phenylene; R20 is H, OH, oxy, C1-C18 alkyl, C2-C18 alkenyl, C1-C18 alkoxy, C5-C12 cycloalkyl, C5-C12 cycloalkoxy, C3-C8 alkynyl, C7-C12 phenylalkyl, C1-C8 alkylacyl, C3-C5 alkenylacyl or cyclooxypropyl; R21, R22 and R23 are each independently C1-C6 alkyl or phenyl; R24 is C1-C4 alkyl.