US4404150A
Expired / Lapsed
US
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Cyclic pyrophosphate derivatives and their preparation
Assignee: Sankin Industry Co Ltd
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Filing: 1981-02-05
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Granted: 1983-09-13
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Expires: 2001-02-05
Abstract
Abstract A cyclic pyrophosphate derivative having the formula ##STR1## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents alkyl, acryloyloxy lower alkyl or methacryloyloxy lower alkyl in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy; a method of preparing the same, a dental filling material comprising the same and a method of filling dental cavities are disclosed.
Inventors
- 👤 Masayoshi Tsunekawa
- 👤 Nobuyoshi Miyoshi
- 👤 Tamotsu Komura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 23:23
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6564; C07F9/6578; C07F9/06; C07F9/08; C07F9/09; C07F9/098; C07F9/6571; C07F9/6574
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
73 words
A cyclic pyrophosphate derivative having the formula (I): ##STR24## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents allyl, acryloyloxy lower alkyl or methacryloxy lower alkyl, in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy.
Claim 2
Dependent Claim
73 words
A cyclic pyrophosphate derivative having the formula (I): ##STR24## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents allyl, acryloyloxy lower alkyl or methacryloxy lower alkyl, in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy.
Claim 3
Dependent Claim
18 words
The cyclic pyrophosphate according to claim 1, wherein A is a direct bond between the two penyl rings.
Claim 4
Dependent Claim
12 words
The cyclic pyrophosphate according to claim 1, wherein A is dimethyl methylene.
Claim 5
Dependent Claim
12 words
The cyclic pyrophosphate according to claim 1, wherein A is phenyl methylene.
Claim 6
Dependent Claim
11 words
The cyclic pyrophosphate according to claim 1, wherein A is sulfonyl.
Claim 7
Dependent Claim
11 words
The cyclic pyrophosphate according to claim 1, wherein A is oxy.
Claim 8
Dependent Claim
11 words
The cyclic pyrophosphate according to claim 1, wherein A is cyclohexylidene.
Claim 9
Dependent Claim
13 words
The cyclic pyrophosphate according to claim 1, wherein every R 2 is hydrogen.
Claim 10
Dependent Claim
16 words
The cyclic pyrophosphate according to claim 1, wherein two of the R 2 groups are halogen.
Claim 11
Dependent Claim
13 words
The cyclic pyrophosphate according to claim 1, wherein every R 2 is halogen.
Claim 12
Dependent Claim
12 words
The cyclic pyropshophate according to claim 1, wherein R 1 is allyl.
Claim 13
Dependent Claim
13 words
The cyclic pyrophosphate according to claim 1, wherein R 1 is 2-methacryloyloxy ethyl.
Claim 14
Dependent Claim
13 words
The cyclic pyrophosphate according to claim 1, wherein R 1 is 1-methyl-2-methacryloyloxy ethyl.
Claim 15
Dependent Claim
13 words
The cyclic pyrophosphate according to claim 1, wherein R 1 is 2-halo-3-methacryloyloxy ethyl.
Claim 16
Dependent Claim
13 words
The cyclic pyrophosphate according to claim 1, wherein R 1 is acryloyloxy ethyl.
Claim 17
Dependent Claim
163 words
A process for the production of cyclic pyrophosphate derivatives having the formula (I) ##STR25## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents allyl, acryloyloxy lower alkyl or methacryloyloxy lower alkyl, in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy; the process comprising: reacting, under anhydrous conditions, a phenol derivative having the formula (II) ##STR26## with a phosphoryl halide to give the phosphoryl dihalide derivative having the formula (III) ##STR27## wherein X is halogen; adding to the phosphoryl dihalide derivative having the formula (III), under anhydrous conditions, an alcohol having the formula R.sup.1 --OH to obtain a phosphoryl halide derivative having the formula (IV) ##STR28## which is then hydrolyzed, in the presence of a base, to provide the cyclic pyrophosphate derivative having the formula (I).
Claim 18
Dependent Claim
163 words
A process for the production of cyclic pyrophosphate derivatives having the formula (I) ##STR25## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents allyl, acryloyloxy lower alkyl or methacryloyloxy lower alkyl, in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy; the process comprising: reacting, under anhydrous conditions, a phenol derivative having the formula (II) ##STR26## with a phosphoryl halide to give the phosphoryl dihalide derivative having the formula (III) ##STR27## wherein X is halogen; adding to the phosphoryl dihalide derivative having the formula (III), under anhydrous conditions, an alcohol having the formula R.sup.1 --OH to obtain a phosphoryl halide derivative having the formula (IV) ##STR28## which is then hydrolyzed, in the presence of a base, to provide the cyclic pyrophosphate derivative having the formula (I).
Claim 19
Dependent Claim
15 words
The process according to claim 16, wherein the base, present during hydrolysis, is an amine.
References Cited (Backward Citations)
US3476699A
Cited
GB2082184A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-09-12 | 1987-03-14 | 1987-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-09-12 | 1991-03-14 | 1991-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-09-12 | 1995-03-14 | 1995-09-13 | $7700.00 | Window Closed / Lapsed |