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US4189409A
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Process for preparing a methylenebis(2-hydroxy-4-alkoxybenzophenone) and acyloxymethyl 2-OH 4-alkoxy benzophenones
Assignee: Argus Chemical Corp
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Filing: 1978-07-14
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Granted: 1980-02-19
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Expires: 1998-07-14
Abstract
Abstract A novel process is provided for preparing a methylenebis(2-hydroxy-4-alkoxybenzophenone), comprising forming a novel 2-hydroxy-4-alkoxyacyloxymethylbenzophenone by a reaction of a 2-hydroxy-4-alkoxybenzophenone with a carboxylic acid and formaldehyde, and causing the 2-hydroxy-4-alkoxyacyloxymethylbenzophenone to react with a 2-hydroxy-4-alkoxybenzophenone in the presence of an acid catalyst. Both the acyloxymethylhydroxyalkoxybenzophenone and methylenebis(2-hydroxy-4-alkoxybenxophenone) which are prepared according to this invention are useful to prevent-degradation of organic materials, particularly as light stabilizers for synthetic resins.
Inventors
- 👤 Motonobu Minagawa
- 👤 Naohiro Kubota
- 👤 Toshihiro Shibata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 04:20
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C49/00; C07C49/76; C07C49/84; C08; C08K; C08K5/00; C08K5/04; C08K5/13; C08K5/132
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
52 words
A 2-hydroxy-4-alkoxyacyloxymethylbenzophenone represented by the formula: ##STR14## in which R is an alkyl group having 1 to 12 carbon atoms, and R 1 and R 2 are independently hydrogen atoms or saturated aliphatic acyloxymethyl groups having 2 to 9 carbon atoms, provided that R 1 and R 2 are not simultaneously hydrogen.
Claim 2
Dependent Claim
52 words
A 2-hydroxy-4-alkoxyacyloxymethylbenzophenone represented by the formula: ##STR14## in which R is an alkyl group having 1 to 12 carbon atoms, and R 1 and R 2 are independently hydrogen atoms or saturated aliphatic acyloxymethyl groups having 2 to 9 carbon atoms, provided that R 1 and R 2 are not simultaneously hydrogen.
Claim 3
Dependent Claim
11 words
A 2-hydroxy-4-alkoxyacyloxymethylbenzophenone according to claim 1 in which R is methyl.
Claim 4
Dependent Claim
11 words
A 2-hydroxy-4-alkoxyacyloxymethylbenzophenone according to claim 1 in which R is n-octyl.
Claim 5
Dependent Claim
19 words
A 2-hydroxy-4-alkoxyacyloxymethylbenzophenone according to claim 1 in which at least one of R 1 and R 2 is acetoxymethyl.
Claim 6
Dependent Claim
19 words
A 2-hydroxy-4-alkoxy-acyloxymethylbenzophenone according to claim 1 in which at least one of R 1 and R 2 is propionoxymethyl.
Claim 7
Dependent Claim
66 words
A process for preparing a methylenebis(2-hydroxy-4-alkoxybenzophenone) represented by the formula: ##STR15## in which R is an alkyl group having 1 to 12 carbon atoms comprising the steps of treating a 2-hydroxy-4-alkoxyacyloxymethylbenzophenone of claim 1 with a 2-hydroxy-4-alkoxybenzophenone represented by the formula: ##STR16## in which R is an alkyl group having 1 to 12 carbon atoms in the presence of an acid catalyst, and recovering the methylenebis(2-hydroxy-4-alkoxybenzophenone).
Claim 8
Dependent Claim
13 words
A process according to claim 6 in which the methylenebis(2-hydroxy-4-alkoxybenzophenone) is a 5,5'-methylenebis(2-hydroxy-4-alkoxymethylbenzophenone).
Claim 9
Dependent Claim
18 words
A process according to claim 6 in which the methylenebis(2-hydroxy-4-alkoxybenzophenone) is a mixture containing 5,5'-, 3,5'-, and 3,3'-methylenebis(2-hydroxyalkoxybenzophenone).
Claim 10
Dependent Claim
35 words
A stabilizer synthetic resin composition having increased resistance to deterioration on exposure to light of wavelength less than 400 nanometers, comprising a synthetic resin and 0.01 to 1% of a 2-hydroxy-4-alkoxyacyloxymethylbenzophenone according to claim 1.
Claim 11
Dependent Claim
30 words
A stabilized synthetic resin composition according to claim 9 in which the synthetic resin is vinyl chloride polymer, a styrenated polyester, or a copolymer of acrylonitrile with butadiene and sytrene.
Claim 12
Dependent Claim
69 words
A stabilizer composition capable of enhancing the resistance to deterioration on exposure of a synthetic resin to light of wavelength less than 400 nanometers comprising a 2-hydroxy-4-alkoxyacyloxymethylbenzophenone according to claim 1 and from 0.1 to 10 parts by weight per part of 2-hydroxy-4-alkoxyacyloxymethylbenzophenone of a known polymer stabilizer selected from the group consisting of phenols, quinones, quaternary ammonium, halides, polyvalent metal salts of carboxylic acids, organic phosphites, and 1,2-epoxides.
Claim 13
Dependent Claim
15 words
A stabilizer composition according to claim 11 in which the polymer stabilizer is a phenol.
Claim 14
Dependent Claim
15 words
A stabilizer composition according to claim 11 in which the polymer stabilizer is a quinone.
Claim 15
Dependent Claim
27 words
A stabilizer composition according to claim 11 in which the polymer stabilizer is a polyvalent metal salt of a monocarboxylic acid having 6 to 24 carbon atoms.
Claim 16
Dependent Claim
16 words
A stabilizer composition according to claim 11 in which the polymer stabilizer is an organic phosphite.
Claim 17
Dependent Claim
15 words
A stabilizer composition according to claim 11 in which the polymer stabilizer is a 1,2-epoxide.
Claim 18
Dependent Claim
12 words
A process according to claim 6 in which the methylenebis-2-hydroxy-4-alkoxybenzophenone) is 5,5'-methylenebis(2-hydroxy-4-methoxybenzophenone).
Claim 19
Dependent Claim
12 words
A process according to claim 6 in which the methylenebis-(2-hydroxy-4-alkoxybenzophenone) is 5,5'-methylenebis(2-hydroxy-4-n-octyloxybenzophenone).
Claim 20
Dependent Claim
26 words
A process according to claim 6 in which the methylenebis-(2-hydroxy-4-alkoxybenzophenone) is an unsymmetrical methylenebis(2-hydroxy-4-alkoxybenzophenone) with two dissimilar alkoxy groups each having one to twelve carbon atoms.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-02-18 | 1983-08-20 | 1984-02-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-18 | 1987-08-20 | 1988-02-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-18 | 1991-08-20 | 1992-02-19 | $7700.00 | Window Closed / Lapsed |