RU2017123770A - Отверждаемые составы для ламинирующих адгезивов - Google Patents
Отверждаемые составы для ламинирующих адгезивов Download PDFInfo
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- RU2017123770A RU2017123770A RU2017123770A RU2017123770A RU2017123770A RU 2017123770 A RU2017123770 A RU 2017123770A RU 2017123770 A RU2017123770 A RU 2017123770A RU 2017123770 A RU2017123770 A RU 2017123770A RU 2017123770 A RU2017123770 A RU 2017123770A
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- polyester
- terminal
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- glycol
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- 239000012939 laminating adhesive Substances 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 title claims 2
- 229920000728 polyester Polymers 0.000 claims 33
- 239000000203 mixture Substances 0.000 claims 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid group Chemical group C(CCCCC(=O)O)(=O)O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N azelaic acid group Chemical group C(CCCCCCCC(=O)O)(=O)O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid group Chemical group C(CCCCCCCCC(=O)O)(=O)O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical group OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical group OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 2
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 claims 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims 2
- 239000001361 adipic acid Substances 0.000 claims 2
- 235000011037 adipic acid Nutrition 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical group O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical group OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000001530 fumaric acid Substances 0.000 claims 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical group OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical group OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- 239000011976 maleic acid Substances 0.000 claims 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical group OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 2
- -1 phthalamide anhydride Chemical group 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical group OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical group OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004386 diacrylate group Chemical group 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229960002479 isosorbide Drugs 0.000 claims 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- 229920001225 polyester resin Polymers 0.000 claims 1
- 239000004645 polyester resin Substances 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical group OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims 1
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4246—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof polymers with carboxylic terminal groups
- C08G59/4269—Macromolecular compounds obtained by reactions other than those involving unsaturated carbon-to-carbon bindings
- C08G59/4276—Polyesters
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
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- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
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- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
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- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Claims (30)
1. Отверждаемый состав, содержащий
a) смесь, содержащую
i) сложный полиэфир с концевыми эпоксидными группами, имеющий структуру
где R- выбран из группы, состоящей из
где n равен 1-25,
и где сложное полиэфирное звено выбрано из группы, состоящей из сложного полиэфира с концевой карбоновой кислой и сложного полиэфира с концевой дикарбоновой кислотой; и по меньшей мере один из
ii) малеатного сложного (поли)эфира, имеющего структуру, выбранную из группы, состоящей из
и
iii) олигомера или полимера с концевым диакрилатом, имеющего структуру
где R’ представляет собой радикал диола, полиэтиленгликоля, полипропиленгликоля, сложного полиэфира или полиуретана, и b) отверждающий агент на основе алифатического амина.
2. Состав по п. 1, отличающийся тем, что сложное полиэфирное звено выбрано из группы, состоящей из сложного полиэфира с концевой адипиновой кислотой, сложного полиэфира с концевой азелаиновой кислотой, сложного полиэфира с концевой себациновой кислотой, сложного полиэфира с концевой янтарной кислотой, сложного полиэфира с концевой фумаровой кислотой, сложного полиэфира с концевой малеиновой кислотой, сложного полиэфира с концевой 1,4-циклогександикарбоновой кислотой, сложного полиэфира с концевой ортофталевой кислотой, сложного полиэфира с концевой изофталевой кислотой, сложного полиэфира с концевой терефталевой кислотой, сложного полиэфира с концевым этиленгликолем, сложного полиэфира с концевым диэтиленгликолем, сложного полиэфира с концевым пропиленгликолем, сложного полиэфира с концевым дипропиленгликолем, сложного полиэфира с концевым 1,4-бутандиолом, сложного полиэфира с концевым 2-метил-1,3-пропандиолом, сложного полиэфира с концевым неопентилгликолем, сложного полиэфира с концевым 1,6-гександиолом, сложного полиэфира с концевым 1,4-циклогександиметанолом, сложного полиэфира с концевым 1,3-циклогександиметанолом, сложного полиэфира с концевым триэтиленгликолем, сложного полиэфира с концевым триметилолэтаном, сложного полиэфира с концевым триметилолпропаном, сложного полиэфира с концевым глицерином, сложного полиэфира с концевым фталевым ангидридом и сложного полиэфира с концевым малеиновым ангидридом.
3. Состав по п. 1 или 2, отличающийся тем, что сложная полиэфирная смола с эпоксидной концевой группой имеет эпоксидную эквивалентную массу от 242 до 1200.
4. Состав по любому из предшествующих пунктов, отличающийся тем, что сложное полиэфирное звено имеет кислотное число от 100 до 250.
5. Состав по любому из предшествующих пунктов, отличающийся тем, что малеатный сложный (поли)эфир представляет собой малеиновый ангидрид, сополимеризованный с дикарбоновой кислотой и/или ангидридом и гликолем.
6. Состав по п. 5, отличающийся тем, что дикарбоновая кислота выбрана из группы, состоящей из адипиновой кислоты, азелаиновой кислоты, себациновой кислоты, янтарной кислоты, фумаровой кислоты, малеиновой кислоты, 1,4-циклогександикарбоновой кислоты и ортофталевой кислоты, и гликоль выбран из группы, состоящей из этиленгликоля, диэтиленгликоля, пропиленгликоля, дипропиленгликоля, 1,4-бутандиола, 2-метил-1,3-пропандиола, неопентилгликоля, 1,6-гександиола, 1,4-циклогександиметанола, 1,3-циклогександиметанола, триэтиленгликоля, изосорбида, триметилолэтана, триметилолпропана и глицерина.
7. Состав по любому из предшествующих пунктов, отличающийся тем, что алифатический амин является производным соединения, выбранного из группы, состоящей из этилендиамина, диэтилентриамина, триэтилентетрамина, тетраэтиленпентамина, пиперазина, аминоэтилпиперазина, изофорондиамина, ксилилендиамина и их комбинаций.
8. Состав по любому из предшествующих пунктов, отличающийся тем, что алифатический амин имеет молекулярную массу по меньшей мере 750 а.е.м.
9. Состав по любому из предшествующих пунктов, отличающийся тем, что смесь a) и алифатический амин b) представлены в соотношении смешивания от 100: 15,0.
10. Состав по любому из предшествующих пунктов, дополнительно содержащий растворитель.
11. Состав по п. 10, отличающийся тем, что растворитель выбран из группы, состоящей из этилацетата, метилэтилкетона, метилацетата, ацетона и их комбинаций.
12. Состав по любому из пп. 1-9, отличающийся тем, что указанный состав по существу не содержит растворителя.
13. Ламинирующий адгезив, полученный из состава по любому из предшествующих пунктов.
14. Ламинирующий адгезив по п. 13, отличающийся тем, что указанный ламинирующий адгезив имеет прочность клеевого соединения от 1,5 до 5,0 Н/15 мм и рабочую вязкость ≤6500 мПа⋅с при 50°С.
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| AR102914A1 (es) * | 2014-11-12 | 2017-04-05 | Dow Global Technologies Llc | Adhesivo de laminación por embutición en frío de bisfenol-a-libre |
| EP3504258B1 (en) * | 2016-08-25 | 2022-10-05 | Stepan Company | Polyester-epoxide polymer compositions |
| JP2020510725A (ja) | 2017-03-02 | 2020-04-09 | ステパン カンパニー | イソシアネート修飾ポリエステル−エポキシドポリマー組成物 |
| BR112019019333B1 (pt) | 2017-03-31 | 2022-11-08 | Stepan Company | Composição polimérica de poliéter-epóxido, processo para a preparação da mesma e revestimento, elastômero, elastômero microcelular, adesivo e selante compreendendo dita composição |
| JP6934536B2 (ja) * | 2017-05-15 | 2021-09-15 | ダウ グローバル テクノロジーズ エルエルシー | 水性接着剤組成物 |
| ES3036836T3 (en) | 2018-12-19 | 2025-09-24 | Stepan Co | One-component adhesive compositions |
| US12441832B2 (en) | 2019-07-15 | 2025-10-14 | Arkema France | Isocyanate-free laminating adhesive |
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| US3272647A (en) * | 1962-03-23 | 1966-09-13 | Du Pont | Epoxy terminated polyester complexes, coating compositions containing same and metal ubstrates coated therewith |
| US3816365A (en) * | 1968-09-12 | 1974-06-11 | Ciba Geigy Ag | Adducts,containing epoxide groups,from polyglycidyl compounds and acid polyesters of aliphatic-cycloaliphatic dicarboxylic acids,process for their manufacture and use |
| US3836485A (en) * | 1972-02-24 | 1974-09-17 | Dow Chemical Co | Solid epoxy resins from glycidyl ethers of hydrogenated bisphenols or hydrogenated novolacs and aromatic or cycloaliphatic dicarboxylic acids |
| CH588513A5 (ru) * | 1973-12-19 | 1977-06-15 | Ciba Geigy Ag | |
| JPS51101100A (ja) * | 1975-03-05 | 1976-09-07 | Toa Gosei Chem Ind | Kokaseijushisoseibutsu |
| US4051195A (en) * | 1975-12-15 | 1977-09-27 | Celanese Polymer Specialties Company | Polyepoxide-polyacrylate ester compositions |
| US4547562A (en) | 1984-03-26 | 1985-10-15 | Gus Nichols | Solventless polymeric composition comprising non arylamine, polyacrylate and epoxide |
| US4675374A (en) | 1984-03-26 | 1987-06-23 | Gus Nichols | Solventless polymeric composition reaction product of (1) adduct of amine and acrylate with (2) polyacrylate |
| US5969046A (en) | 1986-11-18 | 1999-10-19 | Rohm And Haas Company | Reacting methylene and alkene components in presence of tertiary amine reacted with epoxide |
| JPH0751614B2 (ja) * | 1987-08-11 | 1995-06-05 | 東洋紡績株式会社 | 高分子量改質ポリエステルの製造方法 |
| EP0305331A3 (de) * | 1987-08-25 | 1991-05-08 | Ciba-Geigy Ag | Epoxidflexibilisatoren |
| DE3825754A1 (de) | 1988-07-29 | 1990-02-01 | Huels Chemische Werke Ag | Waessrige zweikomponentensysteme auf epoxidbasis und diaminen |
| EP0722964A1 (de) * | 1994-12-22 | 1996-07-24 | Ciba-Geigy Ag | Epoxidgruppenterminierte Polyester enthaltendes Epoxidharzgemisch |
| JPH09165494A (ja) | 1995-11-16 | 1997-06-24 | Yuka Shell Epoxy Kk | 硬化性エポキシ樹脂組成物およびその使用 |
| US20020006484A1 (en) | 1998-05-20 | 2002-01-17 | Balasubramaniam Ramalingam | Adhesive and coating formulations for flexible packaging |
| US6986948B2 (en) * | 2002-10-21 | 2006-01-17 | Ashland, Inc. | Polyester-based dimethacrylates designed for laminating applications |
| US20050137357A1 (en) | 2003-12-18 | 2005-06-23 | Skoglund Michael J. | Epoxy adhesive composition method of preparing and using |
| US20070088145A1 (en) | 2005-10-19 | 2007-04-19 | Mgaya Alexander P | Adhesive useful for film laminating applications |
| US20070173602A1 (en) * | 2006-01-25 | 2007-07-26 | Brinkman Larry F | Encapsulated Michael addition catalyst |
| US20080081883A1 (en) | 2006-09-28 | 2008-04-03 | Battelle Memorial Institute | Polyester Polyols Derived From 2,5-Furandicarboxylic Acid, and Method |
| US20120142816A1 (en) * | 2006-11-20 | 2012-06-07 | Dow Global Technologies Inc | Novel epoxy hardeners with improved cure and polymers with enhanced coating properties |
| CN101182405B (zh) * | 2007-12-13 | 2011-09-14 | 华南理工大学 | 一种双组分水性聚氨酯胶粘剂的制备方法 |
| AR098269A1 (es) * | 2013-11-18 | 2016-05-18 | Rohm & Haas | Poliéster terminado en epoxi |
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| EP3237484B1 (en) | 2018-12-26 |
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| TR201903954T4 (tr) | 2019-04-22 |
| CN107001896A (zh) | 2017-08-01 |
| TWI706017B (zh) | 2020-10-01 |
| US20170369634A1 (en) | 2017-12-28 |
| US10975192B2 (en) | 2021-04-13 |
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