GB1115596A - Uv absorbent light stable compounds and compositions containing the same - Google Patents
Uv absorbent light stable compounds and compositions containing the sameInfo
- Publication number
- GB1115596A GB1115596A GB3309066A GB3309066A GB1115596A GB 1115596 A GB1115596 A GB 1115596A GB 3309066 A GB3309066 A GB 3309066A GB 3309066 A GB3309066 A GB 3309066A GB 1115596 A GB1115596 A GB 1115596A
- Authority
- GB
- United Kingdom
- Prior art keywords
- represent
- group
- formula
- compounds
- alkylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title abstract 10
- 239000002250 absorbent Substances 0.000 title abstract 4
- 230000002745 absorbent Effects 0.000 title abstract 4
- 239000000203 mixture Substances 0.000 title abstract 2
- -1 polyethylene Polymers 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 150000002690 malonic acid derivatives Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- 229940081735 acetylcellulose Drugs 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 230000002152 alkylating effect Effects 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 230000001588 bifunctional effect Effects 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 229920002301 cellulose acetate Polymers 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 238000004040 coloring Methods 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 239000004922 lacquer Substances 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 239000002023 wood Substances 0.000 abstract 2
- BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 abstract 1
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical class OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 229920002396 Polyurea Polymers 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 125000004989 dicarbonyl group Chemical group 0.000 abstract 1
- HRXCHPZYXVOCBH-UHFFFAOYSA-N dioctadecyl propanedioate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CC(=O)OCCCCCCCCCCCCCCCCCC HRXCHPZYXVOCBH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000003951 lactams Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- BXSQRCPSLKYVLR-UHFFFAOYSA-N methyl 2-cyano-3-[4-[2-[4-(2-cyano-3-methoxy-3-oxo-1-phenylprop-1-enyl)phenoxy]ethoxy]phenyl]-3-phenylprop-2-enoate Chemical compound C1(=CC=CC=C1)C(=C(C(=O)OC)C#N)C1=CC=C(OCCOC2=CC=C(C=C2)C(=C(C#N)C(=O)OC)C2=CC=CC=C2)C=C1 BXSQRCPSLKYVLR-UHFFFAOYSA-N 0.000 abstract 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 abstract 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 229920006337 unsaturated polyester resin Polymers 0.000 abstract 1
- 238000004383 yellowing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/10—Esters of organic acids, i.e. acylates
- C08L1/12—Cellulose acetate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/28—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen, oxygen and sulfur
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/345—Nitriles
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/345—Nitriles
- D06M13/348—Nitriles unsaturated, e.g. acrylonitrile
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Polymeric materials have incorporated therein U.V. absorbent compounds of the general formula <FORM:1115596/C3/1> in which X1, X11, X2 and X12 independently of each other represent the groups -COR1 or -CN, wherein R1 represents the groups <FORM:1115596/C3/2> wherein the substituents R2, R3 and R4 contain none of the atom groupings -O-C-O-, -N-C-O- -N-C-S-, -C=C-O- and -C=C-N- and hereby R2 and R3 each represent an optionally substituted alkyl, alkenyl, cycloalkyl, aralkyl, monooxaaralkyl or aryl group, R4 represents an alkylene, monooxaalkylene or monothiaalkylene group. Y and Y1 each represent a bivalent radical of the formula -NHCO-, -NHSO2- or -NHCOO- which radical is attached to the ring A or B by the nitrogen atom, or Y and Y1 is -O-. R5 and R15 each represent an optionally substituted aryl group or, when all X1 are only -COR1 groups, they also represent hydrogen or, when at least two of the X's are cyano groups, they also represent an optionally substituted alkyl or aralkyl group. R6 represents an alkylene, mono- or dioxaalkylene, mono- or di-thia-alkylene, cycloalkylene, aralkylene, or mono-oxa-aralkylene group and, when Y or Y1 is a nitrogen-containing group, it also represents the phenylene group, whereby two or more hetero atoms present in or bound to R6 are separated from each other by at least 2 carbon atoms, and oxygen atoms bound to R6 and linking it to the benzene rings A and B are bound at saturated carbon atoms of R6, and n represents 2 or, when Y is oxygen, also 1, and the benzene rings A and B can be substituted by chemically inert and non-colouring substituents. An extensive list of polymers is given and examples refer to unsaturated polyester resin or methyl methacrylate polymerization being effected in the presence of the U.V. compound, and to polyvinyl chloride, polyethylene, polypropylene, polystyrene, polyurea, polyurethane, polyester amide including polymers of lactams and E-caprolactam, phenol-, urea-, and melamine formaldehyde, epoxides, acetyl cellulose compositions containing the U.V. absorbent compounds.ALSO:The invention comprises U.V. absorbing compounds of the general formula <FORM:1115596/C2/1> wherein X1, X11, X2 and X21 independently of each other represent the groups -COR1 or -CN, wherein R1 represents the groups <FORM:1115596/C2/2> wherein the substituents R2, R3 and R4 contain none of the atom groupings -O-C-O, -N-C-O, -N-C-S, -C = C-O and -C = C-N- and whereby R2 and R3 each represent an optionally substituted alkyl, alkenyl, cyclo-alkyl, aralkyl, mono-oxo-aralkyl or aryl group, R4 represents an alkylene, mono-oxa-alkylene or monothia-alkylene group, Y and Y1 each represent a bivalent radical of the formula -NHCO-, -NHSO2-or-NHCOO- which radical is attached to the ring A or B by the nitrogen atom, or Y and Y1 is -O-, R5 and R51 each represent an optionally substituted aryl group or, when all X's are only -COR1 groups, they also each represent hydrogen or, when at least two of the X's are cyano groups, they also represent an optionally substituted alkyl or aralkyl group, R6 represents an alkylene, mono- or di-oxa-alkylene, mono- or di-thia-alkylene, cycloalkylene, aralkylene, or mono-oxa-aralkylene group and, when Y or Y1 is a nitrogen-containing group, it also represents the phenylene group, whereby two or more hetero atoms present in or bound to R6 are separated from each other by at least 2 carbon atoms, and oxygen atoms bound to R6 and linking it to the benzene rings A and B are bound at saturated carbon atoms of R6, and n represents 2 or, when Y is oxygen, also 1, and the benzene rings. A and B can be substituted by chemically inert and non-colouring substituents. The compounds may be prepared: A by condensation of 1 mol of dicarbonyl compound of Formula II with 2 mols of identical or different malonic acid derivatives of Formulae III and IIIa <FORM:1115596/C2/3> <FORM:1115596/C2/4> under the known conditions for Knoevenagel condensation. In some cases, particularly if R5 or R51 is not hydrogen, an improvement is attained by converting the carbonyl compounds into the activated forms such as into the corresponding bis-dichlorides or bis-imines, and then reacting with the malonic acid derivatives. B. By reaction of 2 mols. of identical or different compounds of Formulae IV and IVa wherein Y1 and Y11 represent the hydroxyl or amino group, with 1 mol of a bifunctional alkylating or acylating agent of Formula V Z-R6-Z (V) wherein Z, when Y1 or Y11 is HO-, represents halogen, preferably the chlorine, bromine or iodine atoms or the radical of a strong oxygen-acid, preferably the radical of a sulphur-oxygen-acid, e.g. the radical -OSO3, -OSO2-low-alkyl or -OSO2-aryl and, when Y1 or Y11 are H2N-, Z represents the group -COZ1, -SO2Z1 or -OCOZ1, wherein Z1 is halogen, preferably the chlorine atom. Suitable alkylating agents of Formula V are bis-esters of diols of the formula HO-R6-OH which are derived from a hydrohalic acid or a strong oxygen acid. Suitable acylating agents are dicarboxylic acid halides. Method B can only be used for the synthesis of compounds in which n = 2. The dicarbonyl compounds of Formula II are obtained either by the usual aldehyde or ketone synthesis or, when n = 2, also by etherification or acylation of 1 mol of each of the corresponding carbonyl compounds of Formula VI and VIa by means of the bifunctional alkylating or acylating agents of Formula V. These carbonyl compounds of Formula VI or VIa can also first be condensed with the malonic acid derivatives of Formulae III and IIIa as described above for method A, to form the methylene malonic acid derivatives of Formulae IV and IVa which can be further reacted according to method B. Many compounds are exemplified. In one example malonic acid dioctadecyl ester produced by reacting malonic acid and stearyl alcohol is reacted with p-hydroxy benzaldehyde to produce p - (2,2 - dicarbo - octadecyloxy - ethenyl)-phenol which is reacted with dibromobutane to produce 1,4 - bis - [4 - (2,2 - dicarbo - octa - decyloxy-ethenyl)-phenoxy]-butane.ALSO:Wood veneer is treated with a lacquer which retards the natural yellowings of the wood, the lacquer comprising cellulose acetate polybutylacrylate, or nitro &c. and a UV absorbent compound, e.g. p-bis-[4-(2,2-dicarboethoxyethenyl)-phenoxy]-methyl]-benzene, 1, 2 - bis-[4-(1-phenyl-2-cyano- 2 -carbomethoxy - ethenyl)-phenoxy]-ethane, p, p\sv-bis (1-phenyl - -2-cyano-2-carboethoxy-ethenyl) diphenyl oxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1036665A CH442218A (en) | 1965-07-23 | 1965-07-23 | Process for protecting textile material against photodamage |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1115596A true GB1115596A (en) | 1968-05-29 |
Family
ID=4362452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3309066A Expired GB1115596A (en) | 1965-07-23 | 1966-07-22 | Uv absorbent light stable compounds and compositions containing the same |
Country Status (7)
| Country | Link |
|---|---|
| AT (2) | AT279593B (en) |
| BE (1) | BE684526A (en) |
| CH (1) | CH442218A (en) |
| DE (1) | DE1568693A1 (en) |
| ES (1) | ES329401A1 (en) |
| GB (1) | GB1115596A (en) |
| NL (2) | NL6610370A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997013749A3 (en) * | 1995-09-29 | 1997-06-26 | Allied Signal Inc | Novel cinnamamides and their use as stabilizers |
| EP1005855A1 (en) * | 1998-12-03 | 2000-06-07 | Basf Aktiengesellschaft | Dimer alpha-alkyl-styrene derivatives as photostable UV-filters for cometical or pharmaceutical compositions |
| FR2826365A1 (en) * | 2001-06-20 | 2002-12-27 | Oreal | PHOTOPROTECTIVE COSMETIC COMPOSITIONS CONTAINING AMIDE, SULFONAMIDE OR AROMATIC ACRYLONITRILE DERIVATIVES AND NOVEL AMIDE, SULFONAMIDE OR ACRYLONITRILE CARBAMATE DERIVATIVES |
| US6586506B2 (en) | 1998-10-12 | 2003-07-01 | Clariant Finance (Bvi) Limited | Colored wax articles |
| GB2458362A (en) * | 2008-03-13 | 2009-09-23 | Ciba Holding Inc | Dimeric benzylidene malonates and derivatives thereof for use as UV-light absorbers in cosmetics |
| WO2010056452A3 (en) * | 2008-11-14 | 2010-07-29 | Cytec Technology Corp. | Dimeric cyanoacrylate compounds as red-shifted uv absorbers |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5138089A (en) * | 1986-06-27 | 1992-08-11 | The Procter & Gamble Company | Chromophores, sunscreen compositions and methods for preventing sunburn |
| US4749774A (en) * | 1986-12-29 | 1988-06-07 | Eastman Kodak Company | Condensation polymer containing the residue of a poly-methine compound and shaped articles produced therefrom |
| US5068348A (en) * | 1988-04-18 | 1991-11-26 | Eastman Kodak Company | Triazole methine compounds |
| US4958043A (en) * | 1988-04-18 | 1990-09-18 | Eastman Kodak Company | Novel methine compounds, polymers containing them and formed articles therefrom |
| US5075491A (en) * | 1988-04-18 | 1991-12-24 | Eastman Kodak Company | Methine compounds containing ester group |
| US5086161A (en) * | 1988-04-18 | 1992-02-04 | Eastman Kodak Company | Novel methine compounds, polymers containing them and formed articles therefrom |
-
0
- NL NL134694D patent/NL134694C/xx active
-
1965
- 1965-07-23 CH CH1036665A patent/CH442218A/en unknown
-
1966
- 1966-07-22 NL NL6610370A patent/NL6610370A/xx unknown
- 1966-07-22 BE BE684526A patent/BE684526A/xx unknown
- 1966-07-22 GB GB3309066A patent/GB1115596A/en not_active Expired
- 1966-07-22 AT AT320666A patent/AT279593B/en not_active IP Right Cessation
- 1966-07-22 DE DE1966G0047504 patent/DE1568693A1/en active Pending
- 1966-07-22 ES ES0329401A patent/ES329401A1/en not_active Expired
- 1966-07-22 AT AT703866A patent/AT272660B/en active
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997013749A3 (en) * | 1995-09-29 | 1997-06-26 | Allied Signal Inc | Novel cinnamamides and their use as stabilizers |
| US6586506B2 (en) | 1998-10-12 | 2003-07-01 | Clariant Finance (Bvi) Limited | Colored wax articles |
| EP1005855A1 (en) * | 1998-12-03 | 2000-06-07 | Basf Aktiengesellschaft | Dimer alpha-alkyl-styrene derivatives as photostable UV-filters for cometical or pharmaceutical compositions |
| US6159455A (en) * | 1998-12-03 | 2000-12-12 | Basf Aktiengesellschaft | Dimeric α-alkylstyrene derivatives as photostable UV filters in cosmetic and pharmaceutical preparations |
| FR2826365A1 (en) * | 2001-06-20 | 2002-12-27 | Oreal | PHOTOPROTECTIVE COSMETIC COMPOSITIONS CONTAINING AMIDE, SULFONAMIDE OR AROMATIC ACRYLONITRILE DERIVATIVES AND NOVEL AMIDE, SULFONAMIDE OR ACRYLONITRILE CARBAMATE DERIVATIVES |
| EP1269979A1 (en) * | 2001-06-20 | 2003-01-02 | L'oreal | Aromatic amide, sulfonamide or carbamate acrylonitrile derivatives and photoprotective cosmetic compositions containing them |
| US6749839B2 (en) | 2001-06-20 | 2004-06-15 | L'oreal | Photoprotective cosmetic compositions containing aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile and novel aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile |
| US7255853B2 (en) | 2001-06-20 | 2007-08-14 | L'oreal | Photoprotective cosmetic compositions containing aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile and novel aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile |
| US7390916B2 (en) | 2001-06-20 | 2008-06-24 | L'oreal | Photoprotective cosmetic compositions containing aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile and novel aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile |
| GB2458362A (en) * | 2008-03-13 | 2009-09-23 | Ciba Holding Inc | Dimeric benzylidene malonates and derivatives thereof for use as UV-light absorbers in cosmetics |
| WO2010056452A3 (en) * | 2008-11-14 | 2010-07-29 | Cytec Technology Corp. | Dimeric cyanoacrylate compounds as red-shifted uv absorbers |
Also Published As
| Publication number | Publication date |
|---|---|
| NL134694C (en) | |
| AT272660B (en) | 1969-07-10 |
| ES329401A1 (en) | 1967-08-16 |
| DE1568693A1 (en) | 1970-03-19 |
| BE684526A (en) | 1967-01-23 |
| CH442218A (en) | 1968-01-31 |
| AT279593B (en) | 1970-03-10 |
| NL6610370A (en) | 1967-01-24 |
| CH1036665A4 (en) | 1967-05-13 |
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