AU726005B2 - Hydrophobically modified resin compositions and uses thereof - Google Patents

Hydrophobically modified resin compositions and uses thereof Download PDF

Info

Publication number: AU726005B2
Authority: AU; Australia
Prior art keywords: resin composition; acid; group; aminoamide; amine groups
Prior art date: 1997-03-04
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.): Ceased

Application number

AU63326/98A

Other languages

English (en)

Other versions

AU6332698A (en

Inventor

John C. Gast

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.)

Hercules LLC

Original Assignee

Hercules LLC

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.)

1997-03-04

Filing date

1998-02-20

Publication date

2000-10-26

1998-02-20 Application filed by Hercules LLC filed Critical Hercules LLC

1998-09-22 Publication of AU6332698A publication Critical patent/AU6332698A/en

2000-10-26 Application granted granted Critical

2000-10-26 Publication of AU726005B2 publication Critical patent/AU726005B2/en

2018-02-20 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

239000011342 resin composition Substances 0.000 title claims description 62
239000003795 chemical substances by application Substances 0.000 claims description 65
239000000047 product Substances 0.000 claims description 64
238000006243 chemical reaction Methods 0.000 claims description 61
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 58
239000000203 mixture Substances 0.000 claims description 53
238000004513 sizing Methods 0.000 claims description 53
150000001412 amines Chemical class 0.000 claims description 49
XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 claims description 46
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 43
150000003141 primary amines Chemical group 0.000 claims description 41
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 38
229920000768 polyamine Polymers 0.000 claims description 34
-1 cyclic anhydride Chemical class 0.000 claims description 32
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 30
239000001361 adipic acid Substances 0.000 claims description 29
235000011037 adipic acid Nutrition 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 28
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 24
150000003335 secondary amines Chemical class 0.000 claims description 24
230000000052 comparative effect Effects 0.000 claims description 22
238000000034 method Methods 0.000 claims description 20
238000010438 heat treatment Methods 0.000 claims description 14
150000003512 tertiary amines Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 10
150000008064 anhydrides Chemical class 0.000 claims description 10
239000007795 chemical reaction product Substances 0.000 claims description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 8
150000002561 ketenes Chemical class 0.000 claims description 8
229940014800 succinic anhydride Drugs 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 6
229920001281 polyalkylene Polymers 0.000 claims description 6
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
239000007900 aqueous suspension Substances 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000001991 dicarboxylic acids Chemical class 0.000 claims description 4
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical group C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
150000002763 monocarboxylic acids Chemical class 0.000 claims description 4
239000000725 suspension Substances 0.000 claims description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
150000004985 diamines Chemical class 0.000 claims description 3
238000001035 drying Methods 0.000 claims description 3
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
235000006408 oxalic acid Nutrition 0.000 claims description 3
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 2
125000002723 alicyclic group Chemical group 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000001336 alkenes Chemical class 0.000 claims description 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 2
239000001530 fumaric acid Substances 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
239000011976 maleic acid Substances 0.000 claims description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
150000002762 monocarboxylic acid derivatives Chemical group 0.000 claims 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims 1
AMOKUAKXKXBFIW-WJDWOHSUSA-N 9-[(z)-non-3-enyl]-10-octylnonadecanedioic acid Chemical compound OC(=O)CCCCCCCCC(CCCCCCCC)C(CCCCCCCC(O)=O)CC\C=C/CCCCC AMOKUAKXKXBFIW-WJDWOHSUSA-N 0.000 claims 1
238000004132 cross linking Methods 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
OZVLILWRDWSCNL-UHFFFAOYSA-N phthalic acid terephthalic acid Chemical compound C(C=1C(C(=O)O)=CC=CC1)(=O)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O.C(C1=CC=C(C(=O)O)C=C1)(=O)O OZVLILWRDWSCNL-UHFFFAOYSA-N 0.000 claims 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims 1
125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
239000000123 paper Substances 0.000 description 67
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
239000007787 solid Substances 0.000 description 49
239000006185 dispersion Substances 0.000 description 32
229920005989 resin Polymers 0.000 description 29
239000011347 resin Substances 0.000 description 29
RSPWVGZWUBNLQU-FOCLMDBBSA-N 3-[(e)-hexadec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCCCCCC\C=C\C1CC(=O)OC1=O RSPWVGZWUBNLQU-FOCLMDBBSA-N 0.000 description 21
125000002091 cationic group Chemical group 0.000 description 18
239000000243 solution Substances 0.000 description 17
238000002360 preparation method Methods 0.000 description 16
238000004821 distillation Methods 0.000 description 14
239000002245 particle Substances 0.000 description 14
229920002472 Starch Polymers 0.000 description 12
238000009833 condensation Methods 0.000 description 12
230000005494 condensation Effects 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000008107 starch Substances 0.000 description 12
235000019698 starch Nutrition 0.000 description 12
DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 11
SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000000539 dimer Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
239000000463 material Substances 0.000 description 7
PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 6
229920000147 Styrene maleic anhydride Polymers 0.000 description 6
235000011044 succinic acid Nutrition 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
239000006260 foam Substances 0.000 description 5
229940037312 stearamide Drugs 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
235000021355 Stearic acid Nutrition 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229940037003 alum Drugs 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
239000001046 green dye Substances 0.000 description 4
239000011121 hardwood Substances 0.000 description 4
239000002655 kraft paper Substances 0.000 description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000011122 softwood Substances 0.000 description 4
239000008117 stearic acid Substances 0.000 description 4
YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
244000010375 Talinum crassifolium Species 0.000 description 3
235000015055 Talinum crassifolium Nutrition 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 3
229920001187 thermosetting polymer Polymers 0.000 description 3
NGDLSKPZMOTRTR-OAPYJULQSA-N (4z)-4-heptadecylidene-3-hexadecyloxetan-2-one Chemical compound CCCCCCCCCCCCCCCC\C=C1/OC(=O)C1CCCCCCCCCCCCCCCC NGDLSKPZMOTRTR-OAPYJULQSA-N 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
GPFVWKXABQQNEM-BMRADRMJSA-N 3-[(e)-16-methylheptadec-1-enyl]oxolane-2,5-dione Chemical compound CC(C)CCCCCCCCCCCCC\C=C\C1CC(=O)OC1=O GPFVWKXABQQNEM-BMRADRMJSA-N 0.000 description 2
KAYAKFYASWYOEB-ISLYRVAYSA-N 3-[(e)-octadec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCC\C=C\C1CC(=O)OC1=O KAYAKFYASWYOEB-ISLYRVAYSA-N 0.000 description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000005642 Oleic acid Substances 0.000 description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
241001237728 Precis Species 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
238000013019 agitation Methods 0.000 description 2
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
238000000265 homogenisation Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
235000021313 oleic acid Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000001254 oxidized starch Substances 0.000 description 2
235000013808 oxidized starch Nutrition 0.000 description 2
SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229940088417 precipitated calcium carbonate Drugs 0.000 description 2
239000013055 pulp slurry Substances 0.000 description 2
230000003068 static effect Effects 0.000 description 2
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 description 1
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
HYYJOCXNESGFSB-UHFFFAOYSA-N 1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical class C1OC1CNCC1CO1 HYYJOCXNESGFSB-UHFFFAOYSA-N 0.000 description 1
CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000283153 Cetacea Species 0.000 description 1
239000009261 D 400 Substances 0.000 description 1
241000698776 Duma Species 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
235000019482 Palm oil Nutrition 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
235000021319 Palmitoleic acid Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical class OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 1
239000010480 babassu oil Substances 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
JKOSHCYVZPCHSJ-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1.CC1=CC=CC=C1 JKOSHCYVZPCHSJ-UHFFFAOYSA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000003139 biocide Substances 0.000 description 1
238000005282 brightening Methods 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
238000010411 cooking Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000000447 dimerizing effect Effects 0.000 description 1
238000002036 drum drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229910001651 emery Inorganic materials 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
210000000497 foam cell Anatomy 0.000 description 1
238000005187 foaming Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002462 imidazolines Chemical class 0.000 description 1
230000003116 impacting effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002924 oxiranes Chemical group 0.000 description 1
239000003346 palm kernel oil Substances 0.000 description 1
235000019865 palm kernel oil Nutrition 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
238000005325 percolation Methods 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
239000004302 potassium sorbate Substances 0.000 description 1
235000010241 potassium sorbate Nutrition 0.000 description 1
229940069338 potassium sorbate Drugs 0.000 description 1
238000012545 processing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
239000010499 rapseed oil Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
229960003656 ricinoleic acid Drugs 0.000 description 1
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 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
239000001384 succinic acid Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
239000012085 test solution Substances 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/16—Sizing or water-repelling agents
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
- C08G73/0286—Preparatory process from polyamidoamines and epihalohydrins
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
- D21H17/56—Polyamines; Polyimines; Polyester-imides

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Paper (AREA)
Graft Or Block Polymers (AREA)

AU63326/98A 1997-03-04 1998-02-20 Hydrophobically modified resin compositions and uses thereof Ceased AU726005B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US81209297A	1997-03-04	1997-03-04
US08/812092		1997-03-04
PCT/US1998/003358 WO1998039376A1 (en)	1997-03-04	1998-02-20	Hydrophobically modified resin compositions and uses thereof

Publications (2)

Publication Number	Publication Date
AU6332698A AU6332698A (en)	1998-09-22
AU726005B2 true AU726005B2 (en)	2000-10-26

Family

ID=25208473

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU63326/98A Ceased AU726005B2 (en)	1997-03-04	1998-02-20	Hydrophobically modified resin compositions and uses thereof

Country Status (6)

Country	Link
EP (1)	EP0907672A1 (de)
AU (1)	AU726005B2 (de)
CA (1)	CA2261954A1 (de)
TW (1)	TW495538B (de)
WO (1)	WO1998039376A1 (de)
ZA (1)	ZA981848B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6702923B1 (en)	1999-11-19	2004-03-09	Akzo Nobel Nv	Wet strength agent and method for production thereof
US20020096281A1 (en)	1999-11-19	2002-07-25	Hans Wallenius	Wet-strong tissue paper
JP2003515006A (ja) *	1999-11-19	2003-04-22	アクゾノーベルエヌ．ブイ．	湿潤強度増強剤およびその製造方法
US6673205B2 (en) *	2001-05-10	2004-01-06	Fort James Corporation	Use of hydrophobically modified polyaminamides with polyethylene glycol esters in paper products
SE522783C2 (sv) *	2001-05-18	2004-03-09	Sca Hygiene Prod Ab	Våtstarkt tissuepapper
CA2461629C (en)	2003-03-24	2012-05-08	Nof Corporation	Paper additive composition and method for producing paper using the same
US7041197B2 (en)	2003-04-15	2006-05-09	Fort James Corporation	Wet strength and softness enhancement of paper products
US8651285B2 (en) †	2009-08-19	2014-02-18	Johns Manville	Performance polymeric fiber webs
AU2012236373B2 (en)	2011-03-31	2016-06-23	Solenis Technologies Cayman, L.P.	Sizing compositions

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3922243A (en) *	1973-08-31	1975-11-25	Hercules Inc	Ketene dimer modified water-dispersible thermosettable cationic resins
US4478682A (en) *	1981-07-02	1984-10-23	Hercules Incorporated	Sizing method and sizing composition for use therein

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4200715A1 (de) *	1992-01-14	1993-07-15	Bayer Ag	Vinylpolymerisat-dispersionen

1998
- 1998-02-20 EP EP98907552A patent/EP0907672A1/de not_active Withdrawn
- 1998-02-20 CA CA002261954A patent/CA2261954A1/en not_active Abandoned
- 1998-02-20 AU AU63326/98A patent/AU726005B2/en not_active Ceased
- 1998-02-20 WO PCT/US1998/003358 patent/WO1998039376A1/en not_active Ceased
- 1998-03-04 ZA ZA981848A patent/ZA981848B/xx unknown
- 1998-03-05 TW TW087103237A patent/TW495538B/zh active

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3922243A (en) *	1973-08-31	1975-11-25	Hercules Inc	Ketene dimer modified water-dispersible thermosettable cationic resins
US4478682A (en) *	1981-07-02	1984-10-23	Hercules Incorporated	Sizing method and sizing composition for use therein

Also Published As

Publication number	Publication date
EP0907672A1 (de)	1999-04-14
WO1998039376A1 (en)	1998-09-11
ZA981848B (en)	1998-09-04
AU6332698A (en)	1998-09-22
TW495538B (en)	2002-07-21
CA2261954A1 (en)	1998-09-11

Legal Events

Date	Code	Title	Description
2001-02-22	FGA	Letters patent sealed or granted (standard patent)
2003-09-18	MK14	Patent ceased section 143(a) (annual fees not paid) or expired

Publication	Publication Date	Title
US4240935A (en)	1980-12-23	Ketene dimer paper sizing compositions
US4144123A (en)	1979-03-13	Incorporating a crosslinked polyamidoamine condensation product into paper-making pulp
US5567798A (en)	1996-10-22	Repulpable wet strength resins for paper and paperboard
US4243481A (en)	1981-01-06	Sizing compositions
US4317756A (en)	1982-03-02	Sizing composition comprising a hydrophobic cellulose-reactive sizing agent and a cationic polymer
US6485555B1 (en)	2002-11-26	Sizing composition
JPS627216B2 (de)	1987-02-16
US4295931A (en)	1981-10-20	Sizing method and sizing composition for use therein
JPS6215680B2 (de)	1987-04-08
AU726005B2 (en)	2000-10-26	Hydrophobically modified resin compositions and uses thereof
US4478682A (en)	1984-10-23	Sizing method and sizing composition for use therein
JP5217240B2 (ja)	2013-06-19	紙用添加剤およびそれを使用した製紙方法
US5393338A (en)	1995-02-28	Cationic compounds useful as drainage aids and stabilizers for rosin-based sizing agents
US3922243A (en)	1975-11-25	Ketene dimer modified water-dispersible thermosettable cationic resins
US4407994A (en)	1983-10-04	Aqueous sizing composition comprising ketene dimer and epihalohydrin/polyamino polyamide/bis(hexamethylene)triamine reaction product
FI62126C (fi)	1982-11-10	Vattendispersion av foerstaerkt kolofonium
JP3205628B2 (ja)	2001-09-04	紙のサイジング方法
EP0066366B1 (de)	1986-11-20	Verzweigte Polyamidamine, Verfahren zu deren Herstellung und Verfahren zur Verbesserung der Nassfestigkeit von Papier unter Anwendung derselben
US4416729A (en)	1983-11-22	Ammonium polyamidoamines
US3728215A (en)	1973-04-17	Aminopalyamide{13 acrylamide{13 polyaldehyde resins employing an alpha, beta-unsaturated monobasic carboxylic acid or ester to make the aminopolyamide and their utility as wet and dry strengthening agents in papermaking
US3992251A (en)	1976-11-16	Process of making wet strength paper containing mono primary polyamine and organic dihalide modified, epoxidized polyamide
US3988280A (en)	1976-10-26	Water-dispersible thermosettable cationic resins and paper sized therewith
JPS6215679B2 (de)	1987-04-08
US3990939A (en)	1976-11-09	Paper sized with ketene dimer modified water-dispersible thermosettable cationic resins
US3989659A (en)	1976-11-02	Water-dispersible thermosettable cationic resins and paper sized therewith