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US 6,608,122 B1Granted
Stabilized organic material
AssigneeCiba Specialty Chemicals Corporation
InventorsJean-Luc Birbaum, Jean Rody, Mario Slongo, Andreas Valet, Roland A. E. Winter
Life of this patent
Estimating the term…
Abstract
o-Hydroxyphenyl-s-triazines of the formula I in which n is 1 to 4 and R1 to R7 are as defined in claim 1, can be used, in combination with sterically hindered amines of the polyalkylpiperidine type, for stabilizing organic polymers. Some of these compounds are novel and can also be used without polyalkylpiperidine.
Claims27
An organic material which has been stabilized against damage caused by light, heat and oxygen and which contains
- (a) at least one sterically hindered amine of the polyalkylpiperidine type and
- (b) at least one o-hydroxyphenyl-s-triazine, wherein the triazine compound (b) is a compound of the formula I
- in which n is 1 to 4,
- R1 and R2 independently of one another are H, OH, C1-C12alkyl, cyclohexyl or trifluoromethyl,
- R3 and R4 independently of one another are H, OH, C1-C12alkyl, cyclohexyl, C1-C18alkoxy or halogen and, in the event that n=1, can also be a radical —OR7,
- R5 and R6 independently of one another are H, C1-C12alkyl or halogen,
- R7, if n is 1, is a) C1-C18alkyl which is substituted by one or more of the groups OH, C1-C18alkoxy, C3-C18alkenoxy, halogen, phenoxy (which is unsubstituted or substituted by C1-C18alkyl, C1-C18alkoxy or halogen), furyloxy,
- —COOH, —COOR8, —CONH2, —CONHR9, —CON(R9)(R10), —NH2, —N, —N(R9)(R10), —NHCOR11, —CN and/or by —O—CO—R11,
- b) C4-C50alkyl which is interrupted by one or more O and can be substituted by OH or/and glycidyloxy,
- c) C3-C6alkenyl,
- d) glycidyl or a group
- e) cyclohexyl which is unsubstituted or substituted by OH or —OCOR11,
- f) C7-C11phenylalkyl which is unsubstituted or substituted by OH, Cl or CH3,
- g) —CO—R12 or
- h) —SO2—R13,
- and if n is 2, R7 is a) C2-C16alkylene,
- b) C4-C12alkenylene,
- c) xylylene,
- d) C3-C20alkylene which is interrupted by one or more O and/or substituted by OH,
- e) a group —CH2CH(OH)CH2O—R15—OCH2CH(OH)CH2—, —CO—R16—CO—, —CO—NH—R17—NH—CO— or —(CH2)m—COO—R18—OOC—(CH2)m— (in which m is 1 to 3) or
- and if n is 3, R7 is a group
- and if n is 4, R7 is a group
- R8 is C1-C18alkyl, C3-C18alkenyl, C3-C20alkyl which is interrupted by one or more O, N or S and/or substituted by OH, C1-C4alkyl which is substituted by —P(O)(OR14)2, —N(R9)(R10) or —OCOR11 and/or OH, C3-C18alkenyl, glycidyl or C7-C11phenylalkyl,
- R9 and R10 independently of one another are C1-C12alkyl, C3-C12alkoxyalkyl, C4-C16dialkylaminoalkyl or C5-C12cycloalkyl, or R9 and R10 together are C3-C9alkylene or C3-C9oxaalkylene or C3-C9azaalkylene,
- R11 is C1-C18alkyl, C2-C18alkenyl or phenyl,
- R12 is C1-C18alkyl, C2-C18alkenyl, phenyl, C1-C12alkoxy, phenoxy, C1-C12alkylamino or C6-C12arylamino or a group —R24—COOH or —NH—R17—NCO,
- R13 is C1-C12alkyl, C6-C12aryl or C7-C14alkaryl,
- R14 is C1-C12alkyl or phenyl,
- R15 is C2-C10alkylene, C4-C50alkylene which is interrupted by one or more O, phenylene or a group -phenylene-X-phenylene- in which X is —O—, —S—, —SO2—, —CH2— or —C(CH3)2—,
- R16 is C2-C10alkylene, C2-C10oxaalkylene or C2-C10thiaalkylene, C6-C12arylene or C2-C6alkenylene,
- R17 is C2-C10alkylene, phenylene, tolylene, diphenylenemethane or a group
- R18 is C2-C10alkylene or C4-C20alkylene which is interrupted by one or more O,
- R19 is C3-C12alkanetriyl,
- R20 is C4-C12alkanetetryl,
- R23 is C2-C10alkylene, phenylene or a group
- wherein X is O, S, SO2, CH2 or C(CH3)2, and
- R24 is C2-C14alkylene, vinylene or o-phenylene.
34 more elements
A compound of the formula Ia
- in which n is 1 to 4,
- R1 and R2 independently of one another are H, OH, C1-C12alkyl, cyclohexyl or trifluoromethyl,
- R3 and R4 independently of one another are H, OH, C1-C12alkyl, cyclohexyl, C1-C18alkoxy or halogen and, in the event that n=1, can also be a radical —OR7,
- R5 and R6 independently of one another are H, C1-C12alkyl or halogen,
- R7, if n is 1, is a) C1-C12alkyl which is substituted by phenoxy (which is unsubstituted or substituted by C1-C18alkyl, C1-C18alkoxy or halogen) or by a group —COOR8, —CONH2, —CONHR9, —CON(R9)(R10), —NH2, NHR9, —N(R9)(R10) or —O—CO—R22,
- b) C4-C50alkyl which is interrupted by more than one O and can be substituted by OH or/and glycidyloxy,
- c) glycidyl or a group
- d) cyclohexyl substituted by OH or —OCOR11
- e) a group —CH2CH(OH)CH2OR21
- f) a group —SO2—R13,
- g) a group —CO—R12
- and if n is 2, R7 is
- a) C2-C12alkylene,
- b) C4-C12alkenylene,
- c) xylylene,
- d) C3-C20alkylene which is interrupted by one or more O and/or substituted by OH,
- e) a group —CH2CH(OH)CH2O—R15—OCH2CH(OH)CH2—, —(CH2)m—COO—R18—OOC—(CH2)m— (wherein m is 1-3) or
- and if n is 3, R7 is a group
- (wherein m is 1-3),
- and if n is 4, R7 is a group
- (wherein m is 1-3),
- R8 is C3-C20alkyl which is interrupted by one or more O, N or S and can be substituted by OH, or R8 is C1-C4alkyl which is substituted by —P(O)(OR14)2, —N(R9)(R10), or —OCOR11 and/or OH, or R8 is C3-C18alkenyl, glycidyl or C7-C11phenylalkyl,
- R9 and R10 independently are C1-C12alkyl, C3-C12alkoxyalkyl, C4-C16dialkylaminoalkyl or C5-C12cycloalkyl, or R9 and R10 together are C3-C9alkylene or C3-C9oxaalkylene or C3-C9azaalkylene,
- R11 is C1-C18alkyl, C2-C18alkenyl or phenyl,
- R12 is a group —R24—COOH or —NH—R17—NCO,
- R13 is C1-C12alkyl, C6-C12aryl or C7-C14alkaryl
- R14 is C1-C12alkyl or phenyl
- R15 is C2-C10alkylene, C4-C50alkylene which is interrupted by one or more O, or R15 is phenylene or a group -phenylene-X-phenylene in which X is —O—, —S—, —SO2—, —CH2— or —C(CH3)2—,
- R17 is C2-C10alkylene, phenylene, tolylene, diphenylenemethane or a group
- R18 is C2-C10alkylene or C4-C20alkylene which is interrupted by one or more O,
- R19 is C3-C12alkanetriyl,
- R20 is C4-C12alkanetetryl,
- R21 is H, C1-C18alkyl, C3-C18alkenyl, phenyl, phenyl substituted by C1-C12alkyl, C1-C12alkoxy or halogen, or R21 is C2-C18alkanoyl, benzoyl, C3-C18alkenoyl, furyl or a group
- R22 is C2-C5alkenyl,
- R23 is C2-C10alkylene, phenylene or a group
- wherein X is O, S, SO2, CH2 or C(CH3)2, and
- R24 is C2-C14alkylene, vinylene or o-phenylene.
34 more elements
Dependencies are inferred from the claim text.