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US4218392A Expired / Lapsed US ⏱️ 0.0 years remaining

Two-step method of making copolymerizable, ultraviolet light absorber _2-cyano-3,3-diphenylacryloxy) alkylene acrylic acid esters

Assignee: ISP Investments LLC
•
Filing: 1979-05-16
•
Granted: 1980-08-19
•
Expires: 1999-05-16
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Abstract

Abstract This invention relates to a method of making in high yield light absorber compounds which are (2-cyano-3,3-diphenylacryloxy) alkylene acrylic acid esters having the formula: ##STR1## where (Ar) 1 and (Ar) 2 are aromatic carbocyclic nuclei of the benzene and naphthalene series and are independently selected from phenyl or phenyl substituted with alkyl, halo, alkoxy, carboxy, carbalkoxy, cyano, acetyl, benzoyl, phenyl, alkyl phenyl, phenoxy phenyl, alkyl substituted phenoxy, or alkoxy phenyl substituted phenyl and naphthyl; X is alkylene, C 2 -C 17 , unsubstituted or substituted with halo, cyano, alkyl C 1 -C 6 alkoxy C 1 -C 6 , alkoxyalkyl C 1 -C 6 , or alkoxyalkyleneoxy C 1 -C 6 ; and Y is copolymerizable radical selected from acryloyl C 3 -C 12 alkylacryloyl C 3 -C 12 , acryloxyalkyl C 3 -C 12 , acryloxyhydroxyalkyl and alkylacryloxyhydroxyalkyl C 3 -C 12 . The method comprises: (a) esterifying a hydroxyalkylene cyanoacetate with an acryloylhalide or acrylic acid to form a (2-acryloxyalkyl) 2-cyanoacetate intermediate, and, (b) condensing the intermediate directly with a benzophenone to provide the desired product.

Inventors

  • 👤 Donald H. Lorenz
  • 👤 Bruce A. Gruber

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 11:57
CPC Classifications
C; C07; C07C; C07C255/00; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 219 words
A method of making copolymerizable ultraviolet light absorber (2-cyano-3,3-diphenylacryloxy) alkylene acrylic acid esters in high yield having the formula: ##STR12## where (Ar) 1 and (Ar) 2 are aromatic carbocyclic nuclei of the benzene and naphthalene series and are independently selected from phenyl or phenyl substituted with alkyl, halo, alkoxy, carboxy, carbalkoxy, cyano, acetyl, benzoyl, phenyl, alkyl phenyl, phenoxy phenyl, alkyl substituted phenoxy, or alkoxy phenyl substituted phenyl, and naphthyl; X is alkylene, C 2 -C 17 , unsubstituted or substituted with halo, cyano, alkyl C 1 -C 6 , alkoxy C 1 -C 6 , alkoxyalkyl C 1 -C 6 , or alkoxyalkyleneoxy C 1 -C 6 ; and, Y is copolymerizable radical selected from acryloyl C 3 -C 12 , alkylacryloyl C 3 -C 12 , acryloxyalkyl C 3 -C 12 , acryloxyhydroxyalkyl and alkylacryloxyhydroxyalkyl C 3 -C 12 , which comprises the steps of: (a) esterifying a hydroxyalkylene cyanoacetate having the formula: ##STR13## where X is as defined above, with an acryloyl halide or acrylic acid having the formula YZ, where Y is as defined above and Z is a halide or hydroxyl group to form a (2-acryloxyalkyl) 2-cyanoacetate intermediate, and, (b) condensing the intermediate with a benzophenone having the formula: ##STR14## where (Ar) 1 and (Ar) 2 are as defined above, to form the desired compound.
Claim 2
Independent Claim 219 words
A method of making copolymerizable ultraviolet light absorber (2-cyano-3,3-diphenylacryloxy) alkylene acrylic acid esters in high yield having the formula: ##STR12## where (Ar) 1 and (Ar) 2 are aromatic carbocyclic nuclei of the benzene and naphthalene series and are independently selected from phenyl or phenyl substituted with alkyl, halo, alkoxy, carboxy, carbalkoxy, cyano, acetyl, benzoyl, phenyl, alkyl phenyl, phenoxy phenyl, alkyl substituted phenoxy, or alkoxy phenyl substituted phenyl, and naphthyl; X is alkylene, C 2 -C 17 , unsubstituted or substituted with halo, cyano, alkyl C 1 -C 6 , alkoxy C 1 -C 6 , alkoxyalkyl C 1 -C 6 , or alkoxyalkyleneoxy C 1 -C 6 ; and, Y is copolymerizable radical selected from acryloyl C 3 -C 12 , alkylacryloyl C 3 -C 12 , acryloxyalkyl C 3 -C 12 , acryloxyhydroxyalkyl and alkylacryloxyhydroxyalkyl C 3 -C 12 , which comprises the steps of: (a) esterifying a hydroxyalkylene cyanoacetate having the formula: ##STR13## where X is as defined above, with an acryloyl halide or acrylic acid having the formula YZ, where Y is as defined above and Z is a halide or hydroxyl group to form a (2-acryloxyalkyl) 2-cyanoacetate intermediate, and, (b) condensing the intermediate with a benzophenone having the formula: ##STR14## where (Ar) 1 and (Ar) 2 are as defined above, to form the desired compound.
Claim 3
Dependent Claim 16 words
A method according to claim 1 in which both (Ar) 1 and (Ar) 2 are phenyl.
Claim 4
Dependent Claim 16 words
A method according to claim 1 in which X is alkylene, C 2 -C 6 .
Claim 5
Dependent Claim 15 words
A method according to claim 1 in which Y is acryloyl, methacryloyl, 3-acryloxy-2-hydroxypropyl or 3-methacryloxy-2-hydroxypropyl.
Claim 6
Dependent Claim 31 words
A method according to claim 1 in which both (Ar) 1 and (Ar) 2 are phenyl, x is alkylene, C 2 -C 6 and Y is acryloyl, methacryloyl, 3-acryoxy-2-hydroxypropyl or 3-methacryloxy-2-hydroxypropyl.
Claim 7
Dependent Claim 13 words
A method according to claim 1 in which YZ is an acryloyl halide.
Claim 8
Dependent Claim 13 words
A method according to claim 1 in which YZ is an acrylic acid.

References Cited (Backward Citations)

US3644466A Cited
US3993684A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-08-19 1984-02-18 1984-08-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-08-19 1988-02-18 1988-08-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-08-19 1992-02-18 1992-08-19 $7700.00 Window Closed / Lapsed

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