US3770495A - Non-adhesive high elastic elastomer threads - Google Patents
Non-adhesive high elastic elastomer threads Download PDFInfo
- Publication number
- US3770495A US3770495A US3770495DA US3770495A US 3770495 A US3770495 A US 3770495A US 3770495D A US3770495D A US 3770495DA US 3770495 A US3770495 A US 3770495A
- Authority
- US
- United States
- Prior art keywords
- threads
- thread
- formula
- highly elastic
- dressing
- 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
Links
- 239000000853 adhesive Substances 0.000 title claims description 10
- 229920001971 elastomer Polymers 0.000 title description 14
- 239000000806 elastomer Substances 0.000 title description 12
- 239000011248 coating agent Substances 0.000 claims abstract description 6
- 238000000576 coating method Methods 0.000 claims abstract description 6
- 125000002270 phosphoric acid ester group Chemical group 0.000 claims abstract 2
- 230000001070 adhesive effect Effects 0.000 claims description 8
- 229920003225 polyurethane elastomer Polymers 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 abstract description 12
- 239000004814 polyurethane Substances 0.000 abstract description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 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
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 239000004615 ingredient Substances 0.000 abstract 1
- 150000003014 phosphoric acid esters Chemical group 0.000 description 11
- 238000009987 spinning Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000005662 Paraffin oil Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- -1 siloxanes Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- FRXGWNKDEMTFPL-UHFFFAOYSA-N dioctadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCC FRXGWNKDEMTFPL-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
Definitions
- ABSTRACT Normally sticky segmented polyurethane threads are rendered non-adhesive by coating with a dressing agent comprising tertiary phosphoric acid ester of the formula o o P in which R is a hydrocarbon radical of the-formula C l-1 or C 1-1 q is 10 to 20; and p is an integer of from 4 to 50.
- This invention relates to non-adhesive, highly elastic threads from polyurethane elastomers (segmented polyurethanes) to a dressing agent for adhesive, highly elastic'threads and to a process for dressing highly elastic and highly stretchable threads with specific dressing agents.
- highly elastic threads such as rubber threads or synthetic threads which are made of highly elastic, segmented polyurethanes can only be worked up without difficulty if a suitable dressing has first been applied to their surface.
- Highly elastic elastomer threads which have an elongation at break in the region of 400 to 800 percent and in which the fibre forming substance is a polymer in the form of a chain which consists of at least 85 percent of a segmented polyurethane have a much greater tendency to stick together than the so-called hard threads.
- These threads stick together in the thread package and their adhesion to other surfaces, for example to the surface of the thread guide elements, is also especially marked.
- Rubber threads are usually dressed with talcum, and this also may be used for elastomer threads made of highly elastic, segmented polyurethanes, although the talcum dust wich is easily rubbed off causes soiling and even damage to the textile machines used for the subsequent working up. It has therefore already been proposed to dress threads of highly elastic, segmented polyurethanes with textile oils such as mineral oil in whichcertain metal soaps are finely dispersed.
- the soaps used are preferably sodium, magnesium, zinc or aluminium salts of long chain fatty acids. These dispersions are preferably applied to the highly elastic threads during the spinning process.
- Polyamyl siloxanes are said to be advantageous for use as dressing agents for certain threads of highly elastic, segmented polyurethanes whilst in other cases an application or organic silicic acid esters such as tetrakis-(Z-ethylbutyl) silicate has proved to be satisfactory.
- R and R denote a hydrocarbon radical of the formula C,,H or C,,l-l (n 1 to 20, m l to 6) and R represents a hydrogen atom or a methyl group, are suitable for use in the process according to the invention.
- the quantities of ethylene oxide adduct which are added vary according to the constitution and nature of the tertiary phosphoric acid ester used.
- the tertiary phosphoric acid esters are non-ionic compounds and therefore ensure that the polyurethane elastomer threads do not affect the ionic activity of the brightening agents for mixed fibres and of the detergents and certain dyes. This means that precipitation with other dressing agents, detergents or dyes are not to be expected.
- the tertiary phosphoric acid esters After the tertiary phosphoric acid esters have been mixed with emulsifying alkylene oxide adducts, they are dispersed, or preferably dissolved, in so-called textile oils, e.g. mineral oil in concentrations of between 10 and 90 percent, depending on the particular requirements.
- textile oils e.g. mineral oil in concentrations of between 10 and 90 percent, depending on the particular requirements.
- the mixtures so obtained are liquid to pasty at room temperature and are frequently even of a waxy consistency, depending on the nature and proportions of the phosphoric acid ester, emulsifying agent and oil used. If the viscosity of such a mixture is too high, a solvent which is inert to the elastomer substrate may be added.
- the dressing mixture is applied at elevated temperature by means of rollers which dip into heated vats.
- the phosphoric acid esters may be applied to the threads without any further additives and if desired in the form of a melt.
- the elastomer threads should contain an amount of phosphoric acid ester equal to 0.5 to 10 percent and preferably 1 to 5 percent of their own weight.
- This treatment enables the production of highly elastic elastomer threads which are non-sticky in the pack age even when packages of higher weight are produced, and which therefore will run off the package smoothly even after prolonged storage.
- the application of the dressing according to the invention ensures that smoothness of the thread surface which is necessary for further working up, ensures adequate protection against the accumulation of electrostatic charges and causes practically no alteration in the properties, especially the physical properties such as the capacity for elastic recovery of the threads.
- the elastomer threads can be produced by known procedures from spinning solutions of segmented polyurethanes, e.g. according to German Patent Specification No. 1,123,467 or according to German Auslegeschriften Nos. 1,183,196 and 1,161,007. The following examples illustrate more particularly the invention.
- Example 1 A solution of the following composition:
- the total titre of the threads is 400 den and the amount of dressing applied, which is determined by extraction with carbon tetrachloride, is 5 percent of the weight of the thread. Even after the spinning spool has been left to stand for 8 days, the layers of thread on the package have not stuck together and the thread can be rewound without any increased thread tensions and consequently any marked stretching of the highly elastic thread taking place.
- Example 2 A solution of the following composition: 24 parts by weight of adduct of 1 mol of die-oleyl phosphate and 2 mols of ethylene oxide, 6 parts by weight of adduct of 1 mol of oleyl alcohol and 20 mols of ethylene oxide, 70 parts by weight of paraffin oil of viscosity 35 to 45 cP/20C is applied to the spun elastomer threads after they have left the spinning shaft, using dressing rollers which dip into vats heated to 60C.
- the total titre of the thread is 400 den and the amount of dressing applied, which is determined by extraction with carbon tetrachloride, is 7 percent of the weight of the thread.
- the layers of thread on the package are not stuck together even after the spinning spool has been left to stand for 8 days, and the thread can be rewound without increased thread tensions and hence any marked stretching of the highly elastic thread taking place.
- Example 3 A solution of the following composition: 20 parts by weight of adduct of 1 mol of di-ioctylphosphate and 2 mols of ethylene oxide, 10 parts by weight of adduct of 1 mol of lauryl alcohol and 5 mols of ethylene oxide, is applied to the spun elastomer threads after they leave the spinning shaft, using dressing rollers.
- the total titre of the thread is 400 den and theamount of dressing applied, which is determined by extraction with carbon tetrachloride, is l0 percent, based on the weight of the thread.
- the layers of thread on the package are not stuck together even after the spinning spool has been left to stand for 4 days, and the thread can be rewound without any increased thread tensions and therefore marked stretching of the highly elastic thread taking place.
- a non-adhesive highly elastic thread comprising a normally sticky segmented polyurethane elastomer having a coating consisting essentially of 0.5 to 10 percent by weight based on the weight of the elastomer thread of a tertiary phosphoric acid ester of the formula R-,() (()(2H;,R;,),()H
- R and R are hydrocarbon radicals of the formula n 2n+I n zrhli n is l to 20;
- m l to 6
- R is hydrogen or methyl
- n l to 20;
- n 1 to 6;
- R is hydrogen or methyl; and an ethylene oxide adduct of the formula in which R is a hydrocarbon radical of the formula q 2q+l or q 2ql;
- q 10 to 20
- p 4 to 50.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0054500 | 1968-01-08 | ||
DE1669432A DE1669432C3 (de) | 1968-01-08 | 1968-01-08 | Verklebungsfrei machende Präparation von hochelastischen Fäden aus segmentierten Polyurethanen |
Publications (1)
Publication Number | Publication Date |
---|---|
US3770495A true US3770495A (en) | 1973-11-06 |
Family
ID=25754363
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US3770495D Expired - Lifetime US3770495A (en) | 1968-01-08 | 1971-10-28 | Non-adhesive high elastic elastomer threads |
Country Status (8)
Country | Link |
---|---|
US (1) | US3770495A (is") |
BE (1) | BE726618A (is") |
CH (1) | CH482861A (is") |
DE (1) | DE1669432C3 (is") |
FR (1) | FR2000073A1 (is") |
GB (1) | GB1253252A (is") |
NL (1) | NL160042C (is") |
SE (1) | SE354878B (is") |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3908048A (en) * | 1972-04-07 | 1975-09-23 | Kao Corp | Method of improving interfiber cohesion of filament yarns |
US4348238A (en) * | 1980-06-26 | 1982-09-07 | Eastman Kodak Company | Manufacture of cellulose ester film |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
US2742379A (en) * | 1954-02-25 | 1956-04-17 | Du Pont | Treatment of textile fibers with antistatic agent and product thereof |
US2842462A (en) * | 1953-12-21 | 1958-07-08 | Bohme Fettchemie Gmbh | Antistatic synthetic textile material |
US2909559A (en) * | 1958-02-03 | 1959-10-20 | Union Carbide Corp | Polymeric phosphate esters and their production |
US2990421A (en) * | 1958-04-01 | 1961-06-27 | Virginia Carolina Chem Corp | Neutral esters of phosphoric acid |
US3310935A (en) * | 1963-04-02 | 1967-03-28 | Nat Starch Chem Corp | Method for preparing yarn from fibers |
US3407150A (en) * | 1963-02-07 | 1968-10-22 | Pittsburgh Plate Glass Co | Oxyalkylated phosphorus acid esters as urethane fire-retardants |
US3432343A (en) * | 1966-06-28 | 1969-03-11 | Union Carbide Corp | Fibers and fabrics coated with an alkyl phosphite-polyolefin wax adduct and process therefor |
US3472919A (en) * | 1964-08-13 | 1969-10-14 | Ugine Kuhlmann | Hydroxyl containing polytertiary phosphates and process for producing same |
US3482010A (en) * | 1963-09-30 | 1969-12-02 | Kuraray Co | Process for the production of polyurethane elastic fiber having less adhesivity |
US3495394A (en) * | 1965-10-11 | 1970-02-17 | Ici Ltd | Elastomeric yarns |
-
1968
- 1968-01-08 DE DE1669432A patent/DE1669432C3/de not_active Expired
- 1968-12-09 CH CH1837068A patent/CH482861A/de not_active IP Right Cessation
-
1969
- 1969-01-03 SE SE00069/69A patent/SE354878B/xx unknown
- 1969-01-07 GB GB1253252D patent/GB1253252A/en not_active Expired
- 1969-01-08 BE BE726618D patent/BE726618A/xx unknown
- 1969-01-08 NL NL6900298A patent/NL160042C/xx not_active IP Right Cessation
- 1969-01-08 FR FR6900139A patent/FR2000073A1/fr not_active Withdrawn
-
1971
- 1971-10-28 US US3770495D patent/US3770495A/en not_active Expired - Lifetime
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
US2842462A (en) * | 1953-12-21 | 1958-07-08 | Bohme Fettchemie Gmbh | Antistatic synthetic textile material |
US2742379A (en) * | 1954-02-25 | 1956-04-17 | Du Pont | Treatment of textile fibers with antistatic agent and product thereof |
US2909559A (en) * | 1958-02-03 | 1959-10-20 | Union Carbide Corp | Polymeric phosphate esters and their production |
US2990421A (en) * | 1958-04-01 | 1961-06-27 | Virginia Carolina Chem Corp | Neutral esters of phosphoric acid |
US3407150A (en) * | 1963-02-07 | 1968-10-22 | Pittsburgh Plate Glass Co | Oxyalkylated phosphorus acid esters as urethane fire-retardants |
US3310935A (en) * | 1963-04-02 | 1967-03-28 | Nat Starch Chem Corp | Method for preparing yarn from fibers |
US3482010A (en) * | 1963-09-30 | 1969-12-02 | Kuraray Co | Process for the production of polyurethane elastic fiber having less adhesivity |
US3472919A (en) * | 1964-08-13 | 1969-10-14 | Ugine Kuhlmann | Hydroxyl containing polytertiary phosphates and process for producing same |
US3495394A (en) * | 1965-10-11 | 1970-02-17 | Ici Ltd | Elastomeric yarns |
US3432343A (en) * | 1966-06-28 | 1969-03-11 | Union Carbide Corp | Fibers and fabrics coated with an alkyl phosphite-polyolefin wax adduct and process therefor |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3908048A (en) * | 1972-04-07 | 1975-09-23 | Kao Corp | Method of improving interfiber cohesion of filament yarns |
US4348238A (en) * | 1980-06-26 | 1982-09-07 | Eastman Kodak Company | Manufacture of cellulose ester film |
Also Published As
Publication number | Publication date |
---|---|
NL6900298A (is") | 1969-07-10 |
SE354878B (is") | 1973-03-26 |
CH482861A (de) | 1970-01-30 |
NL160042C (nl) | 1979-09-17 |
CH1837068A4 (is") | 1970-01-30 |
GB1253252A (is") | 1971-11-10 |
BE726618A (is") | 1969-06-16 |
DE1669432C3 (de) | 1976-01-02 |
DE1669432B2 (de) | 1975-05-07 |
DE1669432A1 (de) | 1971-08-12 |
FR2000073A1 (is") | 1969-08-29 |
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