US 6,653,324 B1Granted

Stabilization of wood substrates

AssigneeCiba Specialty Chemicals Corporation

InventorsManfred Köhler, Clemens Auschra, Glen Thomas Cunkle, Peter Nesvadba, Raymond Seltzer

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Abstract

The invention relates to a method of protecting wood against light-induced degradation by treatment with an impregnation which penetrates the surface of the wood comprising a) water without an organic solvent and b) a selected sterically hindered amine N-oxyl or N-hydroxyl. A further subject is the use of a sterically hindered amine N-oxyl or N-hydroxyl for the stabilization of wood.

Claims12

Dependent claims

A method of protecting wood against light-induced degradation by treatment of wood with an impregnation which penetrates the surface of the wood, said impregnation comprising

a) water without an organic solvent and
b) a sterically hindered amine which is selected from the group consisting of compounds of formulae A to R and A* to R*
wherein
E is oxyl or hydroxyl,
R is hydrogen or methyl,
in formula A and A*,
n is 1 or 2,
when n is 1,
R1 is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2-18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, said alkyl substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or
R1 is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —(COO−)nMn+ where n is 1-3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group Nn+(R2)4 where R2 is alkyl of 1 to 8 carbon atoms or benzyl,
when n is 2,
R1 is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,
in formula B and B*,
m is 1 to 4,
when m is 1,
R2 is alkyl of 1 to 18 carbon atoms, alkyl of 3 to 18 carbon atoms interrupted by —COO—, alkyl of 3 to 18 carbon atoms substituted by COOH or COO—, or R2 is —CH2(OCH2CH2)nOCH3 where n is 1 to 12, or
R2 is cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, or said aryl substituted by one to four alkyl groups of 1 to 4 carbon atoms, or
R2 is —NHR3 where R3 is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, or said aryl substituted by one to four alkyl of 1 to 4 carbon atoms, or
R2 is —N(R3)2 where R3 is as defined above,
when m is 2,
R2 is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene, alkylene of 2 to 12 carbon atoms interrupted by —COO—, alkylene of 3 to 18 carbon atoms substituted by COOH or COO—, or R2 is —CH2(OCH2CH2)nOCH2— where n is 1 to 12, or
R2 is cycloalkylene of 5 to 12 carbon atoms, aralkylene of 7 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or
R2 is —NHR4NH— where R4 is alkylene of 2 to 18 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, aralkylene of 8 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or
R2 is —N(R3)R4N(R3)— where R3 and R4 are as defined above, or
R2 is —CO— or —NH—CO—NH—,
when m is 3,
R2 is alkanetriyl of 3 to 8 carbon atoms or benzenetriyl, or
when m is 4,
R2 is alkanetetrayl of 5 to 8 carbon atoms or benzenetetrayl,
in formula C and C*,
R10 is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, alkanoyl of 2 to 18 carbon atoms, alkenoyl of 3 to 5 carbon atoms or benzoyl,
x is 1 or 2,
when x is 1,
R11 is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, said alkyl substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or
R11 is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —(COO−)nMn+ where n is 1-3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group Nn+(R2)4 where R2 is hydrogen, alkyl of 1 to 8 carbon atoms or benzyl, or
when x is 2,
R11 is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,
in formula D and D*,
R10 is as defined above,
y is 1 to 4, and
R12 is defined as R2 above,
in formula E and E*,
E1 and E2, being different, each are —CO— or —N(E5)— where E5 is hydrogen, alkyl of 1 to 12 carbon atoms or alkoxycarbonylalkyl of 4 to 22 carbon atoms,
E3 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl, said phenyl or said naphthyl substituted by chlorine or by alkyl of 1 to 4 carbon atoms, or phenylalkyl of 7 to 12 carbon atoms, or said phenylalkyl substituted by alkyl of 1 to 4 carbon atoms,
E4 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl or phenylalkyl of 7 to 12 carbon atoms, or
E3 and E4 together are polymethylene of 4 to 17 carbon atoms, or said polymethylene substituted by one to four alkyl of 1 to 4 carbon atoms, preferably methyl,
in formula F and F*,
R10 is as defined for R10 in formula C,
in formula G and G*,
E6 is an aliphtic or aromatic tetravalent radical, preferably neopentanetetrayl or benzenetetrayl,
in formula K and K*,
R51 is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, or aryl of 6 to 10 carbon atoms,
R52 is hydrogen or alkyl of 1 to 18 carbon atoms, or
R51 and R52 together of alkylene of 4 to 8 carbon atoms,
f is 1 or 2,
when f is 1,
R50 is as defined for R11 in formula C when x is 1, or R50 is —(CH2)zCOOR54 where z is 1 to 4 and R54 is hydrogen or alkyl of 1 to 18 carbon atoms, or R54 is a metal ion from the 1st, 2nd or 3rd group of the periodic table or a group —N(R55)4 where R55 is hydrogen, alkyl of 1 to 12 carbon atoms or benzyl,
when f is 2,
R50 is as defined for R11 in formula C when x is 2,
wherein in formulas M to Q and M* to Q*
G1 is hydrogen, methyl, ethyl, butyl or benzyl,
n is 2 to 3,
m is 1 to 4,
x is 1 to 4,
when x is 1, R101 and R102 are independently alkyl of 1 to 18 carbon atoms, said alkyl interrupted by one to five oxygen atoms, said alkyl substituted by 1 to 5 hydroxyl groups or said alkyl both interrupted by said oxygen atoms and substituted by said hydroxyl groups;
cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one to three alkyl of 1 to 8 carbon atoms, or R1 is also hydrogen,
or R101 and R102 are together tetramethyl, pentamethylene, hexamethylene or 3-oxapentamethylene,
when x is 2,
R101 is hydrogen, alkyl of 1 to 8 carbon atoms, said alkyl interrupted by one or two oxygen atoms, said alkyl substituted by a hydroxyl group, or said alkyl both interrupted by one or two oxygen atoms and substituted by a hydroxyl group,
R102 is alkylene of 2 to 18 carbon atoms, said alkylene interrupted by one to five oxygen atoms, said alkylene substituted by 1 to 5 hydroxyl groups or said alkylene both interrupted by said oxygen atoms and substituted by said hydroxyl groups;
o-, m- or p-phenylene or said phenylene substituted by one or two alkyl of 1 to 4 carbon atoms, or
R102 is —(CH2)kO[(CH2)kO]h(CH2)k— where k is 2 to 4 and h is 1 to 40, or
R101 and R102 together with the two N atoms to which they are attached are piperazin-1,4-diyl,
when x is 3,
R101 is hydrogen,
R102 is alkylene of 4 to 8 carbon atoms interrupted by one nitrogen atom,
when x is 4,
R101 is hydrogen,
R102 is alkylene of 6 to 12 carbon atoms interrupted by two nitrogen atoms,
R103 is hydrogen, alkyl of 1 to 8 carbon atoms, said alkyl interrupted by one or two oxygen atoms, said alkyl substituted by a hydroxyl group, or both interrupted by one or two oxygen atoms and substituted by a hydroxyl group,
and Q is an alkali metal salt, ammonium or N+(G1)4,
and in formula R and R*
m is 2 or 3,
when m is 2, G is —(CH2CHR—O)rCH2CHR—, where r is 0 to 3, and R is hydrogen or methyl, and
when m is 3, G is glyceryl,
X is an inorganic or organic anion,
where the total charge of cations h is equal to the total charge of anions j.

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Dependencies are inferred from the claim text.

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Abstract

A method of protecting wood against light-induced degradation by treatment of wood with an impregnation which penetrates the surface of the wood, said impregnation comprising

a) water without an organic solvent and
b) a sterically hindered amine which is selected from the group consisting of compounds of formulae A to R and A* to R*
wherein
E is oxyl or hydroxyl,
R is hydrogen or methyl,
in formula A and A*,
n is 1 or 2,
when n is 1,
R1 is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2-18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, said alkyl substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or
R1 is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —(COO−)nMn+ where n is 1-3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group Nn+(R2)4 where R2 is alkyl of 1 to 8 carbon atoms or benzyl,
when n is 2,
R1 is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,
in formula B and B*,
m is 1 to 4,
when m is 1,
R2 is alkyl of 1 to 18 carbon atoms, alkyl of 3 to 18 carbon atoms interrupted by —COO—, alkyl of 3 to 18 carbon atoms substituted by COOH or COO—, or R2 is —CH2(OCH2CH2)nOCH3 where n is 1 to 12, or
R2 is cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, or said aryl substituted by one to four alkyl groups of 1 to 4 carbon atoms, or
R2 is —NHR3 where R3 is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, or said aryl substituted by one to four alkyl of 1 to 4 carbon atoms, or
R2 is —N(R3)2 where R3 is as defined above,
when m is 2,
R2 is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene, alkylene of 2 to 12 carbon atoms interrupted by —COO—, alkylene of 3 to 18 carbon atoms substituted by COOH or COO—, or R2 is —CH2(OCH2CH2)nOCH2— where n is 1 to 12, or
R2 is cycloalkylene of 5 to 12 carbon atoms, aralkylene of 7 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or
R2 is —NHR4NH— where R4 is alkylene of 2 to 18 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, aralkylene of 8 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or
R2 is —N(R3)R4N(R3)— where R3 and R4 are as defined above, or
R2 is —CO— or —NH—CO—NH—,
when m is 3,
R2 is alkanetriyl of 3 to 8 carbon atoms or benzenetriyl, or
when m is 4,
R2 is alkanetetrayl of 5 to 8 carbon atoms or benzenetetrayl,
in formula C and C*,
R10 is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, alkanoyl of 2 to 18 carbon atoms, alkenoyl of 3 to 5 carbon atoms or benzoyl,
x is 1 or 2,
when x is 1,
R11 is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, said alkyl substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or
R11 is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —(COO−)nMn+ where n is 1-3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group Nn+(R2)4 where R2 is hydrogen, alkyl of 1 to 8 carbon atoms or benzyl, or
when x is 2,
R11 is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,
in formula D and D*,
R10 is as defined above,
y is 1 to 4, and
R12 is defined as R2 above,
in formula E and E*,
E1 and E2, being different, each are —CO— or —N(E5)— where E5 is hydrogen, alkyl of 1 to 12 carbon atoms or alkoxycarbonylalkyl of 4 to 22 carbon atoms,
E3 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl, said phenyl or said naphthyl substituted by chlorine or by alkyl of 1 to 4 carbon atoms, or phenylalkyl of 7 to 12 carbon atoms, or said phenylalkyl substituted by alkyl of 1 to 4 carbon atoms,
E4 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl or phenylalkyl of 7 to 12 carbon atoms, or
E3 and E4 together are polymethylene of 4 to 17 carbon atoms, or said polymethylene substituted by one to four alkyl of 1 to 4 carbon atoms, preferably methyl,
in formula F and F*,
R10 is as defined for R10 in formula C,
in formula G and G*,
E6 is an aliphtic or aromatic tetravalent radical, preferably neopentanetetrayl or benzenetetrayl,
in formula K and K*,
R51 is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, or aryl of 6 to 10 carbon atoms,
R52 is hydrogen or alkyl of 1 to 18 carbon atoms, or
R51 and R52 together of alkylene of 4 to 8 carbon atoms,
f is 1 or 2,
when f is 1,
R50 is as defined for R11 in formula C when x is 1, or R50 is —(CH2)zCOOR54 where z is 1 to 4 and R54 is hydrogen or alkyl of 1 to 18 carbon atoms, or R54 is a metal ion from the 1st, 2nd or 3rd group of the periodic table or a group —N(R55)4 where R55 is hydrogen, alkyl of 1 to 12 carbon atoms or benzyl,
when f is 2,
R50 is as defined for R11 in formula C when x is 2,
wherein in formulas M to Q and M* to Q*
G1 is hydrogen, methyl, ethyl, butyl or benzyl,
n is 2 to 3,
m is 1 to 4,
x is 1 to 4,
when x is 1, R101 and R102 are independently alkyl of 1 to 18 carbon atoms, said alkyl interrupted by one to five oxygen atoms, said alkyl substituted by 1 to 5 hydroxyl groups or said alkyl both interrupted by said oxygen atoms and substituted by said hydroxyl groups;
cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one to three alkyl of 1 to 8 carbon atoms, or R1 is also hydrogen,
or R101 and R102 are together tetramethyl, pentamethylene, hexamethylene or 3-oxapentamethylene,
when x is 2,
R101 is hydrogen, alkyl of 1 to 8 carbon atoms, said alkyl interrupted by one or two oxygen atoms, said alkyl substituted by a hydroxyl group, or said alkyl both interrupted by one or two oxygen atoms and substituted by a hydroxyl group,
R102 is alkylene of 2 to 18 carbon atoms, said alkylene interrupted by one to five oxygen atoms, said alkylene substituted by 1 to 5 hydroxyl groups or said alkylene both interrupted by said oxygen atoms and substituted by said hydroxyl groups;
o-, m- or p-phenylene or said phenylene substituted by one or two alkyl of 1 to 4 carbon atoms, or
R102 is —(CH2)kO[(CH2)kO]h(CH2)k— where k is 2 to 4 and h is 1 to 40, or
R101 and R102 together with the two N atoms to which they are attached are piperazin-1,4-diyl,
when x is 3,
R101 is hydrogen,
R102 is alkylene of 4 to 8 carbon atoms interrupted by one nitrogen atom,
when x is 4,
R101 is hydrogen,
R102 is alkylene of 6 to 12 carbon atoms interrupted by two nitrogen atoms,
R103 is hydrogen, alkyl of 1 to 8 carbon atoms, said alkyl interrupted by one or two oxygen atoms, said alkyl substituted by a hydroxyl group, or both interrupted by one or two oxygen atoms and substituted by a hydroxyl group,
and Q is an alkali metal salt, ammonium or N+(G1)4,
and in formula R and R*
m is 2 or 3,
when m is 2, G is —(CH2CHR—O)rCH2CHR—, where r is 0 to 3, and R is hydrogen or methyl, and
when m is 3, G is glyceryl,
X is an inorganic or organic anion,
where the total charge of cations h is equal to the total charge of anions j.

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