US3856895A - Phosphonamides - Google Patents

Phosphonamides Download PDF

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Publication number: US3856895A
Authority: US; United States
Prior art keywords: gms; alkyl; agitated; integer; formula
Prior art date: 1968-10-04
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

Application number

US00765001A

Other languages

English (en)

Inventor

L Schenck

J Beiswanger

F Eiseman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rhone Poulenc Surfactants and Specialties LP

Bayer CropScience Inc USA

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1968-10-04

Filing date

1968-10-04

Publication date

1974-12-24

1968-10-04 Application filed by Individual filed Critical Individual

1968-10-04 Priority to US00765001A priority Critical patent/US3856895A/en

1969-09-22 Priority to GB4660869A priority patent/GB1287915A/en

1969-09-24 Priority to DE19691948201 priority patent/DE1948201A1/de

1969-09-30 Priority to FR6933240A priority patent/FR2019897A1/fr

1969-10-02 Priority to CH1873769*A priority patent/CH542885A/de

1969-10-02 Priority to CH1486269A priority patent/CH514022A/de

1969-10-02 Priority to JP44079136A priority patent/JPS4813533B1/ja

1969-10-02 Priority to CH1486269D priority patent/CH1486269A4/xx

1969-10-03 Priority to NL6915032A priority patent/NL6915032A/xx

1969-10-03 Priority to BE739835D priority patent/BE739835A/xx

1974-12-24 Application granted granted Critical

1974-12-24 Publication of US3856895A publication Critical patent/US3856895A/en

1989-06-14 Assigned to CHASE MANHATTAN BANK, THE NATIONAL ASSOCIATION reassignment CHASE MANHATTAN BANK, THE NATIONAL ASSOCIATION SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DORSET INC. A CORP OF DELAWARE

1989-10-30 Assigned to GAF CHEMICALS CORPORATION reassignment GAF CHEMICALS CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE ON 04/11/1989 Assignors: DORSET INC.

1990-04-06 Assigned to RHONE-POULENC SPECIALTY CHEMICALS, L.P. reassignment RHONE-POULENC SPECIALTY CHEMICALS, L.P. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: GAF CHEMICALS CORPORATION

1990-10-30 Assigned to DORSET INC., A DE CORP. reassignment DORSET INC., A DE CORP. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE APRIL 10, 1989 Assignors: GAF CORPORATION, A DE CORP.

1991-01-22 Assigned to DORSET INC., reassignment DORSET INC., RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: CHASE MANHATTAN BANK, THE,

1991-05-30 Assigned to RHONE - POULENC SPECIALITY CHEMICALS reassignment RHONE - POULENC SPECIALITY CHEMICALS A CORRECTIVE ASSIGNMENT TO CORRECT THE SINGLE SERIAL NUMBER 07194,259 IDENTIFIED IN PREVIOUSLY RECORDED ASSIGMENT ON REEL 5315/FRAME 589. THIS CORRECTIVE ASSIGMENT SHOWS THAT THERE SHOULD HAVE BEEN A SCHEDULE ATTACHED. Assignors: GAF CHEMICALS CORPORATION

1991-06-24 Assigned to RHONE-POULENC SURFACTANTS AND SPECIALTIES INC. reassignment RHONE-POULENC SURFACTANTS AND SPECIALTIES INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE ON 05/03/1990 Assignors: RHONE-POULENC SPECIALTY CHEMICALS INC.

1991-12-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

125000005541 phosphonamide group Chemical group 0.000 title abstract description 20
150000001875 compounds Chemical class 0.000 claims description 14
239000002216 antistatic agent Substances 0.000 abstract description 16
125000000217 alkyl group Chemical group 0.000 abstract description 11
125000004432 carbon atom Chemical group C* 0.000 abstract description 11
150000001450 anions Chemical class 0.000 abstract description 5
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
239000001257 hydrogen Substances 0.000 abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract description 3
125000005037 alkyl phenyl group Chemical group 0.000 abstract description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
-1 polyethyleneoxy chlorophosphonates Polymers 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 18
239000000835 fiber Substances 0.000 description 11
239000000463 material Substances 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 9
229920004934 Dacron® Polymers 0.000 description 8
239000005020 polyethylene terephthalate Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000004677 Nylon Substances 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 6
239000012467 final product Substances 0.000 description 6
229920001778 nylon Polymers 0.000 description 6
229920002994 synthetic fiber Polymers 0.000 description 6
239000012209 synthetic fiber Substances 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000013256 coordination polymer Substances 0.000 description 5
150000008040 ionic compounds Chemical class 0.000 description 5
230000003068 static effect Effects 0.000 description 5
WNLWBCIUNCAMPH-UHFFFAOYSA-N 2-n,2-n-dimethylpropane-1,2-diamine Chemical compound NCC(C)N(C)C WNLWBCIUNCAMPH-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
230000001143 conditioned effect Effects 0.000 description 4
230000005611 electricity Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229920001155 polypropylene Polymers 0.000 description 4
150000003138 primary alcohols Chemical class 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000011877 solvent mixture Substances 0.000 description 4
238000007655 standard test method Methods 0.000 description 4
229920000742 Cotton Polymers 0.000 description 3
229920000297 Rayon Polymers 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000000034 method Methods 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
150000003333 secondary alcohols Chemical class 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
229920006397 acrylic thermoplastic Polymers 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
210000002268 wool Anatomy 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
ACUZDYFTRHEKOS-SNVBAGLBSA-N 2-Decanol Natural products CCCCCCCC[C@@H](C)O ACUZDYFTRHEKOS-SNVBAGLBSA-N 0.000 description 1
FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical compound CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 description 1
CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000792859 Enema Species 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000004020 conductor Substances 0.000 description 1
KUKQTFWICPUJBP-UHFFFAOYSA-N cyclohexanamine;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.NC1CCCCC1 KUKQTFWICPUJBP-UHFFFAOYSA-N 0.000 description 1
ACUZDYFTRHEKOS-UHFFFAOYSA-N decan-2-ol Chemical compound CCCCCCCCC(C)O ACUZDYFTRHEKOS-UHFFFAOYSA-N 0.000 description 1
ICEQLCZWZXUUIJ-UHFFFAOYSA-N decan-3-ol Chemical compound CCCCCCCC(O)CC ICEQLCZWZXUUIJ-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
OKDGZLITBCRLLJ-UHFFFAOYSA-N dodecan-3-ol Chemical compound CCCCCCCCCC(O)CC OKDGZLITBCRLLJ-UHFFFAOYSA-N 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
ADGQOCBSNYMAQS-UHFFFAOYSA-N hexadecan-6-ol Chemical compound CCCCCCCCCCC(O)CCCCC ADGQOCBSNYMAQS-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000011970 polystyrene sulfonate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000002964 rayon Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
HRDGAIGDKJXHIU-UHFFFAOYSA-N tetradecan-4-ol Chemical compound CCCCCCCCCCC(O)CCC HRDGAIGDKJXHIU-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
- D06M13/295—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing polyglycol moieties; containing neopentyl moieties
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials

Definitions

ABSTRACT Phosphonamide antistatic agents having the formula wherein R represents an alkyl phenyl, or alkylsubstituted phenyl radical having at least 7 carbon atoms, X represents hydrogen, methyl or ethyl, R and R are members of the group consisting of alkyl and hydroxy alkyl radicals of from 17-3 carbon atoms, R is a hydroxy al-kyl radical of from l-4 carbon atoms, Y is an anion, m is an integer of from l-IO, n is an integer of from 1-2, and p is an integer of from 12, and the sum of n p 3.
the instant invention relates to new and useful compositions of matter which function as antistatic agents when coated on-synthetic and natural fibers, e.g. polyester fibers, acetate rayons, wool, polyolefins, and the like, and to the method of use therefor.
the instant invention is directed to substituted phos phonamides which exhibit antistatic properties, which phosphonamides'are prepared by the condensation of alkyl and aryl polyethyleneoxy chlorophosphonates with a substituted alkyl diamine, followed by acidifi cation and alkoxylation.
antistatic agents function in two ways, both of which improve the electrical conductivity of the fiber surface.
Such antistatic agents are either reasonably good conductors of electricity themselves, or they are hygroscopic and help concentrate atmospheric moisture on the fibers.
antistatic agents fall into one of the following three categories: (I)' polyhydroxy and polyethyleneoxy non-ionic compounds; (2) cationic, or neutral nitrogenous compounds with a hydrophobic moiety in their structure; (3) long-chain phosphates, phosphonates, or other oxygenated phosphorus derivatives. Additional types include sulfonated oils and ester emulsions, and other fiber lubricant emulsions which depend on the particular emulsifying agent used for their antistatic effect.
Hygroscopic salts such as cyclohexylamine lactate
polyethoxylated fatty acids and alcohols as antistatic agents for polypropylenes as well as fibers, is reported in U.S. Pat. No. 2,525,691.
a further object of the present invention comprises the preparation of antistatic agents which have en-' hanced effectiveness with antistatic agents which contain an amide linkage and a polyalkoxylated hydr0- phobe.
Yet a further object of the instant invention is to prepare new and useful substituted phosphonamides which are derived from the chlorophosphonate of an alkoxylated primary or secondary alcohol or phenol and a substituted alkyl diamine.
Yet another object of the instant invention is to provide a process for the preparation of a new and useful antistatic agent, which processcomprises the condensation of alkyl and aryl polyethyleneoxy chlorophosphonates with a substituted alkyl diamine. followed by acidification and alkoxylation.
the new and useful antistatic agents ofthe instant invention correspond to the general formula:
R1 [RO o int mmm],1*-(N1I0mornorn-rvm X p wherein represents an alkyl phenyl or alkyl-substituted-phenyl radical containing at least 7 carbon atoms, X represents hydrogen, methyl orethyl, R, and R represent alkyl or hydroxy alkyl radicals having from 1-3 carbon atoms, R.-, is a hydroxy alkyl radical having from 1-4 carbon atoms.
Y is an anion, m is an integer of from 1-10, 11 is an integer of from l2 and p is an integer of from l2.
R may be exemplified, but is not limited to, the following alkyl, phenyl or alkaryl radicals:
Exemplary hydroxy alkyl radicals for R include:
Exemplary anions for Z include:
novel phosphonamides of the instant invention are prepared by the condensation of alkyl and aryl polyethyleneoxy chlorophosphonates with a substituted alkyl diamine followed by acidification and alkoxylation. More specifically, in our preferred synthesis, a commercial straight chain aliphatic alcohol admixture comprising approximately 5% C 25% C 30% C 30% C and C is reacted with an alkylene oxide using an alkaline catalyst at ll50C. and l psig until one to ten moles of the oxide is added. In place of the alkaline catalyst, acidic catalysts such as BF H PO and the like can be used.
Secondary alcohols such as 2 decanol, 3-decanol, 4'-decanol, 3- dodecanol, 4-tetradecanol, 6-hexadecanol, and the like or their admixtures as well as alkylphenols such as octylphenol, linear decyl phenol, branched dodecylphenol, etc, can be substituted for the primary aliphatic alcohol.
the resultant alkyl or alkyl-arylpolyalkyleneoxyalkanol is then reacted with phosphorous oxychloride to form the corresponding mono or di alkyl or alkylarylpolyalkyleneoxy chlorophosphonate and the latter compound converted to its phosphonamide by reaction with gamma dialkylaminopropylamine.
This latter derivative is acidified and reacted with an alkylene oxide to form its quaternary ammonium salt.
reaction lIl ltOll ulkylulm oxirlu catalyst
novel substituted amide produced by reaction lIl can then be quaternized by reaction with an alkylene oxide or hydroxy substituted alkylene oxide in the presence of an acid.
Such reaction may be represented as follows:
R, R,, R R X, m, n, P, and Y are previously defined.
A represents an integer of from 1 to 5.
the new and useful antistatic agents of the present invention have been found to have unexpectedly advantageous antistatic properties, particularly when applied to synthetic fibers, such as polyesters, acrylics, polyolefins, polyamides, etc. Such antistatic agents have been found to reduce and maintain the electrostatic charges for extended periods of time below a potential of 3 kilovolts.
EXAMPLE 1 a To a round bottom flask was charged a total of 288 parts by weight of an ethoxylate (1.85 moles E0) of a C C straight chain primary alcohol admixture calculated as a 209 MW. average and having the compo- The ethoxylate was agitated at ambient temperature (2030C.) while 77 parts phosphorous oxychloride (0.5 mol.) were dropped in over about 1.5 to'2.0 hours. After addition of phosphorous oxychloride was completed the batch was heated to 60-70C. and held 1 hour. Dry nitrogen was then bubbled through the mixture and the temperature was maintained for one hour. Samples were then run and repeated at one hour intervals until the percent chlorine on hydrolyzed sample showed as low as theoretical.
the product was stripped to l 10C. pot temperature under line vacuum and then filtered.
the weight of the final product was 451 gms.
the product was stripped to 1 10C. pot temperature under line vacuum and then filtered.
the weight of the final product was 437 gms.
the product was stripped to 1 10C. put temperature under line vacuum and then filtered.
the weight of the final product was 440 gms.
EXAMPLE IV a To a round bottom flask was charged a total of 306 parts by weight of an ethoxylate (4.0 mole E0.) of octyl alcohol. The ethoxylate was agitated at ambient temperature (30C) while 77 parts phosphorous oxychloride (0.5 ml) were dropped in over about 1.5 to 2.0 hours. After addition of phosphorous oxychloride was completed the batch was heated to 6070C and held one hour longer. Samples were then run and repeated at one hour intervals until the percent chlorine on hydrolyzed samples showed as low as theoretical.
ethoxylate 4.0 mole E0.
octyl alcohol octyl alcohol
the product was stripped to 110C pot temperature under line vacuum and then filtered.
the weight of the final product was 460 gms.
the swatches were conditioned at 72F and 50% relative humidity for at least 24 hours and the resistivity measured.
EXAMPLE V a To a round bottom flask was charged a total of 660 parts by weight of an ethoxylate (10.0 moles E0) of nonyl phenol. The ethoxylate was agitated at ambient temperature (2030C) while 77 parts phosphorous o'xychloride (0.5 mol.) were dropped in over about 1.5 to 2.0 hours. After addition of phosphorous oxychloride was completed the batch was heated to 60-70C and held 1 hour. Dry nitrogen was then bubbled through the mixture and the temperature was maintained for one hour. Samples were then run and repeated at one hour intervals until the percent chlorine on hydrolized sample showed-as low as theoretical.
the product was stripped to 1 10C pot temperature under line vacuum and then filtered.
the weight of the final product was 886 gms.
the swatches were conditioned at 72F and 50% re1- ative humidity for at least 24 hours and the resistivity
the product generally corresponds to the formula:

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Materials Engineering (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

US00765001A 1968-10-04 1968-10-04 Phosphonamides Expired - Lifetime US3856895A (en)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
US00765001A US3856895A (en)	1968-10-04	1968-10-04	Phosphonamides
GB4660869A GB1287915A (de)	1968-10-04	1969-09-22
DE19691948201 DE1948201A1 (de)	1968-10-04	1969-09-24	Antistatische Phosphorverbindungen
FR6933240A FR2019897A1 (de)	1968-10-04	1969-09-30
CH1486269A CH514022A (de)	1968-10-04	1969-10-02	Verfahren zur antistatischen Ausrüstung von Textilfasern
JP44079136A JPS4813533B1 (de)	1968-10-04	1969-10-02
CH1486269D CH1486269A4 (de)	1968-10-04	1969-10-02
CH1873769*A CH542885A (de)	1968-10-04	1969-10-02	Verfahren zur Herstellung neuer antistatischer Phosphorverbindungen
NL6915032A NL6915032A (de)	1968-10-04	1969-10-03
BE739835D BE739835A (de)	1968-10-04	1969-10-03

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US00765001A US3856895A (en)	1968-10-04	1968-10-04	Phosphonamides

Publications (1)

Publication Number	Publication Date
US3856895A true US3856895A (en)	1974-12-24

Family

ID=25072367

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US00765001A Expired - Lifetime US3856895A (en)	1968-10-04	1968-10-04	Phosphonamides

Country Status (8)

Country	Link
US (1)	US3856895A (de)
JP (1)	JPS4813533B1 (de)
BE (1)	BE739835A (de)
CH (3)	CH1486269A4 (de)
DE (1)	DE1948201A1 (de)
FR (1)	FR2019897A1 (de)
GB (1)	GB1287915A (de)
NL (1)	NL6915032A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4845285A (en) *	1986-11-25	1989-07-04	Imperial Chemical Industries Plc	Chemical process

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2302805A (en) *	1936-09-03	1942-11-24	Gen Aniline & Film Corp	Composition for mothproofing

1968
- 1968-10-04 US US00765001A patent/US3856895A/en not_active Expired - Lifetime
1969
- 1969-09-22 GB GB4660869A patent/GB1287915A/en not_active Expired
- 1969-09-24 DE DE19691948201 patent/DE1948201A1/de active Pending
- 1969-09-30 FR FR6933240A patent/FR2019897A1/fr not_active Withdrawn
- 1969-10-02 CH CH1486269D patent/CH1486269A4/xx unknown
- 1969-10-02 CH CH1873769*A patent/CH542885A/de not_active IP Right Cessation
- 1969-10-02 CH CH1486269A patent/CH514022A/de not_active IP Right Cessation
- 1969-10-02 JP JP44079136A patent/JPS4813533B1/ja active Pending
- 1969-10-03 BE BE739835D patent/BE739835A/xx unknown
- 1969-10-03 NL NL6915032A patent/NL6915032A/xx unknown

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2302805A (en) *	1936-09-03	1942-11-24	Gen Aniline & Film Corp	Composition for mothproofing

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Kondratev et al., Index Chemicus, Vol. 19, page 57137 (1965). *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4845285A (en) *	1986-11-25	1989-07-04	Imperial Chemical Industries Plc	Chemical process

Also Published As

Publication number	Publication date
JPS4813533B1 (de)	1973-04-27
GB1287915A (de)	1972-09-06
BE739835A (de)	1970-03-16
CH514022A (de)	1971-05-28
CH1486269A4 (de)	1971-05-28
FR2019897A1 (de)	1970-07-10
NL6915032A (de)	1970-04-07
CH542885A (de)	1973-11-30
DE1948201A1 (de)	1970-04-16

Legal Events

Date	Code	Title	Description
1989-06-14	AS	Assignment	Owner name: CHASE MANHATTAN BANK, THE NATIONAL ASSOCIATION Free format text: SECURITY INTEREST;ASSIGNOR:DORSET INC. A CORP OF DELAWARE;REEL/FRAME:005122/0370 Effective date: 19890329
1989-10-30	AS	Assignment	Owner name: GAF CHEMICALS CORPORATION Free format text: CHANGE OF NAME;ASSIGNOR:DORSET INC.;REEL/FRAME:005251/0071 Effective date: 19890411
1990-04-06	AS	Assignment	Owner name: RHONE-POULENC SPECIALTY CHEMICALS, L.P., NEW JERSE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:GAF CHEMICALS CORPORATION;REEL/FRAME:005315/0588 Effective date: 19900404
1990-10-30	AS	Assignment	Owner name: DORSET INC., A DE CORP. Free format text: CHANGE OF NAME;ASSIGNOR:GAF CORPORATION, A DE CORP.;REEL/FRAME:005250/0940 Effective date: 19890410
1991-01-22	AS	Assignment	Owner name: DORSET INC., Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:CHASE MANHATTAN BANK, THE,;REEL/FRAME:005597/0269 Effective date: 19890329
1991-05-30	AS	Assignment	Owner name: RHONE - POULENC SPECIALITY CHEMICALS Free format text: A CORRECTIVE ASSIGNMENT TO CORRECT THE SINGLE SERIAL NUMBER 07194,259 IDENTIFIED IN PREVIOUSLY RECORDED ASSIGMENT ON REEL 5315/FRAME 589.;ASSIGNOR:GAF CHEMICALS CORPORATION;REEL/FRAME:005722/0439 Effective date: 19910513
1991-06-24	AS	Assignment	Owner name: RHONE-POULENC SURFACTANTS AND SPECIALTIES INC., NE Free format text: CHANGE OF NAME;ASSIGNOR:RHONE-POULENC SPECIALTY CHEMICALS INC.;REEL/FRAME:005748/0167 Effective date: 19910123

Publication	Publication Date	Title
US3454625A (en)	1969-07-08	Novel quaternary ammonium carbamate antistatic agents
US3445440A (en)	1969-05-20	Hydroxyalkyl quaternary ammonium ethers as antistatic agents
US2676122A (en)	1954-04-20	Antistatic treatment of hydrophobic fiber
US3274244A (en)	1966-09-20	Polyfluoropolyoxa-alkanamidoalkyl compounds
DD153683A5 (de)	1982-01-27	Verfahren zur reinigung von interferon
DE69428456T2 (de)	2002-05-02	Silikon-modifizierte phospholipid-zusammensetzungen
US4132657A (en)	1979-01-02	Treatment of metal surfaces
US2742379A (en)	1956-04-17	Treatment of textile fibers with antistatic agent and product thereof
US2719156A (en)	1955-09-27	Methylolated quaternary ammonium compounds
US4416830A (en)	1983-11-22	Polyether phosphoric acids or esters
US3856895A (en)	1974-12-24	Phosphonamides
EP0098034A3 (de)	1984-03-28	Verfahren zur Herstellung von N-Phosphonomethylglyzinderivaten und herbizide Verbindungen und damit hergestellte Zusammensetzungen
US3374292A (en)	1968-03-19	Phosphono carboxamides
SE447916B (sv)	1986-12-22	Textilmjukgorande och antistatisk komposition innehallande en anjonisk fosforsyraester och ett katjoniskt mjukgoringsmedel
US3517045A (en)	1970-06-23	Hydroxyalkyl quaternary ammonium ethers as antistatic agents
US3658882A (en)	1972-04-25	Novel carbamate antistatic agents
US3516853A (en)	1970-06-23	Process for flameproofing polymeric materials
US3741801A (en)	1973-06-26	Fabric treatment with halogenated carbamate antistatic agents
US3366671A (en)	1968-01-30	Betaines
GB821503A (en)	1959-10-07	Polymeric compositions containing nitrilo methylol-phosphorus polymers and bromine
US3634117A (en)	1972-01-11	A textile material coated with an ammonium dialkyl phosphate antistatic agent
EP0029172B1 (de)	1983-03-02	Alkanphosphonsäurehalbestersalze, ihre Herstellung und ihre Anwendung als Präparationsmittel für textile Fasern
US3686368A (en)	1972-08-22	Phosphonamide antistatic agents
US3363032A (en)	1968-01-09	Long chain aliphatic benzylphosphonic acids, esters and salts
US4822529A (en)	1989-04-18	Antistatic agents for synthetic fibers and methods of producing same

US3856895A - Phosphonamides - Google Patents

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