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US4908229A
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Method for producing an article containing a radiation cross-linked polymer and the article produced thereby
Assignee: Rohm and Haas Co
•
Filing: 1988-09-09
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Granted: 1990-03-13
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Expires: 2008-09-09
Abstract
Abstract A polymer comprising pendant functional groups having the formula ##STR1## wherein R 1 is a divalent radical and X is selected from the group consisting of organoacyl and cyano, is cross-linked by exposure to radiation having a wavelength in the range of about 10 -3 to about 400 nm.
Inventors
- 👤 Charles L. Kissel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:47
CPC Classifications
D; D06; D06M; D06M15/00; D06M15/19; D06M15/21; D06M15/263; D06M15/285; D21; D21H; D21H17/00; D21H17/20; D21H17/33; D21H17/34; D21H17/38; D21H19/00; D21H19/10; D21H19/14; D21H19/16; D21H25/00; D21H25/04; D21H25/06; C; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/26; C08F220/28; C08F220/283
Claims Analysis
Total Claims: 60
Claim 1
Independent Claim
120 words
A method of producing an article comprising the steps of: (a) contacting a substrate with a polymer to form a substrate/polymer combination, the polymer comprising (i) at least about 10 weight percent olefinically unsaturated, carboxylic acid ester monomers, (ii) a backbone and (iii) a plurality of pendant functional groups, the pendant functional groups having the formula selected from the group consisting of ##STR14## wherein R 1 is a divalent radical; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; and (b) curing the polymer by exposing the substrate/polymer combination to radiation having a wavelength within the range of about 10 -3 to about 400 nm.
Claim 2
Independent Claim
120 words
A method of producing an article comprising the steps of: (a) contacting a substrate with a polymer to form a substrate/polymer combination, the polymer comprising (i) at least about 10 weight percent olefinically unsaturated, carboxylic acid ester monomers, (ii) a backbone and (iii) a plurality of pendant functional groups, the pendant functional groups having the formula selected from the group consisting of ##STR14## wherein R 1 is a divalent radical; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; and (b) curing the polymer by exposing the substrate/polymer combination to radiation having a wavelength within the range of about 10 -3 to about 400 nm.
Claim 3
Dependent Claim
11 words
The method of claim 1 wherein the radiation is ultraviolet light.
Claim 4
Dependent Claim
22 words
The method of claim 2 wherein the ultraviolet light has a wavelength in the range of about 10 to about 300 nm.
Claim 5
Dependent Claim
22 words
The method of claim 2 wherein the ultraviolet light has a wavelength in the range of about 10 to about 250 nm.
Claim 6
Dependent Claim
19 words
The method of claim 2 wherein the ultraviolet light has a wavelength of about 10 to about 225 nm.
Claim 7
Dependent Claim
19 words
The method of claim 2 wherein the ultraviolet light has a wavelength of about 225 to about 265 nm.
Claim 8
Dependent Claim
25 words
The method of claim 1 wherein the substrate/polymer combination is exposed to the radiation for a period of time of up to about 15 minutes.
Claim 9
Dependent Claim
14 words
The method of claim 1 wherein the polymer is a constituent of a solution.
Claim 10
Dependent Claim
14 words
The method of claim 1 wherein the polymer is a constituent of a colloid.
Claim 11
Dependent Claim
17 words
The method of claim 9 wherein the colloid has a pH of about 2 to about 8.
Claim 12
Dependent Claim
31 words
The method of claim 1 wherein R 2 is hydrogen or an alkyl group containing up to about 10 atoms in addition to any hydrogen atoms present in the alkyl group.
Claim 13
Dependent Claim
75 words
The method of claim 1 wherein pendant functional groups have the formula ##STR15## wherein Y is selected from the group consisting of O, S, and NR 4 ; Z is selected from the group consisting of O, S, and NR 4 : R 3 is a divalent organic radical at least 2 atoms in length; and R 4 is selected from the group consisting of H and hydrocarbyl radicals having up to 6 carbon atoms.
Claim 14
Dependent Claim
9 words
The method of claim 12 wherein Y is O.
Claim 15
Dependent Claim
9 words
The method of claim 12 wherein Z is O.
Claim 16
Dependent Claim
14 words
The method of claim 12 wherein R 3 comprises up to about 40 atoms.
Claim 17
Dependent Claim
14 words
The method of claim 12 wherein R 3 comprises up to about 20 atoms.
Claim 18
Dependent Claim
23 words
The method of claim 12 wherein R 3 is selected from the group consisting of substituted and unsubstituted alkylenes, polyoxyalkylenes, polythiolalkylenes, and polyaminoalkylenes.
Claim 19
Dependent Claim
54 words
The method of claim 12 wherein R 3 is selected from the group consisting of ##STR16## wherein m is 0 or 1; n is 0 or 1; R 6 is a divalent organic radical at least one atom in length; and R 7 is a divalent organic radical at least one atom in length.
Claim 20
Dependent Claim
15 words
The method of claim 1 wherein R 2 contains up to about 6 carbon atoms.
Claim 21
Dependent Claim
10 words
The method of claim 19 wherein R 2 is methyl.
Claim 22
Dependent Claim
11 words
The method of claim 1 wherein the substrate is a textile.
Claim 23
Dependent Claim
21 words
The method of claim 1 further comprising the step of forming the backbone by combining one or more olefinically unsaturated monomers.
Claim 24
Dependent Claim
40 words
The method of claim 22 wherein at least one of the olefinically unsaturated monomers has the formula ##STR17## wherein R 9 and R 10 are each independently selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals.
Claim 25
Dependent Claim
37 words
The method of claim 23 wherein at least one of the monomers is selected from the group consisting of (a) monocarboxylic acid esters, (b) polycarboxylic acid esters, (c) salts of (a) and (b), and (d) mixtures thereof.
Claim 26
Dependent Claim
28 words
The method of claim 23 wherein at least one of the monomers is selected from the group consisting of acrylic acid, itaconic acid, hydroxyethyl acrylate, acrylonitrile, and acrylamide.
Claim 27
Dependent Claim
20 words
The method of claim 1 wherein the polymer comprises at least about 0.5 weight percent of the pendant functional groups.
Claim 28
Dependent Claim
20 words
The method of claim 1 wherein the polymer comprises up to about 20 weight percent of the pendant functional groups.
Claim 29
Independent Claim
147 words
A method of producing an article comprising the steps of: (a) reacting one or more monomers with at least one polymerizable functional monomer to form a polymer, the polymer comprising at least about 10 weight percent olefinically unsaturated, carboxylic acid ester monomers, and the polymerizable functional monomer having the formula: ##STR18## wherein R 1 is a divalent organic radical of at least 3 atoms in length; R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; R 9 is selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; R 10 is selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; (b) contacting the polymer with a substrate to form a substrate/polymer combination; and (c) curing the substrate/polymer combination by exposing the substrate/polymer combination to ultraviolet light.
Claim 30
Independent Claim
147 words
A method of producing an article comprising the steps of: (a) reacting one or more monomers with at least one polymerizable functional monomer to form a polymer, the polymer comprising at least about 10 weight percent olefinically unsaturated, carboxylic acid ester monomers, and the polymerizable functional monomer having the formula: ##STR18## wherein R 1 is a divalent organic radical of at least 3 atoms in length; R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; R 9 is selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; R 10 is selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; (b) contacting the polymer with a substrate to form a substrate/polymer combination; and (c) curing the substrate/polymer combination by exposing the substrate/polymer combination to ultraviolet light.
Claim 31
Dependent Claim
76 words
The method of claim 28 wherein the polymerizable functional monomer has the formula ##STR19## wherein Y is selected from the group consisting of O, S, and NR 4 ; Z is selected from the group consisting of O, S, and NR 4 ; R 3 is a divalent organic radical having at least two atoms; and R 4 is selected from the group consisting of hydrogen and hydrocarbyl radicals containing up to about 6 carbon atoms.
Claim 32
Dependent Claim
20 words
The method of claim 28 wherein the polymerizable functional monomer has the formula selected from the group consisting of ##STR20##
Claim 33
Independent Claim
101 words
A method of curing a polymer comprising the step of exposing the polymer to radiation having a wavelength within the range of about 10 -3 to about 400 nm, the polymer comprising (i) a backbone, (ii) at least about 10 weight percent olefinically unsaturated, carboxylic acid ester monomers, and (iii) a plurality of pendant functional groups, the pendant functional groups having the formula selected from the group consisting of ##STR21## wherein R 1 is a divalent radical; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals.
Claim 34
Independent Claim
101 words
A method of curing a polymer comprising the step of exposing the polymer to radiation having a wavelength within the range of about 10 -3 to about 400 nm, the polymer comprising (i) a backbone, (ii) at least about 10 weight percent olefinically unsaturated, carboxylic acid ester monomers, and (iii) a plurality of pendant functional groups, the pendant functional groups having the formula selected from the group consisting of ##STR21## wherein R 1 is a divalent radical; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals.
Claim 35
Dependent Claim
11 words
The method of claim 31 wherein the radiation is ultraviolet light.
Claim 36
Dependent Claim
31 words
The method of claim 31 wherein R 2 is hydrogen or an alkyl group containing up to about 10 atoms in addition to any hydrogen atoms present in the alkyl group.
Claim 37
Dependent Claim
75 words
The method of claim 31 wherein pendant functional groups have the formula ##STR22## wherein Y is selected from the group consisting of O, S, and NR 4 ; Z is selected from the group consisting of O, S, and NR 4 ; R 3 is a divalent organic radical at least 2 atoms in length; and R 4 is selected from the group consisting of H and hydrocarbyl radicals having up to 6 carbon atoms.
Claim 38
Dependent Claim
21 words
The method of claim 31 further comprising the step of forming the backbone by combining one or more olefinically unsaturated monomers.
Claim 39
Dependent Claim
40 words
The method of claim 35 wherein at least one of the olefinically unsaturated monomers has the formula ##STR23## wherein R 9 and R 10 are each independently selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals.
Claim 40
Independent Claim
116 words
A method of curing a polymer comprising the step of exposing the polymer to radiation having a wavelength within the range of about 10 -3 to about 400 nm, the polymer comprising at least about 10 weight percent olefinically unsaturated, carboxylic acid ester monomers, and being formed by reacting one or more monomers with at least one polymerizable functional monomer having the formula: ##STR24## wherein R 1 is a divalent radical; R 9 and R 10 are each independently selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals.
Claim 41
Independent Claim
116 words
A method of curing a polymer comprising the step of exposing the polymer to radiation having a wavelength within the range of about 10 -3 to about 400 nm, the polymer comprising at least about 10 weight percent olefinically unsaturated, carboxylic acid ester monomers, and being formed by reacting one or more monomers with at least one polymerizable functional monomer having the formula: ##STR24## wherein R 1 is a divalent radical; R 9 and R 10 are each independently selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals.
Claim 42
Dependent Claim
45 words
The method of claim 37 wherein the polymerizable functional radical has the formula: ##STR25## wherein R 2 is selected from the group consisting of hydrogen and alkyl groups containing up to about 10 atoms in addition to any hydrogen atoms present in the alkyl group.
Claim 43
Dependent Claim
76 words
The method of claim 37 wherein the polymerizable functional monomer has the formula ##STR26## wherein Y is selected from the group consisting of O, S, and NR 4 ; Z is selected from the group consisting of O, S, and NR 4 ; R 3 is a divalent organic radical having at least two atoms; and R 4 is selected from the group consisting of hydrogen and hydrocarbyl radicals containing up to about 6 carbon atoms.
Claim 44
Dependent Claim
20 words
The method of claim 37 wherein the polymerizable functional monomer has the formula selected from the group consisting of ##STR27##
Claim 45
Dependent Claim
21 words
The method of claim 37 wherein the polymer is exposed to radiation for a period of up to about 15 minutes.
Claim 46
Independent Claim
105 words
A method for producing an article comprising the steps of: (a) contacting a substrate with a polymer to form a substrate/polymer combination, the polymer comprising a backbone and a plurality of pendant functional groups, the pendant functional groups having the formula selected from the group consisting of ##STR28## wherein R 1 is a divalent radical; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; and (b) curing the polymer by exposing the substrate/polymer combination to radiation having a wavelength within the range of about 10 -3 to about 400 nm.
Claim 47
Independent Claim
105 words
A method for producing an article comprising the steps of: (a) contacting a substrate with a polymer to form a substrate/polymer combination, the polymer comprising a backbone and a plurality of pendant functional groups, the pendant functional groups having the formula selected from the group consisting of ##STR28## wherein R 1 is a divalent radical; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; and (b) curing the polymer by exposing the substrate/polymer combination to radiation having a wavelength within the range of about 10 -3 to about 400 nm.
Claim 48
Dependent Claim
31 words
The method of claim 42 wherein R 2 is hydrogen or an alkyl group containing up to about 10 atoms in addition to any hydrogen atoms present in the alkyl group.
Claim 49
Dependent Claim
21 words
The method of claim 42 wherein R 2 is hydrogen or an alkyl group comprising up to about 6 carbon atoms.
Claim 50
Dependent Claim
10 words
The method of claim 42 wherein R 2 is methyl.
Claim 51
Dependent Claim
75 words
The method of claim 42 wherein pendant functional groups have the formula ##STR29## wherein Y is selected from the group consisting of O, S, and NR 4 ; Z is selected from the group consisting of O, S, and NR 4 ; R 3 is a divalent organic radical at least 2 atoms in length; and R 4 is selected from the group consisting of H and hydrocarbyl radicals having up to 6 carbon atoms.
Claim 52
Dependent Claim
37 words
The method of claim 46 wherein R 2 is selected from the group consisting of hydrogen or an alkyl group containing up to about 10 atoms in addition to any hydrogen atoms present in the alkyl group.
Claim 53
Dependent Claim
21 words
The method of claim 46 wherein R 2 is hydrogen or an alkyl group comprising up to about 6 carbon atoms.
Claim 54
Dependent Claim
10 words
The method of claim 46 wherein R 2 is methyl.
Claim 55
Independent Claim
131 words
A method of producing an article comprising the steps of: (a) reacting one or more monomers with at least one polymerizable functional monomer to form a polymer, the polymerizable functional monomer having the formula: ##STR30## wherein R 1 is a divalent organic radical of at least 3 atoms in length; R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; R 9 is selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; R 10 is selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; (b) contacting the polymer with a substrate to form a substrate/polymer combination; and (c) curing the substrate/polymer combination by exposing the substrate/polymer combination to ultraviolet light.
Claim 56
Independent Claim
131 words
A method of producing an article comprising the steps of: (a) reacting one or more monomers with at least one polymerizable functional monomer to form a polymer, the polymerizable functional monomer having the formula: ##STR30## wherein R 1 is a divalent organic radical of at least 3 atoms in length; R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; R 9 is selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; R 10 is selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals; (b) contacting the polymer with a substrate to form a substrate/polymer combination; and (c) curing the substrate/polymer combination by exposing the substrate/polymer combination to ultraviolet light.
Claim 57
Independent Claim
86 words
A method for curing a polymer comprising the step of exposing the polymer to radiation having a wavelength within the range of about 10 -3 to about 400 nm, the polymer comprising a backbone and a plurality of pendant functional groups, the pendant functional groups having the formula selected from the group consisting of: ##STR31## wherein R 1 is a divalent radical; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals.
Claim 58
Independent Claim
86 words
A method for curing a polymer comprising the step of exposing the polymer to radiation having a wavelength within the range of about 10 -3 to about 400 nm, the polymer comprising a backbone and a plurality of pendant functional groups, the pendant functional groups having the formula selected from the group consisting of: ##STR31## wherein R 1 is a divalent radical; and R 2 is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals.
Claim 59
Independent Claim
103 words
A method for curing a polymer comprising the step of exposing the polymer to radiation having a wavelength within the range of about 10 -3 to about 400 nm, the polymer being formed by reacting one or more monomers with at least one polymerizable functional monomer having the formula: ##STR32## wherein R 1 is a divalent organic radical; R 2 is selected from the group consisting of hydrogen and alkyl arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; and R 9 and R 10 are each independently selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals.
Claim 60
Independent Claim
103 words
A method for curing a polymer comprising the step of exposing the polymer to radiation having a wavelength within the range of about 10 -3 to about 400 nm, the polymer being formed by reacting one or more monomers with at least one polymerizable functional monomer having the formula: ##STR32## wherein R 1 is a divalent organic radical; R 2 is selected from the group consisting of hydrogen and alkyl arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and arylalkenyl radicals; and R 9 and R 10 are each independently selected from the group consisting of hydrogen, halo, thio, and monovalent organic radicals.
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