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United States Patent Office Patented Dec 3,60,601 United States Patent Office Patented Dec. 3, 1964 2 fied by oxygen atoms attached to other silicon atoms to 3,60,601 form siloxane linkages, monovalent hydrocarbon radicals, AMNE SALTS OF PHOSPHORIC ACED AND AANE SALS OF CAR30XYECAC AS hydrocarbon radicals which are polyvalent, i.e. which SLANO, CONDENSATON CATALYSTS have a valence higher than one, each valence of which James Franklia Hyde, Midland, Mich, assigaor ig Bow is attached to another silicon atom to form silcarbane Corning Corporation, Midland, Mich., a corporation linkages and similar monovalent and polyvalent hydro of Michigan carbon radicals containing such functions as ether link No Drawing. Filed July 3, 1959, Ser. No. 826,421 ages, aromatic halogen atoms, aliphatic fluorine atoms, 7. Caimas. (C. 260-46.5) hydroxyl groups and nitrile groups. Any aliphatic fluo 0 line atoms should be separated from any silicon atom This invention relates to the use of amine salts as by at least three carbon atoms. catalysts for the condensation of silicon-bonded hydroxyl More specifically, the silicon valences of the organe groups. silicon compound employed in this invention can be The condensation of silicon-bonded hydroxyl groups Satisfied by, for example, any alkyl radical such as the employing as catalysts alkali metal and quaternary am 5 Inethyl, ethyl, isopropyl, tert-butyl, 2-ethylhexyl, dodecyl, Inonium hydroxides and organosilicon salts thereof is ccitadecyl and myricyl radicals; any alkenyl radical such now well known in the art. However, these catalysts have as the vinyl, allyl and hexadienyl radicals; any cycloalkyl a primary disadvantage of breaking siloxane bonds causing radical such as the cyclopentyl and cyclohexyl radicals; random rearrangement of siloxane units in a polymer. any cycloalkenyl radical such as the cyclopentenyl and While this is not a problem where all the siloxane units 20 cylohexenyl radicals; any aryl hydrocarbon radical such are alike, it is undesirable where, for instance, there is as the phenyl, naphthyl and xenyl radicals; any aralkyl initially in a polymer a planned distribution of siloxane radical Slich as the benzyl, phenylethyl and xylyl radicals units containing functional groups. Rearrangement of and any alkaryl radical such as the tolyl and dimethyl such siloxane units may well reduce or negate the useful phenyl radicals. These monovalent hydrocarbon radicals ness of the functional groups. There has been a search can also contain aromatic halogen atoms as, for example, by those skilled in the art for a compound which would in the 2,4,6-trichlorobenzyl, perchlorophenyl, 2-bromo catalyze the condensation of silicon-bonded hydroxyl naphthyl, p-iodo-phenylethyl and 4-fluorophenyl radicals; groups in a polymer without attacking siloxane bonds aliphatic fluorine atoms as, for example, in the 3,3,3-tri and permitting unit rearrangement within the polymer. fluoropropyl, c.,a,c-trifluorotolyl, 3,3,4,4,5,5,5-heptafluoro The objects of this invention are primarily two-fold. 30 penty and 5,5,5-trifluoro-2-trifiuoromethylamyl radicals; The first object is to provide a new condensation catalyst hydroxyl radicals as, for example, in the 4-ethyl-4-hy for silicon-bonded hydroxyl groups. The second object droxyhexyl, 3-hydroxyallyl, cresy), p-hydroxyphenyl and is to provide such a condensation catalyst which is not a siloxane bond rearrangement catalyst. Other objects and advantages of this invention will become apparent 35 -CHCHK s >ot as the invention is explained. - radicals; nitrile radicals as, for example, in the gamma This invention relates to the method which comprises cyanopropyl and beta-cyanoethyl radicals and ether link condensation of silicon-bonded hydroxyl groups by con ages as, for example, in the -CHCHOCHCH, tacting (A) an organosilicon compound containing at least one silicon-bonded hydroxyl group per molecule, 40 any remaining silicon valences in said organo-silicon reno CCECE compound being satisfied by radicals selected from the -CH2(OCH2CH2)2OCH, -CHOCH2CH=CH and group consisting of silicon-bonded oxygen atoms, hydro furyl radicals. These radicals can contain more than one carbon radicals and hydrocarbon radicals containing func of the above functions in radicals such as, for example, tions selected from the group consisting of ether linkages, aromatic halogen atoms, nitrile groups, hydroxyl groups -CHCH-CHCHCHOHCHOCHs and aliphatic fluorine atoms, the last being separated from any silicon atom by at least three carbon atoms, with (B) -CH2CH2CH2O CH, CHOEICHk X a composition compatible with (A) and selected from the -CH2CH2OCFCF group consisting of (1) a salt of a phosphoric acid, the 50 only active hydrogen atoms in said acid being attached to the phosphorous through an oxygen atom, and a basic horroctor amino compound, any active hydrogen in said amino and compound being attached to nitrogen, and any remaining valences of the nitrogen atom in said amino compound 55 being satisfied by carbon atoms, the total number of car -C2CHCHO chschoichk Xci bon atoms in (1) being at least 18, and (2) a salt of a These silicon valences can also be satisfied by poly carboxylic acid, the only active hydrogen atoms in said Valent hydrocarbon radicais attached to other silicon acid being a part of carboxyl groups, and a basic amino atoms. These polyvalent hydrocarbon radicals can con compound, any active hydrogen in said amino compound 60 tain singly or in any combination such polyvalent groups being attached to nitrogen, and any remaining valences as methylene, vinylene, vinylidene, cyclohexylidene, phen of the nitrogen being satisfied by carbon atoms, the total - ylene, toylene, toluenyl, toluylene, tertiary carbon atoms, number of carbon atoms in (2) being at least 6, whereby and quaternary carbon atoms as well as any monovalent the silicon-bonded hydroxyl groups in (A) condense to hydrocarbon radicals. These polyvalent hydrocarbon form siloxane linkages producing water as a by-product. 65 radicais can contain the various functions permissible in The organosilicon compound can be any silane, siloxane the monovalent radicals as previously, described. Exam or silcarbane or any mixture thereof in which the only functional groups attached directly to any silicon atom pies of operative polyvalent hydrocarbon radicals contain are hydroxyl groups. The silicon valences not satisfied ing Such functions include - by hydroxyl groups can be satisfied by any groups which 70 -CH(OCH2CH3)6OCH, CHCH do not interfere with the condensation of silicon-bonded OH. hydroxyl groups. Thus the silicon valences can be satis -CH3CH, CH, CH, CHCHO CH 3,160,601 ?e 4. -CHCHCHFCH2CH2-, iodophenylene and allylamine, N-methylallylamine, amylamine, N,N-dimeth ylamylamine, aniline, p-bromoaniline, 2,6-dinitroaniline, B m-fluoroaniline, sym-bis-gamma-aminopropyl-tetramethyl disiloxane, gamma (N-aminoethylamino)propyldiphenyl -CHK XCH 5 methylsilane, o-iodoaniline, o-nitroaniline, 2,3,4,5-tetra Thus, where R represents any of the abovedescribed chloroaniline, o-anisidine, 9-anthrylamine, 4,4'-diamino monovalent radicals and R represents any of the above azobenzene, anthranilonitrile, benzylamine, p-methoxy described polyvalent radicals, the organosilicon compound benzylamine, decylamine, diallylamine, dicyclohexyl employed as a starting material can be, for example, any amine, diethylenetriannine, difurfurylamine, di-m-tolyl one or any combination of the following types of mono amine, 3-ethoxyethylamine, tetrahydrofurfurylamine, his meric compounds or can contain any of the specific types O tamine, benzylhydrazine, p-bromophenylhydrazine, 1 of the following polymer units: methyl-1-phenylhydrazine, 4,4'-diaminohydrazobenzene, RSiOH, RSiOH2, RSi(OH)3, R3SiO5, p-leucaniline, methylamine, morpholine, 5-nitronaphthyl R2SiO, RSiO5, SiO2, RSi(OH)Os, amine, 1,2-dimethyl-4-pentenylamine, N,N-diethyl-p- RSi(OH)O, RSiR'Si(OH), RSiR'SiROH, phenylenediamine, piperazine, piperidine, 2-aminopyri dine, 6-nitro-o-toluidine, 2-amino-p-tolunitrile, 9-phenan HORSiR'SiR (OH), Hors--SIROH thrylamine, and tribenzylamine. SiRO As state above the salts which are operative catalysts ORSiR'SiRO.5 and the like. in this invention are the reaction products of any of the In any one molecule of the organosilicon compound there 20 basic amino compounds described above, i.e. ammonia must be at least one silicon-bonded hydroxyl group. and primary, secondary and tertiary amines, both organic While the above list does not include all the possible and silylorganic, with either a phosphoric acid or a variations, it is sufficiently representative to show the carboxylic acid in which any carboxyl group is attached scope of the materials which can be employed in this to a carbon atom. As in the basic amino compounds invention. 25 where any active hydrogen atoms are attached to nitrogen The method of this invention is especially advantageous atoms, so in the acids any active hydrogen atoms must be for producing polysiloxane fluids, gums and resins. Hy a part of the particular acid group, e.g. droxy-endblocked linear molecules, i.e. diorganopolysi O oxanes, can be polymerized without bond rearrangement by the condensation of the terminai silicon-bonded hy 30 RCOOH, O=P(OH)3 or ROP (OH), droxyl groups. If organosilyl endblocking is desired, the An “active hydrogen' atom is one which forms methane necessary proportion of triorganosilanol or other organo when a compound containing said "active hydrogen' is silicon compound containing one silicon-bonded hydroxyl reacted with methyl magnesium iodide at room tempera
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