EP0378144A2
Expired / Lapsed
EP
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Photocurable compositions
Assignee: Huntsman Advanced Materials Switzerland GmbH
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Filing: 1990-01-08
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Granted: —
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Expires: 2010-01-08
Abstract
Abstract The invention relates to a liquid resin composition which can be polymerized by radiation and which contains (i) a difunctional monomeric or polymeric acrylate or methacrylate, (ii) a tri- or polyfunctional acrylate or methacrylate, (iii) at least one unsaturated monofunctional monomeric compound of the formula VI wherein R⁵ denotes hydrogen or methyl and R⁶ is a group of the formula VII - -O-R⁷ (VII), R⁷ being tetrahydrofurfuryl, cyclohexyl, 2-phenoxyethyl, benzyl, isobornyl, glycidyl, dicyclopentenyl, morpholinoethyl, dimethylaminoethyl, diethylaminoethyl or a C₁-C₂₀ linear or branched aliphatic residue, or - if R⁵ is hydrogen R⁶ denotes additionally pyrrolidinon-2-yl, imidazonyl, carbazolyl, anthracenyl, phenyl, C₅-C₈cycloalkyl, naphthenyl, 2-norbornyl, pyridyl, N-caprolactamyl or toluyl and (iv) a photo-polymerization initiator for (i), (ii) and/or (iii). Such compositions are suitable in the stereolithographic process, as coatings or as adhesives.
Inventors
- 👤 Max Dr. Hunziker
- 👤 Adrian Dr. Schulthess
- 👤 Manfred Dr. Hofmann
- 👤 Bernd Dr. Klingert
- 👤 Richard Noel Leyden
- 👤 Kris Alan Schmidt
- 👤 Paul Dr. Bernhard
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-26 22:47
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; C; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/20; C08F2/00; C08F2/46; C08F220/26; C08F220/34; C08F220/36; C08F222/00; C08F222/10; C08F222/1006; C08F222/102; C08F222/1025; C08F299/00; C09; C09D; C09D4/00; G03C; G03C9/00; G03C9/08; G03F7/0037
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
170 words
Liquid resin compositions which are photosensitive comprising (i) at least one difunctional monomeric or oligomeric acrylate or methacrylate having a viscosity of more than 500 mPas at 25°C, (ii) at least one tri-, tetra- or pentaacrylate or -methacrylate selected from the group consisting of the compounds of the formulae I, II and III wherein R¹ denotes hydrogen, methyl, hydroxy or a group and R² is a group wherein n is an integer 0, 1, 2 or 3, R³ and R⁴ are each independently of the other hydrogen or methyl, (iii) at least one unsaturated monofunctional monomeric compound of the formula VI wherein R⁵ denotes hydrogen or methyl and R⁶ is a group of the formula VII - -O-R⁷ (VII), R⁷ being tetrahydrofurfuryl, cyclohexyl, 2-phenoxyethyl, benzyl, isobornyl, glycidyl, dicyclopentenyl, morpholinoethyl, dimethylaminoethyl, diethylaminoethyl or a C₁-C₂₀ linear or branched aliphatic residue, or - if R⁵ is hydrogen R⁶ denotes additionally pyrrolidinon-2-yl, imidazolyl, carbazolyl, anthracenyl, phenyl, C₅-C₈cycloalkyl, naphthenyl, 2-norbornyl, pyridyl, N-caprolactamyl or toluyl and (iv) a photo-polymerization initiator for (i), (ii) and/or (iii).
Claim 2
Dependent Claim
170 words
Liquid resin compositions which are photosensitive comprising (i) at least one difunctional monomeric or oligomeric acrylate or methacrylate having a viscosity of more than 500 mPas at 25°C, (ii) at least one tri-, tetra- or pentaacrylate or -methacrylate selected from the group consisting of the compounds of the formulae I, II and III wherein R¹ denotes hydrogen, methyl, hydroxy or a group and R² is a group wherein n is an integer 0, 1, 2 or 3, R³ and R⁴ are each independently of the other hydrogen or methyl, (iii) at least one unsaturated monofunctional monomeric compound of the formula VI wherein R⁵ denotes hydrogen or methyl and R⁶ is a group of the formula VII - -O-R⁷ (VII), R⁷ being tetrahydrofurfuryl, cyclohexyl, 2-phenoxyethyl, benzyl, isobornyl, glycidyl, dicyclopentenyl, morpholinoethyl, dimethylaminoethyl, diethylaminoethyl or a C₁-C₂₀ linear or branched aliphatic residue, or - if R⁵ is hydrogen R⁶ denotes additionally pyrrolidinon-2-yl, imidazolyl, carbazolyl, anthracenyl, phenyl, C₅-C₈cycloalkyl, naphthenyl, 2-norbornyl, pyridyl, N-caprolactamyl or toluyl and (iv) a photo-polymerization initiator for (i), (ii) and/or (iii).
Claim 3
Dependent Claim
101 words
Compositions according to claim 1 containing as component (i) at least one acrylic or methacrylic diester of the general formula VIII wherein p is 0 or 1 and t is 0 or 1 and if p is 0, t can also be 2 or 3, X denotes -O-, -S-, -SO₂- or -C(R¹⁰)(R¹¹)-, R¹⁰ and R¹¹ each being independently of the other hydrogen, -CF₃ or methyl and R⁷ denotes hydrogen if p is 1 and hydrogen or methyl if p is 0, and R⁸ denotes hydroxy if p is 1 and hydrogen if p is 0, and R⁹ is hydrogen or methyl.
Claim 4
Dependent Claim
14 words
Compositions according to claim 2, characterized in that in formula VIII p denotes 1.
Claim 5
Dependent Claim
14 words
Compositions according to claim 3, characterized in that in formula VIII X is -C(CH₃)₂-.
Claim 6
Dependent Claim
35 words
Compositions according to claim 2 containing as component (i) a mixture of compounds of the formula VIII comprising at least one compound wherein p is 1 and at least one compound wherein p is 0.
Claim 7
Dependent Claim
25 words
Compositions according to claim 1 containing the component (i) in a total amount of about 10 to about 80 weight percent of the total composition.
Claim 8
Dependent Claim
27 words
Compositions according to claim 3 containing the compound of formula VIII in a total amount of 30 to about 60 weight percent based on the total composition.
Claim 9
Dependent Claim
43 words
Composition according to claim 1 containing as component (ii) at least one triacrylate or -methacrylate of the formula I wherein R¹ is methyl or a group of the formula IV and R² denotes a group of the formula V wherein n is 0.
Claim 10
Dependent Claim
12 words
Compositions according to claim 1 containing as component (ii) trimethylolpropanetrimethacrylate or dipentaerythritolpentaacrylate.
Claim 11
Dependent Claim
26 words
Composition according to claim 1 containing the component (ii) in a total amount of about 5 to about 25 weight percent based on the total composition.
Claim 12
Dependent Claim
31 words
Composition according to claim 1, containing as component (iii) a compound of the formula VI wherein R⁵ is hydrogen and R⁶ is a group of the formula VII, pyrrolidon-2-yl or N-caprolactamyl.
Claim 13
Dependent Claim
13 words
Compositions according to claim 11, containing as component (iii) 1-vinylpyrrolidone, isobornylacrylate and/or phenoxyethylacrylate.
Claim 14
Dependent Claim
26 words
Compositions according to claim 1, containing the component (iii) in a total amount of about 1 to about 25 weight percent based on the total composition.
Claim 15
Dependent Claim
15 words
Compositions according to claim 1, containing as component (iv) an acetophenone, an 1-hydroxyphenylketone and/or benzilketal.
Claim 16
Dependent Claim
26 words
Compositions according to claim 1, containing as component (iv) in a total amount of about 0.1 to about 10 weight percent based on the total composition.
Claim 17
Dependent Claim
18 words
Compositions according to claim 1 with a viscosity in the range of 500 to 5000 mPas at 30°C.
Claim 18
Dependent Claim
17 words
A process for polymerizing the compositions according to claim 1 comprising subjecting said compositions to actinic radiation.
Claim 19
Dependent Claim
86 words
A method of generating three-dimensional objects from a fluid medium capable of altering its physical state when subjected to prescribed radiation, said method comprising: - containing as fluid medium a body of a composition according to claim 1; - irradiating a designated surface of said composition with a prescribed pattern to provide a thin cross-sectional lamina at said designated surface; and - repeatedly forming a series of such laminae in succession to build the desired three-dimensional object from successive adjacent laminae which together define said object.
Claim 20
Dependent Claim
14 words
A method according to claim 18 wherein the radiation source is a UV-laser beam.
Claim 21
Dependent Claim
13 words
A method according to claim 19 wherein the laser beam is computer controlled.
References Cited (Backward Citations)
No citation records indexed.
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