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US4698406A Expired / Lapsed US ⏱️ 0.0 years remaining

Curable organopolysiloxane composition

Assignee: Dow Silicones Corp
•
Filing: 1986-11-04
•
Granted: 1987-10-06
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Expires: 2006-11-04
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Abstract

Abstract A curable silicone composition comprising (i) an amine-functional organopolysiloxane and (ii) an acryl-functional organopolysiloxane selected from acyloxy-, methacryloxy or acrylamide-functional organopolysiloxanes is disclosed. Components (i) and (ii) of the composition cure by a Michael-type addition reaction to form a solid organopolysiloxane resin or elastomer. In a preferred embodiment, a room-temperature vulcanizable (RTV) elastomer results.

Inventors

  • 👤 Peter Y. K. Lo
  • 👤 Maris J. Ziemelis

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 16:49
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C08L; C08L83/00; C08L83/04; C08L83/08; Y; Y10; Y10S; Y10S528/00; Y10S528/901; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31652; Y10T428/31663

Claims Analysis

Total Claims: 50
Claim 1
Independent Claim 210 words
A curable composition comprising: (i) an amine-functional organopolysiloxane consisting of a plurality of independently selected units of the formula ##STR35## wherein X is an amine-functional organic group bearing at least one --NHR" group, in which R" is hydrogen or an alkyl radical having 1-6 carbon atoms, R is a group selected from alkyl, cycloalkyl, haloalkyl, aromatic or haloaromatic radicals, a has a value of 0, 1, 2, or 3, b has a value of 0, 1 or 2, and the sum (a+b) is less than 4, there being on average at least two X groups per molecule of said amine-functional organopolysiloxane; and (ii) an acryl-functional organopolysiloxane consisting of a plurality of independently selected units of the formula ##STR36## wherein Z is an acryl-functional organic group bearing at least one group selected from acryloxy, methacryloxy or acrylamide radicals, R has been previously defined, c has a value of 0, 1, 2, or 3, d has a value of 0, 1 or 2, and the sum (c+d) is less than 4, there being on average at least two Z groups per molecule of said acryl-functional organo-polysiloxane, and at least one of (i) and (ii) has an average of more than two of said X groups and said Z groups, respectively, per molecule.
Claim 2
Dependent Claim 210 words
A curable composition comprising: (i) an amine-functional organopolysiloxane consisting of a plurality of independently selected units of the formula ##STR35## wherein X is an amine-functional organic group bearing at least one --NHR" group, in which R" is hydrogen or an alkyl radical having 1-6 carbon atoms, R is a group selected from alkyl, cycloalkyl, haloalkyl, aromatic or haloaromatic radicals, a has a value of 0, 1, 2, or 3, b has a value of 0, 1 or 2, and the sum (a+b) is less than 4, there being on average at least two X groups per molecule of said amine-functional organopolysiloxane; and (ii) an acryl-functional organopolysiloxane consisting of a plurality of independently selected units of the formula ##STR36## wherein Z is an acryl-functional organic group bearing at least one group selected from acryloxy, methacryloxy or acrylamide radicals, R has been previously defined, c has a value of 0, 1, 2, or 3, d has a value of 0, 1 or 2, and the sum (c+d) is less than 4, there being on average at least two Z groups per molecule of said acryl-functional organo-polysiloxane, and at least one of (i) and (ii) has an average of more than two of said X groups and said Z groups, respectively, per molecule.
Claim 3
Dependent Claim 23 words
The composition of claim 1, wherein said R groups of components (i) and (ii) are independently selected from methyl, phenyl or 3,3,3-trifluoropropyl radicals.
Claim 4
Dependent Claim 58 words
The composition of claim 2, wherein said X group is represented by the formula --R'(NHCH.sub.2 CH.sub.2).sub.g NR"H in which R' is a divalent hydrocarbyl group having 3 to 6 carbon atoms, R" is selected from hydrogen or an alkyl radical having 1 to 6 carbon atoms and g is an integer having a value of zero to 4.
Claim 5
Dependent Claim 51 words
The composition of claim 3, wherein said Z group is represented by the formula --R"'OA in which R"' is a divalent hydrocarbon radical having 1 to 18 carbon atoms, or the corresponding oxyalkylene radical, and A is the radical ##STR37## in which B is selected from hydrogen or the methyl radical.
Claim 6
Dependent Claim 54 words
The composition of claim 3, wherein said Z group is represented by the formula ##STR38## in which R' is a divalent hydrocarbon group, m is an integer between 1 and 10, k is 0, 1, 2, 3, or 4, A is the group ##STR39## and B is selected from hydrogen or the methyl radical.
Claim 7
Dependent Claim 59 words
The composition of claim 3, wherein said Z group is selected from groups represented by the formulae --DNHG or --DNGDNHG in which D is a divalent saturated hydrocarbon radical having from 1 to 6 carbon atoms and G is the group ##STR40## where B is selected from hydrogen or the methyl radical and m' is 2, 3 or 4.
Claim 8
Dependent Claim 47 words
The composition of claim 3, wherein said Z group is represented by the formula --QNAQ'NAR"" in which Q and Q' denote divalent hydrocarbon radicals, R"" is hydrogen or a monovalent hydrocarbon radical, A is the group ##STR41## and B is selected from hydrogen or the methyl radical.
Claim 9
Dependent Claim 44 words
The composition of claim 3, wherein said Z group is represented by the formula ##STR42## in which R""' is a divalent hydrocarbon group having 3 to 6 carbon atoms, A is the group ##STR43## and B is selected from hydrogen or the methyl radical.
Claim 10
Dependent Claim 11 words
The composition of claim 8, wherein said R""' group is trimethylene.
Claim 11
Dependent Claim 32 words
The composition of claim 7, wherein said Q group is --CH 2 CH(CH 3 )CH 2 --, said Q' group is --CH 2 CH 2 -- and said R"" group is hydrogen.
Claim 12
Dependent Claim 90 words
The composition as delineated in claim 1, wherein said organopolysiloxane (i) is selected from linear copolymers having the average structure ##STR44## in which the average value of x can vary from zero to about 1000 and the average value of y can vary from 2 to about 100; and said organopolysiloxane (ii) is selected from linear copolymers having the average structure ##STR45## in which the average value of x' can vary from about 5 to about 500 and the average value of y' can vary from 2 to about 30.
Claim 13
Dependent Claim 23 words
The composition of claim 11, wherein said R groups of components (i) and (ii) are independently selected from methyl, phenyl or 3,3,3-trifluoropropyl radicals.
Claim 14
Dependent Claim 58 words
The composition of claim 12, wherein said X group is represented by the formula --R'(NHCH.sub.2 CH.sub.2).sub.g NR"H in which R' is a divalent hydrocarbyl group having 3 to 6 carbon atoms, R" is selected from hydrogen or an alkyl radical having 1 to 6 carbon atoms and g is an integer having a value of zero to 4.
Claim 15
Dependent Claim 51 words
The composition of claim 13, wherein said Z group is represented by the formula --R"'OA in which R'" is a divalent hydrocarbon radical having 1 to 18 carbon atoms, or the corresponding oxyalkylene radical, and A is the radical ##STR46## in which B is selected from hydrogen or the methyl radical.
Claim 16
Dependent Claim 54 words
The composition of claim 13, wherein said Z group is represented by the formula ##STR47## in which R' is a divalent hydrocarbon group, m is an integer between 1 and 10, k is 0, 1, 2, 3, or 4, A is the group ##STR48## and B is selected from hydrogen or the methyl radical.
Claim 17
Dependent Claim 59 words
The composition of claim 13, wherein said Z group is selected from groups represented by the formulae --DNHG or --DNGDNHG in which D is a divalent saturated hydrocarbon radical having from 1 to 6 carbon atoms and G is the group ##STR49## where B is selected from hydrogen or the methyl radical and m' is 2, 3 or 4.
Claim 18
Dependent Claim 47 words
The composition of claim 13, wherein said Z group is represented by the formula --QNAQ'NAR"" in which Q and Q' denote divalent hydrocarbon radicals, R"" is hydrogen or a monovalent hydrocarbon radical, A is the group ##STR50## and B is selected from hydrogen or the methyl radical.
Claim 19
Dependent Claim 44 words
The composition of claim 13, wherein said Z group is represented by the formula ##STR51## in which R""' is a divalent hydrocarbon group having 3 to 6 carbon atoms, A is the group ##STR52## and B is selected from hydrogen or the methyl radical.
Claim 20
Dependent Claim 22 words
The composition of claim 18, wherein said R""' group is trimethylene, said R group is methyl and said R' group is isobutylene.
Claim 21
Dependent Claim 42 words
The composition of claim 17, wherein said Q group is --CH 2 CH(CH 3 )CH 2 --, said Q' group is --CH 2 CH 2 --, said R"" group is hydrogen, said R group is methyl and said R' group is isobutylene.
Claim 22
Dependent Claim 215 words
A process for preparing a cured organopolysiloxane material, comprising: reacting (i) an amine-functional organopolysiloxane consisting of a plurality of independently selected units of the formula ##STR53## wherein X is an amine-functional organic group bearing at least one --NHR" group, in which R" is hydrogen or an alkyl radical having 1-6 carbon atoms, R is a group selected from alkyl, cycloalkyl, haloalkyl or aromatic radicals, a has a value of 0, 1, 2, or 3, b has a value of 0, 1 or 2, and the sum (a+b) is less than 4, there being on average at least two X groups per molecule of said amine-functional organopolysiloxane with (ii) an acryl-functional organopolysiloxane consisting of a plurality of independently selected units of the formula ##STR54## wherein Z is an acryl-functional organic group bearing at least one group selected from acryloxy, methacryloxy or acrylamide radicals, R has been previously defined, c has a value of 0, 1, 2, or 3, d has a value of 0, 1 or 2, and the sum (c+d) is less than 4, there being on average at least two Z groups per molecule of said acryl-functional organopolysiloxane, and at least one of (i) and (ii) has an average of more than two of said X groups and said Z groups, respectively, per molecule.
Claim 23
Dependent Claim 215 words
A process for preparing a cured organopolysiloxane material, comprising: reacting (i) an amine-functional organopolysiloxane consisting of a plurality of independently selected units of the formula ##STR53## wherein X is an amine-functional organic group bearing at least one --NHR" group, in which R" is hydrogen or an alkyl radical having 1-6 carbon atoms, R is a group selected from alkyl, cycloalkyl, haloalkyl or aromatic radicals, a has a value of 0, 1, 2, or 3, b has a value of 0, 1 or 2, and the sum (a+b) is less than 4, there being on average at least two X groups per molecule of said amine-functional organopolysiloxane with (ii) an acryl-functional organopolysiloxane consisting of a plurality of independently selected units of the formula ##STR54## wherein Z is an acryl-functional organic group bearing at least one group selected from acryloxy, methacryloxy or acrylamide radicals, R has been previously defined, c has a value of 0, 1, 2, or 3, d has a value of 0, 1 or 2, and the sum (c+d) is less than 4, there being on average at least two Z groups per molecule of said acryl-functional organopolysiloxane, and at least one of (i) and (ii) has an average of more than two of said X groups and said Z groups, respectively, per molecule.
Claim 24
Dependent Claim 24 words
The process according to claim 21, wherein said R groups of components (i) and (ii) are independently selected from methyl, phenyl or 3,3,3-trifluoropropyl radicals.
Claim 25
Dependent Claim 59 words
The process according to claim 22, wherein said X group is represented by the formula --R'(NHCH.sub.2 CH.sub.2).sub.g NR"H in which R' is a divalent hydrocarbyl group having 3 to 6 carbon atoms, R" is selected from hydrogen or an alkyl radical having 1 to 6 carbon atoms and g is an integer having a value of zero to 4.
Claim 26
Dependent Claim 48 words
The process according to claim 23, wherein said Z group is represented by the formula --QNAQ'NAR"" in which Q and Q' denote divalent hydrocarbon radicals, R"" is hydrogen or a monovalent hydrocarbon radical, A is the group ##STR55## and B is selected from hydrogen or the methyl radical.
Claim 27
Dependent Claim 45 words
The process according to claim 23, wherein said Z group is represented by the formula ##STR56## in which R""' is a divalent hydrocarbon group having 3 to 6 carbon atoms, A is the group ##STR57## and B is selected from hydrogen or the methyl radical.
Claim 28
Dependent Claim 18 words
The process according to claim 25, wherein said R""' group is trimethylene and said R group is methyl.
Claim 29
Dependent Claim 38 words
The process according to claim 24, wherein said Q group is --CH 2 CH(CH 3 )CH 2 --, said Q' group is --CH 2 CH 2 --, said R"" group is hydrogen and said R group is methyl.
Claim 30
Dependent Claim 89 words
The process according to claim 21, wherein said organopolysiloxane (i) is selected from linear copolymers having the average structure ##STR58## in which the average value of x can vary from zero to about 1000 and the average value of y can vary from 2 to about 100; and said organopolysiloxane (ii) is selected from linear copolymers having the average structure ##STR59## in which the average value of x' can vary from about 5 to about 500 and the average value of y' can vary from 2 to about 30.
Claim 31
Dependent Claim 24 words
The process according to claim 28, wherein said R groups of components (i) and (ii) are independently selected from methyl, phenyl or 3,3,3-trifluoropropyl radicals.
Claim 32
Dependent Claim 59 words
The process according to claim 29, wherein said X group is represented by the formula --R'(NHCH.sub.2 CH.sub.2).sub.g NR"H in which R' is a divalent hydrocarbyl group having 3 to 6 carbon atoms, R" is selected from hydrogen or an alkyl radical having 1 to 6 carbon atoms and g is an integer having a value of zero to 4.
Claim 33
Dependent Claim 48 words
The process according to claim 30, wherein said Z group is represented by the formula --QNAQ'NAR"" in which Q and Q' denote divalent hydrocarbon radicals, R"" is hydrogen or a monovalent hydrocarbon radical, A is the group ##STR60## and B is selected from hydrogen or the methyl radical.
Claim 34
Dependent Claim 45 words
The process according to claim 30, wherein said Z group is represented by the formula ##STR61## in which R""' is a divalent hydrocarbon group having 3 to 6 carbon atoms, A is the group ##STR62## and B is selected from hydrogen or the methyl radical.
Claim 35
Dependent Claim 43 words
The process according to claim 32, wherein said Q group is --CH 2 CH(CH 3 )CH 2 --, said Q' group is --CH 2 CH 2 --, said R"" group is hydrogen, said R group is methyl and said R' group is isobutylene.
Claim 36
Dependent Claim 23 words
The process according to claim 31, wherein said R""' group is trimethylene, said R group is methyl and said R' group is isobutylene.
Claim 37
Dependent Claim 14 words
The composition of claim 1, further comprising an inhibiting amount of a volatile acid.
Claim 38
Dependent Claim 14 words
The composition of claim 11, further comprising an inhibiting amount of a volatile acid.
Claim 39
Dependent Claim 14 words
The composition of claim 17, further comprising an inhibiting amount of a volatile acid.
Claim 40
Dependent Claim 14 words
The composition of claim 18, further comprising an inhibiting amount of a volatile acid.
Claim 41
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 1.
Claim 42
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 2.
Claim 43
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 3.
Claim 44
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 7.
Claim 45
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 8.
Claim 46
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 11.
Claim 47
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 12.
Claim 48
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 13.
Claim 49
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 17.
Claim 50
Dependent Claim 12 words
A cured organopolysiloxane reaction product of the composition defined by claim 18.

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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) 1990-10-05 1991-04-06 1991-10-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-10-05 1995-04-06 1995-10-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-10-05 1999-04-06 1999-10-06 $7700.00 Window Closed / Lapsed

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