WO2015080269A1 - Résine polyoléfinique modifiée - Google Patents
Résine polyoléfinique modifiée Download PDFInfo
- Publication number
- WO2015080269A1 WO2015080269A1 PCT/JP2014/081639 JP2014081639W WO2015080269A1 WO 2015080269 A1 WO2015080269 A1 WO 2015080269A1 JP 2014081639 W JP2014081639 W JP 2014081639W WO 2015080269 A1 WO2015080269 A1 WO 2015080269A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyolefin resin
- weight
- modified polyolefin
- component
- graft
- Prior art date
Links
- 229920005672 polyolefin resin Polymers 0.000 title claims abstract description 117
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000002844 melting Methods 0.000 claims abstract description 13
- 230000008018 melting Effects 0.000 claims abstract description 13
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 29
- 239000000853 adhesive Substances 0.000 claims description 26
- 230000001070 adhesive effect Effects 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 11
- 238000000113 differential scanning calorimetry Methods 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 23
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 16
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 15
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 12
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- 238000006243 chemical reaction Methods 0.000 description 12
- -1 polypropylene Polymers 0.000 description 12
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 11
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- 230000000052 comparative effect Effects 0.000 description 9
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
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- 239000004925 Acrylic resin Substances 0.000 description 2
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- 230000002411 adverse Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- 239000003990 capacitor Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
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- 238000011156 evaluation Methods 0.000 description 2
- 238000010559 graft polymerization reaction Methods 0.000 description 2
- 239000005001 laminate film Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
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- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
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- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/085—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyolefins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/002—Priming paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/06—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
Definitions
- the present invention relates to a modified polyolefin resin.
- polyolefin resins such as polypropylene resins and polyethylene resins are inexpensive and have many excellent properties such as moldability, chemical resistance, water resistance, and electrical properties. Widely adopted.
- a polyolefin resin base material such as a polyurethane resin, a polyamide resin, an acrylic resin, or a polyester resin
- a polyolefin resin base material is nonpolar and crystalline, and thus is difficult to paint or bond.
- Chlorinated polyolefin resin has adhesion to non-polar substrates as described above and is widely used.
- a chlorinated polyolefin resin has a problem of dehydrochlorination, and is therefore unsuitable for adhesion between a polyolefin resin and a metal.
- a non-aqueous dispersion type acid-modified polyolefin-based resin is generally used for adhesion between the polyolefin resin and the metal (Patent Document 1 and Patent Document 2).
- the adhesive based on the above-mentioned acid-modified polyolefin resin has a problem that roll contamination is likely to occur.
- there is a problem related to adhesive strength such as requiring heat sealing at a temperature exceeding 200 ° C.
- solution-type acid-modified polyolefin resins have been developed.
- solution-type acid-modified polyolefin resins can be improved with respect to problems such as roll contamination, further improvements in adhesive strength are required.
- the solution of the acid-modified polyolefin resin has a new problem that the stability at low temperature is low.
- an object of the present invention is to provide a modified polyolefin resin that is excellent in adhesion to a resin such as a polyolefin resin and a metal and excellent in stability of a solution at a low temperature.
- component (C) (meth) acrylic acid ester
- the melting point of the modified polyolefin resin by a differential scanning calorimeter is 91 ° C. or more and less than 120 ° C.
- the weight average molecular weight of the modified polyolefin resin is 100,000 or more and 200,000 or less
- Modified polyolefin resin that is soluble in solvents Modified polyolefin resin that is soluble in solvents.
- a primer comprising the modified polyolefin resin according to any one of [1] to [4] or the composition according to [5] or [6].
- An ink binder comprising the modified polyolefin resin according to any one of [1] to [4] above or the composition according to [5] or [6] above.
- a laminate comprising a layer comprising the modified polyolefin resin according to any one of [1] to [4] above or the composition according to [5] or [6], a metal layer, and a resin layer .
- the present invention can provide a modified polyolefin resin having excellent adhesion between a resin and a metal including a nonpolar resin such as a polyolefin resin and excellent stability of a solution at a low temperature.
- the modified polyolefin resin of the present invention is a modified polyolefin resin in which component (A) is graft-modified with component (B) and component (C). Components (A) to (C) will be described later.
- the modified polyolefin resin has a melting point (Tm) of 91 ° C. or more and less than 120 ° C. by a differential scanning calorimeter (DSC), and a weight average molecular weight of 100,000 or more and 200,000 or less.
- the modified polyolefin resin of the present invention exhibits an excellent effect is presumed as follows.
- the weight average molecular weight of the modified polyolefin resin is too large, the solubility in a solvent tends to decrease, and a stable solution tends to be difficult to obtain.
- the weight average molecular weight is too small, good adhesion tends to be difficult to obtain.
- the melting point of the modified polyolefin-based resin is low, the adhesive force cannot be maintained in the processing step after bonding, and satisfactory adhesion tends to be difficult to obtain.
- the melting point is too high, adhesion at low temperatures, good solvent solubility, and stability of the solution at low temperatures tend to be difficult to obtain.
- the modified polyolefin resin of the present invention includes a graft component derived from the components (B) and (C), and exhibits an excellent effect because the melting point and the weight average molecular weight are within a predetermined range. It is considered possible.
- the weight average molecular weight of the modified polyolefin resin is 100,000 or more, preferably 120,000 or more. Thereby, sufficient adhesive force can be expressed.
- the upper limit is 200,000 or less, preferably 180,000 or less. Thereby, sufficient solvent solubility can be obtained. Therefore, the weight average molecular weight of the modified polyolefin resin is 100,000 or more and 200,000 or less, and preferably 120,000 or more and 180,000 or less.
- the weight average molecular weight in the present invention including the examples is a value calculated by measuring with gel permeation chromatography (standard substance: polystyrene).
- the melting point of the modified polyolefin resin by a differential scanning calorimeter is 91 ° C. or higher, and preferably 95 ° C. or higher. Thereby, sufficient adhesive strength can be obtained.
- the melting point is less than 120 ° C., preferably 110 ° C. or less, and more preferably 105 ° C. or less. Thereby, adhesiveness at low temperature and solution stability are good, and sufficient storage stability at low temperature can be obtained. Accordingly, the melting point is 91 ° C. or higher and lower than 120 ° C., preferably 91 ° C. or higher and 115 ° C. or lower, and more preferably 95 ° C. or higher and 105 ° C. or lower.
- the measurement of Tm by DSC in the present invention can be performed, for example, under the following conditions.
- a DSC measuring device manufactured by Seiko Denshi Kogyo
- about 5 mg of sample is kept in a heated and melted state at 150 ° C. for 10 minutes and then cooled at a rate of 10 ° C./minute
- the melting peak temperature is measured when the temperature is further raised to 150 ° C. at 10 ° C./min to melt, and the temperature is evaluated as Tm.
- Tm is measured under the conditions described above.
- Component (A) is a polyolefin resin.
- the polyolefin resin is not particularly limited as long as it is a polymer of one or more olefin components.
- polyolefin resins include homopolymers of ⁇ -olefins having 2 to 6 carbon atoms (such as ethylene or propylene homopolymers); random copolymers or block copolymers of ethylene or propylene and other comonomers. Illustrated. Examples of other comonomers include 1-butene, 1-pentene, 1-hexene, 1-heptene and 1-octene.
- Component (A) may be one type of polyolefin resin or two or more types.
- Component (A) preferably contains at least one selected from the group consisting of ethylene-propylene copolymers, propylene-1-butene copolymers, and ethylene-propylene-1-butene copolymers. More preferably, it contains a 1-butene copolymer.
- the polyolefin resin contains a butene component
- the molar ratio of the butene component is preferably 5 to 30%, more preferably 10 to 25% of the whole polyolefin resin.
- the polyolefin resin contains a propylene component
- the molar ratio of the propylene component is preferably 40 to 90%, more preferably 65 to 80% of the entire polyolefin resin.
- the polyolefin resin contains an ethylene component
- the molar ratio of the ethylene component is preferably 3 to 20%, more preferably 5 to 10% of the entire polyolefin resin.
- the method for producing the polyolefin resin is not particularly limited.
- Component (B) is an ⁇ , ⁇ -unsaturated carboxylic acid and / or a derivative thereof.
- ⁇ , ⁇ -unsaturated carboxylic acid and its derivatives include maleic acid, maleic anhydride, fumaric acid, citraconic acid, citraconic anhydride, mesaconic acid, itaconic acid, itaconic anhydride, aconitic acid, aconitic anhydride, hymic anhydride Examples thereof include acid and (meth) acrylic acid, and maleic anhydride is preferred.
- Component (B) may be one or more compounds selected from ⁇ , ⁇ -unsaturated carboxylic acids and derivatives thereof, and a combination of one or more ⁇ , ⁇ -unsaturated carboxylic acids and one or more derivatives thereof, A combination of two or more ⁇ , ⁇ -unsaturated carboxylic acids or a combination of two or more derivatives of ⁇ , ⁇ -unsaturated carboxylic acids may be used.
- (meth) acrylic acid means methacrylic acid and / or acrylic acid.
- (Meth) acrylate means methacrylate and / or acrylate.
- the graft weight of the component (B) in the modified polyolefin resin is preferably 0.1% by weight or more, more preferably 0.5% by weight or more when the modified polyolefin resin is 100% by weight. More preferred. Thereby, the adhesiveness with respect to a metal adherend of the modified polyolefin resin obtained can be maintained.
- the upper limit is preferably 10% by weight or less, and more preferably 4% by weight or less. Thereby, generation
- the graft weight (% by weight) of component (B) can be measured by a known method. For example, it can be determined by alkali titration or Fourier transform infrared spectroscopy.
- Component (C) is a (meth) acrylic acid ester.
- the (meth) acrylic acid ester is an ester of acrylic acid or methacrylic acid.
- the component (C) preferably contains a (meth) acrylic acid ester represented by the general formula (I), and more preferably a (meth) acrylic acid ester represented by the general formula (I).
- CH 2 CR 1 COOR 2 (I)
- the component (C) may contain the (meth) acrylic acid ester represented by the general formula (I) alone, or may contain a plurality of types in combination at any ratio.
- R 1 represents H or CH 3 and is preferably CH 3 .
- R 2 represents C n H 2n + 1 .
- n represents an integer of 8 to 18, and n is preferably an integer of 8 to 15, more preferably an integer of 8 to 14, and still more preferably an integer of 8 to 13.
- lauryl (meth) acrylate and octyl (meth) acrylate are preferable, and lauryl methacrylate and octyl methacrylate are more preferable.
- the graft weight of component (C) in the modified polyolefin resin is preferably 0.1% by weight or more, more preferably 0.5% by weight or more when the modified polyolefin resin is 100% by weight. It is. Thereby, the molecular weight distribution of the modified polyolefin resin can be kept in a sufficiently narrow range. That is, the adverse effect of the high molecular weight portion can be suppressed, and the solvent solubility, the low temperature stability of the solution, and the compatibility with other resins can be maintained well. Moreover, the adhesive force can be improved by suppressing the adverse effect of the low molecular weight portion.
- the upper limit is preferably 10% by weight or less, more preferably 4% by weight or less.
- the graft weight of the component (C) is preferably 0.1% by weight or more and 10% by weight or less, more preferably 0.5% by weight or more and 4% by weight or less.
- the graft weight (% by weight) of component (C) can be measured by a known method. For example, it can be determined by Fourier transform infrared spectroscopy or 1 H-NMR.
- Component (C) may be one or more (meth) acrylic acid esters, and may be a combination of two or more (meth) acrylic acid esters.
- Either of the graft weight of component (B) and the graft weight of component (C) in the modified polyolefin resin is preferably 0.1 wt% or more and 10 wt% or less, and both are 0.1 wt% More preferably, the content is 10% by weight or less.
- a graft component (other graft component) other than components (B) and (C) may be used in combination as long as the properties of the present invention are not impaired.
- examples thereof include (meth) acrylic acid derivatives other than the component (C) (for example, N-methyl (meth) acrylamide, hydroxyethyl (meth) acrylamide, (meth) acryloylmorpholine, etc.).
- Other graft components may be used alone or in combination of two or more.
- the graft weight of the other graft components (the sum of them in the case of a plurality of combinations) is not particularly limited, but preferably does not exceed the sum of the graft weights of components (B) and (C).
- the method for producing the modified polyolefin resin can be obtained by graft polymerization of the component (B) and the component (C) to the component (A).
- component (D): radical generator may be used.
- the radical generator may be a known radical generator, and is preferably an organic peroxide compound.
- organic peroxide compounds include di-t-butyl peroxide, dicumyl peroxide, t-butyl cumyl peroxide, benzoyl peroxide, dilauryl peroxide, cumene hydroperoxide, and t-butyl hydroperoxide.
- Component (D) may be a single radical generator or a combination of a plurality of radical
- a method for producing a modified polyolefin resin using component (D) for example, a mixture of components (A), (B) and (C) is heated and dissolved in an organic solvent such as toluene and xylene, and then component (D ) And the components (A), (B), (C) and (D) are added using a kneading machine such as a Banbury mixer, a kneader, or an extruder, and the melt kneading reaction is performed under heating.
- a kneading machine such as a Banbury mixer, a kneader, or an extruder, and the melt kneading reaction is performed under heating.
- a method for obtaining a modified polyolefin-based resin is mentioned.
- the components (A), (B), (C) and (D) may be added to the reaction system all at once or sequentially.
- the addition amount of component (D) in the graft polymerization reaction is preferably 1% by weight, more preferably 10%, based on the total amount (weight) of the addition amount of component (B) and the addition amount of component (C). % By weight. Thereby, sufficient grafting efficiency can be maintained.
- the upper limit is preferably 100% by weight or less, and more preferably 50% by weight or less. Thereby, the fall of the weight average molecular weight of modified polyolefin resin can be suppressed.
- the modified polyolefin resin of the present invention can exhibit stability (solution stability) when mixed with a solvent to form a solution, particularly solution stability at low temperatures (for example, 25 ° C. or less, 5 ° C. or more). it can.
- the modified polyolefin resin of the present invention can exhibit excellent adhesion between a metal and a resin, and since it has solution stability at a low temperature, it also has excellent adhesion at a low temperature.
- the metal include aluminum, aluminum alloy, nickel, and stainless steel.
- the resin include nonpolar resins such as polyolefin resins, polyurethane resins, polyamide resins, acrylic resins, and polyester resins. Therefore, the modified polyolefin resin of the present invention can be used as an adhesive, a primer, a paint binder and an ink binder or as these components.
- the modified polyolefin resin of the present invention may be used as a composition in combination with other components.
- the composition of the present invention only needs to contain a modified polyolefin resin, and other components are not particularly limited. Examples of other components include a curing agent, an adhesive component, and a solvent.
- curing agent examples include polyisocyanate compounds, epoxy compounds, polyamine compounds such as isophorone diamine, polyol compounds, and cross-linking agents whose functional groups are blocked with protecting groups.
- curing agent may be individual and may be a combination of multiple types.
- curing agent can be suitably selected with content of the component (B) in the modified polyolefin resin of this invention.
- the composition of the present invention may contain a catalyst.
- the catalyst include organotin compounds and tertiary amine compounds, which may be appropriately selected from these according to the purpose.
- Examples of the adhesive component include known adhesives such as polyester adhesives, polyurethane adhesives, and acrylic adhesives.
- Solvents include aromatic solvents (toluene, xylene, etc.); alicyclic hydrocarbon solvents (cyclohexane, methylcyclohexane, etc.); aliphatic hydrocarbon solvents (hexane, heptane, octane, etc.); ketone solvents (acetone, methyl ethyl ketone, Ester solvents (such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, and n-butyl acetate) glycol solvents (such as ethylene glycol, ethyl cellosolve, and butyl cellosolve); alcohol solvents (methanol, Ethanol, n-butanol, t-butanol, etc.); and mixed solvents thereof.
- aromatic solvents toluene, xylene, etc.
- alicyclic hydrocarbon solvents cyclohexan
- the solvent is preferably an aromatic solvent (preferably toluene), an alicyclic hydrocarbon solvent (preferably cyclohexane), or a mixed solvent thereof.
- the weight ratio of each solvent in the mixed solvent is not particularly limited, but is preferably 6/4 in the case of the aromatic solvent / alicyclic hydrocarbon solvent.
- the composition of the present invention only needs to contain the modified polyolefin resin of the present invention, and the content ratio with other components that may be contained as needed is not particularly limited.
- the content (weight ratio) of the modified polyolefin resin of the present invention relative to the total amount of the composition is preferably 5% by weight or more, more preferably 10% by weight or more, and more preferably 20% by weight or more. Even more preferred.
- An upper limit is not specifically limited, What is necessary is just to be less than 100 weight%, and it is preferable that it is 95 weight% or less.
- the composition of the present invention is excellent in adhesiveness with resin and metal and solution stability, it can be used as an adhesive for metal and / or resin, a primer, a binder for paint, and a binder for ink.
- it is useful as an adhesive in a laminate film such as an aluminum laminate film.
- the modified polyolefin resin or composition of the present invention may be one material of layers constituting the laminate.
- the laminate of the present invention has a layer containing the modified polyolefin resin or composition of the present invention, a metal layer, and a resin layer.
- the arrangement of the layers in the laminate is not particularly limited, but the mode in which the metal layer and the resin layer are positioned with the layer containing the modified polyolefin resin or composition interposed therebetween, the first resin layer and the second resin with the metal layer interposed therebetween
- a mode in which a layer exists and a layer containing a modified polyolefin resin or composition is sandwiched between the metal layer and each resin layer is exemplified.
- the laminate of the present invention may be used as an exterior material for lithium ion secondary batteries, capacitors, electric double layer capacitors and the like, and is preferably used.
- Example 3 In Example 2, it modified
- ⁇ Test 1 Solution stability test> The solution sample was put in a sealed glass bottle and stored at 5 ° C. for 7 days, and then visually evaluated for appearance.
- ⁇ Test 2 Adhesive strength test> The solution sample was applied as an adhesive with a # 16 Meyer bar on a 1.0 mm thick SUS304-2B plate and an aluminum foil with a resin dry film thickness of 2 ⁇ m, and dried at 180 ° C. for 10 seconds. The coated aluminum foil was bonded to an unstretched polypropylene (CPP) sheet and thermocompression bonded under conditions of 200 kPa at 120 ° C. for 3 seconds to prepare a test piece cut out to a width of 15 mm. After the test piece was stored at 23 ° C. and 50% relative humidity for 24 hours at constant temperature and humidity, the laminate adhesive strength was measured under the conditions of 180-degree direction peeling and peeling speed of 100 mm / min.
- CPP polypropylene
- the modified polyolefin resins of Examples 1 to 8 are excellent in adhesiveness between the aluminum foil and the polypropylene sheet, and simultaneously have low-temperature storage stability of the solution.
- the modified polyolefin resin of Comparative Example 1 whose weight average molecular weight and melting point are not within the scope of the present invention was inferior in adhesive strength as compared with Examples 1-8.
- the modified polyolefin resin of Comparative Example 2 whose melting point is not within the scope of the present invention, and the modified polyolefin resin of Comparative Example 3 having a low molecular weight that is not modified with the component (C) are a solution in comparison with Examples 1 to 8. Both stability and adhesive strength were inferior.
- modified polyolefin resin of the present invention is excellent in adhesiveness to both resin and metal and excellent in solution stability at low temperatures.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
L'objet de la présente invention est de pourvoir à une résine polyoléfinique modifiée ayant une excellente adhésivité aux métaux et aux matériaux de base non polaires tels que les résines polyoléfiniques et une excellente stabilité en solution à basse température. La résine polyoléfinique modifiée selon l'invention comprend une résine polyoléfinique (composant (A)) qui est modifiée par greffage par un acide carboxylique α,β-unsaturé et/ou un dérivé de celui-ci (composant (B)) et un ester d'acide (méth)acrylique (composant (C)), la résine polyoléfinique modifiée selon l'invention ayant un point de fusion déterminé par analyse calorimétrique différentielle à balayage (DSC) de 91°C à moins de 120°C et un poids moléculaire moyen en poids de 100 000 à 200 000.
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2015152101A1 (fr) * | 2014-03-31 | 2015-10-08 | 日本製紙株式会社 | Corps composite multicouche de métal et de de composition de résine de polypropylène et son procédé de production |
JP2017074674A (ja) * | 2014-03-31 | 2017-04-20 | 合資会社アンドーコーポレーション | 金属とポリプロピレン系樹脂組成物の複合体とその製造方法 |
JP2017074675A (ja) * | 2014-12-04 | 2017-04-20 | 合資会社アンドーコーポレーション | 金属とポリプロピレン系樹脂組成物の積層複合体とその製造方法 |
JP2018150482A (ja) * | 2017-03-14 | 2018-09-27 | 日本製紙株式会社 | 変性ポリオレフィン樹脂 |
JPWO2018037849A1 (ja) * | 2016-08-24 | 2019-06-20 | 日本製紙株式会社 | 変性ポリオレフィン系樹脂 |
JP2020143181A (ja) * | 2019-03-04 | 2020-09-10 | 日本製紙株式会社 | 変性ポリオレフィン樹脂 |
WO2022210053A1 (fr) * | 2021-04-02 | 2022-10-06 | 住友化学株式会社 | Résine de polyoléfine modifiée |
WO2022210054A1 (fr) * | 2021-04-02 | 2022-10-06 | 住友化学株式会社 | Dispersion aqueuse |
WO2024252905A1 (fr) * | 2023-06-09 | 2024-12-12 | 東洋紡エムシー株式会社 | Composition adhésive à base de polyoléfine |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5473839A (en) * | 1977-11-24 | 1979-06-13 | Ricoh Co Ltd | Non-aqueous resin dispersion |
JP2002173514A (ja) * | 2000-09-29 | 2002-06-21 | Nippon Paper Industries Co Ltd | 変性ポリオレフィン樹脂と変性ポリオレフィン樹脂組成物及びその用途 |
WO2005082963A1 (fr) * | 2004-02-26 | 2005-09-09 | Nippon Paper Chemicals Co., Ltd. | Résine de polyoléfine modifiée |
JP2008239925A (ja) * | 2007-03-29 | 2008-10-09 | Nippon Paper Chemicals Co Ltd | 分散樹脂組成物およびその製造方法 |
JP2011148871A (ja) * | 2010-01-20 | 2011-08-04 | Seiko Pmc Corp | 変性ポリオレフィン樹脂水性分散体の製造方法 |
JP2013032600A (ja) * | 2011-08-01 | 2013-02-14 | Dic Corp | 炭素繊維集束剤、炭素繊維及び成形材料 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03276515A (ja) * | 1990-03-26 | 1991-12-06 | Hitachi Cable Ltd | 耐水トリー性電線・ケーブル |
JP2011143709A (ja) * | 2009-12-16 | 2011-07-28 | Toray Ind Inc | 積層フィルム、それを用いた蒸着フィルム |
JP4992136B2 (ja) * | 2010-03-23 | 2012-08-08 | 住友電工ファインポリマー株式会社 | 定着ユニット用部材の製造方法及び定着ユニット用部材 |
-
2014
- 2014-11-28 JP JP2015551026A patent/JP6353464B2/ja active Active
- 2014-11-28 WO PCT/JP2014/081639 patent/WO2015080269A1/fr active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5473839A (en) * | 1977-11-24 | 1979-06-13 | Ricoh Co Ltd | Non-aqueous resin dispersion |
JP2002173514A (ja) * | 2000-09-29 | 2002-06-21 | Nippon Paper Industries Co Ltd | 変性ポリオレフィン樹脂と変性ポリオレフィン樹脂組成物及びその用途 |
WO2005082963A1 (fr) * | 2004-02-26 | 2005-09-09 | Nippon Paper Chemicals Co., Ltd. | Résine de polyoléfine modifiée |
JP2008239925A (ja) * | 2007-03-29 | 2008-10-09 | Nippon Paper Chemicals Co Ltd | 分散樹脂組成物およびその製造方法 |
JP2011148871A (ja) * | 2010-01-20 | 2011-08-04 | Seiko Pmc Corp | 変性ポリオレフィン樹脂水性分散体の製造方法 |
JP2013032600A (ja) * | 2011-08-01 | 2013-02-14 | Dic Corp | 炭素繊維集束剤、炭素繊維及び成形材料 |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015152101A1 (fr) * | 2014-03-31 | 2015-10-08 | 日本製紙株式会社 | Corps composite multicouche de métal et de de composition de résine de polypropylène et son procédé de production |
JP2017074674A (ja) * | 2014-03-31 | 2017-04-20 | 合資会社アンドーコーポレーション | 金属とポリプロピレン系樹脂組成物の複合体とその製造方法 |
JP2017074675A (ja) * | 2014-12-04 | 2017-04-20 | 合資会社アンドーコーポレーション | 金属とポリプロピレン系樹脂組成物の積層複合体とその製造方法 |
JPWO2018037849A1 (ja) * | 2016-08-24 | 2019-06-20 | 日本製紙株式会社 | 変性ポリオレフィン系樹脂 |
JP2018150482A (ja) * | 2017-03-14 | 2018-09-27 | 日本製紙株式会社 | 変性ポリオレフィン樹脂 |
JP2020143181A (ja) * | 2019-03-04 | 2020-09-10 | 日本製紙株式会社 | 変性ポリオレフィン樹脂 |
WO2022210053A1 (fr) * | 2021-04-02 | 2022-10-06 | 住友化学株式会社 | Résine de polyoléfine modifiée |
WO2022210054A1 (fr) * | 2021-04-02 | 2022-10-06 | 住友化学株式会社 | Dispersion aqueuse |
WO2024252905A1 (fr) * | 2023-06-09 | 2024-12-12 | 東洋紡エムシー株式会社 | Composition adhésive à base de polyoléfine |
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