WO1980001053A1 - Oil-modified resole compositions and laminates made therefrom - Google Patents
Oil-modified resole compositions and laminates made therefrom Download PDFInfo
- Publication number
- WO1980001053A1 WO1980001053A1 PCT/US1979/000990 US7900990W WO8001053A1 WO 1980001053 A1 WO1980001053 A1 WO 1980001053A1 US 7900990 W US7900990 W US 7900990W WO 8001053 A1 WO8001053 A1 WO 8001053A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- parts
- phenol
- weight
- mixture
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 229920003987 resole Polymers 0.000 title claims abstract description 21
- 239000003921 oil Substances 0.000 claims abstract description 25
- 235000019198 oils Nutrition 0.000 claims abstract description 25
- 239000000944 linseed oil Substances 0.000 claims abstract description 22
- 235000021388 linseed oil Nutrition 0.000 claims abstract description 21
- 239000002383 tung oil Substances 0.000 claims abstract description 18
- 239000002966 varnish Substances 0.000 claims abstract description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229920002866 paraformaldehyde Polymers 0.000 claims description 8
- 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 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
- 238000010030 laminating Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 229930003836 cresol Natural products 0.000 claims description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical group NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 239000003607 modifier Substances 0.000 abstract description 3
- 239000011101 paper laminate Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 7
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000123 paper Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 238000004080 punching Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000004431 Linum usitatissimum Nutrition 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 2
- 240000002834 Paulownia tomentosa Species 0.000 description 2
- 240000004543 Vicia ervilia Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- -1 phenol aldehyde Chemical class 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229920002522 Wood fibre Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/42—Layered products comprising a layer of synthetic resin comprising condensation resins of aldehydes, e.g. with phenols, ureas or melamines
-
- 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
- B32B29/00—Layered products comprising a layer of paper or cardboard
- B32B29/002—Layered products comprising a layer of paper or cardboard as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B29/005—Layered products comprising a layer of paper or cardboard as the main or only constituent of a layer, which is next to another layer of the same or of a different material next to another layer of paper or cardboard layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/12—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of paper or cardboard
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/32—Chemically modified polycondensates by organic acids or derivatives thereof, e.g. fatty oils
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/47—Condensation polymers of aldehydes or ketones
- D21H17/48—Condensation polymers of aldehydes or ketones with phenols
-
- 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
- B32B38/00—Ancillary operations in connection with laminating processes
- B32B38/04—Punching, slitting or perforating
- B32B2038/042—Punching
-
- 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
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/02—Composition of the impregnated, bonded or embedded layer
- B32B2260/028—Paper layer
-
- 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
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—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
- B32B2307/00—Properties of the layers or laminate
- B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
-
- 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
- B32B2311/00—Metals, their alloys or their compounds
- B32B2311/12—Copper
-
- 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
- B32B2317/00—Animal or vegetable based
- B32B2317/12—Paper, e.g. cardboard
- B32B2317/125—Paper, e.g. cardboard impregnated with thermosetting resin
Definitions
- This invention relates to oil-modified resole varnishes . More particularly, the invention relates to such varnishes which are prepared using lins eed oil alone or in combination with tung oil or oiticica oil as the modifier for the resole and to laminates prepared using varnishes containing the resoles as impregnants.
- linseed oil is a mixtur e of triglycerid es, is olates by crushing and solvent extraction of flax s eed, comprising typically 6% palmitic, 3. 5% stearic, 20% oleic, 14.5% linoleic and 56% linoleic glycerides, with a Wijis iodine value of 180-195.
- the linoleic moiety is the non-conjugated isomer of the conjugated elaeostearic glyceride present in tung oil.
- drying oils such as linseed oil, perilla oil, tung oil or mixtures thereof may be used in combination with phenolic resins to make hardboard with enhanced physical strength and moisture resistance.
- the drying oil component of the Dorland et al system is not used to modify the phenolic resin, but rather is used to impregnate the surface of the hardboard after the resin has been used to coat the wood fibers for consolidation under heat and pressure.
- Mention is also made of the teachings of Ellis in The Chemistry of Synthetic Resins, Vol. I, Reinhold Publ.
- footnote 69 which refers to an abstract of German Patent No. 534, 784.
- the abstract describes solid resinous products formed by heat reacting linseed or wood oil with phenols, cresols, etc. , and then with formaldehyde in the presence of bases. In essence, it has been discovered that linseed oil can replace
- paper laminates prepared from the new varnishes have improved properties, especially punchability after thermal aging.
- laminating varnishes by a process comprising preparing an oil-modified resole by (a) reacting a phenol moiety with a drying oil comprising (i) from about 20 to about 100 parts by weight of linseed oil and (ii) from about 80 to about 0 parts by weight of tung oil, oiticica oil or a mixture thereof in a presence of a strong acid and (b) reacting the product of (a) in an alcohol solvent with an aldehyde moiety in the presence of an amine catalyst.
- the linseed oil comprises from 40 to 60 parts by weight and the tung oil compris es from 60 to 40 parts by weight of the drying oil.
- resoles can be carried out conventionally.
- phenol, cresol, cresylic acid or mixtures thereof in any proportion are combined with a concentrated acid such as sulfuric acid or phosphoric acid and heated to a temperature of approximately 35oC. , there then being added over a suitable period the drying oil, the amounts of ingredients being such that the acid constitutes, by weight, from about 0.3 to 1 percent of the total mixture and the drying oil constitutes, by weight, from about 15 to 40 percent of the total mixture, the remainder being the phenol moiety.
- the mixture of the phenol, acid and oil is heated at a temperature of from about 70oC. to about 250°C. , preferably 115oC.
- methyl alcohol in the amount of about 9 parts by weight is used for each 100 parts by weight of resole reaction product.
- paraformaldehyde is used as the aldehyde moiety, it will be realized that other non-water-containing aldehydes can be used, such as methyl and propyl forme els, which are s olutions of formaldehyde in the corresponding methyl or propyl alcohol.
- Formaldehyde as such is not preferred since it contains water, the excess of which then has to be removed.
- the linseed oil is preferably raw or alkali refined. Description of the Preferred Embodiments . - The following examples illustrate the present invention, but are not to be construed to limit the claims in any manner whatsoever. All parts are by weight.
- EXAMPLE 1 After a mixture of 1400 g. of synthetic phenol (Allied Chemic and 14.1 g. of reagent grade concentrated sulfuric acid (98% pure) is heated to 120oC. under nitrogen, 874 g. of raw linseed oil is added in one portion. The reaction mixture is then heated to 160 ⁇ 2oC. , and this temperature is maintained for one hour. After the mixture is allowed to cool to 75 oC. , 586 g. of 2-propanol is added. This addition is followed by one of 32 g. of ethylene diamine. The reaction is stir red for 5 minutes and then 640 g. of paraformaldehyde (92% pure) is added.
- EXAMPLE 4 A mixture of 1125 parts of phenol, 325 parts of cresylic acid, and 14.1 parts of concentrated sulfuric acid is heated with stirring to 120oC. At this temperature, 656 parts of raw linseed oil is added and the temperature is maintained between 120o C. and 130oC. for 1. 0 hours . At this point, 218 parts of tung oil is added at 124o C. and the reaction mixture is stirred for 0. 25 hours, then it is cooled. When the temperature of the reaction mixture reaches 65oC , 586 parts of 2-propanol is added. This addition is followed by one of 30 parts of ethylene diamine.
- cotton linters paper webs are impregnated with the resins of Examples 2-4 and dried in an over to a predetermined resin flow.
- Several plies of the impregnated paper are stacked, covered with copper foil, and pressed between stainless steel pans at high temperature and pressure. This results in paper based laminates with excellent room temperature punching and good electrical properties.
- EXAMPLE 5 The varnish of Example 3, 1190 parts, is combined with 20 parts of triphenyl phosphate, and 60 parts of antimony trioxide as flame retardant materials along with about 100 parts of a barium hydrate-catalyzed phenol-formaldehyde resin of low viscosity to facilitate penetration of the paper along with about 220 parts of an epoxy resin prepared from tetrabromobisphenol-A having a molecular weight of about 1100 and enough acetone (3 to 30 parts) to adjust the viscosity.
- EXAMPLE 6 To a mixture of 1125 g. of synthetic phenol, 325 g. of mp-90 cresol, and 16. 9 of sulfuric acid is added at 125o C. , 454 g. of alkali refined linseed oil. The reaction mixture is heated to 160 C. and this temperature is maintained for 0. 5 hours. After 0. 5 hours at 160o C. , the reaction mixture is cooled to 150oC. and 454 g. of tung oil is added. The reaction mixture is stirred at 140-150oC. for 15 minutes, then cooled at 70 oC. A mixture of 417 g. of methanol and 232 g. of
- Laminates with XXXP characteristics are prepared from this resin, and they have acceptable properties .
- the present invention provides resole materials which are readily made from economical and available oils.
- resole varnishes as impregnants.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1979901650 DE18995T1 (de) | 1978-11-20 | 1979-11-19 | Oelmodifizierte resol-zusammensetzungen und daraus hergestellte laminate. |
| BR7908924A BR7908924A (pt) | 1978-11-20 | 1979-11-19 | Aperfeicoamento no processo de preparacao de verniz de laminacao de resol modificado com oleo e laminado resultante |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96202478A | 1978-11-20 | 1978-11-20 | |
| US962024 | 1978-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1980001053A1 true WO1980001053A1 (en) | 1980-05-29 |
Family
ID=25505332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1979/000990 WO1980001053A1 (en) | 1978-11-20 | 1979-11-19 | Oil-modified resole compositions and laminates made therefrom |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0018995A4 (enrdf_load_stackoverflow) |
| JP (1) | JPS55500908A (enrdf_load_stackoverflow) |
| WO (1) | WO1980001053A1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03713A (ja) * | 1989-05-29 | 1991-01-07 | Hitachi Chem Co Ltd | フェノール樹脂及びフェノール樹脂積層板の製造法 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744013A (en) * | 1952-05-09 | 1956-05-01 | Rodger M Dorland | Artificial board |
| NL7214280A (enrdf_load_stackoverflow) * | 1971-12-04 | 1973-06-06 | ||
| JPS4924252A (enrdf_load_stackoverflow) * | 1972-07-03 | 1974-03-04 | ||
| US3920594A (en) * | 1973-07-04 | 1975-11-18 | Mitsubishi Gas Chemical Co | Resin composition for laminates |
| JPS51109966A (ja) * | 1975-03-25 | 1976-09-29 | Sumitomo Bakelite Co | Denkizetsuenyosekisobanno seizoho |
| US4043954A (en) * | 1975-03-27 | 1977-08-23 | General Electric Company | Compositions and laminates made therefrom |
| US4043970A (en) * | 1975-11-24 | 1977-08-23 | Monsanto Company | Resole resin binder composition |
| US4109057A (en) * | 1976-05-24 | 1978-08-22 | Sumitomo Durez Company, Ltd. | Method for accelerated curing of phenolic resin adhesives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE497790C (de) * | 1926-03-31 | 1930-05-15 | Bakelite Ges M B H | Verfahren zur Herstellung benzol- und oelloeslicher synthetischer Harze aus Phenolenund Aldehyden |
| FR1233589A (fr) * | 1959-04-29 | 1960-10-12 | Alsthom Cgee | Nouveaux vernis, notamment utilisables pour l'émaillage des conducteurs électriques |
| US4158650A (en) * | 1977-08-04 | 1979-06-19 | Mitsui Toatsu Chemicals, Inc. | Process for producing modified phenolic resin |
-
1979
- 1979-11-19 WO PCT/US1979/000990 patent/WO1980001053A1/en unknown
- 1979-11-19 JP JP50210779A patent/JPS55500908A/ja active Pending
-
1980
- 1980-06-16 EP EP19790901650 patent/EP0018995A4/en not_active Withdrawn
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744013A (en) * | 1952-05-09 | 1956-05-01 | Rodger M Dorland | Artificial board |
| NL7214280A (enrdf_load_stackoverflow) * | 1971-12-04 | 1973-06-06 | ||
| JPS4924252A (enrdf_load_stackoverflow) * | 1972-07-03 | 1974-03-04 | ||
| US3920594A (en) * | 1973-07-04 | 1975-11-18 | Mitsubishi Gas Chemical Co | Resin composition for laminates |
| JPS51109966A (ja) * | 1975-03-25 | 1976-09-29 | Sumitomo Bakelite Co | Denkizetsuenyosekisobanno seizoho |
| US4043954A (en) * | 1975-03-27 | 1977-08-23 | General Electric Company | Compositions and laminates made therefrom |
| US4043970A (en) * | 1975-11-24 | 1977-08-23 | Monsanto Company | Resole resin binder composition |
| US4109057A (en) * | 1976-05-24 | 1978-08-22 | Sumitomo Durez Company, Ltd. | Method for accelerated curing of phenolic resin adhesives |
Non-Patent Citations (1)
| Title |
|---|
| ELLIS, THE CHEMISTRY OF SYNTHETIC RESINS, VOLUME I, REINHOLD PUBLICATION 1935, PAGE 402. * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0018995A4 (en) | 1981-03-27 |
| EP0018995A1 (en) | 1980-11-26 |
| JPS55500908A (enrdf_load_stackoverflow) | 1980-11-06 |
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