Source: https://patents.google.com/patent/US5106928A/en
Timestamp: 2019-01-20 18:03:28
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US5106928A - Acrylic adhesive composition and organoboron initiator system - Google Patents
Acrylic adhesive composition and organoboron initiator system Download PDF
US5106928A
US5106928A US07692766 US69276691A US5106928A US 5106928 A US5106928 A US 5106928A US 07692766 US07692766 US 07692766 US 69276691 A US69276691 A US 69276691A US 5106928 A US5106928 A US 5106928A
US07692766
Nicholas V. Merlo
______________________________________AMINE         AMOUNT       INITIATOR NO.______________________________________ethylene diamine         6.0    g (0.10 m)                          Iethylene diamine         9.0    g (0.15 m)                          IIethylene diamine         12.0   g (0.20 m)                          III1,2-propylene diamine         11.1   g (0.15 m)                          IVn-octylamine  19.4   g (0.15 m)                          V1,6-diaminohexane         17.4   g (0.15 m)                          VIdiethylenetriamine         10.3   g (0.10 m)                          VII1,3-propylene diamine.sup.1         7.4    g (0.10 m)                          VIII4-aminomethylpyridine         10.8   g (0.10 m)                          IX3-aminomethylpyridine         10.8   g (0.10 m)                          Xdiethylamine  10.95  g (0.15 m)                          XI1,3-propylene diamine         11.1   g (0.15 m)                          XII______________________________________ .sup.1 1 molar solution of triethylboron in tetrahydrofuran used
______________________________________Part IStereon 840A (styrene-butadiene block copolymer)                      30    partsIsobornyl methacrylate     70    partsOrganoboron amine initiator No. 12.sup.1                      4     partsPart IIStereon 840A               30    partsIsobornyl methacrylate     61    partsMethacrylic acid           5     partsCumene hydroperoxide (CHP) 4     parts______________________________________ .sup.1 1 molar solution in tetrahydrofuran
__________________________________________________________________________    INITIATOR         BOND TENSILERUBBER (%)    (%)    % ACID.sup.1                 % CHP.sup.2                      STRENGTH PSI__________________________________________________________________________Stereon 840a (20)    XII (0.5)           10    0.1  1875Steroen 840a (25)    VIII (0.5)           1     1    1550Kraton 1107 (20).sup.3    II (0.5)           10    1    1850Kraton 1107 (20)    II (0.25)           10    1    1350Kraton 1107 (20)    II (1.0)           10    1    2100Hycar 4051 (10).sup.4    IV (0.5)           10    1    1200Kraton 1122 (25).sup.5    VI (0.5)           1     1    1500Stereon 840A (20)    I (0.5)           0.5   1.7  1500    also contains 13% octyl acrylateStereon 840A (30)    VIII (0.5)           10    1    2700    monomer was tetrahydrofurfuryl methacrylate__________________________________________________________________________ .sup.1 methacrylic acid .sup.2 cumene hydroperoxide .sup.3 styreneisoprene .sup.4 polyacrylic rubber polymer .sup.5 styreneisoprene
__________________________________________________________________________Part ISample No. Initiator      Rubber.sup.1           Monomer A                  Monomer B                         Monomer C__________________________________________________________________________3A-I  2 parts      25 parts           60 parts                  15 parts                         --           (IBOMA)                  (OMA)3B-I  2 parts      25 parts           60 parts                  15 parts                         --           (IBOMA)                  (OMA)3C-I  2 parts      25 parts           60 parts                  15 parts                         --           (IBOMA)                  (ODA)3D-I  2 parts      25 parts           60 parts                  15 parts                         --           (IBOMA)                  (HDDA)3E-I  2 parts      25 parts           60 parts                  15 parts                         --           (IBOMA)                  (HDDMA)3F-I  2 parts      30 parts           --     --     70 parts                         (THFMA)3G-I  2 parts      30 parts           --     --     70 parts                         (THFMA)3H-I  2 parts      30 parts           --     --     70 parts                         (THFMA)3I-I  2 parts      30 parts           --     --     70 parts                         (THFMA)3J-I  2 parts      30 parts           55 parts                  --     15 parts           (IBOMA)       (HPMA)__________________________________________________________________________Part IISample No. Rubber.sup.1      Monomer A             Monomer B                    Acid  CHP__________________________________________________________________________3A-II 25 parts      50 parts             15 parts                    10 parts                          --      (THFMA)             (OMA)  (MAA)3B-II 25 parts      50 parts             15 parts                    10 parts                          --      (IBOMA)             (OMA)  (MAA)3C-II 25 parts      50 parts             15 parts                    10 parts                          --      (THFMA)             (ODA)  (MAA)3D-II 25 parts      50 parts             15 parts                    10 parts                          --      (THFMA)             (HDDA) (MAA)3E-II 25 parts      50 parts             15 parts                    10 parts                          --      (THFMA)             (HDDMA)                    (MAA)3F-II 30 parts      60 parts             --     10 parts                          0.125 parts      (THFMA)       (MAA)3G-II 30 parts      60 parts             --     10 parts                          0.250 parts      (THFMA)       (MAA)3H-II 30 parts      60 parts             --     10 parts                          0.5 parts      (THFMA)       (MAA)3I-II 30 parts      60 parts             --     10 parts                          1 part      (THFMA)       (MAA)3J-II 30 parts      55 parts             15 parts                    1 part                          --      (THFMA)             (HPMA) (MAA)__________________________________________________________________________ .sup.1 Stereon 840A IBOMA -- isobornyl methacrylate OMA -- 2ethylhexyl methacrylate ODA -- noctylacrylate/n-decylacrylate mixture HDDA -- 1,6hexanediol diacrylate HDDMA -- 1,6hexanediol dimethacrylate THFMA -- tetrahydrofurfryl methacrylate HPMA -- 2hydroxypropyl methacrylate MAA -- methacrylic acid CHP -- cumene hydroperoxide
1. A curable two-part adhesive composition wherein one-part comprises a polymerizable acrylic monomer and an effective amount of a stabilized organoboron amine complex initiator of the formula: ##STR14## where R, R1 and R2 are alkyl of 1 to 10 carbon atoms or phenyl, R3 and R4 are hydrogen or alkyl of 1 to 10 carbon atoms, or ##STR15## where R5 and R6 are hydrogen or alkyl of 1 to 10 carbon atoms, m is 2 to 10 and n is 1 to 6; and the second part contains an effective destablizing amount of an organic acid activator having the formula:
R--COOOH
where R is H, alkyl or alkenyl of 1 to 8 carbons or aryl of 6 to 14 carbon atoms.
US07692766 1991-04-29 1991-04-29 Acrylic adhesive composition and organoboron initiator system Expired - Lifetime US5106928A (en)
US07692766 US5106928A (en) 1991-04-29 1991-04-29 Acrylic adhesive composition and organoboron initiator system
US07810319 US5143884A (en) 1991-04-29 1991-12-19 Acrylic adhesive composition and organoboron initiator system
CA 2061021 CA2061021C (en) 1991-04-29 1992-02-11 Acrylic adhesive composition and organoboron initiator system
ES92102863T ES2067965T3 (en) 1991-04-29 1992-02-20 Acrylic adhesive composition and organoboron initiator system.
SG1995903985A SG28341G (en) 1991-04-29 1992-02-20 Acrylic adhesive composition and organoboron initiator system
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US07810319 Division US5143884A (en) 1991-04-29 1991-12-19 Acrylic adhesive composition and organoboron initiator system
US5106928A true US5106928A (en) 1992-04-21
ID=24781936
US07692766 Expired - Lifetime US5106928A (en) 1991-04-29 1991-04-29 Acrylic adhesive composition and organoboron initiator system
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CA (1) CA2061021C (en)
DE (2) DE69201093D1 (en)
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Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:SKOULTCHI, MARTIN M.;MERLO, NICHOLAS V.;REEL/FRAME:005690/0614