US3092435A - Process of dyeing polyethylene and polypropylene materials - Google Patents
Process of dyeing polyethylene and polypropylene materials Download PDFInfo
- Publication number
- US3092435A US3092435A US27471A US2747160A US3092435A US 3092435 A US3092435 A US 3092435A US 27471 A US27471 A US 27471A US 2747160 A US2747160 A US 2747160A US 3092435 A US3092435 A US 3092435A
- Authority
- US
- United States
- Prior art keywords
- anthraquinone
- dye
- fastness
- butylamino
- proceeding
- 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
- 238000000034 method Methods 0.000 title claims description 30
- 239000000463 material Substances 0.000 title claims description 7
- -1 polyethylene Polymers 0.000 title description 16
- 239000004698 Polyethylene Substances 0.000 title description 7
- 239000004743 Polypropylene Substances 0.000 title description 7
- 238000004043 dyeing Methods 0.000 title description 7
- 229920000573 polyethylene Polymers 0.000 title description 7
- 229920001155 polypropylene Polymers 0.000 title description 7
- 229920002994 synthetic fiber Polymers 0.000 claims description 6
- 238000009967 direct dyeing Methods 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000001000 anthraquinone dye Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 23
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 9
- 150000004056 anthraquinones Chemical class 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- OCQDPIXQTSYZJL-UHFFFAOYSA-N 1,4-bis(butylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCCC)=CC=C2NCCCC OCQDPIXQTSYZJL-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- AWGCJODNVVGFRV-UHFFFAOYSA-N 1,4-bis(2-methylpropylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCC(C)C)=CC=C2NCC(C)C AWGCJODNVVGFRV-UHFFFAOYSA-N 0.000 description 1
- ZTADCQTUHRWJCM-UHFFFAOYSA-N 1,4-bis(cyclohexylamino)anthracene-9,10-dione Chemical compound C1=CC(NC2CCCCC2)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1CCCCC1 ZTADCQTUHRWJCM-UHFFFAOYSA-N 0.000 description 1
- BLFZMXOCPASACY-UHFFFAOYSA-N 1,4-bis(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC(C)C)=CC=C2NC(C)C BLFZMXOCPASACY-UHFFFAOYSA-N 0.000 description 1
- NWGIPEBGAOQGCJ-UHFFFAOYSA-N 1,5-bis(2-methylpropylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(NCC(C)C)C=CC=C2C(=O)C2=C1C=CC=C2NCC(C)C NWGIPEBGAOQGCJ-UHFFFAOYSA-N 0.000 description 1
- MLZFWBQTQKBDSJ-UHFFFAOYSA-N 1-(butylamino)-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2NCCCC MLZFWBQTQKBDSJ-UHFFFAOYSA-N 0.000 description 1
- ITYXXSSJBOAGAR-UHFFFAOYSA-N 1-(methylamino)-4-(4-methylanilino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(NC)=CC=C1NC1=CC=C(C)C=C1 ITYXXSSJBOAGAR-UHFFFAOYSA-N 0.000 description 1
- ULHCQQPTVHUANA-UHFFFAOYSA-N 1-amino-2-bromo-4-(butylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Br)C=C2NCCCC ULHCQQPTVHUANA-UHFFFAOYSA-N 0.000 description 1
- XAVJMERUUMLAFD-UHFFFAOYSA-N 1-amino-4-(propylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2NCCC XAVJMERUUMLAFD-UHFFFAOYSA-N 0.000 description 1
- QQOJBTKAGBIFRS-UHFFFAOYSA-N 1-hydroxy-4-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2NC(C)C QQOJBTKAGBIFRS-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 241000300547 Viola ambigua Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- AIOLRLMFOWGSPL-UHFFFAOYSA-N chembl1337820 Chemical compound C1=CC=C2C(N=NC3=C4C=CC(=CC4=CC(=C3O)S(O)(=O)=O)S(O)(=O)=O)=CC=CC2=C1 AIOLRLMFOWGSPL-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/79—Polyolefins
- D06P3/794—Polyolefins using dispersed dyes
Definitions
- This invention relates to a method for the direct dyeing of synthetic materials obtained by polymerizing monoolefinic hydrocarbons such as ethylene and propylene. The polymer may then be worked to obtain yarns or films.
- the anthraquinone nucleus may also contain other substituents such as halogens, alkyls, OH, OR,
- the aflinity for the material to be dyed is so great that it is no longer necessary to use swelling agents or carriers, nor is it necessarry to carry out the dyeing at temperatures in excess of 100 C.
- Example 1 10 g. of polypropylene fibres are immersed in a dyeing bath containing 0.1 g. of the following compound (1,4- di(butylamino) anthraquinone):
- the dyeing is carried out at the boiling temperature
- the fibre is 2 then strongly soaped at 40-60 C.
- a brilliant blue color with a reddish shade, having high intensity and good fastness, is obtained.
- Example 2 By proceeding as described in Example 1, but substituting for the 1,4-di(butylamino) anthraquinone, the fibre is dyed an intense brilliant greenish blue color having good cfiastness.
- Example 3 By proceeding as described in Example 1, but substia very brilliant intense blue color with good fastness is 10 g. of polyethylene film (NI-W. 31,000, determined according to Harris, J. Polymer Science 1952, p. 353) are immersed in a bath containing 0.1 g. of the dye employed in Example 1 and 0.1 g. of ordinary soap. Dyeing is carried out at C.-for 30 minutes. A blue color having good intensity and fastness is obtained.
- polyethylene film NI-W. 31,000, determined according to Harris, J. Polymer Science 1952, p. 353
- Dyeing is carried out at C.-for 30 minutes. A blue color having good intensity and fastness is obtained.
- Example 2 By proceeding as described in Example l'but substituting for the 1,4-dibutylarnino) anthraquinone 0.1 g. of the following compound I O l lHCiHm a blue gray color having good fastnes's is obtained.
- Example 6 By proceeding as described in Example 1, but substituting for -the l,4-di(butylamino) anthraquinone a compound having the formula /CH3 IfH-OHa-OH a red color with good intensity and fastness is obtained.
- Example 7 By proceeding as described in Example 1, but substituting NH are H on, ⁇ CHS for the l,4-di(butylamino) anthraquinone, a bordeauxred color having good intensity and fastness is obtained.
- Example 8 By proceeding as described in Example 1, but substituting for the 1,4-di(butylamino) anthraquinone a blue color with good intensity and iastness is obtained.
- Example 9 By proceeding as described in Example 1, but substitoting g 7 OH: (H) NH-CHa-C 6 NH-CHn-CH for the 1,4-di(buty1amino) anthraquinone a blue color with good intensity and i'astness is obtained.
- Example 11 By proceeding as described in Example 1, but substituting I /OHa b NEOH2O for the 1,4-di('butylamino)anthraquinone, a violet color with good intensity and fastness is obtained.
- Example 12 By proceeding as described in Example 1, but substituting Y for the 1,4-di-(butylamino)anthraquinone, a blue color with good intensity and fastness is obtained.
- Example 14 By proceeding as described in Example 1, but substituting i O NH-O'Hz-CHrGH;
- Example 15 By proceeding as described in Example 1, but substituting :for the 1,4-di(hutylamino) anthraquinone, a blue color with good intensity and fastness is obtained.
- Example 1 6 By proceeding as described in Example 1, but substituting NH-OH for the 1,4-di(butylamino)anthraquinone, a violet color with good intensity and fastness is obtained.
- Example 17 By proceeding as described in Example 1, but substituting for the 1,4-di(butylamino)anthraquinone, a violet color with good intensity and fastness is obtained.
- R is selected from the group consisting of alkyl, cycloalkyl, and aryl containing up to 10 carbon atoms, and n is a positive integer from 1 to 6.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT793859 | 1959-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3092435A true US3092435A (en) | 1963-06-04 |
Family
ID=11125553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US27471A Expired - Lifetime US3092435A (en) | 1959-05-11 | 1960-05-09 | Process of dyeing polyethylene and polypropylene materials |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3092435A (en)van) |
| BE (1) | BE590670A (en)van) |
| CH (1) | CH371778A (en)van) |
| DE (1) | DE1201295B (en)van) |
| ES (1) | ES258127A1 (en)van) |
| FR (1) | FR1257940A (en)van) |
| GB (1) | GB872882A (en)van) |
| LU (1) | LU38619A1 (en)van) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3223752A (en) * | 1961-05-31 | 1965-12-14 | Monsanto Co | Dyeable polyolefin containing modified polyester |
| US3226177A (en) * | 1961-12-02 | 1965-12-28 | Mitsui Kagaku Kogyo Kabushiki | Process for the dyeing of polyolefin fibrous materials |
| US3337288A (en) * | 1963-05-06 | 1967-08-22 | Dainichiseika Color Chem | Reactive coloring matter, processes for producing the same and processes for coloring articles with the same |
| US3390947A (en) * | 1964-06-24 | 1968-07-02 | Gen Aniline & Film Corp | Process for dyeing polyester textile materials with substituted anthraquinone dyestuffs |
| US3441536A (en) * | 1964-09-14 | 1969-04-29 | Allied Chem | Synthetic resin compositions containing alpha - phenylthioanthraquinones as colorants |
| US3485569A (en) * | 1966-10-11 | 1969-12-23 | Du Pont | Process for dyeing fabric having polypropylene backing and polyamide pile yarns |
| FR2417527A1 (fr) * | 1978-02-17 | 1979-09-14 | Bayer Ag | Nouveaux colorants anthraquinoniques non porteurs de groupes nitro et de groupes acide sulfonique |
| US6126701A (en) * | 1999-06-08 | 2000-10-03 | Calogero; Frank | Method of dyeing polyolefin fibers |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2036196A (en) * | 1933-05-18 | 1936-04-07 | Ici Ltd | Application of dyestuffs |
| US2795477A (en) * | 1953-06-24 | 1957-06-11 | Cfmc | Coloration of fibres having a polyvinyl derivative base |
| US2848462A (en) * | 1950-10-31 | 1958-08-19 | Saul & Co | Dyestuffs of the anthraquinone series |
| US2895967A (en) * | 1958-03-07 | 1959-07-21 | Eastman Kodak Co | Metallized anthraquinone dyes |
| US2900216A (en) * | 1955-05-28 | 1959-08-18 | Bayer Ag | Process for the dyeing of polymers of acrylonitrile or asymmetric dicyanoethylene |
| US2952690A (en) * | 1957-03-12 | 1960-09-13 | Ciba Ltd | Anthraquinone dyestuffs |
| US2984634A (en) * | 1957-01-30 | 1961-05-16 | Eastman Kodak Co | Crystalline polymerized monoolefinic hydrocarbons containing metal salt of carboxylic acid |
-
0
- BE BE590670D patent/BE590670A/xx unknown
- LU LU38619D patent/LU38619A1/xx unknown
-
1960
- 1960-05-06 GB GB16109/60A patent/GB872882A/en not_active Expired
- 1960-05-07 DE DEA34595A patent/DE1201295B/de active Pending
- 1960-05-09 CH CH530060A patent/CH371778A/de unknown
- 1960-05-09 US US27471A patent/US3092435A/en not_active Expired - Lifetime
- 1960-05-09 FR FR826619A patent/FR1257940A/fr not_active Expired
- 1960-05-10 ES ES0258127A patent/ES258127A1/es not_active Expired
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2036196A (en) * | 1933-05-18 | 1936-04-07 | Ici Ltd | Application of dyestuffs |
| US2848462A (en) * | 1950-10-31 | 1958-08-19 | Saul & Co | Dyestuffs of the anthraquinone series |
| US2795477A (en) * | 1953-06-24 | 1957-06-11 | Cfmc | Coloration of fibres having a polyvinyl derivative base |
| US2900216A (en) * | 1955-05-28 | 1959-08-18 | Bayer Ag | Process for the dyeing of polymers of acrylonitrile or asymmetric dicyanoethylene |
| US2984634A (en) * | 1957-01-30 | 1961-05-16 | Eastman Kodak Co | Crystalline polymerized monoolefinic hydrocarbons containing metal salt of carboxylic acid |
| US2952690A (en) * | 1957-03-12 | 1960-09-13 | Ciba Ltd | Anthraquinone dyestuffs |
| US2895967A (en) * | 1958-03-07 | 1959-07-21 | Eastman Kodak Co | Metallized anthraquinone dyes |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3223752A (en) * | 1961-05-31 | 1965-12-14 | Monsanto Co | Dyeable polyolefin containing modified polyester |
| US3226177A (en) * | 1961-12-02 | 1965-12-28 | Mitsui Kagaku Kogyo Kabushiki | Process for the dyeing of polyolefin fibrous materials |
| US3337288A (en) * | 1963-05-06 | 1967-08-22 | Dainichiseika Color Chem | Reactive coloring matter, processes for producing the same and processes for coloring articles with the same |
| US3390947A (en) * | 1964-06-24 | 1968-07-02 | Gen Aniline & Film Corp | Process for dyeing polyester textile materials with substituted anthraquinone dyestuffs |
| US3441536A (en) * | 1964-09-14 | 1969-04-29 | Allied Chem | Synthetic resin compositions containing alpha - phenylthioanthraquinones as colorants |
| US3485569A (en) * | 1966-10-11 | 1969-12-23 | Du Pont | Process for dyeing fabric having polypropylene backing and polyamide pile yarns |
| FR2417527A1 (fr) * | 1978-02-17 | 1979-09-14 | Bayer Ag | Nouveaux colorants anthraquinoniques non porteurs de groupes nitro et de groupes acide sulfonique |
| US6126701A (en) * | 1999-06-08 | 2000-10-03 | Calogero; Frank | Method of dyeing polyolefin fibers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB872882A (en) | 1961-07-12 |
| BE590670A (en)van) | |
| LU38619A1 (en)van) | |
| ES258127A1 (es) | 1960-11-16 |
| FR1257940A (fr) | 1961-04-07 |
| CH371778A (de) | 1963-10-31 |
| DE1201295B (de) | 1965-09-23 |
| CH530060A4 (en)van) | 1963-03-29 |
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