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CA1246785A
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CA
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Blends of cyclic vinyl ether containing compounds and a poly(active hydrogen) organic compound
Assignee: Union Carbide Corp
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Filing: 1984-03-28
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Granted: 1988-12-13
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Expires: 2004-03-28
Abstract
Abstract BLENDS OF CYCLIC VINYL ETHER CONTAINING COMPOUNDS AND A POLY (ACTIVE HYDROGEN) ORGANIC COMPOUND ABSTRACT OF THE INVENTION Described herein are compositions suitable for photocopolymerization comprising a cyclic vinyl ether containing compound and a poly(active hydrogen) organic compound. Photocurable coatings can be prepared from such composition and such coatings have improved flexibility and impact resistant properties. S P E C I F I C A T I O N
Inventors
- 👤 Joseph V. Koleske
Bibliographic Details
Application Number
—
Jurisdiction
CA
Data Source
google_patents
Last Synchronized
2026-11-08 23:20
CPC Classifications
—
Claims Analysis
Total Claims: 85
Claim 1
Independent Claim
18 words
A composition suitable for photocopolymerization comprising a cyclic vinyl ether containing compound and a poly(active hydrogen) organic compound.
Claim 2
Dependent Claim
18 words
A composition suitable for photocopolymerization comprising a cyclic vinyl ether containing compound and a poly(active hydrogen) organic compound.
Claim 3
Dependent Claim
267 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is selected from the following: The Z's each represents hydrogen or an alkyl group having from 1 to 10 carbon atoms; X and X' are members of the class consisting of a bivalent saturated hydrocarbon group, R, having the structure, -CnH2n-, wherein n is an integer having a value of from 1 to 10; an oxy radical, -O-; and a carbonyl group, -C(O)-; and, in addition X' may be a carbonyloxy group, -O(O)C-, the carbon atom of which is bonded to the 2-position of the dihydropyranyl ring; X and X' may be the same or different provided that taken together they contain either zero or 2 oxygen atoms; a has a value of from zero to 1, a being zero only when X' is the aforesaid carbonyloxy group; Q is a member of the class consisting of the aforesaid R group; a dioxylakylene group, -ORO-, wherein R is as defined above; a dicarboxylate group, -OC-(O)-R'-C(O)),- wherein R' is the nucleus of a dicarboxylic acid; and a polycarbamate group such as the dicarbamate group, -OC(O)NH-R"-NH-C(O)-, wherin R", as illustrated, is the nucleus of a diisocyanate; and X, X' and Q taken together is such that the linking chain, -X-Q-X'-, contains an even number of oxygen atoms from two to four, provided that when X and X' are both oxy radicals, the linking chain contains no other oxygen atoms (that is, Q or R), and when X and X' are both carbonyl groups, the linking chain contains four oxygen atoms (that is, Q is -ORO-).
Claim 4
Dependent Claim
52 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is 3,4-dihydro-2H-pyran-2-methyl(3,4-dihydro-2H-pyran-2-carboxylates) having the formula: wherein Z and Z' are as above-defined. Preferably a total of from 5 to 7 of the respective Z and Z' groups are hydrogen and correspondingly, from 3 to zero are alkyl groups.
Claim 5
Dependent Claim
39 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is alkanedioxy-bis(3',4'-dihydro-2'H-pyran-2'-carbonyl) compounds having the structure: wherein Z and Z' are as defined in claim 2, and n is an integer from 1 to 10
Claim 6
Dependent Claim
36 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is bis-(3',4'-dihyro-2'H-pyran-2'-oxy)alkanes having the formula: wherein Z, Z' are as defined in claim 2 and n is as defined in claim 4.
Claim 7
Dependent Claim
37 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is bis-(3',4'-dihydro-2'H-pyran-2'alkoxy) alkanes having the formula: wherein Z, Z' are as defined in claim 2 and n is as defined in claim 4.
Claim 8
Dependent Claim
60 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is bis-(3',4'-dihydro-2'H-pyran-2'alkyl) carboxylates having the general formula: wherein Z, Z' are as defined in claim 2, n is as defined in claim 4 and R' is the nucleus of a dicarboxylic acid and may be a bivalent aliphatic, cycloaliphatic or aromatic nucleus including corresponding halogen-substituted nuclei.
Claim 9
Dependent Claim
57 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound has the general formula: wherein Z, Z' are as defined in claim 2, n is as defined in claim 4, R" is an aliphatic, cyloaliphatic or aromatic radical which may be unsubstituted hydrocarbyl groups or hydrocarbyl groups substituted with haolgen or alkoxy groups.
Claim 10
Dependent Claim
162 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is selected from one or more of the following: wherin R1 is hydrogen or methyl, R1 ''' is alkyl of 1 to 10 carbon atoms, and X is selected from wherein n has a value of from 1 to 50 and wherein R1' is the residue of a carboxylic acid and can be (1) hydrogen, (2) alkyl which is substituted with any substituent which does not unduly interfere with the polymerization, or unsubstituted, linear or branched, containing up to 20 carbon atoms, and (3) aryl which is substituted with any substituent which does not unduly interfere with the polymerization or, which is unsubstituted, having 6 to 10 ring carbon atoms; R3 is hydrogen, alkyl, alkoxy, aryl, cycloalkyl, alkaryl or an aralkyl group having up to 12 carbon atoms and at least (2x-3) of the R3 groups are hydrogen atoms, and x has a value of 2 to 12.
Claim 11
Dependent Claim
35 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is an alkylene oxide adduct of 3,4-dihydropyran-2-methanol of the general formula: wherein R1 and n are as defined in claim 9.
Claim 12
Dependent Claim
30 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is of the formula: wherein R1, n, R3 and x are as defined in claim 9.
Claim 13
Dependent Claim
28 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is of the formula: wherein R1 and R1' are as defined in claim 9.
Claim 14
Dependent Claim
37 words
A composition as defined in claim 1 wherein thc cyclic vinyl ether containing compound is of the general formula: wherein R3 is as defined in claim 9 and R1 and n are as defined in claim 10.
Claim 15
Dependent Claim
30 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is of the formula: wherein R1, R3, n, and x are as defined in claim 9.
Claim 16
Dependent Claim
34 words
A composition as defined in claim 1 wherein tho cyclic vinyl ether containing compound is the reaction product of thc following: wherein R1, is as defined in claim 9, and pentaerythritol or an aldehyde.
Claim 17
Dependent Claim
18 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is of the formula:
Claim 18
Dependent Claim
18 words
A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is of the formula:
Claim 19
Dependent Claim
39 words
A composition as defined in claim 1 wherein the poly (active hydrogen) organic compound is selected from the group consisting of a polyether polyol, a polycaprolactone polyol, a polyester polyol, an acrylic polyol, a vinyl polyol, and a polymer/polyol
Claim 20
Dependent Claim
41 words
A composition as defined in claim 18 wherein the polyether polyol is selected from the group consisting of a propylene oxide polyol, an ethylene oxide polyol, a propylene oxide polyol capped with ethylene oxide, a tetramethylene oxide polyol and a polymer/polyol.
Claim 21
Dependent Claim
18 words
A composition as defined as claim 1 wherein the poly (active hydrogen) organic compound is a polymer polyol.
Claim 22
Dependent Claim
18 words
A composition as defined in claim 1 wherein the poly (active hydrogen) organic compound is a polycaprolactone polyol.
Claim 23
Dependent Claim
18 words
A composition as defined in claim 1 wherein the poly (active hydrogen) organic compound is a polyester polyol.
Claim 24
Dependent Claim
18 words
A composition as defined in claim 1 wherein the poly (active hydrogen) organic compound is an acrylic polyol.
Claim 25
Dependent Claim
18 words
A composition as defined in claim 1 wherein the poly (active hydrogen) organic compound is a vinyl polyol.
Claim 26
Dependent Claim
25 words
A composition as defined in claim 1 wherein the poly (active hydrogen) organic compound is a mixture of a polyether polyol and a polycaprolactone polyol.
Claim 27
Dependent Claim
26 words
A composition as defined in claim 1 wherein the poly (active hydrogen) organic compound is a mixture of at least two poly (active hydrogen) organic compounds.
Claim 28
Dependent Claim
17 words
A composition as defined in claim 1 which contains an epoxide containing at least one epoxy group.
Claim 29
Dependent Claim
14 words
A composition as defined in claim 27 wherein the epoxide is a cycloaliphatic epoxide.
Claim 30
Dependent Claim
55 words
A composition as in claim 28 wherein the cycloaliphatic epoxide has the formula: wherein R7 through R24, which can be the same or different, are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive; R is a valence bond or a divalent hydrocarbon radical generally containing one to ten carbon atoms inclusive.
Claim 31
Dependent Claim
37 words
A composition as in claim 28 wherein the cycloaliphatic epoxide has the formula: wherein R1 through R18, which can be the same or different are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive.
Claim 32
Dependent Claim
29 words
A composition as in claim 28 wherein the cycloaliphatic epoxide has the formula: wherein the R's are the same or different and are monovalent substituents or monovalent hydrocarbon radicals.
Claim 33
Dependent Claim
13 words
A composition as in claim 28 wherein the cycloaliphatic epoxide is 3,4-epoxycyclohexyl-methyl-3,4-epoxycyclohexane carboxylate.
Claim 34
Dependent Claim
12 words
A composition as in claim 28 wherein the cycloaliphatic epoxide is bis(3,4-epoxycyclo-hexylmethyl)-adipate.
Claim 35
Dependent Claim
12 words
A composition as in claim 28 wherein the cycloaliphatic epoxide is 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)-cyclohexane-meta-dioxane.
Claim 36
Dependent Claim
14 words
A composition as defined in claim 28 wherin the cycloaliphatic epoxide is vinylcylohexene diepoxide.
Claim 37
Dependent Claim
17 words
A composition as in claim 28 wherein the cycloaliphatic epoxide is a mixture of bis(3,4-epoxycyclohexylmethyl)adipate and 2-(3,4-epoxycyclo-hexyl-5,5-spiro-3,4-epoxy)-cyclohexane-meta-dioxane.
Claim 38
Dependent Claim
19 words
A composition as in claim 28 wherein the cycloaliphatic epoxide is a mixture of 3,4-epoxy-cyclohexylmethyl-3,4-epoxycyclohexane carboxylate and bis(3,4-epoxycyclohexylmethyl) adipate.
Claim 39
Dependent Claim
10 words
A composition as in claim 37 which includes 2-(3,4-epoxycyclohexyl)-5,5-spiro-3,4-epoxy) cyclohexane-meta-dioxane.
Claim 40
Dependent Claim
42 words
A composition as defined in claim 28 which contains minor amounts of one or more glycidyl type epoxides, aliphatic epoxides, epoxy cresol novolac resins, epoxy phenol novolac resins, poly-nuclear phenol-glycidyl ether-derived resins aromatic and heterocyclic glycidyl amine resins or hydantoin epoxy resins.
Claim 41
Dependent Claim
12 words
A composition as in claim 1 which contains a glycidyl type epoxide.
Claim 42
Dependent Claim
11 words
a composition as in claim 40 which contains a cycloaliphatic epoxide.
Claim 43
Dependent Claim
12 words
A composition as in claim 1 which contains a linear vinyl ether.
Claim 44
Dependent Claim
17 words
A composition as defined in claim 42 wherein the linear vinyl ether is an alkyl vinyl ether.
Claim 45
Dependent Claim
16 words
A composition as defined in claim 42 wherein the linear ether is an aryl vinyl ether.
Claim 46
Dependent Claim
16 words
A composition as defined in claim 42 wherein the linear vinyl ether is a divinyl ether.
Claim 47
Dependent Claim
11 words
A composition as defined in claim 1 which contains a photoinitiator.
Claim 48
Dependent Claim
21 words
A composition as defined in claim 46 wherein the photoinitiator is selected from diazonium salts or onium salts, or mixtures thereof.
Claim 49
Dependent Claim
43 words
A Composition as defined in claims 1 which contains an unsubstituted cycloaliphatic monoepoxide or a substituted cycloaliphatic monoepoxide, said substituted cycloaliphatic monoepoxide contains substituents selected from an alkyl of 1 to 9 carbon atoms, halogen, oxygen, ether, ester, hydroxyl or a vinyl radical.
Claim 50
Dependent Claim
17 words
A composition as defined in claim 48 wherein the substituted cycloaliphatic monoepoxide is vinyl substituted cycloaliphatic monoepoxide.
Claim 51
Dependent Claim
17 words
A composition as defined in claim 49 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 52
Dependent Claim
17 words
A composition as defined in claim 49 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 53
Dependent Claim
17 words
A composition as defined in claim 49 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 54
Dependent Claim
17 words
A composition as defined in claim 49 wherein the substituted cycloaliphatic monoepoxide is hydroxyl substituted cycloaliphatic monoepoxide.
Claim 55
Dependent Claim
18 words
A composition as defined in claim 53 wherein the hydroxyl substituted cycloaliphatic monoepoxide is of the following formula:
Claim 56
Dependent Claim
15 words
A composition as defined in claim 48 wherein the unsubstituted cycloaliphatic monoepoxide is cyclohexene monoeposide.
Claim 57
Dependent Claim
11 words
A radiation cured coating derived from the composition of claim 1.
Claim 58
Dependent Claim
13 words
A composition as defined in claim 27 which contains a linear vinyl ether.
Claim 59
Dependent Claim
19 words
A composition as defined in claim 57 which comprises a linear vinyl ether that is an alkyl vinyl ether.
Claim 60
Dependent Claim
16 words
A composition as defined in claim 57 wherein the linear ether is an aryl vinyl ether.
Claim 61
Dependent Claim
16 words
A composition as defined in claim 57 wherein the linear vinyl ether is a divinyl ether.
Claim 62
Dependent Claim
13 words
A composition as defined in claim 40 which contains a linear vinyl ether.
Claim 63
Dependent Claim
19 words
A composition as defined in claim 61 which comprises a linear vinyl ether that is an alkyl vinyl ether.
Claim 64
Dependent Claim
16 words
A composition as defined in claim 61 wherein the linear ether is an aryl vinyl ether.
Claim 65
Dependent Claim
16 words
A composition as defined in claim 61 wherein the linear vinyl ether is a divinyl ether.
Claim 66
Dependent Claim
11 words
A composition as defined in claim 27 which contains a photoinitiator.
Claim 67
Dependent Claim
21 words
A composition as defined in claim 65 wherein the photoinitiator is selected from diazonium salts or onium salts, or mixtures thereof.
Claim 68
Dependent Claim
11 words
A composition as defined in claim 40 which contains a photoinitiator.
Claim 69
Dependent Claim
21 words
A composition as defined in claim 67 wherein the photoinitiator is selected from diazonium salts or onium salts, or mixtures thereof.
Claim 70
Dependent Claim
15 words
A composition as defined in claim 27 which contains a substitute or unsubstituted cycloaliphatic monoepoxide.
Claim 71
Dependent Claim
33 words
A composition as defined in claim 69 which comprises a substituted cycloaliphatic monoepoxide containing substituents selected from alkyl of 1 to 9 carbon atoms, halogen, oxygen, ether, ester, hydroxyl or a vinyl radical.
Claim 72
Dependent Claim
17 words
A composition as defined in claim 70 wherein the substituted cycloaliphatic monoepoxide is vinyl substituted cycloaliphatic monoepoxide.
Claim 73
Dependent Claim
17 words
A composition as defined in claim 70 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 74
Dependent Claim
17 words
A composition as defined in claim 70 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 75
Dependent Claim
17 words
A composition as defined in claim 70 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 76
Dependent Claim
15 words
A composition as defined in claim 74 wherein the unsubstituted cycloaliphatic monoepoxide is cyclohexene monoepoxide.
Claim 77
Dependent Claim
18 words
A composition as defined in claim 69 wherein the hydroxyl substituted cycloaliphatic monoepoxide is of the following formula:
Claim 78
Dependent Claim
15 words
A composition as defined in claim 40 which contains a substituted or unsubstituted cycloaliphatic monoepoxide.
Claim 79
Dependent Claim
33 words
A composition as defined in claim 77 which comprises a substituted cycloaliphatic monoepoxide containing substituents selected from alkyl of 1 to 9 carbon atoms, halogen, oxygen, ether, ester, hydroxyl or a vinyl radical.
Claim 80
Dependent Claim
17 words
A composition as defined in claim 78 wherein the substituted cycloaliphatic monoepoxide is vinyl substituted cycloaliphatic monoepoxide.
Claim 81
Dependent Claim
17 words
A composition as defined in claim 78 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 82
Dependent Claim
17 words
A composition as defined in claim 78 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 83
Dependent Claim
17 words
A composition as defined in claim 78 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:
Claim 84
Dependent Claim
15 words
A composition as defined in claim 82 wherein the unsubstituted cycloaliphatic monoepoxide is cyclohexene monoepoxide.
Claim 85
Dependent Claim
18 words
A composition as defined in claim 77 wherein the hydroxyl substituted cycloaliphatic monoepoxide is of the following formula:
References Cited (Backward Citations)
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