CA1080600A - Production of laminates employing solvent-free adhesives - Google Patents
Production of laminates employing solvent-free adhesivesInfo
- Publication number
- CA1080600A CA1080600A CA264,852A CA264852A CA1080600A CA 1080600 A CA1080600 A CA 1080600A CA 264852 A CA264852 A CA 264852A CA 1080600 A CA1080600 A CA 1080600A
- Authority
- CA
- Canada
- Prior art keywords
- films
- molecular weight
- diisocyanate
- component
- bonded
- 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.)
- Expired
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 15
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000010408 film Substances 0.000 claims abstract description 49
- 239000010409 thin film Substances 0.000 claims abstract description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000011248 coating agent Substances 0.000 claims abstract description 7
- 238000000576 coating method Methods 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 238000003825 pressing Methods 0.000 claims abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical group O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 claims description 3
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical group O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 229920000570 polyether Polymers 0.000 abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 8
- 239000000306 component Substances 0.000 description 27
- -1 alkylene glycols Chemical class 0.000 description 21
- 239000012948 isocyanate Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- DOVJROOSBVOVCS-UHFFFAOYSA-N ethane-1,1,1,2,2-pentol Chemical compound OC(O)C(O)(O)O DOVJROOSBVOVCS-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 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 2
- 239000012939 laminating adhesive Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101100001675 Emericella variicolor andJ gene Proteins 0.000 description 1
- 235000011464 Pachycereus pringlei Nutrition 0.000 description 1
- 240000006939 Pachycereus weberi Species 0.000 description 1
- 235000011466 Pachycereus weberi Nutrition 0.000 description 1
- 240000002390 Pandanus odoratissimus Species 0.000 description 1
- 235000005311 Pandanus odoratissimus Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000001217 buttock Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- IZBNPGGKEWJZQN-UHFFFAOYSA-N ethane-1,1,1,2,2,2-hexol Chemical compound OC(O)(O)C(O)(O)O IZBNPGGKEWJZQN-UHFFFAOYSA-N 0.000 description 1
- MLTWWHUPECYSBZ-UHFFFAOYSA-N ethene-1,1,2-triol Chemical group OC=C(O)O MLTWWHUPECYSBZ-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/04—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving separate application of adhesive ingredients to the different surfaces to be joined
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin 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
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
-
- 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
- B32B2323/00—Polyalkenes
- B32B2323/04—Polyethylene
-
- 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
- B32B2367/00—Polyesters, e.g. PET, i.e. polyethylene terephthalate
-
- 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
- B32B2377/00—Polyamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2549371A DE2549371C3 (de) | 1975-11-04 | 1975-11-04 | Verfahren zur Herstellung von Verbundfolien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080600A true CA1080600A (en) | 1980-07-01 |
Family
ID=5960843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,852A Expired CA1080600A (en) | 1975-11-04 | 1976-11-04 | Production of laminates employing solvent-free adhesives |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS598211B2 (enExample) |
| AT (1) | AT355319B (enExample) |
| BE (1) | BE847966A (enExample) |
| CA (1) | CA1080600A (enExample) |
| CH (1) | CH606374A5 (enExample) |
| DE (1) | DE2549371C3 (enExample) |
| DK (1) | DK142350C (enExample) |
| FI (1) | FI64632C (enExample) |
| FR (1) | FR2330751A1 (enExample) |
| GB (1) | GB1547480A (enExample) |
| IT (1) | IT1068429B (enExample) |
| NL (1) | NL7611354A (enExample) |
| SE (1) | SE434518B (enExample) |
| ZA (1) | ZA766602B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2718615C2 (de) * | 1977-04-27 | 1985-12-12 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur Herstellung von Verbundfolien |
| DE4215608A1 (de) * | 1992-05-12 | 1993-11-18 | Huels Chemische Werke Ag | Mehrschichtiges Kunststoffrohr |
| DE4215609A1 (de) * | 1992-05-12 | 1993-11-18 | Huels Chemische Werke Ag | Thermoplastische Mehrschichtverbunde |
| DE19520732A1 (de) | 1995-06-07 | 1996-12-12 | Bayer Ag | Thermoplastische Polyurethan-Elastomere |
| TWI756219B (zh) * | 2016-05-10 | 2022-03-01 | 美商陶氏全球科技有限責任公司 | 包括胺引發之多元醇之雙組分無溶劑黏著劑組合物 |
| AR117147A1 (es) * | 2018-11-28 | 2021-07-14 | Dow Global Technologies Llc | Proceso para formar un laminado con adhesivo sin solvente |
| US20210332275A1 (en) * | 2018-12-21 | 2021-10-28 | Dic Corporation | Adhesive, laminated film, and method for producing laminated film |
| WO2020213433A1 (ja) * | 2019-04-19 | 2020-10-22 | 三井化学株式会社 | 接着剤キットおよび積層体の製造方法 |
-
1975
- 1975-11-04 DE DE2549371A patent/DE2549371C3/de not_active Expired
-
1976
- 1976-10-14 SE SE7611436A patent/SE434518B/xx unknown
- 1976-10-14 NL NL7611354A patent/NL7611354A/xx not_active Application Discontinuation
- 1976-10-14 DK DK463076A patent/DK142350C/da not_active IP Right Cessation
- 1976-10-14 FI FI762944A patent/FI64632C/fi not_active IP Right Cessation
- 1976-11-02 IT IT2894776A patent/IT1068429B/it active
- 1976-11-02 JP JP51131338A patent/JPS598211B2/ja not_active Expired
- 1976-11-03 FR FR7633053A patent/FR2330751A1/fr active Granted
- 1976-11-03 CH CH1386276A patent/CH606374A5/xx not_active IP Right Cessation
- 1976-11-03 AT AT813276A patent/AT355319B/de not_active IP Right Cessation
- 1976-11-03 GB GB45688/76A patent/GB1547480A/en not_active Expired
- 1976-11-03 ZA ZA766602A patent/ZA766602B/xx unknown
- 1976-11-04 BE BE172061A patent/BE847966A/xx not_active IP Right Cessation
- 1976-11-04 CA CA264,852A patent/CA1080600A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1547480A (en) | 1979-06-20 |
| IT1068429B (it) | 1985-03-21 |
| DK142350C (da) | 1981-03-16 |
| CH606374A5 (enExample) | 1978-10-31 |
| AT355319B (de) | 1980-02-25 |
| JPS5257269A (en) | 1977-05-11 |
| FI64632C (fi) | 1983-12-12 |
| FR2330751B1 (enExample) | 1979-03-02 |
| ATA813276A (de) | 1979-07-15 |
| JPS598211B2 (ja) | 1984-02-23 |
| SE7611436L (sv) | 1977-05-05 |
| DE2549371A1 (de) | 1977-05-12 |
| DE2549371B2 (de) | 1980-03-27 |
| FR2330751A1 (fr) | 1977-06-03 |
| ZA766602B (en) | 1977-10-26 |
| BE847966A (fr) | 1977-05-04 |
| DK142350B (da) | 1980-10-20 |
| DK463076A (da) | 1977-05-05 |
| SE434518B (sv) | 1984-07-30 |
| FI762944A7 (enExample) | 1977-05-05 |
| NL7611354A (nl) | 1977-05-06 |
| DE2549371C3 (de) | 1980-11-27 |
| FI64632B (fi) | 1983-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |