US3766086A - Polyisocyanurate biuret surfactants - Google Patents

Polyisocyanurate biuret surfactants Download PDF

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Publication number
US3766086A
US3766086A US00157236A US3766086DA US3766086A US 3766086 A US3766086 A US 3766086A US 00157236 A US00157236 A US 00157236A US 3766086D A US3766086D A US 3766086DA US 3766086 A US3766086 A US 3766086A
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US
United States
Prior art keywords
biuret
positive integer
groups
polyisocyanurate
isocyanurate
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 - Lifetime
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US00157236A
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English (en)
Inventor
P Argabright
C Wenger
C Presley
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Marathon Oil Co
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Marathon Oil Co
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Assigned to MARATHON OIL COMPANY, AN OH CORP reassignment MARATHON OIL COMPANY, AN OH CORP ASSIGNS THE ENTIRE INTEREST Assignors: MARATHON PETROLEUM COMPANY
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    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/06—Protein or carboxylic compound containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07—Organic amine, amide, or n-base containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
    • Y10S516/914—The agent contains organic compound containing nitrogen, except if present solely as NH4+

Definitions

  • the present invention relates generally :to the eld of isocyanurate-containing organic compounds generally classified within Class 260, subclasses -248 and 88.3 of the United States Patent Office.
  • the present invention relates to a new class of compounds which ⁇ are useful as emulsifying agents, e.g., .in forming dspersions and emulsions. These compounds are characterized by containing in :a single molecule all of the following groups:
  • the compounds of the present invention have th-e general structure shown in FIG. 1;
  • R divalent hydrocarbon or substituted hydrocarbon radical, as described below land exemplified in FIG. 2.
  • X a metal, or hydrogen or quaternary ammonium (which, for the purposes of this invention, acts like a metal) or a 'combination thereof.
  • Particularly preferred are hydrogen, quaternary ammonium and metals selected from the following groups of the Periodic Table; Ia, Ib, Ha, IIb, IIIa, IIIb, IVa, IVb, Va, Vb, Vla; including such meals as Li, Na, K, Rb, Cs, Ca, Ag, Au, Be, Mg, Ca, Sr, Ba, Ra, Zn, Cd, Hg, B, Al, Sc, Y, La, land the other rare earths, Ac, Ga, In, T1, Ti, Zr, Hf, Ge, Sn, Pb, V, Nb, Ta, Sb, Bi, Cr, Mo, W, Mn, Fe, Ru, Co, Ni, Rh, Pd, Os, and Ir.
  • A a monovalent organic radical selected from the following: isocyanate urethane (NHCO'2R), urea (--NHCONHR'), amino (-NH2), NHR' or NR2)
  • R monova1ent hydrocarbon or substituted hydrocarbon radical, as discussed below;
  • m-a averfage number of trisubstituted isocyanurate rings and is a positive integer from 0 to about 400, and most preferably from 0 to about 200.
  • n-b average number of isocyanuric acid and/or isotcyanurate salt groups 'and is a positive integer from 1 to about 10,000, more preferably from 2 to about 1000, and most preferably from 3 to about 100.
  • 2m+n+1 average number of divalent R groups and is a positive integer from 2 to about 11,000, more preferably from 3 to about 1,100 and most preferably from 4 to about 140.
  • 2 average number of A groups and is a positive integer from 2 to about 2000, more preferably from 2 to about 400 and most preferably from 2 to about 200;
  • R preferably contains 2 to 40, more preferably 2 to 30, and most preferably 2 to 18 carbon atoms.
  • R preferably contains 1 to 40 carbon atoms, more preferably 1 to 20 carbon atoms and most preferably 1 to 10 carbons, for example -CH3, -C2H5, -C3H7, i-C3H7,
  • CH3 CH2 CH-CHZ, @-01% ctc.
  • R may be hydrogen, lower alkyl (e.g., ethyl, hexyl) or aryl (e.g. monovalent radicals corresponding to the aryl radicals described in FIG. 2.
  • R shown in FIG. 2 are set forth for purposes of elucidation, not restriction.
  • the values of m and n described above are on the basis of the integers which will be used to describe a single molecule.
  • the invention will involve mixtures of molecules of the general form described above.
  • the average value of m-a for the mixture may be from about 1 to about 2000, more preferably from about 1 to 400, and most preferably from about 1 to 200
  • the average value of n-b may be from about 0.5 to 10,000, more preferably from about 0.5 to 1000, and most preferably from about 0.5 to 100
  • the value of a may be from about 0 to 2000, more preferably from to 400, and most preferably from 2 to 200.
  • the present invention relates to a new class of emulsifying agents, their preparation, and processes for their use.
  • the compounds of the present invention may be added to immiscible mixtures of water and organic compounds, e.g., equal parts by volume of water and a hydrocarbon and the resulting mixture agitated to form emulsions. This result is all the more surprising as many of the compounds are only very slightly soluble, and some are insoluble, in either phase.
  • FIG. 1 shows the general formula of the products of the present invention.
  • FIGS. 2 and 3 exemplify some of the possible structures of R groups of the starting materials and products of the present invention.
  • FIG. 4 shows the general formula of the organic starting materials of the present invention.
  • the starting materials for the present invention are salts of polyisocyanuric acids produced according to the techniques taught in copending U.S. patent application S.N. 715,199, led Mar. 22, 1968, now U.S. Pat. 3,573,- 259, by reacting a metal cyanate and an organic diisocyanate in the presence of an aprotic solvent to form isocyanurate-containing polyisocyanate metal salts.
  • Reaction media Water or mixtures of water and an alcohol, ketone, ester, amide, sulfoxide, sulfone, etc.
  • the lower limit is generally the freezing point of solution and the upper limit is generally the boiling point of the solution at the reaction pressure.
  • the reaction can be carried out at pressures of from 0.5 t0 100, with 0.6 to 50 being more preferred, and 0.7 to 10 atmospheres being most preferred.
  • T ime.-The reaction time is dependent on the initial concentration of the starting materials and the temperature.
  • the preferred time is from 0.01 to 4500 hours, more preferred 0.05 to 350 hours, and most preferred from 0.06 t0 200 hours.
  • a composition comprising a mixture of compounds 5 containing in a single molecular isocyanurate, metal isocyanurate and biuret groups, and having the structure:
  • o 0 R divalent hydrocarbon or substituted hydrocarbon H N CHa H N g CHa SoaH SOaCHa 0, g CE radical, containing 2 to about 40 carbon atoms, l l X is selected from the group consisting of metals, hy-
  • l l A is a monovalent organic radical selected from the group consisting of -NHCO2R, -NHCONHR',
  • n-b is the average number of isocyanurate acid and/0r isocyanurate salt groups and is a positive integer from 1 to about 10,000, wherein l l a is the average number of trisubstituted biuret groups,
  • mei-2 is the average number of A groups and is a positive integer from 2 to about 2,000, and wherein there are no N-to-N bonds and no A-to-N bonds, and no A-to-A bonds and no Rto-R bonds.
  • R is selected 45 CHP@ from the group of organic radicals consisting of:
  • compositions according to claim 1 wherein X is selected from the group consisting of hydrogen, quaternary ammonium radicals and metal radicals selected from the following groups of the Periodic Table; Ia, Ib, IIa, IIb, IIIa, IIIb, IVa, IVb, Va, Vla.
  • compositions according to claim 1 wherein R is selected from the group of organic radicals as shown below:
  • An emulsion comprising both Water and at least one cyclopropyl, -polymethylene -OCOR, compound according to claim 1.
  • c can, cHBcH-cn-CH3 CH2-wen cucmcr cuzcHZ-c'H-cmcnz 'eeeioa (WHERE HI F,C

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
US00157236A 1971-06-28 1971-06-28 Polyisocyanurate biuret surfactants Expired - Lifetime US3766086A (en)

Applications Claiming Priority (1)

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US15723671A 1971-06-28 1971-06-28

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US (1) US3766086A (it)
DE (1) DE2219162A1 (it)
FR (1) FR2143718B1 (it)
GB (1) GB1396161A (it)
IT (1) IT953644B (it)
NL (1) NL148603B (it)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3852100A (en) * 1972-12-26 1974-12-03 Marathon Oil Co Treatment of porous surfaces of articles of manufacture
US3920545A (en) * 1973-11-02 1975-11-18 Marathon Oil Co Ion exchange of metals from aqueous solutions
US4006098A (en) * 1972-02-09 1977-02-01 Marathon Oil Company Polyisocyanurate salt emulsifying agents and derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4408060C2 (de) * 1994-03-07 1996-02-08 Mannesmann Ag Vorrichtung an einem Hubtisch zum Ausziehen aus Regalfächern bzw. Einschieben in Regalfächer von Paletten, insbesondere von Tablaren

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006098A (en) * 1972-02-09 1977-02-01 Marathon Oil Company Polyisocyanurate salt emulsifying agents and derivatives
US3852100A (en) * 1972-12-26 1974-12-03 Marathon Oil Co Treatment of porous surfaces of articles of manufacture
US3920545A (en) * 1973-11-02 1975-11-18 Marathon Oil Co Ion exchange of metals from aqueous solutions

Also Published As

Publication number Publication date
FR2143718B1 (it) 1974-12-27
NL7208357A (it) 1973-01-02
DE2219162A1 (de) 1973-01-18
NL148603B (nl) 1976-02-16
GB1396161A (en) 1975-06-04
FR2143718A1 (it) 1973-02-09
IT953644B (it) 1973-08-10

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AS Assignment

Owner name: MARATHON OIL COMPANY, AN OH CORP

Free format text: ASSIGNS THE ENTIRE INTEREST IN ALL PATENTS AS OF JULY 10,1982 EXCEPT PATENT NOS. 3,783,944 AND 4,260,291. ASSIGNOR ASSIGNS A FIFTY PERCENT INTEREST IN SAID TWO PATENTS AS OF JULY 10,1982;ASSIGNOR:MARATHON PETROLEUM COMPANY;REEL/FRAME:004172/0421

Effective date: 19830420