EP3908618A1 - Verwendung von thermisch stabilen terpenphenolharzen - Google Patents
Verwendung von thermisch stabilen terpenphenolharzenInfo
- Publication number
- EP3908618A1 EP3908618A1 EP20700426.8A EP20700426A EP3908618A1 EP 3908618 A1 EP3908618 A1 EP 3908618A1 EP 20700426 A EP20700426 A EP 20700426A EP 3908618 A1 EP3908618 A1 EP 3908618A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acrylate
- terpene
- adhesive
- methacrylate
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000005011 phenolic resin Substances 0.000 title claims abstract description 67
- 229920000642 polymer Polymers 0.000 claims abstract description 47
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims abstract description 34
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 18
- 238000009826 distribution Methods 0.000 claims abstract description 7
- 238000004458 analytical method Methods 0.000 claims abstract description 5
- 235000007586 terpenes Nutrition 0.000 claims description 71
- 150000003505 terpenes Chemical class 0.000 claims description 70
- 229920001568 phenolic resin Polymers 0.000 claims description 39
- 239000004840 adhesive resin Substances 0.000 claims description 24
- 229920006223 adhesive resin Polymers 0.000 claims description 24
- 229920000058 polyacrylate Polymers 0.000 claims description 24
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 22
- 229920000193 polymethacrylate Polymers 0.000 claims description 19
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229920005989 resin Polymers 0.000 abstract description 23
- 239000011347 resin Substances 0.000 abstract description 23
- 238000003860 storage Methods 0.000 abstract description 9
- 239000000178 monomer Substances 0.000 description 57
- -1 terpene phenolic resin compounds Chemical class 0.000 description 39
- 230000001070 adhesive effect Effects 0.000 description 33
- 239000000853 adhesive Substances 0.000 description 32
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 28
- 239000002390 adhesive tape Substances 0.000 description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
- 239000000203 mixture Chemical class 0.000 description 21
- 238000004132 cross linking Methods 0.000 description 19
- 239000010410 layer Substances 0.000 description 18
- 230000009477 glass transition Effects 0.000 description 16
- 150000004820 halides Chemical class 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 150000002118 epoxides Chemical class 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- 125000003700 epoxy group Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 10
- 230000032683 aging Effects 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 238000012545 processing Methods 0.000 description 8
- 238000010526 radical polymerization reaction Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 125000005396 acrylic acid ester group Chemical group 0.000 description 6
- 239000012790 adhesive layer Substances 0.000 description 6
- 230000000181 anti-adherent effect Effects 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000937 dynamic scanning calorimetry Methods 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
- 229940097156 peroxyl Drugs 0.000 description 5
- NJXYTXADXSRFTJ-UHFFFAOYSA-N 1,2-Dimethoxy-4-vinylbenzene Chemical compound COC1=CC=C(C=C)C=C1OC NJXYTXADXSRFTJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000008646 thermal stress Effects 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- 230000003442 weekly effect Effects 0.000 description 4
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 3
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 3
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920005601 base polymer Polymers 0.000 description 3
- 229930006722 beta-pinene Natural products 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 description 3
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
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- 238000006467 substitution reaction Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
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- PLDLPVSQYMQDBL-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propoxy]methyl]oxirane Chemical compound C1OC1COCC(COCC1OC1)(COCC1OC1)COCC1CO1 PLDLPVSQYMQDBL-UHFFFAOYSA-N 0.000 description 2
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- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940091181 aconitic acid Drugs 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
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- 229920003002 synthetic resin Polymers 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
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 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 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- RRLMGCBZYFFRED-UHFFFAOYSA-N undecyl prop-2-enoate Chemical compound CCCCCCCCCCCOC(=O)C=C RRLMGCBZYFFRED-UHFFFAOYSA-N 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000019352 zinc silicate Nutrition 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
Definitions
- the invention relates to the use of at least one terpene-phenol resin as an adhesive resin for PSAs based on polar backbone polymers and a PSA comprising at least one polar backbone polymer and at least one terpene-phenol resin as an adhesive resin and a PSA tape with at least one layer of the PSA of the invention.
- Terpene phenolic resins are adhesive resins, which are made up of a terpene building block, which is mostly of natural origin, and a phenol building block, which is mostly of petro-origin.
- a-pinene, ⁇ -pinene or 53-carene are commonly used as terpene units today. These pinenes are reacted alone or in combination with phenol or substituted phenols or mixtures thereof. The reaction process is usually a cationic polymerization. This gives terpene phenol resins with average molecular weights of about 100 to 10,000 g / mol, preferably 500 to 2,000 g / mol. a-pinene, ß-pinene and 53-carene accumulate in the tree resin of different types of pine. The raw materials are then actually isolated using extraction processes. In addition, a-pinene, ß-pinene and 53-carene also occur in paper production (in the Kraft Pulping process). The terpenes are then accessible in high purity through further reaction steps, which also include fractional distillations.
- a pure unsubstituted phenol of petrochemical origin is usually used as the phenol component.
- the terpene phenol resins thus produced which, owing to the phenol, have a high polarity and better aging behavior than, for example, hydrocarbon resins or rosin derivatives, can then be used as tackifiers for PSAs, in particular those based on elastomers in the form of polar framework polymers such as polyacrylates can be used.
- Pressure sensitive adhesives are in particular those polymeric compositions which - if appropriate through suitable additives with other components such as adhesive resins - at the application temperature (unless otherwise defined, at room temperature) are permanently sticky and tacky and adhere to a variety of surfaces on contact, in particular immediately. You are able to adequately wet a substrate to be bonded even at the application temperature without activation by solvents or heat - but usually due to the influence of a more or less high, in particular manual, contact pressure, so that there is between the mass and the substrate liability can develop sufficient interactions.
- a pressure-sensitive adhesive has a permanent pressure-sensitive adhesive at room temperature, that is to say it has a sufficiently low viscosity and high tack, so that it wets the surface of the adhesive base in question even with slight pressure.
- the adhesiveness of the adhesive is based on its adhesive properties and the releasability on its cohesive properties.
- Tackifiers are compounds that give tack and tack to an adhesive.
- a tack is the ability of a material to adhere spontaneously to a solid surface when it is brought into contact with it under very slight pressure (see “Handbook of Pressure Sensitive Adhesive Technology”, Donatas Satas, Third Edition, 1999 , Pp. 36 to 61).
- the tack of an adhesive or an adhesive tape depends on numerous features and the person skilled in the art knows how to achieve a desired tack. These features are, for example, the surface roughness and surface tension of the adhesive layer.
- the composition of the PSA also has a major impact.
- the type of base polymer is relevant, for example. Among other things, its molecular weight and polarity play a role here.
- Polyacrylates based on acrylic acid esters with defined chain lengths of the ester side groups show, for example, pressure-sensitive properties. If the length of the ester side groups exceeds a certain amount, the tacky ones go Properties lost due to crystallization of the polymer.
- the polarity of polyacrylates can be set, for example, via their acrylic acid content.
- an “adhesive resin” is understood to mean a low-molecular, oligomeric or polymeric resin which increases the adhesion (tack, inherent tack) of the PSA compared to the PSA which contains no adhesive but is otherwise identical. As the proportion of adhesive resin increases, as does the proportion of plasticizer, the tack and adhesive strength increase. Due to the excellent properties of terpene phenolic resins, this type of resin is preferred as an adhesive resin.
- Polyacrylates are polar framework polymers.
- the adhesive resin must be compatible with the scaffold polymer.
- the glass transition point of the adhesive resin should be significantly above the glass transition point of the elastomer.
- the molar mass of the adhesive resin should be significantly lower than the molar mass of the elastomeric framework polymer. Another decisive criterion is that the adhesive resin shows good stability during aging.
- a terpene phenolic resin can incorporate the desired properties into a pressure sensitive adhesive consisting of a compound made of a framework polymer and a tackifier resin.
- the softening points of terpene phenolic resins can be set as desired within wide limits. For PSAs, softening points between 60 ° C and 200 ° C, in particular between 95 ° C and 135 ° C, are of interest due to the applications.
- a-pinene-based terpene phenolic resins The stability of a-pinene-based terpene phenolic resins was investigated for the production of polyacrylate / terpene phenolic resin compounds. It was found that the stability of a-pinene-based terpene phenolic resins deteriorated continuously with a decrease in the softening point. In other words: the lower the softening point of the a-pinene-based terpene phenolic resin, the lower the aging stability. The aging of these terpene phenolic resins manifests itself in a continuously increasing softening point over time. In particular, a-pinene-based terpene-phenolic resins with a softening point below about 110 ° C prove to be more unstable with thermal aging than terpene-phenolic resins with a higher softening point.
- the object of the present invention was to remedy the situation and to provide adhesive resins which do not have this defect, i.e. which have a good aging stability, they also show good compatibility with polyacrylates and should meet the above-described requirements for a tackifier resin with regard to compatibility with the framework polymer, glass transition point and molecular weight.
- the present invention relates to the use of at least one terpene phenol resin as an adhesive resin for PSAs based on polar skeletal polymers, the at least one terpene phenol resin in the gel permeation chromatographic analysis showing a multimodal molar mass distribution, the low molecular peak reaching its maximum in a range above 260 g / mol has.
- the object is further achieved by a PSA comprising at least one polar backbone polymer and at least one terpene-phenol resin as the adhesive resin, the at least one terpene-phenol resin showing a multimodal molar mass distribution in the gel permeation chromatography investigation, the low-molecular peak reaching its maximum in a range above 260 g / mol has.
- Advantageous embodiments of the use according to claim 1 and the PSA according to claim 6 are given in the subclaims.
- the softening point of the terpene phenolic resins is almost stable even after aging and an increase in the softening point does not show to the extent that can be observed with terpene phenolic resins which have terpenes as their terpene component, the peak of which in the low molecular weight range is below 260 g / mol, for example 250 g / mol.
- the low molecular weight fraction of terpene phenolic resins with a peak below 260 g / mol contains constituents which are responsible for the instability of the terpene phenolic resins based on such terpenes and having a low softening point.
- These by-products consist of a mixture of terpene components such as, for example, terpene dimers, terpene trimers, para-cymols, terpene alcohols and terpene phenol components, mainly mono-terpene phenols, which can also be present in part in oxidized form.
- the at least one terpene-phenolic resin 53-carene is particularly advantageous, ie 53-carene is the terpene base for the terpene-phenolic resin.
- the expression “base” or “based” means that predominantly 53-carene is used as the terpene and the properties, insofar as they are caused by the terpene, are determined.
- the softening points of terpene phenolic resins can be set as desired within wide limits.
- Terpenophenol resins with softening points between 60 ° C. and 200 ° C., in particular between 95 ° C. and 135 ° C., particularly preferably between 95 ° C. and 110 ° C., are particularly suitable for PSAs according to the invention.
- terpene phenolic resins with a softening point below about 110 ° C prove to be more unstable with thermal aging than terpene phenolic resins with a higher softening point.
- the present invention makes it possible to provide terpene-phenol resins with a softening point of less than 110 ° C., ie terpene-phenol resins with a low softening point, in an aging-stable manner.
- the terpene phenol resin further contains other terpenes, in particular a-pinene.
- the properties of the terpene phenolic resin can be modified further by using further terpenes.
- the PSA contains 20 to 60% by weight of at least one adhesive resin, based on the total weight of the PSA, preferably 30 to 50% by weight of at least one adhesive resin, based on the total weight of the PSA.
- the present invention is suitable for various polar backbone polymers. It is particularly suitable for poly (meth) acrylates.
- a “poly (meth) acrylate” is understood to mean a polymer whose monomer base consists of at least 60% by weight of acrylic acid, methacrylic acid, acrylic acid esters and / or methacrylic acid esters, acrylic acid esters and / or methacrylic acid esters at least in part, preferably at least 50 % By weight, based on the total monomer base of the polymer in question, are present.
- a “poly (meth) acrylate” is understood to mean a polymer which is obtained by radical polymerization of acrylic and / or Methacrylic monomers and optionally other copolymerizable monomers is available.
- the poly (meth) acrylate or poly (eth) acrylates are present in an amount of 40 to 80% by weight, based on the total weight of the PSA.
- the PSA according to the invention preferably contains 50 to 70% by weight, based on the total weight of the PSA, of at least one poly (meth) acrylate.
- the glass transition temperature of the poly (meth) acrylates which can be used according to the invention is preferably ⁇ 0 ° C, more preferably between -20 and -50 ° C.
- the glass transition temperature of polymers or polymer blocks in block copolymers is determined in the context of this invention by means of dynamic scanning calorimetry (DSC).
- the poly (meth) acrylates of the PSA according to the invention are preferably obtainable by at least partial copolymerization of functional monomers which are preferably crosslinkable with epoxy groups. These are particularly preferably monomers with acid groups (especially carboxylic acid, sulfonic acid or phosphonic acid groups) and / or hydroxyl groups and / or acid anhydride groups and / or epoxy groups and / or amine groups; carboxylic acid-containing monomers are particularly preferred. It is very particularly advantageous if the polyacrylate has polymerized acrylic acid and / or methacrylic acid. All of these groups have a crosslinking ability with epoxy groups, as a result of which the polyacrylate is advantageously accessible to thermal crosslinking with introduced epoxides.
- monomers that can be used as comonomers for the poly (meth) acrylates are, in addition to acrylic acid and / or methacrylic acid esters with up to 30 C atoms per molecule, for example vinyl esters of carboxylic acids containing up to 20 C atoms, vinyl aromatics with up to 20 carbon atoms, ethylenically unsaturated nitriles, vinyl halides, vinyl ethers of alcohols containing 1 to 10 carbon atoms, aliphatic hydrocarbons with 2 to 8 carbon atoms and one or two double bonds or mixtures of these monomers.
- the properties of the poly (meth) acrylate in question can be influenced in particular by varying the glass transition temperature of the polymer by means of different proportions by weight of the individual monomers.
- the poly (meth) acrylate (s) of the invention can preferably be attributed to the following monomer composition:
- R ' H or CH3 and R "is an alkyl radical having 4 to 14 carbon atoms
- component (a) optionally further acrylates and / or methacrylates and / or olefinically unsaturated monomers which can be copolymerized with component (a).
- the proportions of the corresponding components (a), (b) and (c) are preferably selected such that the polymerization product has a glass transition temperature of ⁇ 0 ° C., more preferably between -20 and -50 ° C. (DSC). It is particularly advantageous to use the monomers of component (a) in a proportion of 45 to 99% by weight, the monomers in component (b) in a proportion of 1 to 15% by weight and the monomers in component (c) with a proportion of 0 to 40% by weight (the information is based on the monomer mixture for the “base polymer”, ie without any additives to the finished polymer such as resins etc.).
- the monomers of component (a) are in particular plasticizing and / or non-polar monomers.
- Acrylic and methacrylic acid esters with alkyl groups consisting of 4 to 14 C atoms, particularly preferably 4 to 9 C atoms, are preferably used as monomers (a).
- Examples of such monomers are n-butyl acrylate, n-butyl methacrylate, n-pentyl acrylate, n-pentyl methacrylate, n-amyl acrylate, n-hexyl acrylate, n-hexyl methacrylate, n-heptyl acrylate, n-octyl acrylate, n-octyl methacrylate, n-nonyl acrylate and n-nonyl acrylate branched isomers, such as isobutyl acrylate, isooctyl acrylate, isooctyl methacrylate, 2-ethylhexyl acrylate or 2-ethylhexyl methacrylate.
- the monomers of component (b) are in particular olefinically unsaturated monomers with functional groups, in particular with functional groups, which can react with epoxy groups.
- Monomers with functional groups which are selected from the group comprising: hydroxyl, carboxy, sulfonic acid or phosphonic acid groups, acid anhydrides, epoxides, amines are preferably used for component (b).
- monomers of component (b) are acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid, aconitic acid, dimethylacrylic acid, ß-acryloyloxypropionic acid, trichloracrylic acid, vinyl acetic acid, vinyl phosphonic acid, maleic anhydride, hydroxyethyl acrylate, especially 2-hydroxyethyl acrylate, especially 2-hydroxyethyl acrylate in particular 3-hydroxypropyl acrylate, hydroxybutyl acrylate, in particular 4-hydroxybutyl acrylate, hydroxyhexyl acrylate, in particular 6-hydroxyhexyl acrylate, hydroxyethyl methacrylate, in particular 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, in particular 3-hydroxypropyl methacrylate, hydroxybutyl methacrylate, in particular 4-hydroxyethyl acrylate, in particular 4-hydroxyethyl acrylate,
- component (c) all vinylically functionalized compounds which can be copolymerized with component (a) and / or component (b) can be used as component (c).
- the monomers of component (c) can be used to adjust the properties of the resulting PSA.
- Exemplary monomers of component (c) are:
- Monomers of component (c) can advantageously also be chosen such that they contain functional groups which support subsequent radiation-chemical crosslinking (for example by means of electron beams, UV).
- Suitable copolymerizable photoinitiators are, for example, benzoin acrylate and acrylate-functionalized benzophenone derivatives.
- Monomers which support crosslinking by electron radiation are, for example, tetrahydrofurfury acrylate, N-te / f-butylacrylamide and allyl acrylate.
- polyacrylates is understood in the context of the invention as synonymous with “poly (meth) acrylates”
- poly (meth) acrylates can be carried out by methods familiar to the person skilled in the art, in particular advantageously by means of conventional free-radical polymerizations or controlled free-radical polymerizations.
- the polyacrylates can be prepared by copolymerizing the monomeric components using the customary polymerization initiators and, if appropriate, regulators, with the usual temperatures in bulk, in emulsion, for example in water or liquid hydrocarbons, or in solution.
- the polyacrylates are preferably obtained by polymerizing the monomers in solvents, in particular in solvents with a boiling range from 50 to 150 ° C., preferably from 60 to 120 ° C., using the customary amounts of polymerization initiators, which are generally from 0.01 to 5, in particular 0.1 to 2 wt .-%, based on the total weight of the monomers.
- radical sources are peroxides, hydroperoxides and azo compounds, for example dibenzoyl peroxide, cumene hydroperoxide, cyclohexanone peroxide, di-f-butyl peroxide, cyclohexylsulfonylacetyl peroxide, diisopropyl percarbonate, f-butyl peroctoate, benzpinacol.
- Suitable solvents for the preparation of the poly (meth) acrylates are alcohols such as methanol, ethanol, n- and iso-propanol, n- and iso-butanol, preferably isopropanol and / or isobutanol, and hydrocarbons such as toluene and in particular gasolines with a boiling range of 60 up to 120 ° C in question.
- alcohols such as methanol, ethanol, n- and iso-propanol, n- and iso-butanol, preferably isopropanol and / or isobutanol
- hydrocarbons such as toluene and in particular gasolines with a boiling range of 60 up to 120 ° C in question.
- ketones such as preferably acetone, methyl ethyl ketone, methyl isobutyl ketone and esters such as ethyl acetate and mixtures of solvents of the type mentioned can be used, mixtures containing isopropanol, in particular in amounts of 2 to 15% by weight, preferably 3 to 10% by weight, based on the solvent mixture used, are preferred.
- a concentration is preferably carried out after the production (polymerization) of the polyacrylates, and the further processing of the polyacrylates is essentially solvent-free.
- the polymer can be concentrated in the absence of crosslinking agent and accelerator substances. However, it is also possible to add one of these classes of compounds to the polymer before the concentration, so that the concentration then takes place in the presence of this substance (s).
- the weight average molecular weights Mw of the polyacrylates are preferably in a range from 20,000 to 2,000,000 g / mol; very preferably in a range from 100,000 to 1,500,000 g / mol, very preferably in a range from 150,000 to 1,000,000 g / mol.
- the details of the average molecular weight Mw and the polydispersity PD in this document relate to the determination by gel permeation chromatography.
- suitable polymerization regulators such as thiols, halogen compounds and / or alcohols, in order to set the desired average molecular weight.
- the polyacrylates preferably have a K value of 30 to 90, particularly preferably 40 to 70, measured in toluene (1% solution, 21 ° C.).
- the K value according to Fikentscher is a measure of the molecular weight and the viscosity of the polymer.
- Polyacrylates which have a narrow molecular weight distribution are particularly suitable according to the invention. Despite a relatively low molecular weight, these compositions have particularly good shear strength after crosslinking. In addition, the lower polydispersity enables easier processing from the melt, since the flow viscosity is lower compared to a more widely distributed polyacrylate with largely the same application properties.
- Narrowly distributed poly (meth) acrylates can advantageously be prepared by anionic polymerization or by controlled radical polymerization methods, the latter being particularly suitable. Corresponding polyacrylates can also be produced via / V-oxyls.
- atom transfer radical polymerization can advantageously be used for the synthesis of narrowly distributed polyacrylates, the initiator preferably being monofunctional or difunctional secondary or tertiary halides and for the abstraction of the (r) halide (s) Cu, Ni, Fe -, Pd, Pt, Ru, Os, Rh, Co, Ir, Ag or Au complexes are used.
- the monomers for the preparation of the poly (meth) acrylates preferably contain a proportion of functional groups which are suitable for undergoing linkage reactions with epoxy groups. This advantageously enables thermal crosslinking of the polyacrylates by reaction with epoxides.
- Linking reactions are understood to mean, in particular, addition and substitution reactions.
- there is a linkage of the building blocks carrying the functional groups with building blocks carrying epoxy groups in particular in the sense of a crosslinking of the functional groups carrying polymer building blocks over epoxy groups carrying crosslinker molecules as linking bridges.
- the substances containing epoxide groups are preferably multifunctional epoxides, that is to say those having at least two epoxide groups; Accordingly, there is preferably an overall indirect connection of the building blocks carrying the functional groups.
- the poly (meth) acrylates of the PSA of the invention are preferably crosslinked by means of linking reactions - in particular in the sense of addition or substitution reactions - of the functional groups they contain with thermal crosslinking agents.
- All thermal crosslinkers can be used, which both ensure a sufficiently long processing time, so that there is no gelling during the processing process, in particular the extrusion process, and rapid postcrosslinking of the polymer to the desired degree of crosslinking at temperatures lower than that Processing temperature, especially at room temperature.
- a combination of polymers containing carboxyl, amine and / or hydroxyl groups and isocyanates, in particular aliphatic or trimerized isocyanates deactivated with amines is possible as the crosslinking agent.
- Suitable isocyanates are, in particular, trimerized derivatives of MDI [4,4-methylene di (phenyl isocyanate)], HDI [hexamethylene diisocyanate, 1,6-hexylene diisocyanate] and / or IPDI [isophorone diisocyanate, 5-isocyanato-1-isocyanatomethyl-1,3. 3-trimethylcyclohexane], for example the types Desmodur® N3600 and XP2410 (each BAYER AG: aliphatic polyisocyanates, low-viscosity HDI trimerizates).
- the surface-deactivated dispersion of micronized trimerized IPDI BUEJ 339®, now HF9 ® (BAYER AG) is also suitable.
- isocyanates such as Desmodur VL 50 (polyisocyanates based on MDI, Bayer AG), basonate F200WD (aliphatic polyisocyanate, BASF AG), basonate HW100 (water-emulsifiable polyfunctional isocyanate based on HDI, BASF AG), basonate are also suitable for crosslinking HA 300 (allophanate-modified polyisocyanate based on isocyanurate. HDI, BASF) or Bayhydur VPLS2150 / 1 (hydrophilically modified IPDI, Bayer AG).
- Thermal crosslinkers are preferably used in an amount of 0.1 to 5% by weight, in particular 0.2 to 1% by weight, based on the total amount of the polymer to be crosslinked.
- the poly (meth) acrylates of the PSA according to the invention are preferably crosslinked by means of epoxy (s) or by means of one or more substance (s) containing epoxy groups.
- the substances containing epoxide groups are in particular multifunctional epoxides, that is to say those with at least two epoxide groups; Accordingly, there is an overall indirect linkage of the building blocks of the poly (meth) acrylates which carry the functional groups.
- the substances containing epoxide groups can be both aromatic and aliphatic compounds.
- Excellently suitable multifunctional epoxides are oligomers of epichlorohydrin, epoxy ethers of polyhydric alcohols (in particular ethylene, propylene and butylene glycols, polyglycols, thiodiglycols, glycerol, pentaerythritol, sorbitol, polyvinyl alcohol, polyallyl alcohol and the like), epoxy ethers of polyhydric bisphenols [in particular resine bisphenols [especially resine phenol hydroquinone - (4-hydroxyphenyl) methane, bis (4-hydroxy-3-methylphenyl) methane, bis (4-hydroxy-3,5-dibromophenyl) methane, bis (4-hydroxy-3,5- difluorophenyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis (4-hydroxy-3-methylphenyl) propane , 2,2-bis (4-hydroxy-3-chloroph
- Very suitable ethers are, for example, 1,4-butanediol diglycidyl ether, polyglycerol 3-glycidyl ether, cyclohexanedimethanol diglycidyl ether, glycerol triglycidyl ether, neopentylglycol diglycidyl ether.
- crosslinking system a crosslinker-accelerator system
- the crosslinking agent-accelerator system comprises at least one substance containing epoxy groups as the crosslinking agent and at least one substance which acts as an accelerator at a temperature below the melting temperature of the polymer to be crosslinked for crosslinking reactions by means of compounds containing epoxy groups.
- amines are particularly preferably used as accelerators (formally to be understood as substitution products of ammonia; in the formulas below, these substituents are represented by “R” and in particular include alkyl and / or aryl radicals and / or other organic radicals), particularly preferably such amines, which do not or only slightly react with the building blocks of the polymers to be crosslinked.
- both primary (NRH2), secondary (NR2H) and tertiary amines (NR 3 ) can be selected as accelerators, of course also those which have several primary and / or secondary and / or tertiary amine groups.
- Multifunctional amines such as diamines, triamines and / or tetramines can also advantageously be used as accelerators.
- Amino alcohols are also preferably used as accelerators.
- Secondary and / or tertiary amino alcohols are particularly preferably used, where in the case of several amine functionalities per molecule, preferably at least one, preferably all, amine functionalities are secondary and / or tertiary.
- accelerators are pyridine, imidazoles (such as 2-methylimidazole) and 1, 8-diazabicyclo [5.4.0] undec-7-ene. Cycloaliphatic polyamines can also be used as accelerators. Phosphate-based accelerators such as phosphines and / or phosphonium compounds such as triphenylphosphine or tetraphenylphosphonium tetraphenylborate are also suitable.
- Acrylate PSAs are typically free-radically polymerized copolymers of acrylic acid alkyl esters or methacrylic acid alkyl esters of C1 to C20 alcohols, such as, for example, methyl acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, 2 Ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, iso octyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, tetradecyl (meth) acrylate, lauryl (meth) acrylate, Oleyl (meth) acrylate, palmityl (meth) acrylate and stearyl (meth) acrylate
- esters of ethylenically unsaturated di- and tricarboxylic acids and anhydrides such as ethyl maleate, dimethyl fumarate and ethyl methyl itaconate.
- Vinylaromatic monomers such as styrene, vinyltoluene, methylstyrene, n-butylstyrene and decylstyrene are also included.
- vinyl esters of carboxylic acids containing up to 20 carbon atoms such as vinyl acetate or vinyl laurate
- vinyl ethers of alcohols containing up to 10 carbon atoms such as vinyl methyl ether or vinyl isobutyl ether
- vinyl halides such as vinyl chloride or vinylidene dichloride
- nitriles such as acrylonitrile or methacrylonitrile
- acid amides and acrylates or unsaturated acrylates or methacrylamides with 2 to 8 carbon atoms such as ethylene, propene, butadiene, isoprene, 1-hexene or 1-octene.
- polyfunctional ethylenically unsaturated monomers can be used as crosslinking monomers.
- these are divinylbenzene, alkyl diacrylates such as 1, 2-ethylene glycol diacrylate, 1, 4-butanediol diacrylate, 1, 6 hexanediol, 1, 8-octanediol or 1, 12-dodecane diol diacrylate, triacrylates such as trimethylolpropane triacrylate and tetra erythritoltetraacrylat as penta-.
- the group of polyfunctional monomers also includes UV-crosslinkable monomers, such as derivatives of benzophenone or benzoin functionalized with (meth) acrylate.
- Another group of monomers are those which generate a latent crosslinking potential in the polymer and spontaneously (often catalyzed) lead to a network structure after the adhesive has dried.
- a monomer is, for example, glycidymethyl acrylate, whose oxirane ring with hydroxyl or, in particular, carboxylate functions leads to a covalent bond with ring opening. This reaction takes place accelerated in Presence of zinc ions or, especially in the presence of carboxyl functions, amines instead.
- the processing temperature of the adhesive must be above its glass transition temperature in order to have viscoelastic properties.
- activatable adhesive compositions based on acrylate according to the invention can be used.
- the activatable adhesive compositions then consist in a particularly preferred embodiment of a base polymer a) consisting of a1) 40 to 95% by weight of acrylic acid ester and / or methacrylic acid ester with the following
- a4 0 to 20% by weight of a copolymerizable vinyl monomer which, with the functional group, can contribute to increasing cohesion, increasing the reactivity of the crosslinking, or to direct crosslinking, and
- the polymer a) can comprise an activatable pressure-sensitive adhesive which becomes pressure-sensitive under the action of temperature and optional pressure and, after the bonding and cooling, builds up a high adhesive strength due to the solidification.
- these activatable PSAs have different static glass transition temperatures TG, A or a melting point TS, A.
- acrylic monomers are used for the monomers a1) which comprise acrylic and methacrylic acid esters with alkyl groups consisting of 4 to 14 C atoms, preferably 4 to 9 C atoms.
- alkyl groups consisting of 4 to 14 C atoms, preferably 4 to 9 C atoms.
- Specific examples are n-butyl acrylate, n-pentyl acrylate, n- Hexyl acrylate, n-heptyl acrylate, n-octyl acrylate, n-nonyl acrylate, lauryl acrylate, stearyl acrylate, behenyl acrylate, and their branched isomers, such as 2-ethylhexyl acrylate.
- Further classes of compound to be used which can also be added in small amounts under c1), are methyl methacrylates, cyclohexyl methacrylates, isobornyl acrylate and isobornyl methacrylates
- it is used as monomers a2) itaconic acid, acrylic acid, methacrylic acid, vinyl acetic acid, fumaric acid, crotonic acid, aconitic acid, dimethylacrylic acid, ⁇ -acryloyloxypropionic acid, trichloracrylic acid, vinylphosphonic acid, vinylsulfonic acid and vinylsulfonic acid.
- the monomers a3) used are glycidyl methacrylate, maleic anhydride and itaconic anhydride.
- vinyl esters, vinyl ethers, vinyl halides, vinylidene halides, vinyl compounds with aromatic cycles and heterocycles in the a position are used for the monomers a4).
- vinyl acetate, vinylformamide, vinylpyridine, ethylvinylether, vinylchloride, vinylidene chloride and acrylonitrile are used for the monomers a4).
- monomers with the following functional groups are used: hydroxyl, acid amide, isocyanato or amino groups.
- component a4) are hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, allyl alcohol, acrylamide, benzyl acrylate, benzyl methacrylate, phenyl acrylate, phenyl methacrylate, t-butyl phenyl acrylate, t-butylaphenyl methoxy acrylate, phenyl methacrylate methacrylate, Butoxyethyl acrylate, dimethylaminoethyl methacrylate, dimethylaminoethyl acrylate, diethylaminoethyl methacrylate, diethylaminoethyl acrylate, cyanoethyl methacrylate, cyanoethyl acrylate, 6-hydroxyhexyl methacrylate, N-tert-butylacrylamide, N-methylol methacrylate
- aromatic vinyl compounds are used for component a4), the aromatic nuclei preferably being from C4 to C18 exist and can also contain heteroatoms.
- Particularly preferred examples are styrene, 4-vinylpyridine, N-vinylphthalimide, methylstyrene, 3,4-dimethoxystyrene, 4-vinylbenzoic acid, although this list is not exhaustive.
- the monomers are in turn chosen such that the resulting polymers can be used as industrially usable adhesives or PSAs, in particular in such a way that the resulting polymers have adhesive or pressure-sensitive adhesive properties in accordance with the "Handbook of Pressure Sensitive Adhesive Technology" by Donatas Satas (1989) have.
- the control of the desired glass transition temperature can be achieved by using the Fox equation (G1) when compiling the monomer mixture which is the basis of the polymerization.
- the static glass transition temperature of the resulting polymer is advantageously below 15 ° C.
- the monomers are very preferably selected in accordance with what has been said above, and the quantitative composition of the monomer mixture is advantageously chosen such that, according to the Fox equation ( G1) (cf. TG Fox, Bull. Am. Phys. Soc. 1 (1956) 123) gives the desired Tc , A value for the polymer.
- n represents the running number of the monomers used
- w n the mass fraction of the respective monomer n (% by weight)
- Tc the respective glass transition temperature of the homopolymer from the respective monomers n in K.
- radical polymerizations are preferably used which additionally contain further radical initiators for the polymerization, in particular thermally decomposing radical-forming azo or peroxo initiators.
- thermally decomposing radical-forming azo or peroxo initiators are suitable.
- all the usual initiators known to those skilled in the art for acrylates are suitable.
- the production of C-centered radicals is described in Houben Weyl, Methods of Organic Chemistry, Vol. E 19a, pages 60 to 147. These methods are preferably used in analogy.
- radical sources are peroxides, hydroperoxides and azo compounds
- typical radical initiators are potassium peroxodisulfate, dibenzoyl peroxide, cumene hydroperoxide, cyclohexanone peroxide, di-t-butyl peroxide, azodiisoic acid butyronitrile, cyclohexyl peroxyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxetyl peroxyl peroxyl peroxyl peroxide tetraperyl peroxide tetraperyl tetra peroxyl peroxo
- the average molecular weights M n of the PSAs formed in the radical polymerization are very preferably chosen such that they are in a range from 20,000 to 2,000,000 g / mol; PSAs with average molecular weights M n of 100,000 to 500,000 g / mol are produced specifically for further use as hotmelt PSAs.
- the polymerization can be carried out in bulk, in the presence of one or more organic solvents, in the presence of water or in mixtures of organic solvents and water.
- the aim is to keep the amount of solvent used as low as possible.
- the polymerization time is between 4 and 72 hours.
- the self-adhesive used can be mixed with one or more additives such as plasticizers, fillers, pigments, UV absorbers, sunscreens, anti-aging agents, crosslinking agents, crosslinking promoters or elastomers.
- additives such as plasticizers, fillers, pigments, UV absorbers, sunscreens, anti-aging agents, crosslinking agents, crosslinking promoters or elastomers.
- Other adhesive resins can also be used, the use of adhesive resins according to the invention being preferred.
- Suitable fillers and pigments are, for example, carbon black, titanium dioxide, calcium carbonate, zinc carbonate, zinc oxide, silicates or silica.
- Suitable plasticizers are, for example, aliphatic, cycloaliphatic and aromatic mineral oils, di- or poly-esters of phthalic acid, trimellitic acid or adipic acid, liquid rubbers (for example nitrile or polyisoprene rubbers), liquid polymers from butene and / or isobutene, acrylic acid esters, polyvinyl ether, liquid and soft resins based on the raw materials for adhesive resins, wool wax and other waxes or liquid silicones.
- Crosslinking agents are, for example, phenolic resins or halogenated phenolic resins, melamine and formaldehyde resins.
- Suitable crosslinking promoters are, for example, maleimides, allyl esters such as triallyl cyanurate, polyfunctional esters of acrylic and methacrylic acid.
- the present invention also relates to a PSA tape comprising at least one layer of the PSA of the invention.
- adheresive tape pressure-sensitive adhesive tape
- adheresive tape pressure-sensitive adhesive tape
- adheresive tape pressure-sensitive adhesive tape
- encompasses all flat structures such as foils or foil sections expanded in two dimensions, tapes with extended length and limited width, tape sections and the like, and ultimately also Die cuts or labels.
- the adhesive tape thus has a longitudinal dimension (x direction) and a width dimension (y direction).
- the adhesive tape also has a thickness (z direction) running perpendicular to both dimensions, the width and length dimensions being many times greater than the thickness.
- the thickness is as similar as possible, preferably exactly the same, over the entire area of the adhesive tape determined by length and width.
- Suitable adhesive tapes according to the invention thus comprise single-layer and multi-layer adhesive tapes.
- Adhesive tapes according to the invention which are coated on one or both sides with adhesives, are usually wound into a roll in the form of an Archimedean spiral at the end of the production process.
- the adhesive is covered with a covering material (also referred to as a release material) before the adhesive tape is wrapped.
- a covering material also referred to as a release material
- Such covering materials are known to the person skilled in the art under the names Releaseliner or Liner.
- liners are also used to cover labels.
- a liner (release paper, release film) is not part of a PSA strip, but only an aid for its manufacture, storage and / or for further processing by punching.
- a liner unlike a (permanent) adhesive tape carrier, a liner is not firmly attached to an adhesive layer, so that it is also referred to as a temporary carrier.
- the liners also ensure that the adhesive is not contaminated before use.
- the type and composition of the release materials can be used to adjust the liner so that the adhesive tape can be unwound with the desired force (light or heavy).
- the liners additionally ensure that the correct side of the adhesive is uncovered when it is unrolled.
- Adhesives can be produced in solvent-based or solvent-free processes, by means of liquid coating, extrusion or other suitable processes.
- the coating takes place in one or more work steps, including coextrusion or multi-layer nozzle coating, or lamination.
- either the actual liner material itself can already be anti-adhesive, or it can be coated on at least one side, preferably on both sides, with an anti-adhesive coating, for example siliconized.
- all sheet-like layers that can be suitably separated from the adhesive tape are included, for example also those with their own pressure-sensitive adhesive.
- Paper or film carriers are typically used as liners, which are equipped on one or in particular on both sides with an adhesive coating compound (also referred to as a adhesive or anti-adhesive compound) in order to reduce the tendency of adhesive products to adhere to these surfaces (separating function).
- Liners for self-adhesive tapes are often based on biaxially or monoaxially stretched polypropylene, on polyethylene or other polyolefins, on paper or on polyester.
- a multitude of different substances can be used as adhesive coating compositions, which are also called release coatings: waxes, fluorinated or partially fluorinated compounds, carbamate lacquers and in particular silicones and various copolymers with silicone components.
- silicones have become widely used as release materials in the field of adhesive tape due to their good processability, low costs and the broad property profile.
- structured liners or liners with fillers or other particulate substances or particles in or on the surface, or liners consisting of or coated with other suitable separating layers or coatings, can be used as liners.
- carriers which, depending on which side the adhesive layer is applied, act as a temporary carrier (liner) or as a permanent carrier (i.e. carrier in the sense of the application). If a carrier has only a single anti-adhesive surface, while the opposite surface is not anti-adhesive (for example a PET carrier siliconized on one side), it acts as a liner when the adhesive layer is applied to the anti-adhesive surface, while it acts as a liner when the adhesive layer is applied the non-adhesive surface acts as a carrier.
- a carrier has only a single anti-adhesive surface, while the opposite surface is not anti-adhesive (for example a PET carrier siliconized on one side), it acts as a liner when the adhesive layer is applied to the anti-adhesive surface, while it acts as a liner when the adhesive layer is applied the non-adhesive surface acts as a carrier.
- At least one layer of a self-adhesive composition is always present. This layer can have a thickness of 15 to 5000 pm, preferably 50 to 3000 pm, more preferably 100 pm to 2000 pm, more preferably 150 pm to 2000 pm, even more preferably 400 to 1500 pm, in particular 1000 to 1200 pm, such as 500 to 800 pm. Additional layers, such as further adhesive layers, may be contained in the pressure-sensitive adhesive strip. In addition, non-sticky layers, which are to be understood in particular as little stretchable (£ max ⁇ 100%) or stretchable (£ max at least 100%) carrier layers, can be contained in the adhesive tape.
- any carrier present is preferably a carrier film, for example made of polypropylene, polyethylene or polyester.
- elastic carriers are preferably used, such as, for example, a viscoelastic acrylate foam which is foamed, for example, with microballoons.
- the acrylic foam can also contain hollow glass spheres.
- the softening point was measured using an R&B (Ring & Ball) softening point measuring device from Herzog HRB 754.
- the softening point was measured according to the standard measuring program ASTM E28 / EN1427.
- Static glass transition temperature T g melting temperature, softening temperature
- Glass transition points - synonymously referred to as glass transition temperatures - in particular of polymers or polymer blocks are given as the result of measurements by means of dynamic differential calorimetry DDK (English Dynamic Scanning Calorimetry; DSC) according to DIN 53 765, in particular sections 7.1 and 8.1, but with uniform heating and cooling rates of 10 K / min in all heating and cooling steps (compare DIN 53 765; section 7.1; note 1).
- the sample weight is 20 mg. Also the The melting temperature or softening temperature of polymers or polymer blocks is determined in this way.
- Tables 2 and 3 summarize the results of a storage test of two different terpene phenolic resins. The characterization was done via softening point measurement.
- 53-carene-based terpene-phenolic resins show better stability in the aging process than a-pinene-based terpene-phenolic resins, even at softening points below 110 ° C.
- 53-Carene-based terpene phenol resins have stable physical properties after prolonged room temperature storage.
- terpenphenol resins according to the invention are less stable in storage:
- Example 1 A 53-carene-based terpene phenol resin was subjected to thermal stress. The resin was stored in a drying cabinet at 40 ° C for 3 weeks. The softening point was checked at weekly intervals. The results are shown in the following table.
- FIG. 2 The associated GPC of the a-pinene-based terpene phenol with R&B 95 ° C is shown in Fig. 2.
- Figure 3 shows the GPC curves for the resin of Example 1 compared to the resin of Example 2 superimposed. The shift in the maximum of the low molecular weight peak can be clearly seen.
- a 53-carene-based terpene phenol with a higher softening point was subjected to thermal stress.
- the resin was stored in a drying cabinet at 40 ° C for 3 weeks.
- the softening point was checked at weekly intervals. The results are shown in the following table.
- FIG. 5 The associated GPC of the a-pinene-based terpene phenol with R&B 105 ° C is shown in Fig. 5.
- Figure 6 shows the GPC curves for the resin of Example 3 (a-pinene based) compared to the resin of Example 4 (53-carene based) superimposed. The shift in the maximum of the low molecular weight peak can be clearly seen.
- the a-pinene and 53-carene-based resins differ in the storage and intensity of the low molecular weight peak. This difference is due to a difference in the physical characteristics of the resins.
- the softening points were determined over a defined storage period. It has been shown that the 53-carene-based terpene phenol resin shows better aging behavior.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102019200211 | 2019-01-10 | ||
PCT/EP2020/050115 WO2020144126A1 (de) | 2019-01-10 | 2020-01-06 | Verwendung von thermisch stabilen terpenphenolharzen |
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EP20700426.8A Pending EP3908618A1 (de) | 2019-01-10 | 2020-01-06 | Verwendung von thermisch stabilen terpenphenolharzen |
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US (1) | US12043767B2 (de) |
EP (1) | EP3908618A1 (de) |
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Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2307836A1 (fr) | 1975-04-16 | 1976-11-12 | Derives Resiniques Terpenique | Procede de preparation de resines terpene-phenol |
US5457175A (en) * | 1995-01-11 | 1995-10-10 | Arizona Chemical Company | Low softening point terpene-phenol resins |
US7199204B2 (en) * | 2002-05-07 | 2007-04-03 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesive composition |
DE10323617A1 (de) * | 2003-05-26 | 2004-12-23 | Clariant Gmbh | Schmelzklebemassen |
DE102007016950A1 (de) | 2007-04-05 | 2008-10-09 | Tesa Ag | Thermisch vernetzende Polyacrylate und Verfahren zu deren Herstellung |
DE102009054788A1 (de) * | 2009-12-16 | 2011-06-22 | tesa SE, 20253 | Verfahren zur Stabilisierung von Polyacrylathaftklebemassen in Abmischung mit Klebharzen |
DE102013211628A1 (de) | 2013-06-20 | 2014-12-24 | Tesa Se | UV-vernetzbare, harzmodifizierte Klebemasse |
DE102013212345A1 (de) | 2013-06-26 | 2014-12-31 | Tesa Se | Polare Klebharze für niederenergetischer Oberflächen |
-
2020
- 2020-01-06 US US17/421,848 patent/US12043767B2/en active Active
- 2020-01-06 WO PCT/EP2020/050115 patent/WO2020144126A1/de unknown
- 2020-01-06 EP EP20700426.8A patent/EP3908618A1/de active Pending
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