WO1985000376A1 - Pressure-sensitive adhesive composition - Google Patents
Pressure-sensitive adhesive composition Download PDFInfo
- Publication number
- WO1985000376A1 WO1985000376A1 PCT/JP1984/000350 JP8400350W WO8500376A1 WO 1985000376 A1 WO1985000376 A1 WO 1985000376A1 JP 8400350 W JP8400350 W JP 8400350W WO 8500376 A1 WO8500376 A1 WO 8500376A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin
- plasticizer
- composition according
- sensitive adhesive
- tackifier resin
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title abstract description 3
- 229920005989 resin Polymers 0.000 claims abstract description 77
- 239000011347 resin Substances 0.000 claims abstract description 77
- 239000004014 plasticizer Substances 0.000 claims abstract description 30
- 229920001971 elastomer Polymers 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 239000000853 adhesive Substances 0.000 claims description 37
- 230000001070 adhesive effect Effects 0.000 claims description 37
- 239000004793 Polystyrene Substances 0.000 claims description 9
- 229920002223 polystyrene Polymers 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 238000003958 fumigation Methods 0.000 claims 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 16
- 238000007323 disproportionation reaction Methods 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000012943 hotmelt Substances 0.000 description 9
- 238000013508 migration Methods 0.000 description 9
- 230000005012 migration Effects 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000000087 stabilizing effect Effects 0.000 description 5
- -1 styrene-7-t-jen j Polymers 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KKEBXNMGHUCPEZ-UHFFFAOYSA-N 4-phenyl-1-(2-sulfanylethyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCS)CC1C1=CC=CC=C1 KKEBXNMGHUCPEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 240000002989 Euphorbia neriifolia Species 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- 229920002633 Kraton (polymer) Polymers 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical class [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- XIKYYQJBTPYKSG-UHFFFAOYSA-N nickel Chemical compound [Ni].[Ni] XIKYYQJBTPYKSG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J153/02—Vinyl aromatic monomers and conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
Definitions
- the present invention relates to a novel sensitive adhesive composition. Further,
- hot-melt or solvent-based pressure-sensitive adhesives containing a specific stabilized b-based resin as a tackifying resin The present invention relates to an agent composition.
- Hot-melt type and other resource-saving sensitive adhesives such as 5 are generally composed mainly of 10 ⁇ box: rubber, tackifying resin and plasticizer (mainly oil). It is composed by mixing at a weight ratio of 0 ⁇ 70 to ⁇ 50 ⁇ 200.
- solvent-type E-sensitive adhesives based on natural rubber and other materials, they are more resistant to cold (such as when preparing and painting low-temperature tack powders).
- plasticizer component is usually blended at the above ratio with respect to 7 locks of jisum.
- the amount is increased up to 0100% by weight, the cold resistance is improved.
- the adhesiveness is reduced in the packaging table, and the plasticizer is applied to the label surface in the case of labeling.
- the present inventors have also aimed at solving the above-mentioned drawbacks found in the hot-melt type or the solitary type sensitive adhesives, and especially the adhesives.
- Investigations were made on the tackifying resin used in the field.
- the tackifying resin generally used for the sensitive adhesive (1) the three properties of tackiness (tack, adhesive strength and cohesive strength) under normal conditions are good.
- the migration of the plasticizer is required (good packaging properties for packaging and good penetration into the base material for labels).
- Good aging resistance and good thermal stability are required to be satisfied. (4) Performance requirements must be satisfied.
- tackifier resins examples include terpene resins, aliphatic petroleum resins, hydrogenated petroleum resins, and disproportionated ⁇ 5 ester.
- terpene resins examples include terpene resins, aliphatic petroleum resins, hydrogenated petroleum resins, and disproportionated ⁇ 5 ester.
- aliphatic petroleum resins the softening point of which is usually around 100 ° C
- the migration of the plasticizer was i9, and the step-hole property was inferior.], And permeation into the lapel was observed.
- terpene resin normally its softening point is around 1.5 ° C
- hydrogenated petroleum resin softening point of about 125 ° C
- flamenco resin Performance was evaluated for resins with a high softening point such as tel (softening point about 12 ° C).
- tel softening point about 12 ° C
- the transfer of the plasticizer was observed, which was not preferable, and a correlation could not be found between the softening point of the resin used and the above-mentioned problems such as the transfer of the plasticizer. .
- the polarity of the resin is high, so it was expected that the disadvantage of the migration of the plasticizer could be solved.
- the present invention relates to a sensitive adhesive composition containing 7 lock rubber, a tackifier resin and a plasticizer as a main component, wherein the tackifier resin is partially foamed. And Z or part 5 minutes Maleized disproportionation lone ester (hereinafter referred to as
- stabilized resin 5 series resin (Hereinafter simply referred to as “stabilized resin 5 series resin”)).
- the paste be used in terms of its coatability and melt viscosity.
- the 7 lockrooms to be used are:
- a typical example is Rust polymer ⁇ A block composed of 7 blocks of conjugated and elastomeric conjugated polymers. More specifically, for example, a polymer Polystyrene / Polystyrene Lock copolymer, Polystyrene / Polystyrene 2 / — Polystyrene 7 lock Copolymers and the like can be mentioned. Examples of commercially available products include “ ⁇ 1102”, “KRATON 1107”, and “KHATON 4141” manufactured by Jell Chemical Co., Ltd.
- the lock used for the adhesive is as follows:
- natural rubber, styrene or other rubber may be used in combination, but the ratio of the combination is determined by the viscosity and non-volatile content of the resulting photosensitive adhesive. It is the maximum amount that can be replaced by 30% by weight instead of 7 locks.
- the resin must be a partially fumarated and Z or partially maleized disproportionated polyester.
- a resin can be produced according to a known method. As an example of the method, a partial maleization port ⁇ and Z or a partial maleization b ⁇ and an alcohol
- the partially-malinated and partially-malinated rosins used here can be produced by a known method without any particular limitation. For example, add fumaric acid or maleic anhydride to the raw material and heat it.] ?, T-iswa) to obtain a ⁇ — type adduct be able to.
- any one of gamulone, woodlone and trol oil may be used as raw material lon.
- a trivalent or higher-valent alcohol is preferred.
- the polyvalent alloy include, for example, ⁇ re-t, t-re-selin, pen-e-trile, and ⁇ pet-e-trile And particularly,
- the above esterification reaction can be carried out in the same manner as a usual esterification reaction method. That is, for example, one step can be carried out by ripening and dehydrating both components in the presence or absence of a catalyst or in the presence or absence of a solvent.
- a solvent used here is: Aromatic solvents such as z1 / 1 / toluene, medium and the like can be used.
- the catalyst include acid catalysts such as sulfuric acid, acetic acid and paratoluene j sulfonic acid, hydroxides of alkaline earth metals such as calcium hydroxide, and oxide oxides. Metal oxides, charcoal oxide, charcoal
- Usual esterification catalysts such as calcium acid, magnesium acetate, and calcium acetate can be used.
- the charging ratio of both components is not particularly limited, and the types of partially-malonated and partially-malinated borons, their acid values, and the softening points of the resulting esterified products are determined. It is determined as appropriate in consideration of
- the disproportionation reaction of the obtained esterified product can be carried out according to various known methods.
- the above esterified product may be heated to about 220 to 300 ° C. in the presence of a usual disproportionation catalyst.
- the disproportionation catalyst to be used include noble metals such as palladium, nickel, and platinum, iodine, and iron iodide, such as iodide, sulfur dioxide, and iron sulfide. Which sulfur compounds are mentioned.
- a stabilized resin used in the present invention is obtained.
- the use of the stabilized resin is an essential requirement, and the intended effects of the present invention can be obtained only by using the stabilized resin.
- the resin is given a suitable polarity by disproportionation, thereby improving the retention of plasticizer and the solubility of the resin with j-m.
- hydrogenation may be considered as a means for stabilizing the above-mentioned I sdelide in addition to the above-mentioned disproportionation, but the resin obtained by such hydrogenation is referred to as a tackifying resin. Even if it is used, it is difficult to sufficiently suppress the migration of the plasticizer, and the intended effects of the present invention cannot be achieved.
- the hydrogenation reaction itself is disadvantageous in comparison with the disproportionation reaction in terms of economy, ease of reaction, and the like.
- the stabilizing resin used in the present invention can be similarly manufactured by other methods shown below. That is, a method of dissolving or disproportionating a melamine or methionone as a starting material for ffi, and disproportionating it first, followed by esterification. In addition, a method of simultaneously performing and esterification can also obtain a stabilized mouth-based resin.
- the reaction conditions and the like in each of these methods are not particularly different from known methods, and more specifically, they can conform to the methods described above.
- the stabilized lone-based resin obtained as described above usually has a softening point of 110 to 140 ° C., preferably 115 to 135 °, and a molecular weight of about 100. 0 to 1800, preferably about 100 to 1500], and having an acid value of about 20 or less], as the tackifying resin of the present invention. It can be used particularly preferably.
- the sensitive adhesive composition of the present invention comprises the above-mentioned stabilizing resin as a tackifier resin, and a lock, a rubber and a plasticizer as main components.
- the content of the tackifier resin and the plasticizer be in the range of 100 to 100 parts by weight, and the compatibility and the compatibility be excellent, respectively. It is a useful sensitive adhesive that has aging resistance, heat stability and adhesiveness, and is also economical.
- compositions of the present invention depending on the necessity, within brewing I Sonru the desired effect of the present invention, 0 O viewpoint of economy, aliphatic petroleum resin (C 5 series), Lighten aliphatic-aromatic petroleum resin (c-zc.) And other products
- hydrogenated petroleum resin can be added and blended.
- the thus-obtained sensitive adhesive composition of the present invention is mixed with a noon roll according to a conventional method,
- the practical means of wearing a j-room can be the same as that of this ordinary f-room.
- a plastic film such as phantom, paper, and polyester can be used as the base material.
- Example 7 Each of the above samples (combinations obtained from Example 7 and Comparative Examples 1 to 6 to C) was subjected to hot melt filtration using a polish drill filter. It was applied to a thickness of 30 cm on a room to make an adhesive tailor for testing. Using the table, measurements were made in accordance with the following various performance test methods to evaluate the sealability and the permeability of the plasticizer into the label.
- Step pole seal Attach the above test adhesive table on the surface of the l-inch / l-inch surface and apply 3 loads at room temperature, and wait for the time until the bonded part peels off. Measure.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE8484902729T DE3477017D1 (en) | 1983-07-13 | 1984-07-09 | Pressure-sensitive adhesive composition |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58128159A JPS6020977A (ja) | 1983-07-13 | 1983-07-13 | 感圧性接着剤組成物 |
| JP58/128159 | 1983-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1985000376A1 true WO1985000376A1 (en) | 1985-01-31 |
Family
ID=14977841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1984/000350 WO1985000376A1 (en) | 1983-07-13 | 1984-07-09 | Pressure-sensitive adhesive composition |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4622357A (forum.php) |
| EP (1) | EP0150218B1 (forum.php) |
| JP (1) | JPS6020977A (forum.php) |
| DE (1) | DE3477017D1 (forum.php) |
| WO (1) | WO1985000376A1 (forum.php) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987002369A1 (en) * | 1985-10-11 | 1987-04-23 | Asahi Kasei Kogyo Kabushiki Kaisha | Terminal-modified block copolymer and composition containing said copolymer |
| DE3686860D1 (de) * | 1985-10-25 | 1992-11-05 | Cray Valley Sa | Zusammensetzungen fuer heissschmelzklebstoffe, verfahren zu deren herstellung und deren anwendung in einem klebeverfahren. |
| FR2612933A1 (fr) * | 1986-06-10 | 1988-09-30 | Charbonnages Ste Chimique | Compositions pour adhesifs thermofusibles et leur procede de preparation |
| JPH0813957B2 (ja) * | 1987-05-07 | 1996-02-14 | 荒川化学工業株式会社 | 水性粘着剤組成物 |
| US5627229A (en) * | 1992-07-25 | 1997-05-06 | H.B. Fuller Licensing & Financing, Inc. | Hot melt adhesive having controlled property change |
| US5853864A (en) * | 1988-06-30 | 1998-12-29 | H. B. Fuller Licensing & Financing Inc. | Composite article resistant to moisture-induced debonding |
| US5039726A (en) * | 1989-09-25 | 1991-08-13 | The Goodyear Tire & Rubber Company | Alkyl (C12-C22) esters of rosin acid |
| US5260126A (en) * | 1990-01-10 | 1993-11-09 | Kimberly-Clark Corporation | Low stress relaxation elastomeric nonwoven webs and fibers |
| US5242980A (en) * | 1990-02-06 | 1993-09-07 | Exxon Chemical Patents Inc. | Ethylene-unsaturated alcohol or acid copolymer and epoxy crosslinker |
| US5095046A (en) * | 1990-02-06 | 1992-03-10 | Exxon Chemical Patents Inc. | Hot melt adhesive of ethylene/unsaturated acid copolymer and epoxy crosslinker |
| US5093463A (en) * | 1991-01-14 | 1992-03-03 | Westvaco Corporation | Maleinized rosin containing solvent-borne alkyd resin compositions |
| US5166245A (en) * | 1991-04-08 | 1992-11-24 | Westvaco Corporation | Modified rosin resins for water-based inks |
| US5120781A (en) * | 1991-05-07 | 1992-06-09 | Union Camp Corporation | Acid-modified polyhydric alcohol rosin ester tackifiers and hot melt adhesive compositions containing those tackifiers |
| EP0603384B1 (en) * | 1992-07-02 | 2002-10-16 | H.B. FULLER LICENSING & FINANCING, INC. | Hot melt adhesive composition |
| USH1402H (en) * | 1992-09-24 | 1995-01-03 | Shell Oil Company | Styrene-isoprene-styrene block copolymer composition and adhesives made therefrom |
| DE69314913T2 (de) * | 1992-11-25 | 1998-04-02 | Loctite Corp | Adhäsionsverbessererzusammensetzungen |
| US5412032A (en) * | 1994-02-22 | 1995-05-02 | Shell Oil Company | High molecular weight low coupled linear styrene-isoprene-styrene block copolymer composition and adhesives made therefrom |
| WO2001026700A1 (en) * | 1999-10-14 | 2001-04-19 | Avery Dennison Corporation | Hot melt pressure sensitive adhesives |
| US6739816B1 (en) * | 2000-11-24 | 2004-05-25 | Hewlett-Packard Development Company, L.P. | Systems and methods of attaching a cover to a text body |
| US6818692B2 (en) | 2001-09-04 | 2004-11-16 | W. W. Henry Company | High strength non hazardous air pollutant rubber cement composition |
| US7285583B2 (en) * | 2002-07-30 | 2007-10-23 | Liquamelt Licensing Llc | Hybrid plastisol/hot melt compositions |
| JP2006249317A (ja) * | 2005-03-11 | 2006-09-21 | Chuo Rika Kogyo Corp | 変性粘着付与剤及びこれを用いた接着剤組成物 |
| FR2912153B1 (fr) | 2007-02-02 | 2009-04-17 | Bostik S A Sa | Composition adhesive pour etiquette auto-adhesive decollable |
| FR2918069B1 (fr) * | 2007-06-29 | 2009-09-04 | Bostik S A Sa | Hmpsa pour etiquette auto-adhesive decollable |
| DE202007012747U1 (de) | 2007-09-12 | 2008-11-27 | Gissler & Pass Gmbh | Teilungseinsatz zur Aufteilung einer Verpackungsbox sowie Verpackungsbox hierfür |
| US20110213120A1 (en) * | 2010-03-01 | 2011-09-01 | Arizona Chemical Company | Rosin esters for non-woven applications, methods of making and using and products therefrom |
| JP6996077B2 (ja) * | 2015-12-28 | 2022-01-17 | 荒川化学工業株式会社 | 粘着付与樹脂、粘・接着剤、ホットメルト接着剤 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3211683A (en) * | 1959-12-15 | 1965-10-12 | Arakawa Rinsan Kagaku Kogyo | Sizing emulsions comprising a petroleum resin-maleic anhydride addition product and rosin |
| US3239478A (en) * | 1963-06-26 | 1966-03-08 | Shell Oil Co | Block copolymer adhesive compositions and articles prepared therefrom |
| US3427269A (en) * | 1966-03-14 | 1969-02-11 | Shell Oil Co | Adhesive compositions comprising certain block copolymers and selected resins |
| GB1177675A (en) * | 1966-04-13 | 1970-01-14 | Morgan Adhesives Co | Pressure Sensitive Adhesive Composition. |
| US3736281A (en) * | 1968-06-25 | 1973-05-29 | Flintkote Co | Method of making pressure-sensitive hot-melt adhesives |
| US3686107A (en) * | 1968-06-25 | 1972-08-22 | Flintkote Co | Pressure-sensitive hot-melt adhesives |
| US3632540A (en) * | 1968-06-26 | 1972-01-04 | Petrolite Corp | Block polymer-wax blends |
| US3658740A (en) * | 1969-12-05 | 1972-04-25 | Phillips Petroleum Co | Pressure sensitive adhesives |
| US3950291A (en) * | 1974-06-03 | 1976-04-13 | Phillips Petroleum Company | Hot-melt adhesive composition |
| JPS559605A (en) * | 1978-06-23 | 1980-01-23 | Arakawa Chem Ind Co Ltd | Preparation of rosin ester having high softening point and improved stability |
| JPS5950191B2 (ja) * | 1978-11-14 | 1984-12-06 | 三井化学株式会社 | ホツトメルト型粘着剤組成物 |
| US4325770A (en) * | 1980-06-27 | 1982-04-20 | Permacel | Process for pressure-sensitive adhesive coated products |
-
1983
- 1983-07-13 JP JP58128159A patent/JPS6020977A/ja active Granted
-
1984
- 1984-07-09 US US06/713,395 patent/US4622357A/en not_active Expired - Lifetime
- 1984-07-09 WO PCT/JP1984/000350 patent/WO1985000376A1/ja active IP Right Grant
- 1984-07-09 DE DE8484902729T patent/DE3477017D1/de not_active Expired
- 1984-07-09 EP EP84902729A patent/EP0150218B1/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| Japanese Patent Publication No. 17037/1969 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6020977A (ja) | 1985-02-02 |
| DE3477017D1 (en) | 1989-04-13 |
| JPH0340755B2 (forum.php) | 1991-06-19 |
| EP0150218A1 (en) | 1985-08-07 |
| EP0150218A4 (en) | 1986-01-28 |
| EP0150218B1 (en) | 1989-03-08 |
| US4622357A (en) | 1986-11-11 |
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