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EP0336633A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

MTQ/polysiloxane hybrid resins, method of making the same, and coating/potting compositions containing the same

Assignee: Henkel Loctite Corp
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Filing: 1989-03-29
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Granted: —
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Expires: 2009-03-29
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Abstract

Abstract A polysiloxane comprising a linear polydiorganosiloxane chain joined at one terminus to any acrylic-functional end group, and joined at its other end to a polysiloxane moiety comprising a multiplicity of monofunctional siloxane units (M), trifunctional siloxane units (T), and tetrafunctional siloxane units (Q), wherein the concentration ratio of M units to the sum of T units and Q units, M/(T+Q), in the polysiloxane moiety is from about 0.55 to about 0.75, and wherein the number of siloxy repeating units in the linear polydiorganosiloxane chain is from 2 to 1000. The M and/or T units may also contain (meth)acrylate groups. The MTQ/silicone hybrid resins of the invention are curable by UV radiation, to provide high tensile strength silicone polymers characterized by low elongation, and viscosity which may be on the order of from about 10,000 to about 50,000 centipoise.

Inventors

  • 👤 Steven T. Nakos

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-01 08:46
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/20; C08G77/42; C08G77/44

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 170 words
A polysiloxane of the general formula: wherein: A is an acrylic-functional end group; R₁ and R₂ are each independently selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, haloalkyl, (meth)acryloxyalkyl, and (meth)acryloxyalkenyl; B is a multifunctional cross-linked polysiloxane moiety having a plurality of pendant hydroxy groups and comprising a multiplicity of monofunctional siloxane units (M), trifunctional siloxane units (T), tetrafunctional siloxane units (Q) wherein: p has a value of 0.5 when the associated oxygen atom is bonded to another silicon atom, and a value of 1 when the associated oxygen atom is bonded to other than a silicon atom, with the proviso that at least one p in each T and Q unit has a value of 0.5; each R is independently selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, haloalkyl, (meth)acryloxyalkyl, and (meth)acryloxyalkenyl; the concentration ratio of M units to the sum of T and Q units, M/(T+Q), in the cross-linked polysiloxane moiety is from about 0.55 to about 0.75; and n is 2 to 1000.
Claim 2
Dependent Claim 170 words
A polysiloxane of the general formula: wherein: A is an acrylic-functional end group; R₁ and R₂ are each independently selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, haloalkyl, (meth)acryloxyalkyl, and (meth)acryloxyalkenyl; B is a multifunctional cross-linked polysiloxane moiety having a plurality of pendant hydroxy groups and comprising a multiplicity of monofunctional siloxane units (M), trifunctional siloxane units (T), tetrafunctional siloxane units (Q) wherein: p has a value of 0.5 when the associated oxygen atom is bonded to another silicon atom, and a value of 1 when the associated oxygen atom is bonded to other than a silicon atom, with the proviso that at least one p in each T and Q unit has a value of 0.5; each R is independently selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, haloalkyl, (meth)acryloxyalkyl, and (meth)acryloxyalkenyl; the concentration ratio of M units to the sum of T and Q units, M/(T+Q), in the cross-linked polysiloxane moiety is from about 0.55 to about 0.75; and n is 2 to 1000.
Claim 3
Dependent Claim 21 words
A polysiloxane according to Claim 1, wherein A is selected from the group consisting of: wherein R₃ is H or alkyl.
Claim 4
Dependent Claim 17 words
A polysiloxane according to Claim 1 or 2, wherein M/(T+Q) is from about 0.60 to about 0.70.
Claim 5
Dependent Claim 28 words
A polysiloxane according to any of Claims 1 to 3, wherein the concentration of acrylic functionality is from about 0.60 to about 1.40 meq/gm solid of the polysiloxane.
Claim 6
Dependent Claim 31 words
A polysiloxane according to any of Claims 1 to 4, wherein said linear polydiorganosiloxane chains are joined to (meth)acrylic functional end groups selected from the group consisting of (meth)acryloxyalkyl and (meth)acryloxyalkenyl.
Claim 7
Dependent Claim 24 words
A UV curable composition comprising a polysiloxane according to any of Claims 1 to 5 and a photoinitiatingly effective amount of a UV photoinitiator.
Claim 8
Independent Claim 66 words
A method of making an MTQ/silicone hybrid resin, comprising the steps of: (a) forming a linear polydiorganosiloxane having acrylic and chloro end groups; (b) hydrolyzing tetraalkyl orthosilicate, an acrylic-functional trialkoxysiloxane, and a chlorotrialkylsilane, to form an MTQ resin comprising silanol functionally; (c) reacting said linear polydiorganosiloxane with said MTQ resin, to form an MTQ/silicone hybrid resin whose MTQ moiety comprises a plurality of pendant hydroxy groups.
Claim 9
Independent Claim 66 words
A method of making an MTQ/silicone hybrid resin, comprising the steps of: (a) forming a linear polydiorganosiloxane having acrylic and chloro end groups; (b) hydrolyzing tetraalkyl orthosilicate, an acrylic-functional trialkoxysiloxane, and a chlorotrialkylsilane, to form an MTQ resin comprising silanol functionally; (c) reacting said linear polydiorganosiloxane with said MTQ resin, to form an MTQ/silicone hybrid resin whose MTQ moiety comprises a plurality of pendant hydroxy groups.
Claim 10
Dependent Claim 35 words
A process according to Claim 7, wherein the mole ratio of M units to the sum of T units and Q units, M/(T+Q), in said MTQ/silicone hybrid resin is from about 0.55 to about 0.75.
Claim 11
Dependent Claim 28 words
A process according to Claim 7 or 8, wherein (meth)acrylate concentration in said MTQ/silicone hybrid resin is from about 0.28 meq/gram about 2.54 meq/gram of said hybrid resin.
Claim 12
Dependent Claim 31 words
A process according to any of Claims 7 to 9, wherein (meth)acrylate concentration in said MTQ/silicone hybrid resin is from about 0.60 meq/gram to about 1.4 meq/gram of said hybrid resin.
Claim 13
Dependent Claim 43 words
A process according to any of Claims 7 to 10, wherein the reaction of said MTQ resin and said linear polydiorganosiloxane is carried out for sufficient time and under sufficient conditions to react a majority of hydroxyl functional groups of said MTQ resin.
Claim 14
Dependent Claim 197 words
A polysiloxane comprising a linear polydiorganosiloxane chain joined at one end thereof to an acrylic-functional end group, and joined at its other end to a cross-linked polysiloxane moiety comprising a multiplicity of monofunctional siloxane units (M), trifunctional siloxane units (T), and tetrafunctional siloxane unit (Q), wherein: the concentration ratio of M units to the sum of T units and Q units, M/(T+Q), in the polysiloxane moiety is from about 0.55 to about 0.75; the number of siloxy repeating units in the linear diorganopolysiloxane chain is from 2 to 1000; said polysiloxane moiety is formed as an MTQ reaction product having T and Q hydroxyl functionally, by reaction of M, T, and Q silane reactants, the MTQ reaction product being reacted with a linear polydiorganosiloxane having said acrylic-functional end group at one end thereof and at its other end a functional group which is reactive with said hydroxy functionally, to join said linear polydiorganosiloxane chain to said MTQ reaction product; and the polysiloxane comprises silanol groups in said polysiloxane moiety in sufficient quantity relative to the number of acrylic-functional end groups present to render the polysiloxane self-curable by exposure to UV radiation in the presence of a photoinitiator.
Claim 15
Dependent Claim 197 words
A polysiloxane comprising a linear polydiorganosiloxane chain joined at one end thereof to an acrylic-functional end group, and joined at its other end to a cross-linked polysiloxane moiety comprising a multiplicity of monofunctional siloxane units (M), trifunctional siloxane units (T), and tetrafunctional siloxane unit (Q), wherein: the concentration ratio of M units to the sum of T units and Q units, M/(T+Q), in the polysiloxane moiety is from about 0.55 to about 0.75; the number of siloxy repeating units in the linear diorganopolysiloxane chain is from 2 to 1000; said polysiloxane moiety is formed as an MTQ reaction product having T and Q hydroxyl functionally, by reaction of M, T, and Q silane reactants, the MTQ reaction product being reacted with a linear polydiorganosiloxane having said acrylic-functional end group at one end thereof and at its other end a functional group which is reactive with said hydroxy functionally, to join said linear polydiorganosiloxane chain to said MTQ reaction product; and the polysiloxane comprises silanol groups in said polysiloxane moiety in sufficient quantity relative to the number of acrylic-functional end groups present to render the polysiloxane self-curable by exposure to UV radiation in the presence of a photoinitiator.
Claim 16
Dependent Claim 23 words
A polysiloxane according to Claim 12 wherein the acrylic functional end group is selected from the group consisting of (meth) acryloxyalkyl and (meth)acryloxyalkenyl.
Claim 17
Dependent Claim 30 words
A polysiloxane according to Claims 12 and 13, wherein said linear polydiorganosiloxane chains are joined to (meth)acrylic functional end groups selected from the group consisting of (meth) acryloxyalkyl and (meth)acryloxyalkenyl.
Claim 18
Dependent Claim 22 words
A UV curable composition comprising a polysiloxane according to any of Claims 12 to 14 and an effective amount of UV photoinitiator.
Claim 19
Dependent Claim 25 words
A UV curable composition according to Claim 15, wherein the linear polydiorganosiloxane chain is a linear polydimethylsiloxane chain of from 2 to 1000 repeating units

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