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US4458007A Expired / Lapsed US ⏱️ 0.0 years remaining

Radiation polymerizable mixture containing reaction products of glycerol acrylates and polyisocyanates

Assignee: Hoechst AG
•
Filing: 1981-12-15
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Granted: 1984-07-03
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Expires: 2001-12-15
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Abstract

Abstract A radiation-polymerizable mixture comprising a polymeric binder, a radiation-activatable polymerization initiator and a polymerizable acrylate or methacrylate ester having at least two urethane groups in the molecule, said ester being a reaction product of glycerol dimethacrylate or glycerol diacrylate and a polyisocyanate obtained by reacting a polyhydroxy compound having from two to six hydroxyl groups with a diisocyanate or a reaction product of glycerol dimethacrylate or glycerol diacrylate and a diisocyanate. The new polymerizable urethanes provide the mixture with a high light-sensitivity, good reciprocity and a low tendency to crystallize.

Inventors

  • 👤 Ulrich Geissler
  • 👤 Heide Sprengel
  • 👤 Walter Herwig
  • 👤 Manfred Hasenjaeger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 10:33
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/675; G03F7/027; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/106; Y10S430/107

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 268 words
A radiation-polymerizable mixture consisting essentially of: (a) from about 20 to 80 weight percent of a polymeric binder soluble in aqueous solutions; (b) from about 0.1 to 20 weight percent of a radiation-activatable polymerization initiator; and (c) from about 20 to 80 weight percent of an acrylate or methacrylate ester of a polyhydric hydroxy compound having at least two urethane groups in the molecule; said ester being a reaction product of glycerol dimethacrylate or glycerol diacrylate and a polyisocyanate; said polyisocyanate being (i) a diisocyanate; (ii) a reaction product of 1 mole of a trihydroxy compound and 3 moles of a diisocyanate, said trihydroxy compound corresponding to one of the following formulas: HO--[C.sub.p H.sub.2p-v (OH).sub.v S--].sub.m-1 C.sub.p H.sub.2p-v (OH).sub.v-1, HO--[C.sub.p H.sub.2p-v (CH).sub.v --O--].sub.m H, and HO--C.sub.s H.sub.2s-v (OH).sub.v --Z(--CO--C.sub.q H.sub.2q --O).sub.m --H; or (iii) a reaction product of a dihydroxy compound with a diisocyanate, said dihydroxy compound corresponding to one of the following formulas: HO--[C.sub.p H.sub.2p --S--].sub.m-1 C.sub.p H.sub.2p (OH), HO--[C.sub.p H.sub.2p --O--].sub.m H, HO--C.sub.s H.sub.2s --Z(--CO--C.sub.q H.sub.2q --O).sub.m --H, and ##STR2## in which formulas for both of said trihydroxy compound and said dihydroxy compound, respectively: R" represents O, S, CR 2 or SO 2 , R represents a hydrogen atom or a methyl group, Z represents O or NR, n represents an integer from 0 to 20, m represents an integer from 1 to 40, p represents an integer from 2 to 20, q represents an integer from 2 to 10, s represents an integer from 2 to 10, and v is 0 or 1, p, q, and s each being at least 2 greater than v.
Claim 2
Dependent Claim 268 words
A radiation-polymerizable mixture consisting essentially of: (a) from about 20 to 80 weight percent of a polymeric binder soluble in aqueous solutions; (b) from about 0.1 to 20 weight percent of a radiation-activatable polymerization initiator; and (c) from about 20 to 80 weight percent of an acrylate or methacrylate ester of a polyhydric hydroxy compound having at least two urethane groups in the molecule; said ester being a reaction product of glycerol dimethacrylate or glycerol diacrylate and a polyisocyanate; said polyisocyanate being (i) a diisocyanate; (ii) a reaction product of 1 mole of a trihydroxy compound and 3 moles of a diisocyanate, said trihydroxy compound corresponding to one of the following formulas: HO--[C.sub.p H.sub.2p-v (OH).sub.v S--].sub.m-1 C.sub.p H.sub.2p-v (OH).sub.v-1, HO--[C.sub.p H.sub.2p-v (CH).sub.v --O--].sub.m H, and HO--C.sub.s H.sub.2s-v (OH).sub.v --Z(--CO--C.sub.q H.sub.2q --O).sub.m --H; or (iii) a reaction product of a dihydroxy compound with a diisocyanate, said dihydroxy compound corresponding to one of the following formulas: HO--[C.sub.p H.sub.2p --S--].sub.m-1 C.sub.p H.sub.2p (OH), HO--[C.sub.p H.sub.2p --O--].sub.m H, HO--C.sub.s H.sub.2s --Z(--CO--C.sub.q H.sub.2q --O).sub.m --H, and ##STR2## in which formulas for both of said trihydroxy compound and said dihydroxy compound, respectively: R" represents O, S, CR 2 or SO 2 , R represents a hydrogen atom or a methyl group, Z represents O or NR, n represents an integer from 0 to 20, m represents an integer from 1 to 40, p represents an integer from 2 to 20, q represents an integer from 2 to 10, s represents an integer from 2 to 10, and v is 0 or 1, p, q, and s each being at least 2 greater than v.
Claim 3
Dependent Claim 17 words
A radiation-polymerizable mixture according to claim 1 wherein said ester contains from 2 to 40 urethane groups.
Claim 4
Dependent Claim 15 words
A radiation-polymerizable mixture according to claim 1 wherein said ester is a methacrylic acid ester.
Claim 5
Dependent Claim 31 words
A radiation-polymerizable mixture according to claim 1 wherein said diisocyanate is a compound corresponding to the formula OCN--X--NCO, wherein X represents a hydrocarbon radical having from 2 to 20 carbon atoms.
Claim 6
Dependent Claim 22 words
A mixture according to claim 1 wherein said ester is a reaction product of glycerol dimethacrylate or glycerol diacrylate and a diisocyanate.
Claim 7
Dependent Claim 53 words
A mixture according to claim 5 or claim 1 wherein said diisocyanate is selected from the group consisting of tolylene diisocyanates, xylylene diiosocyanates, naphthylene diisocyanates, hexamethylene diisocyanates, cyclohexylene diisocyanate, diphenylmenthane diisocyanate, isophorone diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate and the reaction product of two moles of tolylene diisocyanate or diphenylmethane diisocyanate and one mole of polytetrahydrofuran.
Claim 8
Dependent Claim 23 words
A mixture according to claim 1 wherein polymerizable compounds comprise from 30 to 70 weight percent of the non-volatile constituents of said mixture.
Claim 9
Dependent Claim 49 words
A mixture according to claim 1 wherein said radiation-activatable polymerization initiator comprises from about 0.1 to about 20 weight percent of the non-volatile constituents of said mixture and is selected from the group consisting of benzoin, benzoin ether, polynuclear quinones, acridine derivatives, phenazine derivatives, quinoxaline derivatives and quinazoline derivatives.
Claim 10
Dependent Claim 56 words
A mixture according to claim 1 wherein said binder is selected from the group consisting of maleate resins, polymers and copolymers of β-methacryloyloxy-ethyl-N-(p-tolyl-sulfonyl)-carbamate, styrene/maleic anhydride copolymers, copolymers of methyl vinyl ether and maleic anhydride or maleic acid esters or half esters, methyl methacrylate/methacrylic acid copolymers and copolymers of methacrylic acid, alkyl methacrylates and styrene, or acrylonitrile.

References Cited (Backward Citations)

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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) 1987-07-03 1988-01-02 1988-07-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-07-03 1992-01-02 1992-07-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-07-03 1996-01-02 1996-07-03 $7700.00 Window Closed / Lapsed

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