US4077860A
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Photopolymerizable composition stabilized with ammonium salts of phosphorus acid and process
Assignee: Stauffer Chemical Co
•
Filing: 1976-12-29
•
Granted: 1978-03-07
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Expires: 1996-12-29
Abstract
Abstract A stabilized photopolymerizable composition comprising photopolymerizable ethylenically unsaturated monomeric compounds, a photoinitiator and at least one organic ammonium salt of phosphorus acid as a stabilizer.
Inventors
- 👤 Francis A. Via
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 22:54
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50
Claims Analysis
Total Claims: 56
Claim 1
Independent Claim
116 words
A process for preparing a photopolymerizable composition comprising forming a mixture containing a photopolymerizable ethylenically unsaturated compound, a benzoin ether in an amount sufficient to initiate photopolymerization and a stabilizing amount of an ammonium salt of a phosphorus acid having the formula ##STR46## wherein R is hydrocarbyl or thiophenealkylene; R',r" and R"' are a. independently selected hydrocarbyl; or b. together are part of a heterocyclic amino radical in which the quaternary nitrogen in the formula is part of the ring; X is oxygen or sulfur; Y and Y' are independently selected alkoxy, thioalkoxy, alkenyloxy, thioalkenyloxy, alkyl, carboalkoxyalkyl, phenylalkyl, phenyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy, or alkylthiophenoxy; Z is oxygen or sulfur; and m is 1 or 2.
Claim 2
Dependent Claim
116 words
A process for preparing a photopolymerizable composition comprising forming a mixture containing a photopolymerizable ethylenically unsaturated compound, a benzoin ether in an amount sufficient to initiate photopolymerization and a stabilizing amount of an ammonium salt of a phosphorus acid having the formula ##STR46## wherein R is hydrocarbyl or thiophenealkylene; R',r" and R"' are a. independently selected hydrocarbyl; or b. together are part of a heterocyclic amino radical in which the quaternary nitrogen in the formula is part of the ring; X is oxygen or sulfur; Y and Y' are independently selected alkoxy, thioalkoxy, alkenyloxy, thioalkenyloxy, alkyl, carboalkoxyalkyl, phenylalkyl, phenyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy, or alkylthiophenoxy; Z is oxygen or sulfur; and m is 1 or 2.
Claim 3
Dependent Claim
48 words
The process of claim 1 wherein, in said formula, R is alkyl, aryl, aralkyl, or thiophenealkylene; R', R" and R"' are independently selected alkyl or together are part of a heterocyclic amino radical of from 5 to 9 carbon atoms; and Y and Y' are alkoxy or phenoxy.
Claim 4
Dependent Claim
52 words
The process of claim 2 wherein said benzoin ether is present in said composition at a concentration of about 0.01 to about 30 percent by weight, and said ammonium salt of a phosphorus acid is present at a concentration of about 0.01 to about 20 percent by weight of said benzoin ether.
Claim 5
Dependent Claim
29 words
The process of claim 3 wherein R,R', R" and R"' in said formula are independently selected alkyl of 1 to 20 carbon atoms and Y and Y' are phenoxy.
Claim 6
Dependent Claim
19 words
The process of claim 4 wherein said ammonium salt of a phosphorus acid is tridodecyl methyl ammonium diphenyl phosphate.
Claim 7
Dependent Claim
19 words
The process of claim 4 wherein said ammonium salt of a phosphorus acid is hexadecyl trimethyl ammonium diphenyl phosphate.
Claim 8
Dependent Claim
19 words
The process of claim 4 wherein said ammonium salt of a phosphorus acid is dodecyl trimethyl ammonium diphenyl phosphate.
Claim 9
Dependent Claim
20 words
The process of claim 4 wherein said ammonium salt of a phosphorus acid is tri iso-octyl methyl ammonium diphenyl phosphate.
Claim 10
Dependent Claim
34 words
The process of claim 3 wherein R is lower alkyl; R', R" and R"' are part of a heterocyclic amino radical of from 5 to 9 carbon atoms; and Y and Y' are phenoxy.
Claim 11
Dependent Claim
18 words
The process of claim 9 wherein said ammonium salt of a phosphorus acid is N-methyl pyridinium diphenyl phosphate.
Claim 12
Dependent Claim
18 words
The process of claim 9 wherein said ammonium salt of a phosphorus acid is N-methyl benzoltriazolium diphenyl phosphate.
Claim 13
Dependent Claim
17 words
The process of claim 9 wherein said ammonium salt of a phosphorus acid has the formula ##STR47##
Claim 14
Dependent Claim
31 words
The process of claim 3 wherein R,R',R" and R"' are alkyl of 1 to 16 carbon atoms, and Y and Y' are alkoxy or carboalkoxyalkyl of 1 to 10 carbon atoms.
Claim 15
Dependent Claim
19 words
The process of claim 13 wherein said ammonium salt of a phosphorus acid is dodecyl trimethyl ammonium dibutyl phosphate.
Claim 16
Dependent Claim
19 words
The process of claim 13 wherein said ammonium salt of a phosphorus acid is dodecyl trimethyl ammonium dibutyl phosphonate.
Claim 17
Dependent Claim
17 words
The process of claim 13 wherein said ammonium salt of a phosphorus acid is methyl methoxycarbonylethyl phosphate.
Claim 18
Dependent Claim
19 words
The process of claim 13 wherein said ammonium salt of a phosphorus acid is methyl triethyl ammonium dimethyl phosphate.
Claim 19
Dependent Claim
20 words
The process of claim 13 wherein said ammonium salt of a phosphorus acid is hexadecyl butyl dimethyl ammonium dibutyl phosphate.
Claim 20
Dependent Claim
17 words
The process of claim 13 wherein said ammonium salt of a phosphorus acid has the formula ##STR48##
Claim 21
Dependent Claim
24 words
The process of claim 13 wherein R is a C 12 group, R', R" and R"' are methyl and Y and Y' are octyl.
Claim 22
Dependent Claim
29 words
The process of claim 13 wherein R is dodecyl, R', R" and R"' are methyl, Y and Y' are decyl and m is a mixture of 1 and 2.
Claim 23
Dependent Claim
35 words
The process of claim 3 wherein R is thiophenealkylene where the alkylene has 1 to 4 carbon atoms or aralkyl of 7 to 11 carbon atoms; R', R", R"', Y and Y" are lower alkyl.
Claim 24
Dependent Claim
19 words
The process of claim 22 wherein said ammonium salt of a phosphorus acid is benzyl trimethyl ammonium dimethyl phosphate.
Claim 25
Dependent Claim
19 words
The process of claim 22 wherein said ammonium salt of a phosphorus acid is thiophenemethylene trimethyl ammonium dimethyl phosphate.
Claim 26
Dependent Claim
17 words
The process of claim 3 wherein the ethylenically unsaturated compounds consist essentially of derivatives of acrylic acid.
Claim 27
Dependent Claim
114 words
In a process for preparing a photopolymerizable composition comprising at least one photopolymerizable ethylenically unsaturated compound and a photoinitiating compound, the improvement which comprises incorporating a stabilizing amount of an ammonium salt of a phosphorus acid having the formula ##STR49## wherein R is hydrocarbyl or thiophenealkylene; R', r" and R"' are a. independently selected hydrocarbyl; or b. together are part of a heterocyclic amino radical in which the quaternary nitrogen in the formula is part of the ring; X is oxygen or sulfur; Y and Y' are independently selected alkoxy, thioalkoxy, alkenyloxy, thioalkenyloxy, alkyl, carboalkoxyalkyl, phenylalkyl, phenyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy, or alkylthiophenoxy; Z is oxygen or sulfur; and m is 1 or 2.
Claim 28
Dependent Claim
114 words
In a process for preparing a photopolymerizable composition comprising at least one photopolymerizable ethylenically unsaturated compound and a photoinitiating compound, the improvement which comprises incorporating a stabilizing amount of an ammonium salt of a phosphorus acid having the formula ##STR49## wherein R is hydrocarbyl or thiophenealkylene; R', r" and R"' are a. independently selected hydrocarbyl; or b. together are part of a heterocyclic amino radical in which the quaternary nitrogen in the formula is part of the ring; X is oxygen or sulfur; Y and Y' are independently selected alkoxy, thioalkoxy, alkenyloxy, thioalkenyloxy, alkyl, carboalkoxyalkyl, phenylalkyl, phenyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy, or alkylthiophenoxy; Z is oxygen or sulfur; and m is 1 or 2.
Claim 29
Dependent Claim
112 words
A photopolymerizable composition comprising at least one photopolymerizable ethylenically unsaturated compound containing a benzoin ether in an amount sufficient to initiate photopolymerization and a stabilizing amount of an ammonium salt of a phosphorus acid having the formula ##STR50## wherein R is hydrocarbyl or thiophenealkylene; R', r" and R"' are a. independently selected hydrocarbyl; or b. together are part of a heterocyclic amino radical in which the quaternary nitrogen in the formula is part of the ring; X is oxygen or sulfur; Y and Y' are independently selected alkoxy, thioalkoxy, alkenyloxy, thioalkenyloxy, alkyl, alkylcarboxyalkyl, phenylalkyl, phenyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy, or alkylthiophenoxy; Z is oxygen or sulfur; and m is 1 or 2.
Claim 30
Dependent Claim
112 words
A photopolymerizable composition comprising at least one photopolymerizable ethylenically unsaturated compound containing a benzoin ether in an amount sufficient to initiate photopolymerization and a stabilizing amount of an ammonium salt of a phosphorus acid having the formula ##STR50## wherein R is hydrocarbyl or thiophenealkylene; R', r" and R"' are a. independently selected hydrocarbyl; or b. together are part of a heterocyclic amino radical in which the quaternary nitrogen in the formula is part of the ring; X is oxygen or sulfur; Y and Y' are independently selected alkoxy, thioalkoxy, alkenyloxy, thioalkenyloxy, alkyl, alkylcarboxyalkyl, phenylalkyl, phenyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy, or alkylthiophenoxy; Z is oxygen or sulfur; and m is 1 or 2.
Claim 31
Dependent Claim
48 words
The composition of claim 27, wherein, in said formula, R is alkyl, aryl, aralkyl, or thiophenealkylene R', R" and R"' are independently selected alkyl or together are part of a heterocyclic amino radical of from 5 to 9 carbon atoms; and Y and Y' are alkoxy or phenoxy.
Claim 32
Dependent Claim
52 words
The composition of claim 28 wherein said benzoin ether is present in said composition at a concentration of about 0.01 to about 30 percent by weight, and said ammonium salt of a phosphorus acid is present at a concentration of about 0.01 to about 20 percent by weight of said benzoin ether.
Claim 33
Dependent Claim
29 words
The composition of claim 29 wherein R,R', R" and R"' in said formula are independently selected alkyl of 1 to 20 carbon atoms and Y and Y' are phenoxy.
Claim 34
Dependent Claim
19 words
The composition of claim 30 wherein said ammonium salt of a phosphorus acid is tridodecyl methyl ammonium diphenyl phosphate.
Claim 35
Dependent Claim
19 words
The composition of claim 30 wherein said ammonium salt of a phosphorus acid is hexadecyl trimethyl ammonium diphenyl phosphate.
Claim 36
Dependent Claim
19 words
The composition of claim 30 wherein said ammonium salt of a phosphorus acid is dodecyl trimethyl ammonium diphenyl phosphate.
Claim 37
Dependent Claim
20 words
The composition of claim 30 wherein said ammonium salt of a phosphorus acid is tri iso-octyl methyl ammonium diphenyl phosphate.
Claim 38
Dependent Claim
34 words
The composition of claim 29 wherein R is lower alkyl; R', R" and R"' are part of a heterocyclic amino radical of from 5 to 9 carbon atoms; and Y and Y' are phenoxy.
Claim 39
Dependent Claim
18 words
The composition of claim 35 wherein said ammonium salt of a phosphorus acid is N-methyl pyridinium diphenyl phosphate.
Claim 40
Dependent Claim
18 words
The composition of claim 35 wherein said ammonium salt of a phosphorus acid is N-methyl benzoltriazolium diphenyl phosphate.
Claim 41
Dependent Claim
17 words
The composition of claim 35 wherein said ammonium salt of a phosphorus acid has the formula ##STR51##
Claim 42
Dependent Claim
31 words
The composition of claim 29 wherein R,R',R" and R"' are alkyl of 1 to 16 carbon atoms; and Y and Y' are alkoxy or carboalkoxyalkyl of 1 to 10 carbon atoms.
Claim 43
Dependent Claim
19 words
The composition of claim 39 wherein said ammonium salt of a phosphorus acid is dodecyl trimethyl ammonium dibutyl phosphate.
Claim 44
Dependent Claim
19 words
The composition of claim 39 wherein said ammonium salt of a phosphorus acid is dodecyl trimethyl ammonium dibutyl phosphate.
Claim 45
Dependent Claim
17 words
The composition of claim 39 wherein said ammonium salt of a phosphorus acid is methyl methoxycarbonylethyl phosphate.
Claim 46
Dependent Claim
19 words
The composition of claim 39 wherein said ammonium salt of a phosphorus acid is methyl triethyl ammonium dimethyl phosphate.
Claim 47
Dependent Claim
20 words
The composition of claim 39 wherein said ammonium salt of a phosphorus acid is hexadecyl butyl dimethyl ammonium dibutyl phosphate.
Claim 48
Dependent Claim
17 words
The composition of claim 39 wherein said ammonium salt of a phosphorus acid has the formula ##STR52##
Claim 49
Dependent Claim
24 words
The composition of claim 39 wherein R is a C 12 group, R', R" and R"' are methyl and Y and Y' are octyl.
Claim 50
Dependent Claim
28 words
The composition of claim 39 wherein R is dodecyl, R',R" and R"' are methyl, Y and Y' are decyl and m is a mixture of 1 and 2.
Claim 51
Dependent Claim
35 words
The composition of claim 29 wherein R is thiophenealkylene where the alkylene has 1 to 4 carbon atoms or aralkyl of 7 to 11 carbon atoms; R', R", R"', Y and Y" are lower alkyl.
Claim 52
Dependent Claim
18 words
The composition of claim 48 wherein said ammonium salt of a phosphorus acid is benzyltrimethyl ammonium dimethyl phosphate.
Claim 53
Dependent Claim
19 words
The composition of claim 49 wherein said ammonium salt of a phosphorus acid is thiophenemethylene trimethyl ammonium dimethyl phosphate.
Claim 54
Dependent Claim
17 words
The composition of claim 29 wherein the ethylenically unsaturated compounds consist essentially of derivatives of acrylic acid.
Claim 55
Dependent Claim
112 words
A photopolymerizable composition comprising at least one photopolymerizable ethylenically unsaturated compound containing a photoinitiating compound in an amount sufficient to initiate photopolymerization and a stabilizing amount of an ammonium salt of a phosphorus acid having the formula ##STR53## wherein R is hydrocarbyl or thiophenealkylene; R', r" and R"' are a. independently selected hydrocarbyl; or b. together are part of a heterocyclic amino radical in which the quaternary nitrogen in the formula is part of the ring; X is oxygen or sulfur; Y and Y' are independently selected alkoxy, thioalkoxy, alkenyloxy, thioalkenyloxy, alkyl, alkylcarboxyalkyl, phenylalkyl, phenyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy, or alkylthiophenoxy; Z is oxygen or sulfur; and m is 1 or 2.
Claim 56
Dependent Claim
112 words
A photopolymerizable composition comprising at least one photopolymerizable ethylenically unsaturated compound containing a photoinitiating compound in an amount sufficient to initiate photopolymerization and a stabilizing amount of an ammonium salt of a phosphorus acid having the formula ##STR53## wherein R is hydrocarbyl or thiophenealkylene; R', r" and R"' are a. independently selected hydrocarbyl; or b. together are part of a heterocyclic amino radical in which the quaternary nitrogen in the formula is part of the ring; X is oxygen or sulfur; Y and Y' are independently selected alkoxy, thioalkoxy, alkenyloxy, thioalkenyloxy, alkyl, alkylcarboxyalkyl, phenylalkyl, phenyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy, or alkylthiophenoxy; Z is oxygen or sulfur; and m is 1 or 2.
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) | 1981-03-06 | 1981-09-05 | 1982-03-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-06 | 1985-09-05 | 1986-03-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-06 | 1989-09-05 | 1990-03-07 | $7700.00 | Window Closed / Lapsed |