USRE14087E - Byros b - Google Patents
Byros b Download PDFInfo
- Publication number
- USRE14087E USRE14087E US RE14087 E USRE14087 E US RE14087E
- Authority
- US
- United States
- Prior art keywords
- phenol
- amin
- compound
- heating
- anhydroformaldehydeanilin
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 66
- 238000000034 method Methods 0.000 description 30
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- -1 formaldehyde compound Chemical class 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- 239000000463 material Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LHGVFZTZFXWLCP-UHFFFAOYSA-N Guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 241000736839 Chara Species 0.000 description 2
- 229960001867 Guaiacol Drugs 0.000 description 2
- 229940079877 Pyrogallol Drugs 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- LKAJKIOFIWVMDJ-IYRCEVNGSA-N Stanazolol Chemical compound C([C@@H]1CC[C@H]2[C@@H]3CC[C@@]([C@]3(CC[C@@H]2[C@@]1(C)C1)C)(O)C)C2=C1C=NN2 LKAJKIOFIWVMDJ-IYRCEVNGSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- 239000006104 solid solution Substances 0.000 description 2
Definitions
- My invention relates to a process for making a certain composition of matter whlch i may he used either for molding into shapes or dissolved in an' appropriate solvent as a coating or varnish.
- a reac-- tion takes place with the formation of useful products varying among themselves according to the particular phenol and amin employed.
- I can take -ord1- nary phenol C l-LOH and heat it With anhydroformaldehydeanilin. There is produced a soft resinous mass, which becomes progressively harder on further heating.
- phenol and anhydroformaldehydeanilin in their natural state they can be used in solution, and by heating such solution a condensation product can be formed.
- the reaction between phenol and anhydroformaldehydeanilin seems to start before heat is applied, as even in the cold it phenol is added to anhydro'lformaldchydeanilin, which is a solid, the entire mass liqucfics.
- Anilin is liberated during the reaction and this can, if desired, be entirely or partly removed by suitable means at the proper stage, thus giving a harder resin. No special apparatus need be used to bring about the reaction as it takes place by heating in an open vessel.
- the compound can be dissolved in proper solvents, such as acetone, and used for a Varnish.
- proper solvents such as acetone
- the proportions in which the ingredients are mixed will. vary according to the particular phenol and other ing'g'redient used, and the most suitable proportionfor each case can be best determined by experiment.
- the process may he described as causing a reaction between a phenolic body and a body containing a reactive methylene group combined with a second group, which combination, by yielding ,forinaldehydeanili n.
- two amins as examples to show that notthe' methylene group to the phenol, brings about the formation of a substance of low volatility, non-miscible with water, low in electricalconductivity and capableof entering into solid. soluti n in the product.
- a compound having the qualities specified may be readily produced by heating together one part, by molecular weight, of carbolic acid with one part, by molecularweight, of (for instance) anhydroforn'ialdehydeanilin. These proportions are'based upon the formula for anhydroformaldehydeanilin given CJL N CH in the work of Dr. Hugo Erdman entitled A'nlcitmzg zm' Darstelhmg Org/anabol c? Chem [sober Prepamzfe, 1894, page 126.
- anhydroformaldehydeanilin should be used with three molecular weights of phenol.
- This reaction can be carried out with the formaldehyde compounds of the mains of the fatty as well as the aromaticseries.
- Methyl amin and anilin are the first members of each series.
- the formaldehyde compound of methyl amin is methylmethylene amin and the formaldehyde compound of anilin is anhydro- I have chosen these withstanding the great diii'erence between them, methyl amin being a gas and anilin a liquid, the formaldehyde compound of each is suitable for the reaction.
- manner I can use the formaldehyde compound of other amins such as ethyl amin, propyl amin, toluidin, xylidin, etc.
- any amin which is In the same v liberatedduring the reaction can be partly or entirely removed at the proper stage, and it is sometimes desirable to remove it and sometimes not, depending upon the properties desired in the final product.
- the process of producing an artificial resin WlllCil consists 1n causing a phenol to react upon anhydroformaldehydeanilin While heating the combined materials, and continuing the process until a definitely resinous mass is produced.
Description
BYRON B. GOLiDSMI'IH, OF NEW YORK, N. Y.
PROCESS OF MAKING LPLASTIC COMP OSITIONS.
Specification of Reissued Letters Patent. IR -issued plan 14, 1916 No llrawing. Original No. 1,168,626, dated January 18, 1916, Serial No. 741,158, Application for reissue filed February 5, 1916. Serial No. 76,479.
To all whom it may concern Be it known that I, Brno): B. GOLDSMITH,
v a citizen of the United States, residing at the invention, such as will enable others skilled in the art to which it appertains to make and use the same.
My invention relates to a process for making a certain composition of matter whlch i may he used either for molding into shapes or dissolved in an' appropriate solvent as a coating or varnish. I have discovered that on heating together a-phenol with the formaldehyde compound of an amin, a reac-- tion takes place with the formation of useful products varying among themselves according to the particular phenol and amin employed. As an example: I can take -ord1- nary phenol C l-LOH and heat it With anhydroformaldehydeanilin. There is produced a soft resinous mass, which becomes progressively harder on further heating. Instead of using phenol and anhydroformaldehydeanilin in their natural state they can be used in solution, and by heating such solution a condensation product can be formed. The reaction between phenol and anhydroformaldehydeanilin seems to start before heat is applied, as even in the cold it phenol is added to anhydro'lformaldchydeanilin, which is a solid, the entire mass liqucfics. Anilin is liberated during the reaction and this can, if desired, be entirely or partly removed by suitable means at the proper stage, thus giving a harder resin. No special apparatus need be used to bring about the reaction as it takes place by heating in an open vessel.
The compound can be dissolved in proper solvents, such as acetone, and used for a Varnish. The proportions in which the ingredients are mixed will. vary according to the particular phenol and other ing'g'redient used, and the most suitable proportionfor each case can be best determined by experiment.
Where anhydroi ormaldchydeanilin or its equivalent is employed, the process may he described as causing a reaction between a phenolic body and a body containing a reactive methylene group combined with a second group, which combination, by yielding ,forinaldehydeanili n. two amins as examples to show that notthe' methylene group to the phenol, brings about the formation of a substance of low volatility, non-miscible with water, low in electricalconductivity and capableof entering into solid. soluti n in the product.
I have found that a compound having the qualities specified may be readily produced by heating together one part, by molecular weight, of carbolic acid with one part, by molecularweight, of (for instance) anhydroforn'ialdehydeanilin. These proportions are'based upon the formula for anhydroformaldehydeanilin given CJL N CH in the work of Dr. Hugo Erdman entitled A'nlcitmzg zm' Darstelhmg Org/anabol c? Chem [sober Prepamzfe, 1894, page 126. If the formula be assumed as (C,,II,N:CH,),, then one molecular weight of anhydroformaldehydeanilin should be used with three molecular weights of phenol. This reaction can be carried out with the formaldehyde compounds of the mains of the fatty as well as the aromaticseries. Methyl amin and anilin are the first members of each series. The formaldehyde compound of methyl amin is methylmethylene amin and the formaldehyde compound of anilin is anhydro- I have chosen these withstanding the great diii'erence between them, methyl amin being a gas and anilin a liquid, the formaldehyde compound of each is suitable for the reaction. manner I can use the formaldehyde compound of other amins such as ethyl amin, propyl amin, toluidin, xylidin, etc.
It is to be understood that in the claims wherever a phenol is called for, the expression is intended to cover not only ordinary phenol, but other phenols such as guaiacol, resorcin, alpha and beta naphthol, 'pyrogallol, and in fact any compound oi this chara'cter which has the property of uniting with the methylene group of the compound formed by reacting upon an 21min with formaldehyde. On heating the compounds formed as above described, they become harder and more insol uble, and they are well adapted for molding under heat and pressure, with or without the admixture of other substances, as is well understood in the art, and in "fact, they can be put to all the uses which such substances have been found adapted to.
'As mentioned above, any amin which is In the same v liberatedduring the reaction can be partly or entirely removed at the proper stage, and it is sometimes desirable to remove it and sometimes not, depending upon the properties desired in the final product.
My claims for the compound itself in solution or otherwise are embodied in certain divisional applications, and are therefore not set forth herein, this patent being confined to claims for the process itself. These claims for the compound are independent of the particular process usedin producing it and of whether or notithe lay-products (such as liberated amins) are incorporated.
I claiml. lhe process of producing an artificial resin Which consists "in causing a phenol to react upon a definite formaldehyde compound of an amin While heating the combined materials, and continuing the process until a definitely resinous mass is produced. 2. The process at producing an artificial resin Which consists in causing carbohc acid to react upon a, definite formaldehyde compound of an amin While heating the combined materials, and continuing the process until a definitely resinous mass isproduced.
3. The process of producing an artificial resin WlllCil consists 1n causing a phenol to react upon anhydroformaldehydeanilin While heating the combined materials, and continuing the process until a definitely resinous mass is produced.
4. The process of producing an artificial resin which consists in causing carbolic acid to react upon anhydroformaldehydeanilin While heating the combined materials, and continuing the process until a definitely resinous mass is produced.
5. The processof producing an artificial resin Which consists in causing a phenol to react upon anhydroformaldehydeanilin in the presence of heat, separating the anilin produced in the reaction from the remainder of the mass, and continuing the process until a definitely resinous mass is produced.
6. The process of preparing phenolic condensation products, which consists in reacting upon a phenolic body with a body containing a reactive methylene group combined With another group which after yield-" ing the methylene group to the phenolic body engenders a substance characterized by a low degree of volatility, non-miscibility with Water, low electrical conductivity, and
in the product.
i B. B. GOLDSMITH.
the capacity for entering into solid solution,
Family
ID=
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