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Patent US5115008 - Pressure sensitive adhesives - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsThere are provided a pressure-sensitive adhesive and other compositions which free radical cured mixtures of at least one unsaturated elastomeric polymer and at least one organic additive which is substantially nonresponsive to action of free radicals and present in an amount sufficient to modify the...http://www.google.com/patents/US5115008?utm_source=gb-gplus-sharePatent US5115008 - Pressure sensitive adhesivesAdvanced Patent SearchPublication numberUS5115008 APublication typeGrantApplication numberUS 07/566,560Publication dateMay 19, 1992Filing dateAug 9, 1990Priority dateJun 3, 1987Fee statusPaidPublication number07566560, 566560, US 5115008 A, US 5115008A, US-A-5115008, US5115008 A, US5115008AInventorsYukihiko SasakiOriginal AssigneeAvery Dennison CorporationExport CitationBiBTeX, EndNote, RefManPatent Citations (11), Referenced by (21), Classifications (21), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetPressure sensitive adhesives
US 5115008 AAbstract
1. A pressure-sensitive adhesive consisting essentially of a free radical cured mixture containing at least 15 parts by weight of at least one unsaturated elastomeric polymer and at least one tackifying organic additive which is substantially non-responsive to the action of free radicals and selected from the group consisting of saturated aromatic resins, aromatic resins which are at least 50% saturated, saturated aliphatic resins, aliphatic resins in which at least 65% of the unsaturated groups in the resin as formed in saturated or made non responsive to the action of free radicals and saturated oils, said additive present in an amount sufficient to modify the properties of the cured elastomeric polymer, said cured adhesive pressure-sensitive formed in the absence of a non elastomeric cross-linker having a glass transition temperature at least 10� C. below use temperature and an elevated temperature shear higher than the elevated temperature shear prior to cure, said mixture when at a proportion of 40 parts by weight elastomeric polymer and 60 parts by weight organic additive having relative incipient gel dosage of cure of no more than about 1.65 at an electron beam radiation level of 200 kv.
2. A pressure-sensitive adhesive as claimed in claim 1 in which the organic additive is provided to tackify the pressure-sensitive adhesive and the tackifying organic additive is present in a concentration of from about 40 to about 90 per cent by weight based on the total weight of elastomeric polymer and organic additive.
4. A pressure-sensitive adhesive as claimed in claim 1 in which the unsaturated elastomeric polymer is selected form the group consisting of natural rubber, styrene-butadiene block copolymers, styrene-butadiene-styrene block copolymers, styrene-isoprene block copolymers, styrene-isoprene-styrene block copolymers, multiarmed-styrene-isoprene block copolymers, polybutadiene, polyisoprene and mixtures thereof.
5. A pressure-sensitive adhesive as claimed in claim 2 in which the unsaturated elastomeric polymer is selected form the group consisting of natural rubber, styrene-butadiene block copolymers, styrene-butadiene-styrene block copolymers, styrene-isoprene block copolymers, styrene-isoprene-styrene block copolymers, multiarmed-styrene-isoprene block copolymers, polybutadiene, polyisoprene and mixtures thereof.
7. A pressure-sensitive adhesive as claimed in claim 2 in which the organic additive is selected from the group consisting of saturated aliphatic resins, saturated aromatic resins, saturated oils and mixtures thereof.
8. A pressure-sensitive adhesive as claimed in claim 8 in which the organic additive is selected from the group consisting of saturated aliphatic resins, saturated aromatic resins, saturated oils and mixtures thereof.
9. A pressure-sensitive adhesive as claimed in claim 1 in which the unsaturated elastomeric polymer is selected from the group consisting of ABA block copolymers AB block copolymers; multiarmed (AB)x block copolymers and mixtures thereof, wherein A is a block comprising at least one monoalkenyl arene, B is an elastomeric conjugated diene block and x has a value greater than 2.
10. A pressure-sensitive adhesive as claimed in claim 2 in which the unsaturated elastomeric polymer is selected form the group consisting of ABA block copolymers AB block copolymers; multiarmed (AB)x block copolymers and mixtures thereof, wherein A is a block comprising at least one monoalkenyl arene, B is an elastomeric conjugated diene block and x has a value greater than 2.
12. A pressure-sensitive adhesive consisting essentially of a free radical cured mixture comprising from about 15 to about 60 parts by weight of an unsaturated styrene-isoprene-styrene block copolymer and from about 85 to about 40 parts by weight tackifying organic additive which is substantially non-responsive to the action of free radicals and selected from the group consisting of saturated aromatic resins, aromatic resins which are at least 50% saturated, saturated aliphatic resins, aliphatic resins in which at least 65% of the unsaturated groups of the resin are saturated, saturated oils and mixtures thereof, said pressure-sensitive adhesive formed in the absence of a non elastomeric cross-linker having a higher elevated temperature shear as compared to the mixture prior to cure and a glass transition temperature at least 10� C. below use temperature, said mixture in a proportion of 40 parts by weight copolymer and 60 parts by weight organic additive has the relative incipient gel dosage of cure about no more than 1.65 at an electron beam radiation level of 200 kv.
13. A pressure-sensitive adhesive as claimed in claim 12 in which is present prior to cure an end block reinforcing agent which is compatible with the styrene blocks.
14. A pressure-sensitive adhesive consisting essentially of a free radical cured mixture comprising, based on the weight of the mixture, from 15 to about 60 parts by weight of a multiarmed styrene-isoprene block copolymer ad from about 40 to about 85 parts by weight of a tackifying organic additive which is substantially non-responsive to the action of free radicals and selected form the group consisting of saturated aromatic resins, saturated aliphatic resins aromatic resins which are at least 50% saturated aliphatic resins in which at least 65% of the saturated group of the resin as formed are saturated and mixtures thereof, and pressure-sensitive adhesive formed in the absence of a non elastomeric cross-linker having a high elevated temperature shear as compared to the mixture prior to cure and a glass transition temperature of at least 10� C. below use temperature and said mixture in a proportion of 40% parts by weight copolymer and 60 parts by weight organic additive has a relative incipient gel dosage of cure about no more than 1.65 at an electron beam radiation level of 200 kv.
15. A pressure-sensitive adhesive as claimed in claim 14 in which is present prior to cure an end block reinforcing agent which is compatible with the styrene blocks.
16. A pressure-sensitive adhesive consisting essentially of a free radical cured mixture comprising, based on the weight of the mixture, from 15 to about 60 percent by weight of a styrene-butadiene-styrene block copolymer and form about 40 to about 85 parts by weight of a tackifying organic additive which is substantially non-responsive to the action of free radicals selected from the group consisting of aromatic resins, aromatic resins which are at least 50% saturated and mixtures thereof with saturated aliphatic resins in which at least 65% of the unsaturated group of the resins are saturated, saturated aliphatic resins and saturated oils, said pressure-sensitive adhesive being formed in the absence of a non elastomeric cross-linker and having a high elevated temperature shear as compared to the mixture prior to cure and a glass transition temperature of at least 10� C. below use temperature, said mixture in a proportion of 40 parts by weight copolymer and 60 parts by weight organic additive has no relative incipient gel dosage of cure about no more than 1.65 at an electron beam level of 200 kv.
17. A pressure-sensitive adhesive as claimed in claim 16 in which is present prior to cure an end block reinforcing agent which is compatible with the styrene blocks.
This is a continuation of application Ser. No. 07/057,504 filed Jun. 3, 1987.
According to the present invention, there are provided pressure-sensitive adhesive compositions which comprise in combination at least one unsaturated elastomeric polymer capable of undergoing gel forming reactions in the presence of free radicals preferably generated by actinic radiation or electron beam radiation, and at least one organic additive which is substantially nonresponsive to free radicals and which is at least dispersable and preferably soluble in the elastomeric polymer. The elastomeric polymer preferably has a glass transition temperature of from about -20� to about -100� C. The organic additive affects a property of the pressure-sensitive adhesive composition, such as tack or other properties. The improvement resides in the use of a organic additive which is substantially nonresponsive to the action of free radicals, as defined herein, while providing, upon cure, a pressure-sensitive adhesive composition having a glass transition temperature of at least 10� C., preferably at least 20� C. below use temperature.
After cure, with the increase of gel content, the combination exhibits a positive change in properties such as elevated temperature shear. This occurs at substantially lower levels of free radical generation that would have been required were the organic additive to consume a significant amount of free radicals.
FIG. 5 compares the relative incipient gel dosage as function of tackifier concentration for Excorez� 1310, Foral� 85 and Regalrez� 1033.
The present invention is directed to reducing the energy requirements of free radical cross-linking of unsaturated elastomeric polymers which are part of multi-component compositions such as pressure-sensitive adhesives in which unsaturated elastomeric polymers are tackified or otherwise modified as to physical properties by addition of at least one organic additive.
For electron beam radiation, incipient gel dosage is determined as a minimum amount of electron beam (EB) dosage in kiloGray required to form a toluene insoluble gel. Insoluble gel is measured by placing 200 milligrams of a directly irradiated sample into 10 grams of toluene checking for the presence of insoluble material after 24 hours standing. Radiation is increased (or decreased) in increments of 10 kGy. If the solution appears clear upon visual inspection it is filtered through qualitative filter paper to check for the presence of gel. The procedure is repeated for each 10 kGy dosage level increment and the dosage at which gelation occurs is interpolated from the data. If a gel was not observed, for example, at 60 kGy, but was at 70 kGy, the value of incipient gel dosage is reported as 65 kGy. In each instance, the sample is coated from a toluene solution onto a release paper (50-75g/m2) and dried in an oven. The sample surface was directly exposed to EB radiation at 200 KV with inerting to 400 ppm O2 or less. For values reported herein, the EB unit used was manufactured by Energy Sciences.
More preferably, the elastomeric copolymers are formed of styrene-butadiene-styrene block copolymers and/or styrene-isoprene-styrene block, multiarmed styreneisoprene block copolymers, polybutadiene and polyisoprene. Mixtures of elastomers may be employed.
As examples of organic additives which are substantially nonresponsive to free radicals there may be mentioned hydrogenated organic compounds, such as hydrogenated aromatic resins including hydrogenated polystyrene, polyalpha-methyl styrene, polyvinyl toluene, copolymers of styrene with other monomers and the like; hydrogenated aliphatic resins derived from petroleum based products; highly hydrogenated rosins and rosin esters: hydrogenated white oil, mineral oil and the like. As specific tackifiers employed in the practice of the invention there may be mentioned hydrogenated styrene based resins such as Regalrez� resins designated as 1018, 1033, 1065, 1078, 1094 and 1126 manufactured and sold by Hercules, Inc.; Regalrez� 6108 a 60% hydrogenated aromatic resin, also manufactured by Hercules; hydrogenated C5 and/or C9 hydrocarbon feed stocks such as Arkon� P-70, P-90, P-100, P-125, P115, M-90, M-100, M-110 and M-120 resins manufactured and sold by Arakawa Chemical and Regalite� R-100, MGB-63, MGB-67, MGB-70, resins manufactured and sold by Hercules, Inc.; hydrogenated Polycyclo-pentadienes such as Escorez� 5320, 5300 and 5380 resins manufactured and sold by Exxon Chemical, hydrogenated polyterpene and other naturally occurring resins such as Clearon� P-105, P-115, P-125, M-105, M-115 manufactured and sold by Yasuhara Yushi Kogyo Co. Ltd. of Japan and Eastotack� H-100, H-115 and H-130 resins manufactured and sold by Eastman chemical and the like; Kaydol� hydrogenated mineral oil manufactured and sold by Witco Chemical and the like.
Base unsaturated elastomeric polymers used were a mixture of linear styrene-isoprene-styrene (SIS) and styrene-isoprene (SI) block copolymers known as Kraton� D-1107 and D-1111; styrene-butadiene-styrene (SBS) block copolymers known as Kraton� D-1101 and D-1102 and DX-1300 and multi-armed (SI)x block copolymer known as Kraton� D-1320X1 all manufactured and sold by Shell Chemical Company and styrene-butadiene block copolymer known as Solprene� 1205 manufactured and sold by Housemex, Inc. As representative cf an unsatisfactory tackifying unsaturated alphatic resin there was used Escorez� 1310, a petroleum based hydrocarbon resin manufactured and sold by Exxon Chemical Company, and Piccolite� A-115, an alpha-pinene resin manufactured and sold by Hercules, Inc. Foral-85, a well known hydrogenated rosin ester manufactured and sold by Hercules, Inc. may be functional or nonfunctional as an organic additive depending on the elastomer(s) it is combined with. The organic additives which are used to illustrate the instant invention are of the Escorez� 5000 series. Also used to illustrate the practice of the invention are Regalrez� 6108, 1078 and 1000 series of resins. Kaydol� mineral oil was as a representation of hydrogenated oil. The invention is primarily illustrated in respect of effect of unsaturation of the organic compound, namely, a tackifier, on incipient or relative incipient gel dosage (the incipient gel dosage cf a mixture divided by the incipient gel dosage of the elastomer) required to initiate gel formation versus resin concentration in percent by weight. Incipient gel dosage is measured as defined above. To establish product properties, the formulation was coated from toluene onto a release paper (50g/m2), dried in an oven and laminated to a 50 micron thick polyester film. EB radiation was through the polyester film. 180� Peel in Newtons per Meter (N/M) were determined using PSTC-1 at 20 minute dwell. Loop tack was measured by forming a loop from a 1 inch by 8 inch strip, adhesive face out, inserted in the jaws of an Instron tester and moving the loop at the rate of 12 inches per minute onto a stainless steel panel, then removing the strip at the rate of 12 inches per minute as soon as one square inch of contact is made. The highest force required to remove the loop is reported in N/M. Shear reported in Kiloseconds (K. S.) was for 0.5�0.5 inch overlap on a stainless steel panel at a 500 gram force load. Also known as TRW-6-1523 and DX-XL.
The study was performed to establish the effect of using conventional tackifying resins to tackify elastomers on the electron beam (EB) dosage required to achieve incipient gel formation as a function of tackifier (resin) content. There was employed SIS elastomeric polymers known as Kraton� D-1107 (Control 1), SBS block copolymers Kraton� D-1101 (Control 2) and DX 1300 (Control 3) and Kraton� D-1320X, a multi-armed styrene-isoprene block copolymers (Control 4).
The study established, first of all, the base level of EB dosage necessary to achieve a cohesive strength improvement as evidenced by gel formation in the base elastomer, more particularly, where at least 10% of the elastomer of adhesive composition formed an insoluble gel. FIG. 1 shows that incipient gel dosage increases dramatically as the elastomer is diluted with conventional tackifiers. Since conventional elastomer based pressure-sensitive adhesives contain about 40-90% by weight added tackifying resins, this means that the typical adhesive formulations required an EB dosage of 2-5 times higher than the dosage required for the elastomer itself to achieve an incipient gel formation when an unsaturated C-5 hydrocarbon Escorez� 1310, (Controls 1 and 4) and Piccolite A-115 alpha-pinene (Controls 2 and 3) tackifiers are used as the tackifying resins. The elastomer requiring the lowest dosage was the multiarmed (SI)x copolymer.
FIG. 2 shows the relative EB dosage level required to achieve incipient gel formation for the compositions based on Kraton� D-1107. To illustrate the invention there Was used Regalrez� 1033 an 100% hydrogenated (saturated) aromatic resin manufactured by Hercules, Inc. (Example and Escorez� E-5380, a saturated aliphatic hydrocarbon manufactured by Exxon (Example 2). The comparison was Control 1. As can be seen incipient dosage to gel increased in proportion to the amount of unsaturated tackifying resin introduced to the rubber whereas the use of the hydrogenated tackifiers causes the incipient dosage to remain the same or in some instances reduced.
Using the same procedure as the previous Examples and Controls, FIG. 3 shows the effects of a saturated tackifier , Escorez� 5380, (Example 3) and an unsaturated tackifier, Escorez� 1310 (Control 5) have on the relative incipient gel dosage required to achieve gel formation for a multi-armed styrene-isoprene block copolymer (Kraton� -D-1320X).
CONTROL 6 AND 7 EXAMPLES 4 to 7
Table 1 tabulates the improved high temperature properties induced to Kraton� D-1107 and Kraton� D-1320X using as the saturated tackifier Regalrez� 1078. While 180� peel remain essentially unchanged there is dramatic improvement in elevated temperature shear.
TABLE 1__________________________________________________________________________Component Parts        Cont 6             Ex 4 Ex 5 Cont 7                            Ex 6 Ex 7__________________________________________________________________________Kraton � D-1107        35   35   35   --   --   --Kraton � D-1320X        --   --   --   35   35   35Regalrez � 1078        65   65   65   65   65   65Antioxidant  1    1    1    1    1    1EB Dosage, kGy        0    75   100  0    75   100180� Peel at 23� C., (N/M)        1490 1770 1460 1690 1220 1320180� Peel at 70� C., (N/M)        350  440  310  320  390  320Looptack, (N/M)        1490 2300 2350 1690 1220 1320Shear at 70� C., (K.S.)        1.1  4.4  7.2  0.15 7    17.8__________________________________________________________________________
FIG. 4 shows the relative incipient gel formation dosage for Kraton� D-1107 using an aromatic tackifier of different levels of unsaturation. They are manufactured and sold by Hercules, Inc., under the designation Piccolastic� A-50 (0% hydrogenated), Regalrez� 3102 (30% hydrogenated); Regalrez� 6108 (60% hydrogenated) and Regalrez� 1033 (100% hydrogenated). As shown in FIG. 4, the higher the degree of hydrogenation the lower the dosage required, for a given level of resin concentration, to form a gel. This is important since a certain amount, usually 30-40% of the base rubber, must be crosslinked to form a network in order to achieve a significant improvement in physical properties.
CONTROLS 1 AND 9 AND EXAMPLES 6
Endex� 160 is an aromatic end-block reinforcing resin compatible with the polystyrene phase of the block copolymer Kraton D-1107 but not compatible with the elastomeric polyisoprene phase. It does not substantially interfere with crosslinking in presence of an organic additive (Table 2) or a blend thereof (Table 3) but synergistically provided exceptionally high elevated temperature shear strength on EB cure.
TABLE 4______________________________________Formula Elastomer  Escorez � 5300                           Regalrez � 1065______________________________________1       30         11.7         58.32       30         30.9         39.13       40         44.2         15.8______________________________________
TABLE 2__________________________________________________________________________      Cont 10           Ex 10                Cont 11                     Ex 11                          Cont 12                               Ex 12__________________________________________________________________________Kraton D-1107, parts      40   40   40   40   40   40Regalrez 1078, parts      60   60   60   60   60   60Endex 160, parts      --   --   10   10   15   15Antioxidant, parts      1    1    1    1    1    1EB dosage (kGy)      0    75   0    75   0    75180� Peel, (N/M)      1110 1160 1350 1220 1190 1000Looptack, (N/M)      1890 1880 2250 1860 1890 154070� C. Shear (K.S.)      0.1  3.2  3.2  50.1 6.7  81.7__________________________________________________________________________
TABLE 3__________________________________________________________________________      Cont 13           Ex 13                Cont 14                     Ex 14                          Cont 15                               Ex 15__________________________________________________________________________Kraton D-1107, parts      40   40   40   40   40   40Regalrez 1078, parts      40   40   40   40   40   40Escorez 5320, parts      20   20   20   20   20   20Endex 160, parts       0   0    10   10   15   15Antioxidant, parts       1   1     1    1   1    1EB dosage (kGy)       0   75   0    75   0    75180� Peel, (N/M)      1340 1300 1340 1430 1360 1260Looptack, (N/M)      2170 2140 1570 1710 1540 77070� C. Shear, (K.S.)       6   60.3 69.1 807  51.4 854__________________________________________________________________________
TABLE 5__________________________________________________________________________Cont/ExFORMULA       EB DOSE (kGy)                LOOPTACK                       180� PEEL, RT                               180� PEEL, 70� C.                                         ETS, 70� C.__________________________________________________________________________Cont. 161       0       2550   1670    140       0.2Ex. 161      75       2410   1620    190       9.9Cont. 172       0       2570   1600     65       0.1Ex. 172      75       1260   1520    265       25.2Cont. 182       0       1950   1350    245       3.0Ex. 183      75       1220   1240    280       218.2__________________________________________________________________________
Table 6 establishes that other saturated compounds, namely brominated hydrocarbon fire retardants, can be successfully added to Kraton� 1107 and reduce incipient gel dosage.
Control 20 and Examples 26-29 are for the combination of an SBS copolymer Kraton� D-1102 tackified with a mixture of Regalrez� 6108 and Kadol Oil a hydrogenated mineral oil in the presence of trimethylolpropane tri(3-mercaptopropionate) as a multifunctional polythiol crossliner. As can be seen in Table 7, the combination gives on cure excellent elevated temperature shear.
TABLE 6__________________________________________________________________________Cont/ExKraton � D-1107          BCL-462               HBCDD                    BE-51                        PYROCHEK                               INCIPIENT GEL (kGy)__________________________________________________________________________Cont. 19       --   --   --  --     85Ex. 2098        2    --   --  --     55Ex. 2195.2      4.8  --   --  --     55Ex. 2287        13   --   --  --     55Ex. 2395.2      --   4.8  --  --     65Ex. 2495.2      --   --   4.8 --     55Ex. 2595.2      --   --   --  4.8    65__________________________________________________________________________ Staytex � BCL-462 = 1,2dibromoethyl-3,4-dibromocyclohexane (Ethyl Corp.) HBCDD = hexabromocyclodecane (Great Lakes Chemical) BE-51 = tetrabromobis-phenol-A, bis(allyl ether) (Great Lakes Chemical) Pyrocheck � 68DB = poly(tribromostyrene) (Ferro Corp.)
TABLE 7__________________________________________________________________________      Cont 15           Ex 26                Ex 27                     Ex 28                          Ex 29__________________________________________________________________________Kraton D-1102      40   40   40   40   40Regalrez 6108      50   50   50   50   50Kaydol Oil 10   10   10   10   10TMPTMP*     0   0.6  0.6  1    1Antioxidant       1   1    1    1    1EB dosage (kGy)       0   20   50   20   50180� Peel, (N/M)      1390 1180 1120 1130 1060Looptack, (N/M)      1750 1352 1770 1850 111070� C. Shear (K.S.)**       1   2.3  120+***                     11.8 120+***__________________________________________________________________________ *TMPTMP is trimethylolpropane tri(3mcercaptopropionate) **Weight is 1000 g and overlap area is 1 sq. in. ***No failure
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