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Patent US5164461 - Addition-curable silicone adhesive compositions - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsA fast curing, addition-curable silicone composition curable to form an adhesive having good physical properties and improved lap shear adhesive properties, comprising (A) a vinyl-containing polydiorganosiloxane composition, (B) a hydrogen-terminated polysiloxane in an amount sufficient to provide an...http://www.google.com/patents/US5164461?utm_source=gb-gplus-sharePatent US5164461 - Addition-curable silicone adhesive compositionsAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS5164461 APublication typeGrantApplication numberUS 07/669,266Publication dateNov 17, 1992Filing dateMar 14, 1991Priority dateMar 14, 1991Fee statusPaidAlso published asCA2061974A1, DE69232226D1, DE69232226T2, EP0503975A2, EP0503975A3, EP0503975B1Publication number07669266, 669266, US 5164461 A, US 5164461A, US-A-5164461, US5164461 A, US5164461AInventorsTyrone D. Mitchell, Mark W. Davis, Stuart R. Kerr, IIIOriginal AssigneeGeneral Electric CompanyExport CitationBiBTeX, EndNote, RefManPatent Citations (10), Referenced by (58), Classifications (15), Legal Events (7) External Links: USPTO, USPTO Assignment, EspacenetAddition-curable silicone adhesive compositions
1. A solventless, addition-curable silicone composition curable at relatively low temperature to form an adhesive having good physical properties and good adhesive properties, comprising by weight:(A) 100 parts of a vinyl-containing polydiorganosiloxane composition comprising:(1) from about 60 to about 75 parts by weight of an essentially cyclic-free vinyl-terminated polydiorganosiloxane having the general formula: R2 ViSiO(R2 SiO)m (RViSiO)n SiR2 Vi(i) wherein Vi represents a vinyl radical, R is selected from the class consisting of alkyl radicals of 1 to 8 carbon atoms, phenyl radicals, fluoroalkyl radicals of 3 to 10 carbon atoms and mixtures thereof, wherein "m+n" is a number sufficient to provide a viscosity of 65,000 to about 95,000 centipoise at 25° C., the vinyl content of the polydiorganosiloxane being from about 0.02 to about 2.0 weight %, and (2) from about 25 to about 40 parts by weight of a solid, benzene-soluble vinyl-containing resin copolymer comprising R1 3 SiO1/2 units and SiO4/2 units      (i) wherein each R1 is a vinyl radical or a monovalent hydrocarbon radical free of aliphatic unsaturation and containing no more than six carbon atoms, the ratio of R1 3 SiO1/2 units to SiO4/2 units from about 0.5:1 to about 1.5:1, the resin having a vinyl content of from about 1.5 to about 3.5% by weight; (B) a hydrogen-containing polysiloxane having an average unit formula R2 a Hb SiO.sub.(4-a-b)/2,                   (ii) wherein R2 is a monovalent hydrocarbon radical or halogenated monovalent hydrocarbon radical having from 1 to about 10 carbon atoms and free of aliphatic unsaturation, "a" is a value of from about 0 to about 3, "b" is a value of from about 0 to about 3, and the sum of "a"+"b" is from 0 to 3, there being at least two silicon-bonded hydrogen atoms per molecule; the polysiloxane being present in an amount sufficient to provide an adhesion-promoting molar ratio of silicon-bonded hydrogen atoms in (B) to olefinically unsaturated radicals in (A); (C) a catalytic amount of a hydrosilation catalyst; (D) an effective amount of an adhesion promoter selected from the group consisting of(i) bis[3-(trimethoxysilyl)alkyl]fumarates having the general formula: ##STR8## (ii) bis[3-(trimethoxysilyl)alkyl]maleates having the general formula: ##STR9## (iii) mixtures of (i) and (ii); (iv) allyl-[3-(trimethoxysilyl)alkyl]maleates having the general formula: ##STR10## (v) allyl-[3-(trimethoxysilyl)alkyl]fumarates having the general formula ##STR11## and (vi) N-[3-(trimethoxysilyl)alkyl]maleimides having the general formula ##STR12## wherein R3, R4, and R5 are each alkyl radicals of 1 to about 8 carbon atoms; and (E) from about 0 to about 200 parts of an extending filler; and (F) from about 0 to about 50 parts of a reinforcing filler; provided that (F) must be present if (A)(2) is absent. 2. A composition according to claim 1 wherein R3, R4, and R5 are each alkyl radicals of 1 to about 4 carbon atoms.
25. A solventless, addition-curable silicone composition curable at relatively low temperature to form an adhesive having good physical properties and good adhesive properties, comprising by weight:(A) 100 parts of a vinyl-containing polydimethylsiloxane composition comprising from about 60 to about 75 parts by weight of a linear vinyl-terminated polydimethylsiloxane having a viscosity of from about 3000 to about 5000 centipoise at 25° C., the vinyl content of the polydiorganosiloxane being from about 0.02 to about 2.0 weight %; and (2) from about 25 to about 40 parts by weight of the solid, benzene-soluble vinyl-containing resin copolymer comprising (CH3)3 SiO1/2 units and SiO4/2 units, the ratio of (CH3)3 SiO1/2 units to SiO4/2 units from about 0.5:1 to about 1.5:1, the resin having a vinyl content of from about 1.5 to about 3.5% by weight; (B) a hydrogen-siloxane copolymer resin comprising SiO4/2 units and R2 2 HSiO1/2 units; the ratio of R2 2 HSiO1/2 units to SiO4/2 units being from about 1 to about 2, the hydrogensiloxane copolymer resin having a hydrogen content of from about 0.8 to about 1.2% by weight and wherein R2 is a monovalent hydrocarbon radical or a halogenated monovalent hydrocarbon radical having from 1 to about 10 carbon atoms and free of aliphatic unsaturation; (C) a catalytic amount of a platinum-containing hydrosilation catalyst is selected from the group consisting of (i) a platinum catalyst solution comprising about 90.9% by weight of octyl alcohol and 9.1% by weight of chloroplatinic acid and (ii) a platinum complex formed by reacting chloroplatinic acid with tetravinylcyclotetrasiloxane in the presence of sodium bicarbonate in an ethanol solution; (D) from about 0.75 to about 1.25% by weight of an adhesion promoter selected from the group consisting of (i) bis[3-(trimethoxysilyl)propyl]fumarates, (ii) bis[3-(trimethoxysilyl)propyl]maleates; and (iii) mixtures of (i) and (ii); (E) 0 parts of alpha-quartz; and (F) from about 20 to about 50 parts of a treated fumed silica filler. 26. The cured composition of claim 25.
27. A solventless, addition-curable silicone composition curable at relatively low temperature to form an adhesive having good physical properties and good adhesive properties, comprising by weight:(A) 100 parts by weight of a blend containing(1) a blend containing from about 25 to about 35 parts by weight of a vinyl-containing polydiorganosiloxane of formula (1) and having a viscosity of 3000 to about 5000 centipoise at 25° C. and from about 65 to about 75 parts by weight of a vinyl-containing polydiorganosiloxane of formula (1) above and having a viscosity of 75,000 to about 95,000 centipoise at 25° C. the total amount of being 100 parts by weight; (2) from about 5.5 to about 7.5 parts by weight of a low viscosity polydiorganosiloxane composition having an average of at least one vinyldiorganosiloxy endgroup, a vinyl content of from about 0.2 to about 0.3% by weight and a viscosity of from about 400 to about 700 centipoise at 25° C.; (3) from about 5.5 to about 7.5 parts by weight of a low viscosity vinyldiorgano-endstopped vinylorganodiorganopolysiloxane having a vinyl content of from about 1.4 to about 2.0% by weight and a viscosity of from about 300 to about 600 centipoise at 25° C.; and (B) a hydrogen-siloxane copolymer resin comprising SiO4/2 units and R2 2 HSiO1/2 units; the ratio of R2 2 HSiO1/2 units to SiO4/2 being from about 1 to about 2, the hydrogensiloxane copolymer resin having a hydrogen content of from about 0.8 to about 1.2% by weight and wherein R2 is a monovalent hydrocarbon radical or a halogenated monovalent hydrocarbon radical having from 1 to about 10 carbon atoms and free of aliphatic unsaturation; (C) a catalytic amount of a platinum-containing hydrosilation catalyst is selected from the group consisting of (i) a platinum catalyst solution comprising about 90.9% by weight of octyl alcohol and 9.1% by weight of chloroplatinic acid and (ii) a platinum complex formed by reacting chloroplatinic acid with tetravinylcyclotetrasiloxane in the presence of sodium bicarbonate in an ethanol solution; (D) group consisting of (i) bis[3-(trimethoxysilyl)propyl]fumarates, (ii) bis[3-(trimethoxysilyl)propyl]maleates; and (iii) mixtures of (i) and (ii); (E) 0 parts of alpha-quartz; and (F) from about 20 to about 50 parts of a treated fumed silica filler. 28. A composition according to claim 27 wherein 0 parts by weight of alpha-quartz (E) is present.
(R2)3 SiO(HR2 SiO)e Si(R2)3 wherein R2 is as previously defined herein and "e" is a number sufficient to provide a viscosity of from about 15 to about 40 centistokes at 25° C.
TABLE 1______________________________________Examples 1-4: Formulations and Properties   Example No.Ingredient     1          2        3      4______________________________________HV-Polymer/     100        100      100    100Resin Blendalpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3BTMSPF    1.6        1.6      1.6    1.6Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Hydride Fluid     5.6        4.3      2.9    2H/C2 H3     2.09       1.61     1.08   0.75Shore A   60         53       40     28Tensile   850        792      663    455Elongation     255        283      378    380Lap Shear 720 (100)  612 (95) 270 (0)                                245 (20)100° C.(% CohesiveFailure)Lap Shear 776 (100)  737 (100)                         607 (100)                                467 (100)150° C.(% CohesiveFailure)______________________________________
TABLE 2______________________________________Comparison Examples A-D: Formulations and Properties   Example No.Ingredient     A          B        C      D______________________________________HV-Polymer/     100        100      100    100Resin Blendalpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Hydride Fluid     5.6        4.3      2.9    2H/C2 H3     2.09       1.61     1.08   0.75Shore A   64         60       55     36Tensile   920        895      760    620Elongation     220        240      240    365Lap Shear 615 (65)   510 (50) 185 (0)                                115 (20)100° C.(% CohesiveFailure)Lap Shear 800 (100)  700 (100)                         325 (10)                                405 (35)150° C.(% CohesiveFailure)______________________________________
TABLE 3______________________________________Examples 5-8: Formulations and Properties   Example No.Ingredient     5          6        7      8______________________________________LV-Polymer/     100        100      100    100Resin Blendalpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3BTMSPF    1.6        1.6      1.6    1.6Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Hydride Fluid     6.5        5        3.4    2.3H/C2 H3     2.11       1.62     1.10   0.75Shore A   63         56       45     27Tensile   1050       985      657    353Elongation     102        101      165    207Lap Shear 830 (100)  655 (85) 122 (0)                                84 (0)100° C.(% CohesiveFailure)Lap Shear 785 (100)  620 (100)                         532 (75)                                193 (25)150° C.(% CohesiveFailure)______________________________________
TABLE 4______________________________________Examples 9-12: Formulations and Properties   Example No.Ingredient     9          10       11     12______________________________________LV-Polymer/     100        100      100    100Resin BlendTreated Fumed     20         20       20     20Silica-IBTMSPF    1          1        1      1Catalyst  0.036      0.036    0.036  0.036Hydride Fluid     6.5        5        3.4    2.3H/C2 H3     2.11       1.62     1.10   0.75Shore A   64         57       47     31Tensile   960        920      775    415Elongation     140        155      260    290Lap Shear 625 (100)  465 (100)                         80 (0) 70 (0)100° C.(% CohesiveFailure)Lap Shear 670 (100)  715 (100)                         405 (75)                                150 (0)150° C.(% CohesiveFailure)______________________________________
TABLE 5______________________________________Comparison Examples E-H: Formulations and Properties   Example No.Ingredient     E          F        G      H______________________________________LV-Polymer/     100        100      100    100Resin BlendTreated Fumed     20         20       20     20Silica-ICatalyst  0.036      0.036    0.036  0.036Hydride Fluid     6.5        5        3.4    2.3H/C2 H3     2.11       1.62     1.10   0.75Shore A   60         58       52     37Tensile   1005       1045     845    890Elongation     160        180      190    370Lap Shear 625 (100)  580 (100)                         595 (100)                                250 (100)100° C.(% CohesiveFailure)Lap Shear 705 (100)  835 (100)                         705 (100)                                460 (100)150° C.(% CohesiveFailure)______________________________________
TABLE 6______________________________________Examples 13-16: Formulations and Properties   Example No.Ingredient     13         14       15     16______________________________________LV Polymer-I     100        100      100    100alpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3BTMSPF    1.6        1.6      1.6    1.6Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Hydride Fluid     1.45       1.1      0.75   0.53H/C2 H3     2.07       1.57     1.07   0.76Shore A   22         Too Soft Too Soft                                Too SoftTensile   185        --       --     --Elongation     185        --       --     --Lap Shear 135 (100)  75 (100) 35 (100)                                Fell100° C.                       Apart(% CohesiveFailure)Lap Shear 185 (100)  135 (100)                         45 (100)                                Fell150° C.                       Apart(% CohesiveFailure)______________________________________
TABLE 7______________________________________Examples 17-20: Formulations and Properties   Example No.Ingredient     17         18       19     20______________________________________HV-Polymer/     100        100      100    100Resin Blendalpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3BTMSPF    1.6        1.6      1.6    1.6Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Hydride Resin     6.4        5.6      4.3    2.9H/C2 H3     2.39       2.09     1.61   1.08Shore A   59         61       60     42Tensile   850        865      840    656Elongation     255        240      260    330Lap Shear 615 (100)  700 (100)                         445 (50)                                260 (0)100° C.(% CohesiveFailure)Lap Shear 840 (100)  805 (100)                         785 (100)                                590 (65)150° C.(% CohesiveFailure)______________________________________
TABLE 8______________________________________Comparative Examples I-L: Formulations and Properties   Example No.Ingredient     I          J        K      L______________________________________HV Polymer/     100        100      100    100Resin Blendalpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Hydride Resin     6.5        5.6      4.3    2.9H/C2 H3     2.39       2.09     1.61   1.08Shore A   64         65       67     50Tensile   840        850      895    745Elongation     225        265      240    290Lap Shear 95 (0)     95 (0)   70 (0) Fell100° C.                       ApartLap Shear 180 (0)    205 (0)  240 (0)                                175 (0)150° C.______________________________________
TABLE 9______________________________________Examples 21-24: Formulations and Properties   Example No.Ingredient     21         22       23     24______________________________________LV Polymer/     100        100      100    100Resin Blendalpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3BTMSPF    1.6        1.6      1.6    1.6Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Hydride Resin     7.4        6.5      5      3.4H/C2 H3     2.40       2.11     1.62   1.10Shore A   55         60       61     49Tensile   850        970      1025   810Elongation     120        125      118    165Lap Shear 660 (100)  680 (100)                         565 (60)                                231 (0)100° C.(% CohesiveFailure)Lap Shear 885 (100)  915 (100)                         705 (100)                                650 (65)150° C.(% CohesiveFailure)______________________________________
TABLE 10______________________________________Examples 25-28: Formulations and Properties   Example No.Ingredient     25         26       27     28______________________________________LV-Polymer/     100        100      100    100Resin BlendTreated Fumed     20         20       20     20Silica-IBTMSPF    1          1        1      1Catalyst  0.036      0.036    0.036  0.036Hydride Resin     7.4        6.5      5      3.4H/C2 H3     2.40       2.11     1.62   1.10Shore A   55         60       60     50Tensile   830        830      960    740Elongation     210        175      180    225Lap Shear 620 (100)  565 (100)                         470 (65)                                150 (0)100° C.(% CohesiveFailure)Lap Shear 645 (100)  770 (100)                         705 (100)                                630 (65)150° C.(% CohesiveFailure)______________________________________
TABLE 11______________________________________Comparison Examples M-P: Formulations and Properties   Example No.Ingredient     M          N        O      P______________________________________LV-Polymer/     100        100      100    100Resin BlendTreated Fumed     20         20       20     20Silica-ICatalyst  0.036      0.036    0.036  0.036Hydride Resin     7.4        6.5      5      3.4H/C2 H3     2.40       2.11     1.62   1.10Shore A   51         55       60     53Tensile   895        925      1060   980Elongation     270        215      195    210Lap Shear 30 (0)     30 (0)   40 (0) 30 (0)100° C.(% CohesiveFailure)Lap Shear 80 (0)     120 (0)  140 (0)                                105 (0)150° C.(% CohesiveFailure)______________________________________
TABLE 12______________________________________Examples 29-32: Formulations and Properties   Example No.Ingredient     29         30       31     32______________________________________HV-Polymer/     100        100      100    100Resin Blendalpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3BTMSPF    1.6        1.6      1.6    1.6Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Methyl-stopped     3.2        2.4      1.7    1.1Hydride FluidH/C2 H3     2.13       1.60     1.13   0.73Shore A   56         48       35     28Tensile   765        724      621    465Elongation     279        317      398    398Lap Shear 560 (100)  480 (100)                         435 (100)                                280 (100)100° C.(% CohesiveFailure)Lap Shear 660 (100)  550 (100)                         460 (100)                                390 (100)150° C.(% CohesiveFailure)______________________________________
TABLE 13______________________________________Examples 33-36: Formulations   Example No.Ingredient     33         34       35     36______________________________________LV-Polymer/     100        100      100    100Resin Blendalpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3BTMSPF    1.6        1.6      1.6    1.6Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Methyl-stopped     3.6        2.8      1.9    1.3Hydride FluidH/C2 H3     2.07       1.61     1.09   0.75Shore A   62         58       43     33Tensile   1037       942      521    263Elongation     123        135      140    140Lap Shear 780 (100)  465 (100)                         430 (100)                                260 (100)100° C.(% CohesiveFailure)Lap Shear 765 (100)  730 (100)                         695 (100)                                325 (100)150° C.(% CohesiveFailure)______________________________________
TABLE 14______________________________________Examples 37-40: Formulations and Properties   Example No.Ingredient     37         38       39     40______________________________________LV polymer-I     100        100      100    100alpha-quartz     47.2       47.2     47.2   47.2CaCO3     3          3        3      3BTMSPF    1.6        1.6      1.6    1.6Catalyst  0.048      0.048    0.048  0.048Inhibitor 0.0024     0.0024   0.0024 0.0024Methyl-stopped     0.82       0.63     0.43   0.29Hydride FluidH/C2 H3     2.08       1.60     1.09   0.74Shore A   29         Too Soft Too Soft                                Too SoftTensile   210        --       --     --Elongation     150        --       --     --Lap Shear 145 (100)  60 (100) 30 (100)                                Fell100° C.                       Apart(% CohesiveFailure)Lap Shear 245 (100)  85 (100) 25 (100)                                Fell150° C.                       Apart(% CohesiveFailure)______________________________________
TABLE 15______________________________________Examples 41-44: Formulations and Properties   Example No.Ingredient     41         42       43     44______________________________________LV polymer-I     100        100      100    100Treated Fumed     20         20       20     20Silica-IBTMSPF    1          1        1      1Catalyst  0.036      0.036    0.036  0.036Hydride Fluid     0.82       0.63     0.43   0.29H/C2 H3     2.07       1.57     1.07   0.76Shore A   29         Too Soft Too Soft                                Too SoftTensile   370        350      --     --Elongation     340        370      --     --Lap Shear 320 (100)  240 (100)                         105 (100)                                Fell100° C.                       Apart(% CohesiveFailure)Lap Shear 235 (100)  185 (100)                         85 (100)                                Fell150° C.                       Apart(% CohesiveFailure)______________________________________
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ClassificationC08K5/5425, C09J183/04European ClassificationC08K5/5425, C09J183/04Legal EventsDateCodeEventDescriptionMar 14, 1991ASAssignmentOwner name: GENERAL ELECTRIC COMPANY, A CORP OF NY, NEW YORKFree format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:DAVIS, MARK W.;KERR, STUART R. III;KERR, STUART R. III;REEL/FRAME:005655/0227Effective date: 19910314May 10, 1991ASAssignmentOwner name: GENERAL ELECTRIC COMPANY, NEW YORKFree format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:MITCHELL, TYRONE D.;REEL/FRAME:006056/0622Effective date: 19910318Apr 1, 1996FPAYFee paymentYear of fee payment: 4Mar 29, 2000FPAYFee paymentYear of fee payment: 8Mar 29, 2004FPAYFee paymentYear of fee payment: 12Jul 3, 2007ASAssignmentOwner name: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT,Free format text: SECURITY AGREEMENT;ASSIGNORS:MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC.;MOMENTIVE PERFORMANCE MATERIALS GMBH & CO. KG;MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK;REEL/FRAME:019511/0166Effective date: 20070228Jul 1, 2009ASAssignmentOwner name: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AFree format text: SECURITY AGREEMENT;ASSIGNORS:MOMENTIVE PERFORMANCE MATERIALS, INC.;JUNIPER BOND HOLDINGS I LLC;JUNIPER BOND HOLDINGS II LLC;AND OTHERS;REEL/FRAME:022902/0461Effective date: 20090615RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services