DE1253915B - Verfahren zur Herstellung von farbigen Copolymerisaten - Google Patents
Verfahren zur Herstellung von farbigen CopolymerisatenInfo
- Publication number
- DE1253915B DE1253915B DE1964B0078022 DEB0078022A DE1253915B DE 1253915 B DE1253915 B DE 1253915B DE 1964B0078022 DE1964B0078022 DE 1964B0078022 DE B0078022 A DEB0078022 A DE B0078022A DE 1253915 B DE1253915 B DE 1253915B
- Authority
- DE
- Germany
- Prior art keywords
- copolymers
- colored
- monomers
- couplable
- diazonium salt
- 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.)
- Pending
Links
- 229920001577 copolymer Polymers 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000000178 monomer Substances 0.000 claims description 17
- 150000001989 diazonium salts Chemical class 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- -1 vinyloxy, methacryloyl Chemical group 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DSGSJBHIXWGSNL-UHFFFAOYSA-N 1-(2-amino-3-hydroxyphenyl)prop-2-en-1-one Chemical compound NC1=C(O)C=CC=C1C(=O)C=C DSGSJBHIXWGSNL-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229920003180 amino resin Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 230000006855 networking Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- RHPCOPYCALZVCO-UHFFFAOYSA-N 1-(5-hydroxy-2-methylphenyl)prop-2-en-1-one Chemical compound C(C=C)(=O)C=1C=C(C=CC1C)O RHPCOPYCALZVCO-UHFFFAOYSA-N 0.000 description 1
- MXVNVVHIVCETAK-UHFFFAOYSA-N 1-(5-hydroxynaphthalen-1-yl)prop-2-en-1-one Chemical compound C(C=C)(=O)C1=CC=CC2=C(C=CC=C12)O MXVNVVHIVCETAK-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical group [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- 150000005004 2-naphthylamines Chemical class 0.000 description 1
- KXLSDFQBJPRCDC-UHFFFAOYSA-N 3-ethenyl-1h-imidazol-3-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C=C[NH+]1C=CN=C1 KXLSDFQBJPRCDC-UHFFFAOYSA-N 0.000 description 1
- BKQDNMOOFPIQSI-UHFFFAOYSA-N 4-hydroxy-7-(prop-2-enoylamino)naphthalene-2-sulfonic acid Chemical compound OC1=C2C=CC(NC(=O)C=C)=CC2=CC(=C1)S(O)(=O)=O BKQDNMOOFPIQSI-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical group OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- TXGBUCUVAWOGMY-UHFFFAOYSA-N 7-ethenylsulfonylnaphthalen-2-ol Chemical compound C(=C)S(=O)(=O)C1=CC2=CC(=CC=C2C=C1)O TXGBUCUVAWOGMY-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- KURBROZYGHXNLK-UHFFFAOYSA-N N-(7-hydroxynaphthalen-1-yl)prop-2-enamide Chemical compound C(C=C)(=O)NC1=CC=CC2=CC=C(C=C12)O KURBROZYGHXNLK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- SIMASFZWTXQOGU-UHFFFAOYSA-N NC(=O)OCC.C(O)C(C(O)(O)CO)CC Chemical compound NC(=O)OCC.C(O)C(C(O)(O)CO)CC SIMASFZWTXQOGU-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- KZPUZDRBSSPUGI-UHFFFAOYSA-N n-(2-ethenoxyethyl)-n-ethylaniline Chemical compound C=COCCN(CC)C1=CC=CC=C1 KZPUZDRBSSPUGI-UHFFFAOYSA-N 0.000 description 1
- RQVBWOZIENNJHH-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]prop-2-enamide Chemical compound CN(C)C1=CC=CC(NC(=O)C=C)=C1 RQVBWOZIENNJHH-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YIGHKJJFYXTSGV-UHFFFAOYSA-N s-pyrazol-1-ylthiohydroxylamine Chemical compound NSN1C=CC=N1 YIGHKJJFYXTSGV-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1964B0078022 DE1253915B (de) | 1964-08-08 | 1964-08-08 | Verfahren zur Herstellung von farbigen Copolymerisaten |
| GB3369865A GB1064470A (https=) | 1964-08-08 | 1965-08-06 | |
| BE668027D BE668027A (https=) | 1964-08-08 | 1965-08-06 | |
| FR27697A FR1458306A (fr) | 1964-08-08 | 1965-08-09 | Copolymères colorés et procédé pour leur fabrication par réaction de sels de diazonium avec des copolymères renfermant des groupes copulables |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1964B0078022 DE1253915B (de) | 1964-08-08 | 1964-08-08 | Verfahren zur Herstellung von farbigen Copolymerisaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1253915B true DE1253915B (de) | 1967-11-09 |
Family
ID=6979704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1964B0078022 Pending DE1253915B (de) | 1964-08-08 | 1964-08-08 | Verfahren zur Herstellung von farbigen Copolymerisaten |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE668027A (https=) |
| DE (1) | DE1253915B (https=) |
| FR (1) | FR1458306A (https=) |
| GB (1) | GB1064470A (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8401166D0 (en) * | 1984-01-17 | 1984-02-22 | Bevaloid Ltd | Labelled polymer compositions |
| US5981145A (en) * | 1997-04-30 | 1999-11-09 | Clariant Finance (Bvi) Limited | Light absorbing polymers |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB622935A (en) * | 1945-06-15 | 1949-05-10 | Norsk Hydro Elek Sk Kvzelstofa | A process for the production of insoluble macro-molecular azo compounds |
| DE1102410B (de) * | 1958-12-20 | 1961-03-16 | Roehm & Haas Gmbh | Verfahren zur Herstellung von loesungsmittelbestaendigen, aus Dispersionen oder Loesungen filmbildenden, haertbaren Kunststoffen |
| GB920810A (en) * | 1958-11-21 | 1963-03-13 | Pittsburgh Plate Glass Co | Preparation of interpolymers of aldehyde-modified acrylamides |
-
1964
- 1964-08-08 DE DE1964B0078022 patent/DE1253915B/de active Pending
-
1965
- 1965-08-06 GB GB3369865A patent/GB1064470A/en not_active Expired
- 1965-08-06 BE BE668027D patent/BE668027A/xx unknown
- 1965-08-09 FR FR27697A patent/FR1458306A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB622935A (en) * | 1945-06-15 | 1949-05-10 | Norsk Hydro Elek Sk Kvzelstofa | A process for the production of insoluble macro-molecular azo compounds |
| GB920810A (en) * | 1958-11-21 | 1963-03-13 | Pittsburgh Plate Glass Co | Preparation of interpolymers of aldehyde-modified acrylamides |
| DE1102410B (de) * | 1958-12-20 | 1961-03-16 | Roehm & Haas Gmbh | Verfahren zur Herstellung von loesungsmittelbestaendigen, aus Dispersionen oder Loesungen filmbildenden, haertbaren Kunststoffen |
Also Published As
| Publication number | Publication date |
|---|---|
| BE668027A (https=) | 1966-02-07 |
| FR1458306A (fr) | 1966-11-10 |
| GB1064470A (https=) | 1967-04-05 |
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