US4785064A
Expired / Lapsed
US
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Ultra-violet light curable compositions for abrasion resistant articles
Assignee: 3M Co
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Filing: 1986-11-03
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Granted: 1988-11-15
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Expires: 2006-11-03
Abstract
Abstract Inherently highly abrasion-resistant cast articles are prepared by polymerizing a composition comprising (I) as a first component from 0 to 100 parts of urethane polyacrylic ester and (II) as a second component, correspondingly from 100 to 0 parts of a composition containing (A) 30 to 60% by weight of a polyacrylic ester having 4 to 10 acryloyloxy groups, (B) 20 to 70% by weight of a polymerization shrinkage modifier, and (C) 0 to 30% of a diluent monomer. A source of free-radicals may be added to the composition.
Inventors
- 👤 Ramon F. Hegel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 06:36
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; C; C08; C08F; C08F222/00; C08F222/10; C08F222/1006; C08F299/00; C08F299/02; C08F299/022; C08F299/06; G02B1/041
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
175 words
An article comprising a polymerized resin derived from (I) at least 45 parts by weight of a urethane polyacrylic ester first component having the formula ##STR10## wherein: R 1 has the valence "a" and is the residue remaining after the removal of --NCO groups from an organic polyisocyanate; R 2 has the valence b+1 and is a polyvalent aliphatic group having 4 to 10 carbon atoms; R 3 is --H or --CH 3 ; a is a number having a value of at least 2; and b is an integer of 3 to 5, (II) at most 55 parts by weight of a second component containing (A) from 30 to 60% by weight of a polyacrylic ester, (B) from 20 to 70% by weight of a polymerization shrinkage modifier, and (C) from 0 to 30% by weight of a diluent monomer, and (III) from 0 to 5% by weight of I plus II of a source of free radicals, said article having an inherent abrasion resistance to 000 steel wool of at least 140 kPa.
Claim 2
Dependent Claim
175 words
An article comprising a polymerized resin derived from (I) at least 45 parts by weight of a urethane polyacrylic ester first component having the formula ##STR10## wherein: R 1 has the valence "a" and is the residue remaining after the removal of --NCO groups from an organic polyisocyanate; R 2 has the valence b+1 and is a polyvalent aliphatic group having 4 to 10 carbon atoms; R 3 is --H or --CH 3 ; a is a number having a value of at least 2; and b is an integer of 3 to 5, (II) at most 55 parts by weight of a second component containing (A) from 30 to 60% by weight of a polyacrylic ester, (B) from 20 to 70% by weight of a polymerization shrinkage modifier, and (C) from 0 to 30% by weight of a diluent monomer, and (III) from 0 to 5% by weight of I plus II of a source of free radicals, said article having an inherent abrasion resistance to 000 steel wool of at least 140 kPa.
Claim 3
Dependent Claim
21 words
An article according to claim 1 wherein said urethane polyacrylic ester is the reaction product of a polyacryloyloxyalkanol and a polyisocyanate.
Claim 4
Dependent Claim
34 words
An article according to claim 2 wherein said polyacryloyloxyalkanol comprises a polyol having from 4 to 10 carbon atoms and from 4 to 6 hydroxy groups, and said polyisocyanate comprises a di- or triisocyanate.
Claim 5
Dependent Claim
43 words
An article according to claim 3 wherein said polyacryloyloxyalkanol is selected from pentaerythritol triacrylate, dipentaerythritol pentaacrylate, 2,2,3,3-tetra(acryloyloxymethyl)propanol, arabitol tetraacrylate, and sorbitol pentaacrylate and the corresponding methacrylates and said polyisocyanate is selected from 2,4-tolylene diisocyanate, 3,5,5-trimethyl-1-isocyanato-3-isocyanatomethylcyclohexane, hexamethylene diisocyanate, 1,3,5-tris(6-isocyanatohexyl-1,3,5-triazine-2,4,6(1H,3H,5H)trione, 1,3-di(isocyanatoethyl)hydantoin, 2,2,4-trimethylhexamethylene diisocyanate and 1,3,5-benzenetriisocyanate.
Claim 6
Dependent Claim
19 words
An article according to claim 4 wherein said polyacryloyloxalkanol is pentaerythritol triacrylate or methacrylate and said polyisocyanate is 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)trione.
Claim 7
Dependent Claim
34 words
An article according to claim 1 wherein said polymerized resin is derived from 100 parts by weight of said first component and from 0 to 5% by weight of said source of free radicals.
Claim 8
Dependent Claim
35 words
An article according to claim 1 wherein said second component comprises from 45 to 60 percent by weight of said polyacrylic ester and from 20 to 55 percent by weight of said polymerization shrinkage modifier.
Claim 9
Dependent Claim
57 words
An article according to claim 7 wherein said polyacrylic ester of said second component is derived from an alkane, a cycloalkane, or an azacycloalkane polyol, the polyol having up to 24 carbon atoms and the ester having from 4 to 10 acryloxy groups and nitrogen, when present, being covalently bonded to the carbon of a carbonyl group.
Claim 10
Dependent Claim
48 words
An article according to claim 8 wherein said polymerization shrinkage modifier of said second component is a polymerizable carbamic compound having at least two of ##STR11## groups and at least two acrylic groups per 168 to 2000 of molecular weight and a molecular weight of 168 to 5000.
Claim 11
Dependent Claim
98 words
An article according to claim 9 wherein said polymerization shrinkage modifier has the formula ##STR12## in which: R 3 is --H or --CH 3 ; R 4 is a divalent aliphatic group selected from --R 6 -- and ##STR13## in which --R 6 -- is an alkylene group having 1 to 6 carbon atoms or a 5- or 6-membered cycloalkylene group having 5 to 10 carbon atoms; R 5 is a polyvalent linear structure obtained by removal of the hydroxyl groups from a monomeric or polymeric aliphatic polyol; and c is an integer of from 2 to 15.
Claim 12
Dependent Claim
91 words
An article according to claim 9 wherein said polymerization shrinkage modifier has the formula ##STR14## in which: R 7 is a polyvalent aliphatic group selected from R 6 and ##STR15## in which R 6 is an alkylene group having 1 to 6 carbon atoms or a 5- or 6-membered cycloalkylene group having 5 to 10 carbon atoms and R 11 has a valence of g+1 and is a polyvalent aliphatic group having 4 to 10 carbon atoms and, optionally, one catenary oxygen atom; g is an integer of 1 to 3.
Claim 13
Dependent Claim
57 words
An article according to claim 9 wherein said shrinkage modifier has the formula ##STR16## wherein: R 3 is --H or --CH 3 ; R 8 is a linear, branched, or cyclic alkadiyl or -triyl group having 2 to 10 carbon atoms and, optionally, up to 4 catenary oxygen atoms; and d is the integer 2 or 3.
Claim 14
Dependent Claim
132 words
An article according to claim 9 wherein said polymerization shrinkage modifier has the formula ##STR17## in which: R 3 is --H or --CH 3 ; R 4 is a divalent aliphatic group selected from --R 6 -- and ##STR18## in which --R 6 -- is an alkylene group having 1 to 6 carbon atoms or a 5- 6-membered cycloalkylene group having 5 to 10 carbon atoms; R 9 is alkylene having from 2 to 4 carbon atoms; e is a number having a value of 1 to 3; f is an integer of from 3 to 6; and R 10 is a residue of an alkane, cycloalkane, or azacycloalkane polyol having up to 24 carbon atoms and the nitrogen of the azacycloalkane being covalently bonded to the carbon of a carbonyl group.
Claim 15
Dependent Claim
13 words
An article according to claim 7 wherein said polymerization shrinkage modifier is 1,3,5-tris(2-acryloyloxyethyl)isocyanurate.
Claim 16
Dependent Claim
8 words
An optical article in accordance with claim 1.
Claim 17
Dependent Claim
8 words
An optically clear article according to claim 15.
Claim 18
Dependent Claim
17 words
An optical article according to claim 16 having an index of refraction of from 1.45 to 1.75.
Claim 19
Dependent Claim
16 words
An optical article according to claim 16 having a maximum thickness of at least 2 millimeters.
Claim 20
Dependent Claim
7 words
An ophthalmic lens according to claim 16.
Claim 21
Dependent Claim
24 words
An ophthalmic lens according to claim 19 wherein said urethane polyacrylic ester first component is the reaction product of a polyaryloyloxyalkanol and a polyisocyanate.
Claim 22
Dependent Claim
35 words
An ophthalmic lens according to claim 20 wherein said polyacryloyloxyalkanol comprises a polyol having from 4 to 10 carbon atoms and from 4 to 6 hydroxy groups, and said polyisocyanate comprises a di- or triisocyanate.
Claim 23
Dependent Claim
44 words
An ophthalmic lens according to claim 21 wherein said polyacryloyloxyalkanol is selected from pentaerythritol triacrylate, dipentaerythritol pentaacrylate, 2,2,3,3-tetra(acryloyloxymethyl)propanol, arabitol tetraacrylate, and sorbitol pentaacrylate and the corresponding methacrylates and said polyisocyanate is selected from 2,4-tolylene diisocyanate, 3,5,5-trimethyl-1-isocyanato-3-isocyanatomethylcyclohexane, hexamethylene diisocyanate, 1,3,5-tris(6-isocyanatohexyl-1,3,5-triazine-2,4,6(1H,3H,5H)trione, 1,3-di(isocyanatoethyl)-hydantoin, 2,2,4-trimethylhexamethylene diisocyanate and 1,3,5-benzenetriisocyanate.
Claim 24
Dependent Claim
20 words
An ophthalmic lens according to claim 22 wherein said polyacryloyloxalkanol is pentaerythritol triacrylate or methacrylate and said polyisocyanate is 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)trione.
Claim 25
Dependent Claim
36 words
An ophthalmic lens according to claim 19 wherein said second component comprises from 45 to 60 percent by weight of said polyacrylic ester and from 20 to 55 percent by weight of said polymerization shrinkage modifier.
Claim 26
Dependent Claim
37 words
An ophthalmic lens according to claim 24 wherein said polymerization shrinkage modifier is the reaction product of polyester polyol having a hydroxyl functionality of 5 to 7 and 2-isocyanatoethyl methacrylate and the polyacrylic ester is dipentaerythritol pentaacrylate.
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) | 1991-11-15 | 1992-05-16 | 1992-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-15 | 1996-05-16 | 1996-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-15 | 2000-05-16 | 2000-11-15 | $7700.00 | Window Closed / Lapsed |