US5230982A
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Photoinitiator compositions containing disulfides and photohardenable compositions containing the same
Assignee: Eastman Kodak Co
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Filing: 1991-11-19
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Granted: 1993-07-27
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Expires: 2011-11-19
Abstract
Abstract A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound, an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of the polymerizable or crosslinkable compound, and a disulfide represented by the structure ##STR1## wherein X is selected from the group consisting of S and O except in a specific case in which the disulfide is derived from one or more tetrazolyl groups; n represents 0 or 1; A represents the residue of the ring containing the N, C and X atoms, the ring containing five or six members and, in addition, said ring members may be fused to an aromatic ring; and R 5 is an aromatic radical selected from the group consisting of (i) phenyl, (ii) benzothiazolyl, (iii) benzoxazolyl, (iv) tetrazolyl, (v) pyridinyl, (vi) pyrimidinyl, (vii) thiazolyl, (viii) oxazolyl, (ix) quinazolinyl, and (x) thiadiazolyl, each of which may have a substituent on one or more C or N atoms of the ring.
Inventors
- 👤 Paul D. Davis
- 👤 Jacqueline G. Truini
- 👤 David A. Hutchings
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 11:15
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031; G03F7/002; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/12; Y10S430/121
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
115 words
A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound, a disulfide, and an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound, said disulfide represented by the structure ##STR22## wherein n represents 0 or 1; X represents S or O; R 2 is selected from the group consisting of R 1 --S--, C 1 -C 20 alkyl sulfido, C 1 -C 20 alkyl, C 5 -C 12 cycloalkyl, --SH and H; and R 1 represents an aromatic radicals having 5 or 6 ring members, and in addition may be fused to an aromatic ring.
Claim 2
Dependent Claim
115 words
A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound, a disulfide, and an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound, said disulfide represented by the structure ##STR22## wherein n represents 0 or 1; X represents S or O; R 2 is selected from the group consisting of R 1 --S--, C 1 -C 20 alkyl sulfido, C 1 -C 20 alkyl, C 5 -C 12 cycloalkyl, --SH and H; and R 1 represents an aromatic radicals having 5 or 6 ring members, and in addition may be fused to an aromatic ring.
Claim 3
Dependent Claim
10 words
The composition of claim 1 wherein said composition is microencapsulated.
Claim 4
Dependent Claim
115 words
The photohardenable composition of claim 1 consisting essentially of a free radical addition polymerizable or crosslinkable compound, a disulfide, and an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound, said disulfide represented by the structure: ##STR23## wherein n represents 0 or 1; X represents S or O; R 2 is selected from the group consisting of R 1 --S--, C 1 -C 20 alkyl sulfido, C 1 -C 20 alkyl, --SH and H; and R 1 represents an aromatic radical having 5 or 6 ring members, and in addition may be fused to an aromatic ring.
Claim 5
Dependent Claim
106 words
A photohardenable composition consisting essentially of a free radical addition polymerizable or crosslinkable compound, a disulfide, and an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound, said disulfide being represented by the structure: ##STR24## wherein R 15 represents an aromatic radical and R 4 is selected from the group consisting of C 1 -C 20 alkyl, C 5 -C 12 cycloalkyl, C 7 -C 20 aralkyl, phenyl, naphthyl, mono or dihalogenated phenyl, mono or dihalogenated naphthyl, C 2 -C 20 dialkylaminophenyl, and C 2 -C 20 dialkylaminoaphthyl.
Claim 6
Dependent Claim
106 words
A photohardenable composition consisting essentially of a free radical addition polymerizable or crosslinkable compound, a disulfide, and an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound, said disulfide being represented by the structure: ##STR24## wherein R 15 represents an aromatic radical and R 4 is selected from the group consisting of C 1 -C 20 alkyl, C 5 -C 12 cycloalkyl, C 7 -C 20 aralkyl, phenyl, naphthyl, mono or dihalogenated phenyl, mono or dihalogenated naphthyl, C 2 -C 20 dialkylaminophenyl, and C 2 -C 20 dialkylaminoaphthyl.
Claim 7
Dependent Claim
10 words
The composition of claim 4 wherein said composition is microencapsulated.
Claim 8
Dependent Claim
15 words
The composition of claim 4 wherein said disulfide is 1-phenyl-1H-tetrazol-5-yl disulfide having the structure: ##STR25##
Claim 9
Dependent Claim
155 words
A photohardenable composition consisting essentially of a free radical addition polymerizable or crosslinkable compound, a disulfide, and an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of the polymerizable or crosslinkable compound, said disulfide represented by the structure: ##STR26## wherein X is selected from the group consisting of S and O; n represents 0 or 1; A represents the residue of the ring containing the N, C and X atoms, the ring containing five or six members and, in addition, said ring members may be fused to an aromatic ring; and R 5 is an aromatic radical selected from the group consisting of (i) phenyl, (ii) benzothiazolyl, (iii) benzoxazolyl, (iv) tetrazolyl, (v) pyridinyl, (vi) pyrimidinyl, (vii) thiazolyl, (viii) oxazolyl, (ix) quinazolinyl, and (x) thiadiazolyl, each of which may have a substituent on one or more C or N atoms of the ring.
Claim 10
Dependent Claim
155 words
A photohardenable composition consisting essentially of a free radical addition polymerizable or crosslinkable compound, a disulfide, and an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of the polymerizable or crosslinkable compound, said disulfide represented by the structure: ##STR26## wherein X is selected from the group consisting of S and O; n represents 0 or 1; A represents the residue of the ring containing the N, C and X atoms, the ring containing five or six members and, in addition, said ring members may be fused to an aromatic ring; and R 5 is an aromatic radical selected from the group consisting of (i) phenyl, (ii) benzothiazolyl, (iii) benzoxazolyl, (iv) tetrazolyl, (v) pyridinyl, (vi) pyrimidinyl, (vii) thiazolyl, (viii) oxazolyl, (ix) quinazolinyl, and (x) thiadiazolyl, each of which may have a substituent on one or more C or N atoms of the ring.
Claim 11
Dependent Claim
107 words
The composition of claim 7 wherein said disulfide is represented by the structure ##STR27## wherein R 6 and R 7 independently represent H, C 1 -C 20 alkyl, C 1 -C 20 aralkyl, phenyl or when together cyclized represent a fused aromatic ring which may be substituted; X is selected from the group consisting of S and O; and R 5 is selected from the group consisting of (i) phenyl, (ii) benzothiazolyl, (iii) benzoxazolyl, (iv) tetrazolyl, (v) pyridinyl, (vi) pyrimidinyl, (vii) thiazolyl, (viii) oxazolyl, (ix) quinazolinyl, and (x) thiadiazolyl, each of which may have a substituent on one or more C or N atoms of the ring.
Claim 12
Dependent Claim
66 words
The composition of claim 8 wherein X is S, R 7 is phenyl, R 6 is H, and R 5 is selected from the group consisting of (i) phenyl, (ii) benzothiazolyl, (iii) benzoxazolyl, (iv) tetrazolyl, (v) pyridinyl, (vi) pyrimidinyl, (vii) thiazolyl, (viii) oxazolyl, (ix) quinazolinyl, and (x) thiadiazolyl each of which may have a substituent on one or more C or N atoms of the ring.
Claim 13
Dependent Claim
96 words
The composition of claim 8 wherein said disulfide is represented by the structure ##STR28## R 8 and R 9 are independently selected from the group consisting of H, C 1 -C 20 alkoxy, C 1 -C 20 alkyl, phenyl, naphthyl, and phenoxy; X is O or S; and R 5 is selected from the group consisting of (i) phenyl, (ii) benzothiazolyl, (iii) benzoxazolyl, (iv) tetrazolyl, (v) pyridinyl, (vi) pyrimidinyl, (vii) thiazolyl, (viii) oxazolyl, (ix) quinazolinyl, and (x) thiadiazolyl, each of which may have a substituent on one or more C or N atoms of the ring.
Claim 14
Dependent Claim
72 words
The composition of claim 10 wherein X is S, R 8 is C 1 -C 6 alkoxy or H; R 9 is H; and R 5 is selected from the group consisting of (i) phenyl, (ii) benzothiazolyl, (iii) benzoxazolyl, (iv) tetrazolyl, (v) pyridinyl, (vi) pyrimidinyl, (vii) thiazolyl, (viii) oxazolyl, (ix) quinazolinyl, and (x) thiadiazolyl, each of which may have a substituent on one or more C or N atoms of the ring.
Claim 15
Dependent Claim
31 words
The composition of claim 11 wherein R 5 is phenyl, mono- or dihalogenated phenyl, phenyl substituted with C 1 -C 20 alkoxy, or phenyl substituted with C 1 -C 20 alkyl.
Claim 16
Dependent Claim
43 words
The composition of claim 12 wherein said disulfide is selected from the group consisting of 6-ethoxybenzothiazol-2-yl phenyl-disulfide (EBTP-D) having the structure: ##STR29## 6-ethoxybenzothiazol-2-yl 4-methylphenyl-disulfide (EBMP-D) having the structure: ##STR30## 6-ethoxybenzothiazol-2-yl 4-dodecyloxyphenyl-disulfide (EBC12-D) having the structure: ##STR31## 6-ethoxybenzothiazol-2-yl 4-chlorophenyl-disulfide (EBCP-D) having the structure: ##STR32##
Claim 17
Dependent Claim
13 words
The composition of claim 11 wherein said disulfide is 6-ethoxymercaptobenzothiazol-2-yl disulfide (EMBT-D) ##STR33##
Claim 18
Dependent Claim
28 words
The composition of claim 11 wherein said disulfide is selected from the group consisting of 2-dimethylaminophenyl 6-ethoxybenzothiazol-2-yl disulfide having structure: ##STR34## 4-dimethylaminophenyl 6-ethoxybenzothiazol-2-yl disulfide having the structure: ##STR35##
Claim 19
Dependent Claim
66 words
The composition of claim 10 wherein X is O; R 8 and R 9 are each H; and R 5 is selected from the group consisting of (i) phenyl, (ii) benzothiazolyl, (iii) benzoxazolyl, (iv) tetrazolyl, (v) pyridinyl, (vi) pyrimidinyl, (vii) thiazolyl, (viii) oxazolyl, (ix) quinazolinyl, and (x) thiadiazolyl, each of which may have a substituent on one or more C or N atoms of the ring.
Claim 20
Dependent Claim
16 words
The composition of claim 10 wherein said disulfide is mercaptobenzothiazol-2-yl disulfide (MBO-D) having the structure: ##STR36##
Claim 21
Dependent Claim
10 words
The composition of claim 7 wherein said composition is microencapsulated.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-07-26 | 1997-01-25 | 1997-07-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-07-26 | 2001-01-25 | 2001-07-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-07-26 | 2005-01-25 | 2005-07-27 | $7700.00 | Window Closed / Lapsed |