CA1051016A - Preparation of aqueous dispersions of blocked aromatic polyisocyanates - Google Patents
Preparation of aqueous dispersions of blocked aromatic polyisocyanatesInfo
- Publication number
- CA1051016A CA1051016A CA227,573A CA227573A CA1051016A CA 1051016 A CA1051016 A CA 1051016A CA 227573 A CA227573 A CA 227573A CA 1051016 A CA1051016 A CA 1051016A
- Authority
- CA
- Canada
- Prior art keywords
- resorcinol
- dispersion
- formaldehyde
- blocked
- phenolic compound
- 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
- 239000006185 dispersion Substances 0.000 title claims abstract description 33
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 20
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 32
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002989 phenols Chemical class 0.000 claims abstract description 19
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- 229920000126 latex Polymers 0.000 claims abstract description 12
- 229920001971 elastomer Polymers 0.000 claims abstract description 11
- 229920000728 polyester Polymers 0.000 claims abstract description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 9
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 9
- 239000000758 substrate Substances 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 238000003618 dip coating Methods 0.000 claims description 5
- -1 aromatic isocyanate Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003945 anionic surfactant Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 10
- 239000000853 adhesive Substances 0.000 abstract description 7
- 230000001070 adhesive effect Effects 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 3
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003021 water soluble solvent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000004816 latex Substances 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 101000837192 Drosophila melanogaster Teneurin-m Proteins 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 101100043658 Schizosaccharomyces pombe (strain 972 / ATCC 24843) ste11 gene Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical group [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2321/00—Characterised by the use of unspecified rubbers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacturing & Machinery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
- Laminated Bodies (AREA)
- Reinforced Plastic Materials (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/473,160 US3933677A (en) | 1974-05-24 | 1974-05-24 | Preparation of aqueous dispersions of blocked aromatic polyisocyanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051016A true CA1051016A (en) | 1979-03-20 |
Family
ID=23878446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA227,573A Expired CA1051016A (en) | 1974-05-24 | 1975-05-22 | Preparation of aqueous dispersions of blocked aromatic polyisocyanates |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3933677A (enExample) |
| JP (1) | JPS5831340B2 (enExample) |
| AU (1) | AU498669B2 (enExample) |
| BE (1) | BE829440A (enExample) |
| CA (1) | CA1051016A (enExample) |
| DE (1) | DE2522963C3 (enExample) |
| ES (1) | ES437912A1 (enExample) |
| FR (1) | FR2272158B1 (enExample) |
| GB (1) | GB1506240A (enExample) |
| IT (1) | IT1038412B (enExample) |
| SE (1) | SE423999B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3997592A (en) * | 1975-11-24 | 1976-12-14 | E. I. Du Pont De Nemours And Company | Preparation of aqueous dispersions of blocked aromatic polyisocyanates |
| US4462855A (en) * | 1982-06-28 | 1984-07-31 | Celanese Corporation | Process for bonding polyester reinforcement elements to rubber |
| US4477619A (en) * | 1982-10-08 | 1984-10-16 | The B. F. Goodrich Company | Preparation of fabric for bonding to rubber |
| DE3331407A1 (de) * | 1983-08-31 | 1985-03-14 | Helmut Fischer GmbH & Co Institut für Elektronik und Meßtechnik, 7032 Sindelfingen | Elektromagnetische mess-sonde |
| US4572863A (en) * | 1985-07-29 | 1986-02-25 | The Goodyear Tire & Rubber Company | Aqueous polyester/epoxy emulsion treatment for yarn, method of preparation and a rubber/cord composite |
| US4680346A (en) * | 1985-12-13 | 1987-07-14 | Ppg Industries, Inc. | Flexible primer composition and method of providing a substrate with a flexible multilayer coating |
| US5169555A (en) * | 1990-11-09 | 1992-12-08 | Morton International, Inc. | Pulp bleaching solution |
| US5296160A (en) * | 1991-07-23 | 1994-03-22 | Miles Inc. | Aqueous dispersions of blocked polyisocyanates |
| GB2288179B (en) * | 1992-11-11 | 1997-06-11 | Jujo Paper Co Ltd | Aqueous polyolefin resin composition |
| US20040192876A1 (en) * | 2002-11-18 | 2004-09-30 | Nigel Hacker | Novolac polymer planarization films with high temparature stability |
| JP4426526B2 (ja) * | 2003-07-17 | 2010-03-03 | ハネウエル・インターナシヨナル・インコーポレーテツド | 最新式のマイクロエレクトロニクス用途およびデバイス用の平坦化膜およびそれらの製造方法 |
| MY148143A (en) * | 2006-03-03 | 2013-03-15 | Indspec Chemical Corp | Resorcinol-blocked isocyanate compositions and their applications |
| EP1971625A2 (en) * | 2006-03-03 | 2008-09-24 | Indspec Chemical Corporation | Resorcinol resin-blocked isocyanates and their applications |
| US20140027030A1 (en) * | 2012-07-30 | 2014-01-30 | Andreas Frantzen | Adhesive bonding for a pneumatic tire |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB975377A (en) * | 1961-11-03 | Goodyear Tire & Rubber | Adhesive composition comprising the reaction product of polyisocyanate and a formaldehyde condensate | |
| NL292181A (enExample) * | 1962-05-01 | |||
| US3234067A (en) * | 1962-11-05 | 1966-02-08 | Du Pont | Process for bonding rubber to polyester shaped structures |
| NL300680A (enExample) * | 1962-11-24 | 1900-01-01 | ||
| DE1299416B (de) * | 1963-04-02 | 1969-07-17 | Takeda Chemical Industries Ltd | Waessrige Klebstofldispersionen zum Verkleben von Kautschuk mit faserigen Materialien |
| US3454621A (en) * | 1965-06-17 | 1969-07-08 | Chrysler Corp | Preparation of blocked isocyanate adducts |
| US3489744A (en) * | 1966-07-18 | 1970-01-13 | Uniroyal Inc | Preparation of diisocyanate dimers in aqueous medium |
| US3668186A (en) * | 1970-04-17 | 1972-06-06 | Gen Tire & Rubber Co | Composition for lowering the release temperature of phenol- and lower alkyl substituted phenol-blocked isocyanates |
-
1974
- 1974-05-24 US US05/473,160 patent/US3933677A/en not_active Expired - Lifetime
-
1975
- 1975-05-21 FR FR7515774A patent/FR2272158B1/fr not_active Expired
- 1975-05-22 JP JP50060289A patent/JPS5831340B2/ja not_active Expired
- 1975-05-22 CA CA227,573A patent/CA1051016A/en not_active Expired
- 1975-05-23 BE BE156668A patent/BE829440A/xx not_active IP Right Cessation
- 1975-05-23 GB GB22798/75A patent/GB1506240A/en not_active Expired
- 1975-05-23 IT IT23701/75A patent/IT1038412B/it active
- 1975-05-23 SE SE7505906A patent/SE423999B/xx unknown
- 1975-05-23 AU AU81487/75A patent/AU498669B2/en not_active Expired
- 1975-05-23 ES ES437912A patent/ES437912A1/es not_active Expired
- 1975-05-23 DE DE2522963A patent/DE2522963C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU498669B2 (en) | 1979-03-22 |
| JPS5831340B2 (ja) | 1983-07-05 |
| SE7505906L (sv) | 1975-11-25 |
| GB1506240A (en) | 1978-04-05 |
| DE2522963B2 (de) | 1978-05-03 |
| SE423999B (sv) | 1982-06-21 |
| DE2522963A1 (de) | 1975-11-27 |
| US3933677A (en) | 1976-01-20 |
| DE2522963C3 (de) | 1978-12-21 |
| FR2272158B1 (enExample) | 1977-07-08 |
| IT1038412B (it) | 1979-11-20 |
| ES437912A1 (es) | 1977-04-16 |
| FR2272158A1 (enExample) | 1975-12-19 |
| AU8148775A (en) | 1976-11-25 |
| BE829440A (fr) | 1975-11-24 |
| JPS516944A (en) | 1976-01-20 |
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